#27 A Truck Full of Money: Coding, Mania, Love, Genius: The Life of an American Entrepreneur

**David Senra** (0:00)
I want to tell you about a one time only limited event that I don't think you're going to want to miss. I am doing a live show with Patrick O'Shaughnessy from the Invest Like the Best podcast in New York City on October 19th. Patrick has interviewed over 300 of the world's best investors and founders for his podcast. I've read over 300 biographies of history's greatest entrepreneurs for my podcast. We'll be talking about what we learned from seven years of podcasting, sharing our favorite ideas and stories, and doing a live Q&A. There will also be special event-only swag. If you live in New York City, I think it's a no-brainer. But if not, I think it's a great excuse to fly in. I've already heard from a bunch of people that bought tickets, they're flying in from other cities. Some people are flying in from other countries. That's setting the bar really high, so I will have at least four shots of espresso, or four energy drinks, before or during the show, so we can make it a night that you'll never forget. If you're interested in attending this unique live event, I will leave a link down below. I highly recommend you get your tickets today, and I hope I get to see you in New York on October 19th. The voice from the podium called him back. Over the next six years, one in three of them would flunk out, the headmaster said. They might be the top seventh graders in Boston, but this was a school where even the best had to work hard. And that meant homework. Four to six hours of homework a night, said the headmaster.
Paul stared at the man. In his mind, he spoke to him.
Fuck you. I will never do homework.
There were things he would do, though, because he wanted to do them. He tried off for the school band and made the cut, and he also decided to check out the computer club. It had a faculty advisor and for a clubhouse, a windowless room down in the basement equipped with six terminals. They looked like TVs, but they had keyboards in front of them, which meant you could tell these TVs what to do, and that made all the difference.
Paul had never liked TV. He called it the stupid box. He would watch his father watching the evening news after a day at Boston Gas. His father would sit in his easy chair with a box of Cheez-Its and his Manhattan, looking at pictures of car crashes and murder victims. And Paul would wonder to himself why his dad would just want to sit and look at what somebody else wanted him to see, and listen to strangers tell him what he should buy.
So that is from the introduction of the book that I want to talk to you about today, which is A Truck Full of Money, Coding, Mania, Love, Genius, The Life of American Entrepreneur. And it's about Paul English, who is, I would say, best well known, or best well known? Most well known for his, for being a co-founder of Kayak, the travel search engine.
And before I get into the rest of the highlights that I found interesting when reading this book, there's an, like most books, they have an author's note at the beginning, and I was struck by the uniqueness of this one. So this is the author Tracy Kidder talking, and I just want to read this little section to you real quick.
So she's talking about Paul, and she goes, I had never heard him speak about his day job, but I knew it had to do with software, and that he was successful at it. So I asked him to show me around. After a while, I began to feel that my guide should become my subject. What I actually said was, why don't I write about you? And this is the really interesting part. It was sometime, months, I think, before he answered. I remember the moment well. He agreed with a proviso that I had never heard before in my years as a reporter and writer.
You have to promise not to make me look better than I am, he said.
So the reason I wanted to point that out is because this is a little different from some of the other books that I featured on this podcast in the past. And one of the reasons I love doing this podcast and reading these books is because so we all know the names of Henry Ford, Jeff Bezos, Elon Musk, all these people after the fact, after they were successful. But when you're reading biographies of them, you realize that they were just relatively normal people. And they all started from different, vastly different points, but you got to see them way before they were who we think of them now. And what I like about this book is, I would say almost half the book, so like in the title, it says, Mania. What they're talking about there is, he's a diagnosed, Paul's diagnosed with bipolar disorder. And so when he adds that little caveat at the beginning, it's like, okay, you can write about me, but you have to promise not to make me look better than who I am. Because there's a lot of stuff in this book that you realize even, it's really good, I think, for everybody to understand that, like, successful people are still just people. And a lot of them can be fucked up just like you or I. And in his case, like, you see him struggling with bipolar disorder for, you know, 30 years. You see some of the results of like his grandiose statements, some things that, you know, don't make him look that good. And yet he still sold, was able to found a company, was acquired by Priceline for $1.8 billion, and he walked away with $120 million. So I just want you to keep that in mind as we go through this book. Now, another thing, as I always do, I go, I'm reading the highlights and the stuff that's interesting to me, just to give you an idea of why you might be interested in reading the book. And I do try to read them in chronological order, but this book starts, it weaves back and forth throughout time. So just another, you know, I say this all the time, but it's not meant to summarize the entire book. These are just the parts that spoke to me. If you read it, different things might speak to you. But it might get a little confusing if you think it's in chronological because we start right at the beginning with, well, I'm going to read from the introduction, so I'm going to tell you about his first job, which is I always find interesting when I'm reading biographies of company builders. But then we're going to jump to like present day, which is like the day he makes the announcement of the sale. And you go back and forth weaving and kind of trying to kind of trying to tell his life story through all these like anecdotes and in store and like memories that he has, but they are not taking place obviously now. So this is his first job, and it kind of builds on what he was just saying that, you know, like most of the people that are on the podcast and most people that are feel they're like born to be founders or entrepreneurs, you know, they don't really like they have a problem with authority and they want to do what they want to do. And when they find something they want to do, they can be somewhat obsessive at it and that doesn't mean like taking up all your time, but you want to be good at it. So he's definitely the same way. So he's saying, hey, I'm not going to do homework, you know, forget that. But that doesn't mean he's a slacker. So let's go to the book for that. Paul was industrious outside of school. In seventh grade, his first year at Latin, that's Boston Latin, the school he's going to, he took $10 off of his paper route earnings and bought a dime bag of pot from the same man in the north end who sold the boys fireworks. Paul sold the dime bag bit by bit and with an with the astonishing profit, bought an ounce. Remember, he's in seventh grade doing this. In a corner of the attic, he found a small munitions box that his father had brought home from World War II. He broke off the lock and bought and bought a replacement at the drugstore, and he stored his drugs inside, mostly marijuana and also some mescaline. I don't I'm not familiar with that drug, so I don't know if I'm pronouncing that correctly. He hid the box in the eaves of the attic near his mattress. He never came close to getting caught. No one in the family knew except for Danny, this is his brother, who didn't get involved and didn't tell, of course. Paul quit that business after about a year. He could have bought, this is the most fascinating part, considering this is now happening when he's in eighth grade, he could have bought several used cars with his profit had he been old enough to get his driver's license.