Top 3 Tips That Changed My Life Forever

[Music] When I was graduating college, my mother came to the graduation. She said, "I've got great news! I'm coming to the graduation, um, but, um, I also have some other news: no more checks."

I said, "What do you mean?" Because she'd been paying for college and my rent and everything. She said, "The dead bird under the nest never learns how to fly." I said, "What the hell does that mean?" She said, "No more checks. I'm not writing any more checks; you're going to figure this out on your own. You know, I paid for your education from— I paid for you from birth. The last day of college, we're done."

And I thought, I mean, because I really had no job or anything, and I had a tough couple of years. I mean, I couldn't even pay the rent. But it worked out, and I got motivated. And, you know, obviously I'm pretty happy about the outcome.

So when I had my first big liquidity event, when The Learning Company got sold, it got sold for about 4.2 billion. There were 10 of us that were Founders. So we woke up the next morning and said, "We're rich!” Like, we didn't think about it; we came back to work and kept going.

But when I went over—that was in Cambridge—and I went over to Boston, saw the lawyers and said, "Look, I want to set up a trust that basically provides for my kids," because they were like four and six at the time. And, um, it pays for everything for them, um, until they finish college. And then they get nothing.

He said, "What the hell is that?" I said, "Well, it's a way that I can provide for them to set them up in life but not entitle them." I was taking a cue from my mother's strategy, same idea. And I went home that day and I told my wife I was going to do this.

I sat down with my two kids and I said, "Here's how this trust works, and everything's good until even if I get run over by a truck, you're good till you finish college." And they went, "Yeah, that's great!" They, you know, didn't give a about it—they were four and six.

So I can't believe you sat your four and six-year-old, but I had to disclose what I done. Years later, we're still in Boston, and my son is doing really poorly in high school. He is sucking and just not applying himself, and you know, his marks are terrible.

And the way to look at high school is it's just like a test to get into college—you gotta pass a few things. So one day he says to me, um, I'll never forget this conversation. Lyn and I were going out to a movie that night, and he says, "Hey Dad, one of my friends was telling me about his trust fund, and what does my trust fund look like?"

I said, "Well, I don't know about your friend's fund, but here's how yours works: if Mom and I get run over by a truck, you're good until you finish high school because it doesn't look like you're going to college." He said, "What do you mean?"

I said, "Well, the trust only pays till you finish college, then it's done." He says, "What do you mean it's done?" I said, "It means no more checks." And I said to him, "The dead bird under the nest never learns how to fly."

He said, "What the does that mean?" I said, "What it means is you should start thinking about taking advantage of this now. CU, you're not, and you're not. I don't know what's going to happen to you; you're not even going to finish high school here."

And I think at that moment that the lesson of life, you know, given to me by my mother, must—he saw the abyss, he saw the darkness, he saw the situation he was in and went, "This is bad."

And so he knuckled down, and he started getting into what he was into, and he eventually became an electrical engineer. He was at the top of his class all through, you know, college and right into engineering.

In all these electrical engineering cohorts, they all build a combustion F1 race car and an electric one, and they race them all around the world against each other because that's how they're learning if they're interested in electrical engineering or building that F1 Formula car.

Every year MIT would win 'cause they always built the best car. Well, in Trevor's case, he became the captain of the team, and he worked on the software that released the energy out of the battery in a different way, and he beat MIT.

So the Tesla guys came over and said, "Who are you guys?" And he went to college in McGill. He said, "We're the McGill team!" And he said, "You're all hired at Tesla—all of you, the whole team!"

Wow, that's where he works; that's where he lives—in San Francisco. Wow, that's the lesson of the dead bird right there.

Yeah, yeah, applicable advice, too. I'm going to do that. Yeah, yeah, because you can take care of them in health issues, but if you guarantee them a free ride, and they never have to take any risk, they won't, and you'll destroy their lives.

