- February 26, 2026
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Saying no to customers drove aviation entrepreneur Tyler Holt to start a new business.
For nearly a decade, Holt had been brokering aircraft sales through his Sarasota County-based company, AvSky Jets. He started the business ins his mid 20s in his bedroom and had grown steadily in clients and employees. (Holt, in his LinkedIn profile, says he's an ex-Realtor who sold a house at 18; a college dropout; and his previous "career ambitions that failed" include UFC fighter, bullrider, stock/forex/commodity trader, pro golfer, inventor and physicist.")
“More times than I can count, we've sold an airplane for somebody, and then they call a week later and say, ‘Hey, I don't have an airplane anymore. I need to fly [somewhere]. Can you help me with a charter?’” Holt says. “The answer forever had been ‘No, sorry, I can't help you.’”
As he was looking for a solution, Holt says he also found the right person to lead the new venture: Cameron Cary. The two connected over LinkedIn when Cary, in college studying economics in Tennessee, reached out for some career guidance. Holt convinced him to leave school and join the new business — AvSky Charters — as its CEO.
Cary is “extremely good with people, a really hard worker — all the things you really can't teach,” says Holt, 35.
AvSky Charters got off the ground in 2024 and is now in full growth mode. The company, which has an office at the Venice Municipal Airport and is building a headquarters in nearby Wellen Park, has flown everyone from business owners to stranded missionaries to a country music celebrity.
Now that AvSky Charters has taken off operationally, the plan is to quadruple its year-over-year flight volume in 2026 and reach 10 times its 2025 volume “in the next several years,” Holt says.
Parent company AvSky Corp., which did about $8 million in revenue in 2025, has the “right pieces in place” to grow exponentially, Holt says. “We just have to do it.”
One thing that differentiates AvSky Charters is “heart,” according to Cary. The staff fundamentally cares about the outcome for its clients, he says.
“We try to be as personal and white-glove as we can,” Cary says, “taking care of our passengers as if they were our own family members. You'd want your family member to have everything before they even ask. So that's how we take care of our clients.”
Recently, Cary met a client embarking on a charter at 2 a.m. to ensure he had a smooth departure.
More love for its clients: for Valentine’s Day, AvSky Charters decorated a plane for a couple taking a romantic trip, including flowers, ribbons and champagne engraved with their anniversary date.
“We cater mostly to ultra high-net worth individuals, business owners, family offices,” Cary says. “We handle everything from sourcing the aircraft, arranging the crews and any extra logistics, from ground transportation to catering to anything else that might make that flight and trip more enjoyable.”
AvSky Charters is the customer-facing side of the business and partners with operators that handle planes and pilots.
One challenge the business faces is finding clients who can afford its services. A “local hop” from Venice to Miami could cost $5,000 to $10,000, while longer flights can cost upwards of $15,000, according to Cary and Holt, who note pricing varies.
“Give us a trip, and we can give you a price,” Cary says.
Anyone can submit their trips for quotes on the AvSky Charters website, and web traffic has proven a lucrative lead source for the company.
One client shared he got quoted for a trip from Miami to Grand Cayman at 2 p.m. and was wheels up at 4:15 p.m. that day.
“It's hard to get the first shot, but once we do, we hit it out of the park and they’re a client for life,” Holt says.
Another way the company gets clients is through cold calls. That’s how it landed a trip with country star Luke Combs.
“I called his team,” Cary says. After building a relationship with the person who handled Combs’ travel, being as transparent and competitive as possible, the company won the contract. AvSky Charters coordinated the travel for Combs and his crew between shows in Ocean City, Maryland, and Austin, Texas. About 50 people were part of the posse, requiring a larger aircraft than a traditional charter. Afterward, the group invited Cary to the show and took him backstage.
Another one of AvSky Charters’ most notable flights was among its first: a humanitarian trip to Haiti in 2024. A man reached out to AvSky Charters saying his family members were in the country amid civil unrest with church group volunteers. “And nobody was going to get them,” Cary says.
While the man said he would pay for the flight, he told Cary every charter company he tried had already turned him down.
“I said, ‘Let me see what I can do,’” Cary recalls. After talking to many people in the industry to ensure they had a “legal and safe way” of getting to Haiti, AvSky Charters coordinated two flights that rescued more than 30 people. “I don't think I've had a trip that difficult since.”
But Cary says challenges are the norm, as uncontrollable factors like weather and equipment are always in play in the charter business. AvSky Charters differentiates itself through caring and communication, he says.
For example, he had a client booked for travel out of Massachusetts during a predicted winter storm. He presented her with options a week ahead of time. Ultimately, she ended up leaving a day earlier than planned to ensure she could make her trip.
“If I were to take all of my clients and have you talk to them, the ones that would probably say the best things are the ones where the trip didn't go 100% according to plan,” Cary says. “Those are the ones where … you find out whether your company is good or not, and if your individual broker is good or not. And people find out all the time, unfortunately. But that's where we separate ourselves. It's the combination of transparency and then genuinely caring.”
While AvSky Charters can accommodate global travelers and has access to a network of more than 12,000 aircraft worldwide, there is what Holt calls a “local component” to the business.
The company has an office at Venice airport, which provides visibility and access to new clients. In addition, officials hope the company's new 2,500-square-foot office under construction in Wellen Park, near Venice and North Port, will scoop up travelers headed to the Atlanta Braves’ nearby spring training facility, CoolToday Park.
At the new Wellen Park headquarters, AvSky Corp. — which also includes sister companies AvSky Jets and aviation parts business Rocky Mountain Air Parts — will house its 15-person staff. About five employees work for AvSky Charters, but Holt says there is crossover among the AvSky Corp, subsidiaries. He hopes to see more commingling among clients.
“I think we'll see this as we grow — crossover between people who charter and then ultimately buy, and then [conversely], people who sell and then go back and charter,” Holt says.
Moving into its Wellen Park headquarters will mark a major milestone for AvSky Corp., which originally started out of Holt’s bedroom in 2015. The company has also had offices in Venice and Englewood and was remote for a time after the 2024 hurricanes.
“We’ve been all over the place,” Holt says. “It will be nice to get there and settle in.”
Holt also hopes to grow the AvSky Charters sales team and web presence to increase exposure.
“We're right on the takeoff,” as a company, Holt says. “I'd say we're off the ground, and we're ascending.”
