In Search Of Excellence - Kevin O'Leary: Business Is War | E12

Episode Date: November 16, 2021

Randall Kaplan is joined by serial entrepreneur and media personality Kevin O’Leary.  Known to many as Mr. Wonderful on SharkTank, Kevin talks about how his unique life experiences made him the suc...cessful entrepreneur and investor he is today.  In this episode, Kevin and Randall talk about Kevin’s upbringing and what Kevin learned from his mother about financial independence and investing.  Kevin shares stories about the moment he knew he needed to work for himself, the greatest lesson he learned in business school, and his first entrepreneurial success.  Kevin also talks about why culture matters in business, entrepreneurship and investment strategy, and much more.  Topics Include: Growing up with an alcoholic father.How Kevin’s childhood experience informed how he thinks about investing.  When he decided to become an entrepreneur.  His first success as an entrepreneur.  Overcoming dyslexia and education.  Investment strategy and entrepreneurship.  The war of business.  What he learned as an intern at Nabisco.  Women in finance and investment.  Cryptocurrency, decentralized finance, and NFTs.  The value of failing as an entrepreneur.  And other topics...Kevin O’Leary is a serial entrepreneur, best-selling author, and investor.  Kevin was a co-founder of Softkey Software Products (later The Learning Company) which Mattel bought for $4.2 billion1999.  Today he leads the O’Leary Financial Group, including O’Leary Funds, O’Shares EFTs, O’Leary Publishing, and O’Leary Ventures.  He is also the founder and Chief Sommelier of O’Leary Fine Wines. Kevin is fondly known as “Mr. Wonderful” on ABC’s Shark Tank, is the host of the CNBC show Money Court, and is also a host and personality on Discovery’s Project Earth and CBC’s Dragons’ Den.  Kevin’s is also the author of three best-selling books about financial literacy.Resources Mentioned:nft.comSponsors:Sandee | Bliss: BeachesWant to Connect? Reach out to us online!Website | Instagram | LinkedIn

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Starting point is 00:00:00 I believe that what works and what makes someone an entrepreneur is a burning desire to be free, that no one can tell you what to do. The only way you're going to get there is through entrepreneurship. It's not about the greed of money. The motivation they have is that to pursue personal freedom. Welcome to In Search of Excellence, which is about our quest for greatness and our desire to be the very best we can be. To learn, educate, and motivate ourselves to live up to our highest potential. It's about planning for excellence and how we achieve excellence through incredibly hard
Starting point is 00:00:36 work, dedication, and perseverance. It's about believing in ourselves and the ability to overcome the many obstacles we all face along the way on our way there. Achieving excellence is our goal and it's never easy to do. We all have different backgrounds, personalities, and surroundings, and we all have different routes on how we hope and want to get there. Today, my guest is Kevin O'Leary. Kevin is an incredibly successful serial entrepreneur and investor. He was a co-founder of SoftKey Software Products, an educational kids' software company, which ultimately became the learning company in which Mattel bought for $4.2 billion in 1999. Since then, he has successfully co-founded, funded,
Starting point is 00:01:16 and sold many companies. Among other ventures, Kevin is the founder of O'Leary Funds, an investment fund company, the founder and CEO of O'Leary Financial Group, the founder and CEO of O'Leary Ventures, and the founder of O'Leary Fine Wines. For the last 13 years, he's been on the amazing TV show Shark Tank, where he's universally known as Mr. Wonderful. He is the host of the CNBC show Money Court and is an avid guitarist and photographer and is the author of three best-selling books about financial literacy.
Starting point is 00:01:47 Kevin, thanks for being here today and welcome to In Search of Excellence. Thank you very much. Great to be here. I always start my podcast with our family because from the moment we're born, our family helps shape our personality, our values, and the preparation for our future. You grew up in a middle-class family in the town of Mont Roya, Quebec, a suburb outside of Quebec. I want to talk about your parents separately, and we'll start with your dad. He was an alcoholic, and his alcoholism ultimately caused your parents to divorce, and he died when you were seven years old. Can you tell us what
Starting point is 00:02:19 that was like and how his alcoholism and his death at a young age for you influenced your childhood and your future? Yeah, it's an unfortunate situation. My mother is a descendant from Lebanese family and my father was Irish and he was a gregarious salesman. And they met in my grandfather's company called Kitty's Togs. And it was unfortunate that he was a difficult man to live with, obviously. Alcoholism has its issues. I think he loved his kids. I believe that. But they ultimately separated. And while he was alive, and I think he was very lonely at that point, and he died at a very young age at 37 years old. So that was very traumatic, obviously. My mother was trying to obtain custody, and she, in fact, had to go to Europe with us to leave the country. And we traveled around Europe
Starting point is 00:03:12 for almost a year, going through the legal process of separation, which was an extraordinary experience for me. I mean, I went to all those countries at a young age, and ultimately she remarried, basically fathered me the rest of my life. He's still alive. They ultimately settled in Geneva, Switzerland. But during the journey, my stepfather, George, became a member of the International Labor Organization, the ILO, and he was an expert in infrastructure. And so the ILO would go do projects in multiple countries, and he'd get two-year stints in each one. So I've lived in Cyprus, Cambodia, Tunisia, Ethiopia, Japan, Germany, Switzerland, France, you name it, I've been there.
Starting point is 00:03:52 And went through all those different educational experiences in different schools. I met some extraordinary people. I met Paul Pott. I met Hailey Selassie. I met Sianouk. I met them all because they were part of the international community. The expats would often mingle with the government quite often. And so that was a really incredible experience for me that I didn't realize was happening at the time. I thought everybody lived that way. And that's what you do when you're a child. You assume that
Starting point is 00:04:20 everybody's growing up the same way. But looking back, it really formed how I think about investing, how I think about other people, how I think about other cultures, and indeed the way I invest and travel today. So let's talk about your mom, Georgette. She was a small business owner. She came from a family of merchants. What kind of values did she teach you and how did they affect your future? She believed in personal financial independence. She really, really believed that because she felt helpless during the divorce period. And that really changed her view of the way she was going to manage her life and her own money and her own destiny and her own investing. And she became a great teacher to me about how important it is to take care of yourself and make sure that you're safe and that you can then take
Starting point is 00:05:11 care of others around you. And she became sort of the matriarch of her sisters and indeed the whole family. She was a very pragmatic, disciplined woman about money. She was very, very liberal in her thinking, which is completely different than I am. And yet she was a great matriarch. So politically, we didn't agree on anything, but around business and family values, she was very strong in that respect. And she always believed in charity and she had a great idea of karma. And she'd always say, look, two things. If you talk about money and you brag about money, one day you won't have any money. And also, you have to give back. If you're successful, karma will get you if you don't give back. And I've lived by those
Starting point is 00:05:56 mantras as she taught them to me when I was a teenager. My dog's name is Karma, and I believe in karma. So we share that in common. She also taught you about the value of saving. Let's talk about that and food and exercising at a young age. Yeah. She really believed that you need balance in your life, that you really have to figure out how to live well, take care of yourself. And above all, you've got to take, in her case, she believed in taking 20% of her income and investing it. I knew this after she passed away because I always wondered where she got all this money from to take care of my brother and I and her extended family members. She, at a very early age, in her early 20s, took 20% of her paycheck and invested in the S&P 500 for 50% of it,
Starting point is 00:06:47 and a bunch of telco bonds, bonds of telephone companies, because she believed people would turn their heat off before they'd cut off their communications. And so she owned all these bonds her whole life for almost 50 years. In those days, you were making 6% and 7%. And I found this out because upon her passing, the executor called me and said, you've got to come down here. Your mother died a very wealthy woman. And you're the executor. You're the older brother. And I said, that's not possible. She had basically hidden her account from all of her husbands her whole life. It was in her name. And I looked at the portfolio. She was not a stock analyst, but she had amassed a fortune by simply
Starting point is 00:07:25 only spending the dividends and the interest on the bonds and letting the rest continually compound for 52 years. And I was stunned. And it hit me right there that changed my investment philosophy forever. The idea of putting something aside and only spending within your means of your income. It was stunning. And I called my brother up and said, you're not going to believe this, Shane. You're just not going to believe this. As the executor, I dispersed the money to extended family members and it's still around. I mean, my goodness, what a lesson that was for me. And it was after her passing, she taught me something in death. When our company went public, I went and I made the rounds of all the money management firms, Goldman and all the
Starting point is 00:08:05 other firms. So I'm sitting there with a Goldman partner in the financial management group. And he asked me a question, you start with a penny one day, and it doubles each day in a 31 day month, how much do you have at the end of the month? And the answer, and it's a question that I like to give people, I think there's only three people of the hundreds who have gotten the answer, and it's a question that I like to give people, I think there's only three people of the hundreds who have gotten the answer right, is two to the 30th power, which ends up to be $10.6 million. People are astonished when I tell them that. And the lesson there is the value of compounding. And I think it's important for our younger and even the older listeners and viewers to note, you don't have to be wealthy to save.
