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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• (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?

• MicroConf Europe ┃Reykjavik, Iceland · Sept 21–23, 2026
• Tailwind CSS
• Tailwind Labs
• ui.sh
• Adam's Morning Walk Podcast
• My Body Tutor
• Adam Wathan (@adamwathan)┃X

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!

Subscribe & Review: iTunes | Spotify

What do you do when a collaborator takes your idea and builds a competing product?

In this episode, Rob Walling is joined by fan favorite Jordan Gal to answer listener questions on some of the trickiest challenges founders face. They cover financing decisions like using debt to bridge cash flow gaps, competing in markets flooded with vibe-coded apps, and what to do when a collaborator takes your idea and runs with it.

Want to get your question answered? Submit it here for a future episode.

This episode is brought to you by Mercury

Mercury is the banking solution I use across my businesses, from my personal single-member LLC to MicroConf and TinySeed.

Traditional banking forces you to duct-tape tools together and work around slow, clunky processes. Mercury gives me a clean dashboard that shows exactly where each business stands at a glance.

The interface is simple enough for daily banking and paying invoices, but powerful enough to handle multi-step approval workflows for large transfers.

There's a reason more than 300,000 entrepreneurs have made the switch. It's free to get started with no in-person visits and no minimum balance.

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Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC.

• (3:50) – Jordan Gal on Rosie's multichannel launch
• (8:01) – Investing cash in slow-moving healthcare markets
• (10:32) – Using debt or credit against signed contracts
• (16:48) – Competing in crowded markets with vibe-coded apps
• (24:34) – Should you offer advisory shares to design partners?
• (30:38) – Selling to problem-aware but not solution-aware audiences
• (37:35) – When a collaborator steals your startup idea

• TinySeed SaaS Institute
• Stripe Capital
• The Play Bigger Book
• The SaaS Playbook
• Rob Walling's Books
• Rob Walling's Newsletter
• Rosie AI
• Jordan Gal (@JordanGal) | X

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!

Subscribe & Review: iTunes | Spotify

Is AI really killing B2B SaaS, or is it just subscription software by another name?

In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into the market panic around SaaS stocks, whether AI models are actually getting better, ChatGPT's move into advertising (and Anthropic's spicy response), and the explosion of OpenClaw. They also tackle QSBS and when SaaS acquisitions shift from asset to stock purchases.

This episode is brought to you by Mercury

Mercury is the banking solution I use across my businesses, from my personal single-member LLC to MicroConf and TinySeed.

Traditional banking forces you to duct-tape tools together and work around slow, clunky processes. Mercury gives me a clean dashboard that shows exactly where each business stands at a glance.

The interface is simple enough for daily banking and paying invoices, but powerful enough to handle multi-step approval workflows for large transfers.

There's a reason more than 300,000 entrepreneurs have made the switch. It's free to get started with no in-person visits and no minimum balance.

Apply online in minutes at mercury.com.

Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC.

If you’ve got a strong vision but no technical partner, you need more than a “vibe-coded” MVP, you need a real foundation.

That’s where Designli comes in. Their two-week SolutionLab Prototyping Sprint pairs you with a product owner, designer, and developer to turn your idea into a beautiful, clickable prototype you’ll be proud to show investors or early users.

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• (3:52) – M&A guide for B2B SaaS founders
• (6:35) – QSBS and asset vs. stock purchase thresholds
• (9:25) – Is AI killing B2B SaaS?
• (16:27) – Are AI models noticeably better than a year ago?
• (17:27) – ChatGPT vs. Claude: real-world experiences
• (26:17) – ChatGPT ads and Anthropic's Super Bowl response
• (29:34) – The opportunity for SaaS founders in new ad networks
• (32:29) – OpenClaw: hype or substance?

• MicroConf US April 12-14, 2026 · Portland, Oregon
• Discretion Capital’s M&A Guide
• TinySeed SaaS Institute
• AI is Killing B2B SaaS by Namanyay Goel
• OpenClaw is What Apple Intelligence Should Have Been by Jake Quist
• Rob Walling @robwalling | X
• Einar Vollset @einarvollset | X
• Tracy Osborn (tracymakes) | Blue Sky

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...