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



In this episode, the hosts discuss "A Truck Full of Money" by Tracy Kidder, which chronicles the life of Paul English, co-founder of Kayak. The book delves into English's journey from a rebellious student who despised homework to a successful entrepreneur, all while battling bipolar disorder. It touches on his early interests in music and computers, his disdain for television, and his entrepreneurial ventures, including selling drugs in school. English's story is framed by his insistence on authenticity, requesting that Kidder not portray him more favorably than he is. The narrative also covers the sale of Kayak to Priceline for $1.8 billion, revealing the complexities of a man who achieved great success despite personal struggles, and how his condition influenced his professional life and relationships. The conversation underscores the human aspects of entrepreneurship, the challenges of mental health, and the importance of perseverance.

Summary Notes

Key Themes

Paul's Attitude Toward Authority and Homework

  • Paul's defiance against authority and homework is established early on.
  • Despite his resistance to homework, Paul is shown to be industrious and driven in areas of personal interest.
  • His interest in the school band and computer club demonstrates a selective commitment to activities that engage him.

"Fuck you. I will never do homework."

This quote exemplifies Paul's rebellious attitude towards the traditional educational expectations and his determination to follow his own path.

Paul's Early Entrepreneurial Spirit

  • Paul's entrepreneurial activities began in school, where he profitably sold marijuana.
  • His business acumen is evident from a young age, showcasing his ability to generate profit and manage a covert operation without getting caught.

"In 7th grade, his first year at Latin...He could have bought several used cars with his profit had he been old enough to get his driver's license."

The quote highlights Paul's early entrepreneurial success and his ability to accumulate significant wealth as a young student, indicating a natural aptitude for business.

Paul English's Career and Achievements

  • Paul English is most well-known as the co-founder of Kayak.
  • His career is marked by a series of entrepreneurial ventures, some successful and others not, but all contributing to his eventual success with Kayak.

"Most well known for being a co-founder of Kayak the travel search engine."

This quote identifies Paul English's primary claim to fame, establishing the context for discussing his professional journey and accomplishments.

Author's Note and Approach to Writing about Paul English

  • Tracy Kidder's author's note reveals her unique approach to writing about Paul English.
  • Paul insisted that the portrayal of him in the book be honest and not overly flattering, reflecting his desire for authenticity.

"You have to promise not to make me look better than I am, he said."

This quote from Paul English sets the tone for an honest and unvarnished depiction of his life and character in the book, emphasizing the importance of authenticity in biographical narratives.

The Impact of Bipolar Disorder on Paul's Life

  • Paul's struggle with bipolar disorder is a significant theme in the book.
  • Despite his mental health challenges, Paul achieved remarkable success, including the sale of Kayak to Priceline.

"Paul's diagnosed with bipolar disorder."

This quote highlights the personal challenges Paul faced alongside his professional achievements, providing a fuller picture of his life beyond his entrepreneurial success.

Kayak's Business Model and Success

  • Kayak's business model involved earning referral fees from travel-related searches conducted on its platform.
  • The company's profitability and efficiency were notably high, with significant revenue generated per employee.

"In 2012, Kayak's revenues came to nearly $1.5 million per employee, one of the highest ratios among all publicly traded companies."

This quote underscores the efficiency and success of Kayak's business model, illustrating how the company was able to generate substantial revenue with a relatively small team.

Paul's Management Style and Philosophy

  • Paul English preferred small, efficient meetings and was proactive in enforcing this preference within Kayak.
  • His management style emphasized the importance of productivity and avoiding unnecessary bureaucracy.

"I want meetings of three people, not ten."

This quote reflects Paul's belief in lean, focused meetings as a key to efficiency and effectiveness in a business setting.

The Origin of the Book's Title

  • The book's title, "A Truck Full of Money," refers to a prediction made by Paul's colleague about Paul's potential for financial success.
  • The title encapsulates the theme of unexpected and significant wealth that can come from entrepreneurial ventures.