Starting point is 00:08:48 And if you save and your money compounds over the long term, that is the key. Compounding is the key to financial freedom. Yeah, I totally agree with that. It's geometric growth of wealth. That's what's going on there. Let's switch gears and talk about your childhood and your teenage years. What were you like as a kid? Were you popular? Were you a leader? And what did you do for fun? I had a different childhood because I was in a different country every 24 months.
Starting point is 00:09:17 And so I'd have to remake friends. And some of these people that I met in those years are some of my closest friends today from multiple countries. But we would roll into town, didn't know anybody, find a place to live in places like Addis Ababa, Ethiopia. And in Addis Ababa, we were in an expat community, lots of different people from different countries living there, servicing the United Nations or the military or whatever. And for an example there, there were no bicycles. We rode horses. We rode horses in the open plains of Ethiopia. And I just thought that was normal. And it was incredible. I remember the first time I ever put a barbecue out when we arrived there. And I remember specifically, it was December of 1969. I remember that because the White Beatles album had come out and I received that for Christmas that year. And I went outside and lit up the fire and put a couple of hamburgers out. In about five minutes, the sky blackened with giant vultures circling, massive birds, prehistoric looking, shuddering the sun from me. Those are the kind of images I remember of extraordinary
Starting point is 00:10:26 outcomes of living in countries like that. You do not barbecue in Addis Ababa because there are really, really big vultures hanging around. When they smell that meat, they come and get it. It's really an extraordinary experience. And so for fun, we would get together and just make up our own fun with whoever was around. And that was the nature of living as an expat in all these countries. Were you blunt and direct with people back then? Or did that personality trait come later in life? My mother taught me something, I think, when I was 13.
Starting point is 00:10:59 She said, always tell the truth, Kevin, and you will never have to remember what you said. Now, that's what I started doing at that age, not thinking about how the truth can hurt people, but ultimately it's the right thing to do. And so that has been my, you know, who I became. I don't like to lie to people and be disingenuous to them just to make them feel good. If there's a fact they should know, they should know it. And it's a fact. It's the truth. And sometimes that rubs people the wrong way, particularly in business, when you tell them their idea has no merit and it's worthless. And I tell them that so they don't waste their time. So I'm comfortable doing that. I'm also very blunt. People know me
Starting point is 00:11:41 as blunt. And like you, I have people come in and pitch me regularly. I probably met in the last 20 years, one to 2,000 entrepreneurs coming in to pitch. And I'm exceedingly blunt. And like you said, I don't think people are used to it. And a lot of them don't like it. But for the same exact reasons, I do the same exact things. I'm wrong sometimes. And I tell people when they come in, I think if you meet with 100 people, you may get 50-50 or 10-90. And in some cases, I think this one will be 100 to zero. I share your views on that, but definitely people don't like it all the time. I want to be the best I can be no matter what I do. I want to be great, excellent. And at what age did you learn the value of hard work and get a work ethic? And what's your view on that? Where does work ethic rank in terms of ingredients to success? I did not have a traditional path to work because I had a very
Starting point is 00:12:42 jolting experience. And I've since learned that entrepreneurs, almost to a T, have had these seminal moments in their life where they choose the path of entrepreneurship for various reasons, but it's almost like destiny. And mine was a unique situation. It really was the moment that I learned that you might have to live a life underneath someone. In other words, not controlling your own destiny. And I've told this story many times, but I'll never forget it. I was working in high school now in the evenings
Starting point is 00:13:11 in an ice cream store. It was my first job, actually. It was called Magoo's Ice Cream Parlor. It was owned by a woman and she hired me. It was the first time I had a job and the first day I had a job. And when you are scooping ice cream, people want to take samplers and you use a little piece of wood, like a wooden stirring thing. You put a little bit
Starting point is 00:13:33 of chocolate ice cream on it and let them taste it. And they make a decision based on what they like. But when they do that, they often take their gum out of their mouth and throw it on the floor. And at the end of the day, there was quite a bit of gum and it turned black. It was stuck on the Mexican tile in that store. And the woman said to me, before you leave, you got to get down on your knees and scrape all this gum off. And I didn't want to do that because the only reason I took the job was the girl I was interested in grade 11 was working at the shoe store right across. And she was watching me and I was hoping that we could go out afterwards and just hang out. That was my strategy. And by working there every day, I'd see her every
Starting point is 00:14:11 day because she was working at the shoe store every afternoon. So I said to the woman, you hired me as a scooper, not a scraper. And I don't scrape, I scoop. And you probably have to hire somebody else to do that. And she said, no, no, no, no, no. I own the store. You're my employee. You'll do anything I ask you to do. You work for me. That's why I pay you. And I said, well, I'm not getting down on my knees and scraping that gum off because I knew she was looking at me from the shoe store right then. And she said, you're fired. And I said, what does that mean? She said, leave. I'll send along your eight hours or four hours of pay, whatever it was, and don't come back. Now, that was very humiliating for me. And I didn't, till that moment, understand the difference in the world. There are people who
Starting point is 00:14:58 own the store and there are people who scrape the shit off the floor. That moment, I made my mind up which one I was going to be, and I never worked again for anybody else. And so now I'm not dissing employees. I mean, you can have a great life working for someone else, and the majority of the population does that. And they have time for soccer and picnics and all the wonderful things that life offers. But that's not my life. I work 20 hours a day, 18 hours, crazy amount of work. I work harder now than I ever had in my life. That is
Starting point is 00:15:32 who I am. And that's how I define myself. And it has nothing to do with money anymore. I don't need any more money. I need more time. And the whole idea of that moment. And years later, we went back to that mall with a camera crew to find her. And I wanted to thank her because at that point, I could afford to bulldoze the mall if I wanted. But it was all because of her. She was the one that tilted my path and pushed me in the direction of entrepreneurship. And I'm forever in debt to her. That was an incredible moment.
Starting point is 00:16:03 In fact, a couple of months ago, I got a FedEx package that had a brick in it. That mall had been demoed and turned into condominiums. And someone who knew that story found me and sent me that brick. It sits on my desk. Great story. I lost my job after moving to LA. I was a lawyer. I hadn't passed the bar yet. 1993, firms were laying off people. I get called in. Well, I actually found out. I got a email from the librarian in Chicago where the firm was based. I was in Los Angeles.
Starting point is 00:16:34 Please turn in your library books today. Not the way you want to learn that you may be getting fired. I went out to try to find somebody. All the doors were closed. I got pulled into the conference room and there was the office manager and my boss saying, we don't have any work for you. You can leave today. And like you, that was humiliating. I read that you went home and you cried. Your stepdad and you had a talk and I went home. I didn't cry in the office there. I went back to my office, closed the door for three minutes, cried. It was my mom's birthday. I said, mom, happy birthday. I've got some bad news.
