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Home » Future of Work » A Conversation With Roy Castro: A STRIVE Success Story

For systemically marginalized populations, the societal barriers to a life-sustaining career can appear insurmountable. STRIVE, a workforce development nonprofit founded in East Harlem, New York, empowers individuals who are facing these barriers by providing equitable access to the training and support needed to gain quality employment and economic mobility.

Roy Castro, CEO of Castro Ventures, is the co-chair of STRIVE’s board and is himself a STRIVE graduate. He shared how STRIVE helped him change the course of his life more than 20 years ago after a decade in prison.

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Roy Castro

CEO, Castro Ventures; Board Co-Chair, STRIVE

What kinds of challenges do the individuals who come to STRIVE face?

Like me, most STRIVE students have come from communities plagued by the chronic, generational poverty that stems from decades of systemic racism. The majority are Black or Hispanic/Latino individuals with no higher education degree. Eighty-six percent are unemployed, 83% receive public assistance, and 45% have been involved with the justice system.

What brought you to STRIVE?

When I was in federal prison, I noticed the guys who were in for white collar crime were always following the stock market on the cable news. I didn’t understand the stock market ticker display that was being shown, but I did figure out that they were somehow making money as they sat in prison, so I paid attention and learned everything I could about stocks.

When I was released, I was intent on getting a job in the stock market, but I was informed that a person with a felony was not able to be employed there. That’s when my friend’s mother told me about STRIVE and made me promise to go so I could get ready for the workforce.

What did you learn from your experience with STRIVE?

STRIVE gave me the blueprint for the working world. They taught me how to dress and conduct myself in a professional environment, and I learned basic computer skills. Then they helped me get my first job.

I started out cleaning freezers for an ice cream company. From there, I studied the business and applied everything I learned at STRIVE until I bought my first route and became an entrepreneur. Now I’m in a position to hire STRIVE graduates myself.

STRIVE does more than help people get a job. STRIVE supports the whole person, providing help with finding housing, healthcare, financial support and other services.

How does STRIVE’s evidence-based pathway model work?

Over the years, STRIVE has developed a five-pillar model for success that includes career-readiness training, job-skills training, career coaching, job placement assistance, and lifetime support for grads. Services like referrals for secure housing, food, healthcare, and financial assistance help grads get stable in their lives so they can hold down that first job.

STRIVE also partners with local employers to ensure graduates walk away certified for jobs in top growing industries, like healthcare, construction, and logistics. This provides a pipeline of prepared talent ready to fuel the local economy.

Eighty percent of STRIVE students graduate from the program, 76% get placed in a job, and 70% retain their employment. STRIVE works! It’s a winning investment for everyone, and it changes lives.

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About Roy Castro

Roy Castro is Founder & CEO of Castro Ventures, Inc. and serves as Board Co-Chairman for STRIVE, a national nonprofit that provides career training and job placement services for people facing intersectional barriers to employment. Mr. Castro first joined the STRIVE Board of Directors in 2017 after many years of volunteerism. As a STRIVE graduate Mr. Castro provides invaluable insight and strategic guidance to the improvement of STRIVE’s programs. In 2021 he was elected to serve alongside President of Jefferies Financial Group Brian Friedman as STRIVE Board Co-Chair.  

In 2019 Mr. Castro was honored at the Robin Hood Heroes Breakfast. He is a graduate of Goldman Sachs’ 10,000 Small Businesses, having received a nomination for the program by former Goldman Sachs Partner Dina Powell McCormick after they were introduced at a STRIVE event. Mr. Castro first came to STRIVE in 2003 as a returned citizen upon his release from 10 years in federal prison.

Through his continued work with STRIVE and his array of investment ventures Mr. Castro frequently pays it forward serving as an advocate for the mobility and empowerment of the systemically disenfranchised–particularly the justice impacted.


STRIVE is a national workforce development leader that for 40 years has successfully provided services to populations facing significant societal barriers to employment. STRIVE moves students into careers that lead to upward mobility and economic empowerment. Headquartered in East Harlem, New York and with operations in 14 locations nationwide, STRIVE has helped more than 85,000 individuals through employment programs geared toward adults of all ages, including those with involvement in the justice system.

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