"Someday this boy is going to get hit by a truck full of money, and I'm going to be standing beside him."

This quote reveals the origin of the book's title and foreshadows Paul English's eventual financial success, as well as the loyalty and camaraderie among his team.

Paul's Discomfort with Wealth and Success

  • Despite his success, Paul experiences discomfort with wealth and has a desire to give back.
  • His philanthropic efforts are driven by a sense of social responsibility and a personal struggle with the concept of wealth.

"He's very uncomfortable with being successful."

This quote captures Paul's internal conflict regarding his financial success and his inclination to share his wealth with others, reflecting a complex relationship with money.

Life Satisfaction and Personal Struggles

  • The transcript discusses the concept of life satisfaction and personal struggles, highlighting how external successes do not necessarily equate to internal happiness.
  • It points out the pressure people, especially entrepreneurs, face to maintain a facade of constant success and the detrimental effects this can have on mental health.
  • The conversation also touches on how professional life can become intertwined with personal identity, making it difficult to separate self-worth from professional achievements.

"It matters how you feel about yourself. And he was deeply, obviously deeply oppressed."

The quote emphasizes the importance of internal feelings of self-worth over external perceptions of success, as exemplified by the individual's deep sense of oppression despite outward achievements.

"So if you are struggling with any of this kind of stuff, I definitely read this book because there is a happy ending here."

This quote suggests that those facing similar struggles may find solace or solutions in reading the book being discussed, which apparently offers a positive outcome.

Mental Health: Bipolar Disorder and Hypomania

  • The transcript explores the topic of bipolar disorder, with a focus on the symptoms of hypomania and depression experienced by the individual.
  • It describes the cyclical nature of the illness, with alternating states of depression and mania, and how these states can impact one's professional and personal life.
  • The conversation highlights the importance of understanding symptoms and finding effective treatments, including the use of medication, to manage the condition.

"Hyperactivity was likely just a symptom of his deeper problems, his bipolar disorder."

This quote identifies hyperactivity as a potential symptom of a more profound mental health issue, specifically bipolar disorder, which includes a range of symptoms beyond just increased activity levels.

"He called his current psychiatrist and found a drug, an epileptic called lamectal, that had kept Paul's depression mostly at bay for a decade and with minimal side effects."

The quote indicates that the individual found an effective medication to manage depression, a component of bipolar disorder, highlighting the importance of psychiatric treatment in managing mental health conditions.

The Impact of Professional Life on Mental Health

  • The transcript discusses how professional achievements and pressures can trigger mental health episodes, using the example of a successful business sale leading to a depressive episode.
  • It illustrates how societal expectations and personal pressures can lead to a disconnect between public perception and private reality.
  • The narrative underscores the need for founders and entrepreneurs to find balance and support when dealing with the mental health implications of their professional lives.

"And in reality, he's at his lowest point."

This quote demonstrates the paradox that can occur when significant professional success leads to a decline in mental health, contrary to what external observers might expect.

"He was subject instead to the oddly, vaguely named hypomania, which means less than full-fledged mania."

The quote provides insight into the specific type of bipolar disorder the individual experiences, which is characterized by less intense manic episodes known as hypomania.

Medication and Side Effects

  • The transcript touches on the use of various medications to treat bipolar disorder and the side effects that can accompany them.
  • It highlights the individual's struggle with finding the right medication and dosage to manage symptoms without experiencing adverse effects.
  • The conversation also addresses the individual's use of alcohol as a coping mechanism, despite the potential risks and contraindications with medication.

"There's probably a dozen different medications throughout his life that he's on."

This quote reveals the extensive trial and error process of finding the right medication to manage bipolar disorder, implying the complexity of treating mental health conditions.

"What even, like, he talks about what, like five milligrams can do to him."

The quote underscores the sensitivity of individuals to medication dosages and the profound impact that even small changes can have on their well-being.

