Naples angel investors offer startups more than money  

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 homerun now and then, things are going well.  

“The hard part about this business is the money is made on not missing the winner,” said 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.” 

In September, TAF marked its 100th investment in a total of 48 companies since it began 17 years ago. It remains the largest member-managed angel fund in Florida, offering key support for innovative startup companies. Known as angel investors by trade, TAF members pool their own money and business expertise, using it to back young companies in a competitive process often likened to the television show “Shark Tank.”  

As sharks, they’re in it for the money. But as angels, they may be heaven sent for promising entrepreneurs who win their approval. The companies that pitch TAF often want the group’s “intellectual capital” as much as a cash investment.  

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

Coster pitched his company’s digital worker bot, Dwight, to TAF members at the group’s regular meeting Oct. 13 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.  

The presenters left the room while TAF members discussed whether to move forward with a due diligence process and possibly invest in one of the companies. They will vote on those steps at future meetings.  

TAF’s latest, 100th investment of $529,994 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. 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. 

Since TAF began, its total of 167 full- or part-time members include many current and retired business leaders and C-suite executives. Their wide-ranging expertise spans business skills, such as fundraising and human resources and industries such as health care, manufacturing and food service. 

In all, TAF members have evaluated more than 4,691 applications. Of those, they listened to 413 pitches and finally invested a total of $35.6 million in 48 companies. Cartwright said that those companies went on to raise $496 million from TAF co-investment partners. 

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

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

“Naples is where lots 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 they examined Bonita Springs-based ConnexPay. The company disrupted the travel industry’s business-to-business payment system and became one of TAF’s major success stories.  

“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 said.  

Cartwright said members often have two bottom-line goals. The first is profit, while the second is “psychic” income that may include the motivation to help entrepreneurs or be a boon to the regional economy.  

Cartwright has long hoped that TAF will become a catalyst for the growth of health care, technology or other potential knowledge-based industries in Southwest Florida.  

“We keep innovation, ingenuity and creativity here in Southwest Florida because companies concentrate around sources of capital,” Cartwright said. “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 in the growth capital but the intellectual capital we could invest in those companies.”