Why every CEO should consider joining a top-secret mastermind group

Mastermind groups are quietly gaining steam. Can peer mentoring solve your problems? By Kate Rockwood

XZA HIGGINS was drowning. In five short years, her production company, Parent & Co., had grown from conducting a series of intimate, local gatherings to presenting more than 20 annual events across North America, connecting tens of thousands of parents with brands. Parent & Co. was clocking midsevenfigure revenue and double- digit growth—yet Higgins still had all 16 employees reporting directly to her. “My day would be nonstop questions from direct reports, and I needed to figure out how to keep the company culture positive while getting shit done,” she says. So, last May, Higgins did what many founders quietly do: She took the problem to her mastermind group.

Mastermind groups date back to Napoleon Hill’s 1937 book, Think and Grow Rich, but in recent years the concept has resurfaced. The construct is simple: Two or more entrepreneurs agree to meet roughly once a month to confidentially workshop one another’s business challenges and share notes on a variety of company issues. Rather than a polished networking group in which CEOs put on the brave face of perfection, it’s a safe space for them to bare their vulnerabilities and shortcomings, where they can peek over another founder’s shoulder for guidance on topics mundane (incentive structures) to maddening ( beating out a copycat competitor).

Higgins’s group—eight Chicago-based female founders— had been meeting monthly for about three years, and knew enough about Parent & Co. to help solve her problem. By September, Higgins had a new org structure in place, with zero turnover and no dip in morale. And when she needed to take a six-week medical leave late last fall, “having only three direct reports allowed me to do that— and the company still thrived,” she says.

A half- or full-day commitment once a month is a considerable investment, but founders are finding the mastermind returns to be more than worth it. 1 AVOID YOUR INDUSTRY To jump-start growth at her Ashburn, Virginia–based kids athletic company More Than Cheer, Brittany Rose joined groups, “but there were two competitors in the same group within 10 miles of me.” Rose found herself holding back some of her best tips and biggest questions. Then she sought out a mastermind group with no industry overlap. “Instead of staying in the kids athletic mindset, you’re looking at problems just from a business mindset,” she says. When a martial arts studio owner talked about his successful afterschool program, Rose launched a similar idea at her retail locations. “Three years later, our afterschool program is a substantial portion of our income—and growing,” she says. Company revenue has doubled each of the six years she’s been part of a mastermind group. 2 SEEK A SIMILAR METABOLISM Joining a group that doesn’t share your goals will be frustrating. “We signed up for a group that was all solopreneurs, and it was a terrible fit because they weren’t facing the issues we were,” says co-founder Dustin Brackett of Hive Digital Strategy, in Denver. He’s grown revenue by more than 50 percent the past four years— so he joined a new group focused on growth. Collin Holmes, founder and CEO of San Diego–based Chatmeter, felt a similar frustration in a group of founders who were still in launch mode. While he addressed scaling strategy, most members were mired in basic operations. “The challenges we faced were so different, we weren’t talking the same language,” Holmes says.