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

What I learned from reading A Truck Full of Money: Coding, Mania, Love, Genius: The Life of an American Entrepreneurby Tracy Kidder --- [7:00] Kayak sells for $1.8 billion [12:00] "I'm paying attention. I want meetings of three people, not ten." [15:00] "Someday this boy's going to get hit by a truck full of money, and I'm going to be standing beside him." [22:30] A description of Paul's bipolar disorder [31:00] The economics of games [36:30] Learning how to negotiate from his Dad [43:00] "The Internet has massively broadened the possible space of careers. Most people haven't figured this out yet." [50:00] Leaving a $1,000,000 behind [55:00] Applying the lessons he learned from watching his Dad negotiate [58:30] The entrepreneur of ice [1:01:00] "Consistency doesn't matter. Only invention matters." ---- Founders Notes gives you the ability to tap into the collective knowledge of history's greatest entrepreneurs on demand. Use it to supplement the decisions you make in your work. Get access to Founders Notes here. ---- “I have listened to every episode released and look forward to every episode that comes out. The only criticism I would have is that after each podcast I usually want to buy the book because I am interested so my poor wallet suffers. ” — Gareth Be like Gareth. Buy a book: All the books featured on Founders Podcast

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Senra?

  "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 with 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.

• 0:42David Senra?

  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'd 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.

• 1:20David Senra?

  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? No. 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 a, 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.

• 2:07David Senra?

  So um, 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.

• 2:51David Senra?

  And one of the reasons I love doing this podcast and reading these books is because, so, we all know the names of like 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, says, "Mania." What they're talking about there is, uh, he's diagnosed, Paul's diagnosed with bipolar disorder. And so, when he adds that little caveat at the beginning, it's like,

• 3:36David Senra?

  "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 was able to found a company, was acquired by Priceline for 1.8 billion dollars, 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,

• 4:21David Senra?

  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 is, might get a little confusing if you think it's in chronological because we start right at the beginning.

• 4:45David Senra?

  With, well, I'm gonna read from the introduction, so I'm gonna tell you about his first job, which is I always find interesting when I'm reading biographies of company builders. But then we're gonna 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 kinda trying to tell his life story through all these anecdotes 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 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 wanna do what they wanna do. And when they find something they wanna do, they can be somewhat obsessive at it.

• 5:30David Senra?

  And that doesn't mean like taking up all your time, but you wanna be good at it. So he's definitely the same way. So he's saying, "Hey, I'm not gonna 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 of 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 the astonishing profit bought an ounce. Remember, he's in 7th 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 a replacement at the drugstore.

• 6:15David Senra?

  And he stored his drugs inside, mostly marijuana and also some mescaline." 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 8th grade. "He could have bought several used cars with his profit, had he been old enough to get his driver's license." And now, we're gonna jump ahead to the first chapter. And it starts, like I said, with he's making an announcement. He said, "We've actually agreed to merge with Priceline." He's talking to the whole company at Kayak now.

• 7:02David Senra?

  It says, "The crowd turned into, ooh, they said. Priceline was a large holding company of online travel agencies, and Kayak was a small and unusual, but very profitable, travel site." And the "very profitable" part is very fascinating to me, and I'm gonna get into that next. Might be the most fascinating part of this entire book. It's like, two paragraphs. "Until recently, it had done..." Now, they're talking about Kayak. "Until recently, it had done no booking. Rather, it was a comprehensive search engine for travel, often described as a Google for finding flights and hotels and rental cars. Paul and a young businessman named Steve Hafner had founded Kayak nine years ago in 2004. Since then, many companies had offered to buy them out, but Paul told the room Priceline's offer was the only one with the right ingredients. First of all, the purchase price is $1.8 billion."

• 7:47David Senra?

  He made the translation. "Kayak's stock was now worth $40 a share, $14 more than when the company had gone public just four months ago, and $10 more than the current price. Paul didn't say this, but about half of the people on his team own stock now worth at least $1 million, and some own considerably more. Paul's was the largest take, some $120 million."

• 8:14David Senra?

  So let's skip ahead. This is the part I really liked where it goes into the details. Because I knew obviously of Kayak the Business. I didn't know how they made money or anything like that. So they're talking about the office and their office is somewhere, I think it's called Concord, Massachusetts. So let's go into this. Concord belonged to what was now a mighty segment of new American industry. Mighty and yet utterly un-muscular looking. A stranger walking into this office, a stranger who, like most of humanity, knew little about software, would have to wonder what these eccentric-looking kids could possibly be doing to generate any money at all, let alone a fortune. Not for the stranger, but for his team, Paul had tried to offer an answer.

• 8:57David Senra?

  Programmers are always in danger of becoming happily abstracted from the consequences of their work. Paul had arranged to show his crew the fruits of their labor, a representation of the product's achievement, a representation in numbers, and an abstraction itself. A screen hung on the far walls of the second floor. One screen was large, big enough for an art house cinema. If you had looked up from your desk, say at 3:32 on the afternoon of November 7, 2012, the day before the Kayak sale was announced, you would have seen in bold type at the center of the screen this number. 2,737,926. Digits changed at stopwatch speed.

• 9:41David Senra?

  Two seconds later, the display read 2,738,816. No explanation was provided, but everyone who worked here knew that this number represented the day's running tally of travel searches. The searches, that is, that visitors had made between one midnight and the next on the Kayak website and the Kayak mobile application. Now, this is the really interesting part. There's only a few more paragraphs. As a search grew, let me do that over. As the search grew on the screen, you also began to understand Kayak's purchase price. The business worked this way. A user goes to the Kayak website, finds a desirable flight or hotel room or rental car, and then is sent to the website of an airline or hotel chain or car rental company

• 10:24David Senra?

  or to one of the online travel agencies such as Expedia or Orbitz. Kayak receives a fee from those other companies just for the referral. Seventy-five cents for a flight and $2 for a hotel, and considerably more if the user books the car or the room or the flight through one of those other companies. So every number added to the tally of searches conducted on Kayak was like a sale rung up on a cash register. Advertisements on the site, demure by industry standards, added more. Now, this is, I love this because they're actually showing numbers. In the course of the fiscal year 2012, Kayak's users made 1.2 billion searches. These brought commissions and ad revenues amounting to $292 million and profits of

• 11:09David Senra?

  $65.8 million. This is the most fascinating part to me, too. Remarkable figures, not for their size, but because only 205 employees had been required to produce them. In 2012, Kayak's revenues came to nearly $1.5 million per employee, one of the highest ratio among all publicly traded companies. So I found that really interesting. 1.5 million in revenue for each employee. So some of this is just, I'm going to pull out, obviously, like I've done in podcasts past, just little interesting ideas that maybe only last a paragraph that I think are interesting and might be helpful to you and I. Okay, so this is Paul on meetings.

• 11:54David Senra?

  Paul had made it a habit to glance now and then through the transparent walls of Kayak's conference rooms and spotting meetings that he thought were too large and too long. He would poke his head in this door, or in the door, and with a smile, always a smile, say he was sure that three of the dozen people in there were smart enough to solve the problem in half the time they'd already spent. He also bought a tally clicker, a device that nightclub bouncers use to keep count of patrons, and hung it outside the door of the main conference room. This, by way of saying, by way of saying, quote, "I'm paying attention. I want meetings of three people, not 10." And that's something we've seen from other entrepreneurs past.

• 12:36David Senra?

  The one that jumps out of my mind, it was when we talked about Jeff Bezos and his whole idea of keeping teams where you can feed him with two pizzas and no larger.

• 12:49David Senra?

  Uh, let's see.

• 12:53David Senra?

  Okay, so this is actually gonna, this, this, uh, I'm gonna skip over. This is taking place over three different pages, but only a few paragraphs on each. Just because I want to tell you, so I found this, I guess, let me back up. So a lot of the books I find are like recommendations of like other founders or entrepreneurs, or just Twitter, or podcasts, or anything like this. This is one of the first books that I actually found, just because I'd bought, you know, I buy a bunch of these books, all of my books on Amazon, and Amazon recommended it to me. And I'm like, it's, you know, kind of a clickbaity title, which I think is the whole point, where it's like a truck full of money, like what the hell does that mean? Because I'd never even heard of Paul English before this. So I want to tell you how the title came, uh, came to be, because I think it's actually really funny.

• 13:37David Senra?

