Turning Private Aviation into a Lifestyle Brand Built to Scale

President & Partner of SWAT. I joined SWAT as Wheels Up was entering its next chapter, helping evolve an already bold brand into a fully realized lifestyle platform and IPO-ready business, pairing a disruptive aviation model with world-class brand, culture, and momentum.

A Category-Changing Idea, Built by Insiders

Wheels Up was never just another private aviation company. Founder Kenny Dichter, who previously launched Marquis Jets and ran NetJets post-acquisition, set out to build something fundamentally different: the first accessible private aviation company that owned its fleet, not a charter marketplace pretending to be one.

The business model was visionary. Practical flights. Predictable access. An “SUV in the sky” designed for real usage, not just status. Kenny knew the category better than anyone and had the charisma, instincts, and credibility to bring people along for the ride.

Richard Kirshenbaum and the original SWAT team laid powerful groundwork, defining the brand positioning and capital-raising narrative that helped get Wheels Up off the ground.

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Entering at Brand 2.0

When I joined Richard as President and Partner of SWAT, Wheels Up was about a year and a half into its journey. Woody Wright was already doing excellent work as account lead, and together with a refreshed creative and strategic team, we focused on evolving the brand from launch mode into a seamless next phase.

This wasn’t about reinvention. It was about elevation.

We sharpened the strategy, expanded the storytelling, and helped transform Wheels Up from a disruptive startup into a fully dimensional lifestyle brand built for scale, culture, and long-term growth.

Access, Culture, and Credibility

One of the smartest moves was leaning into brand ambassadors who actually embodied the Wheels Up mindset. Not endorsements for hire, but real believers.

We helped scale a top-tier ambassador ecosystem including Tom Brady, Serena Williams, Lindsey Vonn, Wayne Gretzky, JJ Watt, Rickie Fowler, and others. Each partnership included original interviews, photography, and video content that brought credibility, humanity, and aspiration to the brand.

This content, shot by Jesse Dittmar early in his career, captured Wheels Up as both elite and approachable, premium without being precious.

Making Private Aviation Feel Usable

The strategy was rooted in practicality. Wheels Up focused on two to three hour flights used multiple times a day by members for business, family, and lifestyle needs. This was not about champagne theatrics. It was about replacing long drives with smart, efficient travel.

The brand showed up accordingly across CNBC, digital platforms, and owned channels, speaking to both individual members and enterprise clients. The message was clear: private aviation, reimagined for how people actually live and work.

Results That Spoke Loudly

Grew membership to over 3,000 members within the first three years
Became the most successful private aviation launch in U.S. history
Achieved a valuation of approximately $1.1B
Successfully went public on the NYSE under ticker UP in September 2020

Takeaway

Wheels Up worked because the business strategy was genuinely disruptive and the brand knew how to keep up. My role was to help evolve that momentum into a scalable, culturally relevant platform that could support the weight of its ambition.

It was glossy, fast, and fun. But underneath it all was discipline, strategy, and an unwavering focus on access over excess. When innovation meets clarity and culture, categories don’t just shift. They reset.

WHEELS UP