Justice Impacted: Rick Gray’s Journey from the Streets to Empowerment

When Jay Jordan knocked on my wall from solitary confinement and asked who I was, I couldn’t answer that question. That moment sparked everything that followed, a transformation from someone facing life under three strikes to building a hundred-machine vending empire and changing laws for millions.

The Business Plan Born in Solitary

Jay spent two years in the SHU (segregated housing unit) with two strikes already on his record, potentially facing life if he got a third. But instead of breaking down, he started building up. His mother sent him “reams and reams and reams information” from the internet, and Jay became what he calls “this academic researcher”, devouring everything about history, politics, business plans, even giving stock tips to other inmates.

“I had an appetite for knowledge and that appetite was literally locked up for years and years and years,” Jay told me. “I realized that it was to weight off my shoulders and I became like this academic researcher, you know, I just wanted to know everything.”

He created a detailed plan for his release: sell real estate during the housing crisis, sell life insurance to people in Stockton who kept dying without coverage, flip used cars, and run it all out of a barbershop where he’d cut hair. Jay even started a vending machine company while still locked up, calling his sister from prison phones to coordinate buying machines from a guy named Leo.

“I call Leo and, you know, on freeway. I had like 30 to 45 seconds before. This is a collect call,” Jay explained. “I’m like, hey, Leo, this is Jay. I’m on a boat ride. I wanted you to hear my voice. I want to buy your machine. My sister’s going to take it from here. Really appreciate you.”

The Gut Punch Reality

Jay got out January 19, 2012, and went straight to the barbershop before even going home. That’s when Big Hurt delivered the first blow: “You can’t get your cosmetology license.” Then Jay got online and searched for his backup plans. Insurance license with a felony? No. Real estate license? No. Used car dealer? No.

“Second day I was up. None of it was true,” Jay said. “So what do I do? I said, okay, you know, it’s better. They’re the thing that then go for the one bird in the hand instead of two of the books, right? And the one bird I had in my hand was my vending machine.”

Jay pivoted hard. He went to his sister’s CrossFit gym and noticed people paying five dollars for coconut water that cost two dollars wholesale. The profit margins were “insane.” He convinced the gym owner to let him place a machine, then started scaling across California’s booming CrossFit scene.

Building an Empire from Four Machines to 102

Jay’s approach was brilliant: get the contracts first, then find business partners to fund the machines. “I started getting contract left and right, up and down the state of California. And it became, we scaled from four machines to 102, like eight months.”

But he wasn’t just running vending machines. His parole officer didn’t consider the business “real,” so Jay worked swing shift at a Trader Joe’s warehouse from 4 PM to 2 AM, then woke up at 6 AM to work out and service his machines. He was simultaneously taking an alcohol and substance abuse counseling course (which he quit) and doing community work through a program called Beyond Incarceration.

The vending business was working. Leo had taught him the exit strategy: build your route, then sell it for double the annual revenue. With a hundred machines generating serious cash flow, Jay was looking at a major payday.

From Grape Soda to Changing Lives

Then Jay’s friend Sonny’s brother was shot four times in the head and killed. Jay looked at his nephew, who was afraid to go to the park because of violence in Stockton. “I said, okay, I got to do something. I can’t have my legacy being ice cold, grape soda for 50 cents,” Jay decided.

He called his business partner and sold out of the vending company. “For those who know me, when I put my mind to something, they’re going to stop it,” Jay said. “And he bought me out and I started network mentoring.”

Jay founded First 50, a youth mentoring program that taught civic education through hands-on experience. Kids learned about automotive repair by changing tires, then went to shops to do it. They studied elder care, then visited nursing homes. They learned about city budgets and utilities, knowledge most adults don’t have.

Every Single Kid Went to College

The program started with 70 kids and narrowed to 30 hardcore participants who showed up every Thursday and Friday at Jay’s dad’s church (the school board banned him from the high school because of his felony). The group included kids with GPAs below 1.0 and others with 4.0s, Black, Latino, Asian kids from across Stockton.

Jay spent every dollar he had on those kids, including his last $100 on graduation gifts. “My last. I was overdraft after that,” he admitted. But the results spoke louder than his empty bank account: every single kid graduated and went to college.

“They became my family,” Jay said. The kids put their handprints on his dad’s S10 pickup truck, which got covered in paint from their community beautification projects. “And none of that mattered because they were experiencing joy and Stockton in a way that they had before.”

Jay’s three years of funding from his dad were running out, and he was broke. But his community work had caught the attention of Congressman Jerry McNerney, who hired him as field director for his re-election campaign. Jay became probably the first person on parole to run a Congressional field campaign, and they won by the largest margin ever.

But when Jay finished parole in January 2015, the final gut punch came. The city of Stockton, despite praising his work publicly, told him it would be “too politically difficult” to hire him. Once again, the system said he was good enough to work alongside them but not good enough to work for them.

That rejection pushed Jay toward the work he does now, co-founding Time Done and serving as CEO of Alliance for Safety and Justice, where he’s passed over a hundred new laws in ten years. Sometimes the biggest setbacks become the setup for the most important work. Jay proved that the nightmare doesn’t define you, what you build after it does.