The episode with Jobs and Time was so fascinating in your history and I'm sure frustrating for you.
You know, sadly as a result of that really never repaired the relationship with Steve.
Have you ever been in awe of anyone?
You know, 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.
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? Like where do you think, what did you come away thinking after this deep study of your own family's history?
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 sort of unexpected gift of the writing and it came from an exploration of this exploration of my family's past in particular my parents and going back and excavating the deep memories of childhood and 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 that I do because unwittingly obviously every parent leaves an imprint on a child and I think that's obviously especially true during the formative years, whatever the formative years are. I'm no sort of child specialist or scientist, but those you know 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.
What were yours? So 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?
Well, I grew up as you know and as the book talks about in this family of refugees from Nazi Germany and Wales and refugees by definition are a minority. Jewish refugees in Wales during the 1960s and 1970s were a further minority. And I think if you grow although even if people look at me today and they think oh here's this old white man he's not a minority but and I can understand that but it's how an individual feels rather than how other people might look at you. But I think it touched me in a variety of ways. My parents had gone through these although they were never in the camps they got out 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 actually had survived the camps but they were refugees and in their own way had survived and 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 and 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 gives you well certainly gave me in retrospect I didn't understand it at the time a sort of drive and grit that I wouldn't have had without that particular atmospheric backdrop.
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?
It was definitely not the stories they told because they didn't tell the stories and 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 and the world you know 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 said you know when I was thinking about the book became interested in it was just broad sweeps. So I think it was much more the daily behavior, the reaction to events, the reaction to things, the sense that the doom was not very far away. And the fact that if horrors had occurred in the past there was a real need to be vigilant and wary about navigating daily life.
There was a couple 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. It's quite a poignant and interesting on this topic of survivor, you know, outsider early instinct when things are changing to take notice and not double down and stick around. What maybe tell that story and explain what you learned from that.
Well, the two individuals, Patrick, that you referred 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 province in southern Germany. He had fought in World War I. He had somehow or other survived the horror of Verdun. He had been given his iron cross and he was I think a great believer in the German state and in the security that the state offered and then much later in 1933 he lost his job. But somehow I think because 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 that in the state and the endurance of the state and the durability of the state and that eventually the storm would blow over. And he also had a pension and the pension was very important to him as a means for survival. And so I think it was a combination of all of those things that 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 forget there are any even if you decided to 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 visas. 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. And my maternal grandfather was cut from a different cloth. And he was again I was too callow as a youth to really understand this, but I knew him as a he died when I was about 16. And 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 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 was again in retrospect was that he was more street wise. He was more entrepreneurial. He 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 out by the skin of their teeth. They got out 72 hours before war broke out. So 72 hours later, they too would have perished.
Ramp is the only platform built to make your finance team leaner, faster, and better, saving businesses 5% annually on average, so you can stay focused on growth. Ramp just opened for business in the United Kingdom. So if you're running a business in the UK, you can now use Ramp's AI powered finance platform to manage cards, expenses, bills, approvals, and accounting all in one place. I run my business on Ramp, and so should you. Learn more at ramp.com/invest.
OpenAI, Cursor, Anthropic, Perplexity, and Vercel all have something in common. They all use WorkOS. And here's why. To achieve enterprise adoption at scale, you have to deliver on core capabilities like SSO, SCIM, RBAC, and audit logs. That's where WorkOS comes in. Instead of spending months building these mission-critical capabilities yourself, you can just use WorkOS APIs to gain all of them on day zero. That's why so many of the top AI teams you hear about already run on WorkOS. WorkOS is the fastest way to become enterprise ready and stay focused on what matters most, your product. Visit works.com to get started.
Rogo is the AI platform purpose-built for financial institutions serving tens of thousands of bankers and investors at hundreds of leading firms worldwide. Rogo's AI agents autonomously execute large chunks of your firm's workflows. They can screen deals, draft sims, run buyer outreach, and due diligence on data rooms, all with full security and compliance handled. Every action feeds Rogo Intelligence, the firm's context layer, turning years of deal experience into a secure, governed institutional memory that makes each new transaction stronger than the last. To learn more, visit rogo.com/invest.
What do you take from that? Like, what is the big lesson from that instinct, how does that instinct imprinted on you and on the people you've backed throughout your life and career written about?
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 saying that you can never have enough passports.
Do you feel that especially true now?
Say a bit about the state of the world, how you perceive the state of the world.
