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The Art of Product

by Ben Orenstein and Derrick Reimer

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

From the show's RSS feed, refreshed Nov 6, 2026. Source feed.

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Episodes

  1. 220: Ben and Adam Wrap The Year

    The Code Quality Challenge Tuple's open CTO position Kevin Shen's Dream Studio Course

  2. 219: Ben's Friend Ben

    Ben Kuhn drops by the pod. Check out his great blog! https://www.benkuhn.net/

  3. 217: Half a Job You Love

    Aaron Francis (Tuple's Marketing Engineer) drops by for advice on his non-Tuple project, a query builder for Rails and Laravel called Refine.

  4. 216: Penelopers, Penelopers, Penelopers

    Penelope Phippen drops by and encourages Ben to set, like, even a single goal.

  5. 215: Mental Health with Dr. Sherry Walling

    Talking with Dr. Sherry Walling about dealing with mental health personally and how to help people around you who may be struggling.

  6. 213: Powered by Debt

    Tuple launched a new marketing experiment this week. Derrick is continuing work on migrating SavvyCal to new hosting infrastructure.

  7. 212: Tuple Goes Hollywood

    The Tuple team had their first filming session for the meta-documentary about their marketing experiments. Derrick is awaiting results from the latest SavvyCal funnel experiments.

  8. 211: This Is Not A Bad Reality

    Ben and Derrick catch up on all things Tuple and SavvyCal. Ben recently raised prices for Tuple. Derrick is experimenting with major funnel changes for SavvyCal.

  9. 210: Talk To Your Customers

    Derrick is launching a bunch of SavvyCal features this month, including a Close integration and meeting polls. Ben has had good experiences lately talking to customers.

  10. 209: Penelope Again-ope

    Stripe's Technical Advisor to the CTO, Penelope Phippen stops by and Ben tries to get her to divulge company secrets.

  11. 208: Prime Foot-Shooting Material

    Ben and Derrick chat through a cool new feature Tuple is shaping up. They also discuss Tuple's ambitious marketing bets.

  12. 207: Musings on Advice

    Ben and the Tuple team have hit a good shipping stride lately. Derrick and team are nearing completion on a few large SavvyCal initiatives. The guys reflect on MicroConf and the nature of dispensing advice.

  13. 206: IRL at MicroConf

    Derrick and Ben share updates from the Castos recording booth at MicroConf Growth.

  14. 205: Wathan Stops By

    Our favorite Canadian drops by to talk mobility, fancy A/V setups, what's next for Tailwind UI, and how we'll never find peace of mind.

  15. 204: Miscellanea

    Ben and Derrick riff on a variety of topics, including coffee brewing, retreats, MicroConf, design, finding business ideas, and interesting subreddits. Links: Sweet Maria's MicroConf Finding My Next Bootstrapped Business Idea The Stair Step Approach to Bootstrapping fatFIRE OneBag - The Art of...

  16. 203: The Hiring Spree

    The Tuple team has recently grown by three team members! Ben is looking forward to getting the Linux client out the door in the next month. Derrick is staying busy moving SavvyCal forward and bringing his new developer into the app.

  17. 202: The Art and Pain of Design

    Ben talks to Brian Lovin, a designer, podcaster, writer, and software tinkerer.

  18. 201: Getting Things Done with Stephen Dolan

    Ben and Derrick chat with Tuple's Chief of Staff and GTD expert, Stephen Dolan. They discuss Stephen's path from programming to sales to his current role and nerd out over methods for staying productive.

  19. 200: The 200th Episode!

    Ben recently had a Tuple team retreat. He is still in hiring mode. The Tuple product team is progressing on their Linux integration. Derrick ran a product-market fit survey for SavvyCal, and the results are... tune in to find out. He's pondering how to approach a freemium play.

  20. 199: Keeping Up With Courtland

    Ben & Derrick chat with Courtland Allen from Indie Hackers. They discuss the challenges of building a community and finding fulfillment in work, among a variety of other topics. Resources: Indie Hackers SavvyCal Tuple

  21. 198: Leaving Room To React

    Derrick and Ben catch-up about what's going on at Tuple and SavvyCal. Derrick had a fun customer experience on Twitter last week. Ben is still in hiring mode.

  22. 197: Growth Mindset

    Derrick & Ben catch up after a few weeks away for the holidays. Ben is still in hiring mode. He's considering ways to do more teaching (something he used to do a lot when he was a programmer by trade). Derrick is planning to be more intentional in fostering a growth mindset this year in business...

  23. 196: The Hedonic Treadmill

    Ben & Derrick chat about doing what you love versus doing what the business needs.

