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24: Tailwind CSS with Adam Wathan

24: Tailwind CSS with Adam Wathan

The Art of Product 17 November 2017

Episode Description

Ben and Derrick are joined by guest Adam Wathan, an esteemed software developer, writer, speaker and entrepreneur from Ontario, Canada. He is the creator of Tailwind CSS, author of Refactoring to Collections and host of the Full Stack Radio podcast. Listen in as he shares how he built his own products over time and became an independent entrepreneur, and talks about his new project Tailwind CSS.

Today’s Topics Include:

Starting his first side projects and products
Adam’s successful marketing channels and strategies
Lessons learned from past product launches
Experience with pricing plans and tiers
Adam’s current projects and products, including Tailwind CSS
CSS programming, utility and presentation

If you’re enjoying the show please give us your ratings and reviews in iTunes.

Links and resources:

Tailwind CSS
Test-Driven Laravel
Refactoring to Collections
Full Stack Radio
Adam on Twitter @adamwathan
The 30-Day Code Quality Challenge
RefactoringRails.io
Drip

...see more

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17 November 2021


192: This Is Not A Fire Drill

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13 October 2021


188: Priorities, Priorities

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Ben and Derrick strategize about how to allocate time and energy and staying in tune with customers.

6 October 2021


187: Wait, There Are How Many Time Zones?!

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Derrick & Ben share updates on where they are spending their time moving their businesses forward.

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173: Shreyas Doshi on Product Management

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12 May 2021


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Ben interviews Len Markidan, CMO at Podia about hiring a Head of Marketing for Tuple. Job description: https://tuple.app/jobs/head-of-marketing

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171: Humans Have A Lot of Drawbacks

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170: Beautifully, Wonderfully Dissatisfied Customers

The Tuple team is close to shipping true 3-player mode without host & observer role limitations. Derrick launched the Outlook integration this week and is working on a bunch of smaller tasks that have been accruing the past month.

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Ben & Derrick chat about dealing with ups & downs in business, finding enough, decoupling fulfillment from business metrics, knowledge archival, dealing with feature requests, and slew of other topics.

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168: I'd Rather Commit Sins of Overambition

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Ben & Derrick brainstorm a "rooms" feature for Tuple. Derrick is getting close to wrapping up the SavvyCal Outlook integration. Ben shares highlights from their latest team retreat and teases some new plans for later this year.

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1 April 2021


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166: Hello from Linux

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25 March 2021


165: The Art of Negotiation

165: The Art of Negotiation

Ben and Derrick chat about tools for collaboration and their recent experiences with negotiating deals. Ben wants to level up this year on the marketing front. Work is underway on the SavvyCal integration with Outlook Calendar.

18 March 2021


164: We Love A Good Null Constraint

164: We Love A Good Null Constraint

Ben and Derrick chat about joy of shipping features quickly that customers love. They also discuss architecting software to minimize painful changes in the future. The Tuple team is making progress on the Linux client and SavvyCal is working on an Outlook integration.

11 March 2021


163: Catching Up With Paul Jarvis

163: Catching Up With Paul Jarvis

Ben and Derrick hang out and talk shop with Paul Jarvis, co-founder of Fathom Analytics (https://usefathom.com/).

4 March 2021


162: Do You Even Clubhouse?

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Ben is working on refining the Tuple company operating system. Derrick reflects on the kind of company he hopes to build and the merits of growing & managing a team vs staying tiny. The guys share their take on Clubhouse.

25 February 2021


161: The Podia Operating System

161: The Podia Operating System

This week, Ben chats with Spencer Fry (http://www.spencerfry.com/), CEO and Founder of Podia (https://www.podia.com/). Spencer's smart. You should probably listen to him.

18 February 2021


160: Digging Moats

160: Digging Moats

The Tuple team is releasing a batch of nice improvements and gearing up for taking on the Linux client project. Ben touched some code recently. Derrick is knocking out a swath of small features that customers have been requesting and is getting closer to building more calendar integrations.

4 February 2021


159: Does Tuple Ever Crash?

159: Does Tuple Ever Crash?

Tuple's latest release is the least crashy of them all! The team is gearing up for the Linux client and feeling energized to take on the challenge. SavvyCal is now officially Derrick's highest grossing independent SaaS endeavor. They are launching a "buy out your annual Calendly subscription" (https://savvycal.com/calendly-buyout)campaign this week.

28 January 2021


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158: There's Nothing Like a Sharp Knife

Derrick & Ben chat about health, hobbits, and habits. Derrick reveals more numbers from the Product Hunt launch and talks through upcoming plans for the product. Links: Sweet Maria's (https://www.sweetmarias.com/) Ken Onion Knife Sharpener (https://www.amazon.com/Work-Sharp-Knife-Sharpener-Onion/dp/B07CW4T6RS) Product Hunt listing (https://www.producthunt.com/posts/savvycal)

21 January 2021


157: SavvyCal Wins Product Hunt

157: SavvyCal Wins Product Hunt

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14 January 2021


156: Reflections on 2020

156: Reflections on 2020

Ben & Derrick reflect on their journeys the past year and their plans for 2021.

7 January 2021


155: How Do You Buy A New Habit?

155: How Do You Buy A New Habit?

Ben wants to build a meditation habit and is considering ways to facilitate that. Tuple is still searching for a product designer. Derrick & Ben both saw success with their year-end annual upgrade promotions. Derrick is planning a Product Hunt launch in early January.

31 December 2020


154: Courtland Allen Must Be Stopped

154: Courtland Allen Must Be Stopped

We're nominated for the SaaS Podcast Awards (https://microconf.com/latest/saas-podcast-award-nominees/) - go vote! The guys muse about the clever marketing behind the awards and their fellow nominee Courtland Allen's unfair charm & good looks. Ben talks through a shared clipboard feature he is shaping for Tuple. Derrick shipped a bunch of marketing projects this past week.

17 December 2020


153: The Value of Coaching

153: The Value of Coaching

The Tuple team is finishing up 3-player mode. Ben is continuing to derive value out of coaching (this time with video games). Derrick shipped a 7-day free trial for SavvyCal and competitor comparison pages.

10 December 2020


152: Default Alive By Spring

152: Default Alive By Spring

Ben opened up a job listing for Senior Product Designer at Tuple. The Tuple team is working on full-featured multi-participant calls. Derrick shipped embedding SavvyCal links on websites and is working on a number of website updates with Corey. Derrick hopes to achieve default alive state by spring through a combination of marketing efforts.

26 November 2020


151: The One Comma Club

151: The One Comma Club

Derrick reached an important revenue milestone for SavvyCal. Ben is looking forward to an upcoming Tuple retreat.

19 November 2020


150: It's Like The Vinyl Of Telling Time

150: It's Like The Vinyl Of Telling Time

Ben and Derrick discuss some recent instances of founder CEOs stepping down from their posts. Derrick is shipping a unique feature this week. Ben is trying (but failing) to avoid getting into antique watches.

12 November 2020


149: Check Your Business Privilege

149: Check Your Business Privilege

Derrick has found a new groove working in public again. Ben is polishing a job posting for a Senior Product Designer role at Tuple. The guys discuss long-term visions and harvesting profits vs. reinvesting in the business.

5 November 2020


148: No Design Survives Contact With The DOM

148: No Design Survives Contact With The DOM

Ben is enjoying working on marketing activities. Tuple is beginning their experiment of offering pairing coaching calls to customers. Derrick shipped a differentiating feature and received very positive response. A new part-time head of marketing is starting with SavvyCal in November. The guys opine about specialists vs. generalists.

29 October 2020


147:  Incremental Shipping

147: Incremental Shipping

Derrick shipped the next part of team functionality, which opened the door for expansion revenue. Ben is zeroing in on hiring a pairing coach for Tuple customers. In his down time, Ben is taking up playing the piano - something his childhood self would be appalled about.

22 October 2020


146: Growing Teams

146: Growing Teams

The Tuple team is contracting with Thoughtbot for pairing and leveling up their Rails skills. Derrick is working on team permissions and thinking about working with a marketer after wrapping up most of the work around the StaticKit sale.

15 October 2020


145: What's Next for StaticKit

145: What's Next for StaticKit

Derrick is joined by Cole Krumbholz to talk about Formspree's (https://formspree.io/)acquisition of StaticKit (https://statickit.com/). They delve into Cole's history as a bootstrapped founder, dealing with competition, defining success, how the deal came together, and what's next for both products.

8 October 2020


144: Launching SavvyCal

144: Launching SavvyCal

SavvyCal (https://savvycal.com/) is officially launched! Derrick talks through how the launch went and how he's managing his freshly-restocked information pipeline. The Tuple team is nearing the finish line on their large upcoming release and recorded a "peek behind the curtains" screencast for customers.

24 September 2020


143: Networking Thoughts

143: Networking Thoughts

Ben is trying out Roam (https://roamresearch.com/) for organizing his notes. He shares some tips for engineers applying for jobs. After manually onboarding customers for a few weeks, Derrick is soft-launching SavvyCa (https://savvycal.com/)l to accelerate his learning from real-world customers.

17 September 2020


142: A Savvy Rebrand

142: A Savvy Rebrand

Ben reflects on their latest all-hands meeting and a major upcoming release that will improve the Tuple internals. Derrick recounts the Mighty Cal rebrand to SavvyCal.

10 September 2020


141: Hiring Optimally

141: Hiring Optimally

Derrick is continuing to manually onboard Mighty Cal users and is incorporating their feedback into the product. He is driving towards optimizing self-service onboarding to enable opening up signups more broadly. Ben is considering hiring a someone to optimize trial conversions. They discuss OKRs and what skills this person might need.

27 August 2020


140: We Have Customers

140: We Have Customers

Ben is looking to hire a WebRTC expert to prepare Tuple for multi-way calls and continue improving performance. Derrick has onboarded a handful of paying Mighty Cal customers and is rapidly iterating on their feedback. Oh, and Ben has groceries now.

13 August 2020


139: Efficiency Starts With Groceries

139: Efficiency Starts With Groceries

Ben is taking his first day off in a while to recharge. He's experimenting with clustering calls on specific days to allow for more focus time on other days. Derrick finished the Zoom integration for Mighty Cal and experienced the joy (and sorrow) of onboarding his first outside user.

30 July 2020


138: That's Not How Cults Work

138: That's Not How Cults Work

Derrick has officially begun using Mighty Cal for his own scheduling needs. He plans to start onboarding early users this week. The Zoom integration is underway. Ben is considering ways to compensate and incentivise Tuple hires. As Tuple keeps growing quickly, Ben continues to navigate decision fatigue and transitioning from individual contributor to business operator.

23 July 2020


137: Approved!

137: Approved!

Mighty Cal received Google API verification this week, which was a critical blocker to onboarding users. Derrick worked on scheduling link personalization this week. The Tuple team revamped their call feedback form and are now receiving a broader spectrum of messages from customers.

16 July 2020


136: Feedback Is Everything

136: Feedback Is Everything

Ben ran his first all-hands meeting this week. Tuple got featured in a Stripe blog post about the customer portal feature that Tuple was beta testing. Ben has some observations about how Stripe approaches product development. Derrick reached his goals this week with Mighty Cal and is now working toward onboarding the first customers.

9 July 2020


135: Do We Really Need An Office?

135: Do We Really Need An Office?

Derrick is driving toward the first milestone of using Mighty Cal (https://mightycal.com/) for his own scheduling and is facing the reality of setting ambitious goals for the week. The Tuple team moved into their new office, which spurred on a healthy conversation about the value of working in-person and accessing the remote talent pool.

2 July 2020


134: Introducing Mighty Cal

134: Introducing Mighty Cal

Derrick details the launch of the landing page for his new scheduling app, Mighty Cal. The Tuple team took a retreat and did a feedback exercise modeled after the Great CEO Within. Tuple is officially moving into their first office.

25 June 2020


133: Perfect Is The Enemy Of Good

133: Perfect Is The Enemy Of Good

Derrick is dangerously close to shipping his MVP, but is also lamenting how long it's taking. He's committed to naming a public ship date by next recording time. Ben is on the hunt for an executive coach. The Tuple Boston team is eyeing their first real office space outside of Joel's condo.

18 June 2020


132: Digging a Moat

132: Digging a Moat

We're back! The Tuple client redesign shipped and Derrick is going to help out with an overhaul of the Tuple onboarding process. Ben asked for users to record their first-run experience in exchange for a discount and has learned a ton about what could be improved. The Tuple team is considering how best to plan out their roadmap this quarter.

11 June 2020


131: Making Calculated Bets

131: Making Calculated Bets

Derrick had a productive maker week and is (hopefully) a few weeks out from onboarding his first customers for the new product. He is becoming well-acquainted with the Google Calendar API. The Tuple team hired a full-time Mac OS engineer. Ben is thinking about opportunities to innovate with Tuple and taking inspiration from Bezos' shareholder letters.

21 May 2020


130: Certainty Isn't The Goal

130: Certainty Isn't The Goal

Tuple hired a firm for QA testing and is gradually ramping them up. Derrick is exploring how best to approach architecting the initial version of his new product (still in stealth mode) and is taking inspiration from Ryan Singer and Jason Fried's recent Rework episode on product strategy (https://rework.fm/product-strategy/).

14 May 2020


129: Remember When Software Came on Floppy Disks?

129: Remember When Software Came on Floppy Disks?

Derrick explores the difference between the craft of software development and the building minimum-viable products (and why it's good to exercise both). Ben explores hiring a QA testing firm. They reflect on the nature of shipping software and the differences between web apps and native, cross-platform apps.

30 April 2020


128: One Day At A Time

128: One Day At A Time

Derrick is enjoying work the last week by taking joy in setting and achieving small goals each day. The Tuple redesign project is nearing completion and has been a welcome distraction from the pandemic. Ben is hiring a full-time Mac OS engineer and an accountant to help with managing the money side of the business.

23 April 2020


127: A Tuple Growth Spurt

127: A Tuple Growth Spurt

The Tuple team is growing as Ben kicks up sales efforts with help of an industry veteran and the engineering team onboards a new team member. Derrick is continuing to work in stealth mode on a new product and is bringing in some cash flow from a consulting project with...tune in to find out.

9 April 2020


126: Tuple Takes Over

126: Tuple Takes Over

Ben and Derrick hang out with Tuple co-founders Spencer and Joel and talk shop. They discuss what it's really like to work with Ben, how they approach learning deeply technical things, ways they are preparing for a new engineering hire, and that time they hard-coded user IDs into Tuple.

2 April 2020


125: Keeping Things in Perspective

125: Keeping Things in Perspective

Ben and Derrick are doing their best to focus right now with so much going on in the world. Ben is spending less time on Twitter these days. Derrick is working on hedging his opportunity bets by doing jobs-to-be-done interviews in the scheduling space.

26 March 2020


124: Back After A Break

124: Back After A Break

Suntans and sunburns aside, Derrick’s winter escape to Mexico provided meaningful ideas and perspective on StaticKit. By reading, Competing Against Luck (https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612), Derrick’s goal is to be innovative and gain traction in product/market fit by asking customers the right questions and identifying jobs to be done. Ben recommends reading, Schlep Blindness (http://paulgraham.com/schlep.html) by Paul Graham. It describes how startup ideas remain a painful process instead of a phenomenon. Also, Ben announced that Tuple wants to hire a part-time remote developer with Mac iOS and C++ experience. Recently, Ben realized that writing is better than talking when it comes to business communication and conversations.

19 March 2020


123: Customer Service as a Competitive Advantage

123: Customer Service as a Competitive Advantage

Ben put big and new priorities to the side to cover support for Tuple. By doing so, he discovered different opportunities to reduce the number of support requests received. It’s challenging to work on the right things in a smart order. Derrick knows how support is one of the best ways to identify pain points with your product. He describes how founders often follow their passion instead of their priorities. With StaticKit, Derrick is expanding his focus to align tools that he’s building to meet niche market demand. However, less is more when it comes to outreach and emails.

27 February 2020


122: SaaS Sales with Matt Wensing

122: SaaS Sales with Matt Wensing

Even if a product, such as Tuple, is good and people don’t need to be convinced to buy it, there’s still plenty of work to be done. It involves communication, coordination, and collaboration. Ben’s perfect sales pitch and ultimate goal: Sell once, revenue forever. Ben picks his guest co-host’s brain about big deals with major companies. Luckily, Matt Wensing is willing to share his enterprise sales experience, including setting price points, hiring salespeople, and developing documentation. Matt is the founder and CEO of Summit, Out of Beta podcast host, and Riskpulse founder.

20 February 2020


121: Futureproofing Your Business

121: Futureproofing Your Business

Ben never wants to stop working on his startup company, Tuple. Despite some stress, it’s successful and satisfying. However, team members may be added to take over some of Ben’s responsibilities. Based on the book, The Great CEO Within, Ben continues to provide feedback and to document standard operating procedures, policies, and other information to handle the challenge of knowledge management. Derrick emphasizes the importance of documentation, support, and smooth transitions. You don’t know what other people don’t know. Derrick wants to be doing what he’s doing with his startup, StaticKit, but is feeling weary and may be willing to eventually step aside. While attending a TinySeed Retreat, he was reminded of how face-to-face meetings are worthwhile, and it’s good to surround yourself with successful people who share similar experiences.

13 February 2020


120: Product Pricing with Adam Wathan

120: Product Pricing with Adam Wathan

When’s the last time you read a manual or document to know how to use product features and functions? Ben’s new mantra: Write it down! Rather than repeat expertise, reuse content. Currently, Tuple’s most unreliable part is its online users list. Beat the competition by doing what others can’t do Ben and special guest, Adam Wathan (https://adamwathan.me/), address product pricing and licensing questions. Adam hosts Full Stack Radio, created Tailwind CSS, and authored Refactoring UI. He encourages writing simple and succinct stories despite complex information. Also, Adam describes how products on the market look sexy, but may not work well under the hood.

6 February 2020


119: Undoing a Twitter Addiction

119: Undoing a Twitter Addiction

If you’re spending too much time on Twitter, Ben shares some helpful advice. Fully lock and block it by setting parental controls and content restrictions. While attending Big Snow Tiny Conf (https://bigsnowtinyconf.com/), Ben’s awareness of his Twitter addiction could no longer be denied. He successfully resisted being lured back into the app. Also, Tuple launched its Apple Pro Display XDR stand giveaway (https://publicity-stunt.tuple.app/). So far, a sense of humor has generated a positive brand impression and collected more than 900 email addresses. Derrick describes how StaticKit started as a form provider for static sites, but he continues to build out its functionality by offering tooling to collect payments via Stripe (https://stripe.com/). He discovered that trying to force payments in a form model posed many challenges. He decided to offer the same type of functionality as functions, instead of forms. Derrick is feeling content and confident with where the product stands relative to reinventing the model and changing the original vision.

30 January 2020


118: Reliability and Minimalism

118: Reliability and Minimalism

Ben’s back from Tuple’s ski trip retreat, where survey responses were reviewed for strategic planning purposes. Turns out that those who value pair programming actively use Tuple. What’s Tuple doing well? Latency and low friction. What can be added, changed, or improved? Free text, and make the basics a bit more stable and reliable. Ben knows it’s expensive and annoying to run tests all the time, but it’s also possible to mess something up that’s good. From building Level, Derrick understands how minor deviations to features can become major annoyances for customers. However, he’s still on track with his goal to be intentional with the material he consumes by reading Digital Minimalism (https://www.calnewport.com/books/digital-minimalism/). Derrick’s feeling zen and reaping the benefits of dumbing down his devices but not getting sucked back in. Plus, he continues to make progress with StaticKit and has moved from prototype to production. Stay tuned!

16 January 2020


117: Our 2020 Roadmap

117: Our 2020 Roadmap

New Year’s Resolutions? Ben’s goal is to drink less coffee and get a survey out to Tuple customers. What do they want in the future for Tuple features? Are people using Tuple for reasons other than original core assumptions? Ben is looking forward to collecting customer insights to determine if they are on the same product development roadmap. Derrick came up with trends, themes, and habits that he hopes to cultivate and aspire to in 2020. He wants to exhibit intentionality with how he spends his time and not be a slave to Slack, Twitter, and other channels. Does Derrick have adequate self-control, or a suitable replacement? Self-control takes time, energy, and money. However, spending free time letting his mind wander helped Derrick develop a deliberate API design around payments for StaticKit.

9 January 2020


116: Should We Be Setting Annual Goals?

116: Should We Be Setting Annual Goals?

In the last episode of 2019, Derrick and Ben focus on reflections and projections. Should they set goals for the coming year when it comes to Tuple and StaticKit? After all, nobody can predict the future, and hard work doesn’t always lead to perfect products and startups. But it’s been an amazing year for Tuple, which went from zero to hundreds of customers. What’s next? Adding cross-platform operating systems and going with freemium pricing model? Always looking ahead, how good are Tuple founders at predicting the future? Time will tell, once they receive their delay emails. Derrick describes how goals can lead to unhealthy behavior. Recently, he spent time with TinySeed mentor, Dr. Sherry Walling, talking about burnout and other mental health aspects for founders of startups. What are the early signs of burnout? Burning the candle at both ends. So, Derrick’s goal is to be less stressed by having more fun and enjoying the journey. Next year is going to be an interesting one for both Derrick and Ben!

26 December 2019


115: Debunking the Arrival Fallacy

115: Debunking the Arrival Fallacy

Ben has turned out to be a terrific tweeter about Tuple on Twitter. So far, more than 750k impressions have been made regarding his post about the enterprise sales process. He also shared that Tuple’s scaling issues appear to be resolved and fixed. He gave a shout out to the team at You Need A Budget (https://www.youneedabudget.com) (YNAB) for consistent and concise support. Plus, Ben has started using Anki (https://apps.ankiweb.net) flashcards to spark his memory and recall names via mnemonics. Derrick reminds us that the last ‘S’ in SaaS is service. He describes how to prevent and combat arrival fallacy and enjoy the journey. So, should he set goals, plan ahead, and look forward to the future of StaticKit? Or, is that too stressful? Will arrival points and milestones bring him happiness? No matter what, Derrick is looking forward to sharing insight about being a skeptic of frontend static Web pages by presenting at ZEIT’s Backendless Conf (https://backendlessconf.com/).

19 December 2019


114: Building Today For Tomorrow's Growth

114: Building Today For Tomorrow's Growth

Ben describes how a recent Tuple tweet led to thousands of impressions and mentions, as well as possibly increased free trial sign-ups. Ben is experiencing the enterprise sales process where he could make a good deal of money from a large company, if he chooses to meet its numerous demands. Also, Tuple is making progress with scaling challenges by addressing related Heroku and Ruby issues. Tuple’s smallness is a strength! Derrick’s been working on API design for StaticKit’s payments plug-in, especially to handle European customer authentication regulations that Stripe is moving toward. However, complex and flexible API design can’t be rushed to meet requirements. Derrick hopes to move StaticKit’s interface to his Next.js application. Constantly learning new technologies is critical to know his customer base. So, Derrick was pleased to be invited to present at ZEIT’s Backendless Conf. (https://backendlessconf.com/)

12 December 2019


113: Rounding out the Product Roadmap

113: Rounding out the Product Roadmap

Derrick shipped a few things for StaticKit, including Mailchimp and ConvertKit integrations. What’s next? Stripe integration. For now, Derrick is targeting more technical users comfortable with code. At some point, he will involve “no-code” users who can easily drop-in Derrick’s plug-in. He’s done all the hard work for them. Check out new content he created, such as guides and features-specific landing page for opt-in forms (https://t.co/cW3Eo0JCBS). Ben decided to take some time off and away from Tuple during the Thanksgiving holiday. It’s just one of the lifestyle perks of being part of a startup. Ben finally settled on transitioning away from Drip to Customer.io for Tuple’s transactional emails. However, Tuple continues to deal with scaling issues on the infrastructure side. Are problems due to capacity? Memory? Something’s wrong, but not sure what and why...TBD. Yet, November proved to be Tuple’s best month so far with record-breaking growth!

5 December 2019


112: The Evolution of Product Positioning

112: The Evolution of Product Positioning

Ben announced the release of a new version of Tuple. The app includes improvements to its Webcam feature and requires less CPU usage and bandwidth. Also, Ben decided to turn off payment notifications from Stripe. Thankfully, too many emails created too much noise. He understands the value of not sending lots of emails, but the right emails to educate Tuple’s target market. Tuple’s pricing page and corporate swag will be released soon. As a Superhuman user, Ben offered Derrick advice on implementing it via Chrome or Electron, as well as a setting to remove badges. In addition to Zapier, Derrick’s working on a Mailchimp integration for StaticKit. He stresses the importance of evolving product positioning to make compelling marketing. Yet, Derrick describes TinySeed’s growth goal that he got as ambitious and unlikely to be achieved.

21 November 2019


111: Continuous Improvement for Growth

111: Continuous Improvement for Growth

Derrick shipped a revamped version of StaticKit’s homepage and plans to add a payments section soon. He’s eager to conduct another round of customer development calls. If you want to chat about your experience with static sites and help shape product direction for StaticKit, schedule a call with Derrick on Calendly. (https://calendly.com/derrickreimer/statickit-chat?month=2019-11) Ben already utilizes a checkout option for Tuple and shares some of its challenges. Also, Ben announced and shipped the release of a highly requested and expected Tuple feature—ability to start a Tuple session without sharing your screen. Despite Tuple’s burst of free trial signups, Ben described a decreased conversion rate to paying customers. Both Ben and Derrick share how design matters, especially when upgrading or switching browsers and operating systems that make your app look like a scam and sketchy!

14 November 2019


110: The Importance of Mentors

110: The Importance of Mentors

Derrick shipped config file for StaticKit’s UI migration and shifted his focus to other areas of the product. He plans to deliberately and consistently test email messages to determine which generate response and interest in StaticKit. He continues to connect with TinySeed mentors. Ben understands the value mentors offer in helping entrepreneurs easily avoid bad ideas and pursue good ones. Also, he’s working on writing content for his October advisor update. What’s the next step following Tuple’s free trial? T-shirt? Should Ben think bigger and Shape Up?

