Saying "No" to the Money

There’s a part of my story I can’t make sense of.

I loved selling bonds. I was a sales assistant, meaning I sold on behalf of my two bosses to their clients, mostly banks and savings & loans. I sat right between both of them, clearing their trades, hearing every whisper of every call, missing nothing, and handling everything they didn’t have time for. Their clients learned to trust me. My math gift made it easy to find the story in a pattern of numbers, spot anomalies, and exploit them. As a budding writer, I enjoyed translating that story into words, lending it a bit of drama, making the pitch zing. It was clear to all I had a rare talent for the markets, and when I was 24, after I’d been on the mortgage desk for eighteen months, the firm offered me a position as full salesman, with projected first-year commissions of $300,000. The two guys I worked for earned two to four times this amount, so I knew it was no joke. I could reach their level within a few years. But for some reason, I turned the firm down, and walked away with nothing.

I didn’t say no right away. I wasn’t good at saying no to anybody’s face. So I said that sounded good, can we talk about it later? And I’d go home with my stomach in knots, dreading having to make a decision. The firm kept bringing it up, and I strung them along for a couple months, until they finally realized I wasn’t biting.

My ability to understand how I resisted that temptation only gets foggier over time. How could I be so stupid! It wasn’t my dream, but so what? Why not do it a couple years and sock away a nest egg!? I honestly don’t know. I probably had a handful of reasons at the time, but in retrospect none outweigh the reasons to have a half million dollars in my savings account. I’m too embarrassed to tell you my reasons, for it will clearly reveal I am perhaps the stupidest person of all time. Even though it worked out, and anyone would say I made the right decision, I still second-guess it.

I was drawn to the sales floor from the moment I walked the edge of its trenches. A friend had passed around my resume, and I was called in for an interview. I didn’t know what the job was. It didn’t matter – I was already sold. Men and women were running around, hollering at each other, gesturing with their arms, cracking jokes. Their sleeves were rolled up and their ties loosened and they were eating at their desks or throwing phones or barking into the squawk box. They called each other by nicknames – Q, Mayo, Doll, Dan-O, Crash. I didn’t know what a bond was, or the difference between a bid and an offer, but coming from that suffocating windowless room at the litigation firm, this looked like a blast. The gig paid about 35K. I should have bargained for more – they probably wanted me to counter – but I would have hung out on that sales floor for less.

I thrived in that environment. It was so loose, so unpoliced, that I felt incredibly free to be myself. After a year, the firm brought in a distinguished elderly Chinese gentleman, Mister Bob Chang, to cover the pipeline of high net worth investors moving to the states from Hong Kong. The firm warned me to reign in my eccentricity around Mister Chang, be a little more proper. But in two weeks I had Mister Chang standing on an imaginary pitching mound in the middle of the sales floor, throwing fastballs of wadded paper down the aisle into my catcher’s glove. During peak trading hours. Nobody said a word to me about it. As long as Mister Chang was happy, I was untouchable.

This was in San Francisco, not New York. So we had to be at the office by five a.m. It was punishing to drag myself down there at that wee hour, when the streets were empty and the sky was dark, but in some way this added to its luster – I wasn’t one of the faceless drones who filled the sidewalks at 8:56 every morning, hurrying to clock in my face time. I didn’t feel so anonymous, so indistinguishable, so unnoticed by the eye of history.

But after eighteen months, I was itching for a new environment. And I’m not good at not scratching my itches. That environment had taught me what it could.

Example 1: I went in there with a terrible fear of picking up the phone. I was the kind of guy who put off for a week calling the hardware store to see if they carried a certain brand of paint. Calling people for job interviews was way out of my league. But my desk at First Boston had over 200 direct phone lines to the firm’s accounts, all at a push of a button, and on an average day I would have to make (or answer) a couple hundred phone calls, to pitch a trade or quote a price or confirm a settlement. I had to make those calls or I was fired. It pushed me. I got over my fear. Gone forever.

Example 2: I learned an attitude, a cavalierness around money – how to show no fear and keep my wits when the sums get big. From the first day, I had nearly a billion dollars a day pass through my hands. Does that sound like a lot? It sure did to me. The first time I processed a trade for 300 million dollars, I could barely stand, I was so afraid I’d somehow screw it up. But anybody who’s worked in the debt markets knows that a 300 million dollar trade in overnight repos is actually meaningless slop. It’s a doggie bag, scraps left over from whatever the banks didn’t get properly invested that day. The commissions on it are barely enough to buy a shoe shine and a taxi ride home. A billion dollars a day is chump change, if it’s only one day at a time. So it’s that kind of attitude I learned – that a billion dollars can be mere chump change, nothing to get impressed about. Nobody ever taught me this directly or said it aloud – it was the flavor of the room, and like a catfish I soaked it up. I carry that attitude with me to this day. I’m so easily unimpressed by the dollar signs.

So maybe that’s why I didn’t stay two more years. Maybe the environment made me inure to its temptations. Like, it vaccinated me. The firm offered me 300 grand, and I was callus about it. Three hundred isn’t really that much money, I would say. It’s not enough to retire on. It’s enough to get habit forming. And that’s a pretty expensive habit. It was like play money. What would I possibly need that money for?

"Well, money is freedom," my Dad said.

"I’m already free," I shot back.

"It’s a different kind of freedom that you’ll learn to appreciate later in life."

"Then I’ll deal with it then."

That makes it sound like my Dad was some Patriarchical Quote Generator, but in fact he’d recently rebuilt his life after a difficult bankruptcy – he knew the feeling of independence one has when making money, and he knew, way too intimately, the loss of control one feels under insurmountable debt – he learned it the hard way – but I ignored that, and wrote off his words as typical Mister Cleaver Dad stuff. I had no idea how to listen.

I couldn’t take it seriously. If I was financially independent, I would never have to take work I didn’t want to do. But to become financially independent, I had to take work I didn’t want to do. Two years would lead to five years, and then I’d be like one of Don Linn’s old friends. Why waste years trying to game the system? Why fabricate excuses for why I should stick at a job that wasn’t, ultimately, the real me? There had to be a more straightforward way.

Maybe what follows is too neat of an answer, too virtuous to be real. I was obsessed with these identity questions – Who am I? Why am I here? – and I wanted to pursue this quest. But I was surrounded by men and women who showed no interest in that question. They were trying to score big and cash out. They were a few more good years away from never having to worry about money again. I might have stayed if one of them had put his arm around my shoulder and said, "This is my calling. This is my natural environment. Let me tell you how I’m making a life out of it." If I needed role models, I’d have to look elsewhere. Oddly, they are all still in the business thirteen years later, all but two at different firms. Some are rich, some aren’t, but none left the life behind.

Failure’s hard, but success is far more dangerous. If you’re successful at the wrong thing, the mix of praise and money and opportunity can lock you in forever. It’s so, so much harder to leave a good thing.