TMBA 279: Can Your Mastermind Offer Insurance Against Failure?

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Today’s episode is all about facilitating high level masterminds, and nobody does it better than Taylor Pearson. It can be hard to figure out what it takes to succeed. Masterminds put you in a position to surround yourself with people who have common goals and will not allow you to fail. This is old school block-and-tackle business strategy. We’re talking about what is important to consider when structuring a mastermind, what we would consider to be an ideal mastermind group, and some of the most useful tools for organizing an effective mastermind group.

Listen to this week’s show and learn:

  • The two major benefits of being a part of a great mastermind.
  • Some success stories from the groups that Taylor has spearheaded.
  • Why you should be working with people who share the same set of business values.
  • The ideal size, frequency and logicstics of a successful mastermind.
  • The three biggest mistakes that mastermind CEOs make.
  • Tips for onboarding new members and getting rid of bad ones.

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST.


Dan & Ian

Published on 01.29.15
  • Casey Ames

    Good episode guys. Some actionable stuff here.

    Pairs pretty well with this one from Start Ups for the Rest of us:

    Always appreciate some more SOP templates from Taylor! Thanks!

  • Dan Andrews

    thanks Casey, appreciate the link to that’s a good one!

  • Maximilian Horsch Breckbill

    Top-Notch episode!

    I’m matching a 2nd round of in-person Sprint Masterminds here in Berlin, and I’ll definitely be incorporating aspects of Taylor’s approach.

    Thanks for sharing your SOPs Taylor! You briefly mentioned the importance of the tone the Mastermind CEO sets when it comes to questions.

    Do you guys have any other favorite mastermind questions, aside from the “what are you thinking but not saying?”

    Again… awesome episode!

  • Dan Andrews

    thanks glad you enjoyed it Maximilian. Here’s some questions from the perspective of the hot seat that you can use (not for the feint of heart!):

    Do you think I’m tracking the right metrics in order to reach my goals?

    Can you see any glaring blind spots that I might not be realizing myself?

    What would you do if you owned this company?

  • Maximilian Horsch Breckbill

    Thanks Dan!

  • Nathaniel Wilson

    Thanks for this, guys, I just started leading a mastermind group of about 4 other people and I want to help everyone get results. I like the suggestion of asking the pointed questions and having a hot seat for one person every session. Hopefully, facilitating masterminds can be one of my income streams in the future.

    Dan, what’s the most important thing you’ve gotten from a group?

  • Dan Andrews

    Hey Nathaniel, glad you enjoyed it… I don’t even know where to start, I have endless examples of honing stratetic ideas (by pitching them in masterminds) or getting fed them outright, for example the idea /concept for the DC was given to me by a more experienced entrepreneur in a mastermind

  • Mitchel M.D.

    Thanks for the SOP google docs. Love to see how others structure business tasks.

  • stefandoering

    Nice. Really experienced advice. Similar to Taylor, the way we select members for our mastermind groups include the 10 C’s:

    1. Chemistry—mutual respect and are energized by each other.
    2. Communication—comfortable and able express themselves freely.
    3. Committed—making the team a priority: punctual and ready “work” together for at least three months.
    4. Comfortable—life is already going well and they are not looking to “fix” things. They are basically happy.
    5. Connected—already tapped into their source energy and the
    spiritual world or express a sincere desire to obtain it.
    6. Contributor—have an innate desire to personally make a real difference for the team.
    7. Coach-able—open to taking the coaching recommendations.
    8. Currency—respectful and honoring each team member’s
    9. Confidentiality—everything discussed is held in strict confidence.
    10. Captivating—ensure the group stays light and fun… lots of laughter.

    Good job guys!

  • Taylor Pearson

    I like these too:

    What’s the best/ideal outcome for you? What does that look like?

    What are the roadblocks between you and getting to that point?

    How high value would it be to you to solve this problem?

    Assume Success/Plan for success – If you were successful, where would you be?

    What am I not doing that I should be doing?

    What am I doing that I shouldn’t be doing?

    What’s the worst case scenario?

    What’s the opportunity cost of X Decision?

    Are you over-complicating this? Is there a simpler decsion?

  • Maximilian Horsch Breckbill

    Thanks Taylor! Great content.

    I’ve already incorporated some aspects of your SOP, and maybe I can add these questions to the resources section.

    Biggest learning from your SOP:
    -1 sentence updates (as opposed to detailed explanations)
    -1 weekly deliverable (as opposed to more than one)

    I’ll be launching 5 groups this Sunday. I’ll let you know how it goes :)


  • Dan Andrews

    awesome! :)

  • Maximilian Horsch Breckbill

    Thanks for this as well Stefan!

    Who are you organizing Masterminds for in NYC?


  • stefandoering

    Hi Maximilian.

    Currently, we run mastermind groups for NYC’s SBS (Small Business Services) as well as for a high-profile company in Brooklyn.

    What types of groups do you run?

  • Maximilian Horsch Breckbill

    Right now I match Masterminds for SMEs and Solopreneurs here in Berlin, Germany. I’d be curious to hear more about how you apply the Mastermind concept to the companies you work with!

  • Maximilian Horsch Breckbill

    Alright! 5x Groups launched, 24 participants total this round.

    IDK what other kind of feedback you’d want, but at the end, at least 3 people mentioned that deciding on ONE deliverable was a big help for them.

    We’ll see how they hold up over the next 2 months :).


  • Vernon Foster II

    Great episode guys. I just had Taylor on my podcast to discuss the sales page that you’ll need to put together when reaching out to potential mastermindees (not sure if that’s a thing). He also shared a real life application on how he’s using this strategy to write his book and recommended “Work The System” by Sam Carpenter for people who aren’t system driven.

  • Dan Andrews

    very cool can you provide the link?

  • Dan Andrews


  • Dan Andrews

    cheers you got it !

  • Vernon Foster II

    Yes sir. Will be sure to post in the comments when it goes live next week.

  • Vernon Foster II

    Dan here’s the link to the podcast Taylor and I did. Finally got it up!
    This will be a nice addition to TMBA 279. In addition to the above mentioned, we also dug into the sales letter. Linked up you guys in the show notes.

  • Dan Andrews

    cool! :)

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