7 November 2019


109: Split Test = Optimization

109: Split Test = Optimization

Some podcasts present terrible sound quality, yet garner tons of listeners. Ben and Derrick are professionals, and care about the sound quality of their AoP podcast episodes. Despite audio difficulties, Ben and Derrick are back. They sound good, and they’re ready to rock their updates on StaticKit and Tuple! Today’s Topics Include: Should you test? Trust weak data? Split-test customer email messaging tools should push you to test as default path (Not) Steady State of New Trials: Email blast offering free Tuple trial to everybody Tuple T-shirt Prototype: Take the next step in funnel to pay for Tuple to get T-shirt Structure and Process: Sense of energy from Tuple’s stand ups and status updates Tuple to handle classic startup chaos by reading, Shape Up: Stop Running in Circles and Ship Work that Matters by Ryan Singer StaticKit Solopreneur: Derrick’s suffering from decision fatigue, struggling to juggle multiple tasks, and balancing building a great product and connecting with customers Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) TinySeed (https://tinyseed.com/) Using Tailwind CSS with Next.js (https://statickit.com/guides/next-js-tailwind)  Level (https://level.app/) Audio-Technica ATR2100 USB (https://www.audio-technica.com/cms/wired_mics/b8dd84773f83092c/index.html) Drip (https://www.drip.com/) Shape Up (https://basecamp.com/shapeup) JAMstack Conf (https://jamstackconf.com/) Slack (https://slack.com/)

31 October 2019


108: Getting Back to Growth Planning

108: Getting Back to Growth Planning

Derrick returned from JAMstack Conf with a jolt of energy and excitement thanks to face-to-face conversations and strategic connections with potential StaticKit customers. Ben expressed interest in once again speaking at developer conferences. After all, he has plenty of worthwhile information and lessons learned to share about Tuple. Today’s Topics Include: Frontend and Backend: Considerations for implementation/migration with StaticKit Main Objective at JAMstack: Market validation, not to make sales to customers Future Feature: Allows people to configure StaticKit account via config file Prevent UI Creep and Wall of Fields: Keep it elegant, but flexible and customizable Instant Gratification and Relief: Numbers are rising again after Tuple’s sign-up fluctuation Tuple Trick: Free, two-week trial for submitting email via invite box; stabilization and scaling are serious concerns due to more customers Ben’s optimism leads to deleted tweet about Tuple T-shirts How much MMR is enough? Never enough; bigger, brighter, more interesting future Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://statickit.com/) TinySeed (https://tinyseed.com/) Using Tailwind CSS with Next.js (https://statickit.com/guides/next-js-tailwind)  JAMstack Conf (https://jamstackconf.com) MicroConf (https://microconf.com/) Slack (https://slack.com/) Netlify (https://www.netlify.com/) WordPress (https://wordpress.com/) Drupal (https://www.drupal.org/) JSON (https://www.json.org/) Drip (https://www.drip.com/) Justin Jackson (https://twitter.com/mijustin) Shopify (https://www.shopify.com/) Rob Walling (https://robwalling.com/) Paul Jarvis (https://ofone.co) Jason Fried (https://twitter.com/jasonfried)

24 October 2019


107: Becoming a Multi-Product Company (with Amir Salihefendić)

107: Becoming a Multi-Product Company (with Amir Salihefendić)

Derrick and Ben welcome Amir Salihefendić, founder and CEO of Doist. Ben was able to break away from Slack and uses Doist’s Twist app at Tuple for team communication. Also, Ben and Derrick share updates and experiences about their businesses that spark familiarity and advice from Amir based on his entrepreneurial adventures. Today’s Topics Include: Founder Therapy: Derrick helped talk Ben off the ledge and figure things out with Tuple Live and Learn: An entrepreneur starting a business is on a psychology rollercoaster Ben’s path forward to break past lull via positive momentum and mood Short-and-Simple Answer: Derrick should only focus on long-term goals for StaticKit Looking forward to new release of Todoist in a few weeks? New features added with emphasis on improving existing design and workflow 360 Review: Stop doing development, and focus time on CEO role and responsibilities Balancing Act: Difficult to start companies and launch multiple products; but worth long-term investment and effort Unless your target audience is college students and you enjoy fighting churn, Doist’s pricing strategy isn’t recommended Synchronous vs. Asynchronous: Working remotely may impact your mental health Links and resources: Doist (https://doist.com) Twist (https://twist.com) Todoist (https://todoist.com/?lang=en) Success Ten Years in the Making with Amir Salihefendic of Doist (https://www.indiehackers.com/forum/success-ten-years-in-the-making-with-amir-salihefendic-of-doist-c44b42761e) Slack (https://slack.com/) Rob Walling (https://robwalling.com/) Fooled by Randomness (https://www.amazon.com/Fooled-Randomness-Hidden-Markets-Incerto/dp/0812975219) Tyler Tringus (https://tylertringas.com/) Nathan Barry  (https://nathanbarry.com) MicroConf (https://microconf.com/) Drip (https://www.drip.com/) jQuery (https://jquery.com/) Adam Wathan (https://adamwathan.me/) WeWork (https://www.wework.com/) Out of Beta Podcast (https://outofbeta.fm/) Bootstrapped Web Podcast (http://bootstrappedweb.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) TinySeed (https://tinyseed.com/) Using Tailwind CSS with Next.js (https://statickit.com/guides/next-js-tailwind)  Level (https://level.app/)

17 October 2019


106: Creating Growth Key Metrics

106: Creating Growth Key Metrics

Derrick spent his birthday at the north shore of Lake Superior to disconnect and getaway. Yet, he found some time to brainstorm and problem solve for StaticKit. Ben’s back from Martha’s Vineyard, only to experience less positive updates for Tuple. For the first time, Tuple is shockingly “in the red” financially. So, he feels guilty about going away. Today’s Topics Include: Slow Growth: Substantially fewer Tuple trial signups than previous time periods Marketing and Sales Strategy: From being the new tool on the block to steady state where Ben has to earn new Tuple customers Bullseye Framework: Derrick re-read his go-to startup guide to select StaticKit’s repeatable traction channels Tuple’s Q4 objectives and key results (OKRs): Fill top of funnel to increase new email subscribers and trials to continue to grow Ben’s future plans to gather marketing and sales information/intelligence by advertising and appearing on dev-related podcasts Design Matters: Impacts people’s perception of product and builds trust Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Using Tailwind CSS with Next.js (https://statickit.com/guides/next-js-tailwind)  Level (https://level.app/) Slack (https://slack.com/) Zoom (https://zoom.us/) Upcase by Thoughtbot (https://thoughtbot.com/upcase) Traction: A Startup Guide to Getting Customers by Gabriel Weinberg and Justin Mares (https://www.amazon.com/Traction-Startup-Guide-Getting-Customers/dp/0976339609)  Ruby on Rails (https://rubyonrails.org) HubSpot (https://www.hubspot.com) Rob Walling (https://robwalling.com/) Drip (https://www.drip.com/) Adam Wathan (https://adamwathan.me/) Full Stack Radio (http://www.fullstackradio.com/) Syntax.fm (https://syntax.fm) Steve Schoger (https://www.steveschoger.com/) Elixir (https://elixir-lang.org) Recurly (https://recurly.com) Chargify (https://www.chargify.com)

10 October 2019


105: Exploring Freemium

105: Exploring Freemium

Ben is living his best life with walks on the beach and wonderful weather. On the Tuple side, he shipped some code, got a pull request (PR) merged, and is now on the devise authentication gem. Derrick’s been busy, too. StaticKit’s official integration with ZEIT went live. ZEIT is one of two major hosting providers in the static site ecosystem. Also, an initiative with Zapier is in the works. Today’s Topics Include: Derrick did it his way: Integrations can be a powerful marketing channel Zapier Integration: Derrick’s waiting on approval to be listed publicly in its directory Positive Pace: Derrick invests his previous product efforts with marketing impact Pricing Pros and Cons: Free vs. paid tiers for forms or submissions per Website Personal Response: Derrick receives notification when someone new signs up with StaticKit to offer support Derrick joined TinySeed, a startup accelerator that helps bootstrappers grow their company faster through funds Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Using Tailwind CSS with Next.js (https://statickit.com/guides/next-js-tailwind)  Level (https://level.app/) Devise Authentication Gem (https://rubygems.org/gems/devise/versions/4.2.0) ZEIT (https://zeit.co/) Zapier (https://zapier.com/) Netlify (https://www.netlify.com/) FormKeep (https://formkeep.com) Salesforce (https://www.salesforce.com/) Slack (https://slack.com/) Adam Wathan (https://adamwathan.me/) Superhuman (https://superhuman.com/) Drip (https://www.drip.com/) TinySeed (https://tinyseed.com/) JAMstack Conf (https://jamstackconf.com)

3 October 2019


104: Tiny Conferences, and Business Growth Challenges

104: Tiny Conferences, and Business Growth Challenges

Ben is finding it easier to plan meetings to talk about challenges, and how he appreciates consistency. He describes his recent experiences with NanoConf and TupleConf. Derrick understands how perspectives shift as a business goes through different stages. Everyone wants financial security, but they always have complicated problems to solve. Today’s Topics Include: Mini Mastermind Conferences: Growth Strategy for building rapport and trust while bringing in new people for new perspectives Lessons Learned: Capture what went well, what should change in the future TupleConf: Ben, Joel, and Spencer discussed high-level questions and risk of co-founder issues and ambitions How to Deal with Conflict: Know your strengths, weaknesses, and personality type Planning and Prioritization: How to clarify and activate energy to do lower/smaller tasks StaticKit Milestones: Derrick achieved expansion revenue, additional customers, and annual renewals Pricing Structure, Tiers, and Upgrades: Monthly vs.yearly subscriptions with no surprises Derrick shares future vision of StaticKit beyond static forms for positive user experience Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Using Tailwind CSS with Next.js (https://statickit.com/guides/next-js-tailwind)  Level (https://level.app/) Big Snow Tiny Conf (https://bigsnowtinyconf.com) Build Your SaaS Podcast (https://saas.transistor.fm) CartHook (https://carthook.com) Brian Casel (https://briancasel.com/) WordPress (https://wordpress.com/) Gatsby (https://www.gatsbyjs.org/) Jekyll (https://jekyllrb.com/) Drip (https://www.drip.com/) Netlify (https://www.netlify.com/) Stripe (https://stripe.com/) GitHub (https://github.com/)

26 September 2019


103: Code Quality and Balancing TDD

103: Code Quality and Balancing TDD

Ben’s been adding variety to work by biking to breakfast and the beach, while working in-between during his stay on Martha’s Vineyard. He’s feeling lucky to work remotely, and still be able to connect with co-founders! Derrick enjoys a change of scenery from time-to-time during workdays, especially to kickstart his blood flow during an afternoon lull or breaking point. Today’s Topics Include: Writing code is like riding a bike: Tuple moving forward with adding single sign-on Caring about Code Quality: Ben’s higher level tests prove more valuable, less coupled Evolution of Testing: Derrick’s progress from test-driven development (TTD) to practical testing for StaticKit’s structure and features Devise Deal Breaker: Digested passwords in Tuple database wouldn’t need to be reset Pair programming proves powerful in preventing mistakes and being blocked Marketer? Developer? Sales? Ben’s possible future role and responsibilities with Tuple Hockeystick Metrics: First-paying StaticKit customer leads to 200% growth increase Content Marketing: Using Tailwind CSS with Next.js spikes StaticKit sign ups Self-serve Engine: Easily upgrade and deploy StaticKit from sandbox to live mode Prioritize Priorities: Ben encourages Derrick to focus on forms for StaticKit AoP Podcast: Is fanbase willing to pay for extra-special content? Share ideas with Ben and Derrick via Twitter Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Using Tailwind CSS with Next.js (https://statickit.com/guides/next-js-tailwind)  Level (https://level.app/) AoP Episode 22: Finishing the Year Strong (https://artofproductpodcast.com/episode-22) Tailwind CSS (https://tailwindcss.com/) Next.js (https://nextjs.org/) Rob Walling (https://robwalling.com/) Drip (https://www.drip.com/) Security Assertion Markup Language (SAML) (https://searchsecurity.techtarget.com) Ruby on Rails (https://rubyonrails.org) Thoughtbot (https://thoughtbot.com) RubyGems (https://rubygems.org) Devise (https://github.com/plataformatec/devise) DigitalOcean (https://www.digitalocean.com/) JSON (https://www.json.org/)

12 September 2019


102: Single Sign On (SSO) for Tuple?

102: Single Sign On (SSO) for Tuple?

The true life of an entrepreneur! From backgrounds to beards, change is in the air for both Ben and Derrick. Ben is a 36-year-old man who is back living with his parents temporarily to save some cash. Ben considered himself a minimalist, until he realized just how much stuff he had to move. So, he hired movers. Derrick describes the importance of documenting lessons learned and accumulating knowledge. As a result, he got his first paying customer for StaticKit. A meager $10 in revenue is greater than zero. Today’s Topics Include: Tuple: All for One, or One for All? Ben seeks advice on whether to make significant changes to app to satisfy single prospect that requires single sign-on (SSO) support Authentication and Security Schemes: Increasing scope intimidates and impacts legacy engineering decisions Big Decisions equal Big Bucks: Good but challenging problem to have in business Free to paid options for Derrick’s StaticKit turns into inflexible data model Got one, get more: Freemium customer converts to first StaticKit paid subscriber Derrick’s Next Step with StaticKit: Default state of being sustainable and breaking even on personal expenses Solo Founder: Tricky to find good fit of founder to do everything and grow quickly Keep Shipping Away: Set weekly goals to achieve and celebrate wins Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Level (https://level.app/) G Suite (https://gsuite.google.com) Security Assertion Markup Language (SAML) (https://searchsecurity.techtarget.com) Basecamp Shape Up (https://basecamp.com/shapeup) Thoughtbot (https://thoughtbot.com) RubyGems (https://rubygems.org) Ruby on Rails (https://rubyonrails.org) Drip (https://www.drip.com/) Stripe (https://stripe.com) React (https://reactjs.org)

5 September 2019


101: Mentorship Momentum with Matt Wensing of SimSaaS

101: Mentorship Momentum with Matt Wensing of SimSaaS

While Ben’s on vacation, Derrick welcomes Matt Wensing, founder of SimSaaS and co-host of the Out of Beta podcast. Matt was also the co-founder and CEO of Stormpulse. Derrick credits Matt for giving him great advice to make the winding down of Level less daunting. Now, Derrick’s on the upswing of rebuilding his confidence, despite challenging cluster headaches and stress cannibalising productivity. Today’s Topics Include: Out of Beta: Matt’s new podcast where he publicly discusses projects and products Mentorship Momentum: Seek help to sharpen software as a service (SaaS) skills Matt’s focused on marketing efforts to get work done and sales to gain access What is launching? Get started for free! TinySeed, Big Benefits: Solo business can’t do it alone; community plays a big role Fruitful Conversations: StaticKit update involves JavaScript, APIs, and Markup (JAMStack) Links and resources: Matt Wensing on Twitter (https://twitter.com/mattwensing) Matt Wensing on LinkedIn (https://www.linkedin.com/in/wensing) SimSaaS (https://simsaas.co) Riskpulse (https://riskpulse.com/) Out of Beta Podcast (https://outofbeta.fm) Stormpulse (https://stormpulse.com) SimSaaS on TinySeed (https://tinyseed.com/latest/2019-funding-announcement-simsaas) MicroConf (https://www.microconf.com) MicroConf Europe (https://microconfeurope.com) Brian Casel (https://briancasel.com/) Rob Walling (https://robwalling.com/) Jason Cohen (http://blog.asmartbear.com/jason-cohen) Company of One by Paul Jarvis (https://ofone.co/) Slack (https://slack.com/) Heroku (https://www.heroku.com/) CI/CD for WordPress with Peter Suhm of Branch CI (https://webmasterradio.fm/episode/ci-cd-for-wordpress-with-peter-suhm-of-branch-ci) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto)

29 August 2019


100: A Cool 100th Episode: Celebrating With Our Past Guests

100: A Cool 100th Episode: Celebrating With Our Past Guests

One of the benefits of having a podcast is being able to interview interesting people. Being a podcast guest is the best gig in the universe. Spew some knowledge, or just ramble. It’s time to celebrate the 100th episode of the Art of Product (AoP) podcast by catching up with previous guests to share updates and what’s next. Thanks for listening! Today’s Topics Include: Julian Shapiro: Running the growth agency, Bell Curve, was not rewarding but stressful; pivoted to Demand Curve to offer training to grow companies and teams Jason Cohen: Busy because of WP Engine’s multiple acquisitions, including buying Flywheel; he describes how acquisition accelerates or de-risks successful strategies Rob Walling: TinySeed continues to thrive and fun to work with ambitious and motivated founders building things; MicroConf moves from Vegas to Minneapolis in April 2020 Paul Jarvis: Re-recording videos and audio for MailChimp course and rebuilding Fathom Rahul Vohra: Superhuman achieved Series B and added employees; working on mental health and wellness by getting a super-sweet and super-dependent puppy Steve Schoger: Recycled redesigned Tuple site at Laracon and now working on Tailwind UI with Adam Wathan Links and resources: AoP Episode 61: Unconventional Growth Tactics with Julian Shapiro (https://artofproductpodcast.com/episode-61) Julian Shapiro (https://www.julian.com) Demand Curve (https://www.demandcurve.com/) Bell Curve (https://www.bellcurve.com/) Y Combinator (https://www.ycombinator.com/) AoP Episode 69: Sound, Actionable Advice with Jason Cohen  (https://artofproductpodcast.com/episode-69) WP Engine (https://wpengine.com/) Flywheel (https://getflywheel.com/flywheel-is-joining-wpengine) Jason Cohen - Designing the Ideal Bootstrapped Business (https://vimeo.com/74338272) SmartBear (https://smartbear.com/) A Smart Bear Blog (https://blog.asmartbear.com/) AoP Episode 66: TinySeed Updates with Rob Walling (https://artofproductpodcast.com/episode-66)  Rob Walling (https://robwalling.com/) TinySeed (https://tinyseed.com/) Startups for the Rest of Us (https://www.startupsfortherestofus.com/) MicroConf (https://www.microconf.com/) Out of Beta Podcast: The first TinySeed founder retreat  (https://player.fm/series/out-of-beta-2517215/the-first-tinyseed-founder-retreat) AoP Episode 93: Company of One with Paul Jarvis (https://artofproductpodcast.com/episode-93) Paul Jarvis (https://pjrvs.com/) Company of One (https://ofone.co/) MailChimp Course (https://pjrvs.com/wordpress-course/mailchimp/) Fathom (https://usefathom.com/) Camtasia (https://www.techsmith.com/video-editor.html) AoP Episode 91: Feeling Superhuman with Rahul Vohra (https://artofproductpodcast.com/episode-91) Superhuman (https://superhuman.com/) Headway (http://headwaythemes.com/) AoP Episode 70: Refactoring UI: Concept to Launch  (https://artofproductpodcast.com/episode-70) Steve Schoger - Refactoring UI: Tuple (https://www.youtube.com/watch?v=RC9cYdbQ-_c)    Laracon (https://laracon.net/) Justin Jackson’s Transistor (https://justinjackson.ca/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto)

22 August 2019


99: The Binge Is Real, Countdown to the 100th Episode

99: The Binge Is Real, Countdown to the 100th Episode

There’s no need to ask them who they are, what they do, businesses and products they built because listeners know them through their stories. After a lot of random, but worthwhile conversations, they’re getting good at being podcast co-hosts. How long does it take to listen to all episodes of Ben and Derrick’s Art of Product (AoP) podcast? Who knew it would be binge-worthy? One more down, one to go before they reach Episode 100! Today’s Topics Include: Tuple 1.0: App is available, despite instant self-serve checkout setback Tuple customers are expanding their use, but there’s still room for more users One-time lump sum: Tuple pricing model that makes sense StaticKit Beta: Start small with kernel of a product to keep funnel constrained Marketing Research and Product Risk: StaticKit to stand on its own or grow Drip and Deleted Emails: Save copies to maintain confidence in critical path Negative Churn: Influence users to upgrade pricing for expansion revenue Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto) Giant Robots Podcast (https://giantrobots.fm/) Steve Schoger (https://www.steveschoger.com/) Userlist  (https://userlist.io/) Adam Wathan on Twitter (https://twitter.com/adamwathan) Tailwind CSS (https://tailwindcss.com/) Product Hunt (https://www.producthunt.com/) Ray Ozzie (https://www.linkedin.com/in/rayozzie) WordPress (https://wordpress.com/) Drip (https://www.drip.com/) Refactoring Rails (https://www.refactoringrails.io/)

15 August 2019


98: Adam Covers for Derrick

98: Adam Covers for Derrick

Derrick’s short notice about not co-hosting this episode because of being on a plane, and Ben not knowing or planning what to discuss, who and what’s left? Updates and reports on Tuple and Tailwind. Welcome back Adam Wathan! Today’s Topics Include: Today’s Trend: Advisor/investor/founder journals and reports of accomplishments Serves as a way to stay in touch, build relationships, ask questions, and get feedback Three Tuple Reports Later: Things are still going good Programming meets Business: Gary Bernhardt commits to being future podcast guest Successful Tuple Shipments: Significant use of Webcam feature Pricing Options: Ben expresses concern over free trials or pre-paid plans to capture credit cards and emails Invite-only vs. Public Launch: Continue as is, or open Tuple up to all Tuple Update: Revenue is growing quickly, receiving 70-100 support tickets weekly, and room to add customers Tailwind Update: Adam launched first set of videos for Tailwind CSS course Tailwind Subscription/Price Structure: Yet to be determined Adam’s Prediction: Education and documentation determine open source winner Links and resources: Adam Wathan on Twitter (https://twitter.com/adamwathan) Full Stack Radio (http://www.fullstackradio.com/) Tailwind CSS (https://tailwindcss.com/) Refactoring UI by Adam Wathan and Steve Schoger (https://refactoringui.com/) Steve Schoger (https://www.steveschoger.com/) Tyler Tringas on Twitter (https://twitter.com/tylertringas?lang=en) Brian Casel (https://briancasel.com/) Gary Bernhardt on Twitter (https://twitter.com/garybernhardt) ExecuteProgram.com (https://www.executeprogram.com/) David Heinemeier Hansson (DHH) on Twitter (https://twitter.com/dhh) Giant Robots Episode 26: Deep into the psyche of Gary Bernhardt (https://giantrobots.fm/episodes/26) Giant Robots Episode 27: Fabulous new mistakes with Joe Ferris (https://giantrobots.fm/episodes/27) Giant Robots Episode 28: Farther, further, faster with David Heinemeier Hansson (https://giantrobots.fm/episodes/28) Node.js (https://nodejs.org/) React (https://reactjs.org/) Ruby on Rails (https://rubyonrails.org/) Zoom (https://zoom.us/) Superhuman (https://superhuman.com/) Screenhero (https://screenhero.com/) Slack (https://slack.com/) GitHub (https://github.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto)

8 August 2019


97: To Build, or Not to Build - Jane Portman of Userlist

97: To Build, or Not to Build - Jane Portman of Userlist

While Ben’s on vacation, Derrick welcomes another podcast host who can commiserate with him about email automation. Jane Portman is a UI/UX expert and consultant who hosts the UI Breakfast Podcast and co-founded Userlist.io. She describes what it takes to create a customer messaging tool. Today’s Topics Include: Product Priorities: Slow, steady, and quality Lifestyle Business: Overall goal is to replace consulting with SaaS recurring revenue Challenges: Limited development time and resources; slow growth rate to adopt mission-critical product To Build, or Not to Build: Avoid feature creep by focusing on what to add or improve Playbook Post: 10 steps to successfully position a product Launch Process: People are waiting for the right time for the right tool for their business Customer Conversations: Pre-product interviews about problem to be solved; followed by product demos to grant access to beta version for feedback Finding Customers: Landing page, updates, stories, sign-ups, mailing list, and more We’re out of Beta! Simple and straight-forward product launch plan and strategy Generic Illustrations: Product design trend that has to end Email Experiences: Educate people on how to ethically use email to serve their business Links and resources: User Onboarding: The Ultimate Guide for SaaS Founders (https://userlist.com/user-onboarding/) UI Breakfast Podcast (https://uibreakfast.com) Userlist.io (http://userlist.io/) UI Breakfast on Twitter (https://twitter.com/uibreakfast) Userlist.io on Twitter (https://www.twitter.com/Userlistio) Behind the Scenes of Our Upcoming Public Launch (https://userlist.io/launch-strategy/) How We Used April Dunford’s 10-Step Method to Overhaul Positioning at Userlist (https://userlist.io/positioning-overhaul/) AoP Episode 91: Feeling Superhuman with Rahul Vohra (https://artofproductpodcast.com/episode-91) Product Hunt (https://www.producthunt.com/) Hacker News (https://news.ycombinator.com/) Drip (https://www.drip.com/) MailChimp (https://mailchimp.com/) Humans of Flat Design on Twitter (https://twitter.com/humansofflat?lang=en)  Paul Jarvis (https://pjrvs.com/) MicroConf (https://www.microconf.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto)

1 August 2019


96: Tuple Official Launch and Taking Time to Unplug

96: Tuple Official Launch and Taking Time to Unplug

Is something bugging you? Need to get away from everything? Derrick can’t wait to once again ride rugged waters on Minnesota’s many lakes. Not unlike startups, it isn’t always easy to stay afloat when under pressure. Heeelllloooo! Are you there? Still interested? Ask and you shall receive. Ben shipped a major feature for Tuple. Drumroll please…video support. I’ll Tuple you! Today’s Topics Include: Sensible Deprivation: Some suffering can be good; makes you appreciate things more Get Over It, and Gain Confidence: Design and develop video support prototype Official Launch Date for Tuple: Some time in August; Ben’s still trying to shake the perception he’s charging people for beta product Security Vulnerabilities Happen: Ben’s reaction to recent issues with Zoom and Slack Mistakes Ben Might Make: Free Tuple trial to increase conversion and expansion Derrick’s Building Product: Initial version of StaticKit and form collection component Security ROI: Short-circuiting pushback with strong write-up for SOC 2 and ISO 27001 3+ Tuple team? Someday, Ben wants to hire a part-time designer and developer Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto) Outward Bound (https://www.outwardbound.org) Zoom (https://zoom.us/) Superhuman (https://superhuman.com/) Slack (https://slack.com/) Adam Watham (https://adamwathan.me/) Steve Schoger (https://twitter.com/steveschoger?lang=en) Laracon (http://laracon.us/) Elm (https://elm-lang.org/) React (https://reactjs.org/) Jekyll (https://jekyllrb.com/) Drip (https://www.drip.com) IS0 27001 (https://www.iso.org/isoiec-27001-information-security.html) SOC 2 (https://www.ssae-16.com/soc-2/) HackerOne (https://www.hackerone.com/)

