Howard Lutnik's Emotional Journey | #1 of 2024 Top Podcasts

Hey everybody, welcome back to another episode of the Gary Vee Audio Experience. I'm Mike from Team Gary Vee, and today I'm especially excited to share with you an episode of the podcast. And this one Gary sits down with Howard Letnick, CEO of Canter Fits Gerald. Howard's journey from personal tragedy to becoming one of Wall Street's most prominent figures is nothing short of inspiring.

In this episode, we'll explore the lessons he learned from building a multi-billion dollar firm to overcoming adversity and leading through some of the darkest moments in our nation's history. I hope you all enjoy this episode. Make sure you come back tomorrow to listen to the second part of this incredible conversation. Enjoy!

My parents died when I was young. Mom, when I was 16, dad at 18. So that sort of starts the process. You lose one parent, it's one thing. You lose the second parent. It's a whole nother thing. Family pulled out. You think, OK, all the uncles and aunts are going to come jump into rescue. No, no, no. They were afraid we'd be sticky.

You know, they didn't invite us over, and we'd never leave. So at my dad's funeral, my dad gets killed in September. So my mom dies of cancer. Long Island Classic, long Island breast cancer. Dad has cancer, goes in for his first chemotherapy shot. We had no money. So we went to a local hospital. Nurse makes a terrible mistake, gives him someone else's dose, and kills him on the table. September 12, 1979.

Okay, so at my dad's funeral, September 15th, my dad's brother says, hey, you want to come over for Thanksgiving? I'm like, isn't that like November? Why aren't you worried about how I'm going to eat, say, tomorrow night? He was like, just let me know if you want to come over.

Never spoke to the guy again. Got in care. My sister's 20. I'm 18. My brother's 15. Three of us. That's it. On her own. Not really any money. Sell the house. Just try to figure it out. And that's how we start the world. So my college takes care of me.

Yeah. Steps up in a crazy way and says, we want you to come back. Because I was dropping out. Take care of my brother. Dropping out. Going to run like my dad's travel business. He had a travel agency. He wouldn't run his travel business. Like, I have any clue. And he had to be a team. Like, I don't even know what a check looked like. Right. My favorite thing was the only checks I'd ever seen were my mother's checks. They had, like, a sunset on them. So I thought, yeah, you got a sunset check. Yeah. And then one day I was sitting with one of my friends, and he had, like, a regular blue checkbook. And I was like, what is that? What do you get, those? Like, I got this little sunset thing. I got boats.

And so Harvard, small school in Pennsylvania, calls me and says, come back. We want you to come back. We got you. And we got you. And they went back. So I ended up having the life I was going to leave. I put my brother in a boarding school. Yeah, I was going to ask you where to be.

And he lived with me on the weekends. So he was with me on the weekends, and he's 15, turning 16, trying to pick up checks. You want to talk about learning life fast, getting out of college campus every weekend. So he's sleeping in my dorm room and trying to pick up checks on the weekend. Just to bounce around a little bit, you know, in hindsight.

That's a lot to go through. You know, it's really interesting. I've always, you know, since we've gotten to know each other more recently, there's a kind of instinct connection you have with people. I am very fortunate that that did not happen to me, but I would argue my parents losing parents at a very, very young age.

was foundational in how I see life. I grew up my entire childhood fearing my parents' death. And I mean, not like normal people who, like, it crosses your mind. I mean, like, it was the major backdrop conversation I had with myself, my whole life. My mom lost her mom at six.

in the Soviet, my parents grew up in the Soviet Union. So like, let's start that. And then my dad lost his dad at 16. And it was just a huge currency in my whole life. My mom lost her dad when she was 21, too. So she like very quickly was down to zero. And my grandma, my mom, my dad's mom was around a part of my life. But it's interesting, even though I wasn't the affected of it directly, it was a huge factor in how I see life.

of the three of you, how did you all take that moment? Well, 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. And she'd go to India and just blow out and 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? And it was like, war zone. But every once in a while, I'd be sitting in school and the vice principal would come over and go, how are you? Pull me out as a classic. I go, what is it? He goes, it's your mom. And so I go running outside and she's in the car. And I'm like, what? You OK? You OK? Because she had terminal cancer. She's going to die. She goes, yeah, let's go. And we go to the city. We go to art galleries. Then she'd take me to the opera.

And then after the opera, we'd go get bombed at the local bar. And I mean blitzed. And I'm 15 years old. And I'm blitzed out of my mind. And then we'd drive home to a long island where we lived what I called rodeo. Roll down the windows.

Right? Woo-hoo! Like try. And just, because she wasn't worried about dying. And I guess she wasn't worried about me dying either, which is little. And by the way, kids, just to give you context of this era, no seatbelts either. Just so everybody understands. This is real rodeo, baby. Really rodeo. And let me give you something else that was happening on that highway as they drove from New York, like throwing the McDonald's out the window. That's how we disposed. It's crazy to think about some of the social norms of the 70s and early 80s. Anyway, nonetheless. So that was it. So I learned to live.

live every day. So let me give you a hint. Today is the joy of life. Right here, right now, this is it. You know, never be depressed. I had non-Hodgkin's lymphoma, I had cancer. And people would say, how are you? I'd say, I'm good. Because every day I'm alive, I'm going to make sure I'm happy and I'm living my life. Because this is the joy. You don't, my view, I learned it from my mom. You don't die. You lose the joy of living.

My relationship with complaining is built on this thesis. Listening to what people complete. Dad, don't be mad at me. I know you always say, like, you give mom all the flowers and you rasp me. But this is true. There was one time that I got pushed so far with my dad being upset about dumb shit.

that I said to him, you know, dad, I mean, and this is like, just for context where everyone is listening, like, after a million things my dad has said in his life that he's complaining about. In business, normally, my dad is funny with business. He takes everything personal. I take nothing personal. So you can imagine our combos. But finally, there was one time when I said to him, I said, dad, you know, 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 based on this thesis. Everybody complains about dumb shit and then something happens in their life that's worth complaining and they get really reset. Correct. So I learned how to live from my mother. Yeah. And then so I was always focused on living because I learned it. I learned it when I was 16. Yeah. You know, and so... Form little ears. A lot happens in 14 to 18.

