As told to Jeannette Cooperman
Photograph by Mark Gilliland
Robert Lipscomb grew up in Glendale, the middle son in a middle-class Midwestern family. But he bored easily. He left college to serve in Vietnam, left the military to work in construction, “started flipping houses and made a bloody fortune.” Then he gave his money away and spent two years homeless. Last fall, Lipscomb published his memoir of street life, Down Town: True Tales of Trial & Triumph on the Mean Streets. Now he’s back in the middle’s delicate balance, living in a Victorian farmhouse in Carondelet with a woman he loves and running an independent publishing company.
Glendale was the Garden of Eden, I thought, fashioned from old apple and cherry orchards and towering Dutch elms.
Me quitting college and joining the Army put most of the gray hairs into my mother’s head. But I didn’t want to miss out on history.
When the smell of cordite and smoke is in your nostrils and you’re still standing there, you feel like you own the Earth.
Being in the military is like most marriages: Half the time it’s the most wonderful thing in the world, and the other half, you’re thinking, “What the hell have I gotten myself into here?”
I flipped real estate, invested in unknowns like Amazon.com, spent my money on casinos and cars and traveled my ass off.
I reached the peak in my pursuit of all things when I married my second wife, an actress 15 years younger who looked great on my arm. It was such a total cliché, the trophy wife—but at the time I didn’t get it.
I was racing for a goal that was a receding horizon. There’s a certain level of comfort I require. But you can get wrapped in a loop that will make you crazy.
The whole world is set up to cater to the princes. If they treat you like a prince, even though you know it’s not true, it’s like a shot of a strong drug.
What white, Anglo-Saxon middle-class American doesn’t already feel like he owns the world?
A lot of us frame our lives as they appear to other people. But it’s when you’re home with the door closed that you’re looking at yourself in the mirror.
I put on my brand-new backpack with three changes of clothes and a good pair of shoes, gave the keys to the apartment manager and walked out onto the street.
By then I was in a kind of fugue state. Clinical depression is what they’d call it, but I would call it renunciation of the world.
I knew I had to walk away from it. I transferred huge assets to my son and started giving money away to people on the street.
My first year on the street was discovery and nonengagement, and frankly the lack of responsibility for the first time in my life. The second year is what I call the Year of the Trap.
There are sufficient resources out there—housing, temporary work, food—that if you are utterly unmotivated or have no memory of a life of quality, it’s just comfortable enough to trap you.
Everybody on the streets suffers from some mental malady. Quite a few of the older white guys have PTSD.
Advice for surviving? Be calm. Find some peace and tranquility in nothingness. It’s gonna be what it’s gonna be.
I got along fine with the other guys. It’s called making small. You have to talk less, because for sure you are going to say something that will provoke some lunatic. And you have to look like you are ready to tangle with anybody.
Christmas Day they close the shelters because nobody wants to work them. It’s rather counterintuitive, isn’t it?
I started writing, and it helped me focus. You have to tell people who don’t have an effing clue what the story is. As my thinking became more structured, I began to reengage.
Five years ago, I walked through the doors of Christ Church Cathedral’s homeless shelter. Last January, I was voted to the cathedral’s board of governors.
“Be very careful, Bob,” I told myself. “You are wiser now. Do not let this make you feel like the prince again.”
