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


  • 12: Free Trials and Live Streaming Video Lessons

    August 10th, 2017  |  38 mins 53 secs

    This week Ben discusses his experiment live-streaming a practice recording of his next video. He received helpful feedback and saw a spike in email subscribers, so it was very successful. Derrick has been working on the Drip free trial to help clarify the product plans. He debated split testing this move, but in talking to his team they decided to just go for it.

  • 11: The Founders Dilemma

    August 3rd, 2017  |  33 mins 4 secs

    Derrick is coming back from a much-needed vacation in San Francisco and enjoyed walking tours thanks to the Detour app. He returns refreshed and was able to get back into the swing of things and even into his yoga classes. Last week Ben published a new sample course video on speeding up slow test suites. He is improving his recording and editing processes using Final Cut Pro. He is now working on the fifth video and nearing the halfway point on the course.

  • 10: Dynamic Website Personalization with Brennan Dunn

    July 27th, 2017  |  40 mins 50 secs

    Today Ben’s guest is Brennan Dunn, co-founder of RightMessage, a tool that allows you to personalize your website based on user information and behavior. This allows you to customize your messaging to each user’s unique story and needs. Brennan explains the value of customer targeting, shares his ambition for Right Message, his personal journey and advice for other software startups along the way.

  • 9: Deep Thinking and Finding Your Groove

    July 20th, 2017  |  24 mins 26 secs

    This week Ben is adjusting to jet-lag from his travels to Las Vegas and Martha’s Vineyard last week. He did however manage to release another episode of his sample campaign that was recorded before his vacation, so he is making good progress with the course. Derrick is celebrating and reflecting on the one year anniversary of the Drip acquisition. They have gone from 3 to 10 engineers in the last year, and have really hit their stride in productivity.

  • 8: Different Paths to Software Development with Ian Nance from Drip

    July 13th, 2017  |  29 mins 33 secs

    This episode Ben is on vacation and we have a guest, Ian Nance, a Drip team member here to talk about his backstory and how he got into software development. Ian has an interesting story about how he started programming later in life and his work experiences. Join us as he shares his journey and some great advice for beginners in the field.

  • 7: Learning from Successes, and Failures

    July 6th, 2017  |  38 mins 42 secs

    This week Ben has been trying new productivity techniques and studying different systems of workflow. He finished a new course video on Page Objects, and has sketched out a second video to hit his pre-vacation goal. Derrick had a technical issue over the weekend, which his team worked out and stabilized. He has decided to adopt a “blameless post-mortem” approach to problem-solving going forward.

  • 6: Refactoring Rails and Shareable Workflows

    June 29th, 2017  |  33 mins 53 secs

    On today’s episode we discuss Ben’s release of the first video in his Refactoring Rails course, on the benefits of following Rest in Rails applications. He goes over how he produced the video, sent it out and the feedback he got on his initial release. Derrick has been shipping even more this week, and has seen a huge improvement in his workflow by reducing the notifications on GitHub. His team is adjusting to a more efficient way of working instead of push notifications.

  • 5: Ways We Maintain Focus

    June 22nd, 2017  |  33 mins

    Today we talk about how Ben just launched his new landing page and set up the domain for his new Rails video course. Derrick has been shipping stuff this week. He just rediscovered the pulse tab on GitHub which gives a nice summary of what they have done over the week.

  • 4: Always Talk With the Decision Maker

    June 12th, 2017  |  30 mins 42 secs

    In this episode, Derrick is broadcasting from California as he visits his family. Ben went to Vermont last week and quickly realized how relaxing it is to be outside and see greenery. Such a different feel from the tension in the city.
    Ben has been chatting with a couple of people about consulting as a revenue officer. He had an interesting chat with someone but their visions just weren’t aligned in terms of value and compensation. Also it turned out this person wasn’t the decision maker, and the founder wasn’t as agreeable to Ben’s terms. Lesson learned - always talk to the decision maker. Ben is also struggling with whether he really wants to be involved in consulting. He may want to just focus on his product. Enjoy the show.

  • 3: New Pricing Strategies

    June 5th, 2017  |  33 mins 14 secs

    Updates and pricing strategies highlight today’s episode. Ben did yoga this morning, and he is feeling relaxed as he is settling in with his new lifestyle. Next week Ben is closing his first part-time chief revenue officer engagement. Now it’s time to come up with a contract and a pricing strategy.

  • 2: From Good to Great

    June 1st, 2017  |  35 mins 13 secs

    Welcome to the Art of Product podcast. Derrick is rocking his “I ♥ yoga” shirt because he started practicing yoga at a studio down the street. He also gives us an update on new changes and features at Drip. Derrick was inspired by Ben’s newsletter and decided to work on his own newsletter, which gave him a great opportunity to use his own product.

    Ben is discovering that unemployment is a roller coaster. His stress level has been about 5X his normal baseline stress level. He started working at the co-working space and attending mixer events. He is emailing people on his list and sharing his ideas to get feedback for possible products for him to work on. Ben has been reflecting on how people and relationships make him shine and is considering finding a co-founder for his product.

  • 1: Welcome to The Art of Product

    June 1st, 2017  |  33 mins 34 secs

    Welcome to the Art of Product podcast. This is episode 1, and just the beginning of the journey. This is a show with Ben Orenstein formerly from thoughtbot and Drip co-founder Derrick Reimer. Ben recently quit his job at thoughtbot, and is now focusing on what he is going to do next. Stay tuned. This is going to be a fun journey.