It's an uncomfortable place for minorities, the United States and Western Europe at large. It doesn't matter whether you're Asian or Muslim or black or Jewish. And you know, I understand the reasons and I want to be careful as well. I am not whining about anti-semitism. 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 2500 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 anti-semitism 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 you know in America I think my simplistic way of thinking about who feels safe in America is I think 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. 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 the 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.
If I force you to put on your optimistic or hopeful hat and thinking about the future as it relates to this problem.
Well, Viktor Orban was booted from office and he was riding high a couple of years ago. I think 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 in the next 18 months or after that are really going to shape how we're going to live in the next decade because the last decade has been 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. I think it's different in France with Marine Le Pen and the elections next year. It's different in Spain and it's potentially different in Germany.
Do you think that the internet fundamentally changes the potential for civility and political moderation because it so rewards extremes in attention?
And I think the three-letter answer is yes. I think it's been true of every form of new media that 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, much 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.
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. Like you should live the life that he was unable to or didn't quite. And that there's a 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. And back to the point about where does one person end and the next begin like the break from the parents is really important. And so I'm curious how you arrived at this method of yours, this first 14-year interrogation method, like when you first did it and why you find it so how you do it, like what the method is and why you find it just so impactful in understanding a new person.
I suppose I first came across it oddly in Detroit when I was a correspondent for Time magazine and 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. And in writing this book, we spent a fair amount of time interviewing Iacocca. 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 and 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 by 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 at some point in their family's history 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 and then I think 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 he was seen as an Italian immigrant.
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, is their drive and motivation go away or suffer?
Well, I want to answer the previous question a little bit as well about, you know, you asked why I when I've met various people and various founders over the years, spend so much time on their backgrounds. Many of these people are only, you know, 20 years old or 21 years old. You're covering a big percentage. You're not exactly going to be able to ask them about their life in their 50s. So it's just natural. It's 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.
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 and you were...
No, I think it's I try to paint when I have some time and I'm not a good painter, but I really enjoy it. And when you can when at least the way that I paint, you make marks in different parts of the canvas and the marks seem unrelated and you know, maybe it's a color blue here and a color brown there and you're putting these marks and dots on the canvas and 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.
In searching for those dots did you come to favorite questions that you always found yourself asking?
There's one that comes to mind which I've always found quite invariably 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 Sequoia who burst into tears when I asked that question. And it turned out that he had grown up as the son of an immigrant here in America. He was Hispanic and 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 had gone down to a corner grocery store with a pal of his and stolen some candy. And 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, and the man I interviewed was so chastened, so embarrassed by bringing shame upon his family and his father just burst into tears.
What's your answer to the question? What would you have done differently?
You're a good interviewer. People don't listen to answers very often when they interview people. I think I would have and you know I think every child of parents feels this in one way or another and I felt it as I was writing the book that I was embarrassed and if I could erase one thing it would be some of my interactions and dealings with my parents which I feel ashamed about today. But there's no going back you know I was you know and I spent the first 16, 17 years of my life with them. But there were many things probably that I wish and also when I was a younger man and just encounters with them that I wished had gone differently because I didn't really understand who they were and so be it.
Do you think that was mostly a natural drive to create your own independence like every child goes through with their parents?
I'm sure that was some of it. Arrogance was probably another part of it, a failure of comprehension of what they themselves had experienced and what had made them who they were, which I didn't understand.
There's this notion of very small deeds in the book. I think the character's name was Anna. Can you talk about what you learned about the impact of small deeds?
Well, it was more than small deeds. So, this lady that you referred to whom I knew as a child, her name was her first name was Anna. And when my father and uncle were growing up in Munich in the 1920s and the early 1930s, every sort of you know middle class, lower middle class household had a family servant. You know 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. And 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 and she was Roman Catholic and eventually left the employment of my grandparents and she married a railway worker in Bavaria who was also a Roman Catholic. They built their own house with their own hands and she and her husband offered they 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 were horrified by the children, these two. They were horrified by the Nazis. They did everything possible to help my grandparents and my father and uncle. And then after the war, my 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. And developed this very strong connection with her until she eventually died. And I remember going and staying in her house and the house and the story of this house features in the book as well as a young boy and surrounded by the specters of the Nazi past. But this lady was I think you know what they say at Yad Vashem when they bestow acknowledgements on all the people who help 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.
What did you learn from these categories of people? I think you called them the resistors, the silent, and the collaborators.
