Michael Moritz - Lessons From 40 Years of Investing and Writing - [Invest Like the Best, EP.491]

Michael Moritz led Sequoia Capital for nearly two decades and backed some of the defining companies of the internet era. In his new memoir, Ausländer, he turns his attention to his own family, Jewish refugees who fled Nazi Germany and rebuilt their lives in Wales. We discuss the imprint his parents left on him, the method he used for decades of asking founders about their childhoods and the Time profile that ended his relationship with Steve Jobs. We also also cover Lee Iacocca, why Don Valentine hired him, Alex Ferguson's approach to managing players, Elon Musk, and why Mike still struggles to feel proud of anything he has done. Please enjoy my conversation with Michael Moritz. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp’s⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠. ----- WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant. Timestamps: (00:00:00) Welcome to Invest Like The Best (00:02:16) Where Does One Person End? (00:11:15) The State of the World Today (00:15:08) The Unlived Life of Parents (00:17:33) Lee Iacocca, Eternal Outsider (00:21:03) His Most Revealing Question (00:26:03) Resisters, the Silent, and Collabos (00:33:30) The Profile of Steve Jobs (00:38:04) Frank Auerbach's Total Obsession (00:41:04) Why Don Valentine Hired Michael (00:46:44) Building Sequoia (00:49:49) What Michael Learned from Alex Ferguson (00:52:57) The Great Man Theory (01:00:36) Defining Extraordinary Writing (01:03:40) Stepping Back From Sequoia (01:06:54) A Philosophy of Parenting (01:09:00) The Next Book: Iran (01:11:44) The Kindest Thing

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

• 0:01Patrick O'Shaughnessy?

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• 0:42Patrick O'Shaughnessy?

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• 1:30Patrick O'Shaughnessy?

  Hello and welcome, everyone. I'm Patrick O'Neal, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus, along with all of our podcasts, at colossus.com.

• 1:54Speaker 01

  Patrick O'Neal is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.

• 2:22Patrick O'Shaughnessy?

  When I was reading your book, one of the lines or the ideas that has really stuck with me ever since is where does one person end and the next person begin? And this deep dive that you took into the impact of one's history, family history, heritage, on who a person is. I'm interested in this from so many angles. As a parent, as a person interested in history, as a person interested in genetics, nature versus nurture. If I were to sum up the book in that question, what is your answer to that? What did you come away thinking after this deep study of your own family's history?

• 2:58Speaker 02

  One of the things that came out of the book, which I didn't really expect, was discovering who I am and why I became whatever it is that I've become. And that was an unexpected gift of the writing. And it came from this exploration of my family's past, in particular, my parents. Going back and excavating the deep memories of childhood, the sort of atmosphere in our home and in the general milieu in which I grew up, helped me understand a lot about why I am who I am and react to certain things in the fashion

• 3:42Speaker 02

  that I do. Because unwittingly, obviously, every parent leaves an imprint on a child. That's obviously especially true during the formative years. Whatever the formative years are, I'm no sort of child specialist or scientist, but before you turn 12, 13, 14 years old, those imprints that you've absorbed in some manner, consciously or unconsciously, those remain with you. And both the angels and demons, I think, that you deal with for the rest of your life.

• 4:19Patrick O'Shaughnessy?

  What were yours? I'm so curious that you're performing on yourself the exercise that you're famous for doing with others that you invested in or hired, focusing on these first 14 years. What new understanding of yourself came out of this exercise?

• 4:34Speaker 02

  I grew up in this family of refugees from Nazi Germany in Wales. Refugees, by definition, are a minority. Jewish refugees in Wales during the 1960s and 1970s were a further minority. People look at me today and they think, oh, here's this old white man. He's not a minority. And I can understand that, but it's how an individual feels rather than how other people might look at you. It touched me in a variety of ways. My parents, they were never in the camps. They got out of Germany in the 1930s. And they were loath to use the word survivor, because they always felt the word survivor denoted somebody who

• 5:19Speaker 02

  actually had survived the camps. But they were refugees and, in their own way, had survived. That motive to survive, no matter what the odds were, even though the odds that I faced growing up weren't like my parents, I think the need to survive. When you think about surviving, you're thinking about, to some extent, living by your wits, being very suspicious of the motives of others, wondering where and how bad things will occur and happen and guard against them. I think it gave me, in retrospect, I didn't understand it at

• 6:01Speaker 02

  the time, the sort of drive and grit that I wouldn't have had without that particular atmospheric backdrop.

• 6:09Patrick O'Shaughnessy?

  When you study it and you think about your own childhood, how did that transfer from your parents to you? Was it the stories they told?

• 6:16Speaker 02

  It was definitely not the stories they told, because they didn't tell the stories. I didn't really get to know the stories until I sat down and began work on this book. What I did know was the general arc of history, obviously, this miserable, ferocious, catastrophic whirlwind in which they and millions of others were caught up. But they didn't talk about the past in the real detail that I, much later, when I was thinking about the book, became interested in. It was just broad sweeps. I think it was much more the daily behavior, the reaction to events, the reaction to things, the sense that doom was not very

• 6:59Speaker 02

  far away. The fact that if horrors had occurred in the past, there was a real need to be vigilant and wary about navigating daily life.

• 7:12Patrick O'Shaughnessy?

  There was a couple of stories in the book, one in particular where you talk about two separate people, one who decided to stay in Germany and one who decided to leave. Quite a poignant and interesting on this topic of survivor outsider, early instinct, when things are changing, to take notice and not double down and stick around. Maybe tell that story and explain what you learned.

• 7:32Speaker 02

  The two individuals, Patrick, that you refer to were my grandfathers, my maternal grandfather and my paternal grandfather. I'll start with my paternal grandfather, who was a civil servant. He was a sort of lower-level judge in the judiciary in Bavaria, a province in southern Germany. He had fought in World War I. He had somehow or other survived the horror of Verdun. He'd been given his Iron Cross. And he was, I think, a great believer in the German state, in the security that the state offered. And then, much later,

• 8:15Speaker 02

  in 1933, he lost his job. This is my assessment of the situation, because he was a civil servant. He was by nature conservative, by nature somewhat cautious, but also had this great belief in the state and the endurance of the state and the durability of the state, and that eventually the storm would blow over. He also had a pension, and the pension was very important to him as a means for survival. It was a combination of all of those things. He wasn't oblivious, obviously, to what was happening around him, but it did make him more reluctant to leave Germany, I think, until it was too late. And people

• 8:59Speaker 02

  forget, even if somebody had decided to leave Germany, there are all sorts of obstacles in the way. You had to find a place elsewhere that would accept you. You had to pay big taxes to the Nazi government in order to be able to secure your exit visa. So there are all these sorts of obstacles. So that was my paternal grandfather. And he and his wife eventually were shipped off east and disappeared from history. My maternal grandfather was cut from a different cloth. I was too callow as a youth to really understand this, but he died when I was about 16. He had been a cattle trader, which was one of the occupations that Jews were really permitted to do in Germany. But he was almost blind

• 9:44Speaker 02

  as a young man and completely blind by the time that I met him. But somehow or other had been able to carve out a comfortable living for himself and his family by trading in cattle in a rural village in northwestern Germany. My assessment of him, in retrospect, was that he was more streetwise. He was more entrepreneurial, wasn't burdened by the need to remain and collect a state pension, because he had always been able to sustain himself and look out for his future. And he got out with his wife, my grandmother. But they got

• 10:22Speaker 02

  out by the skin of their teeth. They got out 72 hours before war broke out. 72 hours later, they too would have perished.

