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My parents died when I was young—Mom when I was 16, Dad at 18. That sort of starts the process. You lose one parent, it's one thing; you lose the second, it's a whole other thing. Family pulled out. You think, okay, all the uncles and aunts are going to jump in to rescue you—no, no, no. They were afraid we'd be sticky, you know? They'd invite us over, and we'd never leave.

At my dad's funeral on September 15th, his brother says, "Hey, you want to come over for Thanksgiving?" I'm like, "Isn't that in November? Aren't you worried about how I'm going to eat tomorrow night?" He's like, "Just let me know if you want to come over." Never spoke to the guy again. He didn't care.

My mother—they gave her six months to live, and she lived years. But she lived like a tornado. She was like, "Really? I get six months? Let's go!" She'd go to India, just blow out, come back two weeks later, walk in the door, and start yelling at me that I didn’t do my homework. I’m like, "Hey, where you been?" It was like a war zone. But every once in a while, I'd be sitting in school, and the vice principal would come over and go, "Howard, Howard," pull me out of class. I'd go, "What is it?" He goes, "It's your mom." So I go running outside, and she's in the car. I'm like, "Are you okay?" because she had terminal cancer—she was going to die. She goes, "Yeah, let's go." And we'd go to the city, to art galleries. Then she'd take me to the opera. And after the opera, we'd get bombed at the local bar. I mean blitzed. And I’m 15 years old, blitzed out of my mind. Then we'd drive home to Long Island, where we lived, what I called "Rodeo." Roll down the windows and go crazy, because she wasn't worried about dying.

"Every day I’m alive, I'm going to make sure I'm happy and living my life, because this is the joy," she said. My view? I learned it from my mom. You don’t die—you lose the joy of living.

I said, "Dad, I really wish something bad happened to our family just so you would have something actually worth complaining about." That’s how visceral I am to complaining. Everybody complains about dumb shit, and then something happens in their life that’s worth complaining about, and they get really reset.

Until we moved in sixth grade, you’d just be on the street, playing football. Everyone would pick the name of some Dallas Cowboy or someone, right? "Joe Namath!" And you'd yell, "Car!"—off the street. Car goes by. Back out there. That’s the way it always was. Then we moved to a more suburban area, where there was no one else on the street, so you just rode your bike anywhere. And your parents had no idea where you were. You just came back. My mom literally had no clue where exactly I was from 1982 to 1989. She knew I was in the general vicinity, but she would literally open the door and yell—like out of a throwback sitcom—about lunch. It was like The Wonder Years. She’d yell, and if we were more in the left direction toward Eric Godfrey’s house, my sister’s friend Denise’s mom would hear it, open her door, and yell. If we were up top near Robbie’s house, Robbie’s mom Eleanor would hear it and yell. In case we were by Bobby Duffy’s, she’d yell. It was crazy.

I really believe we’re blaming a lot of things for anxiety today, but the over-coddling of knowing everything about your kid—where they are every second—is a problem. We grew up getting in fights, getting hit by a stick, reconciling without parents. That’s how you learned to function.

The number of people I’ve met who have a fucking app on their 23-year-old to track them at all times? That’s crazy. And then they wonder why their kid can’t stand on their own two feet. No shit. You created a bubble baby.

Before the internet, television was life. No phone, no internet—television was life. Eighty million people would watch an episode of MASH at 10 p.m. And there’d be this public service announcement: “It’s 10 p.m. Do you know where your children are?” Because sometimes, they forgot we hadn’t come home yet.

It’s hard to be hungry when you’re fed.

I had a summer job, but I stayed for the whole semester—six months. I didn’t want to just watch; I wanted to work. So I pushed to do the job.

- At that point, Howard, just to educate me—was the Wall Street gig like, "Yo, you go here, you make money"? Was it already epic?
- That was your way out. If you had no money, all the street kids in Brooklyn, the Bronx—that was it. Now, people think of private equity. Back then, it was Wall Street. But I didn’t know what the fuck it meant. Wall Street equals money, but you had no idea what job you'd get.

I got this job. I just wanted to do it. And I figured out the boss. I started writing him notes: Do this. Did you know this is happening? He never spoke to me. Then, on my last day, he calls me into his office. He takes out his desk drawer—he's got every note I wrote. Wow. He starts talking to me about all of them. Then he offers me a summer job next year. I’m golden.

During those six months, I was getting direct deposit—$250 a week—straight into my bank. When I went back to college, I called the boss: "You gotta stop it." He goes, "You coming back this summer?" I said, "Yeah." He goes, "Ah, keep it." I thought he was giving me $250. No—$250 a week. The whole semester. When I got the second check, I went to the dining center, leaped onto the table, and did The Hulk: "YEAH!" I took girls to restaurants. I bought gas. I was the king.

First lesson. I go onto the trading floor. Huge football field of people. I’m lost. So I find the winner in the room. I walk around, watching. Then I pick someone. I walk up and say, "What kind of coffee do you like?" I get him coffee. Next day, some people start saying, "Black with sugar," like I’m the coffee guy. Then I find someone who likes me. He says, "Sit down." I have a job.

He calls his best client. "You get your young guy, I’ll bring mine." We go to dinner. I make sure that 23-year-old is my best friend. I follow him around. I buy beers. And when he starts trading? He calls me. The whole floor goes, "Who the hell is Howard?" Me. I run across the trading floor. I take the call. I just cut the line.

Effort is everything. If you're smart and clever? Game over. That’s what a billionaire is.

In 1987, interest rates start leaping. I tell everyone, "Short the market." No one listens. I start borrowing money. The market keeps going up. By August, I’m totally broke. Then, in October, the market crashes. I make just enough to pay everyone back. But I’m broke. I have to borrow money from my grandfather to pay rent. That’s painful.

That was the day the firm was mine. I hired everyone I loved. My brother. My best friend. My college roommate's brother. It became a family. That firm was on the 101st to 105th floor of the World Trade Center... and then the plane hit the building. And I lost everybody.

[ 9/11 STORY ]

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