Starting point is 00:17:09 The irony is that October 27th is my mom's birthday. And through a lot of hard work, I had a business in college. I sold t-shirts. I went door to door, went through the dorms, got kicked out on one floor, went through the other floor. And I did this for all 12 dorms at Michigan. And I did okay, but I couldn't start a company then. I was new in LA. I had $3,000 in the bank, but I did well. My career, I worked hard. I saved money to take a risk to bet on myself. The irony is on my mom's birthday and on October 27th, 1999, our company went public. For me, one of the most important days of my life and obviously changed my future forever. So we all have to bounce back. We all have to work hard and we all have to realize what we want to do at that point in
Starting point is 00:17:59 time. Let's talk about the value of education, which is one of the building blocks of our success and our search for greatness. You attended Stansted College and St. George School, both in Quebec. You got a BA in Environmental Studies and Psychology from the University of Waterloo. Then you got a MBA in Entrepreneurship from the Ivy School of Business at the University of Western Ontario. For those of you who may not know it in the United States,
Starting point is 00:18:25 the Ivy School of Business is probably the best school in Canada. Let's talk about two things with respect to your education. First, I want to talk about a challenge you faced when you were in school. You had dyslexia and you managed to overcome that and graduate with honors. At what age were you diagnosed
Starting point is 00:18:44 and how did you overcome that? I was diagnosed with dyslexia very early on when I was starting to fall behind in grade school in reading. Dyslexics, it manifests itself in different people, different ways. Mine was quite severe because what would happen is I'd be walking down the street and the whole world would shift 90 degrees and I would be lost. I didn't know where I was. And I would have to close my eyes and shake my head and re-lock back to make it come back. This is one of the things that happens to dyslexics. And I could read, but I could read upside down in a mirror, which is pretty strange. And they don't really let you bring mirrors into the classroom. I was falling
Starting point is 00:19:25 behind in math as well. And my mother was really stressed about it because back in those days, they didn't know what this was. And there was a woman named Marjorie Golic and a professor named Sam Rabinovich that were doing some research at McGill University in Montreal, Canada, that had an experimental program where they were taking dyslexic children in and trying to help them in various ways. And one of the things that happens, because I've met lots and lots of dyslexics since, because people know about dyslexia now, and there's many famous business leaders that were severely dyslexic. I work with Damon John. He's dyslexic on Shark Tank, for example.
Starting point is 00:20:07 So I went into this program. I was very, very fortunate. And what they taught me in there was they said, listen, because the biggest problem you have as a dyslexic is lack of confidence. You think you're broken. You think there's something wrong with you. And that really erodes your ability to pace with the class or even have the confidence
Starting point is 00:20:26 to do anything else. And what they did, which was so extraordinary, which I think is common practice today, they told me at that age, I might have been seven or eight years old, maybe six. I don't remember. You actually have superpowers, Kevin. You have something that no one else can do. You can read in a mirror, backwards, upside down. Nobody can do that. Ask them to try it. That's a superpower you have.
Starting point is 00:20:50 And you were born with it and you're unique that way. And when I kind of listened to that over and over again, I started to say to myself, well, yeah, I do have superpowers and no one else has it. And it really bolstered my confidence to excel. And I would often say to people who make fun of me, you can't read. I say, oh, I can. Much better than you can, actually. I can read code. I can read things that you can't even see. And that really accelerated me.
Starting point is 00:21:16 And I remember it fondly as something that it was a mental switch in the way I thought of myself. And so from that day on, I can still read upside down in a mirror. I can read the regular way as well. So that was a great gift and a great opportunity and a great outcome for me, and I'm very fortunate. My second question about education is what role does it play in our future success
Starting point is 00:21:40 and our path to excellence? Is it necessary to get a formal education or is it enough to go through the school of hard knocks? Well, I get in a lot of trouble talking about this because when I finish with you here today, I'm going to Harvard to teach my class. I'm a guest lecturer there to graduating cohorts. And I tell them, I don't remember anything from my education. I don't remember any of the lessons in finance or anything from my MBA. None of it. It went in one ear and out the other. But I still know that cohort of people and they have assisted me in my businesses all around the world because they're the leader of banks or they're running industries or they're running companies.
Starting point is 00:22:27 The secret to education is not the education. It's the people you meet on the journey. Now, obviously, professors don't like to hear that, but it's the truth. And that's why you do it. That's why you try and go to college if you can, to meet those people. So all of these paths and doors open for you that wouldn't had you not had that opportunity. And the only lesson I remember from my graduating class, my second year of my MBA, the only lesson, a guest lecturer came in. He went to the bottom of the round, sort of like the case study Harvard classic
Starting point is 00:23:05 classroom with 180 people in it. And he looked at everybody for about three minutes, uncomfortable silence. I remember he looked up at me and I was sitting beside a guy named Barry Nicole, who had been with me for two years to my right. And this guy said, you guys think you're so hot. You're graduating next week with your MBAs, whoop-dee-doo. Who gives a shit? The world is going to eat you alive. A third of you are going to fail. Another third are going to work forever for someone else. And the lucky ones maybe will be successful in entrepreneurship. And the reason that's going to happen to you is you have no experience. You don't know what you're happen to you is you have no experience. You don't know what you're doing. You've done all these cases. Who cares? The real world will spit you out as soon as you get out there. And I leant over to Barry and I whispered in Barry's ear,
Starting point is 00:23:56 what an asshole this guy is. Because I was really feeling pumped about the fact that I had my MBA and I was going to go change the world. He was 100% right. Today, I'm that guy. I get emotional. Just remember, give me a moment here. Sure. It was really quite something because he was right. Sorry about that. No. You're making me drag up my past here. Anyways, that means you're a good interviewer, I think. Well, thank you. I remember that moment because Barry has since passed away. He was a very close friend of mine, but that person was right. And when I teach my class this afternoon, I'm going to say the same thing to them because they know nothing. You know nothing until you experience it.
Starting point is 00:24:50 You don't have any skills until you actually live it. And I've lived that way ever since because he was my education. That one hour session was the only thing I remember. Before we talk about the start of your career, I want to talk about the value of internships. The Jump Internship Program at my firm, we've had it 17 years. We get about 1,000 applications now each year. It's become a whole thing. We interview 150 to 200, and that yields 36 interns from all around the country, some of the best schools and some of the schools that are lesser ranked. The interesting thing is, on average, the kids and the students from the lesser ranked schools, they outperform the kids from Stanford and Harvard most of the time. They have a desire to compete. They walk in nervous. They look around the room. But it's been very valuable.