So when my dad got killed, and the second one, you lose the second one, you're in hell. You're literally in hell. It smells like hell. It tastes like hell. I didn't know what the hell to do. My sister's 20, I'm 18, I don't know what to do, and it was a disaster. Everything about my life that day was a disaster. The lawyers stole our money. Everything like you have kids with no one protecting them, and you just get shredded. You just got shredded. I don't have any money to begin with, and whatever little money we had was shredded.

Okay, so me, my sister, my brother, we just live. Was your sister in college at that point? So my sister was in college, so basically, he goes to boarding school near me, lives with me for one year. She graduates, and takes him. And then she takes him, and she goes to Syracuse, grad school, she gets a JDM MBA, and he lives with her, and graduates from the public high school, right by Syracuse. So he just goes to the public high school, and then he just wants to be me, my brother.

He just decides he wants to be me. And so he joins, he goes to Wall Street because I was working on Wall Street at the time and then eventually joins me. But that's the thing about my story is I was really focused. I really understood things. And there's lots of stories about how I made it, but I got all the way to the top of the world. Yeah, let's be before we go getting top of the business world and things of the nature.

Take me back prior to these incredibly challenging events. Prior to that, five, you know, when I think about my professional career, so much was happening at five, seven, nine, 11, 13, that I now look back on and be like, oh, this shit makes sense.

Of course I fucking, when it's snowed and everybody wanted to make a snowman, I'm like trying to convince Robbie Turda Guerrero Godfrey or Andy Greco or one fucking kid in my neighborhood of like, let's grab a fucking shovel and ring every fucking doorbell in Edison, New Jersey. Like of course it was in me. You know, obviously you have these traumatic and life shaping events and obviously you had a mentor and your mom that you just described about living but

Your mom was there, obviously, in those years as well. Were you that person at 6, 9, 10, and 12? Before these adversities came, what was 7 or 10-year-old Howard? I was always figuring out how to make money. Always. So I'll give you an example. I would buy a pack of baseball cards. Yep.

Okay, and then I would take all the old cards. And I'd make new packs. And some had one new card, and some had three new cards, and some had five new cards. And I sold them, you know, so that when I sold out all these, right, when I sold them all out, I made like three X, the pack, but you took risk.

You know, for two cents, you might get five cards, which is way better. Well, you might get one and get blown out, right? And so, and I would sell these cards. And I, of course, sold T-shirts. Remember the famous ones with like the arrow? I'm with you, stupid. Yes. Like those, I sold those. I basically, I did all these things. Yeah. I just hustled to make money all the time. We used to have carnivals in my house. Well, you probably were bad at school. Oh, I was, I was a square.

Okay, I was good at school. I played tennis, so I was serious sports, and I was good. My sister had fun and lived a good life, and my brother just lived through like a world of shit with my family, you know, and health and stuff like that. Were you good at school, because you were serious about tennis, and you wanted to be on the tennis team, or school came natural to you, or you wanted to make somebody proud of your mom or dad, or something altogether different?

They had enough they didn't need to deal with me. Okay, I don't want them to have to deal with me Your sister was having enough fun that you saw them dealing with her and you're like fuck it I just don't want them to deal. Yeah, they not to deal with me So I was just like, you know, I just was fine. Okay, I was fine and and you learn how much did the neighborhood raise you?

Like, like, did you play outside a lot? I don't mean like the 50s and the 40s, but like, were you outside constantly? Yeah, when I, where I lived until we moved in the sixth grade, you would just be on the street, you'd be playing football on the street, everyone would pick the name of some Dallas cowboy or someone, right? And they'd... I hope the name of got in the middle of that area. And you'd yell, and you'd yell car, right? That's how I play. Off the street, carnival, sorry. So that's the way it always was.

You know, and then we moved to, like, more suburban, suburban, you know, where there was no one else on the street, so that you just rode a bike anywhere. And then what you would do is you'd just ride your bike. Yeah. Right? And your parents didn't have any idea where you were. No clue. They never knew, and you just came back. My mom was dark. My mom literally had no clue where I exactly I was from 1982 to 1989. She knew I was in the general vicinity, but she would literally open the door and yell.

Yeah. Like, like, full fucking, like, out of a fucking, you know, throwback sitcom would literally open the door and yell about lunch. And then, like, the way it worked, it was, like, out of a fucking wonder-years episode. She would yell. And if we were more in the left direction towards Eric Gottfried, then my sister's friend Denise's mom would hear it.

and literally opened her door. And then she would yell, if we were up top, closer to Robbie Turnix House, Robbie's mom, Eleanor would hear it. And she would yell in case we were by Bobby Duffy's. Like it was like fucking crazy. And I really genuinely believe that we're trying to blame a lot of things for where the anxiety and all this is, but the overcoddling of knowing everything about your kid, every second of everything we're in. We were growing up, like, I don't know, fights and getting hit by a stick and like,

fucking reconciling shit without parents was you were learning how to function.

My wife has never had a minute when my kids were younger than 18, where she didn't know where they were. Not even one minute. I'll be honest with you, I'm aware of how modern parenting last 30 years has been. How about the fact now that it extends way past 18? The amount of people I've met who have a fucking app on their 23 year old to know exactly where they are physically at all times is fucked up. That's crazy.

And it's not, it makes a 23 year old feel like they're, no shit they're acting like they're five. No fuck they suck at work. They're fucking zoo animals. They can't live in the jungle. They're fucking being tracked by their fucking 59 year old parent. They're 24 fucking years. They're on the payroll. They're being tracked. And then you're upset that they can't stand on their own two feet. No shit. You created a fucking bubble baby.

I think the neighborhoods really shaped us. Fair. I don't really think about that until just now. You're right. You're right. You're making my childhood where my parents had no idea who we were. And we just came back at night, right? When it was dark, I had to come back. I had to be at home within 20 minutes of dark. How was it? There was a fucking thing on all our TVs when I was growing up that said, it's 10 p.m. Do you know where your children are? Howard!

I just need everybody to understand this. Kids, kids, under 30, if you're listening, listen to me, on television, which remember pre-internet, it was life. It's no phone, no internet. Television was life. 80 million people would watch an episode of Mash.

At 10 p.m., there would be this like public service announcement commercial in the 80s that would come up and be like, it's 10 p.m., do you know where your children are? Because sometimes they forgot that we hadn't come home yet. Be a parent, that's it. I tell you about being a parent, try to pay attention, be a parent.