Highs of Hypomania and the Desire for Normalcy

  • The transcript delves into the experience of hypomanic highs, describing the physical sensations and psychological effects that accompany them.
  • It discusses the individual's ambivalence towards the highs, which can be both exhilarating and frightening, and the challenge of wanting to feel normal.
  • The narrative explores the concept of mania being so pleasurable that it can lead to a reluctance to continue medication that mitigates these highs.

"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."

This quote captures the individual's appreciation for the productive and euphoric aspects of hypomanic episodes, despite their potential risks.

"It's a funny thing about mania. It feels so good that when it is with us, we feel cured, perfect, and we don't want the meds anymore."

The quote articulates the deceptive nature of mania, where the positive feelings can lead to a false sense of being cured, resulting in a desire to discontinue medication.

Professional Transitions and Identity

  • The transcript discusses the transition from being a business owner to an employee and the identity crisis that can ensue.
  • It illustrates how the change in role can lead to a lack of motivation and a sense of loss of purpose, especially for someone who has been deeply invested in their company.
  • The conversation also touches on the realization that one's passion and drive may not align with the new role, leading to a reevaluation of professional goals.

"As of tomorrow morning, when I wake up, I'm now an employee."

This quote signifies a pivotal moment in the individual's professional life, marking the transition from business owner to employee and the psychological impact of that change.

"He's not meant to be an employee."

The quote suggests that the individual's identity and sense of self are closely tied to being a leader and innovator, rather than fitting into the role of an employee within a larger organization.

The Economics of Video Games and Entrepreneurship

  • The transcript highlights the economic potential of the video game industry, using the example of an individual's brother who becomes a successful game programmer.
  • It discusses the brother's decision to leave a lucrative offer from a large company to start his own business, emphasizing the financial and creative advantages of entrepreneurship.
  • The narrative also touches on the importance of ownership and control over one's work, contrasting it with the limitations of working for another entity.

"They're selling 4 million copies, $20 a pop, right? And that's my math is 80 million on that. Okay, so $80 million and they offer Ed, the guy that created what they sold for $80,050,000."

This quote illustrates the stark disparity between the revenue generated by a successful video game and the compensation offered to its creator, highlighting the financial benefits of entrepreneurship over traditional employment.

"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."

The quote exemplifies the success and rewards that can come from taking the risk to start one's own business, as opposed to remaining an employee.

The Attraction to Programming

  • The transcript explores why the individual was drawn to programming, describing it as a world where he had control and could find refuge from the chaos of family life.
  • It discusses the satisfaction derived from creating something that functions according to one's own design, without the unpredictability of human interactions.
  • The conversation also reflects on the balance between the precision and imperfection inherent in programming, and how it appeals to those who value "good enough" over perfection.

"But he could always figure out how to tell the computer to do what he wanted, and it didn't argue back or ignore him."

This quote highlights the appeal of programming as a domain where one's instructions are followed precisely, providing a sense of control and accomplishment.

"It was the creation of something notional, fictional, imaginary, that nonetheless had tangible effects."

The quote captures the essence of programming as a creative process that, while abstract, results in real-world applications and impacts.

Negotiation Skills and Influence of Family

  • The transcript provides insight into how the individual learned negotiation skills from observing his father's tactics at yard sales.
  • It describes the father's use of humor and lowball offers to disorient sellers and secure a better deal, skills that the individual later applies in his own professional negotiations.
  • The narrative suggests that family experiences and observations can significantly influence one's approach to business and interpersonal interactions.

"I'll give you $3 for this piece of junk."

This quote exemplifies the father's bold negotiation strategy, which often led to successful outcomes despite the initial low offer.

"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."

The quote indicates the individual's keen observation of his father's negotiation style, which combined humor with aggressive bargaining, and how these observations shaped his own negotiation tactics.

Tom's Background and Experience at Harvard

  • Tom grew up in Boston and attended Harvard in the 1930s.
  • He came from a blue-collar background and felt inferior to his more privileged classmates.
  • There was a sense of class division at Harvard during that time.
  • Tom later encounters a Harvard classmate, Forbes, who acknowledges societal changes in their perception of "you people."
  • Tom found success in construction and believed in the meritocracy of being the low bidder.
  • He also saw technology as a route for those with "psychological oddities" to rise, regardless of background.

