“Never get into a position where you’re desperate,” Healy said. “That’s where things usually go wrong. You need to be willing to walk away when it doesn’t make sense.”
Healy said he once had an investor change the terms of the deal on him the night they were going to close. “So that evening, I flew to Florida, met with a different investor, and the following day signed the entire deal with a totally new investor. You gotta always keep a plan B.”
Healy said one of the best lessons he learned—and a key to making it in business—is to understand that all investors have intrinsic FOMO, or fear of missing out, and to leverage that psychology in dealmaking.
“If they’re looking at your company, you need to make them realize that they don’t want this to be the company they missed out on,” he said. “You gotta create fear that they might miss out on this deal. But you also have to create greed—that if they want to be in this, they want to really be in this and invest heavily in you.”
While Hyliion has been challenged in recent years—it pivoted from developing hybrid electric-truck powertrains in 2023 to focus entirely on its stationary, zero-emission generator technology for power plants and specialized customers, called the KARNO Power Module—Healy says he still follows a guiding principle he learned from one of his early investors, who is also a billionaire.
“He said, ‘Winning is your only option.’ You can’t think about, what ways could I potentially lose at this? How could we fail? It has to work, or it has to work,” Healy said.