I mean, it's crazy. Anyway, I was just curious. Like, I really do think the East Coast, and listen, the West Coast got their skater surfer version of this, but fucking 60s, 70s, 80s, New York, New Jersey, Long Island, instead of like, just that outside, and it was just fucking raw. Like, I just think, I really think until you get punched in the face, you're not fully like a functioning real man. And I think that, and that's figuratively, or...

When modern bullying became a thing in the last 20 years, I was like, oh, this is sad. Like, let me get up to date on this. When I dug under the hood, I'm like, oh, you mean every day of first to 12th grade?

Like, it's just we're in a very different era, and it's by the way, what concerns me is it's so obvious, it's similar to what happened with the Roman Empire and every other Empire. A lot of what Europe's shortcomings, Europe has amazing strengths, but a lot of its shortcomings, it's just sustained prosperity. It's hard to be hungry when you're fed.

All right, so I graduate from college, and a friend of the family connects me with Bernie Cantor, and I get a job, okay? And I get a job, but... Educate everybody, you know, you're in your own world and tell everybody about Bernie Cantor. So before I get a job... 99% of people like who is Bernie Cantor, they're looking... So before I get a job, I have a summer job, and I get that summer job. A friend of my family gets me a summer job, and it puts me in a company that's on Wall Street.

It's a brokerage company on Wall Street. I don't know anything about it, but it gets me a job. All my friends go to Europe for the junior year abroad, and I go to work. So I get an apartment in the city by myself, and I do like a summer sublet. You used to go to the village voice. And you look at a sublet in the back and the classified ads. I mean, people don't have any idea. You look at the newspaper, and I get this apartment, and I go to work.

What year is this? This is, I guess it's 80, 81. Kids, again, I love doing this for the audience. New York's a fucking shithole. Just so you understand 1981, 80 New York, it's the New York you think it is. Like all the kids that come and intern here that are still a little bit in a bubble, they're like, oh, New York is way less scary than I thought. 1980 New York?

It was a fucking shithole. The city was bankrupt. It was a mess. This is right before the Reagan thing kicked in. This is like a tough New York. Yeah, it was fun. But you know, so I got a job and I go work there and I had a summer job. But I stayed for the whole semester, so I worked there six months. Oh, interesting. And so I wanted to work. I didn't want to look at it like a movie. I wanted to do the job. And so I pushed to do the job. And then at that point, Howard, just to educate me,

Did the Wall Street gig, was that like, yo, you go here, you make money? Was it, was it, was the brand of Wall Street epic? Or like, where was the brand of Wall Street at that moment?

That was your way out. So when you had no money. Right, all the street kids in Brooklyn, the Bronx. It's like when you think of private equity now or the way to make big money. It was the way out. Right, so you just thought Wall Street. That's what I thought. So I was just thinking, well, but I didn't know, like you said the word Wall Street, after that I had no idea. Right, you knew that I could have been anything. Right, Wall Street equals money, but you had no idea what the fuck was actually worth. So you could have the worst job of the best job. I was just random, whatever I did. So I got this job and I just wanted to do the job.

And I figured out that the boss, just figure out how to get him with the boss. So I just figured out how to get him with the boss. I would write the boss notes saying, do this. This is happening. Did you know this is happening? This is happening. And at the end of my six months working there,

The boss calls me into his office. He never spoke to me the whole friggin six months I was there. Never. I would send him notes. You don't have to say fucking on this podcast. Just like it's sense how hard I'm trying. I knew what I'm against. I get it, but I know who you are. And I just want you to know that you found a very good place to be. You can get away with all of it. Go ahead.

All right, so then he doesn't talk to me at all the whole time. And then he calls me in the last day and he takes a desk out and he's got every note and wrote. Wow. And he starts talking about this and this and this and this and this and this and this. So it was really good. Epic. And then he offers me a summer job next year. Right. So I got a summer job next year. So I'm cool. I'm golden. And here's that big moment. I learned during those six months I was getting direct deposit where they put the 250 bucks a week that I was getting paid.

into direct deposit. They put it right in the bank. So when I go back to college, they send me the pay stub. And I'm like, no, no, no, I call the boss up. I said, no, I went back to school. You got to stop it. He goes, you're coming back this summer? I said, yeah, keep it. So I thought he was giving me $250.

No, 250 a week. He kept paying me the whole semester. And when I got the second check, I went to the dining center, and I leaped onto the table, and I did the hulk. I was like, yeah, I got 250 bucks a week a week. I took girls. 1980? I took girls out to restaurants. I took girls to restaurants. I bought gas for a car. I was like, wait a minute. I was the king.

going to restaurants 250 bucks with inflation in 1980 in the middle of nowhere in Pennsylvania, I'm surprised you didn't buy fucking restaurants. It was a lot of money. So I was like the man, okay, because I would buy all the beer for everybody. It was like fine, it was great. And then I went back that summer. So that company sells, buys a division from Bernie Cantor.

Okay? So Bernie Cantor is like this famous industrial guy, right? Famous Wall Street guy. Rockstar, largest collector of Rodaz in the world. You know the thinker? Yeah. Right? Like he's the man. He's a wing named after him at the Met. Okay? And he sells a division to these guys. These are just regular Italian guys. And they buy the company from him. And

They invite me during that summer to work on that deal. So I'm sort of in the room like the young guy, like whatever. I'm just a young guy, but I'm a pet of the boss because he likes me now, right? So Bernie Cantor sees that I'm a pet of his. So they call me up and they offer me. They say, whatever he offers you when you graduate, I'll pay you though.

So they were offering me like 20 grand, right? So now I'm going to make 40 grand and go on a can of a chair. Again, I need everybody to hear this. 1981 or two or whatever year we're talking about 40 grand. Real numbers. Yeah, yeah, that's real. It's like making a hundred. But it's different. And you know this because you definitely you know this better than I do. But.

100 now with the way everything is played out with all the money that was printed. It's just, I just want everybody to know, it's a lot of fucking money at 22 years old in 1981. Go ahead. All right, so I walk into Can't If It's General. So I take the job there because they offer me double and I see this guy and he's a rockstar guy. And how big is the brand Can't If It's General at this point in Wall Street?