Starting point is 00:25:40 We teach the interns. I spend one hour a day with them. We have speakers come in each week. One year, I took all the interns to Tony Hsieh at Zappos, which is life-changing for many, many people. It's been something very good for me. I love to give back. And I think the intangibles many times are greater than the tangibles. To your point, you can learn whatever you want in school. But if you learn things like being the first in and last out every day, no matter what, you're going to get ahead. And there's all kinds of things in there that we teach. Between your first and second years of your MBA program, you worked at Nabisco. And then after you graduated, they hired you as a brand manager in their cat food brand. Can you share with us how this experience and what you
Starting point is 00:26:30 learned there about beef paste and tuna paste contributed to your later success at the learning company and in your career? Yeah, as part of your MBA in the summer, you have to take an internship. That's part of your education. And so I chose Nabisco Brands because I was interested in marketing. And the day I arrived, the brand manager there, who was Dutch, really interesting guy, he said to me, I'm going to take you to the rendering plant where we make cat food. The brand was called Miss Mew. And my job for those 90 days was to design a new flavor and get it on the shelf. So the whole idea of cat food is the more facings, the more market share you get,
Starting point is 00:27:10 more flavors you have on the shelf that are maintained by the grocers. And so when I got to the rendering plant, there was basically two production lines. One was taking, I'm not exaggerating when I tell you this, the faces of cattle and chicken faces and renderings and certain fat off organs. I mean, it was just brutal. But every piece of protein is used when an animal is slaughtered. And it was rendered using papaya juice to break it down and then pressed into a patty. And that was the basis upon all flavors that were beef flavors. And then Sea of Japan underbelly tuna is not sold in premium markets is what makes all of the fish
Starting point is 00:27:55 flavors of most cat foods. And so you add some bacon bits, you add some corn, you add some whatever that changed the flavor and call it something else. But everything is those two pastes. And what he explained to me was, look, human beings like to open a can of cat food and have it very stiff so they can turn the can over and drop it into the food plate. And it keeps its round shape. They were like little tins. But cats like liquid. They want a soup. We've tried to sell soup for the cats, but people won't buy it. They think they're getting ripped off. So you have to find a balance
Starting point is 00:28:33 of making it moist enough so the cat will eat it versus the person that wants to just have a puck there. And we had a plant that had over 500 cats in upstate New York that we would sample all these things. We would try it and test it until we got it right. I went to see that, and that's where I met Fluffy, a cat that was 27 years old. It had no hair. It was leaking out of every orifice, had no teeth, but it was still alive. It had lived its whole life on dog food, not cat food. These are crazy stories, but you can't forget stuff like this. And what he was trying to tell
Starting point is 00:29:12 me was, you only need two engines. You need the chicken-beef mixture, and you need the tuna fish. And everything else, you just dream up. And that's what I did. And I remember at the end of the session, just before I went back for second year of MBA, I had to go to the head sales meeting, hundreds of sales reps. And I learned by fire how that worked. I said, guys, in order for me to get a good mark on this, you got to get this sold into every grocery store in North America. And the head of sales got up and, you know, somewhere back in the room said, Kevin, how good is this flavor? And I said, it's fantastic. I worked with the cats. I know they love it. And he said, no, you're going to eat some right now. Prove it. He made me eat the whole tin in front of
Starting point is 00:30:01 the entire sales group. And later I found out that was what they did to every intern every year, but it was a successful launch. But the reason that's important, I didn't realize at the time, not the eating it in front of the sales force, but what the head Dutch guy taught me about the two engines, because that changed my entire life. It's so amazing the lessons you learn that you store in your memory and they bring them back later to apply them in a different way that becomes very powerful. You work at Abisko when you graduate and then you began a brief career as a television producer with two of your MBA classmates. You co-founded a company called Special Event
Starting point is 00:30:45 Television that produced original sports programming. You did that for a little while, and then one of your partners bought you out for $25,000. It was a little win. But let's talk about what happened next. After selling your share of this television company, you started SoftKey in a Toronto basement, a garage basement. That's where a lot of companies get going with two partners. The company was a publisher and distributor of personal computer software for Windows and Macintosh computers, which like it is now, was a very crowded field with many competitors doing very similar things. What on earth did you know about computers at that time? And what was the aha moment where you said to yourself,
Starting point is 00:31:27 there's a need in the market and I want to fill it? When I was working in the television company, Special Event Television, we had a contract to do a lot of sports programming for the networks in the original six cities for the NHL. So Detroit, Philadelphia, New York, Boston, et cetera. And we would travel a lot during the week. And I was a cameraman, soundman, film editor. I worked on an eight plate Steenbeck, which is a device you don't see much anymore because everything's done digitally. And I have kept up my editing skills. Every weekend I cut something for our social media. We've got lots of editors, but I want to keep my chops up. So I still edit. And in those days, when you were doing film and you needed the title of, let's say, a hockey player or something, you had to
Starting point is 00:32:09 actually create the font and burn it into the film. And I had met a man named John Freeman, because these are expensive, just doing this, actually drawing the fonts or having an artist draw the fonts. He had taken a Hewlett Packard single pen plotter, a device that drove a pen in an X and Y angle. And he wrote some software to actually write fonts, to write letters. And I met him in the basement of what was called the Osborne Computer Club. I bought an Osborne computer, which was CPM computer, the first portable computer ever. You can look it up online. It was a remarkable device.
Starting point is 00:32:49 He and I met at this club, and he was a programmer. And he showed me the software, and I said, John, that's incredible. That's going to change the world for a lot of people because you're allowing them to do charts and bars and graphs with letters and everything else. Why don't we form a partnership? Why don't we go 50-50? I'll be the marketing guy, you'll be the programmer, and I'll go sell this software to every single plotter manufacturer all around the world, in Japan, in the US, Germany, you name it. Because there's millions of plotters at that time being made.
Starting point is 00:33:18 That's exactly what we did. Instead of trying to sell it for $300 a package, I went to a woman named Mary Zoller, who at the time was the brand manager for Hewlett Packard All Plotters in San Diego. And I met with her and said, Mary, why don't you just give me 10 cents a copy and put this in every single plotter? And she said, Kevin, very interesting idea, but I'm the top of the pecking order. I can do that anytime I want. Why don't you sell it to
Starting point is 00:33:45 somebody else that was one of my competitors first? And she pointed me in the direction of a couple of Japanese manufacturers. I went to see them next and they said yes. And from no sales at all, we started getting checks for millions of dollars because we were selling it at 10, 20, 30 cents a copy for millions of plotters. And that was the beginning of software products. And that eventually became the learning company that started in my basement. And I was traveling all around the world. It was just the two of us in the beginning. And then of course, it was thousands of employees later on, but it was the idea of OEM bundling. It was the idea of marrying the software with the firmware, with the plotter, that was the success of Softkey
Starting point is 00:34:23 Software. And then of course, we became the largest educational software company in the firmware, with the plotter that was the success of Softkey Software. And then, of course, we became the largest educational software company in the world, the largest reference company in the world. We did Compton's Encyclopedia before Wikipedia. We did all that stuff. And I never, never forgot the lesson because when we had competitors, like a company called Broderbund, we did a hostile takeover of them. And I said to my board of directors, I told them the story of the cat food. My thesis was this, let's buy everybody. Because in educational software, there's basically two directions that you're trying to go, math and reading scores. You're trying to advance math and reading scores at children between four and eight years old, because that's how they get
Starting point is 00:35:04 through high school. That's how they get through high school. That's how they get to college. It's all math and reading scores, still is today. And I said, guys, let's buy every brand and let's just do two engines, one for math, one for reading, and we'll fire everybody else. We don't need all that overhead.
Starting point is 00:35:19 We'll just have two, and then we'll add characters like Big Bird and we'll add characters like Barbie and we'll add characters like Rita Rabbit on top of, just like you added the bacon bits to the beef patty in the cat food thing, because the kids don't buy the software, the parents do. So it really worked. I mean, our cost of capital went down because our profits went up, our stock price went
Starting point is 00:35:42 up, our access to both debt and equity at much higher prices reduced our cost of capital, and we started buying everybody. We acquired the entire industry and became the largest educational software company in the world until Mattel bought us because we were actually encroaching on the toy companies too.
Starting point is 00:35:56 Kids only have so many waking hours, and when they stopped playing with dolls, they were using Rita Rabbit. And so that was the thesis of why they bought us. But thank you for that cat food story. You reminded me that I owe it all to two people. One was the woman who fired me from Magoo's ice cream parlor, and the other was that Dutch product manager who taught me about engines. That's what it boils down to. We all have these eureka moments where we say, aha,
Starting point is 00:36:22 this lesson is going to stick with me forever. Let's go back to the very beginning of the companies. Like all companies, you need money to fund it. You had an investor who's going to invest $250,000. He backed out at the last minute, the day before signing your documents, which left you looking for funding. This happens a lot when you're raising money. It's not uncommon. So you took your princely sum of $25,000. You went to your mom who lent you $10,000 with that. We start with friends and family. And you've already walked us through now the growth of the company, buying the competitors.
Starting point is 00:36:57 As you said, you took the learning company name when you bought it for $606 million. And when that deal closed, you moved the company to Cambridge, Massachusetts, home of Akamai Technologies. And then six years after that, it took six years, Mattel bought you for $4.2 billion. I mean, that's a monster deal, massive home run, but it was soon called one of the most disastrous acquisitions of its time. What happened there? Can you take us through it from starting a company to growing it to all of its challenges and all of its successes to the massive sale, and then what happened after the sale? Can you tell us how you bounced back from that?
