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


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

    October 17th, 2019  |  26 mins 57 secs

    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.

  • 106: Creating Growth Key Metrics

    October 10th, 2019  |  34 mins 17 secs

    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.

  • 105: Exploring Freemium

    October 3rd, 2019  |  24 mins 21 secs

    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.

  • 104: Tiny Conferences, and Business Growth Challenges

    September 26th, 2019  |  32 mins 48 secs

    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.

  • 103: Code Quality and Balancing TDD

    September 12th, 2019  |  35 mins 19 secs

    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.

  • 102: Single Sign On (SSO) for Tuple?

    September 5th, 2019  |  27 mins 7 secs

    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.

  • 101: Mentorship Momentum with Matt Wensing of SimSaaS

    August 29th, 2019  |  32 mins 16 secs

    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.

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

    August 22nd, 2019  |  1 hr 2 mins

    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!

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

    August 15th, 2019  |  25 mins 34 secs

    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!

  • 98: Adam Covers for Derrick

    August 8th, 2019  |  37 mins 7 secs

    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!

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

    August 1st, 2019  |  28 mins 40 secs

    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 She describes what it takes to create a customer messaging tool.

  • 96: Tuple Official Launch and Taking Time to Unplug

    July 25th, 2019  |  32 mins 44 secs

    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!

  • 95: What Really Happened to Screenhero

    July 11th, 2019  |  43 mins 56 secs

    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!

  • 94: Seeking Clarity

    July 4th, 2019  |  34 mins 28 secs

    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.

  • 93: Company of One with Paul Jarvis

    June 27th, 2019  |  48 mins 48 secs

    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.

  • 92: Slack Leaves the Market

    June 20th, 2019  |  30 mins 13 secs

    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.