• 10:32Patrick O'Shaughnessy?

  What do you take from that? What is the big lesson from that instinct? How does that instinct imprint it on you and on the people you backed throughout your life and career, written about?

• 10:43Speaker 02

  I'm not sure that it's all that relevant to the people I've encountered in this journey through life, but it certainly has had consequences for me, particularly in times like the ones that we are living through at the moment and the atmosphere that is prevalent, to some extent, in the US and also in Western Europe. I think the necessity for always feeling that you have a bolt hole, that you have someplace to go if the fire gets too hot. That's the lesson that I took away from my family history. Libby's saying that you can never have enough passports.

• 11:20Patrick O'Shaughnessy?

  Do you feel that especially true now? Say a bit about the state of the world, how you perceive the state of the world.

• 11:26Speaker 02

  It's an uncomfortable place for minorities. The United States and Western Europe writ large. It doesn't matter whether you're Asian or Muslim or black or Jewish. I understand the reasons and I want to be careful as well. I am not whining about antisemitism. I'm not complaining about it. I long ago came to terms with the fact that it's just a fact of life. It's been around for 2,500 years. It's not going to disappear in 2026 or 2030. It's always going to be with us. And in fact, as we were talking about a few minutes ago, I think the fact that antisemitism

• 12:07Speaker 02

  was around and has been around and it's been something I've been conscious of all my life or all my sentient life, it's made me stronger. But I think it's disquieting if you're living in a society where in America, I think my simplistic way of thinking about who feels safe is the contingent of Americans who feel safe are white Christians who own guns. Everybody else feels a degree of insecurity, whether you're pursued by ICE or you go to a house of prayer that has to be guarded by police to ensure that that's safe. And that exists in America.

• 12:48Speaker 02

  It exists in the United Kingdom, in France, in other countries around Europe where far-right governments have come to the fore. And obviously, everybody has read about the recent elections in Germany of a far-right party in Saxony Province. And I think in times of economic distress, where you have millions of people who've been tens of millions of people who feel they've been left behind, that feeling of despair can easily be whipped up into a horrendous stew by leaders with authoritarian impulses.

• 13:28Patrick O'Shaughnessy?

  I forced you to put on your optimistic or hopeful hat and thinking about the future as it relates to this problem.

• 13:35Speaker 02

  Well, Viktor Orban was booted from office. He was riding high a couple of years ago. In some places, there clearly are pushes to the center, which would be, I think, very consoling for people and a return to some modicum of civility in the various societies in which, you know, people like us travel. So here in America, clearly the midterms, the next 18 months after that are really going to shape how we're going to live in the next decade because there's been the imprint of one person on the last decade in America. I think in Britain, the person who's identified with the far-right Nigel Farage may well have had his best day and his best day may well be behind him.

• 14:18Speaker 02

  I think it's different in France with Marie Le Pen and the elections next year. It's different in Spain and it's potentially different in Germany.

• 14:27Patrick O'Shaughnessy?

  Do you think that the internet fundamentally changes the potential for civility and political moderation because it so rewards extremes and attention?

• 14:38Speaker 02

  I think the three-letter answer is yes. I think it's been true of every form of new media from the beginning of the printing press. But obviously, the internet and mobile telephony has made it far easier to spread false memes and innuendo. But it's a much larger, more amplified version of what occurred in Germany when radio took off during the 1930s and where the radio waves were dominated by extreme propaganda and racist views and loud lies told frequently.

• 15:15Patrick O'Shaughnessy?

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• 15:56Patrick O'Shaughnessy?

  Firms are moving off legacy technology and onto RidgeLine because of how far ahead RidgeLine's AI features are compared to anything else in investment management software. I've been hearing from a lot of investment managers about AI and they fall roughly into two camps, with some unsure where to even start and others convinced that they can build their own order management system over a weekend. The reality is that running an investment firm will always require governance, controls and a single source of truth for your data. And no amount of AI enthusiasm changes that requirement. RidgeLine is built on exactly that foundation, which is why I believe that the firms that come out ahead in the AI era will be the ones running on RidgeLine's unified platform. If you're serious about your firm's AI strategy, RidgeLine should be part of that conversation

• 16:39Patrick O'Shaughnessy?

  and you can request a demo at ridgeline.ai. Going back to your family's history, one of my favorite topics is this idea that you can learn so much about a person from what happens in their first 12, 13, 14 years, as you said. Carl Jung had this great idea of studying the unlived life of the parent. Another way of framing it would be, this is a little trite, but you should be like who your father was supposed to be. You should live the life that he was unable to or didn't quite. And that part of that imprinting is children observing their parents, what they're not going after, the risks they're not taking. And maybe running in that direction is a great way to explore. Back to the point about where does one person end and the next begin, like the break from

• 17:23Patrick O'Shaughnessy?

  the parents is really important. I'm curious how you arrived at this method of yours, this first 14-year interrogation method. When you first did it, how you do it, like what the method is and why you find it just so impactful in understanding a new person?

• 17:39Speaker 02

  I suppose I first came across it oddly in Detroit when I was a correspondent for Time Magazine with a colleague. I wrote a book about the Chrysler Corporation, but more importantly, the person who turned around Chrysler at the end of the 1970s and the beginning of the 1980s. And a man who was, for a time, the best-known business figure in America, even though today most people struggle to pronounce his last name, but he was a gentleman called Lee Iacocca. He was the son of Italian immigrants. In writing this book, we spent a fair amount of time interviewing Iacocca.

• 18:18Speaker 02

  And what came through loud and clear was how much as the son of Italian immigrants who'd grown up in Pennsylvania, Lee grew up in Pennsylvania, he felt like an outsider. He worked in the automobile industry and obviously in the upper echelons of the automobile industry where I think he was always viewed with suspicion, most notably when he worked at the Ford Motor Company by Henry Ford II and the other people who, obviously, everybody had immigrated, but who were much more members of the establishment. And Iacocca never felt like a member of the establishment and became very clear that all of that stemmed from his childhood.

• 19:02Speaker 02

  As the years went by, he began to interpret many of the slights that then fell upon him, including not getting the top job at Ford, to the fact that you were seen as an Italian immigrant.

• 19:16Patrick O'Shaughnessy?

  If you think about the people who have harnessed that outsider energy, a lot of whom you've backed with great success, have you seen people graduate out of it? And when they do, does their drive and motivation go away or suffer?

• 19:30Speaker 02

  I want to answer the previous question a little bit as well. You asked when I've met various people and various founders over the years, spent so much time on their backgrounds. Many of these people are only 20 years old or 21 years old.

• 19:43Patrick O'Shaughnessy?

  You're covering a big percentage.