Starting point is 00:37:38 That could not have been fun. No. In fact, what happened was this. The thesis of the merger or the acquisition, if you want to call it, Mattel was going, the thesis of the merger or the acquisition, if you want to call it, Mattel was going to buy us. And then we would take their big brands like Barbie, for example, and put it into the math and the reading engines and the same with American Girl. And we had demand for those products by the millions of units. And so when I got there, I immediately moved to LA to start working with the product managers to get these projects out because we'd already pre-sold them to Walmart and Target and some of the big distributors all around the world.
Starting point is 00:38:13 And my assumption was, as we always could get out a product, we could do it in four months because we already had the engine. We just needed the graphics design of the doll or whatever it was going to be. So I explained that to the management at Mattel. And I said, look, here's the path. Here's the order size. Here's what's going to happen. Here's the trajectory. Here's the target sales. Two years later, we still hadn't released Barbie teaches math or Barbie helps you read or teaches typing or anything. The culture was so different. It was so not entrepreneurial. A toy company that's been
Starting point is 00:38:45 around for 100 years does not move quickly. They had a whole procedure in terms of how to integrate it and checks and balances on the brand and everything else. And it was extremely frustrating for me because we were trying to harness the entrepreneurial spirit in a very large corporation, which was impossible. It was a pretty big lesson. In retrospect, that was a huge mistake because we should have recognized that it wasn't going to work. And worse, there was huge conflict between myself and the board of Mattel because I was, for a while, the largest shareholder they had, personally. I own more stock than most of the board members did. And I just said, guys, this isn't working. And as a shareholder, I'm unhappy. We've got to fix this.
Starting point is 00:39:26 And I know how to fix it. So get out of the way and let me do it. Otherwise, we're going to lose a lot of value here. That's not what they did. They fought a tooth and nail. And it was an important lesson for me. Culture matters in a business. And if you're going to sell your company, don't stick around afterwards.
Starting point is 00:39:41 Start a new one. That's what I did after that, because I've been very fortunate since then. I've had many great successes and many great failures, and I've started lots of things and invested in lots of things. But that was an important lesson for me. And it happens in corporate culture. You never do it twice. I mean, I'll never do what happened there again because I know to avoid that. That's the whole idea of experience that you wouldn't have seen coming. But yes, it was challenging, no question about it. And later, in later years, in fact, just a few weeks ago, I had a lunch with Alec Gore, who's a very famous private equity, one of the big SPAC operators. And that's where he and I met years and years ago,
Starting point is 00:40:18 because he bought some of the assets. What I eventually tried to do was buy back the learning company from Mattel. They wouldn't sell it to me. They sold it to Alec instead, but we've become great friends since then. He's from the great state of Michigan, as am I. What a career he and his two brothers have had. I think there's something in the DNA in that family. Let's switch gears and talk about your views on business. You've said that business is war and that you want to kill your competitors and you want them to fear you and that you want to make their lives miserable and you want to steal market share
Starting point is 00:40:50 and you want everybody in your team to think you're going to win. Is business really war? It is. And if you think it isn't, you'll be one of the people that loses. It's competition for the best ideas, the brightest people,
Starting point is 00:41:03 the most market share, the most markets, the most market share, the most markets, the most innovative products. It's always war. And this kumbaya thing is put out there and taught in some schools these days is ridiculous because when you get out there, if you don't understand that you are marching to the orders of your shareholders, your employees, and your customers, and you have to win, you won't win. Now, I have nothing wrong with mission-driven businesses. If you want to give a dollar away every time you sell a product or plant a tree, I get it.
Starting point is 00:41:30 And that, in fact, is a good strategy because a lot of people care about that or eliminate plastic waste, which I'm a big believer in from my environmental days. But the whole idea is that you have to set some parameters that you have to achieve, and you've got to get the whole team following in that direction. If anybody is not agreeing on that direction, get rid of them.
Starting point is 00:41:49 They're destroying your culture. Everybody has to agree. And what I would do with my management was always say, look, here's the plan for the next quarter. Does anybody have an issue with it? Is there anything you don't like about this plan? Is there something you want to change in this plan? Speak your mind now or forever be at peace because we're going to go achieve this plan. I don't care how hard
Starting point is 00:42:09 we have to work to get there or how many hours we have to work or where you have to go to to make it happen. We're going to achieve this plan because we're going to turn around and tell the street, this is what we're going to do. And shareholders are going to listen and we're going to do it. And I think that is business. That really matters. Now, you may not agree with me. I don't know any other way to do it. You need to motivate people. They have to believe in your leadership. They have to want to follow you. And if they don't, you've got to help them find someone else to follow. That's your job. And I would always give great severance packages to people that didn't want to get on board. I just got rid of them. And everybody that worked with me understood the challenges we had and faced it. And we worked together
Starting point is 00:42:48 to make it work. And we all did well together. That was the whole idea. Let's switch topics and talk about being an entrepreneur. What is an entrepreneur? And can you learn to be one? Or does it have to be in your DNA when you were born? It was in my DNA from the time I was a young kid. I always knew I was going to start companies, but can you learn it if you're not born with that gene? This is the age-old question you've raised. It is the most important question. Can you teach entrepreneurship? I've tried to answer that question over the years. I've tried to identify entrepreneurs in my classes that I teach. I believe that what works and what makes someone an entrepreneur is a burning desire to be free,
Starting point is 00:43:39 to have your own freedom that no one can tell you what to do. And the only way you're going to get there is through entrepreneurship, because it's not about the greed of money. It's the pursuit of personal freedom. And so when I meet people that have a burning desire to be free, then I know I'm working with an entrepreneur because you may try five or six different ideas and they may all fail. But the fact that you keep going back and trying again is that burning desire. And I don't think you can teach that.
Starting point is 00:43:59 You either have that desire or you don't. And it's only present in about a third of the population. In every country, it's the same. You find two-thirds of the people work for the other third. And of that third, 10% are remarkably successful. And so if you think about it, it's a very small fraction of people that change the destiny of an economy with profound businesses that grow and grow and grow because they're very successful at solving someone's problem. But the motivation they have is that to pursue personal freedom. You will find that in today's modern entrepreneurs, Elon Musk, for example, look at what that man's achieved,
Starting point is 00:44:36 and he's just getting going. And so he has a burning desire to do things his way. My son works for him at Tesla. The company has a remarkable culture of getting stuff done. It's interesting. I've met with a lot of venture capitalists over the years. We've funded around 90 companies in 20 years. I have my own list of things of what I look for when I'm considering funding somebody. What do you look for in an entrepreneur when someone comes in and pitches to you? I look for the ability to pivot because whatever idea they have is probably going to fail or that's going to have to be changed. You always start with the optimism of the idea, but I look at the entrepreneur and say, does this man or woman have the ability, if things do not work out, to pivot, to change
Starting point is 00:45:18 so that all this capital isn't lost? And I'm pretty good now at determining winners and losers. That's what makes me successful as an investor. I don't get it right all the time, but I certainly have been successful. And I'll let you in on a little secret. About 70% of my success over the last decade, now it's more, it's more like 12 years, has been with women entrepreneurs, which 70% of the really good outcomes have been managed by women. And I think I have a theory about it. They mitigate risk very well. They focus on return of capital first, not on capital. And that old adage, you want something done, give it to a busy mother is true
Starting point is 00:45:59 for a lot of women. They can judge and balance a lot of things at the same time. And so I'm a little biased now. If you look at the deal flow and I do a lot of things at the same time. And so I'm a little biased now. If you look at the deal flow, and I do a lot of deals, we have currently, we just closed another one last week, we have 35 portfolio companies right now. That's a lot for any venture firm. But I have the benefit of social media so that I'm able to help them reduce their customer acquisition costs in an incredible way. That's sort of our secret sauce in my venture firm. I basically go work for these people to help get their story out, reduce their capital costs and their customer acquisition costs.