  Okay, so, um, he's talking, they're talking about, just to give you some context here, um, he's, he's worked now at Kayak, he's in his 40s, right? But he's been starting companies for 15, 15 years at this point, and already sold a company previously. So he had a group of people that he'd work with constantly, and they'd work on a project, and then maybe that project would end, or in a failure, or in a sale, or something like that, and then go their separate ways, and then eventually Paul would have another idea, and he'd recruit them back and back. And this whole cycle went over a couple of decades. So he, they're talking about how on, with Kayak, he hooked, he basically set up his two lieutenants, Billow and Schwenk, um, to make sure that they were going to be financially independent. So it says, "Paul had made sure that both owned Kayak stocks in amounts commensurate

• 14:18David Senra?

  with need-to-have status, stock now worth nearly $20 million for each. Billow had prophesied something like this back in 1997," so now we're going to get to the title, "in the aftermath of the misadventure that Paul had led him on with the startup company NetCentric." And of course, a lot of, like anything, uh, Paul may have had two or three hits, but he probably had 50 different ideas, and maybe out of those 50 different ideas, maybe 15 or 20, um, actually started, whether they're an app, a division of a company, whatever the case is. And I think this is the most common thing that people that don't start companies don't understand.

• 14:52David Senra?

  That it's not about, I forgot how you put it. It's not like your batting percentage or slugging percentage, but basically like one or two successful ideas can pay for a lifetime of other failures. All right, so let's go back to this. So he's saying Paul had let him down on the startup NetCentric. So they lost their butt on that. Shrink had also followed Paul to NetCentric, and like Billow, he had soon quit. Then the two of them had started their own little software company along with an extraordinary programmer named Jeff Raggo. But things hadn't gone much better with that enterprise than they had at NetCentric. Their idea was to build internet-connected juke boxes that would serve as advertising devices.

• 15:37David Senra?

  The technology they created was first-rate, but it didn't sell. And then one day in 1998, Paul walked in. He was starting a new company, he told them, something called Boston Light Software. At this time, Paul's in his early 30s. Paul pitched the idea with his usual speed, his usual vigor, and certainty. They'd build a website for building websites. He had, again, another thing I think that is really helpful for me reading all these books, is you realize that ideas that are really successful, like think about WordPress and Squarespace now, how successful those companies are. Like their ideas, you see so many of the people had the same idea, but they might have been 10 or 15 or 20 years too early. So he's actually going to be somewhat successful in the Boston Light Software because he winds

• 16:20David Senra?

  up selling the company at the top of the dot-com boom, but I just think it's funny that we're reading in a book that in 98, he's like, "All right, I'm going to start a company that's going to be a website for building websites," because we have several examples of successful companies that have done just that now. He had a client already, and he was assembling a team of old colleagues, getting the gang back together. Billow didn't say much, but as he listened, he thought, "This is going to work."

• 16:44David Senra?

  After Paul left, Billow told Shrink and Lraghu, "Look, this thing's not going anywhere. We should go work at Paul's company." They said they wanted to go on with their startup. "I feel bad for leaving you guys," Billow said, but he was going, but he was gonna follow Paul. Fifteen years later, he remembered his words exactly. "Someday, this boy's going to get hit by a truck full of money, and I'm going to be standing beside him." Shrink and Rago had soon followed Billow and Paul to Boston Light, and about a year later, in 1999, Paul sold the company. He gave half of his own proceeds to his team and still came away with about eight million dollars. Paul was only in his mid-30s then.

• 17:25David Senra?

  This idea of giving proceeds away and splitting up half the money, it's really interesting to me because there's a quite of, there's kind of a, like a juxtaposition or a dichotomy, or I don't know the correct word I'm looking for, but basically, Paul is very good at creating software companies and making a lot of money, but he's very uncomfortable with being successful and there's a lot of, his ideas comes from the fact that he came from a family of seven kids and they were told that, you know, no one's ever supposed to be special, that you're all the same. So he kind of has like this residual guilt of being so successful, and so he has like a very strong communist streak in him. So he's like capitalist by day, and then once he's successful capitalist,

• 18:08David Senra?

  he takes the proceeds and he doesn't believe like hoarding money is that smart, so he gives a lot of it away. In the book, it goes into detail, and I'm not going to talk about it too much, but he develops a very strong relationship with a guy that was very successful and who has an interesting life story in his own right. Fought in World War I, came back to Boston, transformed his family's construction company into like this massive multiple hundred million dollar company, and then spends, lives to 90 and basically with the goal of dying broke. So he donates tons of money to Haiti and all this other stuff. So Paul does this too, like the book talks about all the stuff he gives, helps people with, and including homeless in Boston and charities in Haiti and all kinds of other stuff, but

• 18:51David Senra?

  you kind of see that even in his 30s, he kind of, you know, he has a...

• 18:56David Senra?

  I don't know if guilt is the right word, like, I mean, I guess it is kinda guilt. And we're gonna realize that a lot of the stuff that Paul does is not really easy to explain because, you know, he is, he suffers from mental illness. So I wanna actually touch on that, and I'm not gonna touch on too much of that because, like I said, a lot of the book is, is written about showing the bad, you know, the bad sides that even a guy with bipolar disorder, and we're gonna read some, I'm gonna read you some of the, like, how that manifests in Paul's life, but even people like that, like, as long, they, they're still capable of building companies and being successful in doing this. So, I don't know, like, especially, I've been thinking about this lately, where like,

• 19:37David Senra?

  you see, like, one of my favorite people just committed suicide, and you look at, like, the life of Anthony Bourdain, and you're just like, how is this possible? And you just realize that this, this problem of mental illness is, is everywhere, and it's hidden for most, for most parts. So, that's kinda why I selected this book now, there's a series of other books that I'm gonna be doing on the podcast too, I guess I could've done them first, but, that, normally I don't give a shit about, like, celebrities, I'm not into, like, celebrity worship, I think it's a downside to culture, human culture in general, but for some reason, like, I woke up to a text, and my friend's like, you know, Anthony Bourdain hung himself, and it just hit me a lot harder, because, you know, I've been following the guy's work,

• 20:23David Senra?

  I read his book, Kitchen Confidential is one of my favorite books I've ever read, watched all his shows back from like 2006 on the Travel Channel, and it's just like, I wasn't expecting to, to deal with this emotion, it made me think about, like, how many other people are, you know, because you, you ask anybody what kinda life you wanna live, like, you know, he got to travel the world, make great content, meet interesting people, eat great food, like, he was loved by millions of people, and it's just that, none of that matters. It matters how, like, how you feel about yourself, and he was deeply, obviously deeply oppressed, and, you know, he had, he'd been open about it, he'd been talking about, like, I remember reading one of his quotes, he's like, "I never knew anybody else that wanted to die as much as I have," like... So I think this is appropriate because I think people in general struggle with it,

• 21:06David Senra?

  but I'm sure founders do. You always hear, like, not you don't always hear, but you hear some of these examples of like, you know, like, the pressure to like, act like everything's always going well, and some people like, feel they're living two different lives, and I've even read stories of, you know, people that their businesses fail, and so they kill themselves. And you also saw that in different cultures, like, finance industry, like, when you have crashes like Black Friday, or whatever the case is, people jumping up buildings. And so, um, I, I, I think that's a big problem. I don't think you, I think you, we have to do whatever we can to disassociate like, how we feel about ourselves, or like, whatever is going on in your professional life, even though they kind of, it's really hard to like, based on like, I just, the fact, all the entrepreneurs I know feel like it's part

• 21:49David Senra?

  of your identity, you know, as opposed to most people have a job. It's like, oh, I go to my job, and it's like, there's no, it's like a clear cut. If you have a job, you go home, and you're doing hobbies, or you're spending the weekend doing whatever you want, like, I don't know if founders have that, so they might be more prone to it. So, um, if you are like, struggling with any of this kind of stuff, I definitely read this book, because, um, there is a happy ending here. And, uh, so I rambled enough, and I wasn't expecting to even say that, but I saw my note, and it just, that thought popped in my head. So, this is a description of Paul's illness. And, um, this hyperactivity is, is called hypomania, I think. I don't know if I'm pronouncing it correctly, but they're gonna talk about that, too. "Hyperactivity was likely just a symptom of his deeper

• 22:32David Senra?

  problems, his bipolar disorder. The general term denotes what used to be called manic-depressive illness, now broadened to include intermittent, alternating, and sometimes mixed states of depression and mania." Mania, mania, mania. "Varying wildly in kind and severity. In the past, Paul had suffered from near-immobilizing depression, but not from the psychotic states of full-fledged mania." So, what they're saying here is, uh, suffering from near-immobilizing depression. There's a lot of times, like, this is interesting, where, what triggers this, too, where he would just wake up, he can't, he'll sleep for like, two hours, and then he just stares out the window till the sun rises, so he can get his day going. And

• 23:14David Senra?

  sometimes this is happening when he's having, like, uh, he's having, like, trouble in his professional life, but more interesting is the sale of kayak, and that huge success being written about in the Boston Globe the next day, triggers...

• 23:28David Senra?

