From $40 to $350 Million: What Daymond John Wishes He'd Known About Business

When Daymond John built FUBU from a $40 budget into a $6 billion fashion powerhouse, he wasn’t just creating a clothing brand—he was learning lessons the hard way. Now, as a Shark Tank investor and 55-year-old business mentor, John looks back at his journey with unflinching clarity about what derailed him most in his path to that $350 million net worth.

The perspective he shares isn’t about market timing or product strategy. It’s something far more fundamental.

The Attitude That Kills Relationships

In reflecting on the worst counsel he’s encountered, Daymond John pinpoints an uncomfortable truth about how successful people operate. Some advisors told him that once you have capital, people become expendable—disposable assets in your climb upward. John rejects this entirely.

“When you discard people, that’s horrible,” he explains. This mindset, he believes, represents a corruption of wealth itself. Money doesn’t grant permission to treat individuals as temporary tools. Whether someone has little or significant resources, this philosophy of abandonment creates hollow success.

The Hidden Bankruptcy: Lacking Financial Foundations

John’s own story includes a cautionary pattern most entrepreneurs don’t discuss openly. He nearly collapsed financially three times throughout his career—twice while broke, and once while profitable. The culprit wasn’t bad luck or market forces. It was a single missing ingredient: financial intelligence.

Growing up without generational wealth knowledge changed his trajectory. Unlike families with established money traditions passing down investment wisdom, John had to teach himself. “We didn’t have a grandfather to explain these things,” he recalls. Even information access was limited decades ago. The gap between opportunity and understanding nearly destroyed what he’d built.

Why 65% of the Highest Earners Go Broke

This deficit in financial literacy extends far beyond entrepreneurs like John. Research shows that approximately 65% of professional athletes and lottery winners face bankruptcy within three years of leaving their sport or collecting their winnings.

The culture responds with judgment: “They blew it.” But John challenges this narrative sharply. These individuals competed against millions to reach elite status. Their failure wasn’t character—it was education. Nobody taught them money management. As John frames it: “You don’t know what you don’t know.”

Building the Next Generation Differently

Recognizing this systemic failure, John launched “Little Daymond Learns to Earn,” a project designed to shift how schools and institutions approach financial education. His goal isn’t merely publishing—it’s catalyzing institutional change. He’s working to embed financial literacy into school systems across major cities, partnering with celebrities, banks, and educational organizations to normalize this conversation.

The mission is personal. If the wealthiest and most talented people in America can become financially devastated through ignorance, then everyone deserves better preparation. For John, this becomes the ultimate business lesson: the advice worth giving isn’t about making money—it’s about keeping it, understanding it, and passing along what previous generations withheld.