"How to Lose" with Author and Entrepreneur Reggie Prevail
went into this conversation thinking we were going to talk about success.
Instead, I got punched in the gut.
I sat down with Reggie Prevail—a 30-year-old entrepreneur, investor, and builder—and what he laid out forced me to confront something I didn’t want to admit: I had been moving too fast, doing too much, and in some areas… pretending.
Pretending I wasn’t afraid.
Pretending I had it all handled.
Pretending I didn’t need to slow down.
And the truth is, that pretending comes with a cost.
We don’t talk enough about losing—especially as Black men. We’re taught to win, to dominate, to push through. But nobody teaches us how to lose the right things: ego, fear, perfectionism, control, and even people.
Reggie flipped the script for me.
He said, “Win or win.”
Not win or lose—win or win.
Because if you know how to use your losses, you never actually lose.
That hit me.
It made me think about my own life—my health scares, my relationships, my work. The moments where I avoided the truth because I didn’t want to face what might come with it. The times I held onto people longer than I should have. The times I tried to do everything myself instead of building the team that would actually help me scale.
That’s not strength.
That’s fear dressed up as control.
And here’s what I know now:
The revolution for many of us isn’t about doing more.
It’s about letting go of the things that are quietly holding us back.
Letting go of the ego that keeps us out of rooms.
Letting go of the fear that keeps us from the doctor’s office.
Letting go of the mindset that says we have to figure it all out alone.
And maybe the hardest one…
Letting go of the people and versions of ourselves that no longer serve where we’re going.
Reggie also broke down something that most people aren’t paying attention to: while everyone is chasing tech and AI, real wealth is quietly shifting into places we’ve overlooked—blue-collar businesses, ownership, systems, and control.
That’s a different kind of game.
And most folks aren’t even on the field.
So here’s the question I’m sitting with—and I want you to sit with it too:
What do you need to lose… so you can finally win?
Because if you don’t answer that honestly, you’ll keep building a life that looks successful on the outside—but feels incomplete on the inside.
And I’m not interested in that kind of success anymore.
I’m interested in building a life that’s real, aligned, and fully mine.
That’s my revolution.