This Is a Great Fit for Some Founders. Not for Others.

There are decisions you’re making right now where you don’t have enough context and you know it. You can research. Ask your team. Talk to friends. Use AI.

But at this stage, the decisions are too specific to your business, too consequential, and too nuanced for any of that to be enough.

And you’re mostly figuring it out on your own. This is where a peer group can make a real difference. But only if it’s the right fit for you, and for right now.

This Is a Great Fit If

You’re at this stage

  • You’ve built a real SaaS or AI software business ($1M–$15M ARR) with a growing sense of what works and what doesn’t
  • You’re building it without raising significant VC funding. You are either bootstrapped or have some angel funding.
  • You’re making bigger decisions that will materially impact your company for years
  • You don’t have other founders at your level to talk to regularly
  • You want in-context perspectives, not more general content and playbooks

And this is the right time.

  • You have 2–3 decisions right now that will materially change your business, and you’re not as confident as you should be
  • You don’t have anyone who really understands your business, your goals, and what you’re trying to build
  • You’re starting to feel the weight of doing this alone.
  • You’re making progress, but slower than you want, and you know some of that is avoidable
  • You’ve made enough mistakes to know you don’t want to keep figuring everything out the hard way
Apply for a CEO Peer Group

How This Works

This is not a casual group. There are clear expectations for how members show up and contribute. That’s what makes it work.

  1. Bring Real Decisions
    When it’s your turn, you bring a real issue and frame it clearly — like you would with a board. Not vague questions. Not hypotheticals.
  2. Be Open to What You Hear
    You’ll hear perspectives you didn’t expect. You don’t have to agree with everything. But you need to be genuinely open to being challenged.
  3. Give as Much as You Get
    This works because everyone contributes. Your experience, your mistakes, your perspective — they’re valuable to the other founders in the room.
  4. Follow Through
    You make decisions. You take action. You come back and share what happened. That’s how everyone improves — including you.
  5. Keep It Confidential
    What’s shared in the group stays in the group. This is what makes the depth possible.

This only works if everyone shows up this way.

This Is Not a Fit If

Some of the best founders we talk to aren’t ready for this yet. That’s fine — timing matters more than ambition.

  • You’re still figuring out your first product-market fit
  • You’re primarily looking for tactics, playbooks, or shortcuts
  • You want passive learning instead of active participation
  • You’re not the founder-CEO making the decisions
  • You don’t have time or interest in consistent monthly participation
  • You’re looking for networking more than real conversations

If you’re earlier in your journey, start with the Practical Founders Podcast or the free weekly newsletter.

Hundreds of founders have done exactly that — and joined a peer group when the timing was right.

You Probably Already Know If This Is a Fit

Apply for a CEO Peer Group
Learn more about Peer Groups