• 19:44Speaker 02

  You're not exactly going to be able to ask them about their life in their 50s. So it's just natural to try to understand that. I don't think people grow out of it. I think what happens is that people work with a certain intensity in their late teens and their 20s and maybe their early 30s. And that intensity, for a whole variety of reasons, diminishes over time. I think that's what changes. The inner being doesn't change, the outward intensity changes.

• 20:14Patrick O'Shaughnessy?

  When you were asking these questions, was there any one thing or set of things that you tended to be looking for? Was it you coming away feeling as though someone had extreme drive?

• 20:24Speaker 02

  I try to paint when I have some time. I'm not a good painter, but I really enjoy it, at least the way that I paint. You make marks in different parts of the canvas and the marks seem unrelated. Maybe it's a color blue here and a color brown there. You're putting these marks and dots on the canvas. There doesn't seem to be any composition there whatsoever. And then eventually, in my case, the picture comes out and it's bad, but there's a picture at the end of it. And it's the accumulation of all these different marks. And I think that's what happens when you're talking to people about their backgrounds. You're looking for these little dots here and then eventually you put together this portrait for yourself of the individual.

• 21:09Patrick O'Shaughnessy?

  In searching for those dots, did you come to favorite questions that you always found yourself asking?

• 21:15Speaker 02

  There's one that comes to mind, which I've always found quite revealing, is to ask somebody if they think back and had a chance to do one thing differently, one action differently. What is it that they would do? And I remember one person we interviewed for Sequoium, who burst into tears when I asked that question. It turned out that he'd grown up as the son of an immigrant here in America. He was Hispanic. His father was very proud to have made it here and that his child was bright, his son was bright, and he was getting good marks at school. And this fellow, probably when he was 12 or so,

• 22:00Speaker 02

  had gone down to a corner grocery store with a pal of his and stolen some candy. The shopkeeper, who knew his father, complained to his father. And his father took him by the ear, took him back down to the candy store, made him apologize, made him empty his pockets. The man I interviewed was so chastened, so embarrassed by bringing shame upon his family, and his father just burst into tears.

• 22:26Patrick O'Shaughnessy?

  What's your answer to the question? What would you have done differently?

• 22:29Speaker 02

  You're a good interviewer. People don't listen to answers very often when they interview people. I think every child of parents feels this in one way or another. I felt it as I was writing the book, that I was embarrassed. And if I could erase one thing, it would be the some of my interactions and dealings with my parents, which I feel ashamed about today, but there's no going back. And I spent the first 16, 17 years of my life with them. But there were many things probably that I wished. And also, when I was a younger man, I just encounters with them that I wished had gone differently because I didn't really understand who they were. And so be it.

• 23:14Patrick O'Shaughnessy?

  Do you think that was mostly a natural drive to create your own independence? Like every child goes through with their parents?

• 23:20Speaker 02

  Yeah, I'm sure that was some of it. Arrogance was probably another part, a fail of comprehension of what they themselves had experienced, what had made them who they were, which I didn't understand.

• 23:35Patrick O'Shaughnessy?

  There's this notion of very small deeds in the book. I think the character's name was Anna.

• 23:39Speaker 02

  Yes.

• 23:39Patrick O'Shaughnessy?

  Can you talk about what you learned about the impact of small deeds?

• 23:43Speaker 02

  It was more than small deeds. So this lady that you referred to, whom I knew as a child. Her first name was Anna. When my father and uncle were growing up in Munich in the 1920s and the early 1930s, every sort of middle class, lower middle class household had a family servant. These were the days before washing machines and vacuum cleaners and all the rest of it. Those individuals in these households, when children were born, invariably became nannies as well. For my father and my uncle, this lady Anna, who was that person in my grandfather's house, she became a surrogate. She was a nanny.

• 24:28Speaker 02

  She was Roman Catholic. Eventually left the employment of my grandparents. She married a railway worker in Bavaria, who was also a Roman Catholic. They built their own house with their own hands. She and her husband never forgot the Moritz family. They, in the 1930s, opened their house to my grandparents and my uncle and father at a time when it became very unpopular to have Jews come stay in rural Bavaria for their holidays. But they did it for as long as possible. They didn't have children, these two. They were horrified by the Nazis.

• 25:13Speaker 02

  They did everything possible to help my grandparents and my father and uncle. And then after the war, because the feelings were so intense between my father and my uncle and this lady Anna, they went back to Bavaria very soon after the end of the war, developed this very strong connection with her until she eventually died. And I remember going and staying in her house. And the story of this house features in the book as well. As a young boy, surrounded by the specters of the Nazi past. But this lady was, I think, what they say at Yad Vashem

• 25:54Speaker 02

  when they, the Stoic acknowledgements on all the people who helped Jews and others during World War II. She was one of the righteous and had this ethical compass that she wouldn't allow anyone else to alter.

• 26:09Patrick O'Shaughnessy?

  What did you learn from these categories of people? I think you called them the resistors, the silent, and the collabos.

• 26:14Speaker 02

  This is a spectacular series that came out maybe 12 years ago, shot in France, maybe as a six series tale about life in a French village during World War II. And how some people resisted the occupation for as long as possible. Most people remained silent and some became active collaborators with the Nazis. And during COVID, when we were all on these long Zoom calls with lots of little pictures of 10 other participants that were in the Zoom room, I always used to look at each individual whom I knew on the whole.

• 26:58Speaker 02

  And I kept asking myself, well, if these people had been living in the French village in the 1940s, who would have stayed silent? Who would have resisted? And who would have been collabos? So I was judging people whom I know and whom I work with. And it was an interesting exercise. I didn't tell anybody else about it at the time, obviously. But I knew everybody on these calls well enough to know who had the sort of backbone that this lady that we were just talking about had. And they were always in the minority.

• 27:32Patrick O'Shaughnessy?

  How rare is it? Is it 1% of resistors out of 100 people? How rare do you think that expression is?

• 27:38Speaker 02

  I think it's very rare because bad things happen in countries when most people stay silent. Very few actively resist.

• 27:49Patrick O'Shaughnessy?

  Do you think that most of the people that you've backed in your career would be resistors?

• 27:54Speaker 02

  I'd have to think about that. I'd like to think so, but I'm not sure.

• 27:58Patrick O'Shaughnessy?

  Can you talk about the role that Bill Deeds played in your life? I'm always interested in these early moments of activation. And I'm curious when you first felt in life, whether it was with him or at some other time, when you first felt you were really good at something?

• 28:13Speaker 02

  I've never felt I'm really good at something. That's not false modesty on my part, to this day.

• 28:18Patrick O'Shaughnessy?

  How can that be in face of the evidence?

• 28:21Speaker 02

  Well, I think everybody is plagued by doubts, maybe competitiveness. It's a failing on my part. I have a very difficult time celebrating good things and celebrating success.

• 28:33Patrick O'Shaughnessy?

  Given that you're self-aware about it, have you ever tried to reverse that?

• 28:37Speaker 02

  I think it's heritage. I think it's the fact that my mother always felt that disaster was always around the corner. Doom was always around the corner. She died a few weeks before COVID. My mother was the predictor of doom. I remember as a kid growing up, she would have listened to the radio and inevitably the talk when we're having breakfast would be about some natural disaster that had occurred or a plane crash or something dreadful around the world. She died a few weeks before COVID. I felt sorry for her in a way that she missed COVID because this was the disaster that she'd been predicting or one of the natural disasters that she'd been predicting all her life. She was cheated out of COVID.

