He Risked $50,000 at 21… Then Faced the Hardest Fight of His Life

After Losing Everything in Subprime Mortgages… He Built an Oil Company

He was making millions in subprime mortgages—until the 2008 financial crisis wiped out his entire industry. In this episode of Backseat Ballers, Steve Blackwell, co-founder of Invito Energy Partners, breaks down what it was like to lose his career at 36, go years with no income, and rebuild from scratch in oil and gas. From running massive teams in finance to starting over with no clear path, this is a real look at what happens when everything you built disappears—and what it takes to come back.

He Quit His Job at 45 to Bet on Himself

Dewayne spent over 20 years working in the insurance industry before making a decision many people never do: leaving the security of a steady job at 45 to bet on himself and become a business owner. In this episode of Backseat Ballers, we talk about what it really takes to walk away from stability, build something from the ground up, and navigate the challenges that come with entrepreneurship later in life. This conversation goes far beyond business. Dewayne shares his story of growing up in Arkansas, losing his father at 15, serving in the Marine Corps, and eventually building a career in insurance before deciding to take the leap into entrepreneurship. We also talk about the realities of starting and scaling a business, the mindset shift required to leave W2 life, navigating racism in both corporate America and business, and why relationships and networking became critical to his success. If you’ve ever thought about leaving your job, starting a business, or betting on yourself later in life, this episode is an honest look at what that journey really looks like.

He Risked $50,000 at 21… Then Faced the Hardest Fight of His Life

At 21 years old, he borrowed $37,500 and put $12,500 down to break into the high-stakes world of commodities trading. Inside the 1980s Kansas City wheat pits, one mistake could cost you everything. He didn’t just survive — he rose to Chairman of the Exchange. hen life hit harder than the markets ever could. After surviving kidney cancer, he lost his wife to H1N1 at just 36 years old — leaving him to raise two young kids alone. What followed wasn’t about money. It was about responsibility, discipline, and becoming both dad and mom overnight. This is a story about risk, resilience, fatherhood, and what real strength actually looks like.

Sentenced to Life in a Mexican Prison… Then Everything Changed

He thought he was doing the right thing — until he was arrested in Mexico, threatened at gunpoint, and thrown into a federal prison with no trial and a life sentence. In this episode of Backseat Ballers, Rocky Malloy tells a story that sounds fake but isn’t: Mexican authorities, brutal prison conditions, torture he witnessed firsthand, and the moment he believed he was about to die. What happened next changed the course of his life forever. This conversation goes far beyond prison. It’s about fearlessness, faith under pressure, walking away from everything you know, and what it means to live with urgency when you’ve stared death in the face. If you’re into raw true stories, hard conversations, and people who’ve actually lived on the edge — this one will stay with you.

The Hardest Thing He Ever Faced — Loss, Purpose & Starting Over | Michael Bone

Mike Bone has lived through the kind of loss no parent should ever experience — and it changed everything. In this episode, Elliot sits down with Mike to talk about the hardest moment of his life, how he rebuilt his marriage, his purpose, and his career, and what he learned about resilience, discipline, and meaning along the way. Today, Mike runs two successful dog-training businesses in Kansas City. But behind the success is a story of grief, grit, faith, and choosing to build something that matters. This conversation is raw, real, and human. It’s not just about business — it’s about life.