It's a great middle-market guy, meaning he's not Goldman Sachs who mooring Stanley, but he's like the next level there. Right, it's respected. Yeah, and it's the number one bond firm in the world. Okay, so I go in there and I'm like a big swinger, and I think they love me, and I go see him, I'm a hot guy, come on, I got paid me double, they love me. And the guy says, listen, so they send me into the president's office, who I've never met before. So he sits me down and he goes, listen, we hired you, because we hate the other guy.

And we knew you were his pet. And we couldn't give a shit about you. Just get fuck out of my office. I love it. So I walk in like, I'm a big swagger. And I walk out like, he just steps on my face and push me like.

And I'm like, where can I? I've always thought, I've always thought from afar, and it's fun to say this to you now, that your life would be a real movie. I'm so pumped. I really hope that scene isn't it, because that's a fucking epic scene. Because my ego was so big. And then I'm like, literally a roadkill. Like, I'm the squirrel at the end. Like, I just got smashed. Actually, I want to make this learning moment for a lot of people. No bullshit. Don't hyperbolize it. If you don't remember, you don't remember. But I'm just curious. Real talk. How much did it crush you?

like for real, for real, kind of just for the afternoon, for a week, or did you say, you motherfucker, I'm gonna have your job. Like, how did you handle it? Actually, no bullshit. I was just, I was just crushed. Like, I had no, I didn't see it coming. You know, it was like, it was like, I'm like this, I got the view, I got the view, I got the view, and it just hits me, like right from here, in the side of the head, and I was like, why didn't you look that way? Like, I had no idea what's coming, I was like total, total like slam by a two by four in the head, and I was like wandering around, so.

I'm running around the firm. I felt like, what did I do? I got a Seinfeld episode. I'm walking around and I'm getting the Pinsky file. Nobody cares about me. I had to go find myself a job in the firm. Literally, I walked around the firm trying to find the job and they're paying me 40 grand. They don't give a crap about me. I know I'm going to get fired. I'm just going to get fired. They just wanted to just mess with the other guy and screw. They didn't care about me.

I was just dirt. Did you think about finding someone to latch onto, like a mentor, like a professor that saw you value in you? So this is the first lesson, okay? So you go into the trading floor, and the trading floor is just this vast, like football field with the people, okay? And I said, all right, what the hell am I gonna do? Like I'm lost, what the hell am I gonna do? So I said, all right, first lesson, find the winner on the floor, and no one's helping me.

Okay? So no, I can't ask them, who's the winner? Who's this or that? Find the winner on the floor. So I said, I start walking around and I'm watching. Okay? So I picked the guy. Real quick, I apologize Howard. Real quick, kids again, this is the blessing that you don't realize you have. There's unlimited free fucking content on the internet that will teach you absolutely everything. And now with AI, you can ask it and get it in a nanosecond.

This is literally an era where you have to like do what Howard's talking about. Like, now everything is at your fucking fingertips. Perfect. Can give you 97 answers. He could have DM'd a thousand firms and gone somewhere else. No, he had to literally walk around a fucking football field and just look at humans.

look at human beings and try to pick the winner. Okay, so then I try to pick who's the winners, right? Try to sense like who's the big dog in the room and who's the winner. And I walk up to him and I ask him. How long are you watching? Three days, two weeks, a month? No, no, no, no, no, because if I didn't have a job within 48 hours, I thought I was fired. That's what you thought. Yeah, cause this guy said, I don't give a crap about you. So you get, you're walking around in days for 30 minutes. You kind of calibrate. I better get a job. I better get a job. So I go in and I'm just looking and I find a guy who I think is a winner.

Okay, I just pick okay, that's a guy who's a winner because you can see other people are like gravitating to women something like that So they walk up to him and see what kind of coffee you like

I just get them coffee. I go out and I just get them coffee. Right? And then the first thing- Another fun thing kids, good news, coffee's really 12 cents back then. Like didn't have any of these fucking bullshit $7 fucking- No, no. It was black coffee 25 bucks. No, no, no. There's no downstairs. There's no downstairs. There's no Starbucks. No, no, no. It was 1980s coffee. I thought you went downstairs to the fucking

Coffee like vendor like the hot dog guy and gave him a quarter and brought him a fucking coffee. No, I went, I found the coffee over there. Yeah, it's catered for Cheryl's. Yeah, I just put a few different coffee machines. Okay, and then what I realized is some guys would treat me so I started doing that I picked like five people. I didn't know what to do and I just would get them coffee. Yeah, and I'd say look, I'll do whatever you want.

I'll do any chores you want, anything. Because I have nothing, right? I have nothing. So the only thing I have to give her is energy. 100%. That's all I have to give. So I'd say, look, you know, but you got to take care of me. And what some people would just walk by me the next day and they'd say, you know, black was sure. They thought I was a coffee guy. And so, and then I dropped that guy. Yeah. Because he thinks I'm the coffee guy. I'm not the coffee guy. He's not it. And then I found someone who I liked, okay? And he decided he liked me. So he said, he said, sit down.

Okay, then I had a job. He'd sit down, he'd sit sit down and then that was my job. Rick Chapman. Rick Chapman. Rick Chapman. Rick Chapman. And Rick Chapman. So, and here's what he did. He said... Where did Rick live?

Uh, actually in New Jersey. Because I mowed his lawn. Do you know what town? I'm a Jersey boy. I'm actually genuinely curious. I don't remember his town. Okay, no worries. Go ahead. So he's in Jersey. I mowed his lawn once. Because he said, if you mow his lawn, I'll do this for you. Because what happens is he became transactional. Yeah. Which is a fucking gift for you. Oh, it was everything. That was the greatest thing that ever fucking happened. Because what was I doing? I was buying an education in exchange for energy.

It's great. So I would mow his lawn. I'd pick up his dry cleaning and get his car washed. But what he did was he called his best client. And he said, you go get your young guy. Pick your favorite young guy. I'm going to bring my young guy. I'm going to go out to dinner. And he takes me out to dinner. And I tell you what, Rick, his client, when he was retired, called me up and said, you know, he sure could buy a steak.

Right? Because he's buying it on his, you know, remember, you had a great, you had a great expense account then. You got to like really nice restaurants by a really good wine. So he takes out me and a young guy. So the first nice restaurant, so you must have loved it. Oh yeah, loved it. But I knew, okay.