"He felt that even if he was as smart as some of the people there, because he didn't have their upbringing, they were somewhat inferior."

This quote highlights Tom's sense of inferiority due to his blue-collar background compared to his Harvard peers.

"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 acknowledges the exclusionary practices of the elite but also recognizes that there were pathways to success for those from different backgrounds, like himself.

The Democratizing Force of Digital Technologies

  • Tom references Donald Knuth's theory that only about 2% of humans are naturally inclined to program computers.
  • Digital technologies are seen as a democratizing and equalizing force, providing opportunities regardless of one's background.
  • Naval Ravikant's tweet about the Internet broadening career possibilities is discussed, emphasizing the shift from traditional career paths to more diverse opportunities enabled by technology.
  • The speakers reflect on the absurdity of being proud of one's inherited status rather than one's achievements.

"You could have the wrong accent and no table manners and be possessed by psychological oddities or worse, so long as you belonged amongst Newth's 2%."

Tom believes that in the realm of technology, traditional barriers to success are less relevant if one has the aptitude for programming.

"The Internet has massively broadened the possible space of careers. Most people haven't figured this out yet."

This quote from Naval Ravikant is used to illustrate the transformational potential of the Internet in creating new career opportunities.

Paul's Diagnosis and Career at Interleaf

  • Paul struggles with interpersonal interactions at Interleaf, feeling misunderstood and occasionally letting his anger show.
  • After months of intense coding, Paul seeks medical help and is diagnosed with bipolar disorder.
  • He is prescribed lithium, which he reluctantly takes, fearing the loss of his energy and drive.
  • Despite his diagnosis, Paul leaves a stable job and a million dollars in options at Interleaf for a startup venture, driven by his belief in the potential of the Internet.

"Do I have to explain every fucking step here?"

Paul's frustration during meetings at Interleaf is evident in this quote, reflecting his struggles with communication and the onset of his bipolar disorder.

"He's married. He asked his wife to take him to the nearest big hospital. He didn't dare drive himself."

This quote indicates the seriousness of Paul's condition and his decision to seek medical help, leading to his bipolar disorder diagnosis.

Boston Light Software and Negotiation Skills

  • Paul starts his own company, Boston Light Software, after leaving Netcentric.
  • He uses negotiation skills learned from his father to sell Boston Light Software to Intuit for $33.5 million.
  • The sale of Boston Light is a testament to Paul's entrepreneurial spirit and ability to leverage his skills and experiences to achieve success.

"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."

This exchange between Paul and his father highlights Paul's successful application of his father's negotiation techniques in a high-stakes business deal.

Reflections on Entrepreneurship and the New Economy

  • The speakers discuss the role of luck in entrepreneurship, referencing Paul's fortunate change of flight on September 11, 2001.
  • Paul's property has a history connected to the ice trade, inspiring him to think about the potential for seemingly "wacky" ideas.
  • The narrative emphasizes the American ethos of continual reinvention and the pursuit of new ideas, which Paul embodies.
  • The podcast concludes with reflections on the value of reading books and supporting the podcast through book purchases.

"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."

This quote encapsulates Paul's entrepreneurial mindset, characterized by a disregard for the past and a focus on invention and progress.

"I sold my company, dad. His father smiled. But when Paul told him the price. 33 and a half million dollars. Dad? The old man's smile vanished."

The shock and disbelief expressed by Paul's father upon learning of the sale price of Boston Light Software illustrates the magnitude of Paul's accomplishment.

Value of Books and Reading

  • Books offer extensive hours of entertainment and valuable information at a low cost.
  • The book "Titan" on John D. Rockefeller provides insights that can be applied to personal and professional life.
  • Recognizing the importance of not persisting in flawed situations.

"To the rules, that book titan on John D. Rockefeller that I covered, which is probably 700, 800 pages, but it's like a 25 hours read, and I think you can get it for like $14, something like that."

