THE ENTREPRENEUR
TYLER HOLT, 34Founder and President
AvSKY, Sarasota County
In 2011, Tyler Holt was a 20-year-old high school graduate looking for a job, any job that would give him a chance. After too many rejections to count, he landed an $8-an-hour position cold calling for a private jet brokerage.
Four years later, he launched his own company in the space: AvSKY. Now, a decade in, Holt leads a 13-person team out of the Sarasota area, has built a profitable multimillion- dollar business and has expanded AvSKY into private jet charters and aviation parts. But his high-flying success story wasn’t without some turbulence.
Holt grew up in Sarasota County’s Englewood, shuttling between households after his parents divorced. After high school, he tried a few gigs, including selling real estate and trading stocks. He briefly attended the State College of Florida Manatee- Sarasota on a scholarship, but the Great Recession made the traditional college path feel out of reach. “I didn’t really have four years to spend there,” Holt says. “I needed to go get a job and figure something out.”
A job hunt led him to JetBlack Aviation, where what started out as cold calling turned into actual aircraft sales. “I loved it. I started building relationships, and then it turned into selling planes.”
By 2015, Holt wanted more autonomy and earning potential, and the chance to build his own team — so he took the leap and founded AvSKY. “I had a little money saved up, a tiny mortgage, and my wife worked. I was in a position to take a risk.”
What followed, however, were about 18 grueling months of doubt, setbacks and financial strain. “I went 10 months without a deal and burned through about $150,000 of my savings,” he says. Then when a big deal nearly collapsed, and even drew threats of a lawsuit, he hit a breaking point. But that difficult transaction did eventually close, and Holt followed it with a few more deals. “We just found our stride and took off."
Building the Business
AvSKY specializes in buying and selling private aircraft for clients. A typical-sized transaction is in the $3 million to $8 million range. The company occasionally buys planes and flips them.
Unlike much of the fragmented aircraft sales industry, where lone brokers often operate independently, Holt set out to build a company centered on collaboration and camaraderie — and one that would inspire employees to stick around. His approach: Pay well, create a fun atmosphere and hire people he knows and trusts.
He hired his longtime friend Ryan Brnovich on a gut feeling that Brnovich would excel; Brnovich is now VP and partner. “People say never hire friends and family, but your best chemistry is with your friends,” says Holt. “We are a connection business, it’s a people business, and we have to have good chemistry.”
AvSKY has grown steadily, generating $5 million to $6 million in annual revenue, and Holt believes doubling or tripling that amount isn’t unreasonable. “We’ve basically grown every year in terms of revenue and size,” Holt says.
A major challenge came along when 2022’s Hurricane Ian destroyed AvSKY’s office, forcing the team to go remote for nearly nine months. That pause made it nearly impossible to train new employees, as much of their onboarding relies on in-person shadowing — but the company persevered.
In 2024, the company did 42 transactions, and Holt says AvSKY is on pace to exceed that this year. He hopes to eventually hit 100 deals a year, which would rank the company among the top aviation sales firms globally, he says.
As AvSKY has grown, Holt has also had to manage the complexity of scaling a tight-knit team. “We’re starting to bump into each other more. Operationally, it becomes a little bit more complicated,” he says. Still, his priority remains growing the company in a way that benefits his people. “I’m loyal to a fault. I want to grow without hurting the people that have been loyal, who have stuck with me.”
Sky High Ambitions
To further serve clients, Holt launched AvSKY Charters in early 2024 with Cameron Cary at the helm. The learning curve was steep. “It took us six months just to figure out the basics, but I know I’ve got the right guy running it.” Cary is now a partner in the company.
One of their earliest charter missions was humanitarian: flying into Haiti during civil unrest to evacuate 30 people in two trips. “We didn’t make any money, but it was a nice thing to do — and it was trial by fire,” Holt says.
After making about 20 trips last year, AvSKY Charters had already matched that number in the first quarter of 2025. The company now aims to 5x its charter volume this year and to that end has inked a key partnership at Venice Municipal Airport.
For Holt, doing business in the Sarasota region has been ideal. “I was lucky enough to be born in the place everyone seems to want to move to,” Holt says. With no state income tax and minimal red tape for his kind of business, he hasn’t faced regulatory hurdles.
Most of AvSKY’s aircraft brokerage clients are spread across the country, but the charter business has a distinct local flavor. And with the Sarasota region being a wealthy market, that bodes especially well for charter growth. In addition to AvSKY and AvSKY Charters, Holt also owns a general aviation parts company in Englewood. Now, his focus is on bringing the businesses to the next level.
Next up is the move to AvSKY’s new, larger office in early 2026 in the downtown of Wellen Park, a master-planned community that’s being developed south of Sarasota and north of Englewood. It will be the company’s first permanent location. “Now that we’re settling in, I think we’re going to hit hypergrowth mode.