The Best Investment I Ever Made Was a Used Toyota Corolla

A few years back I cleared about fifteen thousand dollars on a real estate deal, and the first thing I did with the money was buy somebody else a car. Nothing flashy. A used 2012 Toyota Corolla for my business partner Josh, whose truck was coughing its way through its last few months. A couple of people thought I’d lost the plot. You finally net your first real profit and you hand it to someone else?

It’s the best investment I’ve ever made. Not the car. The person. And the instinct behind it came straight out of ten years in the Air Force, though it took me a while to realize that.

A visionary in a world built for order

I spent a decade in the military and I’m grateful for what it gave me. Structure, discipline, the habit of doing the hard thing before you feel like doing it. But I’m a visionary at heart. I like to sit with an idea, turn it over, and then actually watch it come to life in the world. The military, like any big bureaucracy, runs on red tape. That’s not a complaint. Some of that red tape exists for good reasons. It’s just not the natural habitat for someone who wants to build things.

On my way out I went through SkillBridge, the program that lets service members train with a civilian company before separation, and it landed me a fellowship at Microsoft. On paper, that’s the dream exit. A stable seat at one of the biggest companies on the planet, right as you take off the uniform. I lasted about a month. Corporate life turned out to be a different set of walls, and I hadn’t left one org chart just to go climb another. So I walked away from the safe thing twice in the same year, and I went all in on building my own companies.

You are not a hammer

My start in real estate was about as unglamorous as it gets. I bought and sold mobile homes that still had titles, meaning they were legally personal property, closer to a vehicle than a house. I’d flip one, stack the cash, roll it into the next. A few of those deals happened to come with land attached, so I chased those too, and somewhere along the way I picked up wholesaling and eventually renovations.

The lesson that stuck with me from those years has nothing to do with any one tactic. It’s this: never define yourself by a label. This business is full of people who introduce themselves as a wholesaler, or a flipper, or a buy-and-hold guy, as if the strategy were their identity. I think that’s backwards. Wholesaling, flipping, holding, those are tools in a tool belt. Calling yourself a wholesaler is like calling yourself a hammer. The day the job needs a screwdriver, you’re useless. Be the person wearing the belt instead, and reach for whatever the deal in front of you actually requires.

Put the people first

The Air Force repeats one phrase until you stop hearing it: put the people first. I must have heard it a thousand times in uniform. It didn’t fully land until I was building my own team.

When Josh joined me, he had all the drive in the world and a truck that was barely holding on. That’s what the Corolla was about. I put my first real windfall into the person carrying half the load, before it was obvious to anyone else that the bet would pay off. Josh went on to leave his job at a limo company, where he spent his days answering phones and booking rides for other people, to run the entire operations side of our mobile home business, which now pulls in leads from all over the country. He runs the day to day. I focus on lead generation. I trust him one hundred percent, and that trust is the only reason I was free, about a year later, to launch a second company that buys and renovates houses around Summerville, South Carolina.

None of it works if you treat the people around you like line items. The military taught me that lesson in a classroom. A used Corolla taught it to me for real.

The real enemy is the clock

People assume the hardest part of entrepreneurship is money or competition. It’s time. There is never enough of it. Nine o’clock bedtimes quietly become one in the morning coffee breaks, and you learn to function anyway.

The stretch that nearly broke me was the last three months of my military transition. Everything had to line up perfectly for the cash flow to cover the bills, every month, with no slack in the rope. That is a grind in the truest sense of the word. What pulled me through wasn’t willpower alone. It was taking inventory of my own tool belt. I had taught myself to build websites and generate leads for my own companies, so I started offering the same skills to tradespeople, the plumbers and HVAC guys and electricians who keep every other business running. That became a third company, it steadied my cash flow when I needed it most, and it lets me help other owners grow the same way I did. When you’re out of hours, the answer usually isn’t more hours. It’s making the hours you already have carry more weight.

Who it’s all for

So why keep doing the one in the morning coffee? For me the answer has two names, and they’re both under four feet tall. My two kids are my biggest motivation. I love laughing with them, playing piano with them, singing with them badly while they sing back worse. They are so full of joy, so completely innocent, that ten minutes with them will remind you exactly why you’re building something in the first place.

If you’re standing where I stood, staring at a leap you’re not sure you should take, here’s what I’ve got. Bet on people early, starting with yourself. Refuse to shrink into one title, because you’re the tool belt, not the hammer. And know who you’re really doing it for. The businesses are just the vehicles. The people are the destination.