Masterminding the Path to Success

Light bulb and group of business people brainstorming at an office.

Ask Kirk Drake, an Oregon based serial entrepreneur, what has fueled his successes and Drake comes back with one word that you probably hadn’t expected: masterminds.

Just what is a mastermind? It’s an idea that traces back at least 100 years but it just may be most needed right now, in a tumultuous economy that is filled with unexpected hazards — but equally unexpected opportunities.

The idea is simple: a small group of people agree to join together on a regular basis — often monthly but it could be weekly or even quarterly — to openly and candidly hash out ideas, challenges and possible solutions, and pathways to heightened success. That is what is called a Mastermind group.

Drake says he first joined a mastermind group around 15 years ago, not long after he founded Ongoing Operations, a Maryland-based credit union service organization that offers disaster recovery, cybersecurity, and cloud hosting to credit unions. Drake, who came to start Ongoing Operations from an executive job in a credit union, realized there were things he didn’t know about managing people, dealing with investor-owners, and sales. When he heard about a mastermind group, he was immediately all in. “I fell in love with it,” he says.

Masterminds also have changed his life. In the last half-dozen years — due to ideas and discussions that arose in mastermind groups — he has started a second company, CU2.0, that offers consulting services to credit unions and financial technology companies that want to sell to credit unions. He also wrote a book, CU2.0: A Guide for Credit Unions Competing in the Digital Age, and he moved coast to coast, from Maryland to Oregon, where he and his wife started a winery, Resistance Wine Company.

“All those decisions — writing the book, founding CU2.0, and the winery — grew out of ideas and discussions in mastermind groups,” says Drake.

Oh, and he has remained CEO of Ongoing Operations even though the headquarters and most employees have remained in Maryland. But in exploring the idea in mastermind groups, Drake came to believe he could do much of the leadership and management remotely, and four years later, Ongoing Operations continues to thrive.

Hill on Masterminds

Just what are these mastermind groups? Dial back to motivational writer Napoleon Hill for the scoop.

Hill spelled out the magic of a mastermind group in his book, Think and Grow Rich: “Analyze the record of any man who has accumulated a great fortune, and many of those who have accumulated modest fortunes, and you will find that they have either consciously, or unconsciously employed the ‘Master Mind’ principle.”

Wrote Hill: “It is a well known fact that a group of electric batteries will provide more energy than a single battery.”

He elaborated: “Through this metaphor it becomes immediately obvious that the Master Mind principle holds the secret of the POWER wielded by men who surround themselves with other men of brains.”

A proof of the power of a mastermind group is Andrew Carnegie, one of the wealthiest people in American history who personally worked with Napoleon Hill. Carnegie is known for crediting his successes to his mastermind group participation.

For a contemporary example, there is the author and motivational speaker Jack Canfield, co-creator of the fantastically successful Chicken Soup series of books, which has sold over 100 million copies. But before it got there, the unpublished manuscript was rejected by 30 publishers. And Canfield himself struggled with financial problems. But he carried on. What has kept him on course? Mastermind groups. Canfield believes so strongly in them that he offers a free guide on his website to starting one’s own along with his personal endorsement of the concept.

What gives a mastermind group such power? The Mastermind group secret sauce is that it collects people into one group who all share a determination to better themselves and to help others do similarly. That energy is transformative for many participants because, ultimately, it’s what they joined a mastermind for.

More Masterminds

Serial entrepreneur Darryl Hicks — now CEO and founder of Montreal startup FlexPay, which uses artificial intelligence to reduce false declines on credit card purchases — says, “I would not be the entrepreneur I am today or the man I am today if I hadn’t been in mastermind groups.”

Today, Hicks is in several, and he says he approaches each session with two questions in mind: Where am I stuck? Where do I need help?

And help he has gotten. FlexPay is his seventh startup.

“It could be how to look at a problem I’m struggling with a little differently or, in many cases, it’s that a group member gives me an introduction to someone I want to meet,” Hicks elaborated.

Find a Mastermind Group

Search online for a mastermind group, and there are literally thousands.

Many are free and are essentially an informal group set up by a half dozen or a dozen (larger groups are often unwieldy) business associates who agree to meet regularly. Some charge fees — anywhere from a few hundred dollars a month to hundreds of thousands of dollars annually. There is a group for any budget.

One rule in many mastermind groups is that there are no competitors; that is, there is only one bank president, one clothing store owner, one fitness coach.

Then there are footnotes. A group could have multiple lawyers, for instance, if they practiced in different areas. A criminal law specialist does not compete with a personal injury lawyer. A public relations expert who represents restaurants does not compete with one who represents hospitals.

The underlying idea is that the presence of competitors will stifle openness and sharing of ideas and fears.

But another new Drake venture is the CU2.0 Mastermind Group, where he blends credit union senior executives and executives in financial technology firms. He does not allow fintech competitors in the same group but has no concern about putting four or six credit union executives in one group; in most cases, credit unions do not compete with each other. They tend to be smaller institutions that serve a narrowly defined audience.

A plus of an organized group is that it can screen potential members for suitability. Drake says he personally talks to candidates to assess their readiness to be open and also to seek to help other members. Not everybody passes inspection.

The Key Metric for Gauging a Mastermind Group

Want to know if you are in the right mastermind group? First off, ask yourself, do the other participants have experience relevant to me, and do I have it for them? A startup entrepreneur probably isn’t in the right group if everybody else is a corporate middle manager or a wannabe social media influencer.

The next — and biggest — measure is from Kirk Drake: “The power of the group is proportional to how open everyone is.”

Understand, getting to openness takes time. Don’t expect it in the first meeting or the fifth. But it should surface long before the 50th meeting.

If a mastermind group isn’t working, leave it. For instance, Drake says he has left a few, including one that had been valuable for some years, but then, suddenly, it ceased to be for him. That’s the signal to leave.

There’s always another you can join.

Moderated or Not

Probably the crucial decision for anyone seeking involvement with a mastermind group is whether to join one that is self-directed by members or a group with a professional moderator. Free groups generally have no moderator, whereas many groups that involve fees do.

What does a moderator bring to this party? Relationship expert Dr. Patty Ann Tublin, who moderates mastermind groups, says that in her role, she “stirs the pot” and keeps the group’s energy level bubbling. She also “creates an environment where there is trust, mutual respect, and rapport so that members are willing to share not just successes but failures.”

That readiness to share failures is key to many mastermind groups. It’s what often helps not just the member who talks of their failure, but all group members grow. Failure frequently is a more fertile learning experience than success.

But it takes a real and shared trust to reveal failures — especially on the part of the entrepreneurial types who often are attracted to mastermind groups. A moderator helps maintain and nurture that trust.

For Darryl Hicks’s part, as a veteran of numerous mastermind groups, some moderated, some not, “the data is in: you need a moderator to keep people on task. Everyone gets more value when you follow a playbook and in a mastermind group, it’s the moderator who brings the playbook.”

Robert McGarvey

Robert McGarvey, a veteran journalist who has long covered startups and small businesses, created and hosts the CU2.0 Podcast for credit union and fintech executives which is at 120 episodes and counting.

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