Angel investors fuel Southwest Florida startups

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. 

TAF’s process is often likened to the television show “Shark Tank.” Members pool their money and business expertise to back young companies in a competitive process. As sharks, they’re in it for the money. But as angels, they may be heaven-sent for promising entrepreneurs who win their approval. Cartwright said profit is the members’ primary goal, but “psychic” income — the satisfaction of helping entrepreneurs or boosting the region’s economy — is also a powerful motivating factor.

For companies that successfully pitch TAF, the group’s intellectual capital and substantial contact list may be an even greater benefit than its members’ financial investments. The 48 businesses that TAF has supported so far went on to raise more than half a billion from TAF’s co-investment partners, Cartwright said.

TAF’s 167 members also include many current and retired business leaders and C-suite executives. Startups benefit from their wide-ranging business expertise that spans skills, including supply chain management and human resources in industries such as health care, manufacturing and food service. 

“For us, we’re not after dumb money,” says Dries De Coster, CEO of London-based Meet Dwight. “We want investors like these guys.” 

De Coster pitched his company’s digital worker bot, Dwight, to TAF members at the group’s monthly member meeting in October at Gulfshore Playhouse in Naples. Dwight is an artificial intelligence recruitment assistant designed to help with mundane tasks, such as onboarding employees. 

Another tech company, Naples-based 911locate.ai, pitched TAF members on its service that maps out buildings so emergency responders can more easily locate 911 callers. A third pitch came from Cleveland-based Thrivable, which helps health care companies market products.  

TAF’s latest, 100th investment of $719,982 went to Gainesville-based VOS Systems and its wearable panic device. It came from the fifth fund in the TAF family, which closed at $11.1 million with 76 members. 

The presenters leave the room while fund members discuss whether to move forward with a due diligence process and possibly make an investment. In 15 years, TAF members have evaluated more than 4,691 applications and listened to 413 pitches before narrowing it down to the 48 companies that have received their support so far. 

“A lot of people can write a check,” says TAF member John Kraft. “The Tamiami Funds bring more than just money. We’re attractive because of our members.  

“Naples is where a lot of successful executives retire or have a part-time house. That resource, that’s our special sauce. It’s the introductions that we can make. It’s the experiences in business. It’s really the diversity that we bring.” 

Kraft was a Wall Street equity analyst based in the Pacific Northwest before moving to Naples, where he is senior vice president of finance and strategy for ACI Worldwide, a payments software company. That made him a natural fit for TAF’s due diligence team when it examined ConnexPay. 

“I think my Wall Street experience was helpful to get them the attention of investment bankers in the space and certainly was helpful in getting to the next level of their life cycle,” Kraft says.  

TAF grew out of the 2001 Gulf Coast Venture Forum. During the Great Recession from 2007 to 2009, business leaders aimed to create a regional angel-investment fund to diversify an economy that relies heavily on construction, tourism and agriculture. 

Cartwright has long hoped that TAF will be an essential link in a local startup industry ecosystem and a catalyst for the growth of health care, technology or other potential knowledge-based industries. 

“We keep innovation, ingenuity and creativity here in Southwest Florida because startup companies concentrate around sources of capital,” Cartwright says. “We’re hopeful that we could not only fund local startups but attract startups to Southwest Florida, where they would locate close to their investors, and benefit not only from the growth capital but the intellectual capital we could invest in those companies.”