Starting point is 00:46:34 And in exchange, I get very proprietary deals. And I know what my value is. So this model really works for me. But I really look for that ability to pivot because you know, and I don't have to tell you this, you're going to go through a lot of hills and valleys before the deal's done. It's interesting. We also look at the exact same thing. We started investing in female entrepreneurs probably seven years ago. It wasn't that we didn't want to fund them before. It was just so few were coming through.
Starting point is 00:47:10 I've been a huge proponent of increasing the number of women in finance and in venture capital. And we started funding, as I said, seven years ago. We also have looked at our portfolio companies, and we found the exact same thing. On average, the success rate is higher with female-led founders than with male founders. And we have a number of very interesting, fun companies in the portfolio that are doing exceedingly well. I also invested in Jesse Draper's fund. As you know, Tim Draper, one of the most successful VCs of all time, his father, his kids, fourth-generation VC. Jesse, she only invests in female founders,
Starting point is 00:47:46 and she's killing it right now. So we share that same view. What's your investment strategy as a whole? We're watching Shark Tank. I see you invest in all kinds of businesses now. On that show, obviously, you don't know what's coming. I mean, you've invested in from A to Z, non-related. You have your venture firm. What are you looking for in terms of a strategy? Is there one or do you just take every deal kind of one off and you look at every specific situation? I have deals in all 11 sectors of the economy, including real estate.
Starting point is 00:48:20 I am not driven by just one sector. Some people just do biotech, some do pharma, some do manufacturing. I go everywhere. And lately, I've been doing a lot of work in crypto and decentralized finance. It's sort of a multi-sectoral. I look for that entrepreneur, that woman or man that's going to drive the process. I look for structure in terms of how the challenge I have is I know my value. And so not to be arrogant, but when people come to me and say, look, we're doing a round at a 10 million valuation or 25 million valuation, and we're closing it, there's a million left. I say, look, I have no
Starting point is 00:48:59 interest in doing that. You want to put my name on your cap table. We both know why you want to do that. I get it, but that's not a deal I'd ever do. I am not my name on your cap table. We both know why you want to do that. I get it, but that's not a deal I'd ever do. I am not like any of your other investors. You want me as an investor. You have to make me a founder, which means you're going to give me founding shares of the company for free. Now, a lot of people choke when they hear this, but then hear me out. I say, and here's what I'll do. I don't care how many rounds you've raised. After we agree on the founder shares that I'm going to take from you, you're going to give me for free. I'm going to peripursue my percentage ownership into every round you've ever raised at that price. So if you did a round at 5 million valuation, I'll give you cash for my 7% of the
Starting point is 00:49:41 ownership. I generally don't do this. I start, I ask for 9.9% of 500 shares, so I'm not an insider. And you don't want me as an insider because social media is what's so valuable. I have to be able to speak about why I invested in it. So I don't join the boards. And then I invest in every round for my 9.9%. 50% of the companies absolutely choke when they hear this. They say, why would we ever do that? And they don't. The other half do. And the reason they do it is I simply let them talk to my CEOs.
Starting point is 00:50:10 I don't sell myself. I let my CEOs sell myself. They do the work. They explain how my organization changes their path and makes them far more successful in raising capital at a lower cost because now there's a direct correlation between social media and market cap. You've seen it in Reddit. You've seen it in Robinhood. You've seen it on meme stocks. It's very powerful. And I know it's a fact. And then I help them with customer acquisition. There isn't a single retailer
Starting point is 00:50:38 on earth that won't return my call. That's one of the great things about being a shark, right at the president or CEO level. And so we can do a lot of things together, but I don't do it for free. And obviously, that gives me a huge advantage against just some random VC. And it works. You're a very sophisticated, very experienced, highly educated investor. You have access to lots of deals that the ordinary person doesn't. What kind of investment advice do you have for the average retail investor? And as part of that, does it make sense to put all of your money or most of your money into the S&P 500, given that there are probably less than five investors in the entire world who have beaten it over the last 30 years,
Starting point is 00:51:21 and the chance of the next Warren Buffett showing up at your door in Topeka, Kansas, or wherever you're living is way less than getting struck by the odds of lightning, which by the way is one in 700,000. Yeah. I do have trusts. They do invest in the S&P 500. I do own, or I'm a half owner of an indexing company that services pension plans and sovereign wealth and state funds and everything else. So we design derivatives of the S&P 500, and I invest in those that tend to be a little higher quality. I don't want to own every company in the S&P 500. I mean, the airlines are uninvestable now. Their balance sheets are upside down after the pandemic. I think
Starting point is 00:52:00 United had something like $8 billion of debt. Now it's got $23 billion. It happened in 18 months. I would never own that. That's just a speculation now. So there's certain rules I have. But that's way different than investing in private companies and being a venture capitalist. The majority of the money I make is not from the indexes. The majority of the money I make is from bets I make on men and women that I invest in. For example, three years
Starting point is 00:52:25 ago, someone came to me in Florida and said, would you like to be an investor in LSD? And I said, no, that's an illegal schedule on narcotic. And he said, no, no, I'm going to do FDA trials towards turning it into a medicine. I thought that was pretty crazy. That was MindMed. I think I bought into that when it had a valuation of $10 million, and it's trading at a billion and a half now. And I was a founding shareholder of that. I believed in the idea of taking psilocybin and LSD and going through clinical trials to see if it could help opioid addiction and things like anxiety.
Starting point is 00:53:00 There's all kinds of research going on in the space. And in fact, there's many other companies that have pursued it. We were the founders of that whole space and were the first to ever do it. The same thing with recent investments are in WonderFi, a company that is doing decentralized finance on an app. So democratize it for people that can't understand the complexity of staking and loaning and all the things you have to do to use DeFi. Just bought a piece of Immutable Holdings, a company that owns NFT.com and is building
Starting point is 00:53:30 out the NFT platforms there, a large piece of it. So I'm very involved in that space. Looking at two more deals next week. I mean, the deal flow is huge and I have a whole team of people that I work with, but I'm intrigued by entrepreneurship. I'm intrigued by the magic of what happens when you put capital to work with a strong leader and just watch it blossom like a flower. It's just incredible. And all the twists and turns that occur, I give them advice I can. I help them with social media, obviously, and I help them with customer acquisition. But generally, it's them.
Starting point is 00:54:05 It's their idea. And my money is just gasoline on their fire. We've talked about making money and success, but let's switch gears and talk about challenges and failures. For all of us who ultimately achieve excellence, we have many failures along the way. For going to achieve greatness, we need to push forward and push through them. We've already talked about how you overcame dyslexia, how you were fired by Mattel or left Mattel, but you've had some other challenges too. You lost $2.5 million in a partnership with
Starting point is 00:54:35 a large cable company. You wanted to create an online dating service with them. As we now know, we have matched Tinder, Bumble, and a whole variety of similar companies. It's a great idea. The deal didn't work. It was a bad partnership. But let's talk about work-life balance and family in a few minutes too. I want to ask you about the expression that failure is not an option. Is that right? Is it okay to fail? And going one step further, is some failure a good thing?
Starting point is 00:55:02 What's your advice to people, for example, who've been fired once or multiple times, or those who've started a company and failed, or multiple companies that have failed? Or if you're one of the 1.5 million people who declare bankruptcy every year and you want to start a company? Failure is actually very important in the journey of any entrepreneur. I prefer not to invest in people that have never experienced it. I prefer to invest in an entrepreneur that's failed two or three times and understands why they failed. That experience is very important and very motivating. I have failed many times.
Starting point is 00:55:34 I've made very bad investments and lots and lots of money, but also made lots of money. I mean, it is, you are not going to have a perfect track record. No one will, particularly in investing in venture. I mean, that's so risky in itself anyways. There are some rules, though. It's important to understand why you failed. I'm talking to an entrepreneur, and they're telling me about something that didn't work out, and they can't explain to me why it didn't work out. Then I won't invest with them because they haven't learned anything.
