True Signs You're a Winner or LOSER | Kevin O'Leary

I can sit in a room with somebody for 15 minutes and know if I've got a winner or not, and 99% of the time I'm right. So, I listen to the gut, and I listen to the person, I listen to the plan. I know it's gonna work or it isn't; I just know I'm that good. Well, you know, like the serendipitous. I really believe that, and how will the outcome occurs is, you know, everybody has a path in their career they plan on, but it generally doesn't work out that way. There's a series of events that happen to you along the way, and you don't know as they're happening because you've only realized how important they were maybe a decade later when you realize it was a huge pivot point for you.

Mine was when I was working in a summer job in college for a pet food company, and I had a German manager, a really interesting guy. He taught me that most pet foods at that time were made from Sea of Japan tuna and chicken faces and beef lips and rendered, you know, protein using mango juice to crush it up. Sounds horrific, but those are two basic engines, and then they'd add some peas or, you know, some carrots, and they'd create cat food flavors. Decades later, when I was in the software industry, I realized that, you know, we were the leader in math and reading software, and here's where this story comes into play. All my competitors were spending a fortune building unique applications to advance reading and math scores. Those are the two big things you actually create software to advance if you're in education.

I thought to myself, that's crazy! This is really just Sea of Japan tuna and chicken faces. All we need are two engines, and we'll just add characters to them, and that was how the learning company became the largest software company in the world in reference to education. We sold over 4.2 billion, but that manager gave me the idea to synergize around two development groups. We hired, you know, we buy a company, fire everybody, and just take the characters they had, and we cut our costs dramatically. You know, our cost of R&D was half the industries. Everybody was complaining, but how were we doing it? We were doing it because we understand that that software is no different than that.

That's amazing. It also sounds, and I want to dig deeper into this: like, what you're good at. It sounds like you're really good at identifying patterns. It sounds like, you know, that was a model or template that you used, but also a pattern. Before you go into that, I want to go back in time a little bit to young Kevin. Yeah, yeah. I want to talk about, you know, your early origins, your influences, like what did you want to be when you grew up as a young kid? What were you thinking about?

What happened is around that time my father was only 37 years old, died, and so that was a very traumatic moment. My mother remarried about two years later, and my new father was a completely different character than my biological one. He was finishing off his master's, or then his PhD, at the University of Illinois Champaign-Urbana, and he joined the United Nations. We started moving every two years to a different country. So, I've lived in Cyprus, Cambodia, Tunisia, Ethiopia, Japan, England, Switzerland, every 24 months. I mean, I met, you know, Paul Pott while he was a lieutenant for C anoke in Cambodia. I've met Haile Selassie and his lion cubs before I became a deity. These are just random outcomes in my life, but it's certainly later, as I always say, you don't know these things are happening to you, but they are for a reason.

It may have made me a relatively successful international investor because I was able to see trends. I mean, I lived in Cambodia. I saw when the French and Germans were going into real estate there to follow them in. I knew exactly what the industries were in Ethiopia and what you should invest in. Cyprus, I already saw the banking system and the oil business growing there, and I was an investor there. So, there's all kinds of cues you get from your youth that you should really apply to your business later, and that was a remarkable experience. Certainly, he was a major influence in my life because when I graduated from high school, I wanted to be a photographer. I was really into photography, and I had my own lab downstairs. I was doing all the things I loved to do, and he said, "You're not good enough! You're not good enough to be a photographer, and you'll starve to death. You should go to college and get a degree."

I listened to his advice because I thought he really understood. I went on to do an MBA, which ended up being a very important tool for me later. But I went back into production. My first company was Special Event Television, which produced all the programming for the East Coast Hockey feeds: Bobby Orr, the hockey legend, Don Cherry's Grapevine. We would shoot it all week, much like we're doing right now, and then edit it and send it up to a satellite in the mid-80s. I was an editor, or a producer, or a cameraman. I used to work with Nagra's, and we had a Steenbeck editing table. I did it all, and I was trying to get back to the thing I loved, which was photography and production, and make money doing it. There was that science and that art coming together in my life.

We sold that company because Don Cherry's Grapevine became a very successful television format, and that was my first transaction. We sold the company, and the three founders took that money and started the software business that eventually got sold for 4.2 billion. Things happen in life; you don't know why, and you only get to look at them in retrospect a long time later. But all of that stuff, you know, made me what I am today: the good, the bad, and the ugly, and I wouldn't change a thing.

What I pulled out from that, as well, is it seems like all that moving and all that, you know, uprooting and going somewhere else you had to sort of adapt or die, right? Like you had to really sort of... I think it's a Bruce Lee quote, right? Like, "You know you have to be like the water in the vase, you know, not the vase; you have to conform to whatever shape that you are poured into." It sounds like that's kind of what you did, and also it sounds like that experience made you very scrappy or resourceful, right? Like, so you're battling with dyslexia; you're also, you know, dealing with probably different cultures and different foods and different languages. You had to be resourceful and creative and, you know, be that water.

