The Social Skies: Inside FlyWith, the App Bringing the Sharing Economy to Private Aviation

Main Facts

The private aviation sector has long defined the pinnacle of personal mobility, offering uncompromised luxury, speed, and discretion. Yet, beneath the veneer of exclusive terminals and pristine leather cabins lies an inherent inefficiency: thousands of private aircraft take off every day with empty seats.

Enter FlyWith, an invitation-only membership platform designed to bridge the gap between private jet travelers and the untapped capacity sitting right beside them. Co-founded by Sound Ventures managing partner Guy Oseary and led by luxury hospitality and aviation veteran Brian Corbett, FlyWith is a pioneering digital ecosystem that allows private flyers to coordinate schedules, share flights, and split charter costs with friends, mutual acquaintances, or pre-vetted members of an elite community.

Following months of private trials, FlyWith is officially launching in North America this October. Utilizing an intuitive, app-based interface reminiscent of high-end hospitality platforms like Airbnb, the service allows users to charter spacious super-midsize and large-cabin jets—primarily through a strategic partnership with Executive Jet Management, a subsidiary of NetJets—and effortlessly distribute seat allocations among their social or professional circles.

Rather than upending traditional jet ownership, jet cards, or fractional models, FlyWith introduces a complementary layer to private travel. It turns serendipitous terminal encounters into intentional, cost-shared, and socially engaging journeys.

Chronology: From Concept to Runway

The genesis of FlyWith bridges the gap between venture capital innovation and high-end lifestyle logistics.

• The Conceptual Spark: The idea was originally conceived by Guy Oseary, who recognized a glaring disconnect in how ultra-high-net-worth individuals travel. While social media immediately updates people on where their peers are after they arrive, there was no digital infrastructure to reveal where friends were heading before departure.
• Assembling Leadership: Oseary tapped Brian Corbett to serve as Chief Executive Officer. Corbett brought extensive industry experience, having cut his teeth in luxury hospitality with brands like Inspirato and Exclusive Resorts before serving as the leader of aviation infrastructure firm Ross Aviation. Upon hearing the pitch, Corbett’s initial reaction was disbelief that such a platform did not already exist.
• Strategic Partnerships and Vetting: To build a secure and trusted user base, FlyWith established partnerships with elite private social clubs and lifestyle brands, including Discovery Land Company, Zero Bond, and the Crane Club. These institutions provided the foundational network of pre-vetted clientele.
• Trial Phase (August – September): FlyWith initiated closed-group trials with select members, culminating in successful test flights. According to leadership, these early operations proved the software’s seamless integration with partner operators down to hyper-specific cabin requests, such as eliminating single-use plastics in favor of glass bottles.
• Official Launch (October): The platform is slated for its official North American debut, with invite-only membership tiers opening up to a broader pool of qualified applicants. International expansion remains firmly on the roadmap following the domestic rollout.

Supporting Data & Operational Mechanics

FlyWith’s market viability is underpinned by internal data indicating that approximately 40 percent of private jet flyers are actively interested in sharing their flights if the right digital tools are available. To capture this segment, the platform operates on a membership-driven ecosystem governed by three core functional pillars:

1. Host: A user charters a private jet and acts as the flight coordinator. Hosts retain complete control over visibility, choosing to open the remaining seats exclusively to direct friends, mutual friends, or the entire network of FlyWith members. Furthermore, hosts can bundle seats (e.g., retaining four cabin seats for themselves while putting another four up for grabs) and either let the app automatically calculate proportional cost-splits or manually set custom seat pricing.
2. Join: Members can browse the application’s active interface to discover, apply for, and secure open seats on flights hosted by other verified travelers heading to overlapping destinations.
3. Propose: A collaborative feature that allows members to float upcoming travel itineraries within the network to gauge interest and secure travel companions before finalizing a costly charter booking.

Aircraft and Fleet Partners

To ensure uncompromising safety, comfort, and reliability, FlyWith has partnered with Executive Jet Management (EJM), tapping into NetJets’ sprawling operational network. The service primarily utilizes super-midsize and large-cabin aircraft, providing spacious cabins equipped with eight to ten seats. This ensures that even when flights are shared, passengers retain ample personal space, legroom, and privacy.

Official Responses and Industry Perspectives

The leadership team behind FlyWith views the platform not as a disruptor of legacy aviation models, but as an intelligent optimization layer.

"We’ve always known that FlyWith does not replace the ways our members access private aviation today," explains CEO Brian Corbett. "So if you own your own jet, if you own a fraction of a jet, if you have a jet card, if you charter, we complement those for the times when sharing the experience and cost is better."

Corbett emphasizes that the emotional core of the platform is "serendipity"—the ability to transform isolated travel into a shared social experience. He notes that while people frequently bump into colleagues at conferences in New York or friends at wedding destinations, the missed opportunities to coordinate travel beforehand have long represented an inefficiency in luxury transit.

Addressing potential concerns regarding safety and community standards when flying with unfamiliar members, Corbett remains confident. Because the user base is curated through strict partnerships with elite clubs like Zero Bond and Discovery Land Company, the applicant pool is heavily vetted. Additionally, FlyWith enforces strict community guidelines governing conduct before, during, and after every flight, backed by protocols to swiftly handle any interpersonal conflicts should they arise.

Implications for the Future of Luxury Travel

The launch of FlyWith signals a broader cultural shift within high-net-worth circles toward collaborative consumption, where luxury is no longer defined strictly by isolation, but by enhanced connectivity and resource efficiency.

Economic and Environmental Synergies

While cost-splitting is a primary driver for members—allowing charter clients to offset significant hourly rates—the secondary implications for sustainability are notable. By consolidating travelers onto fewer aircraft heading to the same destinations, platforms like FlyWith naturally reduce the total volume of empty-leg flights and fractional fuel burn per capita. Though private aviation will remain an exclusive luxury, optimizing cabin occupancy represents a tangible step toward modernizing the industry’s environmental footprint.

Redefining Networking in the Skies

For decades, private aviation terminals (FBOs) have functioned as quiet, segregated sanctuaries where networking is purely accidental. By digitizing flight intents, FlyWith turns the private terminal into a dynamic networking hub. Business leaders, entrepreneurs, and cultural tastemakers can intentionally align their travel schedules to foster professional collaborations or deepen personal relationships at 41,000 feet.

Looking Ahead

As FlyWith transitions from its initial North American rollout to a broader global roadmap, its success will serve as a bellwether for how technology can introduce community-driven efficiencies into traditionally insular markets. By respecting the strict security and privacy demands of ultra-wealthy clientele while injecting a modern, app-native sharing ethos, FlyWith is poised to permanently alter how the world experiences private flight.