Right, exactly. So I experienced that, and then I was the kid with the funny accent over there. I got bullied a little bit, so I had to deal with some of that. Being a tough kid, a tough kid. And then when I came back, my mom literally decided she was too young—didn’t want to be a mom—and that stuff happens. So they split up. My dad came back to the States with my sister and me, which means I didn’t have another younger sister, and we started over at my grandparents’ house in the south side of Chicago. As the kid with the funny accent, I had to be tough and defend that funny accent.
So I became this tough street kid, and then my dad remarries. Fast forward a little bit—I lined up in Northwest Indiana, which is a suburb of Gary, Indiana, which is a nut. It’s right next to Chicago, so it’s again just tough parts. I grew up as a street kid trying to save myself and my friends from street life, which meant drugs, gangs, and street fights. It was a very tough growing-up environment, but I learned I was fortunate. This is what I wrote my book on: I literally learned that if you want to get out of a bad situation or move forward, you want to connect yourself with better people. And so my dad was always hustling, and at night he was going to school to be a school teacher—because he was in industry and he was burned out on that, and my new mom was a school teacher. I was exposed to a lot of education, a lot of teaching. My dad was always selling stuff. You know what network marketing is, right? My dad was one of the top guys—or became one of the top guys in the country for Shackley, which has been around since the ’70s. In the ’70s, he was selling tons of Shaklee in our garage, and our bedrooms were filled with product boxes because you had to inventory stuff. There was no consignment. I learned how to sell. He was doing networking events in our house. And it was funny because all these shipments were coming in and out, and then my parents in this lower middle-class neighborhood in Hammond literally had shipments coming in and out, but then they got new cars because they were selling so much.
My friends thought my parents were drug dealers, because they were sort of selling different kinds of drugs, but legally. My dad was always about connecting, connecting, connecting. I was about 13 years old. Fast forward some more, and then we’d go into this restaurant that was a treat. When you own some restaurants, you get regulars in there for sure. You take care of those regulars, and they bring people because they’re regulars, and the word travels. We were regulars in this fine dining steakhouse, and the guy who owned the restaurant had our booth on Saturday nights, and our waitress and our dining room, and the owner would pass by and buy my parents a cocktail from time to time.
After a few years, I’m 13, and all of a sudden I’m like, “Hey, I want to work here.” My dad’s like, “You’re not old enough. You gotta get a work permit.” And he goes, “But just ask Mr. Freddie; maybe he’s got something you could do.” So I go up to Mr. Freddy because he always had wads of cash. When you empty the registers, go to the office, put it in the safe, and count the dough, I’m like a street kid thinking, “That’s the life for me in this business.”
Yeah, if I work in this business, I can legally have wads of cash. So anyway, I go up to Mr. Freddie, and he’s this big dude. He’s like, “Yes, young man.” And I’m like, “Mr. Freddie, can I work here?” And he goes, “Well, how old are you?” And I go, “Well, I’m almost 15.” Now I’m 13, and at the time he’s like, “Well, how long until you’re 15?” I go, “Well, about a year and a half.” He goes, “You look pretty. You look old enough. Come in on Saturday. We’ll get you some work.” So then all of a sudden, next thing you know, he’s figuring out how to pay me. I become a busboy, and I meet all these business guys. It’s a business steakhouse, and during the day and in the evening, I loved working the bar because all the business guys came in, they were networking, and I saw patterns of people connecting—the who’s who, and politicians, and all this stuff happening.
And so all of a sudden, I just got to learn how to connect, and you’ll appreciate this. There was a guy in there who owned a couple of companies—he was a limo guy and everything else—and he was always connecting with people. Fast forward—I was 15, but I had no driver’s license. I was 15 or 16, and I said, “Hey, what would it take for me to get a limo? Because I want to impress this girl, Jill, for the church carnival.” He goes, “Well, come in on Sunday, you can watch some limos. And if you can scrape up between what I give you and the dough that you make, you can have a limo for 65 bucks.” And so I go for four hours on a Tuesday or Wednesday night, or whatever it was—it was an off night for them.
So here I am, in middle school, and all of a sudden this limo pulls up, and my dad’s like—well, think about all my friends, right? So they see my parents—let alone with packaging and a new car—and now all of a sudden, a limo shows up to pick me up. It’s like, “What’s going on?”
I go, “Charlie, help me get a limo for today to take Jill on a date.” It was just one of these funny things where I learned how to connect, and I wanted side jobs and gigs and things like that.
Eventually, I met the CEO of Merrill Lynch, and I’m fascinated by computers, and he became a regular in the dining room. I talked to him, hung out, and helped him throw parties. And back in the day—before you were a kid in the ’70s—they had these big stereo rooms, ginormous speakers, reel-to-reel, and people would sit in stereo rooms and just jam out. So I’m sitting in a stereo room with the CEO of Merrill Lynch, and I’m like, “Mr. Bradley,” and he’s like, “Yes, Dean, it’s about three in the morning. Imagine, Merrill Lynch, three in the morning.” All of a sudden, I look and I’m like, “Hey, what would it take for me to work at the Board of Trade on all those computers you guys are working on?”
About as innocent of an ask you can make. He looks at me—I’m sort of nervous asking this question because I’m going to school for hotel restaurant management, not computers. And he looks at me and says, “Dean, you can start in two weeks. I like you. I trust you. You’re a hard worker. You’re a good man; you can start in two weeks.” So now I’m really scared—I’m going to college. I’m a sophomore in college by this point when I’m making the ask. I’m switching my entire career, my life. Next thing you know, I’m in Chicago, just learning the power of connecting—the network—but more importantly, the power of asking, putting yourself in the game, in the equation, even if you’re scared. Just asking for things has always been two big lifelong things that I’ve always built from.