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


  • 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.

  • 91: Feeling Superhuman with Rahul Vohra

    June 13th, 2019  |  41 mins 44 secs

    Today’s guest is Rahul Vohra, co-founder and CEO of Superhuman.

  • 90: The Mom Test with Rob Fitzpatrick

    May 30th, 2019  |  47 mins 43 secs

    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.

  • 89: Go Big, or Stay Small?

    May 23rd, 2019  |  35 mins 37 secs

    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.

  • 88: Will They Make the Jump?

    May 9th, 2019  |  29 mins 30 secs

    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?

  • 87: Meta Podcasting

    May 2nd, 2019  |  47 mins 11 secs

    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.

  • 86: The Importance of Paying Customers in Product Feedback

    April 25th, 2019  |  51 mins 36 secs

    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.

  • 85: The Hype Is Real

    April 18th, 2019  |  33 mins 10 secs

    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.

  • 84: Developer Mindset with Brian Casel

    April 11th, 2019  |  40 mins 38 secs

    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.