Starting a mastermind group – lessons and pitfalls

Hey guys and gals,

I’m thinking about starting a local bootstrapper mastermind group here in Finland and it would be awesome to hear people’s experiences from similar groups.

  • How have you organized yours? Just online, just offline or a combination of both?
  • What software has worked best (irc, Campfire, Google Hangouts, …) and why?
  • For the online version, fixed office hours vs. people just come and go, or a combo?
  • Should the number of members be limited? To what kind of ballpark?
  • Any tips on what has worked wonders?
  • On the flipside, any pitfalls you’ve run into with yours that should be avoided?
  • Anything else I’ve missed?

Thanks in advance,


I have not run a Mastermind group, but I held an “startup” meetup while back for around two years.

The things I’ve noticed:

  • I didn’t know/reach enough people who were working on their ideas
  • Thus the percentage of real entrepreneurs was under 50%
  • ~75% people weren’t thinking about starting something in next two months
  • Entrepreneurs who did stuff saw this and were complaining about it
  • People turned out to be surprisingly passive on the event (20 people or less)
  • Afterparty was where the interesting stuff happened (networking, sharing problems…)
  • We had talks so that people would come. Getting interesting talks was somewhat hard.
  • The maintenance and low “results” made me stop doing those.

If I was to do a mastermind group I would try to find people who are experienced and will reply to posts in a forum or mail list.

I’d also try to get angels or people with resources like office spaces, or cowork centers involved. It would be better to know them personally for a long time since you don’t want them to screw your community.

If possible, I’d try to facilitate regular lunches together among people in the group. Its easier for people to be more open, or reply more frequently online, when they have seen each other offline.


@michal_hantl Thanks for the insight! I agree about the formal/informal part. For me the most important part of conferences these days is the hallway track, i.e. having deep and interesting conversations with peers and more experienced people. So the idea here would at least in the beginning only be the hallway track, and let it grow organically to the direction that seems most appropriate for the community.

Startups for the rest us just did a podcast covering How to run a Mastermind. They pretty much cover every one of your questions. Have a regular schedule, keep the numbers low, try to join up with others ahead of you on the path, etc.

I’m also looking to start a Mastermind group within the next few months. I think they are a great way for solo founders to get another perspective on their business.

I do Masterminds face to face, never tried the online kind. I recommend first meeting for lunch/coffee ‘to chat about startups and ideas and stuff’. If it goes well then suggest a regular Mastermind.

I found Mastermind No. 1 in a entrepreneur’s group. Neither of us had went to (or have went to since) the actual events this group had, we just were able to find like minded people in our area, already profiled and contactable on

I met Mastermind No.2 at Startup Weekend, he was there looking for talent for his company,