I Was Making Millionaires Before I Could Afford My Own Rent.

"Is Legend really your first name?" is almost always the first question I get. And yes, yes it is. My parents gave me a name with high expectations. Really, though, they just wanted something unique, and honestly, I'm proud of it.

The second question, especially in business, is always: "How did you get into selling businesses for a living?" Those two questions actually connect, because the answer is that I went to work for my pops when shit hit the fan.

That's usually where people's eyebrows go up. "Oh, must've been nice." I get it. There's a stigma attached to working with your dad. It implies you didn't earn it. But trust me, it wasn't the silver-spoon situation people picture. There was no salary, no draw, no 401(k) match, no hourly, no safety net. Just me, my dad's basement, a laptop, and a phone.

What my dad gave me was better than a paycheck. He gave me the opportunity to figure it out for myself, and he held me to a standard that forced me to earn it.

My first day, I asked him, "Alright, so... what do I do?" He said, "Pull up Google Maps, search for hospices, start calling them, and ask if they want to sell their business." That was it. No training manual. No onboarding. Just cold-calling complete strangers and asking if they wanted to sell their company. That's how I got into business brokering.

My dad wasn't some investment banker with a corner office. He was an entrepreneur who'd built things from scratch his whole life, and he taught me the way he was taught: by doing. He didn't hand me answers. He handed me the phone and said, "Go." Looking back, that was the greatest gift he could've given me, because I learned that opportunity is captured by action. I also saw the good and the bad of small businesses, both from the people I talked to and from the way my dad ran his (no offense, Pops). He always knew I didn't like how certain things were done, and that's part of why I started my own. I saw both the right and the wrong ways to get a deal done, and that's my edge.

I went to college, tried the traditional route, and couldn't make it click. Then COVID hit and blew everything up. So there I was, right before the world shut down, making cold calls in a basement, hearing "no" a hundred times a day. Okay, more like 40 or 50, my dad would know. Making no money, and learning this business the hardest way possible.

A friend of mine used to say, "The hungry dog runs faster." The people who got handed a seat at the table have never been late on a bill. They've never slept in their car or a storage unit to make it work. They've never watched their family lose everything and start over from nothing while living in their grandfather's basement, which is what I grew up with and saw. I watched my family fall apart over money struggles and more. That gave me a hunger, and an appreciation for this work, that you just can't fake.

Within my first two months of cold-calling, I found the owner of a company doing $6 million a year in profit. I found his name and number on an old page of his website he'd clearly forgotten to take down. I called it just to see if he'd answer. He picked up. There was no reason this guy should've signed with me, but I told him the truth: "I haven't done this at your level before, but I'll outwork anyone else you talk to." He said, "Alright, let's go." I know, it sounds absolutely crazy. And it was.

I went back to my dad and asked, "What do I do next?" He looked at me and said, "Figure it out." That was his way. Not because he didn't care, but because he knew the only way I'd actually learn was by doing (part of me also thinks he may not have known himself, since at that point he hadn't dealt with businesses that size either). And you wouldn't believe what happened next. I didn't end up selling that business. No surprise. But I spent months working with someone running a $36 million company, talking to real buyers at that level, learning firsthand what that world looks like. That taught me more than any textbook ever could, and it got me hooked. I knew right then this was what I was supposed to do. Even though I failed, hard, I saw the opportunity: if I could just learn the right process, this could be amazing.

I'm always honest with people; all my past clients will agree. I'd get on the phone, build a real conversation, and tell them exactly where I stood. "I'm going to be honest with you. I'm newer at this personally. But I'm going to work as hard as I can to get your business sold." People respected that. They'd started out somewhere too, not knowing much either. We'd build a genuine connection, and most of them said the same thing: "Alright, I'll give you a shot." I ended up signing clients I arguably had no business signing at the time.

The problem? I didn't know how to get deals across the finish line. I failed. A lot. More than ten deals where I got the client on board but just couldn't close. The infrastructure wasn't there. The process wasn't there. And I was learning the hardest possible way.

A year and a half in, I'd made about $20,000 total. No salary or hourly to fall back on. Little in savings. I came close to sleeping in my car while I figured out another apartment, stretching every dollar just to buy myself more time. I'm not saying that for dramatic effect. That was my actual reality.

Using the same tools I'd taught myself while finding business owners, I tracked down phone numbers and emails for every business broker and investment banker I could find. I called them, emailed them, and didn't stop until someone gave me a chance. I landed at a lower-middle-market firm that saw my potential and actually taught me how to close deals. That was the real turning point. I finally learned how to do this the right way: how to build processes, manage deals, and get them across the finish line.

That lowest point, broke and close to living out of my car, is also when I found my faith. I became a Christian at 25, and I'll just say this: everything changed after that. I'm not here to preach (to each their own), but it matters to me, and it's part of my story.

All those early failures are the reason it's so hard for me to fail now. I've made every mistake you can make in this business, and I built my entire playbook out of them. There's no chance I'm going back to where I started. I don't want my family to ever experience what I went through. That's what drives me every single day.

Today I've closed over $100 million in transactions across 45-plus deals. BridgeBook is what I'm building from the ground up: a marketplace and advisory platform for buying and selling businesses valued under $50 million across the United States. I'm the kind of broker who actually comes and meets you in person when I can, because I think that matters. I also partner with Empire Flippers as a Senior M&A Advisor, helping sell online and digital businesses. They operate worldwide, and when there are U.S.-focused deals that make sense, we work on those together.

I live in Charlotte, North Carolina, but I work with clients nationwide. My goal is to build a boutique team of people who care as much as I do about doing this the right way, and making the experience something business owners actually enjoy instead of dread. Because at the end of the day, this business is about people. Not just spreadsheets and multiples.

If you're thinking about buying or selling a business, we'd love to talk.