25 July 2019


95: What Really Happened to Screenhero

95: What Really Happened to Screenhero

While Derrick is away, Ben welcomes Don Goodman-Wilson, who was the first hire at Screenhero in 2013. Don shares his version of Screenhero’s incredible journey, its migration to Slack, and Tuple coming to the rescue. Better late than never! Today’s Topics Include: Work Ethic/Culture: Doctorate in philosophy requires logic and dedication Engineering Challenges: Learning low-level C/C++ code in Screenhero product Microsoft Windows and Apple Mac: Harmonizing code bases Web Application Programming: User interface (UI), reliability, latency, quality, and billing Product/Market Fit: Quick growth, adoption, and implementation of Screenhero Pair Programming: Personal and professional sharing and collaboration Second Day at First Expo: Atlassian’s interest, followed by Slack’s acquisition Platform of Choice: Who’s the best partner to work with to achieve Screenhero’s goals? In and Out of the Sandbox: Screenhero’s prone to crashing and uses private APIs Slack destroyed Screenhero: Expectations and compromises created culture clash Heartbreaking, Rational Reality: Removal of remote screen control in Slack calls Maintainerati’s Mission: Understand challenges and offer solutions for maintaining open source software Links and resources: Don Goodman-Wilson (https://don.goodman-wilson.com/)  Don Goodman-Wilson on LinkedIn (https://www.linkedin.com/in/degoodmanwilson) Maintainerati (https://maintainerati.org) Screenhero (https://screenhero.com/) Y Combinator (https://www.ycombinator.com/) Slack (https://slack.com) The Screenhero Story - The Screenhero Blog (https://blog.screenhero.com/post/109339022326/the-screenhero-story) Removal of remote screen control in Slack calls (https://get.slack.help/hc/en-us/articles/360022908874-Removal-of-remote-screen-control-in-Slack-calls) Atlassian (https://www.atlassian.com/) HipChat (https://www.atlassian.com/partnerships/slack) WebRTC (https://webrtc.org/) Redis (https://redis.io/) Python (https://www.python.org/) Stripe (https://stripe.com/) Ractive.js (https://ractive.js.org/) Ruby-Grape Rack (https://github.com/ruby-grape/grape) Ruby on Rails (https://rubyonrails.org/) Dropbox (https://www.dropbox.com/) Google Hangouts (https://tools.google.com/dlpage/hangoutplugin) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Maintainerati on Twitter (https://twitter.com/Maintainerati) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) StaticKit (https://www.statickit.com/) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto)

11 July 2019


94: Seeking Clarity

94: Seeking Clarity

Summer is in full swing. Ben spent a fun and productive day talking about work at a Red Sox game. It was an own-your-own business startup moment. Derrick can see clearly now, thanks to SMILE laser eye surgery. But he’s still seeking clarity on whether to make the masses happy, or stick to core concerns to attract specific customers when creating a new product. Today’s Topics Include: Tuple Grows Up: New version of marketing site getting ready to launch Cha Ching: Confirmation of biggest single Tuple invoice sent for payment How much wisdom is there in the crowd? Can you trust it? Remote Control: Tuple customers give up control to use driver/navigator pairing Self-serve Sign-up: Tuple strives for automation, learning, and feedback Time for a Truce: Trash talking, name calling stops for Slack to send customers to Tuple Soon to be released: Derrick’s StaticKit, a modern approach for embedding dynamic forms onto static sites Links and resources: StaticKit (https://www.statickit.com/) Art of Product Podcast Episode 91: Feeling Superhuman with Rahul Vohra (https://artofproductpodcast.com/episode-91) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto) Jekyll (https://jekyllrb.com/) Middleman (https://middlemanapp.com/) Gatsby (https://www.gatsbyjs.org/) Hugo (https://gohugo.io/) Next (https://nextjs.org/) React (https://reactjs.org/) Superhuman Product-Market Fit Survey (https://www.slideshare.net/marklittlewood/rahul-vohra-founderceo-superhuman-the-productmarket-fit-engine-122102118) Drip (https://www.drip.com/) Steve Schoger (https://www.steveschoger.com/) Stripe (https://stripe.com/) MicroConf (https://www.microconf.com/) Slack (https://slack.com/) Removal of remote screen control in Slack calls (https://get.slack.help/hc/en-us/articles/360022908874-Removal-of-remote-screen-control-in-Slack-calls) Screenhero (https://screenhero.com/) Netlify (https://www.netlify.com/) Zeit (https://zeit.co/) Mailchimp (https://mailchimp.com/) ConvertKit (https://convertkit.com/) JSON (https://www.json.org/) Zapier (https://zapier.com/) FormKeep (https://formkeep.com/) Heroku (https://www.heroku.com/) Ruby on Rails (https://rubyonrails.org/) Medium (https://medium.com/) Phoenix (https://phoenixframework.org/)

4 July 2019


93: Company of One with Paul Jarvis

93: Company of One with Paul Jarvis

After a QuickTime error eradicated Paul Jarvis’s conversation with Ben and Derrick for an Art of Product episode, he’s back with an update on his recently published book, Company of One. Should Paul strike while the iron is hot? Despite the book’s success and being encouraged to write another one, Paul wants to take a necessary break before proposing a new book idea. Today’s Topics Include: Legally Binding Thumbs-up Emoji: How Paul sold rights for book to be in 13 languages Break between Building: Frustration of figuring things out, replaced with hammock thinking and relaxation Paul’s writing process fills fountain of ideas; ready to do a book on digital privacy Slack Support Group: Help yourself and others Level Failure Leads to Filtering Idea Criteria: Shouldn’t be mission-critical product; require more than a few decision makers; and native apps shouldn’t be a minimum requirement Company of One: Doesn’t necessarily refer to one person, but mindset Balance between technology you know and learning curve for something you don’t Software as a Service (SaaS) Business: Scale up or stay small? Derrick describes Company of One as what he aspires toward, but is open to possibility of co-founders Nothing Lasts Forever: Question growth, not stagnation Seek and scale support, especially when using third-party software Drumroll, Please: Ben announced plans for public launch of Tuple in August 2019 Links and resources: Paul Jarvis (https://pjrvs.com/) Company of One (https://ofone.co/) Company of One (Co1) Academy (https://ofone.co/learn/) Company of One Podcast (https://ofone.co/company-of-one-podcast/) Fathom (https://usefathom.com/) Paul Jarvis on Twitter (https://twitter.com/pjrvs/) Paul Jarvis’s WPComplete Plugin (https://wpcomplete.co/) Ingenx (https://www.ingenxtec.com/) The Year of Living Biblically by A.J. Jacobs (https://ajjacobs.com/books/the-year-of-living-biblically/) Slack (https://slack.com/) Screenhero (https://screenhero.com/) Rob Walling (https://robwalling.com/) Drip (https://www.drip.com/) Finding My Next Bootstrapped Business Idea (https://www.derrickreimer.com/essays/2019/05/28/finding-my-next-bootstrapped-business-idea.html) DigitalOcean (https://www.digitalocean.com/) Heroku (https://www.heroku.com/) Ruby on Rails (https://rubyonrails.org/) Phoenix (https://phoenixframework.org/) Superhuman (https://superhuman.com/) Hacker News (https://news.ycombinator.com/) Art of Product Podcast Episode 91: Feeling Superhuman with Rahul Vohra (https://artofproductpodcast.com/episode-91) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto)

27 June 2019


92: Slack Leaves the Market

92: Slack Leaves the Market

The world received amazing news in the form of a great gift: Slack is making a major change in the market—it’s leaving! Ben and Derrick share their thoughts on Slack’s reasonable and rational decision to remove remote control functionality. What happens now? Try Tuple! Just sayin’, actually that’s what Tuple customers are suggesting. Today’s Topics Include: Improve Slack Calls: Reason for removing rarely used remote control feature Kicking marketing machine into gear: Customers’ kind words generated surge in requests for access to Tuple Slack and Screenhero Saga: Complete story of acquisition and pair programming will probably never be told Keep shipping, swinging, and taking shots by increasing luck surface area and learning from previous successes and failures Dear Dvorak user, is it time to switch? Tuple’s shipping international keyboard support Big deals keep coming in for Ben; it’s great to sometimes say, “No” Derrick’s writing cadence continues; flattered by onslaught of positivity from people Product/Founder Fit: Be passionate about product or business before building it Pressure to be Perfect: Don’t sweat the small stuff, just the details Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Just Keep Shipping by Derrick Reimer (https://www.derrickreimer.com/essays/2019/05/31/just-keep-shipping.html) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Slack (https://slack.com/) Removal of remote screen control in Slack calls (https://get.slack.help/hc/en-us/articles/360022908874-Removal-of-remote-screen-control-in-Slack-calls) Screenhero (https://screenhero.com/) Drip (https://www.drip.com/) Zoom (https://zoom.us/) GitHub (https://github.com/) The Dvorak Keyboard (https://www.dvorak-keyboard.com/) Adam Watham (https://adamwathan.me/)

20 June 2019


91: Feeling Superhuman with Rahul Vohra

91: Feeling Superhuman with Rahul Vohra

Derrick’s feeling “superhuman.” Fortunately, he’s a user and lover of the Superhuman product. Maybe that’s why today’s guest is Rahul Vohra, co-founder and CEO of Superhuman. Today’s Topics Include: Reason for Superhuman still being invite-only is not to increase user demand Sustainable Word-of-Mouth Growth Engine: If you don’t pick the users, you can’t responsibly work on their feedback Purpose of Product and Target Audience: Email is work, and work is email; designed to be meaningful and life changing for high-volume email senders Startup Details: Deliberately think through and consider everything deeply from scratch Don’t turn down money when bootstrapping to find perfect product market/customer fit Knack for knowing what people want, before they know they want something; and helping people realize they want something Without active or spending money on marketing, Superhuman’s waitlist keeps growing Superhuman’s Values: Create delight, be intentional, and remarkable quality Best founders, including Rahul, are unstoppable forces of nature; they leave debris and destruction in their wake Time tracking a day in the life of Rahul: 40% managery; 20% recruiting; 14% fundraising; and 11% product, community engagement, and deep thoughts Superhuman’s pricing is low, but generates high value; big fan of round numbers Business and product metrics: Activation, seat churn, net dollar churn, speed, and reliability rates Objective: Refine entire Superhuman experience to exhibit remarkable levels of quality through three key results - ARR, hiring, and product sentiment Generate roadmap and find balance to maintain lead over market and continue to grow Startup Growth: Pick weekly growth rate; you don’t have to grow faster than you want to Links and resources: Superhuman (https://superhuman.com/) Rahul Vohra on LinkedIn (https://www.linkedin.com/in/rahulvohra) Rahul Vohra on Twitter (https://twitter.com/rahulvohra) Rahul Vohra’s Email (mailto:rahul@superhuman.com) Superhuman Product-Market Fit Survey (https://www.slideshare.net/marklittlewood/rahul-vohra-founderceo-superhuman-the-productmarket-fit-engine-122102118) Rahul Vohra on This Week in Startups with Jason McCabe Calacanis (https://www.facebook.com/jasoncalacanis/videos/2299819313590909/) Rapportive (http://www.rapportive.com/) TechCrunch (https://techcrunch.com/) Product Hunt (https://www.producthunt.com/) Hacker News (https://news.ycombinator.com/) Google Docs (https://www.google.com/docs/about/) GitHub (https://github.com/) Startup = Growth - Paul Graham (http://www.paulgraham.com/growth.html) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto) Tuple (https://tuple.app/)

13 June 2019


90: The Mom Test with Rob Fitzpatrick

90: The Mom Test with Rob Fitzpatrick

Ben and Derrick welcome Rob Fitzpatrick, author of The Mom Test: How to talk to customers and learn if your business is a good idea when everyone is lying to you. It’s not your typical non-fiction business book, but short and straight to the point. It should be a mandatory prerequisite for anyone embarking on the startup journey. Derrick’s Level Retrospective describes how Rob’s book had a major impact on his most recent startup experience. People want to be supportive, so it’s difficult to get unbiased feedback during customer validation. Derrick already knew this to be correct, but underestimated the degree to which everyone lies. So, he felt betrayed by early validation efforts proved to be radically different from reality. Today’s Topics Include: Don’t ask anyone if your business is a good idea because everyone is biased Burden of truth should be put on yourself, not your customers Entrepreneur’s Superpower: Getting support before it’s deserved because passion pollutes feedback Founder Fit: Does your business idea merge with your product and lifestyle goals? Founder Centric: Cashflow-positive education and training agency for startups Product-Market Fit: People share their problems via a proposed solution; when customers send feature requests, get to root of the problem Statistical significance of sample size is a trap; reach point of diminishing returns to move forward with product, and focus on number of/hours spent on conversations Entrepreneurs and customers think every problem matters, but they don’t What to do next to pivot in the right direction and niche down Links and resources: The Mom Test by Rob Fitzpatrick (https://www.amazon.com/Mom-Test-customers-business-everyone/dp/1492180742) Rob Fitzpatrick (https://robfitz.com/) The Workshop Survival by Rob Fitzpatrick (https://www.workshopsurvival.com/) Founder Centric (http://www.foundercentric.com/) Steve Blank (https://steveblank.com/) Paul Graham (http://www.paulgraham.com/) Skype (https://www.skype.com/en/) Slack (https://slack.com/) Hacker News (https://news.ycombinator.com/) Superhuman Product-Market Fit Survey (https://www.slideshare.net/marklittlewood/rahul-vohra-founderceo-superhuman-the-productmarket-fit-engine-122102118) Songkick (https://www.songkick.com/) Spin Selling by Neil Rackham (https://www.amazon.com/Neil-Rackham/e/B000APLFJK/ref=dp_byline_cont_ebooks_1) Drip (https://www.drip.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Level Retrospective (https://www.derrickreimer.com/essays/2019/05/17/im-walking-away-from-the-product-i-spent-a-year-building.html) Level Manifesto (https://level.app/manifesto) Tuple (https://tuple.app/)

30 May 2019


89: Go Big, or Stay Small?

89: Go Big, or Stay Small?

Ben announced a medium-sized step forward for Tuple. A bug where the video portion would freeze at the start of or during a call was replicated and resolved. It was a double bonus: Fixed the bug and made the Tuple app faster. Derrick’s contemplative mode continued as he tried to figure out the future of Level. He retreated to think and disconnect. He sought clarity on what to do and is confident that he has made the best decision. Today’s Topics Include: Dynamic Duos: Problem solving doesn’t require understanding of programming language Fear not! Tuple continues to consistently update dependencies and perform QA Tuple’s dashboard of latest version of call quality rating is highest so far Story of Level: How it started; goals, processes, and mistakes made; and what resources are available or needed to make it sustainable and successful Derrick’s Decision: Not the right path for him to be on, so it’s the end of the road for Level Go big, or stay small? Launch something valuable that you can charge your market for, then you can expand from there Product Market Founder Fit: Is the business the way you want to shape your life? Do No Disturb Derrick: Convinced to cultivate a capability to slow down and carry on Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) Drip (https://www.drip.com/) Ruby (https://www.ruby-lang.org/en/) Zoom (https://zoom.us/) WebRTC (https://webrtc.org/) Company of One by Paul Jarvis (https://ofone.co/) Rob Walling’s Stairstep Approach to Bootstrapping (https://robwalling.com/2015/03/26/the-stairstep-approach-to-bootstrapping/) Superhuman Product Market Fit Survey (https://www.slideshare.net/marklittlewood/rahul-vohra-founderceo-superhuman-the-productmarket-fit-engine-122102118)

23 May 2019


88: Will They Make the Jump?

88: Will They Make the Jump?

Recently, Ben felt gloriously empty and described how nice it was to have nothing going on. In his stomach, that is. He successfully finished a 48-hour fast. It was difficult, but pleasurable. Now, he’s back to craving calories, eating, and work! Derrick had a challenging week with feelings of uncertainty. He invited more people to try Level, but got similar results. He fears that people may not progress with the product. Will people actually make the jump to Level? Today’s Topics Include: April showered Ben with 66 sign ups of paid trials for Tuple Magic Number is 3: Multiple developers mean Tuple will soon ship multiway calls feature Derrick’s going back to customer development roots to proactively learn and listen Tactical errors with validation to confirm assumptions about how to solve Slack problem Derrick’s envyable or dire position? Worst-case scenario and what’s next Startups fail, the struggle is real, and the pivot is time honored for a reason Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Derrick’s Level Manifesto (https://level.app/manifesto) Tuple (https://tuple.app/) The Mom Test by Rob Fitzpatrick (http://momtestbook.com/)

9 May 2019


87: Meta Podcasting

87: Meta Podcasting

Ben boldly admitted to doing a “weird” thing. He started listening to “us.” Not necessarily for quality control, but to spark his memory about topics Derrick and he talked about in previous AoP episodes. As a result, Ben’s become addicted to listening to people building companies podcasts. Unfortunately, there’s just not that many of them. Derrick also admitted to listening regularly to previous AoP episodes. But more so during the early days of the podcast, when he was apprehensive about his own ability on the microphone and wanted to find ways to improve. Today’s Topics Include: Cool Podcast with Cold Open: Hit “Play” and start talking Autophagy: Putting a twist-tie on snack cabinet sucks, but benefits your body and brain Tuple’s most requested feature: Multi-way calls Successful Meta-habit: Surveys serve as way to get feedback on product features Potential strategies for setting a launch date for Tuple Art of Building a Product and Company: Word-of-mouth, referrals, affiliate programs Derrick’s Level Launch: Warm email reminder to whet people’s appetite Mini-funnel Metrics for Level Launch: 500 given access to Level via email 70% open rate for email 182 created user account 41 created a team Onboarding Process for Level: Step 1: Create user account Step 2: Demo account is activated Fork in the Road: Optimize each phase and equip people to make it through funnel to get feedback on Level Derrick’s Top 2 Priorities for Level: Documentation and more manual outreach Derrick gets Ben “Pricing” Orenstein’s advice on who needs Level the most Derrick’s Plan for Level: Repeat, refine, and resend Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) The Art of Product: Episode 78 - Ultraworking with Sebastian Marshall (https://artofproductpodcast.com/episode-78) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) Derrick’s Level Manifesto (https://level.app/manifesto) Drip (https://www.drip.com/) 113: Justin Jackson - Growing Transistor to $10,000/month (http://www.fullstackradio.com/113) GitHub (https://github.com/) Clearbit (https://clearbit.com/)

2 May 2019


86: The Importance of Paying Customers in Product Feedback

86: The Importance of Paying Customers in Product Feedback

Ben had another good week. He signed up 25 new trials and about five conversions for Tuple. Are you one of the 500 chosen by Derrick to get access to Level? Be sure to check your Inbox on Monday for an email from him to find out. Also, Ben and Derrick welcome Adam Wathan as a co-host for this episode. Adam’s working on getting release 1.0 of Tailwind out the door with awesome documentation. Today’s Topics Include: Happiness vs. Harassment: Tuple’s paid trial process Will people pay for Level? Get free feedback first or make them pay upfront? Demo Option: Click around, view dummy posts to get sense of how Level works Refactoring UI: Could it be a perennial seller? How much should you share about your startup in your tweets? Focus on being best option; don’t brag about your success Trying to sell a theme via Tailwind; adding vs. creating new products Holy Grail of Software Business: Rob Walling’s stairstep approach to recurring revenue Growth rate required to stay alive? Keep product relevant to what market wants SaaS is definitely not all roses! Super Fast Email Services/Features: Snippets, Superhuman, Help Scout, and Shortcuts Links and resources: Adam Wathan on Twitter (https://twitter.com/adamwathan) Refactoring UI by Adam Wathan and Steve Schoger (https://refactoringui.com/) Steve Schoger (https://www.steveschoger.com/) Stripe (https://stripe.com/) Jason Cohen - Designing the Ideal Bootstrapped Business (https://vimeo.com/74338272) Perennial Seller: The Art of Making and Marketing Work that Lasts (https://www.amazon.com/Perennial-Seller-Making-Marketing-Lasts/dp/0143109014) MicroConf (https://www.microconf.com/) Tailwind CSS (https://tailwindcss.com/) Bootstrap (https://getbootstrap.com/) Justin Jackson Playing with Tailwind CSS (https://www.youtube.com/watch?v=TwUT0MmnrQw) Justin Jackson’s MegaMaker Club (https://megamaker.co/club/) Patreon (https://www.patreon.com/) Rob Walling’s Stairstep Approach to Bootstrapping (https://robwalling.com/2015/03/26/the-stairstep-approach-to-bootstrapping/) Upcase by Thoughtbot (https://thoughtbot.com/upcase) Paul Jarvis (https://pjrvs.com/) Heroku Dynos (https://www.heroku.com/dynos) Ruby on Rails (https://rubyonrails.org/) Elixir (https://elixir-lang.org/) Superhuman (https://superhuman.com/) Help Scout (https://www.helpscout.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/)

25 April 2019


85: The Hype Is Real

85: The Hype Is Real

The hype about Tuple is real! Ben’s been busy adding a bunch of new customers. He’s selling and delivering the dream. Derrick is back after mentally struggling in the midst of moving, which meant a week of zero productivity on Level. Now, he’s in a better place, mentally and literally. Today’s Topics Include: Ludicrous Mode: Full-resolution, uncompressed video stream option added to Tuple Tuple’s lack of scaling challenges due to peer-to-peer connections Tuple’s conversion rate for email list Ben’s “I’m bad at sales” email message and demo video Things to do and features to add in the future for Tuple Tuple achieves semi-milestone of customer renewals Ben’s fear of public availability to post Tuple’s pricing Bandwidth forces AoP podcast back to one episode per week Derrick ships fun and addictive emoji reactions feature in Level Inviting more people to increase Level’s sample size and address skepticism Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Heroku Dynos (https://www.heroku.com/dynos) Spaceballs (https://www.imdb.com/title/tt0094012/) Adam Wathan on Twitter (https://twitter.com/adamwathan/status/1115621251769225217) Ruby on Rails Action Cable Server (https://edgeguides.rubyonrails.org/action_cable_overview.html) Technical Debt - Our Approach to Building Cool Tech Profitably (https://founderquest.transistor.fm/episodes/technical-debt) Steve Schoger - Refactoring UI: Tuple (https://www.youtube.com/watch?v=RC9cYdbQ-_c)    Drip (https://www.drip.com/) Soapbox from Wistia (https://wistia.com/soapbox) Superhuman (https://superhuman.com/) Jason Fried (https://twitter.com/jasonfried)

18 April 2019


84: Developer Mindset with Brian Casel

84: Developer Mindset with Brian Casel

Who’s the mystery voice that only gets better as you listen to this episode? Actually, you’re probably already familiar with the work of the man behind the microphone. Derrick is busy moving to a new home, so Ben’s co-host is Brian Casel of BootstrappedWeb, ProcessKit, Audience Ops, and Sunrise KPI. Today’s Topics Include: Ben and Brian just got back from MicroConf; it’s an annual gathering of “all our people” Some talks were among their favorites, but others were mediocre and missed the mark Brian’s goal was to meet 5-10 new people doing interesting things, and reconnect and catch up with others he’s known for years Brian is an Art of Product (AoP) podcast listener and wants Ben and Derrick to not hold back, dig in, challenge each other, and ask more questions Are more people listening to Ben and Derrick’s podcast? Fireside metrics reveal that a lot of Tuple or Level customers come from listening to it More bootstrappers need to start a podcast and find friends to share ups and downs What happened when Ben pushed Brian to learn how to code? ProcessKit - best thing Brian’s built on the Web Phenomenon of how programmers love complexity ProcessKit pricing and customer research; Ben’s advice to get people to buy/use it Tuple Update: App is great; Ben’s been emailing list, and people are buying it Links and resources: Brian Casel (https://briancasel.com/) BootstrappedWeb Podcast (http://bootstrappedweb.com/) ProcessKit (https://processkit.com/) Brian Casel on Product Hunt (https://www.producthunt.com/@casjam) Audience Ops (https://audienceops.com/) Ops Calendar (https://opscalendar.com) Big Snow Tiny Conf (https://bigsnowtinyconf.com/) Sunrise KPI (https://betalist.com/startups/sunrise-kpi) Art of Product Podcast Episode 58 with Brian Casel: Evolving Roles as a Startup Founder (https://artofproductpodcast.com/episode-58) MicroConf (https://www.microconf.com/) MicroConf Recap (https://microconf.gen.co/) Chris Savage: How an Offer to Sell Wistia Inspired Us to Take On $17M in Debt (https://microconf.gen.co/chris-savage/) Jason Fried: Q+A with Jason Fried (https://microconf.gen.co/jason-fried/) Patrick Campbell: Pricing (https://microconf.gen.co/patrick-campbell-starter/) Joanna Wiebe: Money Words: Seven of the words and phrases we use most often in high-converting copy (https://microconf.gen.co/joanna-wiebe/) Fireside (https://fireside.fm/) Transistor (https://transistor.baremetrics.com/) Castos (https://castos.com/) Blubrry (https://create.blubrry.com) AJAX JavaScript (https://en.wikipedia.org/wiki/Ajax_(programming)) Tailwind CSS (https://tailwindcss.com/) Honeybadger (https://www.honeybadger.io/) React (https://reactjs.org/) Ruby on Rails (https://rubyonrails.org/) Vue.js (https://vuejs.org/) Stimulus JavaScript (https://stimulusjs.org/) Vanilla JavaScript (http://vanilla-js.com/) FollowUp.cc (https://followup.cc/) Superhuman (https://superhuman.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide)