  Him to go into like a D, he spent a weekend basically not moving, not being able to sleep. Which is again, I think, from the outside looking in, which is a very inaccurate way to look at things, unfortunately. Most people would probably think, "Oh, this guy must be on cloud nine." And in reality, he's at his lowest point. Okay.

• 23:48David Senra?

  Okay, so, "He suffered from neuro-mobilizing depression but not from the psychotic states of full-fledged mania, in which one is consumed by delusions. He was subject instead to the oddly vaguely-named hypomania, which means "less than full-fledged mania." "The labels are kind of dumb and meaningless because no one really knows how the mind works," Paul once said. "What's really important is, what are the symptoms you're having, and are they that bad? And then, what things can we do to make those symptoms be less?" He called his current psychiatrist and found a drug, an epileptic called Lamictal, that had kept Paul's depression mostly at bay for a decade and with minimal side effects. But his bouts of hypomania, his highs, recurred. So I just want to interject real quick before I go back to the book.

• 24:33David Senra?

  So, they name, I don't, I'm not gonna read them all to you, but there's probably a dozen different medications throughout his life that he's on. And they talk about the side effects in the book too, which is...

• 24:45David Senra?

  I've never taken any of that. I try to like, live clean as much as I can. And definitely nothing like, pills, like I'm just not into that shit, but um... I obviously, I've never been, you know, clinically depressed, I'm not trying to make light of that, I'm just saying that like, it was jaw-dropping to me because I've never had him put on medication. And what, even like, he talks about what like, 5mg can do to him, it's pretty crazy, so. Again, if you're interested in that, buy the book. "But his bouts of hypomania and his highs recurred, at their apex," now this is interesting, "when he felt on fire, he was prone to what psychiatrists and therapists called grandiosity. Then everything seemed possible," when he's, they're talking about when he's on fire,

• 25:28David Senra?

  "then everything seemed possible for him and the success of every new venture assured. A hypomanic high could also be lonely and irritable state. As when everyone seemed too slow to understand him, he'd stare at people who were talking to him, straining to be polite. 'That's pretty funny,' he would say, while thinking, 'You just made my blood pressure go up because I just lost 3 seconds that I'm going to beg for on my deathbed.' Often during highs, he gave away a lot of money." More important, he scarcely rested and sometimes used alcohol to calm himself. And that's again, going back to what he said, don't make me look better than I am. He drinks throughout this entire time and almost every single drug that he's on, you're not supposed to mix with alcohol.

• 26:11David Senra?

  So again, he's not really hiding his flaws from you. This book definitely isn't. Okay, so he scarcely rested and sometimes used alcohol to calm himself. And a high could lead to his sleeping with someone he later felt he shouldn't have. When he returned to a quieter state, his fires banked for a while. These risks were clear. It's bad for money and sex and for drinking. But as a rule, hypomania took away his ability to resist it, even when he was aware of being in its grip and mindful of the risks. In Paul, the highs tended to build in intensity, sometimes over hours, sometimes it seemed over months. Usually, a set of physical sensations told him the full-blown thing was arriving.

• 26:56David Senra?

  Now, this is going into his actual effects and the description of the physical manifestations of his illness. He would feel a tingling in his arms and hands, then blood racing through his arteries and veins. The colors around him changed, sometimes to lurid hues, and he felt alert to everything. He was reminded of the commotion of feelings that came flooding over him in the moments before a traffic accident. But the sensations around accidents soon subsided. These lasted for hours, sometimes for days, rising and ebbing and rising again. The overall feeling struck him as bizarre, as something that his body wasn't meant to feel, an uncomfortable state when he had first experienced it years before. Now, when he sensed it coming,

• 27:38David Senra?

  he felt both a little frightened and thoroughly exhilarated. In one email he wrote, adrenaline, period. Hard to sit, period. Mind racing, period. Thrill, period. It feels good. In another, if someone invented a drug, this is a quote from him. If someone invented a drug that normal, normal people could take to feel like I feel this morning, the inventor would be a billionaire. On one occasion, he said, "I love the highs. I can feel the blood racing through my veins and I get a lot done." In the midst of a high, he was apt to wonder what it was that needed to be cured. He knew, he knew this in his quieter times. Another quote from him. "It's a funny thing about mania.

• 28:21David Senra?

  It feels so good that when it is with us, we feel cured, perfect, and we don't want the meds anymore." What he's speaking to there is not only was he prescribed a bunch of different medications, he routinely just jumps on and off of them as well.

• 28:39David Senra?

  So I'm going to skip over the, the chapter that I'm in currently goes, keeps building on that, but I think that that's a good highlight to give you an understanding of like what, you know, what he's going through.

• 28:55David Senra?

  Okay.

• 28:59David Senra?

  So this is now they jump forward and, and the timeline I get a little bit. And now we're kind of seeing the downside of even though he, the sale to Kayak goes through, he has, he makes 120 million. He, this is the note I left to myself. It's tomorrow morning when I wake up, I'm now an employee.

• 29:21David Senra?

  This is a direct quote from Paul. "As of tomorrow morning when I wake up, I'm now an employee." Since then, he had given some bursts of energy to this new role, but it had been weeks since he had talked about finding a new office in Cambridge for Kayak or about the video wall or about much of anything else to do with Kayak except to say, "I have to show my face there once in a while." So the, the new office and the video wall, he had all these ideas and he's constant ideas. They list probably a hundred of them in, in the, in the book. And it's a way to like get him excited and keep forward momentum, but he's kind of getting a little depressed here. "Then one morning, he drove out to Concord to give one of Kayak's vice presidents a routine quarterly evaluation. Then the VP asked, 'Paul, can I give you some feedback?'" "Sure," Paul said.

• 30:05David Senra?

  Uh, how many hours a week do you work at Kayak lately? "I don't know," said Paul. "Twenty?" "Try three," said the vice president. Paul didn't believe it, not at first. But when he looked around the office, he realized, to his dismay, that there were now new young people there whom he didn't know, whose names he didn't even know. When and how could have this happened? It took him three weeks to act. So we kind of see, he's very excited to be running Kayak, gave Kayak nine years. Once the sale goes through and he's just an employee, he's not meant to be an employee. And he completely becomes disinterested. And in this case, he's working about three hours a week. So he makes a change.

• 30:48David Senra?

  Okay, so now I've skipped ahead a little bit. And this, like, page, it's about a page long. I found really interesting because it's the economics of games, video games. So his older brother becomes a computer programmer and a game designer. And I love that book that we talked about on the podcast, The Master of Doom. John Carmack and John Romero and the beginning of Doom. And then what I loved about the book is also the, like, they go over, you know, how much money the games were making. And it's just a really interesting, for me, the most interesting part, one of the most interesting parts. So this is the economic of games. And I think this is, I want to say this is in the 80s? This is all happening? Somewhere around that time. So, uh, let's just, let me just go into it.

• 31:33David Senra?

  During Paul's senior year at Latin, his brother Ed became a celebrity in the world of electronic games. Ed had left home and spent a year writing a chess-playing computer program for a company in Florida. It was a hit, and Parker Brothers had brought him back to New England and given him the task of converting a Japanese arcade game called Frogger into one that could be played at home on the Atari 2600 video game console. A difficult assignment, first of all, because Atari didn't want other companies producing games for its device, which meant that Ed, with the help of a colleague, had to reverse-engineer the Atari console to figure out exactly how it worked. More daunting, Ed had to reproduce Frogger in a program that would occupy only a smidgen of memory.

• 32:16David Senra?

  He pulled it off in just six weeks. His version of Frogger was the first electronic game accompanied by a two-part harmony music. He called the experience "an Olympic trial for game making and the finished product by Mona Lisa." Parker Brothers priced Ed's version of the game at $20 per cassette and was already shipping four million copies. Let me read that part again, because I'm reading it as a run-on sentence, it's not. Parker Brothers priced Ed's version of the game at $20 per cassette and was already

• 32:56David Senra?

  shipping four million copies to retailers when Ed bought a cassette over to Purhame Street to show his masterpieces to the family. So I guess that's the street they lived on. He set up the equipment on the kitchen table and everything was going well until Paul started fiddling with the controls. The next thing Ed knew, the game went haywire. What's more, Paul was able to make it malfunction again and again. Here was Ed's baby's brother, whom Ed had only known distantly and mainly from contentious games of chess, which Ed, to his chagrin, had usually lost. And now this teenage version of that irritating prodigy had found a bug in Ed's Mona Lisa. Ed was furious.

• 33:40David Senra?

