Prison Guard Becomes Trader

A story about Ken Rideout's journey from working as a prison guard to becoming successful on Wall Street.

"I started at the prison when I was 1 week out of high school. Being in a men's maximum security prison at 18, I probably looked like I was 15. Prison is very segregated, but I knew most of the white guys because I grew up in that sphere. The difference between guards and inmates is the inmates have been caught - the guards are just as bad. It was the worst experience of my life, just the thought of having to do that every day for 20 years.

I moved to New York after college. I had a pharmaceutical sales job making $36,000, but my rent and student loans were more than my take-home pay. I was playing pickup hockey at Chelsea Piers when a French Canadian kid asked if I wanted a job as a trading assistant, brokering electricity trades.

The trading desk in the late 90s was like a locker room - very alpha-driven with lots of hazing. I was boxing for the New York Athletic Club at the time, and one day when they were hazing me, I slapped a guy across the face. They fired me, but the guys at Enron who I was covering told their senior traders what happened. A senior trader called me up with a job offer - doubled my salary to $80,000. I didn't even know we had competitors, that's how naive I was. I was only there for 2 months and barely knew what a bid and offer was. The guys at Enron became good customers and literally changed my life."