This quote highlights the value proposition of reading a comprehensive book like "Titan" and the extensive content it offers for a reasonable price.

"And it's the author describing John D. Rockefeller. And he's like, he was not one to persist in a flawed situation."

The quote reflects on a key takeaway from the book, emphasizing the importance of recognizing and not continuing with ineffective strategies or situations.

Supporting the Podcast

  • Utilizing Amazon links to purchase books helps support the podcast.
  • Engaging on social media platforms like Twitter can influence book choices for future episodes.
  • Recommending the podcast to others and sharing links contributes to its growth.
  • Leaving positive reviews, especially on platforms like Apple Podcasts, supports the podcast without financial contribution.

"Using the Amazon links 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."

This quote explains how using provided Amazon links to purchase books can financially support the podcast.

"I also read them. I tried to avoid Internet comments, but I do think that they're funny and there's some good."

The speaker acknowledges reading and valuing reviews, highlighting their importance for feedback and support.

Podcast Apps and User Experience

  • Discusses various podcast apps like Overcast and Breaker, highlighting their unique features.
  • Overcast is praised for its design, while Breaker offers features like listening history and note-taking.
  • Social features on apps can be controversial, but they can also help curate personal learning experiences.

"Parts of overcast I think is the single best podcast app built. And I like that it's just one dude doing it."

This quote expresses admiration for the Overcast app and its developer, emphasizing the quality of its design.

"Breaker has interesting features."

The speaker briefly acknowledges Breaker's features, which contribute to its utility as a podcast app.

Efficiency and Minimalism

  • Discusses the concept of essentialism and the disciplined pursuit of less.
  • Emphasizes the importance of focusing on vital goals and well-being while discarding the unimportant.
  • Shares personal application of essentialism in life choices and the desire to focus on passions and eliminate distractions.

"So what essentialism is? The subtitle is the disciplined pursuit of less."

This quote introduces the concept of essentialism, which is about focusing on fewer, more important tasks.

"If it isn't a clear yes, it's a clear no."

The speaker highlights a key principle of essentialism, which is to be decisive and eliminate ambiguity in decision-making.

Blinkist and Book Summaries

  • Blinkist offers concise summaries of nonfiction books, saving time for readers.
  • It can be used to discover new books or to decide if a full read is necessary.
  • The app provides a way to efficiently consume information in the information age.

"Blinkus. And I think now they do monthly. But when I bought the app, when I first knew about it, I did the yearly, and I think their feature request was like, hey, let's do this monthly."

This quote discusses the Blinkist app's subscription model and the options available to users.

"Essentialism, which is the main idea in the book, focuses on four main points."

The speaker summarizes the core principles of the book "Essentialism," providing a concise overview of its content.

Audible and Audio Books

  • Audible offers a convenient way to consume books, especially when physical reading is not possible.
  • Recommends Audible for its vast library and the ability to keep books even after canceling a subscription.
  • Suggests using Audible to explore new books or listen to recommended titles from the podcast.

"Audible to me is just like podcasts. Like, I use podcasts and books mainly for learning and for keeping my mind healthy and interested."

This quote compares Audible to podcasts, emphasizing their role in learning and mental engagement.

"So support the podcast. Go to audibletrial.com founders. You get one free book. Sign up with your Amazon account."

The speaker provides a call to action for listeners to support the podcast by signing up for Audible, offering a free book as an incentive.

Gratitude and Audience Engagement

  • Expresses appreciation for the audience and the unique experience of connecting with people globally through the podcast.
  • Reflects on the joy of creating the podcast and the importance of audience support.
  • Encourages continued engagement and feedback from listeners.

"I appreciate everything that you're doing. I appreciate this very unique experience."

This quote conveys the speaker's gratitude towards the audience and the opportunity to connect with them.

"So I appreciate you. Have a great day. Talk to you soon. Bye."

The closing statement expresses thanks and well-wishes to the listeners, fostering a positive relationship with the audience.

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