It's the worst curse you could do. Everybody knows people that have really screwed up rich kids, and they made that mistake—they just made it too easy for them. It's not going to happen in my family, and my trust goes, you know, in multi-generations. When he has kids, even if they're not married, it takes care of them till right at the end of college.

When I was in my final months of getting my business Masters, my MBA, in that class of maybe 160 cohort, you know, that was at that size, we thought we were such hot—I mean, you know, you're finishing, and you know everything, and you're ready to go and just take on the world.

And in comes this guy, and he says—he looks up; he was a guest lecturer—but usually guest lecturers, you know, get some slides up or start talking about a presentation about the company they're working for. He was different.

He walked in, no slides, no PowerPoint, nothing. He just walked around and looked at all of us. And he said, "You guys think you're so damn good, don't you? Well, when you walk out of here, the real world is going to kick the living out of you, and you won't know what hit you. It'll be brutal. About a third of you will be complete failures, another third will be spinning their wheels a decade from now, and the other third will be phenomenal successes. Too bad about the other two thirds, but I'm just telling you the truth."

And I looked down at him and I thought, "What an ass." What he claimed in that presentation was that experience is very important in life and that, in fact, intuition is just experience distilled.

The longer you're at something, the better your intuition is about businesses and people. And I thought, "What a load of crap!" Today I'm that guy. I'm that guy walking in those MBA classes at Harvard and MIT, looking at them and saying, "You know nothing, and the real world's going to kick the living out of you."

And I can't believe this has happened to me, but he was absolutely right. And so today, with all of the experiences I've had—all the Good, the Bad, and the Ugly, and all of the horrible things that have happened in the businesses I've invested in and all the euphoric ones and the amazing outcomes—that experience is distilled to intuition.

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 whether it's going to work or it isn't. I just know. I'm that good.

But he was right—the only way to get to where I am today is having spent 30 years doing it. It's the only way you can do it. You can't buy it. And so I really, really believe that about entrepreneurs and investing in them and supporting them. You need the experience that the road traveled gives you that turns into intuition, and that becomes a very powerful tool.

My journey started this way. I wanted to be a photographer or a cinematographer, and I was doing a lot of photography in school. I said to my father, "I'm going to make this my life."

He said, "You'll starve to death. There's so many good photographers you're going to have to compete with—so many good cinematographers, so many great editors. It's very hard to break out." I said, "Well, you're not being very supportive."

He said, "What I'd like you to think about doing is, because you don't know yet, why don't you go and get finished school, go into university, finish that, and then get a master's of business so that you have the tool set as an entrepreneur to choose any direction you wish."

And that was very good advice, because it gave me time to mature a bit and learn the things I needed to know about running a business. And then as soon as I got out, I went back to what I wanted to do.

I started a company that made shorts for the original six hockey teams for the networks. So, you know, we would run around all week shooting hockey players and coaches and teams in Detroit and Toronto and New York. And then we'd send it—I'd edit it—and we'd send it up to the satellite, and it would appear on Saturday hockey games. That was my first company.

We started producing Don Cherry's Grapevine, which is a format we owned. I didn't even know what a format was, but a format is ownership; it's IP in television. Then, another program called The Original Six.

Well, in a couple of years, the network started knocking in the door, saying, "We want to buy the company." And I said, "This is how it works—this is pretty good." So we sold that, and I started Softkey Software Products 'cause I'd met a guy named John Freeman, who did plotter technology with Osborne computers—very way back, CPM—and we founded that together.

I sold the software to giant plotter manufacturers because, back in those days, if you wanted to do graphs, they did it on a multi-axis plotter, and we had the controlling software. And Softkey grew into The Learning Company, which was the world's largest educational reference software company.

And we sold that one for 4.2 billion, and then I woke up with the, you know, founding team in Boston. We were in Cambridge, and I said, "Wow, we're rich! How'd that happen?" We didn't even notice it; we just, I'm not kidding, we just woke up one day and said, "Okay, what do we all do next?" We went right back to work.

That's what happened—so we didn't stop; we just kept going. And that was many deals ago. I've had many, many deals since then.