Navigate the AI Frontier Every Month With Founder Peers

by | Sep 19, 2025

Three weeks ago at our Practical Founders Summit, I watched something powerful happen:

A founder shared how their new AI feature, which is both cool and useful, helped them double their demo-to-close rate in one quarter.

Another revealed how they vibe-coded a prototype and then shipped a useful add-on product that they charge for.

A third explained how AI helped them double SEO traffic and double qualified demo leads so far this year.

The gap between theory and practice is massive right now.

Generic playbooks speak to averages. Investor advice comes through an investor lens. ChatGPT gives you what worked for someone else, somewhere else.

But sitting with the same group of serious, bootstrap-minded SaaS founders every month? That’s where the real intelligence lives.

SaaS founders are quietly figuring out what actually works—and what spectacularly fails—in real businesses with real customers.

In our Practical Founders peer groups for bootstrapped SaaS CEOs, founders building toward $10M ARR share the questions that actually matter:

  • Why did that AI pricing strategy backfire in month two?
  • How are you handling regulatory pushback in healthcare/finance?
  • What’s your honest assessment—are you ahead or behind this month?
  • Which “AI-native” competitors are real threats vs. just noise?

We’re navigating this shift together, one month at a time.

Because the founders who win the AI transition won’t be the ones with the best theories—they’ll be the ones with the best intelligence network.

Learn about Practical Founders CEO Peer Groups.

Greg Head posted this on LinkedIn on September 19, 2025.

Check out the comments and join the discussion on LinkedIn.

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