Since 2010, Tamiami Angel Funds has invested $36.6 million in 48 companies, reaching its 100th deal in 2025. Chair Timothy Cartwright expects 10 to 14 more investments over the next two years. Investors who bet on fledgling companies take a lot of big swings. Even if they get a hit less than half the time, including a home run now and then, things are going well. 

“The hard part about this business is the money is made on not missing the winner,” says Tyler Hardt, a portfolio manager and equity analyst who joined the Naples-based investment group Tamiami Angel Funds. “My biggest worry is, we say no to someone and we’re wrong.”

Since beginning in 2010, TAF has invested more than $36.6 million in 48 emerging companies, marking its members’ 100th investment in September 2025. Each company managed to convince the group of wealthy, experienced investors that its product or service could produce a financial windfall by innovating or disrupting industry standards. 

Angel investors are often associated with backing Silicon Valley tech firms, but TAF remains the largest member-managed angel fund in Florida. Its success stories include Miami-based Kind Designs, which is changing how coastlines are protected with its 3-D printed living seawalls; and Bonita Springs-based ConnexPay, which disrupted the travel industry’s business-to-business payment system. Timothy Cartwright, TAF chair and partner of Fifth Avenue Family Office, expects that fund members will invest in 10 to 14 more companies over the next two years. 

Article featured in Gulfshore Business