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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