Damon Bedell doesn’t do chest thumping. He doesn’t give motivational speeches. He doesn’t talk much at all, unless you ask the right question.
“I don’t really talk about myself,” he said early in our Zoom call, arms crossed, eyes sharp beneath the brim of a ballcap. “I just do.”
But “just doing” has somehow turned him into the guy who rebuilt a failing title company during a recession, launched an underwriter in the middle of a global pandemic, and built an empire with nearly 200 employees. He doesn’t chase headlines. He chases problems. Fixes them. Grows them. Then quietly moves on to the next big thing.
He’s not loud. But his track record screams.
The son of a relentless, self-employed father in Oklahoma, Damon was raised with grit in his DNA. His dad ran a commercial mowing business. Think tractors, steep banks, and no excuses. Damon learned early how to work, how to sweat, and how to handle machinery and chaos with equal calm. That discipline shaped him. That hunger for more drove him.
After college, he went into insurance, building a Farmers agency from scratch. It paid off with big premiums, a steady book. But Damon doesn’t coast. He started tinkering with side hustles: a pizza joint (money pit), a limo bus business (money printer, plus a few wild nights). They were distractions, sure, but they were also experiments. And when the right opportunity came knocking, he was ready to go all in.
That came in 2009, when he found Apex Title: a title company so busted, it was practically radioactive. No sane person would’ve touched it. Damon bought in.
The name was toxic. Clients were gone. Debt was everywhere. But Damon doesn’t scare easily. He didn’t throw donuts at realtors like the other guys. He treated it like his insurance business: relationships, value, data. He built trust from scratch, sometimes deal by deal, handshake by handshake. He hired hungry people from outside the title world. Trained them his way. It took three years to claw Apex back from the edge.
And then? He scaled it.
By 2015, he had married Lindsay, started building a family, and Apex was also rapidly evolving. The company was strategically branching out, transforming into a dynamic network of successful enterprises that extended its reach across diverse markets. And as Damon locked in, he made Apex a machine. Efficient. Loyal. Fast.
But that itch? It never left. He bought into music venues. He took on real estate deals and even bought a 16-room motel, Arthur Murray’s Motel in Noel, Missouri (think Schitt's Creek). They pulled his focus. “Every time I step out, it’s a pain in the ass,” he laughs. So he came back to center. Back to Apex.
Then COVID hit.
Rates collapsed. Markets panicked. Someone told Damon, “You can’t start your own underwriter right now.” That’s when it happened. The phrase. The mindset. The brand:
“Hold my beer!”
He did it anyway.
In April, 2020, he launched Oklahoma’s third domiciled underwriter, while the world was shut down. He tied up millions in reserves, with no guarantee it would work. He relied on data, loss ratios, claims experience, and guts. For four years, he pushed. In 2024, the underwriter earned an A rating from Demotech.
He didn’t stop to celebrate. He was already moving.
Today, Damon’s operation is nearly 200 people strong, with twenty-plus brands under the Apex umbrella. But he still thinks small—in the best way. “At first I just wanted an extra 10 grand a month,” he shrugs. But Instead, he built a machine. And now he’s trimming closing times and obsessing over every inefficiency.
He’s still the same guy—at the gym early, at the baseball field for his sons, back home with Lindsay, back in the office chasing the next challenge. North Carolina. Colorado. Joint ventures. New markets. New targets. The tension doesn’t rattle him. He lives in it. He thrives in it.
He doesn’t lead from the stage. He leads by example. He doesn’t yell. He moves. He builds. He fixes.
“Hold my beer” isn’t just a throwaway line. It’s a dare. A philosophy. A declaration.
Because when Damon says it, he’s not being cute. He’s telling you that the next impossible thing? He’s already halfway done.
And if you’re lucky enough to be on his team, you know the truth: he’s not just proving people wrong. He’s proving what’s possible.