The Pursuit With Kelsey Humphreys

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