Music legend Guy Oseary backed Airbnb and Uber. Will FlyWith take off? ByDoug Gollan, Contributor. Doug Gollan covers private aviation and the business of luxury travel. Sep 29, 2026, 11:01am EDT Sep 29, 2026, 02:15pm EDT Summary. Music mogul and tech investor Guy Oseary has launched FlyWith, an invitation-only private jet crowdsourcing membership. Despite past misses by the likes of JetSmarter, Wheels Up, Vista Global's XO, BlackJet, JumpJet, Set Jet and others, Oseary, an early Airbnb/Uber investor, believes his venture will succeed by targeting existing private jet users for longer, larger-cabin flights. FlyWith boasts an experienced executive team, partnerships with luxury communities like Discovery Land for a built-in clientele, and uses NetJets' Executive Jet Management for charters. Members can host, propose, or browse flights, with annual fees in the low five figures. Challenges include coordinating schedules among the ultra-wealthy. However, FlyWith is already active, aiming to capitalize on the 40% of private jet users interested in sharing. Can FlyWith succeed where other private jet charter seat-sharing efforts have failed? Music mogul Guy Oseary, featured on a 2016 Forbes cover highlighting top tech investors, apparently thinks so. Oseary's managerial career in Hollywood includes Madonna, U2, and baseball superstar Alex Rodriguez. His success in aligning with winners has extended to early investments in both Airbnb and Uber. Now he is the founder and force behind the new charter crowdsourcing, invitation-only membership that launched today. It should work. In fact, nearly 40% of private jet users say they are interested in sharing. Yet deep-pocketed players such as Wheels Up (now focused on its alliance with Delta Air Lines targeting corporate jet charters), JetSmarter (a one-time unicorn) and Vista Global, which bought JetSmarter and tried to continue the crowdsourcing model via its XO platform, have all retreated from the space. Others like BlackJet, JumpJet ("The Netflix of private jet travel") and SetJet have gone to aviation's extensive graveyard. A handful, such as private equity-backed FlyHouse, Surf Air (targeting the future of urban mobility), and several enthusiastic boutique brokers and clubs, are still trying to solve crowdsourcing for private flyers. Informal groups use social media to sell seats and split costs on the New York-Miami-Aspen triangle. Many of the offers in those private chats likely violate federal regulations governing how and when sharing can occur. In giving it a go, Oseary has assembled executive talent with success in sharing-economy ventures, private aviation, and attracting UHNW clientele. CEO Brian Corbett was a founder of home-sharing membership club Inspirato, and a C-level executive at Atlantic Aviation, one of private aviation's biggest operators of FBOs, the terminals that private jets use. Head of Marketing Amanda Harrison brings over a decade at NetJets, the world's largest private jet operator and the originator of fractional jet ownership. The project has been in development for almost a year. FlyWith will use blue chip Executive Jet Management, a unit of Berkshire Hathaway-owned NetJets, Inc., as the primary provider of charter flights. Discovery Land, whose high-end residential communities include Yellowstone Club in Montana, Baker's Bay in the Bahamas, and other pricey venues from Scotland to Hawaii, offers a built-in pipeline of members who, if they don't personally know each other, share a common lifestyle and, most importantly, similar travel patterns. Partners such as Zero Bond, Crane Club, and The Bird Streets Club provide a source of flyers who may want to flock together. MORE FOR YOU Corbett says, "Starting backward from where the need comes from, we, through personal experience and professional experience, have seen, experienced, and heard stories for years about people showing up at the same events, whether it be business meetings or weddings or whatever, and realizing that they flew on separate planes. It would have been much better if they could have flown together, or they even run into people, their friends at the FBO, and say, 'Oh, my gosh. We're both going to the same place. How silly.'" Annual membership fees start in the low five figures and there is a family option, although Corbett declined to provide specifics. It's invitation-only, and if you are invited and accepted, there are three ways to share. As a host, you charter a private jet and decide how many seats to sell, your pet and kid policies, and who to share it with - the entire community or specific connections and groups. You can propose flights and see who else is interested before committing. You can also browse listings on the app showing the routings, number of seats, and cost per seat. There is a function to be anonymous. The app automatically prices out seats based on the total cost of the flight. Payments are managed online. The annual fee is a relative pittance for the target audience and if it only works infrequently users will still cover their membership. Passport: Explore the finest destinations and experiences around the world in the Forbes Passport newsletter. Corbett argues that others who failed were doing jet-sharing as a side business, targeting aspirational flyers without much vetting, or focusing on shorter flights on smaller jets and turboprops. FlyWith, he says, is targeting users who are already flying privately, taking longer flights, and are seeking a larger cabin experience, have deeper pockets, bigger upsides for savings, and are not necessarily intent on filling every seat. "A lot of (concepts) are on small jets or turboprops that are not actually really great for sharing," Corbett says. "You end up locking knees." By contrast, one or two people on a two- or three-zone 14-seat Gulfstream or Global jet can feel lonely. He says in those cases, private flyers will sometimes trade their jets for a first class seat on the airlines. That gap could be a bit of white space. It may also be an obstacle. Jet owners can only share seats if their airplane is on Executive Jet Management's charter certificate. Fractional owners and jet card members who have hours they already paid for and in some cases must be flown on an annual basis, can't use the FlyWith platform to sell empty seats either because programs don't permit it or it would constitute illegal charter, sometimes both. In other words, members who match up on where they are going, how many seats they need, and when they want to go would forgo their own programmatic solutions or jets for the trip. A former industry executive says there are niches where it could work, such as college football weekends - something that is part of the FlyWith plan. Tentpole events like Art Basel Miami or the Masters would be other examples. What rich people who fly their private jets with empty seats say they want, and what they are willing to do to fill those seats, are two different things, says another person who has been there and tried it. "It all sounds good until you want to leave at 3 pm and I can't leave before 5:30, or you want to go out of Opa Locka, and I want to go out of FXE (short for Fort Lauderdale Executive)," two South Florida airports less than 30 miles apart. "It's often that close, but a dealbreaker." Corbett says the club is already up and running in terms of having active members and has successfully matched flyers. FlyWith seems far from a basement start-up with a PR company and a dream, something in private aviation that is more frequent than you would imagine. It has 18 full-time employees, though it describes itself as asset-light, meaning it doesn't own airplanes like Aero, JSX (the most successful to date) and Slate. They operate adjacently as public charters and fly on a set schedule similar to the airlines but use private terminals. "It's a long putt," says one industry insider with intimate experience in the concept, comparing getting rich jet users to coordinate flight schedules to herding cats. Still, he says, "Sometimes long putts go in." Back in 2016, Oseary told Forbes the key to his success was keeping an open mind. In private aviation, it often takes an open wallet, too. In 2010 Warren Buffett revealed it took a decade of ownership for NetJets to become profitable. He also credited Berkshire Hathaway's deep pockets, and several years ago, the late Charlie Munger said the fractional ownership company is now worth as much as a major airline. NOW PLAYING: Fueling The Innovation Pipeline: A Cash Back Content Series FORBES' FEATURED Video Less than $2/week.

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