  "I could have killed him," he said, and then he was scared. The code for the game was contained in ROM, read-only memory chips, which could not be reprogrammed. For some time, Ed waited to hear that others had found the bug and were returning their cassettes, but no one ever did. Parker Brothers, having sold all four million of those cassettes in a year, offered to pay Ed $50,000 for every game he programmed thereafter. Instead, he does a smart thing here. Ed quit and started his own gaming company and soon afterward brought a brand-new Porsche and a house on the waterfront, south of Boston. So what I really found interesting about that is not only that Paul was able to find

• 34:21David Senra?

  a bug no one else did, but look at the why, if you can, at all possibility, work for yourself is they're selling four million copies, $20 a pop, right? And that's, my math is 80 million on that. Okay?

• 34:38David Senra?

  Eighty million dollars and they give, they offer Ed, the guy that created what they sold for eighty million, fifty thousand dollars. That just blows my mind. Alright, skipping ahead, here's just a great quote, as I've said before, I'm a sucker for aphorisms and pithy little quotes and just general truths that can kind of be expressed in, you know, a sentence or two. So this is one I highlighted, "One rather curious thing I've noticed about aesthetic satisfaction is that our pleasure is significantly enhanced when we accomplish something with limited tools."

• 35:23David Senra?

  Okay, and on the very next page, we find out why Paul falls in love with programming. He learned how to program when he was really, really young, I think seventh or eighth grade, and then kind of just forgot about it for a few years. And so, this is, he picks it back up. "He was witnessing amazing things and also making them happen. Now and then he would hear sounds of the life, the sounds of the life of the house." Remember, he lives in a house with seven kids. "The pipes to the water heater would start thumping, or there would be footsteps in the kitchen overhead. Upstairs, all the emotions of a big family were swirling around. Arguments, many competing sorrows, and there was nothing he could do up there to change what worried and upset him. But he could always figure out how to tell the computer to do what he wanted, and it

• 36:08David Senra?

  didn't argue back or ignore him. In his basement room, it could be of any time of day or night, and when he was coding or watching a message being painted on his screen, he felt as though there was no other time than now and no other place but the small universe he was creating in his current program. A place where he was in charge. A refuge inside a refuge."

• 36:35David Senra?

  Skipping ahead, this is actually really interesting, I highlighted it. And then you realize, it's how he learns how to negotiate from his dad. You gotta remember this part because at the end, it comes back. And it's just fascinating. Well, let me just read it to you. "By the time Paul became a regular on the buying trips, his dad was mainly dealing in window-mounted air conditioners. Much easier for a man with an aging back to lift and put in the car." So his dad would never sit still, worked very hard. And so he finds a side hustle, he has a really successful job at Boston Gas, climbs the ranks, and on the weekends he goes to like gas, not gas, garage sales and the like, and picks up things that he can fix

• 37:19David Senra?

  because he didn't believe in ever letting anybody else do anything for him, and then resells. So we're gonna see why this is important now. "His dad's general scheme was to buy the ACs in the late fall or winter, repair them when he had the time, and wait until the hot days of summer to sell them. He made many of his purchases at yard sales. Paul studied his techniques, saying his dad, say his dad liked the looks of an air conditioning unit on sale for $100. He'd go up to the owner and he'd start by cracking a joke. Maybe the seller would say, by way of claiming that the AC unit in question was virtually brand-new, "I bought it for my aunt and she passed away." Paul's dad would smile, "Well, she probably needs air conditioning where she is now." Paul imagined the other party thinking, "Who is this guy?"

• 38:04David Senra?

  His dad was trying to catch the seller off-guard, Paul thought. Then right away, his dad would name a price, always a crazy number. "I'll give you $3 for this piece of junk." And surprisingly often, the seller would say, "Oh, I guess." To Paul, it seemed as if, as if having been thrown off balance, the seller needed something tangible, like a number, to get steadied.

• 38:35David Senra?

  Okay, so before, when he's in college, he thinks, he doesn't think he's gonna be a programmer. He's just, something he does. He thought, he, he thoughts, he thinks he's gonna be a musician. So this is the transition from how he gets from musician to programmer. And this is when he's in college. At the next session, the instructor unveiled his code, writing it out boldly on the board. Peering from his back, his seat far back in the room, Paul saw that his own algorithm was shorter than the professor's. It would do, it would do the job faster, he thought. He was surprised and he was pleased. "I'm way smarter than this guy," he thought. And then he thought, "I could do this, I could do pretty well at this stuff." He took most of his classes at night and many in computer science as he was allowed.

• 39:20David Senra?

  During the days, he worked full-time at a string of programming jobs, seven years long. Soon enough, he realized that in spite of his first impressions, the computer science faculty at lowly UMass Boston deserved his respect. Some were still in the midst of distinguished careers and most had practical experience at companies. Unlike many computer science programs, theirs focused on not, theirs focused not on theory, but on the actual engineering of software. Paul's jobs, his day jobs, added up to a supplemental course, like clinical rotations in medical school. In his first programming job, Paul was hired as a temp doing menial chores, but ended up rewriting the company's administrative software.

• 40:05David Senra?

  He had wanted to learn what off, what office work was like. After about six months, he quit and signed on at a medical device company where he wrote a program to control a centrifuge. He also spent a year and a half with a defense contractor writing software to control high-speed, a high-speed camera in an air force spy plane and a user, user manual to go along with it. Remember, he's doing all this while he's taking a full course load at night. And another year and a half at the mini-computer company Data General, where he performed coding jobs for a team of computer scientists with PhDs.

• 40:39David Senra?

  So, he winds up realizing, "Hey, I'm really good at this. I'm gonna do this for work." He gets his PhD. He's still working. He's taking his PhD in computer science and he goes work for an old colleague at this place called Interleaf. I don't know if I even talk much about that. I don't think I do, but he has a bunch of successes, not only as a founder, but before that, as a... He works his way up the ladder and becomes a programmer and executive, etc. So, this part, though, I'm gonna skip ahead, and it's interesting because it's a description of the work, and I think why he realized he was drawn to it.

• 41:19David Senra?

  "What he later called the 'social niceties' didn't come easily to him, but that didn't matter with computers. Exploring them didn't require that he deal with other people and their complexities. Writing software seemed to occupy a place between pure mathematics and the experimental sciences, between the search for a platonic ideal and the search for theories that jibe with observations of nature. He referred to writing software as 'this funny business.' It was the creation of something 'notional/fictional/imaginary' that nonetheless had tangible effects. Coding was infinitely precise and yet imperfectable.

• 41:59David Senra?

  Programs got written and revised until they did their jobs as well as possible. It was a field for people who liked the idea of 'good enough' instead of 'perfect,' the idea of 'play around in your head' instead of 'play around in the mud.' If your program failed, it was because you hadn't tried hard enough, not because information was withheld or missing. Programming computers felt like entering a universe unto itself."

• 42:32David Senra?

  So now skipping ahead, I mentioned earlier that Tom becomes friendly with this guy's much older than him, or excuse me, Paul becomes friends with this guy named Tom, who's much older than him, and he's the one that came back from the war, and builds up this super-successful construction company, and then decides to give away all his money, right? So there's this part where they spend, the book spends a good amount of time talking about Tom, because he's fascinating in his own right. And so Tom grew up in Boston, he went to Harvard in 1930s, and he talked about, like, he was from like a real blue-collar background, and he had, I guess they had a, like, a section of Harvard at the time, where, like, people that were not of, like, blue blood, or whatever you want to call it, basically hung out.

• 43:16David Senra?

  And so back in the 30s, he felt like, you know, less than. He felt that, even if he was as smart as some of the people there, because he didn't have, like, their upbringing, that he was somewhat inferior. So, in the section I'm about to read to you, Tom is talking about running into a Harvard classmate of him, and now they're way older, right? So this is, I think they're 70s or 80s, or something like that, maybe 90s. And, well, let me just, let me just read it, and then I'll get to why I included this. So, Tom's talking about this guy named Sandy. Sandy was a class of 1932 at Harvard, handsome guy, a real Brahman, just like the Cabots and the Laowls, they spoke only to God.

• 44:00David Senra?

  I guess that means coming from, like, prestigious families. "The last time Tom ran into Forbes," because that's Sandy's last name, "the man was pushing 90. He said to Tom, quote, 'Things change as you go through life, and we don't feel about you people the way we used to,' end quote. You people.' By then, Tom wrote, he only felt, he felt only amusement. 'One can overstate the exclusionary power exercised by Boston's Anglo-Saxon elite. There had long been ways for a young Irish Catholic to rise. Tom had found one in construction. In my business,' he liked to say, 'all you had to do was be the low bidder.'

• 44:41David Senra?

