Ben Orenstein
Co-founder and CEO of Tuple.
Appears in 12 Episodes
Catching up
Adam and Ben are back on the mics after nine months to give an update on their lives.TimestampsLinksAdam on XBen on X
Ben and Adam review 2023
In this episode, Adam and Ben sit down to evaluate how things went in 2023 in their business and personal lives. The dudes share kind of a lot in this one! More person...
Revisiting the Tailwind Labs business model
In this episode, Adam and Ben talk through the Tailwind Labs business model. Is Tailwind UI the best way for the company to make money? Or is there a different model w...
Launching features like products
In this episode, Adam and Ben catch up on recent events at Tailwind Labs and Tuple. Adam spoke at Rails World and the impromptu Tailwind CSS meetup in Amsterdam. Ben s...
Building the right team with Jason Fried
Adam wants to start the process of growing the team at Tailwind Labs, but knowing exactly who, when, and how to hire people (and have them actually work out) is a lot ...
Hiring is hard
When you're running a small company, hiring is simultaneously your highest leverage opportunity and the scariest thing ever. In this episode, Adam and Ben share some l...
Enterprise sales for reluctant founders
Enterprise sales gets a bad rap amongst indie founders, but at Tuple it's become an important part of their business model. In this episode, Ben shares all his tips an...
Minimalist management with David Heinemeier Hansson
After over 20 years in business and despite being responsible for a larger-than-ever team, David still finds plenty of time to get his hands in the code and build new ...
Lifetime pricing is underrated
Last summer, Tailwind UI moved from selling individual content packages and upsells to a one-time purchase, lifetime access pricing model. Since then, the business has...
Revisiting "The Ideal Bootstrapped Business" with Jason Cohen
Jason Cohen’s talk “Designing the Ideal Bootstrapped Business” from 2013 is a classic in the bootstrapper canon. In this episode, Jason joins Adam and Ben to see how t...
Running your business like a band
“How come Dave Grohl is still playing guitar and writing songs and singing but I'm filling out DMCA takedown notices, answering customer support emails and responding ...
Lessons Learned in 2022-ish
Ben Orenstein (Tuple) and Adam Wathan (Tailwind CSS) are back on the mics. Today they reflect on 2022 and lessons they’ve learned. Ben has some thoughts on delegation,...