#44: VIP at 35,000 Feet | Flying Private with TrueSkies Aviation
A turkey sandwich on a private jet can run $500 once the delivery fee gets split across a crew of ten. Christian Meiley has seen a single catering bill hit $9,000 for a client who couldn’t decide between sushi and pizza and ordered both.
That’s the kind of detail you only get from the people who actually book the jets, and it’s why Giggs recorded this episode 35,000 feet from Nashville to Ohio, mid-flight, aboard a VIP-configured Boeing 757 with TrueSkies Aviation Group.
Nikki Sanz spent the day with co-founders David Young and Christian Meiley, starting in a hangar at Nashville’s BNA Airport and ending in Columbus, Ohio, where TrueSkies runs its operations. In between: plane trivia at cruising altitude, a rundown of what actually goes wrong when a jet breaks, and two guys who spent decades moving musicians before they ever moved a broker’s license.
From Band Manager to Broker: David Young’s Path Into Aviation
David Young was a working drummer before he was anything else. Out of college in San Diego, he took a job at MCA Records, then left within a few years to develop a band in his hometown himself. That band landed a deal with A&M Records, and its second single, “Counting Blue Cars,” became the most-played rock song of 1996.
A decade of artist management followed, with bands on A&M, Maverick, and Warner. The shift toward aviation started with a scheduling problem: a band booked on two radio shows in one day, in two different cities, with no way to make both by van or commercial flight.
“It’s a people business, you know, it’s a service business. It could seem highfalutin and luxurious, but at the end of the day, it’s just moving people around in luxury, saving people time, and doing it safely.”
Young went on to run entertainment for Sentient Jet, once the largest jet brokerage in the world, then founded and sold Young Jets before helping build the North American arm of a digital brokerage backed by British Petroleum. TrueSkies is what came after all of it, built with a co-founder who came up through a different corner of the same industry.
Christian Meiley: From NASA Launches to Hurricane Rescue Missions
Christian Meiley watched five NASA launches from Cape Canaveral as a kid. He missed the fifth. His family waited 10 days for a weather delay to clear, and it never did before they had to leave.
College pointed him toward marketing, but a post-college stint booking EDM and hip-hop shows in Providence and Boston put him in the position of buying charter flights for touring artists. That’s what got him researching the industry seriously, at a time, he pointed out, before ChatGPT could do the research for him. He founded Meiley Aviation in 2020 and ran it for five years before joining forces with Young.
Some of his most memorable work wasn’t glamorous at all. In 2018, after a hurricane hit Puerto Rico, Meiley worked rescue missions into the Caribbean.
“We were able to send supplies and goods down there with some of the airplanes, because there weren’t any airplanes there to get people out. We’ll bring the resources in on the aircraft, and then we’ll bring the passengers out on that same aircraft.”
What TrueSkies Actually Solves for Touring Teams
About 7 percent of aircraft have a dispatch issue on a given flight, whether that’s weather, mechanical, or something else entirely. For a touring crew of 75 people with a hard show call, that number matters more than almost anything else in the pricing conversation.
TrueSkies built a program called TS Trip Protection specifically for that scenario: if an aircraft breaks, the program guarantees up to 100 percent of the original charter cost toward a replacement plane of equal or better caliber. It sits alongside the TrueSkies Reserve model, which trades a client’s upfront commitment for a fixed, disclosed service fee instead of the opaque markups Young and Meiley say are common across the industry.
The pitch to tour managers specifically is about what a travel day actually costs. Meiley described a client flying commercial from North Carolina to a show at Foxwoods in Connecticut: a 13-hour day, split across multiple connections. On a private aircraft, the same trip took three hours.
“Flying private is a time machine. I mean, having the luxury of pulling up to an aircraft, opening your door, getting your luggage loaded on, taxiing off, is a win all of itself.”
It’s a distinction booking agents don’t always make when they route a tour: a travel day on paper isn’t the same as a day off, especially when it eats 13 hours instead of 3.
The Team Behind the Curtain: Columbus Ops and Goodwin
TrueSkies runs its operations out of Columbus, Ohio, with roughly six people selling and another 15 in the back office. Behind that team sits Goodwin, a technology partner that gathers client quotes, handles payment, and files flights, freeing TrueSkies to focus on the client relationship instead of the paperwork behind it.
Goodwin co-founder Tolga Demarel came out of the insurance industry, where he watched venture money try, and mostly fail, to remove brokers from complex, high-touch transactions. He’s betting private aviation works the same way.
“We’re not trying to get rid of the broker. In fact, we’re betting millions and millions of dollars that the broker’s not going anywhere.”
Between the two of them, Young and Meiley have flown a tuxedo to a state dinner, pulled a pop star out of a country on the edge of a riot, and flown three dogs across the country because their owner was homesick on tour. None of that makes it into the pitch deck, but it's all part of creating excellent client experiences in private aviation.
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