The man who went from prison to CEO: The inspiring story of Roy Castro

Roy Castro. Photo courtesy of STRIVE.

It’s a freezing January, and Roy Castro is hosing down ice cream trucks. It can’t be pleasant. But, it was actually something of a miracle.

Just a year before in 2002, Castro walked out of prison. He was 27 years old. In prison for 15 years off and on since age 16, this time he vowed not to go back to drug dealing. That was harder than he thought.

Living with his aunt, he spent a year looking for a job. Fifty interviews later, a felon like Castro figured he was never going to get a job. He hooked up with old drug connections. Time to do what he could to support himself.

That very day, a neighbor told him about STRIVE, a program that they said could help him get a job. He reluctantly showed up and his life began to change.

STRIVE’s tough love speakers hit the audience hard on the ideas and behaviors that kept them out of the mainstream. The approach worked for Castro. The program helped attendees get a job, but more importantly taught them to keep a job. He learned how to dress and be on time. He learned humility. Teamwork. How to work in an organization.

STRIVE got him his first job and he hosed down those ice cream trucks for years while he planned how to move up. It took 10 years to climb the ranks, but he did. He followed his plan of saying yes to challenge. He took advantage of small opportunities to make them big.

By 2012 he had a $3 million ice cream delivery business and he was panicked. He didn’t know how to grow or even keep his business: Taxes, finances. He knew nothing of these things.

Once again he called on STRIVE. On the eve of Thanksgiving, he sent an email to Goldman Sachs executive Dina Powell McCormick whose card he had carried around for six years. It just so happened McCormick was in her office that late hour before the holiday. She remembered him. She immediately emailed him and pulled strings to get him a place in the company’s Ten Thousand Small Businesses educational program.

Once there, Castro saw he was over his head. So many business people with lots of experience. Then, he saw McCormick. He vowed not to let her down. He would work harder than anyone in the room. Triple hard.

The next year Castro graduated number 1 in the class. Legendary investor Warren Buffet handed him his diploma.

Using the knowledge he gained, he grew his business to $10 million a year.

An extraordinary life: A boy who at age 11 was homeless with his drug addicted mother, who went to prison at 16, became a man who made his way, overcoming all obstacles.

Roy Castro’s rules and secrets to success

From a life as a 13-year-old living on the streets to a young life in prison to the CEO of a $10 million company.

Roy Castro started at the bottom and these are his rules for getting ahead:

1 – Tame your ego. Be prepared to admit when you are wrong. Be humble.

2 – Say Yes when others say No. When you hear others refusing a task, take the task.

3 – Ask for the crumbs. A small opportunity is a chance to create big opportunities.

4 – Make the sacrifice. Work as hard as you can even at simple tasks. Save money. Show up on time.

5 – Separate from the pack. Don’t be one of grumblers.

6 – Speak your truth. Admit what you don’t know. Ask for help.