Partner of Famous Stratton Oakmont: The Richard Bronson Story

What happens when a partner at the infamous Stratton Oakmont loses everything, serves prison time, and emerges homeless but refuses to give up?

When I sat down with Richard Bronson, I knew I was in for an extraordinary conversation. This wasn’t just another white-collar crime story, this was about a man who went from Wall Street riches to federal prison, then found a way to rebuild his life in the most unexpected way possible.

Richard was a partner at Stratton Oakmont, the firm made famous by “The Wolf of Wall Street.” After that empire crumbled, he launched his own firm, Biltmore Securities, growing it to over 500 employees and $100 million in business before everything came crashing down. But here’s what struck me most: when Richard got out of prison, he was homeless and destitute. Most people would have disappeared into obscurity. Instead, he created something remarkable.

From Wall Street to Federal Prison: The Reckoning

Richard’s path to Stratton Oakmont began with a chance encounter and a check that changed everything. As he told me, “My friend pulled out a check from his wallet. It was like 100,000 dollars and he goes this is what I earned last month. And I was taken aback because he was a talented guy, but he wasn’t that talented.” That moment led him to a warehouse on Long Island where young brokers were making fortunes selling penny stocks.

What made Richard different from many who got caught up in similar schemes was his brutal honesty about what they were doing. “I knew, obviously, I knew what I was doing, I was breaking the law. And furthermore, I knew the day would come that I would have to pay the price for it.” This awareness didn’t stop him, but it did lead to something unusual, before being indicted, Richard and his partner paid back every single client who had lost money.

The three-year investigation felt like slow torture, with civil lawsuits escalating to state charges, then SEC actions, and finally federal indictment. When the agents finally showed up at his office, Richard felt something unexpected: relief. The waiting had been worse than the reality.

Hurricane Evacuation: When Prison Gets Even Stranger

Prison stories usually focus on violence and despair, but Richard shared something I’d never heard before, a hurricane evacuation that turned into bureaucratic chaos. “All the sudden is an announcement, you know, on the PA system and it says grab your pillows immediately. And everyone’s like looking at. What is that? What grabbed your pillows?”

What followed was a surreal journey: 800 federal prisoners loaded onto school buses, shackled and handcuffed, driven to Alabama only to discover the receiving prison had no room for them. They ended up in Yazoo City, Mississippi, in a facility that hadn’t been opened yet, complete with cells, stainless steel toilets, and no toilet seats.

The entire experience highlighted the absurdity of the federal prison system, where a simple hurricane evacuation becomes a weeks-long odyssey through multiple states. Yet Richard found perspective even in this chaos, describing parts of his incarceration as unexpectedly peaceful, no more FBI investigations, no more lawyer calls, no more newspaper articles. For the first time in years, he could actually sleep.

From Homeless to Helping Others: The 70 Million Jobs Revolution

When Richard walked out of prison, he faced a harsh reality. Despite having paid back millions to investors, he was broke and homeless, sleeping on his sister’s couch. Many of his wealthy friends had vanished, afraid of being associated with a convicted felon. But instead of wallowing, Richard made a crucial realization.

He decided to work in reentry, not despite his criminal background, but because of it. His business experience combined with his lived experience made him uniquely qualified to help other formerly incarcerated individuals. This led him to eventually create 70 Million Jobs, a company focused on connecting the 70 million Americans with criminal records to employment opportunities.

What started as a survival strategy became a mission. Richard understood that most reentry organizations were staffed entirely by well-meaning people who had never been inside the system. He brought something different to the table, the business acumen to scale solutions and the credibility that comes from having walked the walk.

The story isn’t just about redemption, it’s about refusing to let circumstances define your future. Richard could have stayed down after losing everything. Instead, he found a way to turn his biggest liability into his greatest asset, helping thousands of others do the same.