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Peer-support group for wealthy individuals resurrects local chapter

Brian Hartz



Chip Webster, outgoing chairman of Tiger 21 Tampa Bay

The Tampa Bay chapter of Tiger 21, a networking and support group for high-net-worth individuals, has named a new chairman. 

The St. Pete Catalyst will bring you a conversation with the group’s new head very soon, but first, we caught up with outgoing chairman Chip Webster, who ran Vistage Florida, a business advisory and executive coaching organization, for nearly three decades before coming out of retirement in 2018 to lead Tiger 21. 

Webster said he’s been criss-crossing the country in his RV as a way to deal with the isolation of the coronavirus pandemic. “We went all the way to Washington State and back in one week,” he said, adding that he’s visited 22 states since re-retiring last year. When we spoke with Webster, he was back in the Tampa Bay area, camped at an RV dealership in Seffner. 

Webster said a group like Tiger 21, which caters to people who are worth at least $10 million, are important because highly successful people often have few peers who are concerned only with helping them instead of trying to get something from them. For example, the group tackles topics such as philanthropy and how to sustain, preserve and pass on wealth.

“The reason people join,” Webster said, “is because when you arrive at that place of ultra-high net worth, the list of people you can talk to who don’t have an agenda for you just gets narrower and narrower. Everybody wants a little bit.” 

Webster recalled speaking with members who had to fend off requests from “aunts, uncles, cousins” who demanded that the wealthy person buy them houses. “That’s just typical,” he said, “when you reach that pinnacle.” 

Tiger 21, he said, “is a solicitation-free space where you can talk about issues that you’re dealing with, opportunities you’re dealing with … it’s where you can get unbiased feedback and perspective. The collective wisdom of the group is amazing.” 

Webster also said there’s a misconception that wealthy people, particularly those whose fortunes were made through entrepreneurial hard work, have easy, worry-free lives. “That’s the big lie,” he said. “It’s lonely at the top — and lonely at the top of your balance sheet. You could even say that the more money you have, the bigger the problems you have.” 

Tiger 21 operates chapters in several U.S. states, plus Canada and Europe, and is planning to expand in Asia and Australia. In Florida, it’s capitalizing on an influx of entrepreneurs, existing businesses and investment dollars to the Sunshine State in recent years. Not only is Tiger 21 breathing new life into the Tampa Bay chapter, it’s in the process of launching a new chapter in Jacksonville and already has chapters in Miami, Naples, Orlando and Palm Beach. 

Most chapters, Webster said, have a very limited number of members, usually around 15. In addition to meeting the net-worth requirements, applicants must pass an in-depth background check and go through a wealth-verification process. “It’s very exclusive,” Webster said, “and a very serious organization in terms of who gets selected to join.” 

Conversations at Tiger 21 meetings also deal with personal concerns. “Legacy is part of the discussions,” Webster said. “How do you, you know, pass on your wealth without messing up your kids?” 

Keep an eye on the Catalyst in the coming days for an interview with the incoming chairman of Tiger 21 Tampa Bay. 

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    Jack Barrett

    January 21, 2021at8:17 pm

    Appreciate your interview with Chip Webster and his reigniting Tiger 21. His points are well taken. We’ve known Chip for a lot of years, have a lot of respect for his work, and glad he’s back making a difference in the lives of folks who have made a difference in ours.

    Jack Barrett

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