De Leon recalled in a recent interview with The Wall Street Journal being told by one boss, “you should find something else to do” at the start of his career.

“Basically it was, ‘Hey, man, you may be the worst analyst that Goldman Sachs has ever hired.’”

The self-made billionaire was surprised to hear the criticism, but he now credits it with changing his life for the better. De Leon began his career as an analyst Goldman Sachs in 2001 after receiving his bachelor’s degree from Harvard University. But after just a couple of years, his peers at the global bank recognized that his true potential lay outside of the company. He was lauded for his entrepreneurial chops while effectively being shooed out of the powerful firm; but leaving the Wall Street institution proved to be a blessing in disguise in propelling his career to its current height. 

“He said, ‘Look, someday you’ll come back as a client of this firm, but today you really got to go find something else.’ And it was great advice,” De Leon said. “For five seconds, it was hurtful, but then it turned out to be the best thing that ever happened, because it was true. I belonged out there in the wild, building something.”

The Gen Xer founded his business with around $100K saved from Goldman bonuses and childhood money

The Texas-born businessman says he left Goldman Sachs with around $80,000 to $100,000 in savings from Goldman bonuses, extra money from growing up, and interest from some of his buildings. 

And from there on out, De Leon delved head-first into his real estate career by beginning to option land: paying an upfront fee for the exclusive right to buy a piece of land at a set price and timeline. 

In the early years, the billionaire said he made some bad deals and considered leaving the industry behind, convinced he wasn’t going to make it. 

“I had a string of bad deals. I had made enough mistakes where I was almost done,” De Leon explained, telling his wife he was going to look for a regular job. 

“She said ‘Look, you can’t do that, because if you do that, you’re going to drive me crazy. You can’t work for anybody, you’ve got to go out there, get back up one more time. Just try it again… You’ve got to believe in yourself.” And the rest is history.

In 2006, he founded Leon Capital Group, which started as a modest real estate development company operating out of Texas. The company has since expanded into financial services and healthcare; De Leon himself has made real estate investments with an asset value of more than $15 billion. 

Through his success across industries, 47-year-old De Leon is now estimated to be worth a whopping $3.1 billion.

Meet the leaders who have turned rejection into billion-dollar comebacks

Just like De Leon, every worker will face a rejection or letdown at some point in their professional lives—but some are turning lemons into lemonade. 

Julia Stewart—a serial executive who has led operations across various billion-dollar American casual dining chains—once had a gratifying career moment after being snubbed for CEO. 

It was 1998, and Stewart was serving as president of Applebees. The then-struggling restaurant chain presented a game plan to Stewart: get the struggling company back on track, and she will have proven herself enough to take the coveted chief executive role. But after spending three years transforming the business—even doubling the company’s stock during her brief tenure—her boss wasn’t satisfied when they sat down to talk about her CEO promotion. He told her, “No, not ever.”

So Stewart left the company, and found the perfect opportunity to grow another brand and get even at IHOP. In 2007, she put a major acquisition into motion: buying her former employer, Applebee’s, for around $2.1 billion to $2.3 billion. After the deal went through, she called up the company to inform them of a change in leadership.

“I called the chair and CEO of Applebee’s, and I said, ‘Just wanted to say hi.’ And he said, ‘I was expecting this call,’” Stewart reminisced on The Matthews Mentality Podcast last year. “And I said, ‘As you know, this morning, we announced that we have purchased, for $2.3 billion, the company, and we don’t need two of us, so I’m gonna have to let you go.’”

Spanx founder and former CEO Sara Blakely also faced unrelenting rejection when she first set out to get the company up and running in 1998. Having no prior business, fashion, or retail experience to show to investors, she set out with $5,000 of her own cash to make her idea into a billion-dollar empire. But at the onset, most manufacturers weren’t buying into her vision.

“They would always ask me the same three questions. They would say: ‘And you are?’ Sara Blakely. ‘And you’re with?’ Sara Blakely. ‘And you’re financially backed by?’, Sara Blakely,” Blakely told Fortune in a 2024 interview. “They’d show me the door and say ‘No, thank you.’”

By trusting her gut and continuing to fight for her business idea, Blakely would grow Spanx into a $1.2 billion shapewear success. And in 2012, she also made the ultra-rich list as the youngest self-made woman billionaire that year, according to Forbes.

And when it came to founding FedEx, one of the most nationally recognized delivery companies in the world, the idea for the billion-dollar industry titan was initially met with skepticism. 

In 1965, late FedEx founder and former CEO Frederick W. Smith first presented the basic concept for the company for an economics class assignment as undergraduate student at Yale University. But his professor couldn’t see his vision working and scored his project poorly, giving him a C. 

But Smith wasn’t deterred by a bad grade in class; after returning from service in the Vietnam War in 1971, he would set his delivery business plan in motion. Today, FedEx boasts a market cap of $98.4 billion.