Alex Hines

I started at 18. The first one that worked was graphic tees in 2010. That grew into technical garment design and manufacturing, which is much harder than it sounds and taught me more than anything since.

In 2014 I lost a nationwide Nordstrom deal at a trade show in LA because I wasn’t paying attention to the thing in front of me. I had one main company and five or six side ideas going at any time. It felt like being a great entrepreneur. It wasn’t. It meant nothing ever got all of me.

I sold my first company in 2017, a bootstrapped SaaS for wholesalers. Small exit, but it was mine. The second was DealScreen.ai in 2025. Both times the papers were signed and the second-guessing hit harder than the money did.

Health challenges took the businesses I’d spent years building. I spent that year winding them down, and took a job as a bandsaw operator at a pallet plant to pay for it. Full time, on site, cutting wood.

I studied design at night on the days I had anything left, then went back to school full time in September for a 12-week intensive. I was 32 and starting over. The only thing 14 years of building had left me was knowing how to build.

That same year I started a foundation in honor of my best friend, helping people through mental health crises. It’s paused while I build this, which is a trade I think about more than I’d like to.

Sixteen months searching. Two letters of intent. Zero closes. A convenience store. A boat rental company. Anything that held still long enough.

It felt like progress. Tabs open, calls booked, always busy. I was browsing, and I couldn’t tell the difference between that and buying.

It turned when I stopped looking at businesses and started looking at myself. What did I already understand? Where could I add something instead of just owning it? The answer came back fast, and it was tree removal.

My stepdad Tim ran a tree removal business for 38 years. I grew up around it. That’s why it was the one thing on the list I understood without being taught.

It was profitable. It was sellable. When Tim was done there was no buyer and no plan. He locked the door and walked away, and 38 years of work stopped existing that afternoon.

Nobody bought it. Nobody knew it was available. I was out there looking for exactly that business and I couldn’t have found his if I tried.

510,000 US small and mid sized businesses exited the market in 2022. “What happened to those places?” Well, 92% of them turned off the lights and went home. Forever.

McKinsey puts the avoidable share of those closures at 6 to 13 percent, and says they end “not because the businesses lack value, but because pathways to succession are limited.” By 2035 another six million owners reach the same moment, and more than a million of those companies are worth buying.

Every one of those is somebody’s Tim. For a lot of them, the buyer existed.

A marketplace was never going to fix this. Listings only reach the owners who already decided to sell, already found a broker, already got written up. Almost nobody gets that far. We have 120,000 of them and it’s the least interesting thing we do.

Everybody else is reachable. They just don’t know about each other. The owner who would sell to the right person. The buyer who would have been right. The broker, the lender, the accountant who knows the numbers. All real, all findable, none of them connected.

So we’re building Charlie. An agent that talks to every side, remembers what it learns, and makes the introduction when two of them fit. Not a better search box over a pile of listings. The way every player on Main Street finally finds each other.

I’m co-founder and CEO. I own the product and the design, I write most of the frontend, and I spend the rest of my time sitting across from Main Street owners asking how they plan to get out. Most of them haven’t thought about it.