There's a 23-year-old on the other side. He's mine. Okay? I'm going to be his best friend. Love. Okay? I'm going to be his best friend. Of course. And I was just his best friend no matter what. Okay? No matter what. So I said to him, when you trade, someday you're going to trade because he's not a client. It was called Solomon Brothers was bought by Citibank. So it's part of Citibank. And they were the best traders in the world. I said, when you trade, you got to call me.

Just ask for me, just give me, and I'm his best friend, then I'm following him around, I'm buying beers, and on Saturday night and stuff, I just go out with him, I'm his bestie. And that's when I learned to cut the line. Because what happened is, on Solomon Brothers line, the top guy, Rick, he's got a Mercedes. The next guy's got a Chevy. The next guy's online, online, online, and when you went to Mercedes, you're gonna be 46.

Right? You're just online. And this guy's been retiring. You blow up, blow up. But I said to the 25 year old, call me. So he gets the, he gets the call to start trading. Right? And he picks up the phone to Kenneth Fitzgerald, which is the place to trade. He says, I want Howard. And this guy stands up and, and this giant trading floor goes, who the hell is Howard? And I'm like, me, me, I'm Howard.

And I literally go running across the trading floor, right? And pick up the phone for Peter Hirsch, okay? And Peter Hirsch does my first trade, and I just blew past this guy, and this guy, and this guy. I'm now second or third in line, right? Well, I should have a Chevy, right? And I'm on his phone trading with Peter Hirsch, because I worked him from the day I met him. He ends up becoming the boss of all trading at Sama Brothers.

because he was a winner. And that was lucky, right? But his favorite guy, he picked the favorite guy and I picked favorite guy. You're talking about the single variable of business that people don't talk enough about. I have 45 Peter Hershes. To your point of luck, I have 157 people that I thought were gonna be Peter Hirsch that didn't end up being Peter Hirsch. But net net, here's the news alert. You just need one or two, let alone 45. Correct. So I had, so.

I just worked it so that he introduced me and then that created me cut in the line. And other things I would do, I go to a, I go to a bar and I with my friends, right? So I'm, I'm well dressed cause I work on Wall Street and you go to a bar at night with your friends and I go to like brother Jimmy's, I've recited, right? It's like your feet stick. The barbecue, I know. Yeah. It feeds stick to the floor and I would walk around, find other people well dressed and ask them where they worked and buy them a beer. And, and, and my friends were like, what, what are you doing?

And I'd say, look, I don't know anybody. I need to meet people. I don't know anybody. So I meet a guy and he'd say, he's an advertising. Are there any friends who work on Wall Street? He goes, yeah, yeah, Chuck works on, yeah, he works at Goldman. He goes, hey, Chuck, this idiot wants to buy us a beer if you say a load of them. And I'm like, fine, I'll just buy him a beer.

So, one of those happened, I met one of those guys. He worked at Lehman Brothers. By the way, every firm I talk about, they're all like, I'm so old, they're all out of business, like every firm is coming up. Yeah, but I'm 48 and I know all these items, the firms. When I was building the wine business, these were all my customers.

So this guy works at Lehman Bros. And that company that these guys bought from Bernie Cantor, it's going public. And Bernie Cantor's really interested in it. And Lehman's doing the deal. So I asked my friend who I met at Brother Jimmy's, just buying him a beer. I said, can you get me the

that, you know, the early draft of the document, because my boss would really like to read it. He says, well, you know, it's, it's secret, but it's an early draft. I mean, it's not illegal around there. It's just an early draft. The company doesn't want you to see them undressed before they're ready and all, you know, set to go. And so he drops it off to me at six o'clock at night, says I just needed six a.m. in the morning. And I go to my, my boss is Bertie Kennedy's house. And I, and I give it to him. He goes, where did you get this? I go, I know people.

Who did I know? I knew the one guy. I met him at Brother Jimmy's, but I bought him a beer. And that's how, like, so Bernie Cantor thinks, oh, this kid, he knows people. He's working. You know, I was always working. Energy's the right answer, Howard. You know, it's funny. I don't use that word. But it's the answer, right? Like, when I think about that story from Cantor's angle, like, it's who I was and it's what I'm attracted to when I see it in others. It's not super

complicated. It's what coaches appreciate in athletes. It's just fucking life. Like effort is a fascinating variable in the game. It's just so goddamn obvious who fucking wants it.

Yeah, so people think you need to be really smart to be successful. And what I say is, you just need to be really clever. Yeah. OK? If you really clever. And I would argue that you can be successful. But I would say that's semantics, because what you're actually saying, I think, correct me if I'm wrong, and it's funny, I use clever a lot. I think you're talking about kind of like the way our, you know, we're in enough of a similar era. Like, we grew up, unlike the kids today, we're like, what college you went to and what your grades were.

were the binary indicator of your horsepower. And you and I grew up in a little bit of the... It's just totally wrong. Brother, can you do me a favor? Actually, I really want, this would make me happy. You were good at school, but can you grab that top? Can you grab that? Are you transcript? This is my, this is my report card. I just wanted to look at it while I say this and then we'll go back to you. Like, like, I...

It's bad. Yeah, show the ladies this suck. Yeah, look at the bottom. Look at my class rank. It depends on how it depends on how you define smart, right? Like, you know, for me, one of the things you could put it anywhere, one of the things that was very obvious about this, and I want every kid to hear this, people skills, man, if you could tell me, can I be great at memorizing shit for a test to get an A?

or have outrageous people skills, it's a fucking thousand to zero in the favor of people skills. It depends on what is smart. Clever to me is just slang for being smart about the actual shit that fucking matters. Humans, you're smart about people, which is what matters. So if you can get someone who's smart and clever,

then that's what a billionaire is. A billionaire just has both those things. They don't have, you can make huge amounts of money with one, and you're a professor with the other. If you're super smart, you're definitely a professor, okay? Because you're super, super, super smart, but you don't have the other parts. Have you had both? Oh, it's another one. Let's keep going on this story, because this is a lot of fun. Where is the next tipping point happen in your career?

an idiosyncrasier in my life, which is, I'm a reader, okay? I mean, I have to read the thing. I have to read the thing. It's now the bane of my existence. I mean, I can't sign the end of a document without reading every friggin word. It's probably why we're good at school, right? Because reading comprehension is such a variable in that game, and so you have very strong reading comprehension.

