Kenny Dichter and Wheels Up doled out less than $100 million in cash to build the second-largest private jet operator with a $2 billion valuation
When Wheels Up’s acquired 5th-biggest Part 135 charter operator Mountain Aviation in January, it pushed the group past Directional Aviation’s Flexjet as the second-largest for-hire private aircraft operator in the U.S. For Wheels Up founder and CEO Kenny Dichter, it was a day at the beach compared to another cold New York winter morning in early 2019. At that point, Wheels Up didn’t operate a single aircraft. Founded in 2013, its owned and leased fleet was outsourced to Gama Aviation Signature. Wheels Up was a big brand. Yet, it was merely a marketing organization selling memberships onto what was then mainly a fleet of King Air 350i turboprops.