  There was politics, of course, and thanks to recent economic history, there was another, uh, this is the part why I included it, there was another, uh..." And thanks to recent economic history, there was another and broadening route up. The technological exception. You could have the wrong accent and no table manners and be possessed by psychological oddities, or worse, so long as you belonged amongst Knuth's 2%. Is it, he's referring to Donald Knuth? Maybe it's, it's, his last name's spelled K-N-U-T-H. They also talk about him a lot in the book. I don't know how to pronounce his name, but he has a theory that only about 2% of humans are actually born to program computers, because you need these, what he's called, psychological oddities. So he says, "As long as you belong to Knuth's 2%, born to program computers."

• 45:26David Senra?

  Enthusiasts imagined the digital technologies would serve as a great democratizing, equalizing force. And that's the last of, part I highlighted. And when I read that section, I, it made me think to this, um, this tweet I saw on Twitter by this guy named Naval Ravikant, who's, uh, he's a really interesting thinker, and I think a lot of people know him because he's the founder of Angelus. And this is his tweet, and I just want to read it to you. "So the internet has massively broadened the possible space of careers. Most people haven't figured this out yet." And I think to people that are interested in technology, or in general, think that, you know, it's, it's really widespread, but a lot of people don't even think that.

• 46:07David Senra?

  And I kind of agree, I do agree with what Naval's saying, is like, the possibility of jobs and things you could do and things you can create is just so much broader than, if you look at this. They thought the only way to succeed in Boston was coming from a right family, going to, you know, going, basically doing the same careers, going to the same schools, and you see this like, this upbeat-ness, which is so stupid to me. It's like, oh, you know, things change as you go through life. We don't feel about you people the way we used to. It's like, you people, like, this guy served, he won a bunch of honors in, uh, World War I, builds this giant massively successful company, gives all his money away, like, I don't give a shit if you're from some blue-blooded family, like, what, they're, like, you didn't do that. Like, I, it is so weird to me how people are like, proud of things they had no control

• 46:52David Senra?

  over, you know? It's like where if you have to create something that helps people or you build a company, something you actually did, and that's where they're being proud. Being proud because you were born into like a royal family, like that's pure luck. Like I don't understand why you'd be proud of that. So, and I just like the fact that we're alive in a time where, I do agree with this, like enthusiasts imagine that digital technologies would serve as a great democratizing, equalizing force. And you're kind of seeing like the balance of power and wealth and not even even at the highest levels, like just being able to provide for your family or enjoy what you do all day. Like the internet made this all possible in a way that if we were born 50 or 75 years ago, the route, our route would be vastly different.

• 47:34David Senra?

  And I don't know, I find that really inspiring and if I just, I don't know, I love that idea. Um, okay, so where I'm gonna talk, skip ahead now. Okay. So this is how he becomes diagnosed as bipolar disorder. And again, the, the book is going forward and backward through, through flashbacks and memories and then bringing you to present day and kind of pushing the story forward. But since I'm not reading in, in the entire book, it may be a little confusing. So we're gonna go back to when he is now at interleave. So he's already got his PhD, he's probably what in his twenties now, you'd figure, maybe early to late twenties. But before he starts Boston Light, which is his first successful company.

• 48:18David Senra?

  And this is how he figures out that he's diagnosed with bipolar disorder. And again, because I think this is important, um, just more of the details. "There were days and parts of days where he had to struggle for civility. This happened most often when he had to go to meetings. There would be five people in the room and he would try to explain what he was doing with his code and no one would understand. He'd think, what are they stupid? How much do I have to spell this out? They can't go from A to C? Some of those times he felt as if he were back in elementary school. Teachers asking him, would he please explain how he come, how he'd come up with the answer to a math problem so quickly and feeling both irritated and puzzled? He would, and feeling both irritated and puzzled, he would reply, it's obvious."

• 48:59David Senra?

  Sometimes in the meeting rooms at Interleaf, this is the company he's working for, it seemed as if the uncomprehending others were ganging up on him. And what he felt then was anger. Sometimes he let it show. And this is quote, and again, I think this goes back to like what the author's note said, that he's not trying to make himself seem perfect. "Sometimes he let it show." Quote, "Do I have to explain every fucking step here?" End quote. After about six months of wild coding, Paul forced himself toward clarity. Something was happening to him and he didn't understand. It was a weekend, at this time he's married. He asked his wife to take him to the nearest big hospital. He didn't dare drive himself. The neurology resident told Paul that he had bipolar disorder.

• 49:44David Senra?

  Paul didn't want to believe it. But when he returned for a second opinion, the chief of neurology confirmed the diagnosis and prescribed lithium. Now, that's another drug he starts to get on. "The drug left a bad taste in Paul's mouth, as if he'd been sucking on pennies. And taking the drug meant acknowledging that he had this thing, this disorder inside him. He told no one at work. He stayed on lithium for several months, just long enough, almost, to forget how he had felt before. A friend came by his cubicle and asked, 'What's wrong with you?' 'Nothing,' Paul replied. 'You've lost all your energy,' his friend said. 'You sure you're not depressed?' 'Actually, I feel pretty flat,' said Paul.

• 50:28David Senra?

  Like, I feel safe. But afterward, he thought, 'I don't want to lose my energy.' He could deal with anything but that. He quit lithium at once."

• 50:41David Senra?

  So this is what I think many people might consider a mistake. The note I left is "leaving a million dollars behind." But again, we're going to see the difference of people, even if they're succeeding at a job, if they feel they're meant to run their own... Like work for themselves, then they're gonna do that even to drastic measures. So to give you some context, Interleaf, he's doing really well still. He negotiates, he winds up being promoted really high up. And it's a large company, a large stable company at the time. And he's got a fat salary and millions of dollars of options, some of which have invested. So, but he decides to take a leap. Paul saw unbounded promise in it and in the growing host of new online technologies. They're talking about the internet.

• 51:24David Senra?

  So he was disposed to listen when in 1995, the founder of a local internet-related startup began recruiting him. This was that fledgling company NetCentric. The founder pitched it as a 21st century phone company. Its first product facilities, now check out this idea for the product.

• 51:41David Senra?

  Its first product facilitates faxing over the internet. Businesses and law firms all relied on faxing for the rapid exchange of documents. But they were obliged to use telephone lines and the rates, especially for long-distance transmission, were still high. In principle, NetCentric could offer them a much better deal because faxes could travel over the internet for free. Two reputable venture capitalist firms and venture capital firms in Boston had already bet $5 million in the new company. Paul was offered the job of running engineering in return for a substantial share of the company's stock. Only half of his Interleaf stock options had vested. Quitting Interleaf now meant leaving a million dollars behind. He didn't care.

• 52:25David Senra?

  The move looked like a sensible step into the future. So again, in hindsight, it could look like a mistake, but leaving his comfortable job at Interleaf, going to startup, having that startup fail, and then eventually leads him to being able to start his own company and that one actually succeeds.

• 52:48David Senra?

  So this section is called "Three Years of Depression and Starting a New Company." He builds, at this time, NetCentric, after he leaves Interleaf, NetCentric fails. So he builds this, it's like this game, I don't, Shangji. So he builds, he learns this, I guess, kind of like Asian chess. I don't even know how to describe it, because I've never played the game. So he builds a forum, it becomes really popular. Yahoo makes him an offer for the website. He declines it, because they insist that he moves from California, he doesn't want to leave his family in Boston. So he's still really depressed, he's working, he saved up a bunch of money, so he could get through this time, but he's running out of money, and he's working like part-time

• 53:33David Senra?

  as a programmer, earning like eighty dollars an hour. And he gets, you know, he's just down on himself, but he kind of programs his way out of depression. But his gloom didn't last long. Soon after he turned down Yahoo, he had a chance encounter on a Massachusetts golf course, of all places, where he met a man who was working for the Boston Globe, managing the paper's online store. Soon afterward, Paul had a deal to improve the Globe's website, to make it a place where visitors could easily buy all sorts of Boston-related stuff, such as t-shirts, and snow globes, and sports team paraphernalia. The contract was for fifty thousand dollars, a contract for a product before Paul had a company to build it. He had a name, though, Boston Light Software.

• 54:16David Senra?

  If all went well, he'd assemble a great team, and they'd build Boston Light into a website creator that would serve all sorts of giants' corporations, once they'd done their first job for the Globe. He had taken a step back to a former self. He had programmed his way out of depression. Now it was time to go back to work. Paul founded Boston Light in 1998, three years after he quit Interleaf.

• 54:41David Senra?

  Okay, so I'm gonna skip ahead. This is after he founds Boston Light Software. And do you remember that part where I said, "Remember when Paul goes, when he's a kid, and he goes with his dad on these buying trips and learns how to negotiate?" So this is him using, applying the lessons he learned from watching his dad negotiate to sell the company. The Intuit team, this is the Intuit company that's still around today, the Intuit team was suitably impressed enough that Intuit invested about $2 million in Boston Light and soon afterward decided to buy it. But what was the market value of a company only a little more than six months old with 15 employees and an unfinished first product?

