Peer group for multimillionaires grows in Sarasota, Tampa

Executive and attorney Wendi Chapman worked for organizations in San Francisco and Washington, D.C., for some 20 years before relocating to Sarasota. Stops were as diverse as vice president of the San Francisco Marathon/Berkley Half-Marathon and the Vietnam Veterans of America Foundation. 

That varied work experience has set up Chapman nicely for her latest role: chair of the Sarasota chapter of Tiger 21. The New York City-based organization is a global peer membership group for ultra-high-net worth entrepreneurs, investors and executives. (One membership requirement is having at least $20 million in investable assets.) Chapman, in her position, is a connector, adviser and organizer for the exclusive and confidential group, which, she says, is like a “personal board of directors” for members. 

Chapman oversees her chapter at a busy time for Tiger 21 in the region. The Sarasota chapter launched in January 2022, and within six months she says the group was at capacity, with a dozen or so members. “There’s so much demand we started a second group,” Chapman says. That chapter is currently seeking new members.

Tampa, meanwhile, has three Tiger 21 chapters, including one that launched last summer. There’s also a Tiger 21 chapter in Naples. In total there are about 60 Tiger 21 members on the west coast of Florida.

The growth and interest in Tiger 21 in the region and across Florida validates a pair of connecting points. One is the post-Covid Florida migration of people from other states, in the North and Midwest, and California, too, is legitimate and includes many people with deep pockets. The second point is even people at the wealthiest levels of life have issues and challenges (along with successes). 

“As more people come to Florida more people are looking for like-minded, wealthy people,” Chapman says. “That’s where Tiger steps in.”

“People make the assumption that when you have all this money everything is just great,” Chapman adds, “but there are challenges in every situation.” 

Chapman and Sherry Horowitz, vice president of public relations for Tiger 21, say little about individual members of Tiger 21 chapters, given privacy is paramount to members. 

One member of the Sarasota chapter, Jay Girotto, was a guest on a recent episode of From the Corner Office, the Business Observer’s weekly podcast on leadership. Girotto, who worked for tech startups in addition to Microsoft and Bain Capital, relocated to the Sarasota area recently from the Pacific Northwest. He now runs Farmland Opportunity, which manages a billion-dollar portfolio of row crop farms in the Midwest and Pacific Northwest. 

Girotto, on the podcast, said he learned about Tiger 21 while jogging on a treadmill and watching a CNBC interview with Tiger 21 founder Michael Sonnenfeldt. He joined the group, he says, mostly because his kids were out of the house and he sought to connect with others for investment opportunities outside agriculture. “The Sarasota group has quite a few people who sold a business and relocated to Sarasota because of all the great things this area has to offer,” Girotto said on the podcast. 

Chapman declined to name any names of the Sarasota chapter, but in a recent interview she gave a peek into the inner workings of the group. She says a progression for some members is to go from groups such as the Young Presidents Organization (YPO) to a business coaching group like Vistage to Tiger 21. That said, Tiger 21 has members in their 30s. 

There are meetings at least once a month in Sarasota, and multiple social gatherings. Members have played pickleball together, golfed together and, says Chapman, done “a lot of boating” together. Members have traveled together to other Tiger 21 meetings, in Baltimore and New York City. There are also learning days for spouses and partners “People get very close here very quickly,” she says. 

But, Chapman stresses, “it’s not just about putting people together. It has to have something where people are comfortable sharing.”

That sharing, she says, includes health and wellness topics, such as brain health, in addition to estate planning, succession and investing opportunities. Members aren’t allowed to solicit other members, and much of the investing conversations, Chapman says, are feedback-based around what should or shouldn’t be in a portfolio.

The Sarasota chapter has men and women members, she says. Industries include manufacturing, technology, health care, fund management and real estate. Members live in Venice, Sarasota, and Lakewood Ranch. “There’s an instant togetherness and instant community,” she says. “These are people with similar challenges who can learn from each other.”