• 29:21Speaker 02

  But I think it's that sort of sense of being one step away from the precipice.

• 29:26Patrick O'Shaughnessy?

  Have you ever, though, been proud of a piece of work that you've done or created or felt that pride, like the emotion of it?

• 29:35Speaker 02

  I think I've always felt everything is unfinished and could be improved. And none of it's ever been perfect.

• 29:43Patrick O'Shaughnessy?

  So never a satisfied moment?

• 29:45Speaker 02

  Sometimes when I paint and compare a painting to what I might have been able to paint 10 years ago or 15 years ago. So I see a road to improvement, but then you go to MoMA or the Met.

• 30:01Patrick O'Shaughnessy?

  You're diminished.

• 30:02Speaker 02

  And you're reduced to being an insignificant speck.

• 30:05Patrick O'Shaughnessy?

  What about feeling a pride for someone else, not so much for yourself? You've backed some of the most extraordinary people in business history, for sure. You've written about some of the most extraordinary leaders, Alex Ferguson, others. Have you felt proud of them?

• 30:19Speaker 02

  No, not necessarily. The relationship is different. And so those have been voyages of curiosity, where they're the people who should feel proud of their accomplishments, not me as a bystander.

• 30:34Patrick O'Shaughnessy?

  I'm so curious about, for someone that's been involved in so many fascinating things, unlikely things, what jumps out as the highest energy moments? What were the things along the whole journey that gave you the most energy? I know you're a deeply curious person, so maybe it's something there.

• 30:50Speaker 02

  I think it's family, children, all the moments associated with. Harriet, my wife and I, we have two sons and they're now in their 30s. And one of them's got a couple of grandkids. I think it's deeply personal stuff.

• 31:04Patrick O'Shaughnessy?

  Back to Bill Deeds, I lost my train of thought there for a minute. I'm curious, the impact that he had on you? And I'm always interested in early impact that people have on others.

• 31:13Speaker 02

  I grew up, as you know, in Britain. And when I left college, I really wanted to be a journalist. My goal was to work on one of the big, at that point, what were called the Fleet Street newspapers. This is a long time ago, it's 50 years ago, that everybody read. And there were papers for different sections of the population. And I wanted to work on one of the big, really well-regarded newspapers. But there were trade union rules because the unions had a big clampdown on the way in which they held the operators of these newspapers in a straitjacket. And one of the consequences was the newspaper editors, they weren't allowed to hire college graduates

• 31:56Speaker 02

  directly from college because the fear of the unions was that it would impede their ability, interfere with their ability to hire 16-year-olds straight out of high school. The result was that if I'd wanted to go and work on The Times or The Financial Times, Daily Telegraph, one of those papers, I would have had to go and spend two or three years working on a small provincial newspaper. And I just didn't really want to do it. I was impatient, I was ambitious and all that sort of stuff. And I met this fellow, Bill Deeds, who was the editor of The Daily Telegraph and was a revered figure in British journalism and had actually, in an earlier life, been the

• 32:36Speaker 02

  figure on which Evelyn Waugh had modeled one of the characters in his famous satirical novel called Scoop. Bill Deeds very kindly responded to a letter that I'd written to him, applying for a job at The Daily Telegraph. He gave me half an hour in his office in Fleet Street. And I remember it, it was in the winter, it was raining, and I asked him for advice. And he told me that what he had wished he had done as a young man was go to America. And he encouraged me to move to America. I think that really helped propel me in this direction.

• 33:12Patrick O'Shaughnessy?

  So when you arrived here, what was the first big break or big move that you made that kicked off this?

• 33:20Speaker 02

  Well, I got very lucky. I got hired by Time, straight out of school, without any work experience. They were very willing to take a risk on a 22-year-old or 23-year-old without any real prior experience. And that was my first big break.

• 33:36Patrick O'Shaughnessy?

  The episode with jobs and time was so fascinating in your history, and I'm sure frustrating for you. What happened and what did you learn through that episode?

• 33:45Speaker 02

  It's a painful part of the past. This is three years after I joined Time. I'd taken a leave of absence. By then I was working in San Francisco in the bureau there and had taken a leave of absence to write a book about Apple and for a variety of reasons, because the magazine didn't have room enough to tell the tale of the private days of Apple, which is what I was really interested in doing. And then I was on this leave and I got a call from Time asking me to contribute to a profile of Steve that they wanted to run in what became a very famous edition of Time, which was the Computer of the Year. I think it was the only time in Times' history where they'd picked an inanimate object to

• 34:28Speaker 02

  celebrate for their big annual issue. I worked on this profile of Steve. Steve was convinced that he was going to be named Man of the Year, even though nobody had told him that confirmed it, yes or no. But worst of all, the profile, which he hated, for very good reason, I might say in his defense, and I was appalled by, for different reasons, severed my relationship with Steve. Back then at Time, these things went through an editorial combine harvester. So what came out in the bail at the end probably didn't resemble very much of the straw that got fed in.

• 35:09Speaker 02

  And so the whole tone of the piece was malicious and nasty and underhanded. As I said, Steve disliked it, and it was one of the reasons I left Time. I felt very, very disenchanted by the treatment of it all. Sadly, as a result of that, really never repaired the relationship with Steve.

• 35:30Patrick O'Shaughnessy?

  Were you in awe of him?

• 35:31Speaker 02

  No.

• 35:32Patrick O'Shaughnessy?

  Have you ever been in awe of anyone?

• 35:34Speaker 02

  That's a difficult question. The people that I've known who have done incredible, remarkable things are also flawed individuals. And if you get to know them well, you also see that aspect of it. So seeing that up close makes it difficult to hold anybody in awe because you see the flaws as well as all of their accomplishments and virtues.

• 35:58Patrick O'Shaughnessy?

  Why were you not in awe of Steve? It seems like he's the person that the most people in our world were in awe of in living memory.

• 36:06Speaker 02

  I want to be careful here because I respected him. I admired him tremendously. I was well aware of the fact that he had achieved things later, obviously, as well, that I couldn't ever possibly have accomplishment. But I think I knew some of the darker shades of him, which made it difficult to hold him up as an object of unalloyed admiration. But he's a heroic figure, obviously.

• 36:38Patrick O'Shaughnessy?

  What's the role of monomania in all of these character studies? And I'm curious to tie it back to this idea of the outsider, the survivor.

• 36:47Speaker 02

  You see it now. This goes in generations. The monomania, when it comes to creating anything of value, it could be a piece of music, it could be a book, it could be a painting, it could be a company. Complete obsession with the topic at hand and walking out the rest of the world, eliminating every unnecessary distraction. There are downsides to this. People get hurt along the way. There isn't enough time for families or others or friends because of the monomania that you referred to. But then great things sometimes come out of it.

• 37:23Patrick O'Shaughnessy?

  Is the primary cost of monomania relationships typically?