• 55:22David Senra?

  Paul heard that another old colleague from Interleaf had just negotiated the sale of a small new company. Paul called him for advice. The old friend asked him how much he planned to ask. Paul said he wasn't sure. "Maybe 20 million?" "Ask for 40," his friend said. "40?" Paul said. "Boston Light didn't have any revenues," said Paul, "except for the 50 grand from Boston, the Boston Globe." His friend said to ask for 40 million dollars anyway. The Intuit negotiator was a woman. Paul liked her. He considered her a formidable adversary. He thought of her as, quote, "a cigar-smoking, whiskey-drinking," he thought of her as "cigar-smoking, whiskey-drinking tough."

• 56:06David Senra?

  As Paul remembered, she said, "Are you fucking kidding me? 40 million for that piece of shit?" She hung up on him. Paul called her back. "40? That's crazy," she said. He said, "I agree. I'm probably worth 100,000, but the market thinks I'm worth more, and I'm negotiating right now with four other companies." Just skipping ahead a little bit. Intuit's agreed, he's telling the people that work at Boston Light now, "Intuit's agreed to acquire us for 33 and a half million dollars," said Paul.

• 56:38David Senra?

  Skipping ahead to the next page, continuing the story, he goes to visit his dad. It was evening, and his father was sitting on the porch, taking in the sea air, facing out across the water toward Boston. He was an old man now, white haired and quite unlike his once forceful self, a bit fearful of the world. Paul had always felt wary of seeming boastful around him, but he simply had to tell him what he had done. "I sold my company, Dad." His father smiled, but when Paul told him the price, "Thirty-three and a half million dollars, Dad," the old man's smile vanished. He quickly glanced from one side to another. This was the man who once prided himself on never seeming phased.

• 57:23David Senra?

  "Who negotiated for you?" his father asked. "I did," said Paul. "You didn't have a lawyer do it?" "No." "How do you know about negotiating?" his father said. "Dad, it's exactly what I saw you do at yard sales."

• 57:41David Senra?

  I just love that part. Skipping ahead a little bit, there's not too much, not too many more highlights left. This is a short, really easy read, it's like 240 pages in the paperback version. So, I highlighted this part because it made me think of the podcast I did on Danny Lewin, No Better Time. And turns out Paul was actually booked on the same flight that Danny died on. Paul's greatest luck, his purest, in which he had no hand at all, came on September 11th, 2001. He and some colleagues had booked the doomed flight from Boston to Los Angeles, but at the last minute, they switched to a less expensive itinerant.

• 58:24David Senra?

  And this is another random part I loved, it's "The Ice Entrepreneur." I never heard of this before, and I love this. Paul's place by the pond had a curious history. The land in the oldest section of his house were once part of the estate of a 19th century magnate named Addison Gage, an entrepreneur of ice.

• 58:44David Senra?

  He harvested ice from Spy Pond and other locales and shipped it far and wide to America's warm southern states and also, according to one local chronicle, to the East and West Indies, to China, to India, and South America, and even Australia. Paul knew some of the history and would entertain guests with it, drawing a moral. "No matter how wacky an idea can succeed if it aims at a big market," all those hot places with refrigeration, "and if there are technologies to execute it: special saws, sawdust in the holds of sailing ships, insulated buildings." What vision the ice barons of New England must have had to look at the ice on Spy Pond and think,

• 59:28David Senra?

  "I could send this to India."

• 59:32David Senra?

  That just takes a lot of knowledge in that paragraph there. Um, skipping ahead, so after the sale of Boston Light, after Sale Kayak, um, the book spends a great deal of time on all these other ideas that Paul has. Uh, I'm not going to spend any time on it, um, most of which obviously don't work out, but uh, there is, he, there's probably one chapter where he lists like 10 or 15 different ideas and each one has a paragraph. And I just wanna, um, I wrote my little note to myself that I like this idea. So it's just a paragraph real quick. "There was good enough software, a nod to the way his father had of pounding in a nail and saying, 'That's good enough.' The idea sprang from irritation." This is Paul talking now.

• 1:00:15David Senra?

  "Microsoft keeps releasing a new version of Office every year. Who needs all those bullshit features? I would take the 10 most successful software apps and strip them down to the 20% most people use."

• 1:00:31David Senra?

  And the last from the book that I want to read, which I think is interesting. Um...

• 1:00:39David Senra?

  So this idea of the new economy, I think it echoes back to the podcast on the Michael Lewis book on the new new thing, which is about Jim Clark. And he was a very much a creature of the new economy and a like a new growth, I think it was new growth theory, was like a linchpin of the way he thought. So, and they're going to use the word like American, and I think that it's not just Americans that have this trait, but I just want to read this last paragraph to you. Paul was a creature of the new economy, but he was also an old American. He was a carrier of strain in the American character that refuses to be encumbered by the past. It's an ethos that says you don't have to do what your father did, that indeed you

• 1:01:24David Senra?

  don't have to do what yourself were doing six months ago, or even yesterday. Consistency doesn't matter. Only invention matters.

• 1:01:37David Senra?

  And I'm going to leave it there. If you want to get the full story, I'd recommend reading the book, obviously, that's why I did a podcast on it. A Truck Full of Money, Coding Mania, Love Genius, The Life of an American Entrepreneur. The great thing is, is if you want to read the book and support the podcast at the same time, you'll see in the podcast description and on founderspodcast.com. So what I do is after I'm done recording these podcasts, I obviously go back, like I said before, it's just a one man show. I pick out the books I'm going to read, I read the books, I do the highlights, record, edit, do all that other stuff myself. And what I do to make it easy, because I also, in addition to reading a lot of books, I listen to a lot of podcasts, and I leave like timestamps.

• 1:02:22David Senra?

  So I go back through after I'm done editing, and anything that like pops out to me, I try to leave like a timestamp. So if you see like the full description in your podcast player. You'll see, you know, it's just like two minutes and this is what I'm discussing in two minutes or like 10 minutes, whatever it is. So below all that, I put links to the book I've covered on this podcast and every single other book that I've covered so far. And so I keep adding to that list as the more podcasts I make. So if you want to support the podcast, if you like what I'm doing here, I don't really have, I don't interrupt it with any advertising. So at the end of every podcast, obviously, we'll tell you ways to support the podcast and if you want to help it out. And the best way, honestly, is just buy the books.

• 1:03:05David Senra?

  I'm doing this podcast because I think reading, people read more, like their lives are gen- like, it's just a way to improve your life. I feel like when you're focused on a story, especially when it could last, you know, from five to 20 hours, just completely different than I feel like these little hits of dopamine we get with all these social apps and staring at our phone all the time. So it's kind of like, it's a way, it's like my own, not anecdote, an- anecdote. You know, I can't pronounce any words. So the one where if you get bit by a snake, what is that called? Anecdote? All right, I think you know what I mean. It's my anecdote, hopefully that's the right word, to, you know, the like, the hyperactivity

• 1:03:47David Senra?

  we have with our, with our phones. When I'm reading a book, like, I feel like I'm in, paying attention, I'm in the moment and just spending a lot longer on a subject, I feel it's helpful for my mind. Especially like helpful if you need to take a long-term view of building a product or a service or whatever it is that you, you're working on or want to work on in the future. So if you want to support the podcast, click, use, buy the book using those links, those Amazon affiliate links, which means Amazon gives me a small percentage of the sale and no additional cost to you. So I think each book I get like 80 cents or something like that. And a bunch of you guys do this, so I really appreciate it. It's a great way to get yourself a book to read, which is the whole point of the podcast, and to support founders and help me do more of these.

• 1:04:31David Senra?

  So I'd recommend doing this, but honestly, buy them all. Or you don't have to just buy this one, buy a bunch of them if you want. The more books you buy, the better. The more support you're giving. So, and again, like, have you ever bought a book and regretted spending ten or fifteen dollars on it? Like, I just think it's a bargain for any book. Like, I was thinking about, so I do mostly shorter books. I try to do mostly shorter books for this podcast because, you know, a lot of these longer books that are eight hundred pages or something, they're just, I feel like, there's just too much fluff in there. But one book where that is the exception to the rules, that book Titan on John D Rockefeller that I covered, which is probably seven hundred, eight hundred pages, but it's like a twenty-five hour read. And, you know, I think you can get it for like fourteen dollars, something like that.

• 1:05:12David Senra?

