In May 2019, I was trying to line up my sixth-ever inspirational podcast interview, aiming to get high-profile guests to come on my show. Sure, it would have been easier to invite people I already knew, but I understood that to build the kind of network I envisioned—impossible as it may have seemed—I had to do things differently. Because if nothing changes, nothing will change.
A Billionaire’s Unexpected Yes
Then a friend suggested I interview his boss. His name was Michael Loeb. I didn’t know much about him at the time—only that he was wildly successful and having him on my show would be a big deal. And within minutes of being CC’d on the introduction email, Michael replied himself.
"Yes, I’d love to be on Dustin’s Life’s Tough, You Can Be Tougher podcast.”
No hoops to jump through. No resume check. No, “How big is your audience?” It was as if he knew—somehow—that I needed a win. When I told him we could record remotely, he surprised me again.
“Great. I’ll come to your studio and we’ll do it face-to-face.”
I had to clarify. “Wait… you live in New York City, and you’re going to drive all the way to a small neighborhood in Maryland just to visit me?”
“Yes,” he said, “and I’m really looking forward to meeting you.”
When Michael arrived for our interview, having spent hours in the car, paying toll after toll, I felt something I still struggle to put into words. He walked into the small studio I had rented—one that, in my eyes, was beautiful but surely beneath a man of his stature. But to him, it wasn’t. There was no arrogance, no posturing. Just a man willing to sit across from me and talk.
The Mindset of a Mastermind
For 90 minutes, I asked him everything—how he built his empire, the risks he took, the toughest person he ever knew. We even discussed some bad press he had recently faced, and in that moment, I realized that even a billionaire feels—and that heavy is the head that carries success at his level. And ultimately, I asked him why he was so eager to help people like me—people he owed absolutely nothing.
His answer was simple. “Because it feels good.”
This man had built billion-dollar businesses, advised some of the sharpest minds, and yet, what drove him was the desire to give back. Not for recognition. Not for leverage. Just because it felt good.
The Interview That Opened Doors
When the episode aired, it became my entry into the big leagues—something I couldn’t have known at the time. But I imagine Michael knew it all along. People support what they help create, as Michael bluntly puts it. Because of his introductions, I went on to interview Wyclef Jean, Daymond John, and many more.
Over the years, our friendship—both personally and professionally—has deepened. His nuggets of wisdom have led me to believe that the most ridiculous ideas are often the best ones. That an unexpected email introduction between two extraordinary people is one of the greatest investments you can make. That generosity isn’t always about money—it can be about access.
But beyond business, Michael is also a family man at heart. He invited me, my wife, and my kids into his home. And on May 30th, 2019, he invited me to speak at his CEO Summit—an exclusive gathering held at his home in the Hamptons, the very same home I had once seen on the hit TV show Billions. The platform and audience he provided me far exceeded the one I had given him. Here I was, standing in a room filled with visionary thinkers, builders, and rule-breakers—people who challenge everything you thought you knew.
And Michael had put me there.
The Power of Resourcefulness
He never gave me rules or a script—just a simple instruction: share your story. So, I did. I talked about what I had learned from my early days in foster care: when you lack resources, you have to be resourceful.
My biggest takeaway from that day? Creativity and grit are the real ingredients for success. Because success, after all, leaves clues. Some of the biggest companies of our generation were built by entrepreneurs without college degrees, and many ultra-successful people—like Michael—never received a large inheritance. Simply put, an Ivy League degree or being handed money won’t guarantee business success. What does increase your odds? Having the heart of a learner, not a knower.
Leaders Create More Leaders
By the end of that day, it hit me—why Michael had opened his home to hundreds of entrepreneurs. He knew that by surrounding them with people who could take them higher, they would do just that.
Leaders such as Michael don’t create followers, they create more leaders.
It’s easy to surround yourself with people who think like you, who validate your opinions, who make you comfortable. But growth doesn’t happen in comfort. If you want to reach Mars, you have to be willing to get uncomfortable. You have to seek out the minds that will challenge you, question you, and force you to level up.
But before you think he’s Mother Teresa, he’s not—and he’ll tell you that upfront. He won’t hand you the fish, but he will show you where to cast your line, and if you’re lost, he’ll make sure you find your way.
And now, for the first time, it feels like I can finally give him something—something he deserved long ago.
Welcome to the 2025 list of 40 Over 40, Michael Loeb.
One day, when scientists inevitably study his brain (because of course they will), they’ll find a clear roadmap to how he’s always seen the world.
Because to Michael “The Mastermind” Loeb, today isn’t just another Thursday.
It’s the day you can change your life forever.