What happens when AI starts competing with your open source business?

In this episode, Rob Walling sits down with Adam Wathan, co-founder of Tailwind CSS, for a candid conversation about the dramatic revenue decline that forced Tailwind Labs to lay off most of their team. Adam shares the hard lessons learned from running a business based on one-time purchases, why he didn't see the slowdown coming, and how an honest podcast episode accidentally turned everything around.

Then they switch gears entirely to talk about founder fitness: how Adam lost 70 pounds, his 15-minute weighted vest workouts, and why tracking strength gains can be more motivating than watching the scale.

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Topics we cover:

(4:43) – Adam's history with Tailwind CSS
(5:17) – Revenue decline and the "boiling frog" problem
(8:30) – Making the hard decision to lay off the team
(11:39) – The viral podcast episode and unexpected sponsors
(13:07) – Should Tailwind have used recurring revenue?
(21:20) – Enterprise pricing and team licenses
(25:47) – What's next: Ui.sh and swimming downstream with AI
(27:40) – Founder fitness: 15-minute weighted vest circuits
(33:01) – Tracking strength gains as motivation
(39:13) – Did getting fit make Adam a better founder?

Links from the show:

If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from you!

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Episode 825 | Talking Tailwind CSS and Founder Fitness (with Adam Wathan)

Startups For the Rest of Us

Episode 825 | Talking Tailwind CSS and Founder Fitness (with Adam Wathan)