Yeah, yeah, that's a very intuitive way to look at it, and you're right. I didn't like living in places like Cambodia, Phnom Penh. I didn't want to be sequestered with the expats. That was not interesting for me. I wanted to live with the people. We ended up with a couple of tutors. We used the Calven system, then, which is a system that is a direct mail learning system, and better than nothing, right? Try to stay advanced in high school years. But Tia and Dang were a couple of, you know, people in my life then that were very influential. I had a French tutor; she was from France. She spoke a little English, and she tutored me, you know, at home, and in where we lived in Cambodia. I slowly got immersed in that culture, which is a beautiful culture. Cambodian people are almost mystical, and they're beautiful. I didn't want to hang out with everybody from Chef Cabana; I wanted to hang out with the Cambodians.

That's what happened. I took my kids back there a couple of years ago to show them where I grew up and to take them into the jungle and see how Cambodia works. That was a unique experience for them; they were blown away. They've never even thought about it. So, to me, it's all those experiences. And I certainly, in Cyprus, hung out with Cypriots. You know, in Ethiopia, the Ethiopians are the most remarkable people because you're living a mile high. They're very tall, very lanky; they're beautiful. They obviously win almost all the marathons they get involved in. So, I got into that. I didn't have a bicycle; I rode a horse. I mean, the first barbecue I ever did with my family and friends, the sky turned black with vultures. They'd never smelled burning meat before that way.

We had a thousand vultures circling, and I looked up and, oh shit, what's happening here? That was the kind of thing you learned. Just I was showing these guys, "Here's how you have a cookout; here's a barbecue," and they said, "We don't think it's a very good idea." I think now, you know, it's a great resource for me in what, as you say, you're thinking about how to do things a little differently, particularly in global businesses. I'm involved in global financial services now. I just came back from Dubai last week in Manila. You know, I feel very comfortable going to those countries. I've been there before. There's nothing new or mystical about it for me, and I think people feel that in you, and they appreciate it.

I would agree with that, and I think that's a really good lesson. I want to just underscore for the people who are watching. I know a lot of them work internationally; unfortunately, I think a majority of the tendency, you know, we go to a country, and we just sort of snowplow there, culturally. We ask them to speak our language, and big mistake. It's a big mistake. Yeah, yeah, but just, you know, culturally, I think traveling internationally really rounds you out, right?

Yeah, and I've done a little bit of travel myself, and just being in a different country, you realize, oh, there are different ways to do things. Yep, and they are good. Yeah, and they also, if you respect their culture and then you can make reference to your history, and they appreciate. You know, when I go to Cyprus, people knew I went to the British school there, and then I went to the Cypriot school there, and I know the street names. I know where Family Gusta is in Carini and the beaches and Tzoneus and all the places where the current population hangs out. I've been there. I've been going there for 30 years. That is a huge financial hub. People don't realize how big and how many transactions occur in the Cypriot banking system because that's where sort of the East meets the West. Russians are very active there; there's a ton of capital for the Middle East there. It's sort of like a neutral ground but a very important place to have relationships.

Yeah, I know the good lesson. I mean, you know, when you show respect, you get respect, and I'm sure that's a big part of your success. I often ask my guests, you know, how do you know what you're good at? How do you know where to find your passion? Because, you know, the sort of the default advice is follow your passion, and that may or may not be good advice. But I think the point that you sort of crystallized for me is sometimes you have to do stuff that you don't like doing to figure out what you do like.

That's a great point. That's an absolutely great point, and you want to do that early in your career to understand what motivates you in the perfect situation. I mean, I tell entrepreneurs today. I invest in so many of them. You know, when I say to them, “Look, you’re starting this journey; I want you to understand something: this is not going to be fun all the time. You’re gonna work twenty-five hours a day, eight days a week because there’s some guy in Mumbai or Shanghai that’s gonna kick your ass if you don’t. And it’s forever, and it’s forever.”

But what will happen if you’re successful, and you won’t see it coming? You wake up one day and say, “Oh my goodness! I’m wealthy beyond my wildest dreams.” You’ll probably go right back to work. But the point is, you created something of tremendous value, and the way it manifests itself to you later in life is it gives you freedom to do whatever you want. My number one message to entrepreneurs that I teach today is: never pursue entrepreneurship for the greed of money. It has nothing to do with it at all. The whole reason to be an entrepreneur is the pursuit of freedom. That’s why you do it. You do it because you want to be free one day to do whatever you like. I’m here because I want to be here. I don’t have to be here. I don’t have to ever listen to a phone call again if I don’t want to.

That’s not what I want to do. I enjoy spending my time doing the things that I want to do, and I deserve it because I worked like hell to get here. I’m a huge, you know, advocate of capitalism. I defend entrepreneurship every day. When people say, “You don’t deserve that,” I say, “Fuck, I deserve everything because I started with this. Everything I have, I created myself, and I deserve what I have.” I feel ferociously about that, and I tell other entrepreneurs: do not be embarrassed about success; wear it, own it; it’s yours, and you deserve it.