[Note: This is a long story -- but I promise it's worth reading to the very end. If you don't have time right now, bookmark it for later and come back with a hot cup of tea... or a warm glass of whiskey.]
I am seated in the back room of North Beach Citizens on Columbus Ave, across from a man in his mid-50's whose hand I've just shaken. He is composed and articulate, with soft white hair and delicate frameless glasses framing an even, intelligent gaze.
If you remember the unusual Christmas request my brother made back in November, that's why I'm here: to perform an act that is intended to be both 1) genuinely selfless, and 2) slightly uncomfortable.
Which is to say, I am here to interview this gentle man about his experience with homelessness.
When Tom's* story begins, he is riding a tractor alongside his grandparents, who raised and provided for him alongside his Mom.
At age 6, he is already being groomed to take over the family operations -- including one of the first sugar beet businesses in America, and later a large alfalfa seed company. "My grandfather was a gambling entrepreneur; he took gambles. Farming is the ultimate gamble because you have no idea what's going to happen. In the good years, Grandma always got a new Cadillac."
Tom is fortunate to attend a good private school and receive a partial scholarship to the University of Miami -- but he detests Florida ("a terrible state, very racist, with the worst damn weather imaginable"), and after a year and a half at a fraternity that would put Animal House to shame, decides to leave and take over his grandfather’s franchise.
By the end of his first year in business, Tom has 35 people working under him.
"One day I was picking up a bunch of checks from a customer, a guy who ran a leading investment bank in SF, and he said, “whatever you do, it must be illegal, because you guys make way too much money. Why don't you drop by the office on Monday to see what we do?”
This is how Tom becomes the youngest stock trader in the country. He is given responsibility for thirty million dollars.
"It was trial by fire," Tom laughs. "And I wasn't even good at math!"
Nevertheless, Tom finds the culture of trading "interesting," because "capital markets are a man-eat-man world, it’s take no prisoners. And we were vicious on the street, we took 2.5% of the volume of trading with 80 people. And our boss would stand behind us yelling and screaming all day long and if we made a mistake we'd pick up the phone the next day and intimidate the other side to reverse the trade. We were living on adrenaline and very little sleep."
Through trading Tom gets turned onto technology, and makes a successful foray into selling mini computers to medical researchers at a time when they cost as much as a house. Then he pivots into entertainment, co-founds a new age music record label, and signs the first independently distributed album to go gold. "But my partner was a whack job, so I went down the street to our competitor and took them from two hundred thousand in revenue to $5million in a year and a half."
At this point, Tom is making "a tremendous amount of money" and spending it on the things a person in their 20's might: "clothes, travel, bringing in sushi masters, a place in Tiburon, a place in LA." He also has a habit of giving away pianos, violins, and flutes to talented artists who hail from poor neighborhoods -- believing that "when you have an instrument, you have a way out."
As such, "you burn through a few hundred thousand bucks before you know it. And I’ve always been generous with people. I got that from my grandparents."
Later, Tom is being "heavily courted" by Apple, and sees an opportunity in multimedia. So he launches one of the first CD-ROM companies, calling it "Zelos" after "the Greek god of interest and enthusiasm." He sets up shop on Pacific Ave -- just two blocks from where we sit now.
But alas: "We were too early in the market, by maybe two years. And then the economy crashed in '91-94. So I lived in my office for a year. It was the first time I was practically homeless."
During this time, Tom sees how hard it is for entrepreneurs starting businesses to understand the venture capital process. So he starts coaching other founders on what they need to do to grow their partnerships, and helps them raise over half a million dollars.
Somewhere in the background, he also helps start a couple entrepreneurs' associations to "help spread the gospel of entrepreneurship" -- one of which becomes what is now known as EO, with chapters in 54 countries and combined revenues of over $1.5 trillion.
The other would yield NIFTE (National Institute for Teaching Entrepreneurship), which matches members with troubled kids from the inner city to help them structure their own businesses with a grant of $200 dollars.
Armed with that amount, one 9-year-old girl from upper Harlem decides to get into the office supply business. "The father of one of our entrepreneurs donated a whole bunch of office supplies, and she took part of her money to go look real professional. And we taught her how to bravely walk into businesses and say, "you should buy all of your pencils and pens from ME." And she had this swagger! She was helping her family pay rent by the time she was 10."
Then, at a dinner party, Tom meets a guy who has just been hired by a family in Dubai to build a massive $30billion development. Without revealing who she is, Tom gets the guy to hire his girlfriend as the 4th employee for the project. So now Tom moves to Dubai, where he takes to advising super wealthy families on bundling their assets, "basically a very crude form of investment banking," while his girlfriend plays with an $80million marketing budget.
Then, 9/11 happens.
"I got a call from my personal investment bank, saying “shit just hit the fan.” Then my phone went dead, because my Verizon account, the tower, was in the World Trade Center. So I came back to California."
Not long after, Tom gets a call about his mom from her friends. They say she's real sick, and her finances are in disarray.
"She was missing doctors' appointments. She was deeply into dementia, in multiple dimensions. She didn’t have the right medical care, so I had to get her through several operations." So Tom must go through the trauma of sifting through his mother's house and memories, in order to move her into a 2-bedroom suite overlooking the river in an expensive assisted living facility.
"Then, on Day One, she tried to commit suicide, right in front of me. She stepped right out into oncoming traffic."
This is when Tom's heart issues begin.
"I was on the verge of having a heart attack or a stroke -- my blood pressure was out of control." This episode also triggers an intense depression, something Tom had struggled with, but mostly ignored, since the age of 17.
This, in turn, affects his relationship, which comes to an end after many happy years.
... And next, come the surgeries.
"My heart was not getting enough oxygen to my brain, so that triggered memory loss, skin problems. I had trouble even walking a couple blocks without being out of breath. It was a downward medical spiral."
