Building a New Path: Rick Gray’s Journey from Incarceration to Empowerment

Sometimes the American dream becomes the very thing that blinds us to what we already have—and for Bill Carlson, that blindness led him from a successful investment firm to a federal prison cell.

I’ve talked to hundreds of people on this show, but Bill’s story hit me differently. Here’s a guy who did everything “right”—built a thriving business, named it after his grandfather, lived in an affluent neighborhood, sent his kids to private schools. He was living the American dream until it all came crashing down.

When Success Creates Blind Spots

Bill started as a stockbroker in 1986, making 200 cold calls a day from photocopied pages of Scottsdale phone books. The rejection taught him resilience, but success taught him something more dangerous. By 2004, he’d established his own investment firm, and everything looked perfect from the outside.

But as Bill told me, “The allure of recognition and material possessions clouded the true essence of my achievements.” When a business opportunity came along that he was confident would pay off, he made a decision that would change everything—he took money from a client account, planning to pay it back when the venture succeeded.

The business failed. He put in more money. It failed again. And instead of having the courage to tell his family they needed to change their lifestyle, he kept digging deeper.

The Call That Changed Everything

In February 2017, Bill’s world collapsed. His kids were away in college when he called them both from a grocery store parking lot during a snowstorm. “I said, you know, here’s what I’ve been doing, taking money from client accounts. I’ve been denied, I’m mostly in prison. My son swarmed me and hung up. My daughter just started crying and hung up.”

The next day, his daughter sent a text that would haunt him: “Dad, what the hell were you thinking?”

That question became the catalyst for everything that followed. The FBI approached him in a parking lot two weeks later, and Bill made the decision to cooperate fully. No attorney at first—he thought cooperation would lead to leniency. He was sentenced to 55 months in federal prison.

Finding Gratitude Behind Bars

At FCI Duluth, Bill discovered something unexpected. With nothing but a bunk, a locker, and a plastic chair, he started keeping a gratitude journal. Three things every day that he was grateful for, even if one of them was just that the weather looked nice.

“I was happier having less in that locker than when I had all the stuff I could have,” Bill reflected. “That’s when it really dawned on me—happiness wasn’t coming from things. It was coming from within.”

Bill threw himself into teaching GED classes for 16 months, working with guys mostly from Chicago’s west and south sides—people he never would have met in his previous life. When a student who’d been trying for years finally passed, watching him send that diploma to his mother or daughter became some of the most rewarding work of Bill’s life.

Building Something Better

Today, Bill channels his experience into speaking at universities like Clemson, University of Chicago, and Yale. But his approach is different from typical ethics training. Instead of just telling people what not to do, he focuses on the why—understanding the internal pressures and blind spots that lead to poor decisions.

He developed a course called “Better or Better: Finding Happiness and Gratitude in Prison and Beyond.” The insight that emerged surprised him: “Regardless of what got you there, what got you there was what you need, right? Many of us were trying or doing what we’re doing, looking for that happiness outside of us.”

Bill uses the metaphor of chasing butterflies—the harder you chase happiness, the more it eludes you. But sit still, be present, and it might just land on you.

His journey from the American dream to federal prison to finding purpose in helping others proves that sometimes our greatest failures become the foundation for our most meaningful work. Bill’s breakdown became his breakthrough, and now he’s using every bit of that hard-earned wisdom to help others avoid the same mistakes.