Yeah, really strong. That's like, if I listen to something or see something, I will never forget it. If I read it, it doesn't fucking even, I have none. So when I read it. I'm the reverse. When I read something, it- It like goes into- So the bad is in the document, it comes on me. Like it's in, it's physical. When I read it, it's physically on me. So like, I could be reading something and I'm angry. Like it's making me angry. And someone's looking at me going, why, why are you so angry? I go, you should see what this says. And they're like, what?

what it says, why would that make you angry? I'm like, so that's just the way it is. So, you know, so I, a friend of mine mentions something to me that there's this, there's this

railroad. And the railroad, when the United States of America was being built in 1897, the United States of America decided they wanted to industrialize the country. And it took, by eminent domain, it just took people's land and it brilliantly built the northern Pacific railroad that went from the Atlantic to the Pacific, and the southern Pacific railroad that went from the, right, and it just built railroads across the country. And I,

And the guy I mentioned, he goes, you know, this land is probably worth a fortune. So I go to the library and you do microfiche, which basically was like a negative and you put it on like a light box and you read it. I mean, now you just go to an iPad and look it up like this, but then you had to go dig it. So I dig up the deal and I find that all this land, Union Pacific Station, Philly, Union Pacific Station, San Francisco,

Chicago and all the mineral rights going all across Montana all the way through all this land is in this company called Burlington Northern and they got it for free and they issued a hundred and fifty million dollars worth of bonds and by the way you want to understand interest rates in 1897 they issued three percent bonds doing a hundred years and four percent bonds doing a hundred and fifty years so interest rates have been between three and four percent forever for friggin 130 years from people's oh aren't they so high you're like

Now, this is like ordinary. What about 1980 when you started your career? Oh, 12, 14, 16. So I go to Bernie Cannon. I walk into his office, right? So he doesn't really know me, right? But I'm like just doing this stuff. I'm 25. So still fucking early. Here's my idea. Here's my idea. We take over Burlington, Northern. It's about $4 billion. Okay. Then we sell the railroad.

Okay, for like three billion and we'll lose a billion. And then we'll have all this land that I, my genius 25 year old self, who has done absolutely no work and hasn't called a single freaking person. Okay, so I've no, I say this land is easily worth four billion dollars. Okay, because it's all this land, the middle of rights, four billion dollars. And we make three billion. What do you say? What do you think he says? Get the hell out of my office. I'm listening to you. So I keep

Every day I pound on him, and ultimately he gives me $2 million to invest. So I buy these bonds, interest rates are 12%, and I buy them for like 63 cents on the dollar, because 3% of you buy it cheaper, the math is you get your 12%. Okay, because you bought it cheaper and they go up in value over time, so whatever. So I buy $2 million with. But I'm not the only one who knows this.

The chairman of Burlington, Northern announces he's going to retire and he's going to take the land out of this trust, which I read about, okay? And he's going to put 300 million US treasuries in and take the land out, okay? But I read the documents.

And I know what the documents say. And I also, when I was planning this, I called all the bondholders. I knew every bondholder's name because I wanted to control the land to do this whole deal with Bernie Cantor that I made up on my own. And no video, so no one knows it's a 25-year-old making the calls, right? So then I say, you can't do it. So I call all the bondholders and I say, give me a proxy.

I hire a shithead lawyer. I don't know anybody. I hire some lawyer. And we write a snarky letter to Burlington, Norton, saying, you can't take the land. It's interesting. You just can't touch it. General counsel of Burlington, Norton, calls me on the phone. He says, what do you got? I got $2 million worth of bonds I bought at $0.63. He goes, all right, here's the deal. I'll give you $2 million. You keep your friggin' bonds. I want to take the land.

And then because you can put treasuries behind it, the bond's going to go up to $2.5 million. So I'm going to make $2.5 million in a $2 million investment in six months no risk. Double A bonds, no one's ever made any money in double A bonds. They move like a tortoise running across the street. You say, this baby's going to run across the street. Right? There's no money in it.

So I walk into Bernie Cannon's office. I said, now you believe me? I just need $2.5 million on a $2 million investment. In six months, no risk. They just paid for land. Now, to Bernie Cannon's credit, he says, all right, what do you think I should do? I said, they're going to split this land off this land's worth of fortune. I told you it's worth $4 billion. I'm still making it up. I stopped and called a single person. He gives me $100 million to invest.

He buys 100 million at Burlington Northern Stock. They announced they're gonna split the company into Burlington Northern, the railroad, and Burlington resources the land. DuPont comes in and pays $6 billion for the land. The stock goes up, doubles, right? As it's doubling, he sells as fast as he can, he makes $100 million, okay? And he gives me a bonus of $1 million, 25 is all.

My friends are like, he made 100 million, you only got a million? I'm like, what do you got? What do you got? What do you got again? $1250 bonus? I feel like I got a million dollars. I just need everybody understand. This is 1983 now, four. No, this is 86, I'm 25. Again, I'm just sad because money got weird because we just printed a fuckload of it in the last 20 years. And that's the answer, by the way. All inflation has come from printing. You just do not understand how much a million fucking dollars is in 1986.

Like, a hundred thousand a year in 1986 is profoundly wealthy. The way you think of someone who makes two to five million a year now. It is that big of a delta. You don't understand. That's insane. Can I say one thing to the three of you? I have bad news. I, like, actually am a businessman for a living and have a hard stop in 10 minutes. So I have bad news. We're going to have to do part two.

We're only at 20. How old are you? 25. No, no, right now. 63. Yeah, we're only at fucking 25. So fans, I know, I just want you to know there's going to be a part two. If I have to go somewhere, you come back because I want to keep this going, but I'm not going to be able to. So like, OK, go ahead. All right. So then we haven't even gotten to like, all right, anything yet. OK, but now everybody knows. But now it's going to be like fucking Star Wars. We're going to do three episodes. But now I'm a rock star.

A massive rock star. And it's 1986, too. So the Reagan thing's full effect. New York's out of control. It went from a shithole to really becoming what the precursor to what New York is now. You must be out of control.