11 April 2019


83: The Biggest Lever to Pull in Your Business

83: The Biggest Lever to Pull in Your Business

Ben and Derrick are back from MicroConf. There were plenty of solid talks and takeaways to help them think, theorize, and hypothesize about moving forward with their products. Also, Ben presented two Starter Edition sessions: Q & A with Rob Walling and Idea to Validation to Launch: The First 365 Days of Tuple. Today’s Topics Include: Ben stuck to plan of not going to many talks; made connections and socialized Growth-adjacent trend of not buying tickets to conference, but hanging out with others Ben crushed it when MCing Starter Edition; being part of conference at organization level MicroConf’s Unofficial Mantra: Charge more; pricing is powerful lever to pull for ROI, and businesses know they should do it, but don’t; if they do, it’s too small Tuple has stabilized, and it’s time to generate revenue; started emailing list Retro on financial situation; nothing to worry about yet, but not feeling rich Links and resources: MicroConf (https://www.microconf.com/) MicroConf Recap (https://microconf.gen.co/) Ben Orenstein at MicroConf (https://www.microconf.com/starter/speakers/ben-orenstein/) Honeybadger (https://www.honeybadger.io/) Wistia (https://wistia.com/) Jason Cohen (https://blog.asmartbear.com/) Hiten Shah (https://hitenism.com/) Chris Gimmer (https://chrisgimmer.com/) Ruby on Rails (https://rubyonrails.org/) Drip (https://www.drip.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/)

4 April 2019


82: Idea to Validation to Launch: MicroConf 2019

82: Idea to Validation to Launch: MicroConf 2019

Derrick and Ben have descended upon Las Vegas for MicroConf and an audience hungry for valuable tips on how to successfully start and grow a business. Ben will have two Starter Edition sessions: Q & A with Rob Walling and Idea to Validation to Launch: The First 365 Days of Tuple. Today’s Topics Include: MicroConf Goals: Connect with people, spend quality time with friends; don’t feel guilty or FOMO about not going to all talks Ben’s seeking a designer to replace super-successful Steve Schoger Optimism to Realism: Derrick’s shift in mindset about Level at 2018 vs. 2019 MicroConf Sharing wisdom and giving advice - all of the fun, and none of the hard work Not knowing what makes someone a good fit for Level; let people vote with their dollars Getting more founders into therapy to help their mental health Derrick’s mentor role for TinySeed: The Startup Accelerator Designed for Bootstrappers Tuple’s theme of recurring and expansion charges, but also one churn so far Links and resources: MicroConf (https://www.microconf.com/) Ben Orenstein at MicroConf (https://www.microconf.com/starter/speakers/ben-orenstein/) Rob Walling (https://robwalling.com/) Steve Schoger (https://www.steveschoger.com/) Drip (https://www.drip.com/) Sam Harris (https://samharris.org/) Wistia Soapbox (https://wistia.com/soapbox) TinySeed (https://tinyseed.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/)

28 March 2019


81: Sane and Sustainable Growth with Ben Curtis from Honeybadger

81: Sane and Sustainable Growth with Ben Curtis from Honeybadger

Derrick is still traveling. So, Ben’s co-host for this episode is Honeybadger Co-founder Ben Curtis. Honeybadger offers an application health monitoring tool featuring an easy-to-use platform with exception, uptime, and check-in monitoring. Since its creation about seven years ago, Honeybadger’s three founders - Curtis along with Starr Horne and Joshua Wood - cranked out all the work. However, the company added a marketing person a few months ago and recently hired its first developer. Today’s Topics Include: Honeybadger has kept headcount low to optimize profit-per-employee; eventually needed help with marketing and other tasks Downside of contractors is they’re not committed to being around for very long; wanted someone who was dedicated to making Honeybadger more successful Bringing new people in is risky, but Curtis kind of wishes they would’ve done it sooner Documenting processes is essential to transfer knowledge to new team members and discover opportunities for improvement and automation Setting expectations regarding time; Curtis makes conscious choice to only work 20-30 hours per week in Honeybadger’s relaxed and asynchronous office environment Honeybadger took about three years to achieve a stable infrastructure, where things weren’t regularly blowing up and breaking Moment Honeybadger Made It: Able to offer health insurance and living the dream by getting paid well to do exactly what they want to do and exactly how they want to do it What can you afford to pay yourself when starting a business? Establish schedule and roadmap to set goal to pay yourself regularly, even if amount is meager Honeybadger’s biggest costs are for hosting, health insurance, and salaries; company has grown through word-of-mouth, not paid marketing and advertising Gorilla Marketing: Free marketing and fantastic response rate for Honeybadger’s T-shirt giveaway to get customers’ credit card numbers; Burger Bus was also a success Be authentic to create brand recognition; you’re your target audience - what do you like? Honeybadger’s mission is to give developers the best tools, so they can have a better day; customer service is one of the company’s core guiding principles Links and resources: Honeybadger (https://www.honeybadger.io/) Starting & Sustaining Podcast Episode with Ben Curtis, Co-founder of Honeybadger (https://interviews.startingandsustaining.com/ben-curtis) Notion (https://www.notion.so/) Twitch (https://www.twitch.tv/) Tropical MBA Podcast (http://www.tropicalmba.com/podcasts/) MicroConf (https://www.microconf.com/) RailsConf (https://railsconf.com/) Postmark (https://postmarkapp.com/) Printfection (https://www.printfection.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/)

25 March 2019


80: Rediscovering Deep Work

80: Rediscovering Deep Work

Derrick’s been traveling and finding inspiration from re-reading Deep Work, a kind of manifesto of what Level stands for. He’s discovering how to position and market Level, as well as recognize things in his own work patterns that need to change. Ben’s been feeling anxiety and thinking about Tuple’s broader mission and impact on the world. He believes deep work can be accomplished through the powerful practice of pair programming. Today’s Topics Include: Embracing Boredom: Derrick removed Twitter and email client from his phone as dependence on distraction Recruiting next wave of paying customers; reminding people what Level is and why they should care about it Learning is a valid category of work you can do during the day; productive use of time Ability to go deep and focus is a skill most people have lost; getting back into the mindset Tuple’s mission and onboarding campaign; selling a solution to an underlying problem Apprenticeship: Learn and gain expertise from peers Derrick’s main piece of content for Level may not be about specific tool to achieve mindful workplace Celebrating call quality feedback feature in Tuple; customized CRM to close the deal Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) Deep Work by Cal Newport (https://www.amazon.com/Deep-Work-Focused-Success-Distracted/dp/1455586692) The Challenger Sale by Matthew Dixon (https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/1591844355) Heroku (https://www.heroku.com/) Screenhero (https://screenhero.com/) Ruby on Rails (https://rubyonrails.org/) Podcast Motor (https://www.podcastmotor.com/) Clearbit (https://clearbit.com/) Brennan Dunn’s Double Your Freelancing (https://doubleyourfreelancing.com)

21 March 2019


79: Moving out of Alpha

79: Moving out of Alpha

Ben shares that Tuple is now out of alpha and into beta, which is an arbitrary marker of stability and feature ability. The move is working as planned by serving as a way for customers to choose to opt in or out, depending on if they want it now or wait until it’s launched. Derrick choose to steer away from such labels with Level, but understands they might have been beneficial to clearly denote the product’s progress. Today’s Topics Include: Ben’s in onboarding mode with Tuple; spent February selling, people pre-pay first month Where are these people coming from? Inbound interest via email list Derrick’s next high-level thing to do is proactively recruit key teams, but how? No more free trials for Level; Derrick has no qualms about asking people to pay for it Tuple’s always testing new pricing, so some prices were tweaked recently Two New Tuple Things: Ability to control resolution of call from guest side, and retrospective added to discuss how product and company are better than last week Notifications feature in Level finally shipped on Friday; Derrick’s responding to feedback Level’s Potential Golden Metric: Switching rate from Slack If it’s not worth paying for, why not? Feeling ready and right, not forcing a decision Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Drip (https://www.drip.com/) Clearbit Enrichment (https://clearbit.com/enrichment) Patrick McKenzie on Twitter (https://twitter.com/patio11) Brian Casel on Twitter (https://twitter.com/CasJam)

18 March 2019


78: Ultraworking with Sebastian Marshall

78: Ultraworking with Sebastian Marshall

We all freak out about things from time to time. Ben becomes neurotic about feedback, but fellow Tuple team members have different triggers that put them into a tailspin. Fortunately, Ben has found ways to better handle stress. In this episode, Ben and Derrick are joined by Sebastian Marshall, co-founder of Ultraworking. In previous episodes, Ben has mentioned Ultraworking and how he has benefitted from it. Today’s Topics Include: Using what he learned about monthly planning from Ultraworking, Ben did March for Tuple Ben met meditation goal via Ultraworking’s Lights spreadsheet, accountability partners 10 to 10: Ben’s theme for March; wants to win the night and beginning of the day by going to bed at the right time and developing a morning routine to be more alert and energetic Ben’s doing Tuple demos and getting positive feedback; promising things are happening Derrick decided to move forward with notifications feature for Level; shipping it soon Note about Level’s performance improvement offers positive sentiment and sanity check How much do you trust your own emotional memory, if you feel like you’re making progress or not? Do a data-driven review of week to assess and analyze headway Track where your time is spent using start and end time; only track most important work Defining wasted vs. leisure time; aren’t they the same? Depends on how you feel afterwards? Good or bad? Two categories of “bad” time: Neurotic flow and regret agreeing to something Average day in the life of Sebastian at Ultraworking; what makes or breaks his week Building a company and keeping it alive; Ben’s “duh” moment about delegating Ultraworking’s Work Cycles: Doing work (creative, technical, etc.) in structured way Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Ultraworking (https://www.ultraworking.com/aop) Ultraworking: Monthly Planning (https://www.ultraworking.com/monthly) Ultraworking: Cycles Template (https://www.ultraworking.com/cycles) Ultraworking: Lights Spreadsheet (https://www.ultraworking.com/lights) Roguelike by Sebastian Marshall (https://www.goodreads.com/book/show/25535056-roguelike) GitLab (https://about.gitlab.com/) Bench (https://bench.co/) Drip (https://www.drip.com/) Extreme Productivity by Robert Pozen (https://www.amazon.com/Extreme-Productivity-Boost-Results-Reduce-ebook/dp/B007HBLNSS)

14 March 2019


77: Reset Your Perspective

77: Reset Your Perspective

Ben’s been checking in with Tuple users to find out how things are going. Things aren’t working perfectly with the product. Before this feedback, he was feeling pretty good about things. It’s not the feedback’s fault, but Ben focusing too much on it. Derrick can empathize with Ben because of his experience with Level. It takes just one negative outcome to have an irrational impact on your mental state. Reset your perspective! Today’s Topics Include: Considering additional indicators within Tuple to gain feedback Ready to buy another seat? Tuple’s first expansion revenue Having a healthy level of stress vs. being in a state of complacency or false optimism As a coping mechanism, Ben reached his goal to mediate every day for a month Don’t let negativity infect everything else; improvement and growth are important Onboarding process and positive changes between original and revised product versions Oh no! Say it isn’t so; Tuple’s using Slack for feedback dialogue Lack of sleep didn’t stop Derrick from shipping performance improvements to Level Derrick expresses gratitude for open source technology that he’s using to build Level Tuple team finally getting a paycheck, a well-earned achievement; Derrick did the opposite and transferred a bucket of cash into Level’s account Getting to the next level of swag; trials and T-shirts to put credit card on file Product advice and ideas for notifications and posts in Level’s Inbox Selling annual deals to specific people, companies; we’re in this together for the long haul Trying to find time to write and talk about journey of starting a new product and company Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Zoom (https://zoom.us/) DataLoader (https://github.com/facebook/dataloader) Waking Up with Sam Harris (https://wakingup.com/) Elixir (https://elixir-lang.org/) Elm (https://elm-lang.org/) Stripe (https://stripe.com/) Honeybadger (https://www.honeybadger.io/) Heroku (https://www.heroku.com/) Jason Cohen (https://twitter.com/asmartbear) MicroConf (https://www.microconf.com/) Brian Casel (https://briancasel.com/)

7 March 2019


76: The Scotch Budget

76: The Scotch Budget

Derrick’s been on a startup roller coaster. It’s been one of those weeks for him. So, he’s grateful for Scotch! He just factors it into Level’s budget. Along the same lines, Tuple bought lunch today for its staff. It feels free, but Ben doesn’t think you can write off such expenses, even if you talk about business between bites. Today’s Topics Include: Boring numbers stuff and stress of assembling financials for 2018 taxes Ben’s goal to meditate every day in February to feel centered in the startup world Spotify surfacing new music helps re-energize Derrick’s work day Tuple’s Goals: Focus on stability in February; onboard additional teams and return to feature development in March Don’t assume; ask users what they want and make sure you clearly understand them Derrick shares Level updates on Startups for the Rest of Us podcast Do metrics matter? Derrick’s on an information diet to uncloud his brain No Twitter for Ben before noon because it’s too much of a distraction Performance overhaul and interface update to improve users’ impression of Level Tuple’s recent improvements include proxy server support and a feedback button Ben’s Tuple Onboarding Calls: Fun to show people the product for the first time Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick’s Level Manifesto (https://level.app/manifesto) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Waking Up with Sam Harris (https://wakingup.com/) Headspace (https://www.headspace.com/) Naughty Professor on Spotify (https://open.spotify.com/artist/5oVhfa2J5GiPx2x0YTuJjI) Episode 429: Building a Launch List of 5,900 and Grinding Out Customer Development (https://www.startupsfortherestofus.com/episodes/episode-429-building-a-launch-list-of-5900-and-grinding-out-customer-development) Drip (https://www.drip.com/) Ruby on Rails (https://rubyonrails.org/)

28 February 2019


75: Lots to Be Grateful For

75: Lots to Be Grateful For

Ben is thankful for Tuple’s success so far. It is helping companies improve efficiency and countries improve the quality of their residents’ lives. Derrick also expresses gratitude for companies being interested in his product, Level. He is setting up a specific team in Level and addressing concerns to convert them. Today’s Topics Include: People want to work at Tuple, and specifically for Ben; it’s flattering, but Tuple is not hiring Tuple beat out a competitor during a company’s trial use Tuple will be given to Watsi, a non-profit that does crowdfunding for medical procedures in third-world countries and is developing a platform for countries to manage healthcare Core Competency: Keep your brain sane during challenges and changes Vice vs. Virtue: Coach and convince champions that Level may not be immediately gratifying, but a virtuous and better way to work Tuple is no longer offering free trials; pain of purchase and pre-qualification put up front Calls to action, connections, and surveys help identify ideal prospects and leads Links and resources: Watsi (https://watsi.org/) YNAB (https://www.youneedabudget.com/) Ultraworking (https://www.ultraworking.com/lights) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick’s Level Manifesto (https://level.app/manifesto) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/)

21 February 2019


74: The Only Way To Learn

74: The Only Way To Learn

Do you lack energy or motivation at work? Ben tried a new service called, Work Gym from Ultraworking. He found it worthwhile and got a lot of work done on Tuple that he had been putting off for quite awhile. Tuple is about to reach a major milestone - recent PR deployments mean no more global list of online users. Derrick has also been addressing how to set up companies, teams, and individual users interested in trying Level. So, he hasn’t intentionally built any billing model into the backend of Level, yet Today’s Topics Include: Prioritizing tasks and trying to be comfortable with the lack of knowing everything Ben and Derrick find value in sales and onboarding calls, although the take up time Doesn’t matter if something isn’t right, right now; keep experimenting, learning, and testing to figure out what works People are willing to pre-pay to be placed on the newly created Tuple trials wait list Tuple Status: Stability is going up, bugs are being fixed, and crashing occurs less often Tuple plans to deploy a fix where users don’t have to enter a keychain password every time to update the app and support for them to choose which display they want to share Results from Superhuman Product Market Fit Survey sent to Tuple users Ben’s Bad Idea: He decided not to do Habits for Hackers due to lack of pricing and bids Derrick continues to do onboarding calls with Level users and reach out to those who were invited and pre-paid, but have not scheduled a demo Derrick shipped an integration for users to post a message to an endpoint that will be directly posted to a channel or another person in Level to centralize relevant notifications Links and resources: Ultraworking (https://www.ultraworking.com/) Ultraworking’s Cycles Template (https://www.ultraworking.com/cycles) Zoom (https://zoom.us/) Superhuman Product Market Fit Survey (https://www.slideshare.net/marklittlewood/rahul-vohra-founderceo-superhuman-the-productmarket-fit-engine-122102118) Habits for Hackers (https://www.habitsforhackers.com/) Zapier (https://zapier.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/)

7 February 2019


73: Helping Early Access Customers Get Value Quickly

73: Helping Early Access Customers Get Value Quickly

Ben has been experiencing a mix of emotions. Thanks to Tuple, his calendar is packed, and he’s getting more emails, people, and trials. It feels nuts, but it feels like things are working with the new product. It’s a crazy spot to be in, but it feels good. Every day, Tuple gains a little steam. Derrick feels the same way. He has started doing onboarding calls for Level. Now that he has done the Level demo a few times, his anxiety has subsided. Overall, people seem impressed with the product and interested in trying it. Today’s Topics Include: Developing a call to action and pricing process to follow the product demo Trials vs. Pay-Up-Front: Ideal customers expect to try it, before they pay for it Instrumentation put in place to test Level; ship solutions in a speedy manner Users are changing their behavior and using Level in a meaningful or experimental capacity to find a balance between it and Slack Big Surprise: Derrick’s relief about a mobile client not being a big deal, right now Power of Customer Development: You won’t know the most valuable points of a product, until you let people use it People are pretty forgiving; when they offer feedback, be responsive and try to fix bugs Revision of auction for Habits for Hackers; bidding started, but may not be high enough Pros and cons of slowing down growth or allowing it to speed up; it’s hard to improve product without feedback Superhuman Product Market Fit Survey: How disappointed would you be, if you had to stop using Tuple? Keeping people educated on all the things your product can do Trying to not over-engineer things; looking for the simplest solutions and integrations Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Habits for Hackers (https://www.habitsforhackers.com/) Drip (https://www.drip.com) Justin Jackson (https://justinjackson.ca/) Superhuman Product Market Fit Survey (https://www.slideshare.net/marklittlewood/rahul-vohra-founderceo-superhuman-the-productmarket-fit-engine-122102118) Zapier (https://zapier.com/) Segment (https://segment.com/) JSON (https://www.json.org/) Rand Fishkin’s Lost and Founder Book (https://sparktoro.com/book)

31 January 2019


72: How to Know If a Product Is Ready

72: How to Know If a Product Is Ready

Derrick set Jan. 21 as the date to start onboarding some pre-order people for Level. He is trying to keep things in perspective when it comes to both positive and negative feedback. So, he is preparing answers to address questions and concerns about the product’s features and functions, or lack of. Ben’s thirsty for more feedback, customers, and interaction. Fortunately, overall feedback for Tuple has been strongly positively. However, any negativity can be brutal. It’s a mental game. So, he tries to not fear feedback or let it derail progress. Instead, he focuses on celebrating successes. Today’s Topics Include: How to know if a product is ready - present it to people Level’s Onboarding Goals: Introduce them to product via a demo/training, get their account created, and set up game plan for the future Overcoming hurdles and getting people to do stuff Calendly Calls: Preparing for and performing them is more exhaustive than writing code Last-minute list of Level features Derrick wants to include and reconcile Tag Team Mouse Mode: Hand-off feature change made for Tuple Making assumptions, instead of the simplest solution Interesting 4G experience onboarding Tuple team member in India Ben asks for Derrick’s forgiveness and understanding for starting a Slack group to get feedback on Tuple Enterprise Sales Process and Pricing: Customer easily spends $5,000, but it takes 5 weeks - keep the ball rolling Middle-ground Approach: Make Tuple available to those who want it, can have success Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Rob Walling (https://robwalling.com/) Jason Cohen (https://twitter.com/asmartbear) Calendly (https://calendly.com/) John Gruber (https://daringfireball.net/) Drip (https://www.drip.com/)

24 January 2019


71: Beyond Alpha

71: Beyond Alpha

Ben has been busy. The alpha launch date for Tuple was Jan. 7. He was nervous about it, but so far, it’s going well. One participant said, “I’m sort of surprised you’re calling this an ‘alpha,’ because everything seems to work!” Ben was glad to hear it, but admits that’s not totally true. He’s still far from where he wants to be with Tuple, but is definitely on the right track. Derrick has been hard at work, too. He continues to develop Level and knows that there will be ups and downs with customers, functionality, etc. But, he continues to move forward and strives to help others solve problems associated with team communication. Today’s Topics Include: Importance of manually onboarding people via calls about product Setting expectations and communication efforts for a rolling roll out Users understand that bugs will happen and offer friendly feedback Experimenting with pricing models for product’s current and future releases Tuple’s performance dashboard displays key details; caring about things that matter Bandwidth: Do fewer things and do them well to be able to compete Level’s future strategies and goals regarding customers and feedback If a product can solve a user’s problem, then it’s good enough to give to them Poor execution and explanation of Drip’s price increase Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Drip (https://www.drip.com/) Calendly (https://calendly.com/) Screenhero (https://screenhero.com/) MicroConf (https://www.microconf.com/) Superhuman (https://superhuman.com/) Jason Fried (https://twitter.com/jasonfried) Jason Cohen (https://twitter.com/asmartbear) Brian Casel (https://briancasel.com/)

17 January 2019


70: Refactoring UI: Concept to Launch

70: Refactoring UI: Concept to Launch

If you listen regularly to the Art of Product podcast, then you’re probably familiar with the ongoing joke: How long does it take before we mention Steve Schoger and Adam Wathan? Well, today is your lucky day because not only do Derrick and Ben mention them, but Adam is once again their special guest. Adam is a software developer, writer, speaker, and entrepreneur. Also, he is the creator of Nitpick CI, host of the Full Stack Radio podcast, and author of Refactoring UI and Refactoring to Collections. He describes the process of successfully making, promoting, and selling courses on the Internet. Plus, Steve makes a special appearance to share his side of the story! Today’s Topics Include: Concept and Collaboration: How Adam and Steve work together to create courses Be genuinely helpful by offering free, good content for people to know, like, and trust you Build an audience/authority on a topic to make people want to learn from you Understand difference between what you care about vs. what your audience cares about Care about quality and effort put into all aspects; utilize Steve’s design tips on Twitter Signals and validation that your content resonates with and is helpful to your audience What Makes a Successful Partnership: Similar values, but complementary skills Promotion via email, newsletter, social media, case studies, and screencasts to grow number of subscribers/followers Courses: Parts and Pieces (Books, Videos, and More) and Pricing to Make ROI Launching Products and Surpassing Sales Expectations Links and resources: Adam Wathan (https://adamwathan.me/) Nitpick CI (https://nitpick-ci.com/) Refactoring UI (https://refactoringui.com/book/) Refactoring to Collections (https://adamwathan.me/refactoring-to-collections/) Full Stack Radio Podcast (http://www.fullstackradio.com/) Adam Wathan’s MicroConf Presentation (https://microconf.gen.co/adam-wathan/) Adam Wathan on GitHub (https://github.com/adamwathan) Adam Wathan’s Email (mailto:adam.wathan@gmail.com) Adam Wathan on Twitter (https://twitter.com/adamwathan) 7 Practical Tips for Cheating at Design (https://medium.com/refactoring-ui/7-practical-tips-for-cheating-at-design-40c736799886) Steve Schoger (https://www.steveschoger.com/) Steve Schoger on YouTube (https://www.youtube.com/channel/UCxqiDtkXtOCNJdckODHk9YA) Heroicons (http://www.heroicons.com/) Steve Schoger on Twitter (https://twitter.com/steveschoger) Wes Bos (https://wesbos.com/) Bootstrap (https://getbootstrap.com/) Stripe (https://stripe.com/) An eBook pricing model that resulted in $100,000 in sales (https://blog.asmartbear.com/selling-ebook.html) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/)

10 January 2019


69: Sound, Actionable Advice with Jason Cohen

69: Sound, Actionable Advice with Jason Cohen

Derrick is away, so Ben welcomes Jason Cohen, CTO of WP Engine and four-time entrepreneur. Jason knows a thing or two about startups and mentoring them to achieve profitability and growth. Jason is a straight talker and tells it like it is to get to solutions sooner. He encourages bootstrap founders to find an advisor who aligns with their goals. You need to know how to take advice and use advice that is right for you and your business. Even if you get great advice, think for yourself! Today’s Topics Include: Advice is not enough; luck, execution, and other pieces are involved Be honest and know what qualities investors want Jason characterizes a company as a learning machine that’s constantly failing, not doing the right thing, and has no resources; but has agility to learn and react quickly Embrace your humanity and smallness; don’t lie about being big Share the good and bad about your startup journey for others to feel connected to and support it When making decisions, apply filters to cut out things; constraints are useful Universal Rule of Success: You’re all in and apply a lot of energy; makes you more productive and fulfilled Many paths lead to success and failure; pick ones that naturally fit you A good engineer can build features (not risky), but can they do everything else - probably not (risky); identify how a company’s priorities need to change to address risk To be sustainable, get help and became an expert in something - not everything Product success depends on use cases and maturity of company (convince customers how good it is now and will get even better); if product isn’t good, then business won’t last Jason shares ideas and options regarding Ben’s Tuple product When bootstrapping, getting money is challenging because you’re not on people’s radar Links and resources: WP Engine (https://wpengine.com) A Smart Bear Blog (https://blog.asmartbear.com/) Can you bootstrap a company on the side? (Part 1 with Jason Cohen) (https://www.youtube.com/watch?v=ESZ3ViBEC3U) Jason Cohen - Designing the Ideal Bootstrapped Business (https://vimeo.com/74338272) Capital Factory (https://www.capitalfactory.com/) Paul Graham (http://www.paulgraham.com/) SmartBear (https://smartbear.com/) Peter Thiel (https://en.wikipedia.org/wiki/Peter_Thiel) Adwords (https://ads.google.com/home/) Slack (https://slack.com/) Hangouts (https://hangouts.google.com/) Marco (https://marco.org) Silicon Valley Successes Podcast (https://www.siliconvalleysuccesses.com/podcast/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/)

