For elite travelers, the scenario is painfully familiar: you arrive at a private Fixed-Base Operator (FBO), preparing to board a chartered Gulfstream to Aspen, only to bump into an old friend or a prominent industry colleague heading to the exact same destination on a completely separate aircraft. Moments like these—whether sparked by a major conference in New York, a high-profile wedding in Europe, or a weekend getaway—inevitably trigger a wave of missed opportunities. You are left wishing you had known of each other’s travel plans ahead of time so you could have coordinated your itineraries, elevated the journey’s social experience, and split the considerable financial burden.
Enter FlyWith, an innovative, invitation-only membership platform designed to eliminate empty seats in the private aviation market. Founded by Sound Ventures co-founder Guy Oseary and led by veteran luxury hospitality and aviation executive Brian Corbett, FlyWith is poised to disrupt the status quo. The app allows travelers to seamlessly share private jet flights with friends, mutual acquaintances, or approved fellow members before ever stepping onboard. By handling payments, aircraft selection, and trip organization within a unified digital interface, FlyWith is turning the often-isolated world of private jet chartering into a collaborative, community-driven ecosystem.
Rather than competing with existing fractional ownership models, jet cards, or whole-aircraft charters, FlyWith occupies an untapped "white space" in the industry. It acts as a complementary layer designed specifically for those moments when sharing the experience—and the cost—makes far more sense than flying solo.
Chronology
The journey from concept to reality for FlyWith reflects the fast-paced, high-stakes nature of modern venture-backed enterprise:
The Conceptualization: The idea was originally sparked by Guy Oseary, co-founder of venture capital firm Sound Ventures. Recognizing a glaring inefficiency in how private jet charters were booked and utilized, Oseary envisioned a social network for the skies. He soon brought in Brian Corbett, whose extensive background included leading luxury hospitality brands like Inspirato and Exclusive Resorts, alongside managing private aviation infrastructure company Ross Aviation, to serve as Chief Executive Officer.
Partnerships and Fleet Integration: To ensure operational excellence and access to top-tier hardware, FlyWith forged a strategic partnership with Executive Jet Management (EJM), a subsidiary of industry giant NetJets. This alliance granted FlyWith clients immediate access to an expansive, highly reliable fleet of super-midsize and large-cabin aircraft.
Vetting and Brand Collaborations: To curate a trusted user base, FlyWith established strategic alliances with premier private social clubs and exclusive lifestyle brands—including Discovery Land Company, Zero Bond, and the Crane Club. These partnerships allowed the platform to leverage established vetting processes to source its initial cohort of high-net-worth members.
Private Trials and Testing (August – September 2026): FlyWith initiated a quiet beta trial phase with select members in August, refining its digital infrastructure and payment rails.
First Commercial Test Flights (September 2026): The platform completed its inaugural test flights earlier this month. According to executive leadership, the integrations with operator partners proved entirely seamless, successfully accommodating hyper-specific luxury requests down to stocking glass bottles and eliminating single-use plastics onboard.
Official Public Launch (October 2026): FlyWith is scheduled to make its official debut in October 2026 across North America, operating on an invitation-only model with pricing details revealed upon membership acceptance.
Supporting Data and Platform Mechanics
Despite the ultra-luxury nature of its assets, FlyWith’s digital architecture is designed for simplicity, evoking the user-friendly mechanics of mainstream consumer apps like Airbnb. The platform operates around three core user actions, supported by robust fleet capabilities and a carefully curated vetting framework.
The Three Core Flight Modes
FlyWith breaks down its user experience into three distinct operational pathways:
Host: Designed for the primary traveler chartering an aircraft. As a Host, you retain total control over how the cabin is shared. You can restrict invitations to your personal contact list, expand them to mutual friends, or open the flight up to the entire global FlyWith member directory. Furthermore, Hosts can customize cabin configurations—such as reserving a four-seat block for private use while offering an adjacent four-seat bundle for sharing—or list individual seats. The app automatically calculates per-seat cost splits, though Hosts retain the flexibility to adjust pricing as they see fit.
Join: A streamlined browsing interface that allows members to search the live directory of upcoming flights hosted by other users and secure a vacant seat with just a few taps.
Propose: A collaborative planning tool that enables members to float hypothetical itineraries, gauge interest from fellow travelers, and build out shared charters before officially committing funds or locking in a booking.
Fleet and Aircraft Partnerships
FlyWith’s partnership with Executive Jet Management (EJM) ensures that its members fly aboard industry-leading aircraft. The platform primarily utilizes super-midsize and large-cabin jets—such as top-tier Gulfstream and Bombardier models—typically featuring eight-to-ten-seat configurations that offer ample legroom, dedicated galley spaces, and high-end cabin amenities.
Membership Vetting and Security
To maintain the security, privacy, and exclusivity expected by private aviation clients, FlyWith relies on a strict admission framework. By partnering with elite enclaves like Zero Bond, Crane Club, and Discovery Land Company, the platform taps into pre-vetted pools of affluent individuals. For flights involving strangers matched via the app, FlyWith enforces strict community conduct guidelines governing behavior before, during, and after the flight.
Official Responses and Industry Insights
The industry response to FlyWith has been overwhelmingly positive, driven by the realization that private aviation has long suffered from structural inefficiencies.
Reflecting on his initial reaction to the business model, CEO Brian Corbett recalled his conversation with founder Guy Oseary:
"The first question I asked Guy Oseary when we talked, when he first introduced the concept, was, ‘Are you sure that this doesn’t already exist? It makes so much sense.’ And sure enough, it didn’t exist."
Corbett emphasizes that the app is fundamentally rooted in the concept of "serendipity"—a deliberate attempt to capture organic, real-world connections before they happen, rather than documenting them after the fact.
"We refer to it as serendipity, right? Knowing where your friends are going before they actually go," Corbett explains. "With all other social networks today, you know where people are when they’re there because they’re sharing, or you know where they’ve been because they share when they get back. This way [with the app], you can actually maybe take a trip that you weren’t even imagining going to."
Crucially, Corbett is quick to position FlyWith as an enhancement to the existing private aviation landscape rather than a disruptive threat to traditional brokers or fractional operators.
"We’ve always known that FlyWith does not replace the ways our members access private aviation today," he notes. "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."
Implications
The launch of FlyWith carries profound implications for the luxury travel sector, the private jet charter market, and high-net-worth social dynamics.
1. Economic Optimization and Sustainability
The private aviation industry has historically faced criticism regarding its carbon footprint and operational inefficiencies, specifically the high volume of flights operating with empty seats. By optimizing cabin capacity through peer-to-peer sharing, FlyWith introduces a pragmatic layer of resource efficiency to the market. While private jets will always remain an exclusive luxury, spreading passenger loads across fewer total flights helps address both economic and environmental concerns.
2. The Gamification of Elite Networking
By combining high-end travel with social discovery, FlyWith transforms booking a flight into a networking opportunity. Business executives, entrepreneurs, and cultural tastemakers can now strategically position themselves on shared flights, turning routine transit times into high-value professional or social interactions.
3. Future Expansion and Scaling
As FlyWith prepares for its October 2026 debut, its initial rollout will be tightly restricted to North America. However, the roadmap already includes international expansion into key global aviation corridors—such as London, Geneva, Dubai, and Singapore—once the domestic market infrastructure is fully optimized.
Ultimately, FlyWith is bridging a gap that has existed since the inception of business aviation. By fusing cutting-edge digital logistics with vetted social connectivity, the app is proving that even in the most exclusive tier of travel, sharing the journey is not only more economical—it’s infinitely more rewarding.