Turn in, there's a stock market crash in 87. Right, October, Black today. Right, stock market crash in 87. Actually, I don't want to skip over that. See, you make this massive sitch in 86. You're like rolling now. You're like envisioning everything. Correct. World domination. How big of a, like, how much did you get fucked? Because you might have not, because it might have not been.

And so Black Friday, you weren't in a situation where that really destroyed you. No. But did it scare you of like, oh, wait a minute. It's not always just up, up, and up. I might, like, was that something you took note of? All right. So here's that. OK. So in April of 87. Of 87. Right. Because it happened in October. Interest rates. Interest rates start leaping.

They go about 100 basis points in 87, 1% up. And they're going up, up, up, up, up. And I'm thinking, this baby's going to crash. The market's going to crash. The stock market's going to crash. I go to everybody, say, short the market, short the market, short the market. And the firm won't let me short the market.

Who am I? I'm nobody. So they're not letting me do anything, right? So I can't do anything. So I start borrowing money from everybody I know to short the market. Jesus Christ. May, June, July, I borrow money from my grandfather, which is bad news if you can't pay him back. And I borrow from everybody, okay? And the market keeps going up. And you don't remember, but in August,

of 87, the market hits absolutely new highs. And I am absolutely completely and totally broken every way. All the money's gone, everything's gone. I bet it all, interest rates are flying. I'm saying this baby's going to crash and it's hitting new highs, new highs. And I am broke. And I borrowed money from everybody and shorted it. Stock market breaks in October.

All right, but that's the way the world works, right? It comes after you go broke. But one friend of mine, I borrowed money from him, and he was a stockbroker in California, and he bought options that matured at the end of October. And he hit. And it hit, and I earned enough money to pay everybody back, and I lost all mine. But imagine I borrowed 10,000 bucks from you, and I walk in after it crashes, and I go, I give you 10. You're like, oh, Howard, you killed it. Meanwhile, I had to go back to my grandfather and borrow money to pay rent.

And when you go to your grandfather and say, I need money to pay rent. And it's really painful. Because that million bucks you made in 1986, you invested it? I bet it. I bet it. I bet it, because it was definitely a break. And I was completely right. But the moral of that story is timing is everything. Timing is everything. So I was busted. But then I do another one in 1988, where interstate banking comes.

So a friend of mine tells me that interstate banking, outside, basically, you could only be a state. Remember, Citibank was New York City Bank. Citibank, yeah. Because you could only be in New York. That's right. Right? You could only be state by state. And then we're going to break that up. So Pennsylvania says, OK, we're going to let outsiders in in a year.

So I figure out, okay, why don't we buy a crappy, pensive baby bag that's got nice locations, it'll definitely get acquired. So I go to Bernie Canner, and I say, okay, here's my idea. And this time, he's messing around, he goes, all right, let's go, let's go. So it's now, it's 1988, he says, let's go. Not only does he put 100 million in, but he tells all his buddies.

Because when you're a rich guy, you want to do others. I get it. So he puts all his buddies in for $50 million. And we buy this company called First Pennsylvania. Six months later, it gets bought by Jordan National Bank for $12. We pay $6.00 for $12.00. Back in New York comes in right after Interstate Bank comes and buys for $18.00, $6.00, $12.00, $18.00. We go up straight up, triples his money. He makes $300.00. But you put up $100.00. He gets $300.00. He's a profit at $200.00. Guess what he gives me?

Two bucks. And now I got money again. He's back. I got money back. So basically, I got money again. All right, I got money again. And now, okay.

He liked me the first time I made him money. He loved you the second time. That's right. He's loving me. Okay, now, whatever. I'm very aware why Steve Ross likes me. When you start putting up more than one win, it matters. That's what happens. That's right. Now he loves me and now it's 1988 and now I'm on fire in the firm. So I'm managing his money, I'm managing all his friends' money. You're on fire. Doing every bet I want. I'm making my income starts to double.

Okay, so if you look back at me at the beginning with 40 grand, then I made 80 grand, then I made 160 grand, 320, 650, a million three. Now, if you keep going, you know, if you double and double and double. So now I'm making like my normal job of making millions a year, millions a year, plus I did this for this extra. And Bernie counters in love with me, right? He's in love with me. How is Bernie at this time?

So he dies in 1996 at 79. So he's in his mid-70s. He's in mid-70s, and he's in love with me. I had to come like his, I'm totally, now I'm not the kitchen cabinet, right? 1991, he fires the president of the company, the guy who told me, you wrote a kill? Oh, no way, that dude. Yeah, and he says, and he promotes me at the age of 29, I become the president of the company. Wow.

So I'm the president of the company. We're growing. The company's on fire. It's growing. It's rocking. And then 1986, right? So the deal is in the company is I hire everybody. Like it's like, you're hiring everybody and everyone says, OK, what happens if something happens to Bernie? You know, Bernie counters like the owner or what happens. And it's like, I control the company if something happens to him. And so if he dies, it's me and you'd say, cool. All right, you're hiring me. I'm cool with that.

He goes on life support and his wife decides he's going to try to sell the company. And so we have a giant fight. And I go to my lawyer, what do we do? He goes, let's not snatch the feet from the jaws of victory. You have a straight flush. Just do nothing. She hires Kex, this big PR company, and

I get a call on Friday night. We have a big court date coming. And on Friday night, I get a call from the New York Times, this woman named Diana Enriquez. And she says, listen, I've been working with kexts for three weeks. And I'm going to write the rip in this story that you're an asshole. And do you want to talk to me or not? You're the cover of Sunday's New York Times Business section. What year is this? 89? This is, no, no. Now we're all the way up to 96.

Just so everybody knows, even though the internet is out in 96, like it's the 1996 internet, which is like, it's still fairly small. And like this business, like this is the punchline of the, like every single person of any kind of anything in the business universe in the world, let alone America, reads the Sunday business section. This is a big deal.

Right. So I decide, you know what? Screw it. I'll talk to her. Smart. So I sit down with her and talk to her and she writes a story with partners like these who needs rivals, right? Her picture, my picture, Bernie Cantor's picture, like gigantic means on life support. Yep. Anyway, I win the case in every possible way. And I buy a wrap. And then my son is six days old.