27 December 2018


68: Creating Differentiating Features

68: Creating Differentiating Features

Derrick continues to make progress and work toward his self-imposed deadline for Level. He was able to implement and ship batched notifications for the product, which replaces the instantaneous push notifications you would get from a chat tool. It’ll probably be one of the key features to sell as part of the “Level” way. But he’s wondering how to leverage interesting features in marketing. Ben has been thinking about the same thing with Tuple. He wants to make some features of his product be a seperate, discrete entity that deserves its own spotlight. Capitalize on features! Today’s Topics Include: Craft a narrative around “why we did this and the choices we made” for features Tuple offers two modes: Navigator and Copilot Avoid labeling every single feature as a big deal; strike a careful balance Derrick’s working on reactions feature for Level; encourages thoughtful responses Difference between like and acknowledge notifications; making them stateful Derrick closed pre-orders for Level on Dec. 14 and figuring out pricing paradigm Derrick plans to do individual onboarding to set users up for success with Level People are willing to pre-pay; optimize for meaningful engagement and feedback When something is not going well and you don’t know how to fix it, know you’re not alone Ben’s Bad Day: Pairing session revealed bugs and latency issues with Tuple Coping strategies for dealing with catastrophes; don’t freak out, blow out of proportion Tuple’s Week: Added 200 to mailing list, chasing leads, and improving product Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Stripe (https://stripe.com/) Screenhero (https://screenhero.com/) Slack (https://slack.com/) Basecamp (https://basecamp.com/) iOS (https://developer.apple.com/ios/) Superhuman (https://superhuman.com/) Drip (https://www.drip.com/)

20 December 2018


67: Refining Level Notifications and Tuple Alpha Users

67: Refining Level Notifications and Tuple Alpha Users

Derrick had an interesting week with Level. He focused on important features that will be a part of the product, including notifications dependent on team members’ jobs. Some may want more asynchronous and unobtrusive notifications than others. Level distinguishes configurable notifications based on different roles on a team. Notification policies seem simple on the surface, but are actually very complicated. Ben announced that November was Tuple’s best month ever for marketing! But now, he is approaching the alpha for Tuple and will focus his attention on product management. Ben wants to figure out what works and what doesn’t. After all, when you can see the wrong thing, the right thing becomes so much easier. Today’s Topics Include: Derrick gained clarity on how things should work in Level by writing code and playing with different ideas When in doubt about design, Derrick takes a screenshot of Level to put on Twitter and get feedback; keeps people invested in the process Derrick is developing a thick skin and trying to not be defensive about design comments Level will offer opt-ins and education that help users protect their time and priorities Ben plans to pair with people using Tuple to identify UX annoyances Tuple is about to crack the 3,000 people milestone on its mailing list Level received new refers and spikes in traffic; awareness is building How to continue to grow your tribe? Opportunities to have an audience when you’re doing interesting stuff Level’s content strategy will focus on high-quality content, not high-volume content; Derrick plans to commit to cadence of consistency Can spend time on something, and years later, people still go to it as a valuable reference Ben wants to open up sales for the Habits for Hackers course, but limit the number of spots available; he’s considering a reverse auction Derrick’s been considering creative ways to structure pre-orders and pre-sales for Level; trying to decide whether to turn off pre-orders Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Habits for Hackers (https://www.habitsforhackers.com/) Steve Schoger (https://www.steveschoger.com/) Adam Wathan (https://adamwathan.me/) 103: Steve Schoger - Design Q&A + Refactoring UI Details (http://www.fullstackradio.com/103) Slack (https://slack.com/) Dense Discovery (https://www.densediscovery.com/archive/) SitePoint (https://www.sitepoint.com/newsletter/) Product Hunt (https://www.producthunt.com/) Hacker News (https://news.ycombinator.com/) Rob Walling (https://robwalling.com/) Paul Jarvis (https://pjrvs.com/) Brian Casel (https://productizeandscale.com/) Code that says why it does (https://robots.thoughtbot.com/code-that-says-why-it-does)

13 December 2018


66: TinySeed Updates with Rob Walling

66: TinySeed Updates with Rob Walling

Ben and Derrick are joined by Rob Walling to share updates - their favorite part of most podcasts! It’s been a good week in Tuple marketing land. Thanks to Ben’s tweet announcing the release date for its alpha, his launch list goal was reached. He was surprised by how willing people were to help out when he asked them to do it. Rob is working on TinySeed, a startup accelerator for bootstrappers. Derrick provided a pre-order update on Level and plans to do direct outreach to those who ordered it to determine their level of interest for validation. Today’s Topics Include: Managing Mental State: Jubilation followed by fear; developers tend to turn something positive into a negative Ben’s customized onboarding experience with Superhuman to be set up for success TinySeed takes a sane approach to work and build stuff that everyone can benefit from Believing in and making a big commitment to your startup; if it fails, that’ll be a bummer Frequent Feedback: Know where you’re going Angel investing has given Rob a specific skill set from how to pick founders/companies to being their advisor More money doesn’t make you move faster, especially when it comes to SaaS startups TinySeed follows the dividends/cash for equity approach when milestones are met to align everybody; forced accountability through meetings Derrick is working on Level’s onboarding flow and laying a foundation for future tutorials for users to embrace a different way of working Derrick’s addressing the legal side of Level, such as privacy policies/terms of service Chat is junk food - it’s a bad thing, but you still want it; Level is more like the vegetables and what you actually need Links and resources: Rob Walling (https://robwalling.com/) Startups for the Rest of Us (https://www.startupsfortherestofus.com/) Drip (https://www.drip.com/) Brian Casel (https://briancasel.com/) Chad Fowler (http://chadfowler.com/) Superhuman (https://superhuman.com/) Business of Software (https://businessofsoftware.org/) The Product Market Fit Engine (https://businessofsoftware.org/2018/11/product-market-fit-engine-rahul-vohra-ceo-superhuman/) Reportive (http://www.reportive.com/) TinySeed (https://tinyseed.com/) MicroConf (https://www.microconf.com/) HubSpot (https://www.hubspot.com/) SparkToro (https://sparktoro.com/) Paul Graham (http://www.paulgraham.com/) Joanna Wiebe (https://copyhackers.com/about-copy-hackers/) Snapterms (http://snapterms.com/) Stripe Atlas (https://stripe.com/atlas) Slack (https://slack.com/) Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/)

6 December 2018


65: Effectively Managing Launch Day

65: Effectively Managing Launch Day

Ben launched Habits for Hackers, a workshop that cultivates habits that lead to an impressive and fulfilling dev career. He incorporates books written by others and makes that content applicable to participants. He’s going to figure out the rest of the details for the course while flying by the seat of his pants. For now, Ben’s just bathing in the dopamine of watching numbers happen! Derrick has been doing some launching, too. He announced that the end of January will be the beginning of the Level launch and Level can now be pre-ordered (generated about $2,000 so far). Derrick admits that he’s always derailed pretty heavily on launch days. He doesn’t even think about trying to get much productive stuff done. Today’s Topics Include: Tuple had a good week and useful coaching call; find and reach out to experts via useful blog posts and mailing lists Ben’s team has experienced some wins when working on reducing the latency of Tuple, but discovered reducing latency and reducing perceived latency are about the same Ben and Derrick are recognizing areas where they will some day shift their focus Derrick recognizes the revenue potential due to who is signing up for Level (teams vs. entire companies); shipped an improved call to action - save your place in line How Derrick determined the price point for Level; pricing is relative and psychology Ben is reluctant to commit to pricing for Tuple; always trying new numbers to gauge tolerance on how much people are willing to pay for it After a launch, Derrick and Ben feel wiped out because then it’s time to do the hard stuff; create a prioritized list and set a deadline to avoid distractions Ben picked a date for Tuple’s alpha to start - Jan. 7; rather than just take someone’s money, he wants to make sure they are the right fit and would offer worthwhile feedback Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Level Manifesto (https://level.app/manifesto) The Level Journal (https://leveljournal.com/) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) Habits for Hackers (https://www.habitsforhackers.com/) Atomic Habits (https://jamesclear.com/atomic-habits) Deep Work (https://www.amazon.com/Deep-Work-Focused-Success-Distracted/dp/1455586692) Jason Fried (https://twitter.com/jasonfried) Drip (https://www.drip.com/) Slack (https://slack.com/) How Superhuman Built an Engine to Find Product/Market Fit (https://firstround.com/review/how-superhuman-built-an-engine-to-find-product-market-fit/) Tailwind (https://www.tailwindcss.com/) Steve Schoger (https://www.steveschoger.com/) Adam Wathan (https://adamwathan.me/) Sketch (https://www.sketchapp.com/) Mod&dot (https://mod-dot.com/teaser/)

29 November 2018


64: Habits for Hackers

64: Habits for Hackers

Derrick shipped Level’s Daily Digest feature, which includes a summary of unread/read posts, sampling of posts/replies, and call to action. Also, thanks to Derrick killing it on Twitter, Art of Product’s social media presence is now legit! Branding and awareness of Ben’s Tuple pair programming tool has garnered interest from well-known companies. So, it’s time to set a deadline for Tuple’s alpha. Today’s Topics Include: Ups and downs of building a feature Good Brain Hacking: Know yourself and have a strategy; try something from your toolbox to change your perspective Ben designed the Habits for Hackers course; the experience was 50% amazing and 50% arduous - getting better at design through a trial-and-error method Ben’s Design Tips: Copy existing things, read design tweets and watch refactoring UI videos from Steve Schoger, and have friends who will tell you when something isn’t good Your success is a lagging indicator of your habits; Ben wants to be held accountable for practicing good development/work habits Links and resources: Art of Product on Twitter (https://twitter.com/artofproductpod) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Level Manifesto (https://level.app/manifesto) The Level Journal (https://leveljournal.com/) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) Habits for Hackers (https://www.habitsforhackers.com/) Postmark (https://postmarkapp.com/) Ruby on Rails (https://rubyonrails.org/) GitHub (https://github.com/) Elixir (https://elixir-lang.org/) Tailwind (https://www.tailwindapp.com/) Steve Schoger (https://www.steveschoger.com/) Steve Schoger’s Refactoring UI (https://refactoringui.com/) Adam Wathan (https://adamwathan.me/) Sketch (https://www.sketchapp.com/) The Bike Shed (http://bikeshed.fm/) Atomic Habits (https://jamesclear.com/atomic-habits)

21 November 2018


63: Running Successful Early Access Programs

63: Running Successful Early Access Programs

Ben and Derrick were hoping to share a great conversation they had with author, designer, and consultant Paul Jarvis. But, without warning, all was lost when Paul’s audio for the episode could not be saved. The plan is to have Paul back on the show in a few weeks. Everything else is going pretty well for Derrick, who provides an update on Level. He met his goal and launched the Level Early Access Program two weeks ago. When it comes to testing Tuple, Ben plans to prioritize people early on who have good bandwidth and help guide them to be successful when using the tool. Today’s Topics Include: Takeaway and Wake-up Call: Derrick has 6 teams in the early access program; some are using Level a lot, some are not - people are busy and running their own business Quality feedback for Level testing; offers unknowns, guidance, and clarifications Derrick’s working on a feature to make sure users remember to check back into Level because it’s designed to be unobtrusive and not bother you Make a good first impression; capture users’ vision and maintain their interest Derrick addressed people’s questions about how Level works and will solve their problems via storytelling with concrete, mechanical product details Derrick is battling perfection, but wants to generate pre-order revenue and set a rolling launch deadline for Level - ideally in January, to highlight new tools in the new year Ben is doing a podcast tour to promote Tuple, which had its best week for sign ups so far Tuple also experienced a technical breakthrough - it crushed latency; trust your team to get things done Tuple adventure is predicated on a value proposition that Tuple can be better than off-the-shelf products because of its key differentiators Ben is not your everyday developer; recently took a leap and hit the bigtime being a backup singer for Josh Groban! Links and resources: Paul Jarvis (https://pjrvs.com/) Trello (https://trello.com/) Elixir (https://elixir-lang.org/) Slack (https://slack.com/) MicroConf (https://www.microconf.com/) Drip (https://www.drip.com/) CodeNewbie Podcast (https://www.codenewbie.org/podcast) Bits and Trees Podcast (https://podcast.bitsandtrees.com/6) Full Stack Radio Podcast (http://www.fullstackradio.com/101) Ruby Testing Podcast (http://www.rubytestingpodcast.com/) Bootstrapped Web Podcast (http://bootstrappedweb.com/ben-orenstein-joins-us-talk-bootstrapping/) Swift (https://developer.apple.com/swift/) JSON (https://www.json.org/) Postmark (https://postmarkapp.com/) Screenhero (https://screenhero.com/) Josh Groban (http://www.joshgroban.com/) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Level Manifesto (https://level.app/manifesto) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide)

15 November 2018


62: Avoiding Negativity

62: Avoiding Negativity

Derrick had a productive week with Level. His deadline of late October to have alpha users try it was looming. So, he has been a bit stressed out. But thanks to relaxation techniques that work for him, Derrick was able to talk himself off the edge! Ben understands the needs for coping techniques. When little things in his personal life aren’t under control, it’s much harder for him to be productive at work. Every thing’s interconnected. Today’s Topics Include: Battle between work and personal life What makes you happy? Avoid negativity and realize things are going to be ok Ben’s Failure State: When he doesn’t know what to do for a goal Make list of known ingredients needed and check off tasks to push you through Ben’s team did a retrospective for Tuple; marketing is going well and additions have been made to the Tuple Pair Programming Guide Limiting handle reservations and duplicate updates/emails to opt in or opening up handle reservations that cost something Who’s serious about your product? Is filtering the funnel good? Creating sales or a sales team for Level; how Drip did it Suffering from and dealing with Imposter Syndrome Links and resources: Efficiency Starts with a Haircut (http://giantrobots.fm/208) Elm (https://elm-lang.org/) Steve Schoger (https://www.steveschoger.com/) Adam Wathan (https://adamwathan.me/) Drip (https://www.drip.com/) Rob Walling (https://robwalling.com/) Patrick McKenzie (https://twitter.com/patio11) Stripe (https://stripe.com/) MicroConf (https://www.microconf.com/) Sherry Walling of ZenFounder (https://zenfounder.com/about/) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide)

8 November 2018


61: Unconventional Growth Tactics with Julian Shapiro

61: Unconventional Growth Tactics with Julian Shapiro

Ben is working on marketing plans for Tuple and it’s associated Pair Programming Guide. So, what does someone he admires think of his growth and content marketing plans? In this episode, Ben’s special guest is Julian Shapiro, who shares lesser known growth tactics he has used in his content marketing to be successful. Today’s Topics Include: Write content that’s best for your target audience; what do you want them to get out of it? Goal: To have people read your content or buy your product Content marketing in the form of in-depth guides is effective in building a presence and getting people to trust you to pay a high price for your product An audience is an asset; you can identify how much they can be monetized for whatever you want to build in the future Content needs to be more than good; establish credibility, awareness, and knowledge Focus on getting new email subscribers or prepare for the launch of Tuple? Capture people’s interest when you have it Tuple’s Approach to Growth: Release product to a small group to get feedback, release to another group for further testing, repeat, and then expand scope of growth efforts Push content to address objections; why customers need/should care about something How do you apply growth marketing to a giant piece of content? Ads don’t work; A/B test to optimize content; pitch a product, but don’t jeopardize your integrity Non-paid promotion of content - get on Hacker News; never ask someone to upvote, but use a title that expresses deep annoyance and grief about the state of tech SEO is easier with small pieces of content; don’t go for low-hanging fruit, but head turns Part of the magic of Tuple - making it fast to address latency and not feel like a hack Growth should be a core competency of any startup Links and resources: Julian Shapiro (https://www.julian.com) Julian Shapiro on Twitter (https://twitter.com/julian) Bell Curve (https://www.bellcurve.com/) Bell Curve Training (https://www.bellcurve.com/training) Gary Vaynerchuk (https://www.garyvaynerchuk.com/) Tim Ferriss (https://tim.blog/) Hacker News (https://news.ycombinator.com/) TechCrunch (https://techcrunch.com/) Screenhero (https://screenhero.com/) Superhuman (https://superhuman.com/) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide)

1 November 2018


60: Celebrating the Small Wins

60: Celebrating the Small Wins

The feeling of accomplishment you get from doing hard things has become Derrick’s way of living recently. Building a startup like Level is hard, but he feels good when he makes small wins. It’s rewarding when he makes progress. Ben is on a roll right now with Tuple. He’s making progress and getting stuff done. His Pairing Programming Guide is turning people into Tuple subscribers. Today’s Topics Include: Have people with high standards read and review your writing to get feedback Ben’s article, The Case for Pair Programming, was on the front page of Hacker News Ben’s marketing efforts for Tuple have increased its number of subscribers Derrick has a unique challenge of prioritization, so he set a deadline Derrick used Postgres to build a rudimentary search into Level By the end of October, Derrick should have people/teams to test and use Level Product Task List: After you launch, that’s not the end, it’s the beginning Balancing personal finances with no income; set the bar high, but don’t sell yourself short Links and resources: Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) The Case for Pair Programming (https://news.ycombinator.com/item?id=18230465) Upcase (https://thoughtbot.com/upcase) Indie Hackers (https://www.indiehackers.com)

25 October 2018


59: Pros and Cons of Working Alone on a Product

59: Pros and Cons of Working Alone on a Product

Adam Wathan, a software developer, writer, speaker, and entrepreneur joins Ben and Derrick on this episode. Adam is also the creator of Nitpick CI, author of Refactoring to Collections, and host of the Full Stack Radio podcast. Usually isolated and working alone, Adam enjoys the opportunity to chat with others about what everyone is working on. It’s like a mastermind session that’s fun and rewarding! Today’s Topics Include: Ben launched Tuple’s Pair Programming Guide earlier than expected at learntopair.com Ben continues to focus on marketing for Tuple, while other team members are developing the product Derrick feels a sense of guilt when working, but not sharing; once you get out of the habit of working in public, it might be difficult to return to it Derrick is up against his deadline of having a deliverable by the end of October Pros and cons of working alone or with partners to handle tasks/responsibilities Rails vs. Laravel Battle? No, PHP as a language battles with no one Adam is working on a refactoring UI book/design survival kit; chapters are independent and pricing still needs to be established What are digital vs. physical perks you could offer to those who purchase a product first? Derrick has been getting Level ready for alpha users and spending time, more than he wants, to get file uploads to work on it Links and resources: Adam Wathan (https://adamwathan.me/) Nitpick CI (https://nitpick-ci.com/) Refactoring to Collections (https://adamwathan.me/refactoring-to-collections/) Full Stack Radio Podcast (http://www.fullstackradio.com/) Adam Wathan on GitHub (https://github.com/adamwathan) Adam Wathan’s Email (mailto:adam.wathan@gmail.com) Adam Wathan on Twitter (https://twitter.com/adamwathan) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Pair Programming Guide (https://tuple.app/pair-programming-guide) Product Hunt (https://www.producthunt.com/) Extreme Programming Book (https://www.amazon.com/Extreme-Programming-Explained-Embrace-Change/dp/0321278658) Laravel (https://laravel.com/) Ruby on Rails (https://rubyonrails.org/) Steve Schoger (https://www.steveschoger.com/) Colorbox by Lyft (https://www.producthunt.com/posts/colorbox-by-lyft) Tailwind CSS (https://tailwindcss.com)

18 October 2018


58: Evolving Roles as a Startup Founder

58: Evolving Roles as a Startup Founder

Ben and Derrick are joined by Brian Casel, podcaster, cofounder of Big Snow Tiny Conf, and known as “Mr. Process.” The three are fans of podcasts and conferences because they offer time to build relationships with people and talk deeply about things. In this episode, they share their updates and thoughts on involving others in their day-to-day processes. It brings everyone together to learn from each other, as well as build a community and consensus. Today’s Topics Include: Hosting and handling logistics for smaller conferences and retreats Ben shipped his Pair Programming Guide that offers tips, tutorials, and resources Guide to serve as top of funnel for Tuple; build an audience, establish expertise, get people together who care about it, and offer them a tool Flipping into different modes (writing, marketing, programming, etc.); in startup mode, you’re trying to make progress and doing everything - even when you have partners More people are live streaming their coding sessions, writing processes, and other tasks - documenting the creation and development of a product or service Build trust with a group of people to build referrals and have them talk about your product; but giving fans access to your product and building a community can be challenging Building a new product; spend money to hire someone to do it fast or take it slow and learn to do it yourself but don’t get paid for your time When building a company or product, it can be fun and frustrating; these days you should know a bit about all the pieces to it - teaching infrastructure is now an industry Coaches and friends can give you advice and let you know just what you need to know Practice Project vs. Real Product Mindsets: Perfecting something that you know won’t be perfect out of the gate, making it as good as possible, or plan first and then execute Links and resources: Brian Casel on Twitter (https://twitter.com/CasJam) Productize & Scale (https://productizeandscale.com/) Big Snow Tiny Conf (https://bigsnowtinyconf.com/) BootstrappedWeb (http://bootstrappedweb.com/) ProcessKit (https://processkit.com/) Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) MicroConf (https://www.microconf.com/) Startups for the Rest of Us (https://www.startupsfortherestofus.com/) Tuple’s Pair Programming Guide (https://tuple.app/pair-programming-guide) Pairing with Ben Orenstein on the Tuple Pairing Guide (with Adam Wathan) (https://www.youtube.com/watch?v=SK27unk2UuI) Jason Fried (https://twitter.com/jasonfried) Laravel (https://laravel.com/) Mackenzie Child (https://www.youtube.com/user/mackenziechild) Drift and David Cancel (https://team.drift.com/david) Ruby on Rails (https://rubyonrails.org/)

11 October 2018


57: Finding the Right Marketing/Product Balance

57: Finding the Right Marketing/Product Balance

Ben recently returned from an entrepreneur retreat that featured sessions and activities focused on various topics, from projects people were working on to troubles with cofounders. Attendees were able to be honest, open, and transparent with each other. Ben had the opportunity to demo Tuple during the retreat. Feedback was that there are too many people working on its development, so he should focus on marketing. Derrick emphasized the importance of keeping in mind the cost of getting someone caught up to speed on a project. He has thought about hiring a contractor to help with the development of Level, but decided that his single brain was enough. Today’s Topics Include: Ben is working on a website to host the best pair programming guide on the Internet Not getting on the content marketing treadmill, but coming out with 1 or 2 solid, comprehensive pieces of content that draw in people Cascading style sheets (CSS) make your website site look good; should you hire a designer or learn the basics on your own? Create a good network; know people who know about things, and ask for help Derrick pushed a license update for Level’s code base; justified reasons why he should or shouldn’t make it an open source product and garner legal protection Derrick’s original end-of-October people testing goal for Level is still possible; using Trello to list and clarify tasks Finding a balance between making progress and doing other things that keep a product in people’s minds Tuple’s team is starting to adopt more foundational processes to address tasks Feedback from Listeners: More interaction and question-asking between Derrick and Ben, as well as bring people into their podcast process Links and resources: Derrick Reimer (http://www.derrickreimer.com) Website Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein (http://www.benorenstein.com/) Website Ben Orenstein on Twitter (https://twitter.com/r00k?lang=en) Level (https://level.app/) Tuple (https://tuple.app/) Thoughtbot (https://thoughtbot.com/) Big Snow Tiny Conf (https://bigsnowtinyconf.com/) MicroConf (https://www.microconf.com/) Julian.com (https://www.julian.com/) Tailwind (https://tailwindcss.com) Redis (https://redislabs.com/) Trello (https://trello.com/)

4 October 2018


56: Finding Your One Thing

56: Finding Your One Thing

Ben is back from retreat #2 for Tuple. It may not have been as good as the first retreat, but was still above baseline productivity. The team worked on refactoring the app. Then, he went to CocoaHeads, which is for MacOS X and iOS developers to discuss Apple's Cocoa and CocoaTouch. Derrick will be speaking about Level at the local Elixir meetup. He is excited to dive deeper into using Elixir and reading books about it. Then, he plans to share what he learns and encourage others to not be intimidated by more powerful concepts in Elixir. Today’s Topics Include: Ben talks about climbing; if he’s not good at something, that makes him feel bad, so he needs to overcome such a feeling Derrick has been trying to figure out strategically how to provide a valuable service around Level’s open source code base; needs to put in the effort of learning how it’ll work Importance of developing DevOps skills, knowledge - whether it’s you or in-house experts As Derrick rapidly builds features for Level, he is tempted to either skimp on full-comprehensive testing or taking extra steps to refactor features into their ideal form Derrick and Ben both are figuring out where they should be and where they should focus their time and efforts as they create their new products Speed and quality are not traded off for one another; code has to be good to be added to and changed later quickly Share what you’ve done with others to be reviewed and receive feedback; plus share your thoughts via Twitter with Ben and Derrick on how they can improve their podcast! Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) Tuple (https://tuple.app/) CocoaHeads (http://cocoaheads.org/) Elixir (https://elixir-lang.org/) Thoughtbot (https://thoughtbot.com/) Discourse (https://discourse.org/) Docker (https://www.docker.com/)

20 September 2018


55: The Entrepreneurial Rollercoaster

55: The Entrepreneurial Rollercoaster

Derrick is in Washington for ElixirConf. Like Elixir, he is becoming more comfortable with stability, as opposed to constant churn and new stuff all the time. He knows you have to show restraint to try and not solve every problem. While at the conference, Derrick wants to make connections with people and hopes Level will one day be a good use case example for the Elixir community. Ben is discovering that startups are not easy. There are a lot of ups and downs. While other people were enjoying Labor Day, Ben was actually being a boss and getting work done. He may not have worked on the highest priority, but on a task that was satisfying to work on. Today’s Topics Include: Derrick has been keeping up his dev journal for Level by chronicling stories about the day-to-day building process; keeps him focused For his journal, Derrick is using Svbtle, which offers a beta option to enable SSL for secure custom domains Derrick is experimenting with newer Web platform functionality and built a custom element for Level to inject custom HTML and send push notifications Ben was planning to pair using the Tuple app, but a bunch of stuff broke Highs and lows with Tuple have been crazy; the lows make Ben wonder if it is ever going to work Derrick tried using Level with someone else and everything seemed confusing; feel good about small wins, but rough spots can be difficult Still a lot to do with Tuple, but Ben is making forward progress; keyboard support and other features have been merged - becoming a working app Ben has some performance and latency leads for Tuple that are promising Tuple continues to be tested inside and outside of Ben’s team to address variables Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) The Level Journal (https://leveljournal.com/) Tuple (https://tuple.app/) ElixirConf (https://elixirconf.com/) RubyConf (https://rubyconf.org/) Heroku (https://www.heroku.com/) Richard Feldman (https://github.com/rtfeldman/) Svbtle (https://svbtle.com/)

