Charlotte’s StreetFair expands to multiple cities

The following article appeared in the April 23, 2025, edition of The Charlotte Ledger, an e-newsletter with smart and original local news for Charlotte. We offer free and paid subscription plans. More info here.

Teddy Fitzgibbons, co-founder of StreetFair, gives a presentation to the “Shark Tank”-like Pitch Breakfast Charlotte in February. The company, which started in 2021, is expanding into new markets.

by Tony Mecia

Entrepreneurs often speak of “light bulb moments,” when a realization suddenly flashes in their brains that there might be a better way.

For Teddy Fitzgibbons, that moment came in 2021, in the form of a steady stream of gutter-cleaning trucks on his street in south Charlotte’s Providence Park neighborhood.

Over the course of a few days, he witnessed four separate companies show up to clean gutters at his neighbors’ houses. It struck him as wildly inefficient — four companies, all driving to his street in the same week, doing essentially the same work. What if there was a way, he wondered, for neighbors in suburban communities like his to pool their accumulated wisdom on home maintenance and recommend good plumbers, carpet cleaners, pressure washers and so on?

“This was my first time owning a house and having a yard, and I didn’t know anything about how to vet a plumber or who’s a good tree trimmer, but I realized that there was nothing my home needed that one of my neighbors hadn’t solved for,” Fitzgibbons said. “It felt crazy that I had to, like, start over every time, as opposed to being able to take advantage of the knowledge and the Rolodex that my neighbors had already built up.”

He brainstormed ideas with Mike Kerr, his co-worker at parking operations tech company Passport. Kerr had been having similar experiences in Huntersville, where he had gone in with a neighbor on a delivery of mulch. Within a few months, the two quit their jobs and launched StreetFair, a free tech platform that lets homeowners see which home services companies their neighbors are using and recommending, and to hire them, with group discounts if neighbors use the same company.

From its office a few streets behind Bank of America Stadium uptown, StreetFair has expanded from its Charlotte roots into two other cities, Dallas and Raleigh. It’s moving into Nashville next month and plans to open in three to five more cities later this year.

Charlotte, a city whose business landscape is dominated by large banks and other Fortune 500 companies, is not known as a hotbed of technological innovation or for having a thriving start-up culture. But local tech boosters say new companies like StreetFair are showing that Charlotte is a place where innovators can build growing businesses. They hope to encourage a more entrepreneurial-friendly climate through regular events, conferences, connections to industry and a new tech hub on North Tryon Street uptown.

“We want people to know there is an ecosystem here,” says Juan Garzón, managing director of Innovate Charlotte, a nonprofit that supports innovation and entrepreneurship in Charlotte. “Companies like StreetFair — that’s what we want to highlight.”

A report released this month on Charlotte’s “start-up ecosystem” found that while the city is an attractive location and that local investment funding is growing, there are still plenty of hurdles to overcome in building a thriving start-up culture, including “lagging” growth in entrepreneurial start-ups, a “fragmented and underdeveloped” support system for entrepreneurs and a “lack of engagement” between the corporate community and entrepreneurial networks.

Despite those challenges, StreetFair is growing after raising $6.8M in investments. Fitzgibbons declined to discuss finances in detail but said that the company is not yet profitable. That’s typical of young tech companies that plow money into growth.

“Our trajectory looks like: Continue to invest aggressively in growth and to make StreetFair a business that has scale, and then, if we’re successful doing that, you should be able to become profitable fairly quickly,” Fitzgibbons said.

StreetFair’s Charlotte operations became profitable in the latter part of 2024, he said, which bodes well for its future as its newer markets become more established.

StreetFair is what is known in tech circles as a “marketplace” business — one that brings together buyers and sellers of a good or service. It’s trying to do for home repairs what Uber does for car rides or Airbnb does for lodging.

Building that kind of business can be tricky, because companies have to sign up both the providers of the service (home maintenance companies) and the consumers of it (homeowners) at just the right pace.

Fitzgibbons says StreetFair has solved that problem in part with incentives that align everybody’s interests:

• StreetFair makes money by taking a percentage of the payments homeowners make to the home services companies in its network, which it screens.

• Homeowners receive recommendations from their neighbors, as well as discounts if multiple owners in a neighborhood use the same provider on the same day.

• Service providers pay StreetFair only after they are paid for a job. StreetFair’s technology collects that information directly from the companies’ customer service management (CSM) platforms, which in the home services industry are tech tools with names such as Jobber, ServiceTitan and JobNimbus.

Many home services companies find it to be a better arrangement than marketing platforms such as Angi (formerly Angie’s List) and Thumbtack. Fitzgibbons describes those as pay-to-play lead generation sites, where contractors pay to have their companies ranked highly in recommendations to consumers.

At a PitchBreakfast Charlotte event in February, where founders describe their companies and face questioning “Shark Tank”-style from an expert panel, Fitzgibbons said it was initially challenging to sign up contractors because Angi and Thumbtack “scorched the earth” by charging companies money for marketing and offering job leads that often didn’t pan out.

“For the first six months, we were calling businesses, and they’d be like, ‘This sounds like Angi. Never effing call me!’” Fitzgibbons said. “And we’re like, ‘I didn’t even have a chance to say that we were totally different from Angi.’”

Angi’s dominance seems to have faded since going public in 2011. Its stock is down 93% since 2021, and its revenue has dropped each of the last two years. Its number of service requests, completed transactions and service providers all fell last year, according to securities filings.

Today, StreetFair has more than 50,000 homeowners signed up, as well as 1,300 service providers across about 60 industries, including car detailing, duct cleaning and pet waste removal. It has 13 full-time employees, said Fitzgibbons, who is 33. His co-founder, Kerr, is 38.

Mike Kerr (left) and Teddy Fitzgibbons founded StreetFair in 2021 to help solve inefficiencies in home maintenance services.

David Sammons, owner of Charlotte Roofing Specialists, says StreetFair has helped his business because his company gets recommended to others after it repairs or installs a roof.

With other services, he was paying increasingly more for marketing with no guarantees of jobs, or he would get leads on jobs that were far away. But StreetFair, he says, leads to new roofing jobs for him and his 20 workers, in areas where the company does most of its work: within a 10-mile radius of Cotswold, where he lives.

He says the company’s platform brings order to what is often a messy mishmash of review sites, paid digital advertising and questionable search engine results.

“In the sea of things on the internet, you try to look up something you just want to know a genuine answer to, and it is a nightmare,” he said. “… If somebody is looking up ‘roofing services in Charlotte,’ what’s the chance they will click on us? What’s the chance they know us from Adam?”

Don Rainey, an early investor in StreetFair, said he was drawn to the company because it “takes the friction out of the lives of consumers and service providers.” Every morning, near his house in Cornelius, “there is an invasion of white vans and landscaping trucks on a massive scale,” he says.

He once counted eight lawn service companies during a two-mile walk in his neighborhood. “One would have been sufficient,” he said.

Startups like StreetFair are important, he said, because when they succeed, they encourage employees to start their own companies. That’s how StreetFair came together: Fitzgibbons and Kerr met while working at Passport.

So many companies have been started by former Passport workers that those entrepreneurs are now jokingly referred to as members of the “Passport mafia.” The Charlotte Business Journal last year tallied 13 companies founded by former Passport employees, including SkillPop, which offers live classes; and DebtBook, which provides accounting software to government agencies and nonprofits.

The term “Passport mafia” is a reference to the so-called “PayPal mafia” that left the payments company to start businesses that included LinkedIn, YouTube, Yelp and SpaceX.

Tony Mecia is executive editor of The Charlotte Ledger. Reach him at tony@cltledger.com.

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