  Like, where are you gonna get twenty-five hours of entertainment plus valuable, like, information? There's a quote in there, I kinda wanted to make a shirt, that it just stuck with me. And I think about it all the time when I, in my own day to day, and it's like, it's describing, it's the author describing John D Rockefeller, and he's like, "He was not one to persist in a flawed situation." And it makes me analyze and be like, alright, no matter how hard I work or how many hours I work, if I'm working on the wrong thing, it's a flawed situation and you shouldn't persist in it. And that just sticks to, sticks with me. And that alone was worth all the time, but the stories in there are just amazing. So, buy this book, buy any book that seems interesting to you, using the Amazon links

• 1:05:56David Senra?

  obviously will help me out very much, and I appreciate it if you do like and you get value out of what I'm doing here. Another way you can support the podcast is telling your friends about it. So, I see, I get some @ mentions if you wanna follow us on Twitter or interact or send me like a book you think I should do. Best way to do that right now is just, just tweet at me, it's @founderspodcasts, and just say, "Hey, this book might be good," or whatever. But a lot of you guys also, you know, recommend the podcast to your followers. So, that's super helpful because as, as the weeks go by, the downloads keep going up and more people are finding it out about this. One way is because listeners and people who are fans are emailing the link, or tweeting the link, or sharing it wherever they spend time.

• 1:06:41David Senra?

  And another way is because we keep getting, I keep getting reviews. I think I have a five-star average, which is fantastic, which means you guys are enjoying it. I also read them. I tried to avoid internet comments, but I do think that they're funny, and there's some good, like, it's interesting, because this is, you know, something I've created. I kinda like, everybody's been nice so far and I hope that trend continues. But the reviews specifically on Apple Podcasts and iTunes, I do read.

• 1:07:13David Senra?

  So you can also, if you want to leave a review there, make it five stars. You can also recommend other books, I'll read it and you can send a message that way. But what I'm saying is even if you don't want to buy the books, you can help by not spending another dollar, because I know everybody, you know, what I always say is like, I like to keep the podcast free for everybody. It's why I changed my mind on the whole Patreon thing, because everybody's in a different situation, so if your budget allows you to buy books, then buy books. If it doesn't, then you can still help out if you, if you want to spread this message. And the best way to do that is, is leave reviews. I'm sure you've seen, just like I have, even though I have three different podcast apps installed on my phone, and I do this to torment myself apparently. Apple is really, they're, they're, it seems like they're, they're getting more involved.

• 1:07:55David Senra?

  They realize that they have the single largest podcast app with the most listeners. And so now I'm seeing like it's easier to leave a review. They're starting to say, they're starting to like suggest different podcasts based on your listening experience. And I gotta take some time to read about this and I, I can't believe I haven't yet, but just the actual, the actual experience of the app is greatly changed. And they do seem to be like, for lack of a word, giving a shit. Since they do have, you know, the largest podcast audience. And I use Overcast, which I love, and Breaker, which I also love parts of. Overcast, I think is the single best podcast app built. And I like that it's just one dude doing it.

• 1:08:39David Senra?

  Breaker has interesting features. I don't like the whole social like liking things or like, I don't think everything has to have like a comment to. Like I think internet comments are probably the bane of our existence. Like, yeah, there's some good ones, but you have to go through probably a thousand comments to get to one good one. If you're, if you're talking about just random comments on the internet. And not opposed to people like you seek out. So, but Breaker is very helpful because it has this whole, I can see an entire history of what I listen to, which I really like, because I, I listen to podcasts over and over again. Because I use- Podcast primarily is like a tool for learning and they let me leave notes. Now, I leave notes on the podcast like I leave highlights in a book, which means quotes

• 1:09:21David Senra?

  at a specific timestamp. So I know what's taking place in that. I see other people like commenting on it. Like, I don't think that's a good idea. But it's not my app. They get to do whatever they want. I use all three of them. Point being is whatever you use, recommend it even Stitcher, anywhere you use. If you want to give reviews, it's really the best, uh, best thing. I really appreciate you guys taking the time and doing that so far and for the nice words. It's not necessary and very much appreciated. Um, the second one, so I'm going to ramble a little bit at the end of every podcast about how you can support the podcast. And it's not just like me reading ads because I'd be boring. It's me like talking about thoughts that I can't really include in the podcast. So hopefully entices you to stick around. If you don't want to, you don't have to. But, um, you know, there's just some ideas. So there's two other ideas I want to talk about.

• 1:10:06David Senra?

  They're both tied to other ways to support the podcast too. So I've talked about the app. Another way you could support this podcast is by subscribing to Blinkist. So if you go to blinkist.com/ founders, right? Um, you can go to that URL or like I said, in every, everything I talk about, links are always at founderspodcast.com. And I also include them in the podcast player app. So you never have to go to another website, but you can find them anywhere. So you can also find this link blinkist.com/ founders. You get 20% off of a yearly subscription Blinkist. And I think now they do monthly. But when I bought the app and I first knew about it, I did the yearly. Um, I think their feature request was like, hey, let's do this monthly. But I think yearly is probably the best way

• 1:10:46David Senra?

  to go. You save more money. But anyways, um, Blinkist is basically like, the whole thing of my opinion is like in the information age, there's like an abundance of information and we can't keep track of it all. Everything has to be shorter, more concise, more to the point. You know, I don't want, when I'm trying to pick out the highlights, I try not to waste your time, you know? So maybe I read almost all the highlights I do, but sometimes I reread it. I'm like, this isn't interesting in retrospect. So I try not to waste any time. So what Blinkist is good at is saving time. So they basically provide 15 minute summaries to over like 2,000 nonfiction books, right? So I think There's a lot of value in reading biographies because you understand the person and we're all people and we understand those messages. They can be like kind of mentors to us throughout time, you know.

• 1:11:30David Senra?

  Some cases like the book on Henry Ford I did, that book was written over a hundred years ago, yet that knowledge is still can affect my life now as I record this in 2018. So Blinkist helps with this because there's a lot of nonfiction books that just, they're just too, they're just, they're just too long. They're just, I almost said too fucking long. That really is what it is. They're just too goddamn long. And they have an interesting idea, but you can't, you know, maybe you could explain that, that interesting idea in a few paragraphs, but you can't really sell a few paragraphs, you know? So they wrap it up in this book. So I use Blinkist two ways. One, I find new books through it because I can, I have the Blinkist account where you can listen. You could, there's two different prices. One, you can just read the 15 minute summaries, but I like to listen to them, just like I listen to podcasts.

• 1:12:12David Senra?

  So I listen to it and it's usually even less time than 15 minutes, by the way. It gives me a good idea of what the main point is and if I like the point, I, and like I'll read the entire book. But some cases, I'm like, okay, that's an interesting thought. I don't need to go any deeper. I'll just retain that thought. So what I, what I want to share with you here is like, I'm going to read some parts about from this blink on this book I read a few years ago. So I've talked about on the podcast before, like I have a really like weird obsession with efficiency. And trying to like, get as most leverage out of my time and like, like, this is like a deep streak of like minimalism in me too.

• 1:12:51David Senra?

  Because I just want to focus on things that like, that are important to me and spend a lot of time doing that and hopefully get good at it and spend literally zero time on anything else. So what essentialism is, the subtitle is the disciplined pursuit of less. So it was a good book. It's 200 and some pages. I have, probably have, I don't know, 15, 20 different highlights in there. Interesting topography because like some pages are just one giant quote. And I think the guy's ideas is really important, but let me show you, I probably could have got most of that with just reading the blink. So here's some parts directly from Blinkist. This is their words. Essentialism, essentialism, which is the main, the main idea in the book focuses on four main points.

• 1:13:34David Senra?

  One, do less, but do it better. Number two, reject the notion that we should accomplish everything. Three, constantly question yourself and update your plans accordingly. And I put in quotation marks, a summary of that summary is be an editor. And then four, once the tasks have been reduced from the trivial, many to the essential, ensure that the changes you've made have put into place. So right there, in maybe what 25 words, whatever that is, that's the main thesis of the book. Now, there's some deeper dives I found interesting. They're also in the Blink. That's what Blink is called, the little summaries. Be ruthless in cutting away things that are not essential. And this is distilled, they distilled that thought down to one sentence.

• 1:14:17David Senra?

  If it isn't a clear yes, it's a clear no. When I read that, that made me think of one of my favorite, I guess a blogger, used to be an entrepreneur, I don't know how to describe him, but is this guy named Derek Sivers? You've probably seen him, heard him on podcasts and stuff. But Derek Sivers has a version of this where if it's not a clear yes, it's a clear no. He says, a great way to decide on what you're doing is if it's, when somebody asks you to do something or you ask yourself, it's either hell yes, like I'm super excited, I want to do this, or it's no. A lot of times we have this thing where like we say yes to be polite, or like we have an, like, oh, I don't know if I like that, maybe I'll go. And like, that's, time is all you have. So if you're wasting that, like, you're going to be frivolous in other areas of your life. So when I try to figure out what I want to do, it's like, yes, I absolutely want to do that, or the answer is no.