13 September 2018


54: Continuous Learning

54: Continuous Learning

Ben has been focusing on MacOS development and writing code. There’s so much he doesn’t know. But that’s ok. He strives to regularly learn things - just keep making progress for it to feel less intimidating. Derrick has the same mindset. It’s ok to not know everything. Start with the basics, and keep going. You’ll figure things out eventually. Today’s Topics Include: Ben is battling being part of the action or not and what tasks to handle; what is his role? Ben feels guilty about changing his mind, but doesn’t stick with non-optimal decisions Ben is discovering through calls and conversations that there is a market for Tuple Derrick has been focused on the new version of Elm and migrating to it; Elm is not going to break, and it has been thoroughly tested Level development continues with time spent on the Inbox; wants to get the MVP out Derrick plans to do journaling to share things and keep people involved with Level Make the Internet better and faster by not following stupid rules Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) Derrick’s Manifesto (https://level.app/manifesto) Tuple (https://tuple.app/) Elm (http://elm-lang.org/) Basecamp (https://basecamp.com/) Drip (https://www.drip.com/)

30 August 2018


53: Launching Transistor.fm with Justin Jackson

53: Launching Transistor.fm with Justin Jackson

Today’s guest, Justin Jackson, just launched a podcast platform called, Transistor.fm. Justin describes the time he spent working with co-founder Jon Buda to get it ready to go live. Launching involves a lot of energy and emotion with ups and downs. Whether working on your own or with someone else, Justin encourages you to take time away to work on something to focus on it and make significant progress. Today’s Topics Include: Reporting is key feature for podcast hosting applications; Transistor.fm offers an awesome analytics feature When catching up with competitors, have a comparable minimum set of features Some features don’t look good in screenshots; showcase a feature Lots of time was spent on the launch, which Justin hoped would create a ripple effect for sign ups, word of mouth, tweets, and other engagement People see something on Product Hunt, and they buy it; it’s an easy decision but not an intent-based audience - looking for entertainment and freebies Splash for Transistor.fm made it the #1 product and generated sign ups A podcast is an investment; Justin decided to use credit card sign up for Transistor.fm to build a brand and trust Calculating churn, setting expectations, and reaching goals; banking on slow, steady growth Starting work on Spots.fm, self-serve ads for indie creators; making it as easy to advertise on a podcast as it is advertising on Facebook Get a company to sponsor you and write off as marketing expense; way for podcasters to earn income from their show Talk, observe, and listen to “normals” to find that people buy things because of podcasts; don’t change people’s priorities to fit your ideals Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) Derrick’s Manifesto (https://level.app/manifesto) Tuple (https://tuple.app/) Build Your SaaS Podcast (https://saas.transistor.fm/) MegaMaker (https://megamaker.co/) Justin Jackson Newsletter (https://justinjackson.ca/newsletter/) The Importance of Trust with Your Audience with Justin Jackson (http://artofproductpodcast.com/episode-46) Transistor.fm (https://transistor.fm/) Laracon (http://laracon.us/) Tuple Native App and Level Inbox Workflows (http://artofproductpodcast.com/episode-52) Product Hunt (https://www.producthunt.com/) Rob Walling (https://robwalling.com/) Tim Ferriss (https://tim.blog/)

23 August 2018


52: Tuple Native App and Level Inbox Workflows

52: Tuple Native App and Level Inbox Workflows

Ben is back from a productive retreat with his Tuple co-founders. It was deep concentration work that didn’t feel like a chore, but a feeling of joy. They experienced a milestone - scrapped the electron-based version of their app to work on a native functional prototype. There’s a ton more to do, but it basically works. The pieces are coming together. Derrick understands the foundation required to pretty much get anything done with a new product. He is considering a future retreat, but wondering if the benefits are worth it to go off somewhere as a solo founder. Or, would it be more productive to be just sitting at his desk at home? The most critical item on his radar and one of the biggest unknowns he continues to battle is how the mechanics of Level’s Inbox will work. If it doesn’t function well, then the whole promise of the app breaks down. Today’s Topics Include: Ben is trying to get to dog food ability - being able to pair using the app while actually working on the app Ben is using Basecamp and GitHub Issues to manage tasks that are still left to do Ben is still experiencing a steady stream of tweets, sharing, and sign ups for Tuple Derrick also has a steady stream of tweets and is up to 4,500 handle reservations Derrick is evaluating what paradigm he is mirroring when it comes to notifications and actionable to do items It can be counterintuitive but ultimately helpful to think about something so technical that it sends you back into a loop of higher level conceptual thinking Derrick’s making progress and at a decision point; trust his instincts and build something to be used, build a prototype, or build static mock-ups? Take a risk and set a date! Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) Derrick’s Manifesto (https://level.app/manifesto) Tuple (https://tuple.app/) Codetree (https://codetree.com/) Basecamp (https://basecamp.com/) GitHub Issues (https://github.com/github/hub/issues) Drip (https://www.drip.com/)

16 August 2018


51: Recast - The Origin of Level from Startups for the Rest of Us

51: Recast - The Origin of Level from Startups for the Rest of Us

Ben is out of town on a retreat with his Tuple co-founders, and Derrick is deep into building Level. So, this episode features Derrick as a recent guest on the Startups for the Rest of Us podcast. Rob Walling interviews Derrick about Level - what inspired the idea and how he went about trying to validate it. Today’s Topics Include: Level’s landing page and current query of number of members; scarcity play is effective Level is a Slack competitor, but much less interruptive and more asynchronous Derrick discovered Slack does not scale well as a team grows, interrupts people’s flow; Level is Derrick’s take on the solution to those issues Derrick hit the ground running with his manifesto and getting people signed up for Level His efforts on Twitter were effective because it’s a product marketed toward developers Dealing with feedback, ill-informed comments and conversations Derrick wanted to talk to too many, rather than too few people about value of creating a new product to address pain points Differentiation from Slack: Level niched down to developers and open sourced Derrick plans to offer free and on-prem versions of Level Whiteboarding to go over ideas and transform them into something tangible Derrick is working on mock-ups; challenging to lay out UI elements, such as the Inbox Risks are involved; when building something new, the challenge is to validate your most risky hypotheses - the ones that are most likely to fail Level is the third Saas startup that Derrick has worked on; first time he will not earn income or revenue while building Level, so had to make adjustments Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) Derrick’s Manifesto (https://level.app/manifesto) Tuple (https://tuple.app/) Fostering a Culture of Creativity with Rob Walling (http://artofproductpodcast.com/episode-42) Exploring the Open Source Business Model (http://artofproductpodcast.com/episode-44) Startups for the Rest of Us: How Derrick Reimer is Validating His Ambitious Third Saas (https://www.startupsfortherestofus.com/episodes/episode-399-how-derrick-reimer-is-validating-his-ambitious-third-saas-application) Application (https://www.startupsfortherestofus.com/episodes/episode-399-how-derrick-reimer-is-validating-his-ambitious-third-saas-application) Drip (https://www.drip.com/) Codetree (https://codetree.com/) MicroConf (https://www.microconf.com/)

9 August 2018


50: Doing the Hard Things First

50: Doing the Hard Things First

Derrick continues to reinvent himself with his new product, Level, and sporting a, “I work for myself beard.” He took a vacation to canoe and camp instead of code. It’s always a refreshing experience for him to get away from work from time to time. Now, Derrick is back to writing code and organizing tasks in Levelland. Ben also went on vacation, but before doing so, he realized no sales for Tuple had come in that week. So, he made an effort to call prospective clients and was able to sell six annual licenses. Now, like Derrick, he is working on things that are hard to achieve. But if they can make them happen, then they will be really good. Today’s Topics Include: If feeling overwhelmed, write everything down, break into chunks, and organize them Find a visible way to make sure you are making progress and staying on track Ben wants to talk to other CEOs of small companies to find out what are they focused on and paying attention to because there is so much to do Don’t beat up yourself over mistakes, just keep making progress AoP podcast is like therapy and leaning on each other for support during this journey; staying sane during the new company/product process Prioritize Properly: Get sleep or you’re operating at a fraction at what you could be Break up your day and work schedule into 2-3 hour segments; if you need to get something done, spend less time doing it Teams contacted Ben about participating in the Tuple alpha; spots are still available, so contact him Company or founder retreats are a way to get creative, think outside the box, and bond over shared challenges and struggles Ben’s team, Sam Deane, including has been cranking away on its native app to create the initial set-up, layout, and architecture Ben tweeted about how to get up to speed on Mac OS development; considered corporate overlord’s job to create education and training, so it doesn’t get done Looking back on a year if AoP: Derrick overcame his fear of the microphone, and they’re keeping it real; humbled and happy that people find it useful Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) Tuple (https://tuple.app/) Hill Charts on Basecamp (https://basecamp.com/features/hill-charts) Trello (https://trello.com/) Drip (https://www.drip.com/) Rob Walling (https://robwalling.com/) Sketch (https://www.sketchapp.com/) Giant Robots Smashing Into Other Giant Robots (http://giantrobots.fm/episodes) Microconf (https://www.microconf.com/)

26 July 2018


49: The Evolving Tech Stack

49: The Evolving Tech Stack

Derrick continues to code to make progress on things he will need to build at some point for his product, Level. Also, he spent a lot of time in Elm land for refactoring and additions. Will Elm code work for scaling necessary for Level? Derrick is still trying to decide. Ben’s team at Tuple has transitioned from C++ to Swift, a newer and friendlier language. Also, Tuple hired a consultant as a sanity check and to be pointed in the right direction for building a native app on Mac. Initially, the consultant will help step up and build with dependencies needed. Today’s Topics Include: Level App: There’s a lot of work to do and time is flying by; not sure when it’s going to be ready, but every day, make progress More than 800 people have signed up for Ben’s Code Quality Challenge; people engaged in it are getting value, doing useful things, and improving their apps Advantages of building your network up online; they share and inquire about info you post Types of tips that spread fast, including bash, shell, and git Ben plans to reach out to people to make podcast appearances to promote Tuple Ben stepped away from sales, but now plans to make money for the company his #1 priority; difference between self-funding and bootstrapping Being in a constant state of push-and-pull; when to do this/that and change directions If you’re interested in entrepreneurship, read Shoe Dog by Phil Knight; jumping through hoops and funding a company Check out Founder to CEO by Matt Mochary, who coaches tech startup CEOs in Silicon Valley; what do you need to know to grow? Friendly reminder if you’re going camping this summer, remember to take mosquito repellent with you! Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) Tuple (https://tuple.app/) Elm (http://elm-lang.org/) Richard Feldman on YouTube (https://www.youtube.com/results?search_query=richard+feldman+elm) Swift (https://developer.apple.com/swift/) Derrick Reimer on Startups for the Rest of Us (https://www.startupsfortherestofus.com/episodes/episode-399-how-derrick-reimer-is-validating-his-ambitious-third-saas-application) Derrick Reimer on Full Stack Radio (http://www.fullstackradio.com/92) Ben Orenstein’s Code Quality Challenge (https://www.codequalitychallenge.com/) Ben Orenstein’s Shell Tricks Post (https://twitter.com/r00k/status/1013970705229197317) Shoe Dog (https://www.amazon.com/Shoe-Dog-Phil-Knight/dp/1508211809) Founder to CEO (https://docs.google.com/document/d/1ZJZbv4J6FZ8Dnb0JuMhJxTnwl-dwqx5xl0s65DE3wO8/preview)

12 July 2018


48: When Is the Right Time to Take Outside Funding?

48: When Is the Right Time to Take Outside Funding?

Derrick was hoping to finish mock-ups for communication flows inside Level to get feedback, but that turned out to be a lofty goal that he is still working on. The process of designing Level has generated more questions than answers and minute details that Derrick needs to address. This is the real work happens. Congrats to Ben, who finally crossed 10,000 followers on Twitter. He uses Twitter as a way to provide value, be useful, and build relationships. Also, he launched the Code Quality Challenge sign-ups and a private podcast to share information with people who are interested in Tuple. Today’s Topics Include: Interest in seed funding? Different ways to raise funding Being in complete control of your destiny and avoiding failure Doubling down to take investments; what’s it like to be in a business environment that received funding Rob Walling’s experience with funded companies; listen to a recap of 12 Lessons I learned Moving from Bootstrapped to Venture Backed (https://lan.io/blog/podcast/rob-walling/) Personalities and psychology of founders impact own vs. others’ money Flexibility: Choose to push hard and make something profitable or not Head lamp requirement to enjoy the great outdoors, and how being tall has its benefits Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) Tuple (https://tuple.app/) Drip (https://www.drip.com/) Briefs podcasting service (https://www.briefs.fm/) Microconf (https://www.microconf.com/) Rob Walling (https://robwalling.com/)

5 July 2018


47: Pacing Yourself When Starting Up

47: Pacing Yourself When Starting Up

Despite being in the process of building new companies and products, Derrick and Ben understand the importance of sustainable pace - being able to unplug and get some rest to make smart decisions. So, Derrick just got back from vacation, and Ben plans to take some days off soon. It’s about the mental component of mastering your brain. Derrick is getting back into the swing of things and trying to finish the mock-ups for communication flows inside Level. Ben has been focusing on filling up Tuple’s alpha and booking substantial pre-pays. Also, Ben shipped his landing page and already has about 12,000 subscribers. Today’s Topics Include: Moving away from crud and crappy versions, and switching to a fully native app Reaching a certain bar to get the product in users’ hand; adjust and pivot as needed and be a suitable alternative Making a decision whether to build in Electron or not Is a desktop app necessary? Always-open option can lead to missed productivity KPI dashboard - what gets measured, gets managed Restart of code quality challenge: Sign up for next cohort in July Following challenge, pitch people on paid pair programming course Buying time to make a product really good, and training next generation of customers Business Idea: CEOs need dashboards 5-Minute Journal: I’m grateful for, what would make today great, and I am…; and 3 amazing things that happened today and how could I have made today even better Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level (https://level.app/) Tuple (https://tuple.app/) Derrick Reimer on Full Stack Radio - Designing a Calmer Team Communication Platform (http://www.fullstackradio.com/91) Electron (https://electronjs.org/)

28 June 2018


46: The Importance of Trust with Your Audience with Justin Jackson

46: The Importance of Trust with Your Audience with Justin Jackson

Today’s episode features guest Justin Jackson, who is building a new podcasting startup called, Transistor.fm, and runs MegaMaker training and books for SaaS and indie software companies. He’s discovering that it’s a lot of work to build something. Derrick and Ben know how he feels. For Derrick, it’s been a fun week in the land of Level. He’s been working on his new landing page and landing new sign-ups for the pre-launch list. Ben has pre-sold $700 worth of Tuple accounts and raised $500 worth of verbal “Yeses.” Contact Ben if you want to be a part of Tuple. They share their ups and downs, fears and triumphs! Today’s Topics Include: Should I learn more programming? More design? Acquire skills to connect the two It’s easier to build something after building relationships; a personal approach makes you stand out Can connection with core audience become a scalable competitive advantage? Ways to tell your story and generate followers before you have product info available Get your product into the hands of potential users Propensity that you know all the answers, but bury your ego and ask for help Deciding how much to charge, pricing structure You can get people to sign up and get them to pay for it, but can you get them to use it and keep using it? Invest in something that offers a virtuous cycle of revenue back to your company Demonstrate value of existing content; making money and conversions from specific campaigns and activities Fears and feelings when people are not using a product Hire customer support people to reach out to customers and generate revenue Trend is automated software companies, but the most successful companies emphasize a human service component Pair programming always bubbles to the surface Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Justin Jackson (https://justinjackson.ca/) Justin Jackson on Twitter (https://twitter.com/mijustin?lang=en) Level (https://level.app/) Build Your Saas podcast (https://saas.transistor.fm/) Transistor.fm (https://transistor.fm/) MicroConf (https://www.microconf.com/) Jason Fried (https://twitter.com/jasonfried) Seth Godin (https://www.sethgodin.com/) RightMessage (https://rightmessage.com/) How We’ve Taken FOMO 20k to 80k by Justin Mares (https://microconf.gen.co/justin-mares)

14 June 2018


45: The Value of Teaching

45: The Value of Teaching

He’s back! Ben returns from traveling to Hong Kong. He shared his rails knowledge by helping someone who is building a business and using a rails app. He made performance improvements and refactored items. Derrick is also doing some Vim tutoring. Learning something new does not take long or a lot of money, and gets easier. Of course, both Ben and Derrick continue to work on their new products, as well. Derrick is creating Level, an open source team communication and management tool. Ben is starting Tuple, a pair programming tool alternative for Screenhero. Today’s Topics Include: How to do file browser for projects in Vim: CtrlP; baked-in and plug-ins options for Vim Build and code, but talking to customers can impact your course and business Derrick is posting small, hot tips on Twitter that are nuggets of valuable knowledge Likes and retweets growing Derrick’s number of followers Ben needs to tweet more to market to developers for his new product - Tuple Derrick continues to work on Level; categorizing communication and how to present it Notion of urgency is big issue with Slack that Derrick needs to address with Level Brainstorming sometimes needs conversation, and sometimes long periods of silence Controlling distractions and creating checklists are part of Derrick’s daily routine Derrick is improving the copywriting and calls to action on Level’s landing page Ben plans to incentivize people via annual plan upsells Derrick is considering a referral tracking mechanism as an incentive Big transitions and uncertainty generate anxiety for Ben, but he now has strategies to deal with it Trying to create a thing that did not exist before is different than something that already exists; it is harder and more stressful, and you’ll feel pain and be unsure Ben’s role as external-facing sales and marketing vs. product development and coding Structuring to make yourself happy, but keeping staff happy, too; everyone should like what they are doing Links and resources: Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Vim (https://www.vim.org/) CtrlP (https://github.com/kien/ctrlp.vim) Your First vimrc Should be Nearly Empty (http://www.benorenstein.com/blog/your-first-vimrc-should-be-nearly-empty) Thoughtbot (https://thoughtbot.com/) MicroConf (https://www.microconf.com/) Momentum (https://momentumdash.com/) Mathias Meyer (https://twitter.com/roidrage?lang=en) Reboot Podcast - How You Walk Through the World with Seth Godin (https://www.reboot.io/episode/83-walk-world-seth-godin/)

7 June 2018


44: Exploring the Open Source Business Model

44: Exploring the Open Source Business Model

Rob Walling, co-founder at Drip, MicroConf organizer, and host of the Startups For the Rest of Us podcast, continues to co-host with Derrick while Ben is in Hong Kong. Rob is becoming a believer in 3 to 6 hour work days; he is more productive and has more motivation to get things done. As for Derrick, he read an article titled, After 5 years and $3M, here’s everything we’ve learned from building Ghost, which relates to the business model he is following for his Level product. Ghost is using the open source core product and it’s bootstrapped, which can be difficult. in this episode, Derrick pulls out a few pieces of the article that are relevant to share. Today’s Topics Include: Piece 1: Competing on convenience with centralized platforms was a mistake; took too much time and made it a difficult experience for end users Level customers will either pay or go to the open source version; if they find that self-host vs. buy does not work out, there will be a transition path Piece 2: Building a distributed team is both easier and harder than imagined; the biggest challenges came from human problems, not business problems Drip experienced similar issues with a distributed team; Level will probably have a distributed team to find talent but not be able to compete with bigger companies Pros and cons of remote- vs. office-based teams, such as building camaraderie Piece 3: Open source development is more broken than ever; you are criticized for not doing something or meeting certain standards Derrick plans to set expectations up front and promote opportunities for integration; be transparent and provide value Brand is recognition within a group of people; brand association can be positive when they trust you, but negative if the brand treats them badly Drive word of mouth; it is one of the biggest attraction channels for companies Links and resources: Rob Walling on Twitter (https://twitter.com/robwalling) Startups for the Rest of Us (http://www.startupsfortherestofus.com/) Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) MicroConf (https://www.microconf.com/) Drip (https://www.drip.com/) After 5 years and $3M, here’s everything we’ve learned from building Ghost (https://blog.ghost.org/5/) Build Your Saas Podcast (https://saas.transistor.fm/) SaaStr (https://www.saastr.com/)

31 May 2018


43: Strategizing Product Validation

43: Strategizing Product Validation

Rob Walling joins Derrick once again as a guest co-host while Ben is traveling in Hong Kong. Rob was Derrick's co-founder at Drip, runs MicroConf, and hosts the Startups For the Rest of Us podcast. Derrick and Rob discuss the latest Level updates and strategize how best to approach previewing product mockups to potential customers. They discuss how the early phase of a startup is very fulfilling because you can be very creative, but also stressful because of risk and uncertainty. Rob gets Derrick's feedback about offering one-on-one founder consulting in his spare time. Links and resources: Rob Walling on Twitter (https://twitter.com/robwalling) Startups for the Rest of Us (http://www.startupsfortherestofus.com/) Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) MicroConf (https://www.microconf.com/) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Level Live #3: A Fireside Chat with Rob Walling (https://youtu.be/lDb-93uWVLw) Drip (https://www.drip.com/) Twist (https://twistapp.com/?lang=en) Basecamp (https://basecamp.com/) Soylent (https://www.soylent.com/)

24 May 2018


42: Fostering a Culture of Creativity with Rob Walling

42: Fostering a Culture of Creativity with Rob Walling

Ben is away, so Derrick invited a special guest for this episode. Rob Walling was the co-founder of Drip and is the co-host of MicroConf. Rob recently removed Slack from his phone, and is waiting for Derrick’s Level product. Level is an open source team communication tool that Derrick hopes will replace Slack among software teams. Others are looking forward to Level, as well, and wondering how many clients Level is going to be available on: Mobile, desktop...As Derrick continues to work on Level, the two also reminisce about their days together at Drip. Today’s Topics Include: Derrick is planning to use Electron to build a desktop app for Level Some follow a pure approach and go native, but it can be more difficult than expected Bursting and psychological safety concepts allow people to express their ideas What if? Be creative as a team, encourage everyone to collaborate, and make the environment comfortable for magic to happen Individual vs. group brainstorming: Which works better? How do other companies do it? Derrick plans to show polished, not raw sketches of Level to make it reviewable Derrick has been building the product, writing code, nuking the database, and creating videos to show slices of Level being made Derrick used Stripe Atlas to form an LLC for Level Stripe is inspiring; believe that you can transition an industry, make things happen, and win the hearts and minds of developers Derrick and Rob discuss the pros/cons of fundstrapping vs. bootstrapping Rob shares feedback and reviews from listeners of his podcast Rob and Derrick share their thoughts on cryptocurrency investing If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Rob Walling on Twitter (https://twitter.com/robwalling) Startups for the Rest of Us (http://www.startupsfortherestofus.com/) Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) MicroConf (https://www.microconf.com/) Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Electron (https://electronjs.org/) PhoneGap (http://phonegap.com/) Twist (https://twistapp.com/?lang=en) WorkLife podcast (https://www.ted.com/read/ted-podcasts/worklife) Gusto (https://gusto.com/) Zenefits (https://www.zenefits.com/) The Pixar Touch (https://www.amazon.com/Pixar-Touch-Making-Company/dp/0307278298) Lost and Founder by Rand Fishkin (https://www.amazon.com/Lost-Founder-Painfully-Honest-Startup/dp/0735213321)

17 May 2018


41: MicroConf 2018 Takeaways

41: MicroConf 2018 Takeaways

Ben and Derrick are recovering from days of being in Las Vegas for MicroConf. They spent time reconnecting with old friends, and making new friends. Knowledge floats around, and you can soak it all in. MicroConf has a culture of extreme transparency, helpfulness, friendliness, and wealth of value. Talks at the conference generated actionable items for and awe from attendees. Derrick especially enjoyed copywriting and injecting humor sessions. Ben was impressed, too. His favorite talk was from Justin Mares on “How We’ve Taken FOMO 20 to 80k MRR in 18 Months,” where Mares talked about a difficult task and what worked and didn’t. Today’s Topics Include: Show up every day and try to make your business better Growth regrets and scaling challenges for Derrick with Drip; does slow and steady win the race? Growth and Derrick’s new product Level; he plans to focus in on software developers Don’t be afraid to go into large markets with your products and services to grow Ben met up with the “guy” whose research he is using for his new company and the problems he plans to tackle Ben plans to use WebRTC, unless or until an alternative appears Ben has been thinking about positioning, and how it will affect his UX, pricing, and other factors Ben settled on a name for his new business: Tuple (it was meant to be and nerdy enough for developers to get it) Derrick battles for domains and wins Level.app If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) MicroConf (https://www.microconf.com/) Drip (https://www.drip.com/) WebRTC (https://webrtc.org/)

10 May 2018


40: MicroConf, Equity, and Corporate Entities

40: MicroConf, Equity, and Corporate Entities

Ben and Derrick are together again, at MicroConf and working on their new products and businesses. From making T-shirts to thinking about finding funds, things are continuing to move forward. Derrick is focusing on Level, an open source team communication and management tool. Ben is considering the name, Tuple, for his pair programming tool alternative for Screenhero. He is focusing on all things business-related, from equity to entity options. Today’s Topics Include: What’s equity? Ben determines how to break up partnership percentages for his company Each partner will have their moment in the sun, and contribute more or less at various times Forming an entity; should Ben’s business be an LLC, corporation, private company...? Domain scheme options when it comes to handles and extensions Ben’s next milestone is to do a small alpha, and charge people to use it Embedding iframes, custom domain options, and promotions How cagey to be about technology being used; the secret sauce and general public licenses Learning how to pitch a product and what resonates with people Tools can be improved, and education on how to use them needs to be provided Is Slack the problem, or the people who use it? On premise vs. Cloud options; the pros and cons If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Angel Funds (https://angel.co/angel-funds) MicroConf (https://www.microconf.com/) WebRTC (https://webrtc.org/) Andrew Culver (https://github.com/andrewculver)

