EPISODE 220
Scaling to $2.5B Without Industry Experience
with Brendan Keegan
What if the key to scaling a business isn’t knowing the industry inside and out–but knowing how to fix what’s broken?
Brendan P. Keegan is a six-time CEO, two-time bestselling author, and founder of bFEARLESS Ventures. He’s raised over $10 billion in capital, led six companies to exit, and grew Merchants Fleet from $500 million to $2.5 billion–without ever working in fleet management before. Now retired at 55, Brendan spends his time investing in bold ideas and living out his mission to build one million fearless leaders.
The Power of Curiosity and Problem-Solving
You don’t need to be the expert in the room, but you do need to be the one who asks better questions. Brendan shares why curiosity, not credentials, became the throughline of his career. From turning around struggling startups to transforming a 55-year-old legacy business, he explains how to spot broken systems, challenge assumptions, and lead a team through massive growth–even when you’re the new kid in the industry.
Why Fear Holds You Back (And What to Do About It)
Think fear isn’t shaping your decisions? Think again. Brendan calls it the FUD factor–fear, uncertainty, and doubt–and says it quietly shapes how most people show up at work and in life. In this episode, he breaks down how to build fear-resilient leadership: how to stop waiting until you’re “ready,” how to make decisions without all the answers, and why the best leaders move fast, stay coachable, and push others forward along the way.
Enjoy this episode with Brendan P. Keegan…
Soundbytes
18:56 – 19:48
“Our number one thing we hired was intellectual curiosity. Across the board. Period…As many skills as you think you have, you don’t. Your first job, you don’t know how to do 20% of it, 25% of it. But do you work hard? Are you a fast learner? Those are the things that are going to matter, you know. When you lose, are you coachable? In entry-level positions, I’m 100% attributes, nothing on skills or experience.”
11:48 – 12:35
“Can I just ask you a question? What did I do to get put in the penalty box? Why?” He goes, “What do you mean?” I said, “I got this other thing up and running. It was going great. I was killing it, and you moved me over here.” He goes, “Because it was broken.” And I said, “But why did you do that to me?”
To which he replies, “You’re great at fixing things.”
I didn’t see that when I looked in the mirror, but that mentor telling me, “You’re great at fixing things. Brendan, you take your technology engineering mind and you think, what’s the problem? So many people just jump in and start fixing things without thinking about the process. You’re really good at fixing things. I challenge you to spend the rest of your career not in a given industry, but focused on fixing and transforming things.”
42:33 – 43:03
“Have the courage to fail and the faith to succeed. Have the courage to say, ‘I’m going to go try out for that team, and I might not make it, and that’s okay.’ But then–have the faith: ‘I am going to show up in the best shape of every single person trying out for that team. I might not have the best basketball skills, but I’m going to be the best-conditioned athlete. I’m going to be so conditioned that the coach takes me and thinks he can teach me basketball.’”
Quotes
“Have the courage to fail. Be willing to do things you don’t think you can do, but also have the faith that you’re going to succeed.”
“Go take the mic. Go be the one in front.”
“If you don’t have a mentor, you’re short-changing your career. You will not go as far in your career. Mentors help you. They enlighten you.”
Links mentioned in this episode:
Connect with our Guest
Website: https://brendanpkeegan.com/
Connect with Brendan Keegan on LinkedIn: https://www.linkedin.com/in/brendanpkeegan/
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