• 37:28Speaker 02

  I suspect the answer is yes, or maybe for some of these people feeling that they may have like lived life differently if they had to live it over again because there were consequences to this monomania. But yes, clearly relationships. Evelyn Waugh, this, people don't really know him today, but a very famous British author who was capable of writing 10,000 words a week with ease, 10,000 good words, not rubbish. He said, "The greatest enemy to good art is the sight of the pram." The stroller in today's parlance is the sight of the stroller in the hallway.

• 38:10Patrick O'Shaughnessy?

  What about Frank Auerbach, the painter, a sea monomaniacal?

• 38:15Speaker 02

  Frank Auerbach has never got the recognition in this country that he deserves, although there's a retrospective of him coming here in the next two years to very significant museums around the country here. He was a refugee from Nazi Germany. He died maybe five years or so ago. I didn't know him well, but I got to know him a little bit. And he was a complete obsessive, completely obsessed with his art, painted every day, except he treated himself to a day, one holiday. For many, many years, he treated himself to one day off a year. And every year he'd go to Brighton, where there's a famous pier, it's on the south coast of England, and take the day off on Christmas Day.

• 38:59Speaker 02

  Every other day of the year, he worked. And I remember once talking to him, his wife had a house out on the English coast. And I asked him once at a dinner, I said, "So do you ever go out and visit Julia, your wife?" He said, "I've never been to the house." Now, this is probably 10 years ago. We were chatting and New York came up. And he said, "I love New York City. I just love it. It's so bustling with energy and going to Times Square and all the rest of it." And so this conversation was maybe in 2012, 2013. Frank, were you just in New York?

• 39:38Speaker 02

  And because, oh yeah, I went there in 1967. And he had this routine where he had, and I knew some of these people who posed for him or know some of these people, that all his subjects are still alive. They posed for him once a week. He had this regular coterie of sitters and he painted these same individuals for his figurative work over the course of 30, 40 years. And there's one of the subjects who lived in Venice, of all places, who once a week flew to London for his session with Frank, because I think the sitters found it like therapy, sitting for Frank. But he'd go into an utter meltdown if the sitter was late.

• 40:22Speaker 02

  And then similarly, with his landscape paintings, he painted the same landscape over and over and over again, interpreting it. But he lived for art. Really, there was no time for, he had a son, Jake, but there was no time for anything else.

• 40:39Patrick O'Shaughnessy?

  Do you get more energy from monomaniacs? You spend a lot of time around them. Do you prefer being with them over dilettantes like yourself?

• 40:48Speaker 02

  It's nice to have a mixture of friends and acquaintances, some of whom have tied themselves to a particular mask, others who are prepared to wander around and live life more casually. But I've always found it more difficult to be around people who, and I like them and enjoy being with them. But who appear to be doing nothing.

• 41:10Patrick O'Shaughnessy?

  What did Don Valentine see in you and what did you see in him?

• 41:14Speaker 02

  So Don was the founder of Sequoia. He took a risk on me, a van 1985, hired me to join Sequoia when Sequoia is a very small firm. We're sitting around this table here in your studio. It's probably large enough to accommodate all of the people who worked for Sequoia at that point. I was a journalist, been a journalist, but wanted to get into the venture business because I've become interested by it. And had met some of the people who were running these firms, all of which were very small at the time. And had written to five of them. This was in the days when you didn't send emails, you actually wrote letters. And had gone to see each of them, they were kind enough to give me some time.

• 41:58Speaker 02

  All save Don said, we don't really know what to do with you because you don't have a technical background. You don't have an engineering degree of any sort. You don't really have any technical knowledge. You don't have any work experience in a Silicon Valley kind of company. You've been a journalist, so maybe you should go and find a role in public relations or marketing or something like that. Which was not exactly what I wanted to do. And Don was more willing to take a risk. And the reason was fairly straightforward because he had seen people that he expected because they had big operating backgrounds in technology companies. A few of them come into the venture business and not be very successful.

• 42:41Speaker 02

  And then he was aware of some who had carved out very successful lives as investors. There was a fellow called Tommy Davis, I think, who started a fund called the Mayfield Fund. There was another guy who'd been an insurance actuary, but the one that Don pointed to more than anybody else was a gentleman called Arthur Rock, who just celebrated his 100th birthday. He was an investment banker at a small boutique here in New York called Hayden Stone. This is back in the 1950s. He had had the moxie to organize the original breakout and financing of Fairchild Semiconductor.

• 43:21Speaker 02

  And then in the 1960s, people won't know the names anymore, but he had helped finance Talodyne.

• 43:30Patrick O'Shaughnessy?

  Henry Singleton, right?

• 43:32Speaker 02

  Henry Singleton. Henry Singleton, who later became one of the early board members, our first board members at Apple. Scientific Data Systems. And then became the chairman, an original investor in Intel, day one. And then a few years later backed Apple. Don said, look, there's nothing in this background that would have suggested you be successful. That was the main reason.

• 43:54Patrick O'Shaughnessy?

  And what did you see in him in the early days?

• 43:57Speaker 02

  A job.

• 44:00Patrick O'Shaughnessy?

  What did he teach you?

• 44:01Speaker 02

  Don didn't believe in teaching. He had a survivalist instinct. So he just believed in tossing people into the deep end and see if they drowned. But I learned a lot by observation and listening. Good things and bad things. There was another gentleman at Sequoia named Pierre Lamond, who played a huge role in the rise of the semiconductor industry. And he too was something of an influence, but it was being in the middle of that milieu. Watching good things happen and bad things happen and gradually trying to form my own opinions about things.

• 44:41Patrick O'Shaughnessy?

  What do you think it teaches us about early stage investing? That a journalist with no technical ability and no work experience can be one of the best investors of that type ever?

• 44:52Speaker 02

  The venture business that I got into way back when is very different from the venture business today. There aren't many parallels. I don't know that I would flourish in today's venture businesses for a whole variety of reasons. I think it's become much more difficult. We had a variety of benefits back in the eighties and nineties. I think that began to dissipate maybe 15, 16 years ago that don't exist today. One of them being imperfect information. The pre-internet, unless you were very close to things, you didn't know what was happening. Today, because the internet and some of the stuff that we're talking about earlier. Everybody around the world knows exactly what's happening.

• 45:34Speaker 02

  Everybody's got access to the same information or more or less the same information. So that's number one. Number two, there are just so many more entities of all stripes. Individuals, two or three people banding together in a small firm. At the other end of it, huge mutual funds pouring money into it. That the very early stage private market is very, very different. Forty years ago, 30 years ago, it was possible if you were an individual to form a relationship, a real relationship, close relationship with the people that you were getting into business with. That doesn't exist today, particularly for a venture firm. There are just too many intermediaries in between.

• 46:17Speaker 02

  I'm not sure that the luck that I had back then. And I was also catapulted right into the middle of the one place in the world where all of this stuff was happening. So that's a huge competitive advantage too. I'm not sure that any of that translates today. I think moderately intelligent 14, 16 year old who had his or her wits about it would have been able to succeed in the venture business in the mid eighties.

• 46:44Patrick O'Shaughnessy?

  Do you think the ecosystem is healthy today?

• 46:46Speaker 02

  I think it is if you're a founder.

