The Art of Product is a podcast chronicling the journeys of two software entrepreneurs (Ben Orenstein and Derrick Reimer) building startups. Discussions span from the technical realm to the business side and everything in between.
August 31st, 2017 | 6 mins 51 secs
This week Ben is on vacation and Derrick is here to share some fresh knowledge behind the scenes at Drip. They’re experimenting at Drip with how to scale the system to handle more customers and what changes are needed to make the architecture support all their customers and future large customers in the sales pipeline. Derrick goes over his team’s recent brainstorming session and plans to repeat the exercise for more subsystems at Drip.
August 24th, 2017 | 42 mins 5 secs
This week Ben has been managing his projects and to-do list with OmniFocus, which helps as his business and stress level continue to increase. He has outlined and will be recording his last video about form objects and is glad to be approaching the finish line on the course. Derrick has been in the trenches working on scaling Drip this week by strategizing on architecture with the backend team. They have onboarded one of their biggest customers and are working with them to segment and filter subscribers to be more efficient.
August 17th, 2017 | 32 mins 35 secs
This past week Ben has hit a mental slump in the final phase of his course. However, he is moving through it and will be recording another video today towards the new final goal of 8 total course videos. Derrick brings up a recent Giant Robots podcast episode with Seth Godin, which talks about the dips experienced in business, “crossing the chasm” by moving from innovators into the mass market, and the personal transparency of the host Chad Pytel.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.