Starting point is 00:56:02 They just have failed. So I would say failure is an option, a very good option to make you better as an entrepreneur. And thinking about the motivating aspect of it, entrepreneurs hate to fail. So when they start the next journey, they try even harder. And unfortunately, and I say this to my graduating cohorts, there is no life balance for an entrepreneur. The whole idea is you sacrifice your early years to have freedom in your later years. That's the whole idea. Unfortunately, you find out in your later years you want to even work harder because all you know is work.
Starting point is 00:56:42 And you do sacrifice a lot of family time. You don't go to picnics. You don't go to soccer games. You're not free on the weekends. I'll tell you a story about a class I was teaching a few years ago, a night class. It started at six and went till nine o'clock as these do. And this was a big cohort. I mean, it must have had 300 people in it. It was a very big room. Microphones, cameras, big speakers, and screens so they could see you down at the bottom. At the end of the class, like five minutes before nine, this fellow at the back raises his hand and he says, can I ask you a question? And I said, sure. You haven't said, you haven't contributed anything to this class. You haven't said a thing in three hours. So welcome to ask a question. And I said, sure, you haven't said, you haven't contributed anything to this class. You haven't said a thing in three hours. So welcome to ask a question. I said cynically to him
Starting point is 00:57:29 because he hadn't said anything. And he said, I want to tell you a story and ask advice. Basically the story was this. He was in his graduating year of engineering, electrical engineering, and he was also a coder. He could write code. And he had designed a compliance cloud-based platform for hedge funds of 250 million and under. So he found that niche market. It was a royalty-based system. He did all the mark-to-market compliance so they could be compliant in their reporting to the regulator. And he was able to acquire his customers just by word of mouth. The run rate was $5 million of free cash flow a year while he was in his dorm. So he says to me, my girlfriend came to me today and said, I have to make a decision. I said, what's the decision?
Starting point is 00:58:21 Well, we're engaged, but she doesn't want to live this way. I have no time for her family. I have no time for her. I work every weekend. I work all night. And I'm running this business, and I'm trying to graduate from engineering. And the guy's at the top of his class also. He's very gifted. What do I do?
Starting point is 00:58:37 I don't want to lose her, but she's going to walk out on me if I don't change. And I said, OK. And now the class is, you could have heard a pin drop. Half the class was women, half were men. I said, listen, let's be pragmatic about this. Which one is easier to replace? Your business that you've worked for three years to build is now generating 5 million of free cash flow, or your fiance? And a lot of people didn't like that answer. And he said, well, what do you think? I said, I think she's the wrong person for you.
Starting point is 00:59:14 I'm not Dr. Phil here, but you're an entrepreneur, a successful one. There isn't a woman in this class that wouldn't want to date you next week. You're a good looking guy, you have $5 million. I think you could find someone else that understands your journey. Entrepreneurs need to understand that their partner has to understand them was my point. Anyways, that class was a shit show. It didn't end until 10 o'clock as we debated this whole thing, romance and all this
Starting point is 00:59:39 stuff. I get it, but it was an important moment for him to understand the journey he had chosen. There was no going back. And from what I understand, he has a family. He's very happy, but not with that woman. So maybe I did something right that night. But in your own situation on the flip side, you said that you weren't around for your kids, Trevor and Savannah. You said that you were a absentee parent. You and Linda at one point had separated. And you said that later in life, you learned to treat your marriage as a business partnership that deserves the same attention and priority. And then I heard you say at the beginning of this podcast, you're working harder than you ever have. It's funny because when our company went public and I began my own firm, I mean, the Akamai thing, working 100 hours a week.
Starting point is 01:00:32 I was commuting from Los Angeles to Boston and it was hard. And I thought, all right, now I have my own firm. I can be my own boss. And I worked harder and have since then. And I have five kids and it's important to me to be home for dinner every single night. And there's a small handful of nights over the last 20 years that I have not been able to do that. I have the freedom, as you've said. The successes brought me freedom. But in your case, it took a serious impact. Have you changed your view on this a
Starting point is 01:01:03 little bit, given the issues you've had with your own family and the sacrifices that you've made? I'm at peace with myself now. I don't think I'm going to change. I don't think I know how to. I am very happy working this way. I'm fulfilled doing what I do with this incredibly intense schedule and everything else. The way I solve for it is I'm very, very fortunate. I can go anywhere I want and bring anybody I want with me anytime I want. And so last week, you know, my wife said, look, we haven't had a vacation with the kids since the pandemic started. I'm just going to pick a place and you make all the arrangements and let's go there. So we decided
Starting point is 01:01:42 to drive down the California coast through Big Sur and Carmel and everything else and just stay in different places, post ranch and all that, all the way down and just flew into Napa, spent some time at our, we have a wine business there. I'm a shareholder in Vintage Estates where we make O'Leary Fine Wines and we run our direct consumer business there. So we spent some time there shooting some commercials. And then we just drove south and it was great. I still had to do a few calls, but it was a great time to be with our family. We did corny stuff, like went to the Monterey Aquarium and we had lunch on the beach and all that stuff. You need, I agree, you need to stop and smell the roses. And I can certainly, I'm very fortunate
Starting point is 01:02:28 to be able to do it any way I want. And so I try and do that. And for my kids, I'll say, look, pick any weekend, anywhere you want to go, and your friends and girlfriends, everything else, I'll make it happen. And I do that occasionally. Because my kids are now 25 and 28.
Starting point is 01:02:44 I mean, they're not toddlers anymore. They have their own lives and they're working and they have all the new stresses that life drives on you. But we do get together. We're going to move on now to the most popular and debated topic in finance and technology during the last five years, blockchain NFTs and decentralized finance. 2019, you said Bitcoin is garbage and worthless. Now you're a huge investor in blockchain companies and now makes up 7% of your investment portfolio. And you've said that crypto is going to become the 12th sector of the S&P 500.
Starting point is 01:03:14 At the beginning of 2017, a little less than only five years ago, Bitcoin had a market cap of $17 billion. Today, it has a market cap of $1.2 trillion. What's happening here, Kevin? I think three things have happened. The first is that the concept of a digital asset is not foreign to this new generation. They've lived digitally since they were born. So you've got Gen Z, you've got millennials, and a certain percentage of the population of baby boomers have all realized that digital assets are real and scarcity is real.
Starting point is 01:03:51 And the theory behind Bitcoin is that of scarcity. I have, over time, come to appreciate that asset as property, not as a currency. And people have different beliefs in it. But I don't sell my coin. I'm going to own it forever. And so look at it as an asset to hedge against inflation, the same way I do with gold. Gold is a 5% weighting in our operating company's portfolio, but Bitcoin is more than that now, and so is Ethereum. But
Starting point is 01:04:15 I think the way to look at it, and everybody has a different opinion, but what has turned me around on this, first of all, was the regulators starting to loosen up in countries like Switzerland, Germany, France, England, New Zealand, Australia, Canada, where I also invest. And so I had more crypto assets there before the US, because right now we're still in limbo with regulators here. But you can buy an ETF with Bitcoin underlying itself, not futures in Canada. And many more of these are coming in other countries. But here's the way
Starting point is 01:04:45 I think you should look at it. Cryptocurrency and decentralized finance is nothing more than software. It's productivity enhancing software. And if you own Google, as I do, and you own Facebook, as I do, and you own Microsoft, as I do, these are large weightings in our overall company. Why wouldn't you own blockchain? The potential that it has to enhance productivity, to reduce costs in the largest market on earth, the currency and financial services market, is so incredible. It should be part of your portfolio. Now, in saying that, I don't just own Bitcoin and Ethereum. I own 20 other positions in miners of Bitcoin, in companies like Immutable Holdings and WonderFi and their equity. I also own many different tokens,
Starting point is 01:05:35 level one and level two chain companies. I have a team working on this now. So we manage it just like we would any portfolio or ETF, where we actually have position weightings in these things, and we mark to market them every day. I've recently became a shareholder, one of the 69 shareholders that did the private placement in FTX. And I'm their paid spokesperson, along with Tom Brady. I mean, this is a remarkable company run by Sam Bankman-Fried, who's only 29. He's worth $22 billion. I love working with him. He's fantastic. I'm using his platform, the FTX platform, to be compliant in all of the work I do in crypto. So to me, that's the most compliant platform there is. It's the largest global platform
Starting point is 01:06:15 that I think has institutional compliance built into it. And last week, when we were looking at our deal flow, 40% of what we're investing in now is either crypto or in new deals or in decentralized finance. It's the most exciting thing that's happened since the birth of the internet. So I think it has tremendous potential. And yet you'll find naysayers. You will find people that think it's worthless. And they've said it publicly.
