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.

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  • 31: Mental Health for Startup Founders with Sherry Walling

    February 8th, 2018  |  23 mins 54 secs

    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.

  • 30: Nailing an Interview, and the New Drip Design

    January 25th, 2018  |  40 mins 46 secs

    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.
    In Drip news, Drip recently got a brand refresh, including a new logo, marketing site, color palette, new messaging, app skin, and more.

  • 29: Fitness and Code Quality in 2018

    January 11th, 2018  |  54 mins 38 secs

    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. Ben is launching the second cohort of The 30-Day Code Quality Challenge this week, and this cohort is even larger than the first.

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

    December 28th, 2017  |  1 hr 9 mins

    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.

  • 27: 30 Day Code Quality Challenge, and Elm Development

    December 14th, 2017  |  51 mins 15 secs

    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. 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.

  • 26: Optimizing Team Structures

    December 7th, 2017  |  48 mins 22 secs

    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.

  • 25: Chaos, and Growing an Engineering Team

    November 30th, 2017  |  1 hr 42 secs

    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. 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.

  • 24: Tailwind CSS with Adam Wathan

    November 17th, 2017  |  48 mins 15 secs

    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.

  • 23: Refactoring Rails Launch Breakdown

    November 9th, 2017  |  25 mins 33 secs

    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

  • 22: Finishing the Year Strong

    November 2nd, 2017  |  26 mins 46 secs

    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.
    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.

  • 21: Launching Refactoring Rails

    October 26th, 2017  |  35 mins 40 secs

    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. 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.

  • 20: The Ups and Downs of Working From the Road

    October 19th, 2017  |  24 mins 26 secs

    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. 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.

  • 19: Gourmet Ruby with Avdi Grimm

    October 12th, 2017  |  30 mins 58 secs

    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.

  • 18: Preparing for Black Friday

    September 28th, 2017  |  27 mins 13 secs

    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. 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.

  • 17: Launch Planning and Speaking at Conferences

    September 21st, 2017  |  32 mins 33 secs

    Ben is coming back from a restorative vacation in Martha’s Vineyard and loves the vibe there. 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. 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.

  • 16: Going Viral and Customer Driven Products

    September 7th, 2017  |  44 mins 37 secs

    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. 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.