Meanwhile, the assisted living facility can't keep Tom's mom, who is being physically and emotionally abusive to the staff. She must be moved through three other places, each one less nice than the last. Finally she calls in a bomb scare, and gets herself locked in a psych ward for 6 weeks.
"That’s when it became clear that I was no longer able to take care of my mom. I had to make her stay in the psych ward. So, that rips your heart out."
At this point, Tom's health is interfering with his ability to work. Most of his money is gone, and he no longer has health insurance.
He goes down to southern California to stay with friends, and then begins "bouncing around, not really knowing where I was going." He has about two years of stability when he finds work that does not tax him physically or require travel, and discovers that he can live on $2500 a month.
Then Tom develops "syncope," which is a rapid loss of blood pressure that causes you to faint. "The second time it happened, I was driving my car at 50 miles an hour. I passed out and crashed into the median. I had to sell my car -- so now I’m not mobile anymore."
Then in May, for no good reason, Tom's landlord wants him out.
"I didn’t have a place to go. I did not have the money to move into a place. Housing costs are insane. No one wants a 54-year old guy as a roommate. People say, oh, but you can stay with friends and couch surf. But this is not so. Relationships are too important; you don’t want to overstay your welcome."
So Tom gets an annual membership to 24-Hour Fitness. "There’s my shower, hot tub, steam room, right there." At nighttime he walks around, sees friends, gets a sandwich and a beer, watches the game. But he is surviving on very little sleep -- a dangerous game to play with his heart.
Now Tom is sleeping on the streets. "I found wonderful little nature sports, like the canal behind the ballpark where the houseboats are. Under Coit Tower, lots of trees there, very quiet."
Finally, a fatal blow is dealt.
"You know the big rucksack you see every homeless person has? Everyone’s got their whole life in that. One day mine was stolen while I was taking a nap. Inside was my lifeline, my tablet. So I'm cut off now, I can't consult. My wallet's gone. I still don’t have my ID back."
And yet -- even now -- Tom is "not at all" transparent with his network about what is happening.
"I didn’t tell anybody. Only two people knew. It's embarrassing... having had a really good life, and now being here."
When you’re homeless, Tom says, probably the first thing you want is a good coat. "What I didn’t realize is that the other thing you really need is good shoes. You’re outside walking all the time, so your feet go to hell. Clean socks are always a challenge."
The first service that brings Tom in from the street is the promise of a hot shower. "That intake got me into the system, got my first appointments to get food stamps. On intake they determine what kind of work you can do, and they immediately declared me disabled. I probably knew that already, but you don’t want to acknowledge these things."
One thing people don’t realize is how tricky it is to find food. "Food stamps will get you one meal a day, plus a few things from the grocery store. I’ve never stood in line for a meal -- not yet. I’m not going to panhandle. I’m not going to shoplift. But I can tell you every hotel in the city where I can get an apple."
Tom shakes his head, and says:
"And boy, even being educated and accomplished, going through all the appointments and the paperwork -- it is unbelievably complicated. Being homeless is a full time job."
There are, apparently, many infuriatingly strange things about it.
For example, this is his second month on food stamps. One might assume, as Tom did, that the card would be recharged on the first. "But it doesn’t work that way. So on the first I walked into Subway to buy a sandwich, but the card was empty. The card actually gets recharged on the date of the last number of your case number. So mine didn’t get refilled until the 4th. Who walks around knowing what their case number is?"
He sighs, relenting. "At least now I have a case number. It’s a relief, I can get some support."
To take another example, when you’re homeless, General Assistance pays you $66 a month. "But when you’re in a shitty SRO, you get $460 a month. When you’re on the streets you desperately need every quarter, every dime. It is completely upside down."
And as for the SRO, it’s "as cold inside as it is outside. The water is barely warm. And it stinks. It’s two blocks from the hospital so you get the sirens, and there's the freeway onramp so you get all the trucks going by. It’s two blocks from Larkin, with all the heroin dealers and the hookers.
"It’s temporary, I know that. But it’s given me an address."
Tom does see a way out for himself, once he gets his MediCal card and can see a doctor for the first time in two years.
Once he gets his heart aneurism stabilized and operated on, he still has "a lot to contribute and do. I still want to be in society. I just can’t do it the way I have in the past. I can no longer manage 35 people, can no longer work 18 hours day 7 days a week, or travel around the world nonstop."
When asked what he wishes everyone knew, Tom has this to say: "People need to know that 25-30% of those who are in my situation are still active in society, still contributing.
"I wish more people knew how many of their friends are on the edge. People you would never suspect are on the precipice right now."
"One of my closest friends, who I met through investment banking, he was even higher than I was, making millions every year. Smart guy, PhD, lived well. Now he’s on the verge of losing his place. He’ll be walking in here next week. He’s been through a terrible divorce, he’s got 3 kids, filed for bankruptcy, does not have a car. Right now I’m literally coaching him on how to get through the process I just went through."
To this day, only five of Tom's friends know about his situation.
"I have friends who have been homeless themselves who don't even know. I saw my sister a few weeks ago -- she has no idea." And Tom has other friends he sits with today, who say: "Can you believe this city actually gives money to homeless people?"
Tom shakes his head, and offers a laugh.
"People need to know, there’s not a safety net. Ninety days, just for a shelter bed? Where do you keep your stuff, what do you do? People believe that some people are just leeches on society. They assume that everybody’s a drug addict or alcoholic, and it’s just not the case. There are a lot of highly educated people here.
"Truly... it can happen to anyone."
If you feel moved to do so, please click here to donate a pair of socks to a homeless shelter (and get yourself a pair in the process). If you don't need new socks, but still want to give the gift of dry feet, click here instead.