For DJ Flores, 2020 was the year when everything he had built collapsed. After twenty-plus years in sales and logistics, he finally launched his own freight brokerage. Business was booming—until COVID shut down his clients overnight. The contracts disappeared. His savings evaporated. His dream dissolved.

“I lost the business, the house, and nearly the will to keep going,” DJ remembers. “But that’s where God met me.”

It was in that valley that DJ discovered the truth of Romans 8:28—God really does work all things together for good.

Failing Forward

Out of failure came clarity. DJ realized that chasing money and titles had left him spiritually empty.

“At forty, I finally admitted I didn’t even care about the stuff I’d been chasing. I just wanted to give—so I asked, What do I actually have to give?”

He began sharing what he knew. He started a Facebook group, giving away his sales scripts and templates for free to help struggling brokers. That small act of generosity grew into a 30,000-member community—and opened the door to a new life.

Divine Connections

One of those connections came through a cold LinkedIn message from John Hewitt, the founder of Jackson Hewitt and Liberty Tax.
DJ almost deleted it, assuming it was spam. Instead, that message led to a Zoom call, a new job, and a move for his family from Cleveland to Virginia Beach.

“God was positioning me,” DJ says. “Even when I thought I’d lost everything, He was setting the next step.”

That next step included serving as president of a national franchise brand under Hewitt’s Loyalty Brands group and launching his own show, The Robinhood Capitalists podcast, to spotlight purpose-driven entrepreneurs.

From Religion to Relationship

DJ’s journey wasn’t only professional—it was deeply spiritual.
Raised Catholic, he spent years bouncing between churches and even left faith altogether for a time. “I looked up to people instead of Jesus,” he admits. “And when people failed, I walked away.”

What finally brought him home was the realization that Jesus—not religion—is the true mentor.
When Hewitt publicly answered, “Jesus Christ” after being asked who his business mentor was, DJ knew God was confirming what he had been hearing all along: follow Jesus first.

The Hope Dealer

Out of pain and redemption came a new identity.

“I think God’s called me to be a Hope Dealer,” DJ laughs. “Everything I post or share is just giving away hope that He gave me.”

Through his content on LinkedIn and upcoming podcast projects, DJ encourages others who feel lost in transition.

“Don’t be afraid of failure,” he says. “Every failure holds either a blessing or a lesson—and both are from God.”

Faith, Family & Resilience

This year DJ and his wife Jenny celebrate 25 years of marriage—proof that perseverance and grace can outlast any storm. Together they’re raising five children and three grandchildren, walking out a testimony of restoration one step at a time.

“You’re never actually lost when you follow Jesus,” DJ says. “You may not know where you’re going, but your Shepherd does.”

Learn More

Podcast: The Robinhood Capitalists
Connect: DJ Flores on LinkedIn

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