People ask me how I got into real estate. The honest answer starts with a snowblower that did not run.
I grew up around Downers Grove, Illinois. At ten, eleven, twelve years old I was shoveling driveways and sidewalks in the neighborhood, cutting lawns in the summer, doing whatever work people would pay a kid to do. One winter, a neighbor pointed at an old snowblower in their garage. A big machine. Forward and reverse, a crank for the chute, even a headlight. They said it had not run in years and I could have it.
I took it home and took it apart. The problem turned out to be simple. I fixed it, and it started right up. Suddenly I was clearing driveways in a third of the time, which meant I could take on three times the business. And the neighbors who gave me that machine never paid for snow removal again. I did their driveway free from then on, every snow, for years.
That was the first lesson, and I did not know it yet: fix what other people gave up on, and take care of the people who took a chance on you. I have been doing both ever since.
A duplex at seventeen
A few years later I kept seeing a late-night TV pitch about buying property with no money down. Palm trees, sports cars, the whole show. I did not have any money, so as far as I was concerned the man was talking straight to me. I bought the course. It was a VHS tape, which tells you how long ago this was.
Underneath the flash, the method was simple and real: find an owner willing to hold the note. I found a duplex in Waukegan that was not even on the market, started a conversation with the owners, and worked out a deal where the sellers held the financing on the down payment. They moved out, I found a tenant for their unit, the upstairs was already rented, and the building paid for itself from the first month. I was seventeen, maybe eighteen years old, and I owned my first income property.
I learned early that the deal you can do is the one in front of you, structured creatively, not the perfect one you are waiting to afford.
Ten houses by twenty-two
Waukegan had neighborhoods full of simple three bedroom, one bath homes built during World War II. Same floor plan, street after street. I started buying the ones that needed work, well under market, fixing what mattered, and renting them out. The rent covered the mortgage, taxes, and insurance with room to spare. By twenty-two I owned ten of them.
It worked. But here is what nobody tells you when you are young and collecting rent on ten houses: you also own ten roofs, ten water heaters, ten furnaces, ten tax bills, and ten insurance policies. Every system in every house is your problem. That math eventually pushed me toward multifamily buildings, and later into commercial property, which is a story for another post.
The lesson I paid the most for
Not every chapter was a win. I owned a mixed-use building through the crash years and watched commercial tenants disappear and rents fall while the bills kept coming. I took risks as a young man that I would flatly refuse today, including buying a former gas station property before the environmental file was clean. That one worked out, and it taught me how easily it could have gone the other way. Experience is what you get when the outcome was not guaranteed.
Those years are exactly why I work the way I do now. When I tell a client that a thoughtful process beats a rushed one, or that the small details are where deals are won and lost, that is not something I read in a book. I paid for those lessons with my own money, my own buildings, and my own winters.
Thirty years later
Illinois made me. The Mid-South is home now. Today I work with buyers, sellers, and investors across Greater Memphis, West Tennessee, and Northern Mississippi with Berkshire Hathaway. Residential, land, commercial, leasing, investment property. The markets have changed. The tools have changed. The core has not: understand the story, do the work, tell people the truth, and take care of the ones who take a chance on you.
Somewhere in Illinois there is a family whose driveway I cleared free for years. That is still the business model.