The Pursuit with Kelsey Humphreys

The Pursuit with Kelsey Humphreys is an insightful and entertaining in-person, video talk show featuring today’s most successful people like Tony Robbins, Barbara Corcoran, Gary Vaynerchuk, HGTV’s the Property Brothers, Chalene Johnson, Michael Hyatt and more! Each episode features an in-depth interview where guests explain how they got to where they are today and their best advice for anyone who wants to achieve success, but may feel stuck, overwhelmed, or unsure of where to start. Every episode Humphreys breaks down digestible, doable takeaways from the interview and gets the guest to let loose, have fun and offer an awesome giveaway to listeners.
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The Pursuit with Kelsey Humphreys


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Dec 14, 2016

The story of the hustling D-student who built a business from a dorm room never gets old, which is why I loved interviewing Kenny Dichter. That’s exactly how the serial entrepreneur, now the CEO and founder of Wheels Up, got his start. But what sets Dichter apart is his track record since then: building and selling one successful business after another.

In college, Dichter and a friend began creating and selling T-shirts with “Wisconsin flair” at the University of Wisconsin-Madison. The apparel line started to gain traction, so Dichter moved the operation from his dorm to a nearby storefront. That business grew to three locations before Dichter sold it upon graduation.

After his first success, the father of one of his friends, a clothing manufacturer, decided to back Dichter’s next apparel venture. His operation moved from Wisconsin to New York City, and he was soon fulfilling orders for the likes of Wal-Mart and Sears. As the company reached a tipping point, Dichter decided to sell it and start a new venture, a process he would repeat over and over again.

His next business took him into the world of sports marketing. His friend Jesse Itzler, a jingle writer, saw an opportunity to build a business around the music that played in arenas during sporting events. Dichter provided the strategy for Itzler’s idea, and the two sold that business to SFX Entertainment for more than $4 million in 1998.

By that point, Dichter had experienced substantial success firsthand, and he noticed that no one in his social circles flew commercial anymore. On one of his first private flights, the idea for Marquis Jet was born. Marquis Jet was the first aviation option that allowed members to reduce travel costs by buying blocks of hours on a pre-paid card instead of purchasing their own aircraft. Again, Dichter grew his idea and made an exit, selling Marquis Jet to Warren Buffet’s NetJets in 2010. Before returning to aviation with Wheels Up in 2014, Dichter built and sold another business, Tequila Avion, an ultra-premium brand that sold for $100 million.

His latest success offers the private aviation industry a membership model without spending requirements or hourly minimums. Wheels Up raised $115 million in funding in February 2016, and according to Ditcher, it now holds a valuation of $521.5 million with a projected worth of $1 to $1.5 billion by 2020.

Clearly, Dichter knows what he’s doing. Here is his advice for entrepreneurial success.

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