  24. 195: Metric Obsession

    Ben and Derrick catch up after a holiday break. Ben chats about his recent design hire and Stephen's promotion to Chief of Staff at Tuple. Derrick ran a successful Black Friday promo for SavvyCal and is hard at work on the Stripe integration.

  25. 194: The Future of AoP

    Ben and Derrick plan for the future of the podcast.

  26. 193: Feeling Ambitious

    Ben and Derrick chat about their ambitions for building their companies and planning for the new year.

  27. 192: This Is Not A Fire Drill

    Ben tells the story about a recent Tuple incident in production. The guys discuss how they're putting planning into action after last week's chat with Adam about Shape Up. Derrick gives an update about growth efforts for SavvyCal.

  28. 191: Shaping Up with Adam Wathan

    Ben and Derrick talk to Adam about how to effectively plan and organize work.

  29. 190: Unpacking Stripe, Continued

    Penelope Phippen is back on the show to continue the conversation from Episode 180 about how Stripe does with it does.

  30. 189: Back In The Saddle

    Ben is back home from the Vineyard and Derrick is back to 100%. Tuple is hiring a Product Designer and considering adding a bit more structure to their product planning process. Derrick recently shipped a new marketing site update

  31. 188: Priorities, Priorities

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

  32. 187: Wait, There Are How Many Time Zones?!

    Ben and team are preparing to officially designate Tuple 1.0! Derrick is working on embedding SavvyCal more deeply in customers' workflows and is digging more moats around time zone handling.

  33. 186: Investing In The Core

    Ben is back on Martha's Vineyard enjoying some partial days off. The Tuple team just shipped a major overhaul of the app internals with better performance and less CPU usage. Derrick has been doing a bit of housekeeping & maintenance work to make the core SavvyCal offering even smoother.

  34. 185: Incremental Improvements

    Ben is hanging out with two new team members in the office this week. The Tuple team is preparing to ship some big performance upgrades. Derrick launched the SavvyCal iCloud integration on Product Hunt

  35. 184: Delete Your Backlog?

    Ben and Derrick have been recharging with some vacation time the last few weeks. Ben is excited to onboard his new sales hire. Derrick shipped a Fastmail calendar integration and released a Zapier integration. The guys discuss the merits of having and tending to a backlog. Derrick could use your...

  36. 183: Soaking In Nature

    Ben is excited to onboard a new team member to help with sales and customer success. Derrick shipped iCloud integration for SavvyCal and is continuing the shipping spree. Both have recently had the opportunity to spend some time in nature on lakes and rivers.

  37. 182: Cutting Churn

    Ben hired a new engineer to help with technical support and learn the ropes on native development. Derrick is thinking about strategies for reducing churn.

  38. 181: On A Shipping Spree

    At last, Ben found someone for the sales/customer success role at Tuple. Derrick is on a shipping spree with SavvyCal.

  39. 180: Unpacking Stripe with Penelope Phippen

    Ben & Derrick chat with Penelope Phippen all about how Stripe continues to relentlessly ship high-quality software. P.S. Stripe is hiring!

  40. 179: Riffing on Reform

    Derrick is joined by Peter Suhm, founder of Reform, to share some updates and do some masterminding.

  41. 178: Why Build A Business At All?

    Ben & Derrick have an impromptu chat with Adam Wathan about all things business.

  42. 177: On The Frontier

    Ben and Derrick discuss shifting roles as their companies grow and evolve.

  43. 176: Making the Rounds

    Derrick has been sharing his story on various podcasts lately. Ben is continuing to refine his hiring process for the sales role at Tuple. Derrick is onboarding his first support hire and working on a delegated access feature for SavvyCal.

  44. 175: Ben's Meetings

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

  45. 174: Everything Is A Vision Quest

    Ben and Derrick discuss the nature of making decisions in the businesses and growing their teams.

  46. 173: Shreyas Doshi on Product Management

    Shreyas Doshi (Stripe, Twitter, Google) joins Ben and Derrick for a wide-ranging discussion on product management.

  47. 172: Markidan on Marketing

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

  48. 171: Humans Have A Lot of Drawbacks

    Ben and Derrick discuss hiring support engineers and philosophies around customer support in general. They go deep on the topic of investing in your business, diversification, and allocating assets.

About this show

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

Hosted by

Ben Orenstein and Derrick Reimer

Frequently asked questions

How many episodes does The Art of Product have?

The Art of Product has 221 episodes on PodParley. The most recent episode was published on November 6, 2026.

What is The Art of Product about?

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

How often does The Art of Product release new episodes?

The Art of Product publishes every two weeks, based on its 221 episodes since June 2017.

Who hosts The Art of Product?

The Art of Product is created and hosted by Ben Orenstein and Derrick Reimer.
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