Turning Private Aviation into a Lifestyle Brand Built to Scale

As President & Partner of SWAT, I worked closely with founder Kenny Dichter, and the broader SWAT team to help evolve Wheels Up beyond launch mode into a more expansive consumer and lifestyle platform as the business entered a critical phase of national growth.

A Category-Changing Idea, Built by an Insider

Kenny understood the aviation category intimately through his experience building Marquis Jets and later leading NetJets post-acquisition. What made Wheels Up different was not simply the service itself, but the behavioral shift behind it.

The company approached private aviation less as a symbol of exclusivity and more as a practical tool designed around how people actually wanted to move through their lives.

The model focused heavily on shorter regional flights that supported business, family, and lifestyle needs in a way that felt significantly more usable and flexible than traditional private aviation ownership structures.

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entering a brand at 2.0

When I joined Richard as President & Partner of SWAT, Wheels Up was about a year and a half into its journey. Woody Wright was already doing incredible 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.

We continued to sharpen and evolve 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. Ultimately setting the business up for a successful IPO.

Access, Culture, and Credibility

One of the smartest moves Kenny and the team was leaning into brand ambassadors who actually embodied the Wheels Up mindset. These were not transactional endorsements. They were people who genuinely fit the culture and mindset of the brand; and they were also clients.

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 consistently across CNBC, digital platforms, and owned channels, speaking to both individual members and corporate 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

Kenny Dichter was one of the most dynamic founders I’ve ever worked with. You never knew who was about to walk into his office, a world-famous athlete, investor, celebrity, or business leader. He moved fast, thought big, communicated directly, and operated with the same energy and ambition that ultimately shaped Wheels Up itself.

What made the relationship work so well was that SWAT was intentionally built to move at that same speed.

Richard structured the agency around a very senior core team capable of operating directly with founders and executives without layers of unnecessary process slowing things down. Clients were not paying for junior interpretation. They were working directly with experienced operators, strategists, and creatives who could quickly understand the opportunity, pressure-test ideas, and help move the business forward in real time.

For founder-led businesses moving at Kenny’s pace, that kind of trust, chemistry, and responsiveness becomes incredibly important.

And honestly, we had a blast building it together.