Michael Dell parlayed $1,000, a University of Texas dorm room, and an appetite for risk into Dell Technologies, a company now valued at $302 billion. Along the way, he joined Steve Jobs among the American tech founders who started from the humblest of beginnings—Jobs famously cofounded Apple in a garage—and, like Jobs, dropped out of college.

For Dell, the founder, chairman, and CEO of Dell Technologies, risk-taking has been the defining thread of his career. His counsel to entrepreneurs is equally direct: trust your own judgment rather than seeking validation from others. For readers weighing a venture of their own, the advice doubles as a summary of how Dell himself has operated—leaving school, starting with $1,000, and later staking the whole company on the biggest leveraged buyout since the Global Financial Crisis.

"If you want to really make it big, you better come up with something unique," Dell told Fortune in a 2017 interview. "It better be differentiated—that nobody else is doing."

His other piece of advice is to take outside feedback with a grain of salt. Instead, he encourages people to rely on their gut instincts when weighing whether a new product or business idea will succeed over the long run.

"If you go and ask people if it's a good idea, most of them will tell you no," Dell told Fortune. "So don't go ask."

From pre-med to PC empire

Dell enrolled at the University of Texas in 1983 as a pre-med student, a choice made largely to please his parents, according to Entrepreneur. Computers, however, had long fascinated him: at age 15, he disassembled an Apple II to see how it worked, according to his 1999 biography, Direct From Dell: Strategies That Revolutionized an Industry.

At 19, he began selling personal computer upgrade kits to fellow students out of his dorm room—the move that launched his tech empire.

Dell Technologies was born from risk. Only partway into his college career, Dell had just $1,000 to invest in the business, and his manufacturing team consisted of "three guys with screwdrivers sitting at six-foot tables," he recounted in Direct From Dell.

"You have to embrace risk, and you have to accept failure," Dell told Fortune.

The entrepreneurial streak predated the company. While attending Memorial High School in Houston, Dell sold subscriptions to the Houston Post (later acquired by the Houston Chronicle). Rather than relying on the classic cold-call technique, he honed a far more effective approach of targeting specific populations, earning $18,000 in a single year—more than some of his high school teachers made, according to a 2021 episode of Fortune's Leadership Next podcast.

His insight was that newlyweds were more likely to buy newspaper subscriptions. Using Freedom of Information Act (FOIA) requests, he obtained marriage licenses—and, with them, the addresses of the people he judged most likely to subscribe.

"Jackpot!" Dell said in the 2021 podcast. He then deployed those addresses in direct-mail campaigns and even hired a few friends to help with the venture.

Public, private, and public again

The direct-marketing playbook learned selling newspapers would later fuel the company's rise. By age 27, Dell had become the youngest CEO in the Fortune 500, in 1992. By 2001, Dell was the world's largest personal-computer maker, its 1990s success owing much to a similarly innovative direct-marketing strategy.

The company's trajectory as a public, then private, then public company has been headspinning. In 1997, Dell was valued at over $120 billion, while Apple was floundering at $2.3 billion—valuations that have since flipped, as Apple grew into one of the world's most valuable companies, a reminder of how quickly standing can shift in tech. Yet the company's devotion to its core PC business threw it for a loop after the dot-com crash, and by 2007, slower sales and greater competition made change unavoidable.

"The direct model has been a revolution, but it is not a religion," Dell wrote in an April 2007 memo to his 80,000 employees.

"Many believed that it was a dying company that would perish like Kodak or Motorola," according to a report by Cascade. Leadership changes and new corporate strategies followed, and Dell's knack for creative solutions repeatedly breathed new life into his creation.

The founder ultimately took Dell private in 2013 for $24.4 billion, the biggest leveraged buyout since the Global Financial Crisis. With help from private equity sponsor Silver Lake, he retooled the company, most notably through the $67 billion acquisition of EMC Corp., a data-storage leader, in 2015—the highest-valued tech acquisition at the time and the deal that anchored Dell's expansion into enterprise storage and data-center infrastructure. Dell re-listed in 2018 at a $16 billion market cap, which has since climbed to $302 billion, as of Oct. 30.

Michael Dell's own fortune has surged alongside: his net worth is estimated at $234 billion by the Bloomberg Billionaires Index. In 2025, he and his wife, Susan, pledged $6.25 billion to seed Trump Accounts—federally created investment accounts for children established under 2025 legislation—for millions of American children.

Risk as a competitive advantage

Dell told Fortune that risk-taking has been his greatest advantage in business—and a downfall for other major corporations.

"Big companies generally [aren't good at taking risks]," Dell said. "If you talk about risk, they'll talk about the risk reduction, and the risk committee, and the risk management, and all those say the risk is bad. Well, if you don't have risk, you don't have innovation."

Indeed, Dell says his company does "all sorts of things internally to promote risk innovation," including investing billions of dollars in research and development.

"We've got hundreds of projects, and they're not all going to work out," Dell told Fortune. "That's okay."

A version of this story appeared on Fortune.com on November 17, 2025. This story was originally featured on Fortune.com.