3 May 2018


39: Another New Beginning

39: Another New Beginning

Derrick discovered his marketing and promotional tasks were eating up too much of his time and mind, so he took a break from them. He shifted his focus to the actual development of his product, Level. He made some forward strides on the product’s design. Ben decided to give notice and leave his current job for an opportunity to develop a Screenhero alternative. Screenhero is a pair programming tool that has a rough history with Slack. So, he has a co-founder, new technology findings from Stanford, and encouragement from original developers. Could anything be more aligned?! Ben’s alternative and Derrick’s Level is a match made in heaven. Today’s Topics Include: How Derrick is refactoring and optimizing data model items Is having one identity the right way to go or do people want to establish different identities within different communities? Ben encourages Derrick to not automatically do the opposite of Slack Derrick is trying to envision what people may request and be able to customize Shifting from the anonymous to identified Web Why Derrick decided to rewrite some database migration history Derrick is developing Level’s registration and sign-up process Derrick is on a development roller coaster every day; getting back on the yoga train Development teams will become increasingly distributed, so the customer base for Ben’s alternative will only expand How Ben feels about the technology risk factor with his alternative tool Ben will be learning C++ to write the codebase and maintain it If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Tailwind CSS (https://tailwindcss.com/) The Bootstrap Blog (https://blog.getbootstrap.com/) Drip (https://www.drip.com/) GitHub (https://github.com/) Steve Schoger (https://www.steveschoger.com/) Screenhero (https://screenhero.com/) MicroConf (https://www.microconf.com/) Thoughtbot (https://thoughtbot.com/) Ruby on Rails (http://rubyonrails.org/)

26 April 2018


38: Choosing Tech Stack and Taking Preorders

38: Choosing Tech Stack and Taking Preorders

Derrick is still moving in the right direction with the product he is developing called, Level. He used Product Hunt’s Ship to set up a landing page. He plans to promote his upcoming product and control its launch. Also, Derrick published a blog post titled, Building Level #2: The Tech Stack. It summarizes his rationale and reasons why he chose specific technologies. Plus, he posted his and Ben’s conversation, Live Level #2: Branding and GraphQL Mutations, and created a Twitter handle for Level. Today’s Topics Include: Derrick plans to create bite-sized content to engage customers and build trust Fake videos and info products and other shenanigans Derrick has been splitting his time writing backend code and nailing down design Getting feedback on mockups Be aggressive by charging and collecting pre-payments Ben will be going to MicroConf; taking a plane ride with leg room If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Building Level #2: The Tech Stack (http://www.derrickreimer.com/posts/building-level-2-the-tech-stack/) Live Level #2: Branding and GraphQL Mutations (https://www.youtube.com/watch?v=ui3KhMH-kLo) Powered By Level on Twitter (https://twitter.com/poweredbylevel) Steve Schoger (https://www.steveschoger.com/) Product Hunt’s Ship (https://www.producthunt.com/ship) Level on Product Hunt (https://www.producthunt.com/upcoming/level) Drip (https://www.drip.com/) Codetree (https://codetree.com/) MicroConf (https://www.microconf.com/)

19 April 2018


37: Pairing and Building In Public

37: Pairing and Building In Public

Ben is now a Level contributor! Ben has paired with Derrick and his team communication and management tool called, Level - which is officially open source. Also, Derrick recorded himself building a Level feature and posted it on YouTube for feedback. It draws in people to see how an expert does things and share opinions and knowledge. It’s a win-win for everyone! Today’s Topics Include: Leveraging various networks to share information and provide value Building a brand and putting capital in the bank Impacts of stress on productivity Engaging and sharing with interested parties; building relationships Possible Milestone: Establish cadence of publishing frequency and balance of allocating time Proposed Product Milestone: Use Level to track the work on Level Utilizing GitHub to track tasks on To Do lists Finalizing logo and identifying domain for Level Value of retros Prioritizing tasks and making progress on important, but not urgent work Whether to focus on processes or engineering Product roadmap and associated expectations/productivity If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Ben Orenstein Website (http://www.benorenstein.com/) Ben Orenstein on Twitter (https://twitter.com/r00k) Derrick Reimer Website (http://www.derrickreimer.com/) Derrick Reimer on Twitter (https://twitter.com/derrickreimer) Level Live #1: Listing groups within spaces (https://www.youtube.com/watch?v=SwPdHmw5EkE&feature=youtu.be) Level on GitHub (https://github.com/levelhq/level) Steve Schoger (https://www.steveschoger.com/) Drip (https://www.drip.com/)

12 April 2018


36: Building Level

36: Building Level

Derrick continues to talk with customers and gain insights about a team communication and management tool he is developing called, Level. Derrick is developing personal connections with people interested in his mission, and his conversations with customers is reinforcing patterns. Today, he shares the main problems with “Chat” functionality and why people are frustrated with the tools they use today. He is exploring possible solutions for Level to replace Slack and other tools. What issues do you experience? Today’s Topics Include: False sense of urgency; Derrick’s tool would allow you to filter notifications on whether they are urgent or not; and let users view messages at their own pace Chat is like a conveyor belt; if you don’t pick things up, they are going to fall or you are going to miss them Lack of Decent Threading: People do not find threads useful and difficult to encourage appropriate use of them No Mechanism for Tracking State of Conversation: Everything needs to be reviewed to find information and decisions; should offer Open, Closed, Request Review, and On Hold, and other statuses 3 Ways to Structure Messages: 1) Subject and body; 2) Body; or 3) Very small message in infinite timeline Derrick is clear on problems with existing tools, but less clear on exact solutions Simple nuances can make a tool friendlier and easier to use - it’s all in the details Derrick kicked off the Building Level series Ben and Derrick strategize on the best approach to getting teams to try Level Derrick is trying to make the barriers to using Level for low Level will most likely be an open source product with a commercially hosted version to generate revenue Ben and Derrick discuss when it is the best time to start developing Level publicly Ben decided to say “No” to speaking at MicroConf this year; saying “No” to something, is saying “No” to one thing, saying “Yes” to something is saying “No” to everything else If you’re enjoying the show please give us your ratings and reviews in iTunes. Ben Orenstein Website (http://www.benorenstein.com/); Twitter (https://twitter.com/derrickreimer) Derrick Reimer Website (http://www.derrickreimer.com/) Building Level #1: Idea Validation (http://www.derrickreimer.com/posts/building-level-1-idea-validation/) Twist (https://twistapp.com/?lang=en) Drip (https://www.drip.com/) HipChat (https://www.hipchat.com/sign_in) Startup Stories Podcast (http://www.startupstoriespodcast.com/) Stripe (https://stripe.com/) Clearbit’s Reveal (https://clearbit.com/reveal) Derek Sivers (https://sivers.org/) MicroConf (http://www.microconf.com/)

5 April 2018


35: Conducting Customer Development Interviews

35: Conducting Customer Development Interviews

As part of his new business journey, Derrick requested that customers schedule time to talk with him about Level, a team communication and management tool he is developing. Luckily, about 40 people signed up, and he has completed 14 of these calls. What are his customers saying? They confirm main pains they feel with current tools and are very willing to share their frustrations with existing tools. Derrick has not been surprised yet about their answers. In Ben’s world, he is spending time on slinging and reading about Haskell. He is full of questions. Both Ben and Derrick are learning a lot every day, which is fulfilling and exciting. Today’s Topics Include: Level will not be a project management tool, but may have some project management capabilities Derrick’s list of initial questions for customers: What is their company and role within it; the size of their team; what tools they use and when they adopted them; and the balance between chat, email, and project management in their organization Derrick also asks customers: Why are they interested in Level? What problems do they want it to solve? What’s working well for them with Slack, and what’s not? What aspects of Slack do they use and don’t use? Ideas for improvement have come from Derrick’s customers Continuous integration is the clear winner for usefulness Gauging willingness to switch to another tool, such as Level Customers expressed using Level on a pilot basis for specific teams or projects and in coordination with at least one other tool Being unable to post asynchronous, long-form discussions is a pain point for some customers Paying for a tool would not be a big deal Derrick plans to kick off his building Level series and build mock-ups for customers to view Positive use of minimalist user interfaces Debating whether to offer a pre-payment option for Level Ben uses Ansible for the deployment of Haskell code Ben is seeking a Dev Ops person to hire - must have strong opinions and can fix stuff SaaS Renaissance? More developers are starting SaaS companies - a trend already on the way out? Level will be SaaS but with an open source core Tools SaaS companies will want to have and buy Not Built Here Syndrome: Engineers who outsource non-essential parts to someone else Pricing Pages as a Service: Shopify’s checkout page feels natural but still represents the company Avoid rebuilding stuff If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Ben Orenstein Website (http://www.benorenstein.com/); Twitter (https://twitter.com/derrickreimer) Derrick Reimer Website (http://www.derrickreimer.com/) Basecamp (https://basecamp.com/) and Getting Real (https://www.youtube.com/channel/UCdx5Dk3EWTe2i8YDA7bfl6g) Haskell (https://www.haskell.org/) Programming in Haskell book (https://www.amazon.com/Programming-Haskell-Graham-Hutton/dp/0521692695) C Programming Language (https://www.amazon.com/Programming-Language-2nd-Brian-Kernighan/dp/0131103628) by Brian Kernighan and Dennis Ritchie (K&R for C) Ruby on Rails (http://rubyonrails.org/) Ansible (https://www.ansible.com/) Drip Salesforce (https://www.salesforce.com/) Product Hunt (https://www.producthunt.com/) GitLab (https://gitlab.com/)and Discourse (https://github.com/discourse/discourse) Stripe Atlas (https://stripe.com/atlas) Andrew Culver’s Bullet Train (https://twitter.com/i/moments/906824077612109824?lang=en) Adam Savage: One Day Builds (https://www.youtube.com/playlist?list=PLKqXxhKj-VjqKzdBYPeqQUM2No2Ps7qU3) MicroConf 2018 (http://www.microconf.com/)

29 March 2018


34: Maker vs. Manager

34: Maker vs. Manager

It’s a Snow Day for Ben, and Derrick shares his woes about setting up his home office with two new, Dell monitors and his MacBook Pro featuring only two USB-C ports for a hub. You would think that laptops would offer more of a variety of ports. Other than that, things are going great for Derrick. On March 5, Derrick pushed out his manifesto via Twitter. In response, people shared, retweeted, and posted supportive thoughts and messages. Developers resonated with his message. And of course, there were a few skeptics who wondered how Derrick’s ideas were different from other team communication and management options. There will always be multiple tools that can be used, but Derrick has a particular approach to what he offers. Today’s Topics Include: Maker vs. Manager: A good way to draw a line between how different people feel about a tool “This is people problem, not a tool problem” There are a lot of people who just don’t get it. Tools help guide the way users use the product and how your team works Some tools generate stress and interruptions rather than constructive work progress Goal: Communication centralized in one place Email is now a black hole, and no longer for actionable items Important information can get lost in all the noise created by some tools Derrick plans to keep his email subscriber list warm by not over-emailing them without a product available yet Derrick has received 400 emails so far as a result of his Twitter push and plans to do outreach, development, and validation with customers Attribution Tracking App: Ben encouraged Derrick to request pre-pay for future products, like for the app he was thinking about building; pre-payments offers validation Derrick has not determined a price plan or how to sell the dream yet Derrick plans to keep thinking through product decisions on pen and paper Deliver on the promise of the tool guiding people to use good communication patterns Tools need to maintain connectedness Entrepreneurship Porn: Share your thoughts, ideas, process, and journey with others Engagement and Authenticity: A give-and-take between you and your subscribers Journal milestones; the more chronicling, the better Derrick’s prototype includes Phoenix, Elixir, and GraphQL Ben shares his experience with Haskell vs. Elm; he has more questions than answers at this point Haskell has a chance of being the gateway drug of functional programming languages Attend meet-ups and conferences to learn more about Haskell and Elm With programming languages, you need to be willing to make some sacrifices Ben is beginning to appreciate aspects of project management and positively influencing processes If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Ben Orenstein Website (http://www.benorenstein.com/); Twitter (https://twitter.com/derrickreimer) Derrick Reimer Website (http://www.derrickreimer.com/) Basecamp (https://basecamp.com/) Twist (https://twistapp.com/?lang=en) Drip (https://www.drip.com/) Calendly (https://calendly.com/) Jason Fried (https://www.linkedin.com/in/37signals) Startup Stories Podcast (https://itunes.apple.com/ca/podcast/mixergy-startup-stories-1000-entrepreneurs-businesses/id348690336?mt=2) GraphQL (http://graphql.org/) Elixir (https://elixir-lang.org/) Phoenix (https://github.com/kasper/phoenix) Haskell (https://www.haskell.org/); Programming in Haskell book (https://www.amazon.com/Programming-Haskell-Graham-Hutton/dp/0521692695) Elm (http://elm-lang.org/) Ruby on Rails (http://rubyonrails.org/) Thoughtbot (https://thoughtbot.com/)

15 March 2018


33: The War on Developer Productivity

33: The War on Developer Productivity

Derrick recounts his last day at Drip - from being locked out, the elevator breaking, turning in parking passes, wearing a shirt saying “Quit Your Day Job,” to happy hour. Although he has a feeling of being free now, he is bummed about not seeing his co-workers every day. However, he is excited to share his plans and personal mission for the near future - a project called, Level, based on balance, not chaos. Today’s Topics Include: Derrick’s Manifesto: What he is now doing and thinking Building a prototype to get rid of Slack in the workplace Wants to develop ways to improve team communication Parts of Slack are awesome, while others are not Chat is not an effective communication mode for teams Important conversations can get lost in the chatter Snoozing is stressful; can be taken negatively and feel like being ignored Inbox should be included and organized by threads Anything that is important and needs to be addressed should be in a thread Slack is not meant for actionable items, but people use it for that Derrick’s tool will have both sync and async, which can be married; will be difficult to misuse it Some tools become addictive and disruptive to human nature Pushing through notification barriers and specifying priority; a list that prioritizes items and deadlines Step 1 to creating such a tool: Do your homework by talking to teams of developers Ben’s March will consist of meditating, squats, and handstands - while working on goals; Derrick wants to achieve reading and personal fitness goals every day, as well as shipping something open source If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: The War on Developer Productivity (And How I Intend to Win It) (http://www.derrickreimer.com/posts/the-war-on-developer-productivity/) Drip Slack (https://slack.com/) Thoughtbot (https://thoughtbot.com/) Rob Walling (https://www.drip.com/about) The Entrepreneur's Guide to Keeping Your S**t Together by Sherry Walling (https://zenfounder.com/entrepreneurs-guide-keeping-st-together/) Zero to One book (http://zerotoonebook.com/about) Ben Orenstein Website (http://www.benorenstein.com/)

8 March 2018


32: Big Changes

32: Big Changes

Some significant changes are going on in our professional lives and today is full of updates. Ben shares some of the details of his new job at Mackey Research Management Software. It’s providing him with structure, people, team interaction, and new problems, as well as a distance from some other problems. Mackey is a company that makes a note-taking app for hedge funds and features a connection to databases of public companies. Derrick is moving on and away from Drip. While he knows the time is right to move on, there is emotional attachment especially since he was there from the start. Derrick wants to go from leading to doing, again. He’s leaving his “baby” that he co-founded in the best state possible. Derrick is putting together a manifesto about possible upcoming plans. Today’s Topics Include: Reasons for moving away from Rails Ride the wave of different languages Projects based on learning vs. productive; never stop learning to be relevant Change in pace and work environment is positive for Ben Flexibility is a benefit, but it is not for everyone Stress level difference between working at a job or running your own company If Ben likes Haskell, he’ll want to talk and teach about it Haskell has some brain-bender, mind-expander aspects With Haskell, it feels more like play than work for Ben - and you get paid for it Derrick has learned to delegate over the years; no longer a bottleneck New chief technology officer with top-level experience being hired to continue to grow Drip Derrick will post a manifesto on his website about his upcoming plans Derrick has been going through administrative tasks required as he transitions away from Drip Derrick says, even during the dead of winter, that he plans to stay in Minnesota A logo is being created for Art of Product; and Derrick is working on establishing a brand identity related to his new ventures If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Mackey (https://mackeyrms.com/) Haskell (http://haskellformac.com/) Sherry Walling Mental Health for Startup Founders - Art of Product episode (https://itunes.apple.com/us/podcast/the-art-of-product/id1243627144?mt=2#) The 30-Day Code Quality Challenge (https://www.codequalitychallenge.com/) RefactoringRails.io (http://refactoringrails.io/) Drip Derrick Reimer Website (http://www.derrickreimer.com/) Ben Orenstein Website (http://www.benorenstein.com/)

2 March 2018


31: Mental Health for Startup Founders with Sherry Walling

31: Mental Health for Startup Founders with Sherry Walling

Today’s special episode features guest Sherry Walling, author of The Entrepreneur's Guide to Keeping Your S**t Together, to be released February 21, 2018. Sherry explains how her book came to life and her experience self-publishing. We also talk about the common mental health issues for entrepreneurial founders in the community today. Today’s Topics Include: Mental health within the Founders community Sherry’s new book and her writing process Struggles during the publishing process Traditional versus self publishing on Amazon Strengths and ‘shadows’ of entrepreneurs Personality self-knowledge and introversion/extraversion If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: The Entrepreneur's Guide to Keeping Your S**t Together by Sherry Walling (https://zenfounder.com/entrepreneurs-guide-keeping-st-together/) Zen Founder (https://zenfounder.com/) Zen Founder Podcast (https://zenfounder.com/category/episodes/) Quiet: The Power of Introverts in a World That Can't Stop Talking by Susan Cain (https://www.amazon.com/Quiet-Power-Introverts-World-Talking/dp/0307352153) MicroConf (http://www.microconf.com/) The 30-Day Code Quality Challenge (https://www.codequalitychallenge.com/) RefactoringRails.io (http://refactoringrails.io/) Drip

8 February 2018


30: Nailing an Interview, and the New Drip Design

30: Nailing an Interview, and the New Drip Design

Ben has moved into his new apartment and had an interesting discussion about fitness with the movers. Derrick got back is Bod Pod results and is formulating his precise fitness goals for fat loss and muscle gain. Ben is still on the job market and had an interview last week. Ben and Derrick discuss successful interview techniques and experiences they’ve had in the past. In Drip news, Drip recently got a brand refresh, including a new logo, marketing site, color palette, new messaging, app skin, and more. They are working on focusing their marketing efforts to position Drip in the market as an Ecommerce CRM. Listen in as Derrick discusses the Drip refresh and the thinking behind it. Today’s Topics Include: Fitness and Derrick’s fitness goals Drip’s recent brand refresh Market positioning in Ecommerce Ben’s job search progress and interview tactics If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: The 30-Day Code Quality Challenge (https://www.codequalitychallenge.com/) RefactoringRails.io (http://refactoringrails.io/) Drip

25 January 2018


29: Fitness and Code Quality in 2018

29: Fitness and Code Quality in 2018

Ben and Derrick welcome the New Year with this first episode of 2018. Derrick provides an update on his fitness goals for the first quarter of 2018 and plans his Bod Pod evaluation this week. Derrick also shares his strategy improving and maintaining Drip software features. Ben is launching the second cohort of The 30-Day Code Quality Challenge this week, and this cohort is even larger than the first. He shares how this cohort will be different, and thoughts on adding a fee to increase accountability and participation. He is also thinking about future extensions of the challenge into a monetized product. Today’s Topics Include: 2018 Q1 Goal updates The 30-Day Code Quality Challenge second cohort launch Increasing accountability in the Challenge Monetization strategies for courses following a free challenge Drip software and features Navigation-driven development and app workflows Ruby losing popularity If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Nike Training Club App (https://www.nike.com/us/en_us/c/nike-plus/training-app) Bod Pod (http://www.cosmed.com/en/products/body-composition/bod-pod) Precision Nutrition (https://www.precisionnutrition.com/) Ruby Rogues Episode 342: Interview with DHH (https://devchat.tv/ruby-rogues/rr-342-rails-development-david-heinemeier-hansson) The 30-Day Code Quality Challenge (https://www.codequalitychallenge.com/) RefactoringRails.io (http://refactoringrails.io/) Drip

11 January 2018


28: Quarterly Goals, and Why They're Better Than Annual Goals

28: Quarterly Goals, and Why They're Better Than Annual Goals

Ben is having a successful push for the new cohort of The 30-Day Code Quality Challenge. He is also looking to improve future iterations of the challenge and is preparing to move to a new home outside of Boston. Ben and Derrick discuss their quarterly personal goals on this episode and the philosophy behind goal setting: developing habits versus achieving specific results. Each list their specific goals for the first quarter of 2018, including fitness, mindfulness, reading, professional projects and career choices. Today’s Topics Include: Second cohort of The 30-Day Code Quality Challenge Annual versus quarterly goals Effective goal setting: forming habits versus achieving goals Ben and Derrick’s specific goals for Q1 2018 Returning to the tech workforce If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: The 30-Day Code Quality Challenge (https://www.codequalitychallenge.com/) RefactoringRails.io (http://refactoringrails.io/) Drip Proper Cloth (https://propercloth.com/) James Clear - Habits Guide (https://jamesclear.com/habits)

28 December 2017


27: 30 Day Code Quality Challenge, and Elm Development

27: 30 Day Code Quality Challenge, and Elm Development

Ben is entering the last week of The 30-Day Code Quality Challenge. He has enjoyed getting the challenges out each day and seeing participants engage with the content. In the future he is deciding whether to personalize the programming languages or to remain language agnostic. The next cohort of the Challenge will start January 3, 2018, and Ben’s looking forward to iterating and improving each cohort of the Challenge. He also discussed a connection he made with Discourse, and explores options for forum management in the future. Drip is working on their visual email builder with the help of their new Elm developer. The team has just completed several product structure tests using a prototype, which was a greatly helpful experience to the developers. Ben and Derrick discuss their experiences with product usability testing. Today’s Topics Include: Approaching the end of The 30-Day Code Quality Challenge Challenge results and stats on participation The next Challenge cohort begins January 3, 2018 Positive customer experience with Discourse Drip’s visual email builder project Product usability testing If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: The 30-Day Code Quality Challenge (https://www.codequalitychallenge.com/) Discourse (https://www.discourse.org/) Steve Schoger @steveschoger (https://twitter.com/steveschoger) Full Stack Radio podcast 78: Ben Orenstein - Our All-Time Favorite Refactorings (https://www.acast.com/fullstackradio/78-ben-orenstein-our-all-time-favorite-refactorings) RefactoringRails.io (http://refactoringrails.io/) Drip

14 December 2017


26: Optimizing Team Structures

26: Optimizing Team Structures

Drip successfully sailed through Black Friday and Cyber Monday unscathed with no queue backups or problems. Derrick has been thinking about shifting the Drip team structures after Black Friday weekend and is considering adopting more efficient workflows and processes. Ben and Derrick discuss different team structures, including those at Basecamp and Spotify. They also talk about team size, communication overhead, and growing revenue versus growing team size in business. Today’s Topics Include: Drip’s Black Friday success Team structure and restructuring teams at Drip Work processes and discussing article Running in Circles by Ryan Singer Mutable requirements and engineering feedback Uphill Strategies and task deadlines Spotify “squads” and team structures Communication overhead with large teams Be sure to stick around at the end of the episode for Ben and Derrick’s post-show chat. If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: HQ Trivia App (https://itunes.apple.com/us/app/hq-live-trivia-game-show/id1232278996) Running in Circles by Ryan Singer (https://m.signalvnoise.com/running-in-circles-aae73d79ce19) The 30-Day Code Quality Challenge (https://www.codequalitychallenge.com/) RefactoringRails.io (http://refactoringrails.io/) Drip

7 December 2017


25: Chaos, and Growing an Engineering Team

25: Chaos, and Growing an Engineering Team

Ben introduces The 30-Day Code Quality Challenge and updates us on the progress of his first cohort. He has been receiving positive feedback and participants are engaging with the exercises and community forums. They discuss his work on the project and the future of Ben’s business and his audience moving forward. Derrick has hired an Elm engineer at Drip and they discuss the adoption of the Elm programming language in the industry. He also shares the hiring and pairing interview process of the candidate. Derrick attended an interesting invite-only conference, Chaos Engineering Day, and discusses Chaos Engineering and the implications for his business. This week Drip is focused on and fully prepped for Black Friday and shares his team wins surrounding the lead-up. Today’s Topics Include: The 30-Day Code Quality Challenge first cohort launch and progress Discourse versus Slack discussion channels Community building and managing a group Plans for future challenge cohorts and Ben’s business Derrick’s successful hiring process for an Elm engineer Adopting Elm programming language in the industry Chaos Engineering and testing Be sure to stick around at the end of the episode for Ben and Derrick’s post-show chat. If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: The 30-Day Code Quality Challenge (https://www.codequalitychallenge.com/) Discourse (https://www.discourse.org/) Perennial Seller by Ryan Holiday (https://www.amazon.com/Perennial-Seller-Making-Marketing-Lasts/dp/0143109014) Principles of Chaos Engineering (http://principlesofchaos.org/) RefactoringRails.io (http://refactoringrails.io/) Drip

30 November 2017


23: Refactoring Rails Launch Breakdown

23: Refactoring Rails Launch Breakdown

Ben keeps us posted on the Refactoring Rails course launch progress and shares his continuing sales metrics and marketing strategies. He is considering experimenting with free samples, bundling and cross-promoting going forward. For his next project, Ben is creating a new course called The 30-Day Code Quality Challenge, which goes live on November 13, 2017. He has received a lot of feedback on the idea and is iterating on the outline, including content and pricing strategies for the future. He shares his plans for the course and Derrick gives his advice on the project. Today’s Topics Include: Refactoring Rails launch progression and marketing strategies Ben’s new project: The 30-Day Code Quality Challenge Comparing course formats and iterating on ideas using targeted feedback The power of building your audience and list Lead generation versus sales value Programming language agnostic course strategy If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Tiny Marketing Wins course (https://tinymarketingwins.com/) The 30-Day Code Quality Challenge (https://www.codequalitychallenge.com/) RefactoringRails.io (http://refactoringrails.io/) Drip

