Chicago: January recap & February Signups

Coffee with heartHappy February!

Our next breakfast is two weeks from today, Wednesday, February 27. I’d love to see both newcomers & bootstrappers veterans at the breakfast.

You can sign up here:

In January, we had a lively meetup with about 20 people. As always, topics ranged the gamut and we had lively discussions.

At the table I was at, people talked about:

  • How (and whether) scale a company to multiple states–or stay local and focus on tightening the core business for a while;
  • How to find the right approach to marketing a valuable financial advice service. This was a great discussion because people at the table were able to react to the value of the idea and help brainstorm ways to get it out there. To paraphrase one of the people at my table, “I know /tons/ of people who would love that service: you just need to figure out how to present it”. Which led to discussion of pros and cons of various business models.
  • What happens to an early-stage business when team roles and responsibilities aren’t as clear as they could be;
  • How (and whether) to narrow your target audience to hit a more specific niche;
  • Ways of engaging neighbors & local communities to get value from your hyper-local business.

And more.

I’m always incredibly gratified and impressed by the people I meet and the way everyone supports each other–and January was no exception. The format (tables with 7 or 8 people and one moderator) makes for rich discussions. So whether you’ve been bootstrapping for a while or are just getting started, come out and join us in February!

You can sign up here:



P.S. The discussions start at 7:30 AM, so be sure to be settled so you can take part in introductions.

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