Thomas Healy Uses Fear and Greed to Negotiate Billion-Dollar Deals

Thomas Healy, 33, the founder and CEO of Hyliion, has become the youngest self-made billionaire in the U.S., with a $1.6 billion valuation following a 2025 SPAC merger. In an interview with “The School of Hard Knocks,” a popular TikTok channel, he discussed his approach to dealmaking, emphasizing the use of psychological leverage rooted in investors’ fear and greed [1]. Healy, who launched Hyliion in 2015 while a graduate student at Carnegie Mellon University, has since raised over $750 million and navigated multiple business pivots, most recently shifting the company’s focus from hybrid electric-truck powertrains to zero-emission stationary generator technology [1].

Central to Healy’s philosophy is the idea of avoiding desperation in negotiations. He advised that being in a position where one is perceived as needing the deal increases the risk of unfavorable terms. “You need to be willing to walk away when it doesn’t make sense,” he stated [1]. He illustrated this with an anecdote from his career: when an investor changed deal terms the night before a closing, Healy flew to Florida, met with a new investor, and secured the deal within 24 hours. He described this adaptability as essential to business success [1].

Healy also highlighted the importance of understanding and leveraging investors’ fear of missing out, or FOMO. According to him, creating both fear and greed in potential investors can be a powerful tool in negotiations. He urged entrepreneurs to communicate that an investment in their company is not just an opportunity but a necessity—something investors cannot afford to miss [1].

This approach aligns with a mindset instilled in him by a billionaire investor early in his career: “Winning is your only option.” Healy explained that this philosophy removes the possibility of failure as a planning consideration and focuses energy entirely on execution [1].

His insights reflect a growing trend in modern business where emotional intelligence and psychological strategy are as important as financial expertise. While Hyliion has faced challenges and strategic shifts, Healy’s deal-making style remains grounded in calculated urgency, confidence, and the strategic use of leverage [1].

Source: [1] The world's youngest self-made billionaire says the secret ... (https://fortune.com/2025/08/26/thomas-healy-hyliion-negotiating-deals-advice-youngest-self-made-billionaire/)