How Lonely It Is To Be A Practical Founder And My Upcoming Ceo Peer Groups

Multiple practical founders this week have shared something with me that they don’t talk about a lot.

It’s lonely being a software startup founder.

  • Your family and neighbors don’t have a clue what you really do.
  • You can’t talk about your really hard issues or deeper questions with your employees.
  • Since you aren’t trying to raise big outside funding, you don’t spend time with potential investors to get feedback on your vision or tactical questions. And you’re not selling chunks of your company to buy their attention and advice.
  • You stopped going to local startup events with other founders and mentors because it was only about “How much are you raising?” and how to play the funding game.
  • You’re up to your eyeballs actually building product, selling and serving customers, managing and hiring people, and getting sh$t done, so you don’t get out much.
  • Other CEO groups are nice but they don’t get the SaaS game at all. You’re the only one in the room who knows what LTV and CAC mean. Or what your exit math should be.
  • You were better about connecting with founders and mentors before COVID locked us down. Haven’t gotten out much since things opened up.

Growing a company is always really hard.

And it’s harder to do without the support of trusted advisors who have played your specific game before.

It’s harder without being part of a trusted group of peers that are going through the same crazy hard stuff you are experiencing.

Founders with big funding can buy advice and support. And they are part of a club that hangs out together to support each other.

There isn’t as much support for practical founders out there who aren’t spending their equity to buy serious help.

And there isn’t a useful club of practical founders who really get to know each other and support each other through their journeys.

I have heard these requests over and over from practical founders I have talked to in the last year.

I have run all kinds of connection events, mentor sessions, and several SaaS CEO peer groups before. All very useful and helpful for founders and I love doing it.


I’m going to start several CEO peer groups and some expert connection events just for practical founders.

If you’re one of these founders, anywhere in the world, who would like to regularly connect with other practical founders like you…

I’d love to talk to you about what would be most useful to you. And get your feedback on what other founders are telling me too.

Please DM me and let’s have a quick call to help me understand where I should start.

What’s your experience connecting with peer practical founders and savvy mentors/experts?

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