9 November 2017


22: Finishing the Year Strong

22: Finishing the Year Strong

Ben’s course sales are still going strong, and he shares his updated sales metrics and the purchasing trends of his customers. He also spoke on the Ruby on Rails podcast recently to discuss the course and his experience making it. Ben is scheduled to give a talk at the DC Ruby Users Group on February 16, 2018. He is now trying to think of what’s next for himself in the big picture. Derrick and the Drip team are preparing for Black Friday. They built models to predict peak hours and optimize their servers. As a result they had a super successful test send at over 4,000 emails per second, putting them in a great position leading up to the big day. The team is still working on load testing to search for more unknown factors in simulation to shore up the system even more. Today’s Topics Include: Screenhero shutting down Refactoring Rails launch progress Selling products versus services Work-life balance and project madness Salaried jobs and optimizing work experience Drip prep for Black Friday If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Use together - Screen Sharing Tool (http://www.use-together.com/) Ruby on Rails: Episode 236 (http://5by5.tv/rubyonrails/236) featuring Ben Orenstein Seeking Wisdom: Episode 95 (https://soundcloud.com/seekingwisdom/brad-stulberg) featuring Brad Stulberg The Tropical MBA Podcast (https://soundcloud.com/tmbapodcast) SendGrid (https://sendgrid.com/) RefactoringRails.io (http://refactoringrails.io/) Drip

2 November 2017


21: Launching Refactoring Rails

21: Launching Refactoring Rails

Ben has officially launched his course Refactoring Rails. He is pleased with his choice of back-end tools including Gumroad for fulfillment. Ben shares his course launch metrics including email success rate, sales numbers and revenue. Early feedback has been positive and the Ruby community has been very supportive. He also discusses his expectations and take away lessons from the overall launch. Ben will be continuing his Ruby tour in the coming weeks. Derrick announces Drip’s new project teased last episode: a visual email editor. Due to Drip’s widening customer base, there is an increased demand for visual and polished marketing emails. Their designer has been working on mockups and the team is analyzing the current tools available and have some great ideas for improving usability. Drip is still looking for a front-end engineer with Elm experience to help build the tool. Today’s Topics Include: Refactoring Rails launch and email strategy Ben’s launch metrics Ruby speaking tour The new visual email editor project at Drip Building out a new project Learning new skills as a developer Choosing programming languages Derrick’s review of Microsoft’s Visual Studio Code Editor If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Gumroad (https://gumroad.com/) Heroku (https://devcenter.heroku.com/) Elm "Teaching Elm to Beginners" by Richard Feldman (https://www.youtube.com/watch?v=G-GhUxeYc1U) Microsoft’s Visual Studio Code Editor (https://code.visualstudio.com/) RefactoringRails.io (http://refactoringrails.io/) Drip

26 October 2017


20: The Ups and Downs of Working From the Road

20: The Ups and Downs of Working From the Road

Ben is set to launch his course and is using the looming deadline as an efficiency booster. He recently spoke at Rocky Mountain Ruby, and spent time prepping the talk with a friend at a beach house but unfortunately lost his data due to a hardware malfunction. The talk was still a great success, but a very stressful experience. The next week he spoke at Southeast Ruby in Nashville and it was a much smoother experience. Otherwise he is finishing up launch strategy details and looking forward to shipping the project. Drip.com is now live after a long process, and the Drip team is thrilled. Derrick has also found an opportunity to use Elm at Drip, and is looking forward to implementing it in a new project he can’t yet discuss. Drip is currently looking for a front-end engineer in the Minneapolis area, with Elm experience if possible. Derrick has been travelling recently and even had a flight cancelled due to the California wildfires. Today’s Topics Include: Deadline pressure and work efficiency Ben’s recent speaking engagements Last minute details for Ben’s course release Time-pressure and discount strategies for launch Drip.com domain acquisition Elm programming language If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: How we structure our work and teams at Basecamp (https://m.signalvnoise.com/how-we-set-up-our-work-cbce3d3d9cae)by Jason Fried Elm RefactoringRails.io (http://refactoringrails.io/) Drip

19 October 2017


19: Gourmet Ruby with Avdi Grimm

19: Gourmet Ruby with Avdi Grimm

This week Ben Orenstein is interviewing guest Avdi Grimm, Founder of RubyTapas, which is a subscription service that provides screencasts of “gourmet” ruby programming. Avdi discusses the topic of his talk at Southeast Ruby in Nashville, which was the value of avoiding code and strategies to bypass the need to write unnecessary coding. Join us as he shares his advice on optimizing workflows and his experiences building RubyTapas. Today’s Topics Include: The value of avoiding code Hidden complexity in building out content platforms Using Wordpress for publishing content Code as a liability Episode production and future of RubyTapas Finding leverage in business and creative work Delegating workflows Views on side-hustling and product development If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: RubyTapas (https://www.rubytapas.com/) WordPress (https://wordpress.com/) Spacemacs (http://spacemacs.org/), Emacs (https://www.gnu.org/software/emacs/), Vim (http://www.vim.org/), Neovim (https://neovim.io/) Side-hustle mindset versus product-business mindset (http://www.virtuouscode.com/2017/02/08/side-hustle-mindset-versus-product-business-mindset/) by Avdi Grimm Avdi.codes (https://avdi.codes/) VirtuousCode.com (http://www.virtuouscode.com/) RefactoringRails.io (http://refactoringrails.io/)

12 October 2017


18: Preparing for Black Friday

18: Preparing for Black Friday

Ben has finalized the logo for his Refactoring Rails course and is currently getting the intro/outro animations and the sales site designed. He also finished the notes for all the videos and was very pleased with the final edit quality. The launch date for RefactoringRails.io is October 16th, 2017. He is still considering options for his post-launch speaking tour. At Drip, Derrick is deep in the backend scaling challenges with a lot of attention towards Black Friday for their ecommerce customers. They are looking to historical data in order to anticipate peak volumes and simulate high loads. One particular initiative they’re working on is “fair queuing” to improve Drip’s user experience under periods of high load. Today’s Topics Include: Refactoring Rails course development Scaling challenges and Black Friday volume High-load simulations Amazon auto-scaling groups Fair queuing Open source libraries If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Elm Boston Elm Meetup Refactoring Rails course logo Gumroad Rocky Mountain Ruby GraphQL Narro.co Drip RefactoringRails.io

28 September 2017


17: Launch Planning and Speaking at Conferences

17: Launch Planning and Speaking at Conferences

Ben is coming back from a restorative vacation in Martha’s Vineyard and loves the vibe there. He is enjoying his Vitamix blender and the Dr. Rhonda Patrick micronutrient smoothie. In Refactoring Rails news, Ben is committing to a launch date of October 16th. He is also scheduled to speak at three different conferences before the launch, and is looking forward to the challenge. He got feedback regarding a premium course tier, and is weighing his options on developing these materials. He has a proposal for the design element work and is close to wrapping up on the content. Derrick attended ElixirConf in Seattle and now feels more confident to use the language in Drip in the future. He’s feeling the pain of running a large Ruby application and is looking for a higher power language. They are heading into using auto-scaling groups and other ways of optimizing the system. He was also interested in the code formatter that Elixir is developing. Today’s Topics Include: Health and nutrition in smoothies ElixirConf and the state of the Elixir language Erlang Programming language Scaling Drip, speed and hosting costs Code formatters Launch of Refactoring Rails Premium tier survey and material options Hiring a designer for the course graphics Ben’s upcoming speaking engagements: Rocky Mountain Ruby, Southeast Ruby Conference and Boulder Ruby Group If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Vitamix Blenders Dr. Rhonda Patrick micronutrient smoothie ElixirConf Elixir Erlang Rocky Mountain Ruby Southeast Ruby Boulder Ruby Group Drip RefactoringRails.io

21 September 2017


16: Going Viral and Customer Driven Products

16: Going Viral and Customer Driven Products

Ben and Derrick are back from vacation this week are feeling refreshed. Ben tweeted something that went viral and has dealt with some people’s misinterpretation and bias. He is working on hiring a designer for some of the course finishing touches and is honing in on the premium tier offerings. Ben also has two side projects, Briefs and Trail Mix, that he is thinking of doing a tour about. RefactoringRails.io is set to launch the end of September. Drip has been onboarding a new developer onto the core-product team and Derrick discusses his interview and hiring process. He also shares how Drip is doing as a customer-driven product team, inspired by David Cancel’s top ten criteria in a recent Conversion Cast episode. Today’s Topics Include: Going viral and dealing with public reaction Ben’s side projects, Briefs and Trail Mix Finishing and preparing to launch Ben’s course RefactoringRails.io Hiring process at Drip Allocating time for housekeeping tasks to avoid ‘noise’ David Cancel’s top ten items to determine if you’re doing well in a customer-driven product team If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: RefactoringRails.io Briefs "Trail Mix Drip Conversion Cast - Episode with David Cancel Drift

7 September 2017


15: Lessons in Scaling SaaS

15: Lessons in Scaling SaaS

This week Ben is on vacation and Derrick is here to share some fresh knowledge behind the scenes at Drip. They’re experimenting at Drip with how to scale the system to handle more customers and what changes are needed to make the architecture support all their customers and future large customers in the sales pipeline. Derrick goes over his team’s recent brainstorming session and plans to repeat the exercise for more subsystems at Drip. Today’s Topics Include: The many seasons of scaling a SaaS business Starting with simplistic architecture Arriving at bottlenecks and incremental evolution of the system How to have brainstorming sessions with engineers Reevaluating assumptions and tradeoffs If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Drip

31 August 2017


14: The Power of Simplicity

14: The Power of Simplicity

This week Ben has been managing his projects and to-do list with OmniFocus, which helps as his business and stress level continue to increase. He has outlined and will be recording his last video about form objects and is glad to be approaching the finish line on the course. He also experimented with adding a Call to Action button in his emails but wants to get more data comparing metrics to get the best strategy with different email clients. Derrick has been in the trenches working on scaling Drip this week by strategizing on architecture with the backend team. They have onboarded one of their biggest customers and are working with them to segment and filter subscribers to be more efficient. He discussed the importance of legacy code base and how it is re-invented and improved over time. While their backend has become more complicated and fast-paced, he and his team are committed to keeping high quality and continue shipping things out quickly. Today’s Topics Include: Working around a schedule and dealing with notifications Email data metrics and call to action tests Scaling backend architecture Brain-dumping to address issues Defining legacy in a code base and continuous re-evaluation Consistency in a code base Moving fast and increasing complexity while maintaining high quality If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: RefactoringRails.io Drip Omnifocus Pocket Final Cut Pro Github AdBlock

24 August 2017


13: Crossing the Chasm

13: Crossing the Chasm

This past week Ben has hit a mental slump in the final phase of his course. However, he is moving through it and will be recording another video today towards the new final goal of 8 total course videos. He is tentatively scheduling the course launch for the first week of September. He has also scheduled his first Meetup event of his tour, on September 13th at the Atlanta Ruby Users Group. Derrick brings up a recent Giant Robots podcast episode with Seth Godin, which talks about the dips experienced in business, “crossing the chasm” by moving from innovators into the mass market, and the personal transparency of the host Chad Pytel. Derrick relates what he heard to the phase Drip is in at the moment, and where he wants it and himself to go in the future. Today’s Topics Include: Finishing a project and psychological momentum Ben’s Ruby Meetup tour and launch sequence Giant Robots podcast episode with Seth Godin Being real and transparent as a podcaster Reflecting on business and choosing what market you want to serve Drip’s current stage and market Deciding the way you want to work while growing a company Innovation versus mass market Admin and internal dev tools If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: RefactoringRails.io Drip Atlanta Ruby Users Group Giant Robots podcast Seth Godin Episode Thoughtbot Crossing the Chasm by Geoffrey Moore Scaling SaaS

17 August 2017


12: Free Trials and Live Streaming Video Lessons

12: Free Trials and Live Streaming Video Lessons

This week Ben discusses his experiment live-streaming a practice recording of his next video. He received helpful feedback and saw a spike in email subscribers, so it was very successful. He now has six videos done in the course and is considering a multiple tiered pricing model for his course release. On a personal note he has decided to move from his apartment in downtown Boston and will soon relocate to a hip area outside of the city. His goal this month is to finish and launch the course before the move and start his Meetup tour in September. Derrick has been working on the Drip free trial to help clarify the product plans. He debated split testing this move, but in talking to his team they decided to just go for it. There was a bit of user confusion during the onboarding workflow for the free plan so this should clear things up. On the backend, this week the team is upgrading to Rails 5 and working to replace Capistrano with Amazon’s CodeDeploy. Derrick is also reviewing his code review processes and Ben weighs in on his thoughts on this problem. Today’s Topics Include: Regular yoga practice and posture Ben’s live-stream experience and results Relocating living space and minimalist lifestyles Multiple tiered course pricing models Changes to the Drip free trial program Keeping up with Rails versions Amazon CodeDeploy Code review processes If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: RefactoringRails.io Drip Twitch Ruby on Rails Capistrano Amazon CodeDeploy Heruko

10 August 2017


11: The Founders Dilemma

11: The Founders Dilemma

Derrick is coming back from a much-needed vacation in San Francisco and enjoyed walking tours thanks to the Detour app. He returns refreshed and was able to get back into the swing of things and even into his yoga classes. It was also officially announced this week that Clay Collins, Founder and CEO of LeadPages is stepping down and will be replaced by former COO John Tedesco. Clay had a great amount of self-awareness in his announcement and this brings up the topic of The Founder’s Dilemma and best management practices for startups. Last week Ben published a new sample course video on speeding up slow test suites. He is improving his recording and editing processes using Final Cut Pro. He is now working on the fifth video and nearing the halfway point on the course. He is also going to try live streaming the practice run of his next video and incorporating early feedback into the final recording. To market the course, he is looking forward to traveling the country and speaking at Ruby meetups. Today’s Topics Include: Taking real vacations and disconnecting from work in order to recharge The restorative power of yoga Company history and leadership changes at Leadpages The Founder’s Dilemma and knowing what you are optimizing for Freedom, wealth and ambition as a startup founder Outsourcing and the value of having a personal assistant Video editing processes, software and live streaming Ruby meetup tours as a marketing tool If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: RefactoringRails.io Drip Detour - guided walking tour app Leadpages The Founder’s Dilemma by Noam Wasserman Rich vs. King in the Real World: Why I sold my company by Jason Cohen Don’t Build a Business Because You Want Freedom by Jeff Goins Startups for the Rest of Us podcast Final Cut Pro

3 August 2017


10: Dynamic Website Personalization with Brennan Dunn

10: Dynamic Website Personalization with Brennan Dunn

Today Ben’s guest is Brennan Dunn, co-founder of RightMessage, a tool that allows you to personalize your website based on user information and behavior. This allows you to customize your messaging to each user’s unique story and needs. Brennan explains the value of customer targeting, shares his ambition for Right Message, his personal journey and advice for other software startups along the way. Today’s Topics Include: Brennan’s experiences and genesis of RightMessage Targeting with ads and website content Technical details on customer targeting Most profitable targeting activity Onboarding hesitant customers with course material Current status and future plans for RightMessage If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: RightMessage Double Your Freelancing Drip Pro Tools Master Drip Email Automation Course - Brennan Dunn Bounce Exchange Webpack Planscope Churn Buster Baremetrics Open Startups

27 July 2017


9: Deep Thinking and Finding Your Groove

9: Deep Thinking and Finding Your Groove

This week Ben is adjusting to jet-lag from his travels to Las Vegas and Martha’s Vineyard last week. He did however manage to release another episode of his sample campaign that was recorded before his vacation, so he is making good progress with the course. He has a welcome to the mailing list campaign featuring the three sample videos, and has nailed down a pacing and difficulty level for recording each video. He will finish a fourth video in the next few days and is thinking of pre-launching the course once at least half has been recorded. Derrick is celebrating and reflecting on the one year anniversary of the Drip acquisition. They have gone from 3 to 10 engineers in the last year, and have really hit their stride in productivity. Their free plan has launched, which has only been feasible since receiving funding, and it has been a successful market strategy. Overall he has been a bit stressed at managing the large scale use of their platform while planning for future growth. Today’s Topics Include: Falling out of good routines while traveling Releasing evergreen content instead of broadcasts Thinking about non-native English speaking viewers when recording videos Celebrating the Drip one year anniversary of acquisition Managing current workloads while scaling and also planning for growth Scaling challenges in SaaS businesses Keeping mental and physical health up during stressful times Getting used to using the Amazon Echo If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: RefactoringRails.io Drip Scaling SaaS Ben Orenstein on Twitter Derrick Reimer on Twitter

20 July 2017


8: Different Paths to Software Development with Ian Nance from Drip

8: Different Paths to Software Development with Ian Nance from Drip

This episode Ben is on vacation and we have a guest, Ian Nance, a Drip team member here to talk about his backstory and how he got into software development. Ian has an interesting story about how he started programming later in life and his work experiences. Join us as he shares his journey and some great advice for beginners in the field. Today’s Topics Include: Ian’s background and start in programming Going from online and in-person courses to working on the job Troubleshooting customer problems and on-the-job learning Continuing education and keeping up with technology Advice to beginners in the programming world If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Drip Udacity Elm Elixir

13 July 2017


7: Learning from Successes, and Failures

7: Learning from Successes, and Failures

This week Ben has been trying new productivity techniques and studying different systems of workflow. He finished a new course video on Page Objects, and has sketched out a second video to hit his pre-vacation goal. He also released a re-edit of his first video, and is strategizing on how much material to drip out in promoting the course. He’s thinking of approaching his course videos similar to how he would approach giving a talk, and giving each one more practice before going live. Derrick had a technical issue over the weekend, which his team worked out and stabilized. He has decided to adopt a “blameless post-mortem” approach to problem-solving going forward. The incident ended up turning into a learning exercise and they are going to focus on building a playbook as a resource in the future. Today’s Topics Include: Testing work productivity methods Planning a drip release of a video course Improving video recording prep and practice Pacing and speed of course videos A “blameless post-mortem” approach to problem solving Building documentation to help teams respond to technical issues If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Deep Work by Cal Newport RefactoringRails.io Refactoring from Good to Great - Aloha Ruby Conference talk by Ben Orenstein Blameless post-mortems

6 July 2017


6: Refactoring Rails and Shareable Workflows

6: Refactoring Rails and Shareable Workflows

On today’s episode we discuss Ben’s release of the first video in his Refactoring Rails course, on the benefits of following Rest in Rails applications. He goes over how he produced the video, sent it out and the feedback he got on his initial release. He now knows the rough format he wants to follow for the course, and he is still figuring out how many modules that would include. He is getting ready to release a final polished version, and has ordered some better audio recording equipment for future videos. His goal for next week is to release two more videos. Derrick has been shipping even more this week, and has seen a huge improvement in his workflow by reducing the notifications on GitHub. His team is adjusting to a more efficient way of working instead of push notifications. He shipped out a widget to embed sharable workflows within a website that includes affiliate links. He and his team have also been strategizing about their back-end infrastructure and scaling their Drip delivery system. Today’s Topics Include: Ben’s Refactoring Rails course first course video release and feedback The goals for the course format, length and possible supplementary materials The tools and skills included in the video course that could be expanded Releasing his video to a mailing list and ways to get more traffic Reflecting on doing the course solo and how he’s liking the co-working space Derrick’s improving work clarity by reducing GitHub notifications by unwatching of main drip repository Creating a new system for the team to be most productive Sharable workflows and the new embed widget Improving scale for Drip delivery system and looking for new infrastructure systems If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: RefactoringRails.io Working Effectively with Legacy Code by Michael Feathers Test-Driven Rails course on Upcase Spring Upcase courses Audio-Technica ATR2100 Drip Amazon DynamoDB SendGrid Amazon API Gateway How I Built This podcast by NPR

29 June 2017


5: Ways We Maintain Focus

5: Ways We Maintain Focus

Today we talk about how Ben just launched his new landing page and set up the domain for his new Rails video course. Ben’s also feeling pretty good about being committed to the first thing and now it’s full steam ahead with the video course. Now it is time to put together a marketing and list-building plan and start organizing the content and getting feedback. Ben feels it will be a compelling video course and plans to go after pre-orders. Derrick has been shipping stuff this week. He just rediscovered the pulse tab on GitHub which gives a nice summary of what they have done over the week. They are making improvements to the subscriber page, and they have added global snippets. They have more refinements coming such as search when there are many items in a drop-down list. Derrick has had a lot going on, so he is turning off some of his notifications to avoid overload when he is trying to work. Today’s topics include: Ben is beginning to focus on Rails in particular for his new video course. The next step is driving as many people to the page as possible to collect emails. Then he is putting together a working table of contents and getting feedback on that by reaching out to people who are interested. Going after teams for video course projects. Possible ways to structure things to appeal to teams that would purchase the course. How it’s nice to have someone else you know nearby while working and the benefits of sharing co-working space. Derrick has been making a lot of programming improvements and refinements to Drip. Convenience and flexibility of using plugins. Preventing things from getting lost in the noise. Dealing with notification overload and letting go a little bit. If you’re enjoying the show please give us your ratings and reviews in iTunes. Links and resources: Drip RefactoringRails.io FormKeep GitHub/Pulse

22 June 2017


4: Always Talk With the Decision Maker

4: Always Talk With the Decision Maker

In this episode, Derrick is broadcasting from California as he visits his family. Ben went to Vermont last week and quickly realized how relaxing it is to be outside and see greenery. Such a different feel from the tension in the city. Ben has been chatting with a couple of people about consulting as a revenue officer. He had an interesting chat with someone but their visions just weren’t aligned in terms of value and compensation. Also it turned out this person wasn’t the decision maker, and the founder wasn’t as agreeable to Ben’s terms. Lesson learned - always talk to the decision maker. Ben is also struggling with whether he really wants to be involved in consulting. He may want to just focus on his product. Enjoy the show. Today’s topics include: Buying Apple laptops and how tricky it can be. When interviewing and making offers it’s always a good idea to talk to the decision maker. Launching info products and being smart about the automation and marketing. Ben’s idea for a SaaS starter kit has been getting positive feedback. Derrick shipped a new Drip feature called sharing workflows. There will be a gallery with workflows that people can just click on and use. Derrick is making good progress and writing less code, so that he won’t be the bottleneck on his team. It’s motivating to have people focused on their area of expertise. Challenges of getting new hires and team members up to speed. Links and resources: Drip Leadpages Thoughtbot WWDC2017 SunSpider JavaScript Benchmark Test Brennan Dunn How to exit the Vim editor Podcast Motor

12 June 2017


3: New Pricing Strategies

3: New Pricing Strategies

Updates and pricing strategies highlight today’s episode. Ben did yoga this morning, and he is feeling relaxed as he is settling in with his new lifestyle. Next week Ben is closing his first part-time chief revenue officer engagement. Now it’s time to come up with a contract and a pricing strategy. Derrick is looking at different pricing strategies and markets for Drip. There are so many opportunities for positioning and marketing. The extended trial free plan has created a full pipeline that converts at a healthy rate. Derrick also spent his Memorial Day weekend playing with the programming language Elixir and learning some cool new data manipulation techniques. Enjoy the show. Today’s topics include: The startup life ups and downs and the brain body connection. Doing work as an independent creative professional and how contracts help get freelancers paid. How reaching out to your email list can lead to interesting opportunities. Pricing for services and how to price based on value. Different pricing packages with tiers and bundling strategies. Problems with offering free plans and support and scale issues. When product features increase so do support obligations. People being nice on the Internet. Content hubs or Websites. Learning Elixir. Links and resources: Podcast Motor F*ck You, Pay Me by Mike Monteiro Patrick McKenzie @Patio11 Drip Julian Shapiro Elixir Phoenix Framework Programming Phoenix

5 June 2017


2: From Good to Great

2: From Good to Great

Welcome to the Art of Product podcast. Derrick is rocking his “I ♥ yoga” shirt because he started practicing yoga at a studio down the street. He also gives us an update on new changes and features at Drip. Derrick was inspired by Ben’s newsletter and decided to work on his own newsletter, which gave him a great opportunity to use his own product. Ben is discovering that unemployment is a roller coaster. His stress level has been about 5X his normal baseline stress level. He started working at the co-working space and attending mixer events. He is emailing people on his list and sharing his ideas to get feedback for possible products for him to work on. Ben has been reflecting on how people and relationships make him shine and is considering finding a co-founder for his product. Today’s topics include: How the metabolic rate of connective tissue is a 5th of muscle tissue. Drip has refreshed their marketing page and is working on adding product. How responsive the people at Drip are with feature requests and customer inquiries. Ben’s top 3 ideas are refactoring his “From Good to Great” talk into a course, a book called The Tiny Book for Faster Rails, and a Rails starter kit. How it is difficult to plan out everything that is going to happen in the future. Ways to find support for Ben’s work and projects. Being open to changing your mind. How awesome and supportive Ben’s online community has been. Links and resources: Ben’s Newsletter Drip Leadpages Thoughtbot From Good to Great a talk by Ben Orenstein Sherry Walling

1 June 2017


1: Welcome to The Art of Product

1: Welcome to The Art of Product

Welcome to the Art of Product podcast. This is episode 1, and just the beginning of the journey. This is a show with Ben Orenstein formerly from thoughtbot and Drip co-founder Derrick Reimer. Ben recently quit his job at thoughtbot, and is now focusing on what he is going to do next. Stay tuned. This is going to be a fun journey. Ben and Derrick talk about venturing out on one’s own and starting a new business. Ben has found a new co-working space in Boston. He is even trying a shared desk for interaction with people and to avoid the work-at-home isolation. Keeping focused and staying on task are important issues. Hopefully Omnifocus will help with that. Derrick is excited about the future and growth of Drip. Today’s topics include: How to stay focused when setting up a new business and do more than just the fun things. The importance of having built-in structure when working on your own business. How work can creep into your entire life without the luxury of a set schedule. Putting travel off while getting established. Going from income rate to a burn rate. Having a financial buffer to provide flexibility with establishing a new business. Brennan Dunn just spoke at Leadpages, he also happened to be Drip user number 5 and he pushed the product with his innovator feedback. Derrick enjoyed talking with a power user like Brennan. How Drip is scaling and hiring with the backend and the core product or feature team. Links and resources: CIC Boston Omnifocus Drip Leadpages Thoughtbot Brennan Dunn

1 June 2017

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