• 46:50Patrick O'Shaughnessy?

  Pretty good. I like the quote that you've said often that your favorite investment was Sequoia. What was going through your head as you took it over?

• 46:58Speaker 02

  Not to screw it up. The Sequoia that was around in 1995 was very different from the one that was around when I sort of stepped down in 2012, 2013. Number one was not to screw it up. Number two was to ensure that everybody who worked there felt that we were only as good as our next investment and that we couldn't rest on the laurels of the past. And then number three, take advantage of the new market opportunities that began to occur. Whether it was eventually going overseas as Silicon Valley's share of startup activity, though still obviously the best place to be, became smaller.

• 47:42Speaker 02

  So first of all, we went to Israel and we went to, most notably to China. Started another business called Sequoia Heritage, which is a very different business.

• 47:54Patrick O'Shaughnessy?

  And our Kevin Wellis, incredible talent.

• 47:56Speaker 02

  Yes, and Keith and our small and mighty heroic investment team then. I don't want to sound like Joan of Arc here. I felt doing right by our investors was really important. Most of our investments, investors were not for profits. I think making sure that we perform well for them. I didn't want to be in a business where if we didn't perform well, we still got paid very handsomely. I think that's part of the problem with a lot of the aspects, the financial service providers of all sorts of different forms, and it has been for a long time, which is

• 48:37Speaker 02

  the firm they've provided as well, but their clients may not, may have done as well just investing in an index fund.

• 48:44Patrick O'Shaughnessy?

  When I did this with Doug, he told me the story of that one fund that you fought so hard to get back to par over 10 years or something like this.

• 48:52Speaker 02

  We could have said to investors, well, look, you've had a lot of good times with us and you've just got to accept the fact that you've got a fund here that isn't going to make any money. I certainly wasn't wired like that. It was a matter of pride.

• 49:08Patrick O'Shaughnessy?

  What did you learn about working with someone like Doug that was so different than you? But you had such a fruitful partnership.

• 49:14Speaker 02

  Tolerance.

• 49:15Patrick O'Shaughnessy?

  And more.

• 49:17Speaker 02

  I think you have to adjust. When you're trying to work in a team, you have to try to understand what the other people around you need. What's important to them and feed that need with people who are wired, as you said, very, very differently. I think that's the most important thing I've learned about building a team or leading a team. I think today I'd be much better at it than I was 25 years ago, 30 years ago. And I learned a lot of that actually from the way that I did this book, maybe 10, 11 years ago, with a famous soccer manager.

• 49:52Patrick O'Shaughnessy?

  I was just gonna ask him about Alex.

• 49:53Speaker 02

  Called Alex Ferguson. I think one of his great skills was the ability to understand what motivated each of his individual players.

• 50:04Patrick O'Shaughnessy?

  How did you see him do that? I know he was famous for preferring players with tough upbringings.

• 50:08Speaker 02

  He's got this reputation, which is an unfair reputation of being very hard and harsh. And that was certainly an aspect of the way that he managed. But he was a man who didn't want to be loved. He didn't want to be feared. He wanted to be respected by the individuals who played for him. So he was there for them, which people don't understand, in their bleak, dark times, when they needed support, when they were feeling lower than a snake's belly. He was there for them. None of that really gets written about. There was an incident, I remember, I forget which year it was, but David Beckham had been playing for England in a World Cup competition where he got sent off.

• 50:51Speaker 02

  And the British press was merciless about Beckham's perceived stupidity. And Alex went to meet him at the Apple because he knew he needed an arm around his shoulder. Those sorts of things, little things that happen out of sight. People aren't aware of them. There are no cameras around.

• 51:11Patrick O'Shaughnessy?

  Do you think you were so interested in him for almost like autobiographical reasons? That description kind of sounds like you.

• 51:18Speaker 02

  He was much more skillful at it than I was. The reason the book came together was this, people, for whatever reason, had been badgering me to write a book about Silicon Valley. And I was always very interested through the Sequoia lens of what it took to build two things. One of which was a business that endured for ourselves for Sequoia, because there are all these tales of venture firms that had a period in the limelight and then blew up for whatever reason. The founders killed each other or the partners killed each other and they all split up and it all became ugly. And then also the byproduct of it being what it took to have an enduring standalone company that a firm like Sequoia could invest in.

• 52:00Speaker 02

  And I didn't want to do that through a Silicon Valley lens. And there are enough books about Silicon Valley. So I was casting around for the company or for an organization that had flourished over the course of multiple decades. I'd been a bit of a fan of Manchester United Football Club since I was a kid. Here was this manager who took them over, I think in 1986 and retired in 2013. When he took them over, when they're in bad shape and then established a record over multiple seasons, 26 seasons of astonishing success that will be almost impossible for anybody to duplicate. We had a PR guy who were, or communications guy who worked for Sequoia.

• 52:44Speaker 02

  And I'd shown him at that point when I finished the book and I showed him a draft of the book. And he said, well, I can't tell because I ghosted the book, ghost wrote the book. And this fellow said to me, I can't tell what's you and what's Sir Alex. I said, precisely.

• 53:02Patrick O'Shaughnessy?

  Do you believe in the great man theory of history? I'm asking this question because I'm very interested by institutions that endure and what you've learned about how the ones that have endured have pulled that off like Sequoia. And I'm also pulled to people, of course, like Elon, who you were an early backer and partner to and X.com, how they shape history. And it seems like we might have a few world historic figures alive and operating today. What do you think is the balance of shaping history between these world historic people, great men and women, and enduring institutions?

• 53:37Speaker 02

  The short answer to the question is I'm a great believer in the great person theory. All these people that we've talked about, whether you just referred to Elon or we were talking about Lee Iacocca or Steve Jobs, or you go into the political realm or the field of battle. It is about great leaders, great leaders. And obviously there are some terrible authoritarian figures that have cast black shadows over tens of millions of people and over multiple decades in different countries around the world for hundreds of years. And so for good and bad, I think the individual has an enormous impact

• 54:17Speaker 02

  on what is around him or her capable of, on the good side of it, not the dark side of it, persuading others to achieve what's perceived as impossible. I'm a huge acolyte of that theory.

• 54:34Patrick O'Shaughnessy?

  Do you think Elon is the great exemplar of that today?

• 54:37Speaker 02

  Yes, he may well be the greatest industrialist in the history of America.

• 54:43Patrick O'Shaughnessy?

  What would you say about him?

• 54:45Speaker 02

  I don't know that I have anything to add other than it's impossible for me to understand how one individual has been able to achieve. And I know he's a controversial figure, but I'm just looking at him through the lens of history and through an investor's lens. They have this phrase in Britain called gobsmacked. I'm completely gobsmacked by the scale of his achievements in a variety of different industries, which is the thing that sets him apart from others.

• 55:17Patrick O'Shaughnessy?

  What do you make of today's prevailing technology environment and how this changes all the things we've talked about? One of the other PayPal founders told me recently that he thinks people like Elon and other great entrepreneurs will probably do more things, more than one company, expand out of monomania because all these tools give them so much leverage. Do you think that this is like a true tear in history that we now have intelligence?

