Having raised hundreds of millions of dollars, in June 2019, Dichter bought TMC Jets, with a fleet of 26 Hawker 400XPs. For the first time, Dichter owned an actual airline instead of just selling flights on airplanes operated by a third party. Asked if there were more transactions in the pipeline, Dichter told Private Jet Card Comparisons, "It's safe to say we're in the deal-making mode," adding, "Wheels Up wants to be a total provider of global private aviation solutions." The race was on. He acquired four more charter operators with six operating certificates, a charter broker, and a technology company. He also launched an aircraft brokerage unit. In December 2019, with a $1.1 billion valuation from its most recent raise, Dichter made his most important deal. Delta agreed to sell its Delta Private Jets unit to Wheels Up for a 28% stake.