Partner of Famous Stratton Oakmont: The Richard Bronson Story

From Stratton Oakmont Partner to Homeless

Richard Bronson was one of the partners at Stratton Oakmont. Yes, that Stratton Oakmont. The Wolf of Wall Street firm. When I talked with Richard on the podcast, he walked me through how a journalism major from Long Island ended up in Jordan Belfort’s world, made millions, lost everything, and found himself homeless after prison.

Richard started out wanting to work in publishing. “I went to school to study journalism. And that was my plan to work in publishing or something media related, work at a magazine or a newspaper,” he told me. “But I quickly realized that there’s no money in that.” So he got a job on Wall Street. His second week? Black Monday hit in 1987. “I was watching all these other people who were experienced and smart, presumably. And the market just completely dropped like a rock,” Richard said. “It wasn’t lost on me that all of these supposed experts and pundits who we were supposed to listen to like they were oracles. They didn’t know anything.”

That early cynicism served him well. A friend eventually convinced him to check out this firm on Long Island. Richard was skeptical. This wasn’t the fancy Manhattan investment banking world he knew. “I met him and this company was based in this like warehouse in an industrial park,” Richard described. “I get there and it’s this huge open big space with row upon row of desks with mostly guys and they’re very young and they’re all standing up yelling into the phone, talking to clients.”

The commission structure was wild. While Richard was used to selling expensive NYSE stocks, these guys were selling three dollar stocks with 50 cents per share commission. “So in other words, this guy just earned $50,000 on that one phone call,” Richard said. “So I was pretty taken aback by it.”

The Rise and the Knowing

Richard met the two guys running the firm: Danny Porsche and Jordan Belfort. After doing well at Stratton, they offered him and another guy the chance to own their own brokerage firm in Florida. “We bought for very little money, a licensed firm. And part of the deal was that Stratton would help us get in business real quickly. And we would do deals together in an illicit fashion,” Richard explained.

The money came fast. “In short order, we had this big business making an enormous amount of money. And me and my partner became rich very quickly,” he said. Richard had a house on the beach next to Eric Clapton’s house. He became an art collector, bought fancy cars, had a nightclub on South Beach.

But here’s what struck me about Richard’s story. He knew exactly what he was doing. “I knew obviously I knew what I was doing. I was breaking the law. And I knew the day would come,” he told me. When I asked if he ever thought it could last forever, Richard was clear: “No, I knew that I would have to pay the price for it. I knew that one day the guys with the windbreakers with the letters on their back would come knocking on my door.”

Making Everyone Whole

What Richard and his partner did before being indicted was unusual. They paid everybody back. Every client. “We paid everybody back because it was our enlightened self interest,” Richard said. “I felt guilty about doing it, about taking their money. And I thought maybe this will make me feel a little less guilty.”

When Richard gave his allocution before the judge, he mentioned this. The judge’s response? “Yeah, but it wasn’t your money to give away. And that was when I knew I was sunk,” Richard recalled. No credit for making victims whole.

The feds offered Richard and his partner cooperation deals. His partner took it. Richard didn’t. “I said, listen, I’ll tell you about me, but I’m not going to tell you about other people. I already feel guilty enough. I don’t want to ruin other people’s lives,” he explained.

Prison Bus to Nowhere

Richard got 22 months and ended up at Eglin, the original “club fed.” The waiting period before reporting was brutal. “I tell them go as quickly as you can, because the time that you’re sentenced to the time that you actually self report, that’s the worst time of the whole thing,” Richard said. He waited over a year.

Walking into prison was surreal. “It was very literally that I’m here and I’m free. But if I take this one step, I’m walking into prison. If I go back, I’m not in prison, but if I take another step, I’m in prison,” he described.

Then there’s the hurricane story. One day at Eglin, an announcement came over the PA: “Grab your pillows immediately.” Nobody knew what that meant. They loaded 800 prisoners onto school buses, drove for hours, and ended up at another prison in Alabama. The guards went to the gate, talked to someone, came back, and the buses left. “Our prison hadn’t spoken to this other prison and this other prison didn’t have room for us,” Richard explained. They eventually ended up in Yazoo City, Mississippi.

Starting Over from Nothing

When Richard got out, he was homeless and destitute. Everything was gone. But he didn’t curl up in a corner. He got involved with reentry work, then DeFi Ventures, then started his own company called 70 Million Jobs. It was an employment platform for people with criminal records. There are over 70 million formerly incarcerated people in America, and Richard saw an opportunity to help them find work.

Richard’s story shows what’s possible when someone takes full responsibility for their actions but refuses to let that define their future. He paid back every victim when he didn’t have to. He chose not to cooperate when it would have reduced his sentence. He started over from scratch in his 50s and built something meaningful.

Today, Richard continues working in the reentry space and shows up regularly for the White Collar Support Group, helping others navigate the criminal justice system. Sometimes the guys with badges and windbreakers do show up at your door. What matters is what you do after that knock.