• 55:41Speaker 02

  I don't know. If you go to China, you will find the founders of companies, or if you go to, I think probably South Korea, which I know far less about, you will find that the creators of one company have really imperial ambitions. And the creator of a company is along the way, or they take their one company and convert it into, look at Xiaomi, that manufactures these cars today that exceed the quality and performance and other attributes of Porsches, but began in 2010 as a phone maker, as an Android licensee, I think. Creative people or these rare, rare people armed with this extraordinary selection

• 56:24Speaker 02

  of power in the tools that are at their fingertips or at the fingertips of the people who work for them, they're going to be able to do a lot more in the future than somebody might have been able to do in the past.

• 56:36Patrick O'Shaughnessy?

  What is your model of this technology? Like as an observer of it, and I'm sure interested observer, how do you tell your family about it and what it will mean?

• 56:45Speaker 02

  We don't talk about it. Well, not very much.

• 56:47Patrick O'Shaughnessy?

  It's kind of nice.

• 56:48Speaker 02

  People will always ask me, but I'm not a technologist. I'm not an AI soothsayer.

• 56:53Patrick O'Shaughnessy?

  But you were so good at seeing what was going to play out. Like if I think about so many of your investments, the thing seemed small, but it was then something that became like infrastructure that the, you know, Instacart or something that the world was built on.

• 57:07Speaker 02

  Yeah, you're being too generous. I had very little sense that a company could grow at the rate that some of these artificial intelligence companies have grown at today. I mean, it's beyond comprehension. I remember many years ago, this was at the dawn of the internet or probably after the dawn of the internet. And Tom Siebel, who started, a well-known entrepreneur and had been seen as a very successful entrepreneur. I remember him wistfully saying one day, his company is sold for whatever it was, $10 billion. And he said very wistfully, that was back when $10 billion was worth a lot of money. Today you look back and you say, whether it was Facebook's IPO or Google,

• 57:51Speaker 02

  or that was back when $100 billion was worth a lot of money. I think the idea that you can have a six-year-old company with trillions of dollars, nobody would have imagined that.

• 58:00Patrick O'Shaughnessy?

  Are you mostly excited about this technology or scared or both?

• 58:05Speaker 02

  I read what everybody else reads and have heard the boogeyman opine. And I think I'm probably a bit more hopeful than others. Again, I'm not an expert. I don't mean to diminish the dark side of what may or may not happen with AI. I do take some solace in the fact that Armageddon was predicted or a form of Armageddon was predicted when the first nuclear bomb was exploded. And fortunately, here we are, close to a century later, and that hasn't occurred. Or if you read all the stuff from the mid 1970s about the genetic revolution and how there were going to be scientists creating legions of individuals

• 58:50Speaker 02

  that they deemed suitable to walk on the face of the earth, that hasn't occurred either. And today, even though I'm absolutely certain that there's going to be enormous disruption in particular job sectors caused by AI, I think that it's going to create more jobs than are going to be lost. Everyone can say that this time is different, but there hasn't been a huge improvement in technology that has, in the last two or three centuries, led to lower employment in the long term. I mean, there've been depressions and massive disruptions in sectors, but overall employment has grown. So I'm a little more optimistic.

• 59:30Speaker 02

  I think there'll be a lot of jobs that get created that we couldn't categorize today.

• 59:36Patrick O'Shaughnessy?

  Because AI produces prodigious amounts of new text and writing so easily.

• 59:42Patrick O'Shaughnessy?

  I think the value of extraordinary writing is going up that can cut through the CF slop. How would you define extraordinary writing, having done quite a bit of it yourself?

• 59:54Speaker 02

  Again, you're too flattering and kind about that on that particular topic. It's hearing the unmistakable voice of the author.

• 1:00:02Patrick O'Shaughnessy?

  How do you do that as a writer?

• 1:00:04Speaker 02

  It's the same with the journey through life. The toughest thing, I think, for an individual, whether it's guiding them through what it is they want to do in life, or what they want to put on paper. It's being in touch enough with your inner feelings and inner voice to allow those to conquer the pressures of the expectations of others.

• 1:00:30Patrick O'Shaughnessy?

  Joseph Campbell said, "The privilege of a lifetime is becoming who you are, but also that that's the hardest thing to do."

• 1:00:36Speaker 02

  I wish I'd been clever enough to say that. I completely agree. I think that's the struggle everybody has. And it's also the struggle when you put things down on paper.

• 1:00:47Patrick O'Shaughnessy?

  Is there a moment in your own life that was the most important in becoming who you were? Like, the hardest part of doing it? It's so valuable to do, and it's so hard to do. It makes me wonder about what the hardest part was for you.

• 1:01:00Speaker 02

  I don't think I've done it.

• 1:01:02Patrick O'Shaughnessy?

  Why not? What's the barrier that's left between you and who you are?

• 1:01:06Speaker 02

  It's one of my many weaknesses. I've always been too prone to live up to the pressures or expectations from the outside or from others than to let myself run free.

• 1:01:18Patrick O'Shaughnessy?

  Is it a goal of the remainder of your life to do so?

• 1:01:20Speaker 02

  I'll try.

• 1:01:22Patrick O'Shaughnessy?

  I'm so struck by how unbelievably self-aware you seem, but then you're giving yourself poor grades that seem like objectively wrong.

• 1:01:33Patrick O'Shaughnessy?

  What is that? I'm just still struggling to understand.

• 1:01:36Speaker 02

  I don't know. Maybe it's the specter of my mother.

• 1:01:39Patrick O'Shaughnessy?

  Can you say more about her? We didn't talk too much about her, other than her doom prophecies.

• 1:01:45Speaker 02

  I owe her many things. She aroused my interest in art and a variety of things, but she would always find fault, no matter how good things or what I had done. I remember there was some newspaper coverage years ago in Britain when Yahoo became public, and there were some stories about me in the British press. I mean, she was convinced I was a crook. She was absolutely convinced that this police should come for me, because there was no possible way that I could have participated in anything like this that could possibly be legal.

• 1:02:23Patrick O'Shaughnessy?

  Did that hurt?

• 1:02:24Speaker 02

  No. By that point, I was more amused by it than anything else.

• 1:02:29Patrick O'Shaughnessy?

  Early, did it hurt that nothing you did was satisfactory?

• 1:02:32Speaker 02

  No, because it was just a fact of life.

• 1:02:35Patrick O'Shaughnessy?

  And yet, it seems to have echoed.

• 1:02:37Speaker 02

  Yeah. You never get the boy out of the man.

• 1:02:40Patrick O'Shaughnessy?

  What is the experience of stepping back from Sequoia because you were sick? What has that taught you?

