Eye of the tiger: Allen Clary takes reins at exclusive peer-support group

Last week, the Catalyst caught up with Chip Webster, the outgoing local chairman of Tiger 21, an international networking and support group for high-net-worth individuals. 

Webster 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. Now that he’s re-retired, Tiger 21 has tapped Allen Clary to be his successor. 

Clary brings to the role a resume chock full of experience in the startup and entrepreneurial space. He was a senior manager at Tampa-based Tribridge — whose ownership enjoyed a lucrative exit in 2017 — from 2005 to 2008. He then founded Jibidee, an app for personal organization, before joining Cognis Group, an intellectual property consulting and content company, as interim CEO. He’s a co-founder of Tampa Bay Wave and somehow also finds time to teach courses in entrepreneurship at both the University of South Florida and University of Tampa. 

“I’ve been heading up investor relations at Tampa Bay Wave for the last several years, and informally beyond that, I’ve just built up so many friendships and relationships in the high-net-worth community by way of early-stage tech investing,” Clary said. “So [Tiger 21] made a lot of sense from that perspective — I thought would be a good fit.” 

To call Tiger 21 an exclusive club would be a massive understatement. To be considered for membership, applicants must have a minimum net worth of $10 million, but “most are well above that,” Clary said. There are other, less easily defined criteria for membership, but the organization, according to its website, looks for qualities that include “readiness to share, willingness to learn, commitment to not solicit and commitment to attend monthly meetings.” 

Tiger 21 has just 850 members worldwide. Each local group’s membership is capped at 15, but it’s possible for cities to have more than one Tiger 21 group. Atlanta, Clary said, has three groups. Tampa has just one, for now, but it’s growing. 

“We still have a few seats open,” Clary said. “There’s no doubt in my mind that those will fill in by the end of the year, for sure.” 

Group size is limited because Tiger 21 wants to promote tight-knit connections that foster learning, sharing and empathy among the membership. Although Tiger 21 members are wildly successful, at least on paper, they face unique challenges that very few people can relate to, Clary said. Wealth, he added, can both enhance and distort a person’s life and relationships. 

“It can do a lot of things,” he said, “But if you don’t have your legs and you don’t have good peer support, you can really get upside-down in certain situations.” 

Clary isn’t going in blind. Webster, with whom he’s been friends for many years, invited him to speak at a Tiger 21 meeting last year, before the leadership change. He’s since hosted two meetings on his own — one in November, and one this month. The meetings can last up to half a day, Clary said. Because of the pandemic, the Tampa Tiger 21 group has shifted to a hybrid model in which members can participate via Zoom or, depending on their comfort level, in person. 

Tiger 21 also hosts virtual conferences for all members to attend. In October, the @Home Summit, as the virtual conference series is called, featured appearances by high-profile personalities such as Magic Johnson and former South Carolina Gov. Nikki Haley. But like local group meetings, Tiger 21’s large-scale events are about personal growth and education, not business opportunities.

“We’re not an investment club,” Clary said. “We don’t give advice.”

However, Tiger 21 members gain access to an online portal that allows them to connect them with other members around the world who share similar interests, whether it’s golf, hunting, fishing or investing.

“We do have this one area of the portal,” Clary said, “one spot where you can go and opt in to talk about specific deals. But for the most part, that’s not the nature of what Tiger 21 is.” 

As Tampa Bay has matured as a place to start, grow and sell a highly successful business, Clary said he’s seeing more members and applicants who are at a crossroads in their lives and careers. Most have sold a business, are considering a sale or have stepped back from day-to-day operations, and they’re looking for guidance as to what should come next. Most members are between the ages of 45 and 60, with some exceptions. 

“I have a member right now in my group who’s just turned 40, which is amazing,” Clary said.