• 1:15:01David Senra?

  And for most things, you know, I'm passionate about starting companies. I'm passionate about being a good husband, a good father to my daughter, working out, being like physically healthy, so I'll spend time doing that, reading, listening to podcasts, and dinners, long dinners with old friends. And other than that, I say no to almost everything else, because that's what I get the most satisfaction out of life is. So that's kind of how I applied that. And all those things, I say a clear, like a clear hell yes, I want to do that. And I was listening to the Jaco podcast, and he made this good point, how like we just complain too much. And he's just like, why don't you just be excited, you get to wake up and improve tomorrow? You know, like, so when I get up in the morning, I'm like, wow, I get to like, make something

• 1:15:43David Senra?

  better, myself better, a product or a service, or, and it's just, that's a really good benefit of eliminating a bunch of shit from your life, because without all that crap, like, distracting you, you focus on the things you really love, and you're like, super amped up for what you're doing. And realizing that, yeah, there's going to be bad times, but like, stop being negative. Like, you have a chance to be better. That's amazing. You know how many people, like, the idea of like, if you were on... Your deathbed, what you would give for that time back. And we're kind of wasting it complaining or being sad when, you know, we just need a different perspective to operate from.

• 1:16:25David Senra?

  And when I, so when I read that blink, again, I try to collect all this stuff and kind of tie all this information together. And so I've talked about ad nauseam on this podcast. Like one of my favorite writers is Nassim Taleb. And he has similar thoughts with his concept of via negativa, right? So I saw a tweet describing via negativa without having to read some of, like as much detail as Taleb goes into, even though I definitely recommend reading his books because they're fantastic. So this tweet says, via negativa applied to your life. So via, it's, it's all about subtracting, which is what essentialism is, right? So I saw this tweet, via negativa applied to your life. When things are not adding up in your life, it's time to start subtracting.

• 1:17:11David Senra?

  When you stop doing the wrong things, you give the right things a chance to catch up with you.

• 1:17:18David Senra?

  So remember that when I talk to you about a book I read in a few minutes from now. Okay. And then finally, the end of the blinks usually end with like a key message and they try to distill it down even further. And it said, the key message of this book, talking about essentialism. In spite of how it might seem, only a few things are actually vital to our goals and wellbeing and everything else is unimportant. By focusing on these few essential things and learning to do better by doing less, we can craft a life that is more productive and fulfilling. So right there, I spent 10 minutes, I spent hours reading the book. Based on reading the book, I'm telling you, you got, you got 90% of the important parts in 10 minutes and blink, and the blinks. That's why I think this is so important because where there's, if you calculate, okay, maybe you read 10 books every year and maybe you're 30 years old.

• 1:18:02David Senra?

  You can expect to live another 50 years, but that's only 500 more books. That's not actually a lot considering there's millions, hundreds of millions of books out there. So we have to be really smart about how we apply our time. And the reason I recommend this app is because that's what it does. It saves time and there's nothing better than buying time. Because when you're, when you, when you run out at the end of your life, you would give everything you own for more time.

• 1:18:25David Senra?

  Okay, so if you're interested in that and you want to support the podcast, go to blinkers.com/ founders. They give you 20% off and it's a great way to support the podcast and get you something that's actually useful and something you actually use. Last way you could support the podcast and then I will leave you for this podcast until we meet again is audibletrial.com/ founders. Audibletrial.com/ founders. You're familiar with Audible. If you don't have an Audible subscription, it's a no-brainer to me. So, Audible, here, let me just go to the actual URL real quick. So audibletrial/ founders, they give you a free audiobook just for, you sign in with

• 1:19:10David Senra?

  your Amazon account, you get 30 days free, you can cancel anytime you want, and you get to keep the book even if you cancel before your 30 days is up or after your 30 days is up for that matter. You get to keep your books. Audible, to me, is just like podcasts. I use podcasts and books mainly for learning and for keeping my mind healthy and interested. And there's just times when I'm driving or walking or doing other things where I'm not going to be able to stare at a screen or a book, and Audible's just a no-brainer. Now, what I would recommend? So let me just read the stuff you get in case you don't know. So you get 30 days membership free, plus a book to get you started. You get one month of credit after trial, so you get one book every month, good for any book regardless of price. It's how, I don't know if your social circles like this, but I feel like more of my friends

• 1:19:55David Senra?

  are listening to Audibles than they are even reading books now. I still prefer reading books first, but Audible supplements that to me, like I said, in the times where I can't read books. And I've kind of gotten away from reading books. I own a lot of Kindle versions as well as paperback or hardcover versions, so I'll buy multiple copies of the same book, because if I travel or something, I like to read it on my iPhone. But, I just, I fell in love with reading actual, physical books, and I love this, this technology's been around for 5,000 years.

• 1:20:24David Senra?

  And that's my first choice, but supplemental to that, I listen to at least one book a month, too.

• 1:20:32David Senra?

  And it's just like reading, it's just like listening to a really long podcast. I mean, that's basically what it is. So, the reason I said, remember, the last few weeks, I've been reading other books that are not biographies. This is why it's also taken me so long to get this episode out. So I just finished Nassim Taleb's newest book. It's called Skin in the Game: Hidden Asymmetries in Daily Life. I thought it was fantastic. It's book five in what he calls the inserto. And so what the inserto is, is his ideas on probability. And it starts with Full by Randomness, it's the first book, so each book is a standalone book, but it's also in a collection of this idea that he's been expounding on for now over 20 years. So it goes Full by Randomness, Black Swan, The Bed of Procrustes, Anti-Fragile, and now Skin in the Game.

• 1:21:14David Senra?

  I've read all of them. I recommend. So I got a text from a friend. Let me see if I can find it the other day. And he, so he is one of these guys that only reads like audible stuff.

• 1:21:28David Senra?

  Only, I guess, reads, listens, whatever you want to put, say there. But he texts me with, and I have to scroll back now, but it was funny, because I got this text when I woke up in the morning. Skin in the Game, and then the emoji for the thumbs up or thumbs down. And I was like, are you asking my opinion? Yes. And I respond, I recommend everyone read every single word in the inserto. So yes, read the fucking book. And he said, fucking wasn't necessary, but will do. And I was like, listen, I'm passionate for his writing. So, obviously, don't mean to just have gratuitous vulgarity there, but in a lot, in some cases, it's definitely deserved.

• 1:22:10David Senra?

  So, you get one credit a month after a trial. Good for any book, regardless of price. It's ad-free, premium auto, audio you can listen to offline, no interruptions, that's huge. Your own amazing library. Keep every book, even if you cancel. You also get 30% off of exclusive members, 30% discount for member-only savings if you want to buy more than one book a month. And one of the coolest features is easy exchanges. If you don't love the book, you swap it out for free anytime. So, support the podcast. Go to audibletrial.com/founders. You get one free book. Sign up with your Amazon account. It takes two seconds. And if you want to read one of the books I've covered in the past, I would recommend that. If you don't want to, I'd recommend Skin in the Game. Listen to it.

• 1:22:52David Senra?

  Unfortunately, Taleb doesn't narrate it, but it's still his writing. And it's worth your time. And it's not that long. I think this is, out of all his books, some of his books are monsters, like worth it. But I think, I got the hardcover version and it's sitting in front of me. It's 224, something like that. Yeah, 230, something like that. So audibletrial.com/founders, that will give you a free book and it's a great way to support this podcast. I've taken up enough of your time. Thank you for listening this long. I appreciate everything that you're doing. I appreciate this very unique experience, just going back to the Volko that I shared earlier,

• 1:23:33David Senra?

  that the internet has broadened, you know, the amount of things that we can do, career-wise or career or otherwise. The internet and the iPod, and now the Apple iPhone and the rest of these smart devices, you know, have made it possible for me to have basically a one-on-one conversation with people all over the world and a one-to-many. So I look at the metrics and I'm just like, I just cannot believe how many people in all kinds of countries, you know, Japan, just everywhere, listen to this. Because I think that there is a small percentage of us that are extremely passionate about building companies and couldn't imagine doing anything else.

• 1:24:18David Senra?

  And then there's other people that listen to this that aren't there yet and they want to be there. So, I don't know, this is just a really cool experience. And I always kick myself in the butt when I, like, sometimes I take too long to put on another podcast or I get distracted or whatever the case is. Now, keep in mind, sometimes I have to read books that I'm not, like, I read books and I'm like, there's no way I'm going to recommend this, so it takes a little while. Because, you know, I have these little mini failures in between. But what I'm saying is I'm really appreciative of this. I'm just in love with doing this. So, and I'd be just be talking to no one if you didn't listen. So I appreciate you. Have a great day. Talk to you soon.