• 1:02:47Speaker 02

  Well, first of all, I don't think leaders should stick around. If they have decided for whatever reason not to lead, they've got to get out of the way. So I went cold turkey, even though I tried to help Sequoia in what ways I could and was involved with a variety of companies, but it was as an individual contributor. But it was not as leadership. I got out of there as quickly as possible, because I didn't think it was fair for someone to linger in those sorts of meetings. I'd lived through that myself. So it's allowed me to do things. When I was running Sequoia, it was talked about monomania and obsessions. I mean, that was it. It was everything, every single day of the week. So it allowed me to do things. I could write. My wife and I, about 25 years ago, we started a foundation,

• 1:03:32Speaker 02

  so we spent more time on that. In recent years, I spent more time on trying to help San Francisco, which is where I've lived, pushing 50 years, not quite, but to turn around and flourish. Along with a wonderful co-founder, Griff Gaffney, I started a media business there as well, which is fun and, I hope, contributes to the life of the city called the San Francisco Standard. And then I'm involved with what used to be called Sequoia Heritage in a sort of advisory capacity. So there's plenty of stuff to do, which is fulfilling and unfulfilling at the same time, because while there are a whole variety of things, it's not the obsessive, monomaniacal focus on one thing.

• 1:04:16Patrick O'Shaughnessy?

  Do you miss it?

• 1:04:17Speaker 02

  Yeah, there are aspects of it. But I miss aspects of it, but I know full well that I would not want to return to that way of life.

• 1:04:27Patrick O'Shaughnessy?

  Is it the flow state of it that you miss? The feeling of total immersion and forgetting yourself?

• 1:04:32Speaker 02

  Maybe. I get that when I'm painting. It's a simpler life. You don't have to make decisions about how you allocate your time, because your calendar is commanded by some other force. The difference between having your calendar dictated by others and being in complete control of your calendar yourself is mine and they.

• 1:04:54Patrick O'Shaughnessy?

  What's your hope for the standard? What are the principles that guide it?

• 1:04:57Speaker 02

  Griffin, I didn't set it up as a not-for-profit. One of the things that we wanted to do was to show that local journalism can be a profitable business, number one. Number two, it's to have a vibrant, interesting, diverting, but reliable source of information for people in San Francisco and the Greater Bay Area, for people who care about that sort of stuff. Number three, I've been very clear from day one that news coverage, there's no proprietary thumb on the scale when it comes to news coverage. Some of the stories in the standard, I've been mentioned and referred to in ways that I wouldn't necessarily write myself. So that's fair game.

• 1:05:42Speaker 02

  But in the ideas and opinions area, it's center of right of center. And that's what this is. And that's a much-needed voice in San Francisco.

• 1:05:54Patrick O'Shaughnessy?

  As I think back to the book, and I put it down and wondered about what's going to last in me, having read this, the thing I keep coming back to, it's obviously selfish and context-dependent, is parenting. I have two young kids.

• 1:06:06Speaker 02

  How old are they?

• 1:06:07Patrick O'Shaughnessy?

  They're 12 and 10. They're approaching the end of that window where you described them as being

• 1:06:13Speaker 02

  You've already done the damage, Patrick. They're impaired for life.

• 1:06:18Patrick O'Shaughnessy?

  So I wonder, if you turn the whole exercise of exploring your own history and your family's history into how to think about the role of parenting, I'm curious what comes to mind.

• 1:06:29Speaker 02

  I think it's to arm the children with confidence.

• 1:06:32Patrick O'Shaughnessy?

  Simple as that? By doing what?

• 1:06:35Speaker 02

  I don't know. I have to think hard about the handbook of parenting. But I think it's to instill that feeling of self-confidence and freedom, and to try, as a parent, not to be censorious.

• 1:06:50Patrick O'Shaughnessy?

  Do you think, also thinking about the book, that an important lesson is that we cannot take progress for granted, positive progress?

• 1:06:58Speaker 02

  History is littered with examples of terrible things that happened over periods of time for millions of people all around the world. Russia, China, Iran, Africa, India. There've been terrible things that have happened over the last thousand years. I think there's very little that separates the human from the beast, and it's remaining human and not becoming the beast that is everybody's challenge.

• 1:07:31Patrick O'Shaughnessy?

  How do you think you were most changed by the exercise of studying your family and writing the book?

• 1:07:36Speaker 02

  Understanding myself a little better.

• 1:07:38Patrick O'Shaughnessy?

  And in the final analysis, what matters?

• 1:07:41Speaker 02

  I think it's two things. I think it's relationships with the people that you care about, knowing that we're all completely insignificant, no matter what the individual has accomplished. Trying to leave things a little better than they were before any of us got engaged with them.

• 1:08:00Patrick O'Shaughnessy?

  If you had to write a next book, what topic piques your curiosity?

• 1:08:05Speaker 02

  I've been playing around with this idea, which I don't know if I'll ever actually get around to writing, but I've been reading about it a fair amount. I'm very interested, weirdly, in Iran, Persia of the 1940s, the collision of individuals from inside and outside Iran that explains so much about the world we live in today. I think what I've been thinking about is not nonfiction, but a blend of fiction and nonfiction. Now, as I said, I don't know if I'll ever get the narrative and the structure and the composition right, but it's my view of what has happened in Iran.

• 1:08:51Speaker 02

  It's this collision of personalities from very different backgrounds and different parts of the world that have failed to understand each other. It's pretty fascinating.

• 1:09:01Patrick O'Shaughnessy?

  One of the great things about your thinking and writing was how short some of the very famous memos and things were, your what could go right understanding for a company like Stripe, where I understand a memo was quite short. I'm curious about that notion of compression and the power of compression. But if you were to sort of write something like that about the state of the world and give it to your grandson or something today, you seem so good at identifying like the things that matter that will determine where things will go.

• 1:09:28Speaker 02

  Again, you're too kind. For me, part of the training as a journalist, it's part of what I learned at college, being able to distill things to their essence, keep it very short, has stood me in good stead over the years.

• 1:09:44Patrick O'Shaughnessy?

  Can that be taught? It seems like more valuable than ever. So much information and abartment.

• 1:09:50Speaker 02

  I don't know. I think it depends a lot on reading. It's hard when people are fed a diet of a limited vocabulary. I am singling him out. But if you do these studies of the vocabulary of presidents of the United States, Trump's vocabulary is by far the lowest. I think he's got a vocabulary of about 2,400 words. Obama was maybe 4,500 words, common vocabulary. And I think having a huge vocabulary at your fingertips that you can select from allows you to express complicated ideas in a simple manner.

• 1:10:32Patrick O'Shaughnessy?

  I loved the book. I loved our conversation. I've loved all your writing.

• 1:10:35Speaker 02

  Oh, you're far too kind and flattering and gracious. The questions have been, as you can tell, thought-provoking and wonderful.

• 1:10:44Patrick O'Shaughnessy?

  I ask one final question every time I introduce someone. What is the kindest thing that anyone's ever done for you?

• 1:10:50Speaker 02

  Hell, me.

• 1:10:52Patrick O'Shaughnessy?

  So beautiful, simple. What have you learned from your life?

• 1:10:55Speaker 02

  Tolles.

• 1:10:56Patrick O'Shaughnessy?

  Common theme. Mike, thanks so much for your time.

• 1:10:59Speaker 02

  Thank you. Really good.

• 1:11:02Patrick O'Shaughnessy?

  If you enjoyed this episode, visit colossus.com. You'll find every episode of this podcast complete with hand-edited transcripts. You can also subscribe to Colossus, our quarterly print, digital, and private audio publication, featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at colossus.com/subscribe.

• 1:11:41Patrick O'Shaughnessy?

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