Madonna and U2 manager Oseary launches FlyWith jet-sharing club

Guy Oseary, the Hollywood talent manager and early investor in Uber and Airbnb, has founded FlyWith, an invitation-only jet-sharing membership that has partnered with Executive Jet Management, Berkshire Hathaway's charter and aircraft management unit, to provide by-the-seat charter flights. According to Private Jet Card Comparisons, the official launch was 29 September, though chief executive Brian Corbett says the club is already operational and has successfully matched members for flights.

Private Jet Card Comparisons reports that membership starts in the low five figures. Members can book flights and share seats with other members, and can also propose routings. Flight hosts can set policies on children and pets. Unlike social media groups offering shared charter, members cannot use existing jet cards, fractional shares, or pre-booked charter flights in violation of the programme rules.

Jet owners can sell seats only if their aircraft is Part 135 certified and managed by Executive Jet Management.

Leadership and staffing

Corbett, formerly a senior executive at Exclusive Resorts and Atlantic Aviation, was recruited nearly a year ago to lead the launch. Amanda Harrison, a longtime NetJets executive who most recently worked for Four Seasons Yachts, has also joined the team. The club currently has 18 full-time employees.

Corbett says the concept is Oseary's brainchild.

Membership networks and partnerships

FlyWith will establish groups around sports teams, events, and cultural institutions such as Art Basel. Partnerships to drive membership include Discovery Land, Zero Bond, Crane Club, and The Bird Streets Club.

Market implications

For existing jet card holders and fractional owners, FlyWith membership operates under strict separation rules: members cannot combine FlyWith bookings with their existing aviation contracts. This constraint means the membership functions independently of other private aviation arrangements rather than as a supplement to them. Prospective members should clarify this requirement before joining, as it affects whether FlyWith complements or replaces their current arrangements.

The membership pricing structure—starting in the low five figures—positions FlyWith as an invitation-only offering in a crowded market of jet-sharing platforms. The reporting does not specify whether membership costs remain stable or are subject to adjustment, nor does it say whether existing members face price increases in future years.