10 Things You Didn’t Know About Wheels CEO Kenny Dichter

Wheels is a membership firm that provides on-demand aircraft. It allows clients hire planes from the Wheels Up app for short or long-term agreements, and provides them exclusive use of the aircraft. The business model is different because it saves the client the hassle of actual plane ownership, while offering the flexibility of on-demand car rentals for planes. Kenny Dichter is the man behind this ingenious venture. Below are 10 things you probably didn’t know about him.

1. Is available on both Twitter and LinkedIn

Kenny Dichter is visible on social media with profiles on both Twitter and LinkedIn.

2. Started from humble beginnings

Dichter did not start with money. He grew up on Long Island and got his first job while in sixth grade where he delivered newspapers in the afternoon on weekdays and Sundays. An entrepreneur at heart, he started a T-shirt business while studying at the University of Wisconsin. By the time he graduated in 1990, the business had expanded to three retail locations. His love for jets and the potential for Wheels Up was born in 1998. By then he was 49 and had a business meeting to attend in South Carolina. A friend lent him his jet to travel from Teterboro Airport in New Jersey to Kiawah Island in South Carolina. He recalls turning to his business partner and telling him, “we gotta make a business out of this.” It was “love at first flight,” Kenny told CNBC.

3. Is a serial entrepreneur

The encounter on a private jet birthed his first aviation business, the Marquis Jet. Marquis Jet was the company through which he met Warren Buffett. However, this is just one out of a series of businesses Kenny has been involved in. He is involved in start-ups with the potential for huge growth. I.e Juice Press is an organic raw juice and raw food company. SportYapper is a global sports communications platform. CYC was an indoor cycling studio for young professionals and students at universities in America. Cirrus is a fitness company retailing customized and premium exercise equipment. Other businesses include:

  • Alphabet City Sports Records – Alphabet City Sports Records was a label selling songs commonly heard in stadiums and sports arenas. He started the business shortly after graduating from the University of Wisconsin in partnership with Jesse Itzler. He grew the business and eventually sold it for $4.3 million to SFX Entertainment in 1998.
  • Tequila Avión – The winners at the 2012 San Francisco World Spirits Competition in the ‘Best Tequila in the World’ and ‘Best White Spirit in the World’ awards were brands from Tequila Avión. The company was founded by Kenny and Ken Austin.
  • Wheels Up – Wheels Up, according to Dichter “is more Netflix than Netjets.” Wheels Up is a subscription business. The business model increases the market for private aviation. Clients hire jets for as little as a couple of hundred thousand to a couple of million. The customer does not own the jet. Wheels Up owns the jet and absorbs the upfront costs of private flights. It is a very flexible business model as the company app provides a fleet available on-demand. Customers can be individuals and corporate members.

4. Winner of the 17th Annual Living Legends of Aviation Award

At the Annual Living Legends of Aviation Award, Kenny Dichter was recognized for democratizing the private aviation space. At these awards he was presented with the prestigious Eren Ozman Entrepreneur of the Year Award. The recognition looks at turnkey additions to the industry, such as innovation and the use of technology.

5. Integrated the use of technology in the aviation industry

Groundbreaking innovation is one of Kenny’s major strengths. He signs deals, many of which are firsts. In October 2019 he was hailed for his development of technology platforms. The agreements signed have led to the digitization of the aviation sector. These are pioneering moves that make flying private more accessible to a wider market.

6. Is a sociology major

Kenny, a Sociology major, graduated from the University of Wisconsin and continued on his path of building and selling businesses. He has a good eye for a business name that will sell. Kenny is an expert at marketing, product branding, and creating winning public relations campaigns. He brings necessary skills to business and many of them are effective across industries.

7. Sits on boards to transform perceptions

Perceptions are important and especially on how people view tragedy. Kenny Ditcher sits on the Board of Action America, an organization he founded to help bring Americans together after the 9/11 tragedy. Together with the Chairman and CEO at AOL, Tim Armstrong, the organization helps to refocus positive perception and propel positive action.

Kenny chairs the Council of Advocates at New York’s Mount Sinai Hospital. He sits on the board with the CEO and Chairman of Mount Sinai Hospital, Dr. Ken Davis. Together they introduce and entrench better practices of treatment in pediatric and oncology departments.

8. Can speak his way into a mega-deal

Marquis Jets, founded in 2001 was the first fractional card jet program. It quickly grew to 3500 customers. Dichter eventually sold Marquis Jets to Warren Buffett’s Berkshire Hathaway as a subsidiary. To convince a multi-billionaire such as Warren Buffett to sign on for a deal is nothing short of genius. One would be forgiven to assume that at the time of signing a deal with Warren Buffet, Kenny Dichter was at the same financial level as Buffet, but he wasn’t. His ability to negotiate enables him make high-stakes business deals. “Working with Warren Buffett is like playing basketball with Michael Jordan,” Dichter says.

9. Is CEO of a company with its fleet of 80 planes

Wheels Up has a fleet of over 80 aircraft. The company signs up a client on a one-time membership initiation fee with annual dues payable at the beginning of the following year. The membership gives the client access to the on-demand aircraft. The membership structure provides for both individual/family membership and corporate membership. The members pay a fixed hourly rate for occupied flight hours, making the model very attractive for users.

10. Is eyeing the next frontier in merging private and commercial aviation

His latest deal is an agreement between Wheels Up and Delta Airlines. The agreement will merge private jets from Delta Airlines with private jets from Wheels Up. This paves way for merging the flying experience between commercial and private aviation.


Kenny Dichter is a man who trades with investors with big names and an even better reputation. His latest deal will see him work on an investment plan alongside financial giants like Franklin Templeton, Fidelity and T. Rowe Price. After all, he is a man with the energy to go after the best deals.

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