Roy Castro has a unique and inspiring story. By the time Roy was in his early 20’s, his first exposure to a job came in the drug business. His father had left the scene when he was an infant, and his mother was an addict. Roy’s story is a fascinating one, in which he went from federal prison to CEO of NYC’s largest ice cream distributor.
the second part os his joourney starts when he came to the doorstep of STRIVE in 2003 after serving nearly a decade in federal prison on a drug charge.
His first job in the neighborhood on the outside was cleaning out freezers and equipment at Edy’s Ice Cream, and he was quickly promoted to manager. From there, he continued learning and growing and doing all the things people strive for—owning a home, starting a family, and looking to make things better for them.
In 2013, Roy bought his own Ice Cream distributor, which now employs 15 people and generates over $6M in business. As a graduate of Goldman Sachs 10,000 Small Business Program, Roy is now leading New York’s largest ice cream sub-distributor
For Roy Castro, life wasn’t always sweet. His father left the family when Castro was a baby. He spent his youth getting in trouble, dropping out of high school, and landed in federal prison on a drug charge when he was 20. There, he liked to hang out with the white-collar prisoners, he was Intrigued watching them tune in to see the stock news on TV and reading the financial papers.
He had his sister send him Stock Investing for Dummies and a book of the 400 most-used business words. While in prison, he earned his GED and helped others get theirs. Most important, he decided: “Enough already. I don’t want to sell drugs.”
Ralphy Dominguez goes from the South Bronx-to-Prison-to-an-Entrepreneur
With help from workforce organization Strive, Castro began working three jobs after his 2002 release, including one at Edy’s Ice Cream, where he cleaned out freezers. Eventually, he became a manager, handling Edy’s sub distributors. Soon he was able to purchase a house, and in 2013 he jumped at an opportunity to buy into D.M. in Long Island City, taking out a $350,000 home-equity loan.
As he was running his business, Castro was still frustrated by what he didn’t know about managing a business, He took out a business a card he’d tucked in his wallet years ago at a Strive event and called the person that had given it to him, within weeks he was in a classroom at LaGuardia Community College with 30 other business owners in the investment firm’s 10,000 Small Businesses program. He learned how to better manage his balance sheet, margins and profit and master analytic tools.
D.M.’s revenue was $7.5 million in 2016. To help bodega customers compete with national chains like 7-Eleven, he’s added frozen items such as pizzas to his line.
“I’m always looking for ways to grow the business,” he said. Every day he maps out the strategy for his 15 employees and 10 trucks. “Last week my target was stores with high margins where we are only selling a little bit of product,” he said. “This week we’re concentrating on getting more product to them.”
Castro faced a major life obstacle, but having the right mindset empowered him to leverage it to his advantage. He used his setback to set up his future.
“I’ve taken so much from life in my youth. I was a taker. So now it’s all about giving. So how do I give back? How do I make that impact?” Castro said. “I wanna sit with a 16-year-old Roy Castro and say, ‘There’s another way. You just don’t know it, but let me show it to you.’ How do I stop being a taker and being a giver, and that’s why I do what I do.”
“Before, I sell a drug to somebody and it brings harm and destruction into somebody’s life, into their home,” he said. “Today, I’m selling ice cream that they bring joy into every household. I’m selling happiness. That’s what I sell, one scoop at a time. One scoop at a time I’m gonna bring happiness into your life.” -Said Castro
After years of volunteering and supporting STRIVE’s mission, Castro joined the organization’s Board of Directors in 2017. His firsthand experience as a STRIVE graduate has allowed him to bring a valuable perspective to the organization, helping shape programs and strategies designed to create meaningful opportunities for people who have historically faced significant barriers to employment.
In 2021, Castro was elected Board Co-Chair alongside Brian Friedman, President of Jefferies Financial Group. His leadership and commitment to the organization have made him an important voice in STRIVE’s efforts to expand economic opportunity and help individuals build more secure and independent futures.
Castro’s work has also earned him recognition beyond STRIVE. In 2019, he was honored at the Robin Hood Heroes Breakfast, recognizing his commitment to giving back and creating opportunities for others. He is also a graduate of Goldman Sachs’ 10,000 Small Businesses program. He was nominated for the program by former Goldman Sachs Partner Dina Powell McCormick, whom he met through his involvement with STRIVE.
Today, Castro continues to combine entrepreneurship, investment, philanthropy, and advocacy. Much of his work is focused on creating pathways to opportunity for people who have been overlooked or marginalized, with a particular commitment to supporting individuals impacted by the criminal justice system. His own journey has become a powerful example of how second chances, education, mentorship, and economic opportunity can change the direction of a person’s life.
About STRIVE
For four decades, STRIVE has worked to help people overcome some of the biggest obstacles standing between them and meaningful employment. The national workforce development organization provides career training, employment support, and other services designed to help individuals develop the skills and confidence needed to build sustainable careers.
Based in East Harlem, New York, STRIVE operates in 14 locations across the country and has served more than 85,000 people. Its programs support adults at different stages of life, including individuals who have been involved with the criminal justice system.
At the heart of STRIVE’s mission is the belief that employment can be a powerful pathway to greater financial stability and independence. By connecting participants with skills, career opportunities, and support systems, STRIVE helps people move beyond barriers and toward long-term economic mobility.