Okay, and I hold them up in Delaware. I'm in Delaware where we settle and I buy her out and it's over. The company is now my company, forever, forever. It's my company and I hold my new son up. Like Simba. And I'm like, hey, good one. You know, like, you know, that's it. And I'm like, you have now, I look at my little boy and I say six days old, like you have no idea what a good day you just had. You love these. You just did it. And so then that was the day the firm was mine.

Okay? And then I went and hired everybody we loved. Because the rule was, if it's my firm, I'm only going to work with people that we like. That's the rule of company. I make that the rule of the company and we work with everybody we like. So, I say it this way. We all have the same rainbow of friends. Now, think about your friends. Think about this side, smart, capable, you know the winners. And the ones on this side, crazy, make you laugh at a ball harder than anybody else, but you know, a little... And I'd say, just hire these.

And that's my firm. We hire so my brother joins my best friend joins my my college roommates brother went to Harvard Business School. He runs banking everybody I hire everybody I love but I make that the rule not for me Of course everybody so every the security guard hires so I don't have to worry about them You know if one of them has to go to a wedding the other guy fills in you don't just Family business. That's the firm family that's located on the hundred first to the hundred and fifth floor of the World Trade Center

You're playing at some fucking building. You know my friends get killed. It was my brother, he's 36. It was my best friend. He's 39 and I was my best friend's brother.

Everybody, everybody loses everybody. Everybody loses everybody. Everybody loses everybody. He's like, look at this office, right? And say, okay, everybody dies. Okay, and you're taking, I was taking my son's first day at kindergarten. That's it. That same son, I'm in his first day at kindergarten. So I race to the building. I race to the building. And I get to the door of the building, right? Cause I'm just trying to grant people. What time did you go to the office prior to first day? 30. Yeah.

The show is on, all right? Your show is on, okay? At 848, the show is on. Everybody matters. On September 11th, he's in the office. It's not a holiday. There's no reason to be out. Everybody's there. It was my first day at kindergarten for horseman. My best friend, Doug, his kid goes to Riverdale and he dies because it's not his first day of school. Everybody dies. Everybody's dead.

And I get to the building. I head right to the building right away. My phone keeps ringing. As it turns out, my phone kept ringing. I could pick it up as a flip phone. And there was no connection. It was my brother calling. So I get my sister on the phone when I'm going downtown, because someone, they tell me a plane hit the building. But I don't know. I haven't seen it. They just had a plane at the building. I figured it's like some stupid Piper Cub, some guy clipped the building or idiot.

So I tell my driver, I said, just go to Fifth Avenue. Because you can see, I know you can see the building as soon as, and there's just flames, just smoke, just pouring out of the place. And he starts crying. I said, let's just get there. Let's just get there. And I get my sister on the phone. And she said, I spoke to Gary, my brother. And I said, what did he say? She goes, I got him on the phone. And he called. And I said, well, thank God you're not there. He goes, I am there. I'm calling to say goodbye. I'm going to die.

Smoke's pouring in. There's no way out. There's nowhere to go. I'm just saying goodbye. I got to die. I tried to call Howard. I can't get through it. I'm just telling my love him. I'm sorry. That's it. That's it. So, so I, so I just go to the building and I'm just hoping people can get out. I'm just hoping some way there's people to get out. But I know they're all in there and I know there's nothing they can do. And then I'm standing at the doorway of the building and I'm grabbing people, asking them what floor they came on.

You know, in the highest floor I get to, it's like 90, 92. And then I hit his sound, this loudest sound I've ever heard in my life. It's like Titanic. Remember the movie when it breaks in half? That's the sound. I don't know what the hell's going on. So I start running. I got my suit and tie on, right? My shoes on it. And I'm running. As hard as I can from nothing. I have no idea what's going on. I'm just running my ass off.

And I look over my shoulder and a black tornado is chasing me. You saw that smoke sort of rolling. And I'm running as hard as I can. And this tornado is chasing me. And then the tornado comes across this way. And I see the tornado come and say, dive under a car. And I hold my eye like this. And it just goes whoosh. And then the world is black and silent.

I didn't, I'm not clever enough to put something over my mouth. I have no idea what's going on. I'm thinking son of a bitch. I was uptown and I was safe and I'm going to die. I'm going to die because it's a thing about it. It's black and I'm holding my breath. I'm like, I can't believe I'm going to die. I said, actually, I can't hear any sound. I'm dead.

I can't hear any noise. I'm outside. It's dead silent. So I take my fingers and I go like this. Because I can't see. My eyes are open and it's black. And I stand myself in the eyes. I'm like, ah, ssss. I go, OK, OK.

But I'm alive. So I stand up. Of course, I'm hiding under a car, smashed a little bit out of my head. Now I'm bleeding off the side of my head, self-inflicted. So I climb out from under the car and I get up and it's pitch black. So what's the first thing I do? I start running. But of course, I'm running pitch black. So what do I hit? Park car. I go flying off the park car. So now I'm bleeding, I'm limping, but all self-induced. And then I realize,

So now I'm walking like this, in the dark. And then I see a flashlight. So I walk to the flashlight. And there's a cop holding the flashlight. Just holding up like this. So I put my hand on the back of his collar. And so let's get the hell out of here. And he sits down.

He just sits down, because he's in shock, because the thing went right through him. And so I said, give me that. So I grabbed the flashlight out of the guy's hand. And now I'm walking in my flashlight. I find a, like a, I think it was like a coffee republic, you know, some coffee shop that's blown to some of the reins. And I go in and I find a bottle of water. And there's a paper towels. So I take the paper towels. And then I put the paper towels under my arm. So I got the giant flashlight. Got the paper towels. Right? I got a bottle of water. I start walking.

As the smoke starts to clear, it gets lower and lower and lower. My driver jumps on me from behind me. He's like, Mr. Levitt, you're alive. You're alive. I can't believe you're alive. Because he was a retired detective. And he goes, you're alive. And I turn around. He goes, where do they give rich people like flashlights and water? And he's like, who gets flashlights and water? Like, where did you get this stuff? And then we walked up town. And we just walked up town, knowing that they were all dead.

Well, I'm sure everybody was moved as much as everybody in this room. I really beg that we can do part two of this. Sure. And I thank you. Thanks, man. I hope you all enjoy this episode. Make sure you come back tomorrow to listen to the second part of this incredible conversation. Enjoy.