Learn These Money Moves From The Investor That Went From Prison to Wall Street

Leon Howard taught himself the fundamentals of stock trading, and eventually used what he learned to build a life for himself post-release.
Credit: Leon Howard
By Jasmine Browley · January 17, 2022

“Y’all playing the wrong game.”

Leon Howard was only 16 when he was sentenced to prison for 10 years and heard this from his cellmate. Words that he says changed his life forever. 

For anyone else, a 10-year prison stint in your teens would be devastating but ironically, that wasn’t the darkest moment Howard had experienced up to that point in his life. 

He’d never met his father, Howard’s mother was incarcerated for substance abuse, and his grandmother passed away shortly afterwards. This chain of events left the New Orleans native homeless and with few options for survival. It didn’t take long before Howard found himself in serious trouble with the law– but he says it was one of the most transformative things that could happen to him. “My former cellmate changed my entire perspective on life, ” Howard shared with Essence. “After I  told him how much time I had in prison, he told me his sentence  was only 18 months.” 

Shocked, Howard realized his murder-related charge would take his entire childhood away, while his cell mate, hit with a major racketeering charge, would serve less than only two years. “He said he stole $2.8 million, paid $800,000 in restitution and kept $1 million for himself–y’all playing the wrong game.’ ” 

Howard said that resonated with him because as his former cellmate pointed out, Howard was playing Russian Roulette with his life. “He made me realize that me and a lot of my peers were willing to die or go to jail for something that wouldn’t make us any richer or better off in life, “ he said. “We didn’t have anything to show for our crimes.” 

This realization sparked his interest in building financial literacy, and really learning how money flows in in the US. “This country is nothing but a business and no matter what, we all know the higher ups aren’t going to let this business go under,” he shared. 

Through the course of his sentence, Howard said he devoured any information he could about wealth-building. “My cellmate said rich people put their money into three places: the stock market, a business and then real estate,” Howard said. 

Following that template, Howard taught himself the fundamentals of stock trading, and eventually used what he learned to build a life for himself post-release. 

Now 39, the CEO, investor and renowned speaker has built an empire teaching people what he learned. Known as the Wall Street Trapper, he likens the US business structure to the hustlers in his old neighborhood. 

“Fundamentally, the drug dealers in the streets and the CEOs at fortune 500 companies are no different from one another,” he shared. “Once I acknowledged that, I was able to really apply what I was reading about in the markets.” 

He says he hopes the Black community leans into investing instead of other long-held theories about money. “For the longest, we’ve been taught to give our time for money, put it in a savings account and just let it sit,” he said. “That’s not going to build generational wealth.” 

He also pointed out that although investing is starting to be more widely accepted among us, Black women in particular should feel more empowered to invest more aggressively.  “Most men I know hand over their paycheck to the women in their lives so they can manage it, because they are more than capable of running a household–but what I’d like to see more of is them taking some of that money and making it work for them. Start with ETFs (Exchange-traded funds) and look at what makes most sense for your next move.Let’s turn our last names into an asset.”