• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Meet the 33-year-old CEO betting on boomers chasing their grandkids—and millennials selling their first house

2

How Scott Bessent used financial engineering to finance the $2 trillion deficit while leaving it untouched—and created a $1.45 trillion shortfall

3

Iranian officials are worried the U.S. blockade will cause an economic collapse and admit sanctions relief is desperately needed

1

Meet the 33-year-old CEO betting on boomers chasing their grandkids—and millennials selling their first house

2

How Scott Bessent used financial engineering to finance the $2 trillion deficit while leaving it untouched—and created a $1.45 trillion shortfall

3

Iranian officials are worried the U.S. blockade will cause an economic collapse and admit sanctions relief is desperately needed
SuccessBillionaires

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

By
Dave Smith
Dave Smith
Former Editor, U.S. News
Down Arrow Button Icon
By
Dave Smith
Dave Smith
Former Editor, U.S. News
Down Arrow Button Icon
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
Add Fortune on Google for similar content.
  • 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 Daily breaks the traditional barrier between audience and newsroom. The show transforms Fortune’s trusted reporting into actionable, conversational, and entertaining insights for an emerging class of business leaders. Watch here.
About the Author
By Dave SmithFormer Editor, U.S. News

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

See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in Success

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • 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
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • TikTok icon
  • YouTube icon

Latest in Success

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

© 2026 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.