The Art of Product

Ben and Derrick chat weekly about building software companies.

About the show

The Art of Product is a podcast chronicling the journeys of two entrepreneurs building software companies. Hosted by Ben Orenstein and Derrick Reimer.

The Art of Product on social media


  • 139: Efficiency Starts With Groceries

    July 30th, 2020  |  26 mins 48 secs

    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.

  • 138: That's Not How Cults Work

    July 23rd, 2020  |  36 mins 13 secs

    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 incentives Tuple hires. As Tuple keeps growing quickly, Ben continues to navigate decision fatigue and transitioning from individual contributor to business operator.

  • 137: Approved!

    July 16th, 2020  |  30 mins 54 secs

    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.

  • 136: Feedback Is Everything

    July 9th, 2020  |  33 mins 17 secs

    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.

  • 135: Do We Really Need An Office?

    July 2nd, 2020  |  32 mins 16 secs

    Derrick is driving toward the first milestone of using Mighty Cal 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.

  • 134: Introducing Mighty Cal

    June 25th, 2020  |  31 mins 49 secs

    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.

  • 133: Perfect Is The Enemy Of Good

    June 18th, 2020  |  31 mins 26 secs

    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.

  • 132: Digging a Moat

    June 11th, 2020  |  27 mins 22 secs

    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.

  • 131: Making Calculated Bets

    May 21st, 2020  |  33 mins 38 secs

    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.

  • 130: Certainty Isn't The Goal

    May 14th, 2020  |  30 mins 21 secs

    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.

  • 129: Remember When Software Came on Floppy Disks?

    April 30th, 2020  |  27 mins 2 secs

    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.

  • 128: One Day At A Time

    April 23rd, 2020  |  31 mins 31 secs

    Derrick is enjoying work the last week by taking joy in setting and achieving small goals each day.

  • 127: A Tuple Growth Spurt

    April 9th, 2020  |  27 mins 34 secs

    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.

  • 126: Tuple Takes Over

    April 2nd, 2020  |  39 mins 4 secs

    Ben and Derrick hang out with Tuple co-founders Spencer and Joel and talk shop.

  • 125: Keeping Things in Perspective

    March 26th, 2020  |  26 mins 59 secs

    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.

  • 124: Back After A Break

    March 19th, 2020  |  41 mins 32 secs

    Suntans and sunburns aside, Derrick’s winter escape to Mexico provided meaningful ideas and perspective on StaticKit. By reading, Competing Against Luck, 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.