Starting point is 01:06:42 I was one of them. I was one of those skeptics. And I forever get that video shoved in my face when any of these podcasters interview me. They love to start with that. But when things change, I change. And I'm glad I did because it's one of the best performing assets I have right now. So you have to get your head around it. And if you think of it as productivity software, which everybody's been investing in for decades, that might get you over the hump. And it's binary. Either you want to invest in crypto and DeFi or you don't. And if you do, how do you invest? And that's the challenge in educating yourself and getting a
Starting point is 01:07:14 diverse portfolio. You have also invested in non-fungible tokens, NFTs. For our listeners and viewers who are unfamiliar with them, a non-fungible token is a unique digital asset that represents the ownership of real world things like art, video clips, music, and some other things. They use the same blockchain technologies that power cryptocurrencies, but they are not currencies. You've said that non-fungible tokens are fun. In a similar vein, collecting things is fun. You're a huge watch collector and at some point that has become a asset class for you i'm an art collector i'm the kind that hangs paintings on my walls put sculptures on my floors but the nft world in art is a teensy bit different in that world there was a guy named mike winkleman this guy was a graphic designer turned digital artist who was known as Beeple,
Starting point is 01:08:06 or before that, Beeple Crap. He made a digital picture at some point in 2021 that was sold at a Christie's online auction for $69.3 million. This is a JPEG file, not something you can touch or hang on your wall. You have people who are buying eight-second video clips of LeBron James dunks for $600,000. It's an NFT frenzy out there. And you and the best venture capital firms in the world are backing them, calling this the next big thing. What are your thoughts on Beeple and non-fungible tokens and all of this? And is it going to be like the early dot-com days that I was a part of, where so many of your friends were a part of, and you were probably a part of, where the frenzy is going to die down and investors lost tens of billions of dollars, and more than 95% of these companies are going to crash and burn?
Starting point is 01:08:57 No, it's different. And I'll tell you why. That piece of art you're referring to, the $69 million piece of art, is now known all around the world. It has become the Mona Lisa, the first of its kind in NFTs. And it in itself has built its own value as such. If you own that NFT, I believe it will sell for more than $69 million one day because it's so famous. That's what happens in the digital world. Something unique is that even though you can go online right now and look at it on your computer screen, you don't actually own it. The ownership is the person that owns the NFT with the smart contract built into the Ethereum blockchain. And so that has tremendous value. Where I think the most interesting market is and
Starting point is 01:09:41 where I'm going and where I'm investing in NFTs is where you can tie a physical asset that has already proven itself in the physical world to the digital NFT world. And the example I'm going to give you is the watch industry. Now, I am a large watch collector. I know the largest watch collectors in the world. I know the CEOs of all the watch companies. I'm very fortunate to have been collecting watches for decades. I have unique one-of-a-kind pieces. They've gone up in value immensely. But every time I want to buy a watch, and this is a $20 billion market annually. So let's say you want to buy a Patek Philippe 75th anniversary world time, very famous watch. They've only made 1,700 of them. And I wanted to buy one that was still in
Starting point is 01:10:26 its box. There are collectors that buy these pieces and never open the box, never wear them. And they wait a decade and they wait till someone like me comes along that's going to pay a significantly higher price than it was sold at 17 years ago, 18 years ago. Here's the challenge. How do I know it's real? Now, in the case of a Patek watch like that, there's only one man that can authenticate it for me, and John Reardon in New York City. So I have to find him. I have to get his time. I have to ship the product in bond from Hong Kong, where it happens to be sitting, get him to open and look at it and tell me that it's real, that in fact, it is a Patek Philippe and not a knockoff. I could have avoided all that had there been an NFT of this watch created to authenticate it with
Starting point is 01:11:10 all of the information that I need to have built into the chain, into the contract. I want my entire collection to be NFT because there's so many people that want to have my NFT of my steel white face Daytona that I wore for 13 years on Shark Tank or my one of a kind Ming. They'll never own the watch, but they'd love to buy the NFT of that watch. And so we know what the watch is worth in the physical world. And we'll find out through the auction and the cry price discovery on the NFT world. And so I'm working very hard to create the standards along with the horological societies in New York to determine what the protocol is going to be for all watch
Starting point is 01:11:50 NFTs everywhere. And I'm very fortunate to have some of the largest collectors in the world as my partners in this. And they have huge collections as well, as well as some of the thought leadership in the watch industry. So we're negotiating now what that protocol is going to be and then we're going to develop it. And then if you have a watch and you want to create an NFT, you'll be able to do it with your phone. We'll give you the app to do it, but we'll tell you exactly what the protocol is going to be
Starting point is 01:12:14 to make it have the check mark that it is approved as the true watch protocol NFT. That's just one use case. There's so many others. And I think NFTs will actually become bigger than Bitcoin. The value inherent in the NFT market in a few years will outstrip whatever Bitcoin's going to. Each of your watches have a particular number on them.
Starting point is 01:12:36 They're all numbers, so you know what they are. Are the watch companies pushing back on this and saying, well, you don't actually own the rights to use those particular watches in different formats. For example, I own a Mark Bradford painting. I would love to sell a non-fungible token for that painting, but that isn't going to fly in the art world. There's all kinds of people who are talking about that Mark will retain the copyright on the image. I can't reproduce that image. It's why you see in the auction catalogs when the sale is finished and you go to look for the painting online,
Starting point is 01:13:09 there's a gray box there. Yeah, you're right. That negotiation is occurring between all of the manufacturers and our group. And we plan coming up with some solution because in the contract itself, in the smart contract, depending which blockchain we build it on, Ethereum is not optimized for everything. It's quite slow. And so we're looking at other options as well as Ethereum. But one idea is to do this. If you allow us to make the NFT at the point of origination, in other words, when the watch first leaves the factory, that piece forever will pay you royalty every time it trades hands in perpetuity while it remains a piece. So in other words, if you're a very unique watchmaker and you're only making 13 or 14 watches each year, you'll start building a revenue stream even after you stop making
Starting point is 01:13:59 watches because you'll be in the smart contract and your estate will be paid a royalty every time the watch trades. That's the likely outcome because the watch industry cannot make enough watches to fulfill the demand anymore for watches, particularly brands like Ademar Piquet, Rolex, Patek Philippe, FP Journe, Ming. They simply can't. If you order one of those watches, you may wait two years before you get it, if you ever get it. And so the NFT market will fill up the slack for those who really want to own the dials in a different way.
Starting point is 01:14:32 And I'm a believer. We'll find out. We're going to learn so much in the next 24 months. It's such an exciting time to be investing in digital. And I think it's terrific and very exciting and I think has tremendous upside potential. There's no question about it. Kevin, you're very impressive. I enjoyed learning about you. I really have watched the show forever. I love it. I actually really enjoyed this session. I do a lot of podcasts, but your style of
Starting point is 01:14:56 interviewing is very unique and very thoughtful. And I think you follow the strings very well as people explore their past. I think it's tremendous. You're doing a great job and I really enjoyed it. I hope the viewers will too. Thank you so much. And I just want to say one other thing. I came up to you. You didn't know me. You not only said yes, you gave me your cell number right out of the gate. I mean, that's incredible. I'm grateful. Thank you. Well, I recognize another entrepreneur right away. That was you. Awesome. We'll talk soon. Thank you. I appreciate grateful. Thank you. Well, I recognize another entrepreneur right away. That was you. Awesome. We'll talk soon. Thank you. I appreciate you. Take care. Thanks a lot. Bye-bye. Bye, Kevin.

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