• Home
  • News
  • Fortune 500
  • Tech
  • Finance
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
SuccessBillionaires

The world’s youngest self-made billionaire says the secret to closing deals is exploiting investors’ greed and fear of missing out

Dave Smith
By
Dave Smith
Dave Smith
Editor, U.S. News
Dave Smith
By
Dave Smith
Dave Smith
Editor, U.S. News
August 26, 2025, 1:32 PM ET
Photo of Thomas Healy
Thomas Healy, founder and chief executive officer of Hyliion, says to focus on winning and don’t even see failure as an option.F. Carter Smith / Bloomberg—Getty Images
  • Thomas Healy, the 33-year-old founder and CEO of Hyliion, recently shared his take on high-pressure dealmaking in an interview with the School of Hard Knocks, a rapidly growing TikTok channel known for spotlighting entrepreneurs and modern business luminaries. Healy said his core negotiating advice is all about leverage and never getting “into a position where you’re desperate.”

Thomas Healy founded Hyliion in 2015 when he was a grad student at Pittsburgh’s Carnegie Mellon University. Ten years later, Hyliion has raised over $750 million, gone public via a SPAC merger, and achieved a valuation of $1.6 billion, making Healy the youngest self-made billionaire in America. He toppled the previous title holder, Kylie Jenner, in 2020.

In an interview with the School of Hard Knocks, a popular TikTok channel cofounded by two brothers and graduates from University of Texas’s McCombs School of Business, Healy was asked for his best negotiating advice “that could change someone’s life.”

“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.

Hyliion didn’t immediately respond to Fortune’s request for comment.

Fortune Brainstorm AI returns to San Francisco Dec. 8–9 to convene the smartest people we know—technologists, entrepreneurs, Fortune Global 500 executives, investors, policymakers, and the brilliant minds in between—to explore and interrogate the most pressing questions about AI at another pivotal moment. Register here.
About the Author
Dave Smith
By Dave SmithEditor, U.S. News

Dave Smith is a writer and editor who previously has been published in Business Insider, Newsweek, ABC News, and USA TODAY.

See full bioRight Arrow Button Icon
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

© 2025 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.