Yes. Well, I watched this. This is a spectacular series that came out maybe 12 years ago, shot in France. Maybe it's 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 you know 10 other participants that were in the Zoom room. I always used to look at each individual whom I knew on the whole 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 collaborating. It was a private 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.
How rare is it? Is it 1% the resistors out of 100 people? Like, how rare do you think that expression is?
I think it's very rare because bad things happen in countries when most people stay silent. Very few actively resist.
Do you think that most of the people that you've backed in your career would be resistors?
I'd have to think about that. I'd like to think so, but I'm not sure.
Can you talk about the role that Bill Deeds played in your life? And 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.
I've never felt I'm really good at something. That's not false modesty on my part.
Really? To this day? How can that be in face of the evidence?
Well, I think everybody is plagued by doubts and maybe competitiveness and no, I've and everything that I may have done and it's a failing on my part. I have a very difficult time celebrating good things and celebrating success. But anyway, back to...
I want to know why that is. Like why do you given that you're self-aware about it, have you ever tried to...
I think it's heritage. I think it's the fact that my mother always felt that disaster was always around the corner and doom was always around the corner. I mean, she died a few weeks before COVID and this, you know, my mother was the predictor of doom and 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. So in a way she died a few weeks before COVID and that was one of the great disasters. 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. So she was cheated out of COVID but I think it's that sort of sense of being one step away from the precipice.
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?
I think I've always felt everything is unfinished and could be improved. And none of it's ever been perfect. So, never a satisfied moment. 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 and you're diminished and you're reduced to being an insignificant speck.
What about feeling of pride for someone else, not so much for yourself? I mean, 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?
No, not necessarily. I think I've because 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.
I'm so curious about how for someone that's been involved in so many fascinating things, unlikely things, what jumps out as like the highest energy moments for you? Like 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.
I think it's family and children and all the moments associated with, you know, and I have 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.
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.
So I better give a bit of context to you. I grew up as you know in Britain and when I left college I really wanted to be a journalist and my goal was to work on one of the big at that point what were called the Fleet Street newspapers that this is a long time ago it's 50 years ago that everybody read and there were papers for you know different sections of the population and I wanted to work on one of the biggest, really well-regarded newspapers. But there were trade union rules because the unions had a big clamp down on the way in which they held the operators of these newspapers in a straight jacket. And one of the consequences was that the newspaper editors, they weren't allowed to hire college graduates 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. So 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 thought it, you know, 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 figure on which Evelyn Waugh had modeled one of his characters in his very sort of famous satirical novel called Scoop. Anyway, Bill Deeds very kindly responded to a letter that I'd written to him applying for a job at the Daily Telegraph and 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 he told me I asked him for advice and he told me that he what he had wished he had done as a young man was go to America and he encouraged me to move to America and I think that was the most salient I think that really helped propel me head in this direction.
So when you arrived here, what was the first big break or big move that you made that kicked off this?
Well, I got very lucky. I got hired by Time, right? And straight out of school and without any work experience and they were as an organization again 50 years or so ago 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.
The episode with Jobs and Time was so fascinating in your history and I'm sure frustrating for you. What did you learn? What happened? And what did you learn through that episode?
It's a painful part of the past. I had this is a maybe two 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 and I think it was the only time in Time's history where they had picked an inanimate object to celebrate for their big annual issue. So 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. And so the whole tone of the piece was malicious and nasty and underhanded. And as I said Steve disliked it and it was one of the reasons I left Time and I felt very disenchanted by the treatment of it all. And you know sadly as a result of that really never repaired the relationship with Steve.
Have you ever been in awe of anyone?
That's a difficult question and I think it's tilted to I'd really have to think about that, Patrick, to give you a really considered answer. You know, 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.
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.
I think I was 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 accomplished. 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.
What's the role of monomomania in all of these character studies? And I'm curious to tie it back to this idea of the outsider, you know, the survivor.
You see it now and this goes in generations. The monomomania 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 locking out the rest of the world and eliminating every unnecessary distraction I think is what and I think those are and again 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 monomomania that you refer to and but then great things sometimes come out of it.
Is the primary cost of monomomania relationships typically?
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 monomomania. But yes, clearly relationships. Evelyn Waugh this you know 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 which 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.
What about Frank? Is it our painter?
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. So he was a refugee from Nazi Germany. He died maybe 5 years or so ago and 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. He 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. 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.' And then now this is probably 10 years ago.
We were chatting and he was asking me where and we were talking about 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. And so I said, 'Oh, Frank, when was the last time you were in New York?' Because he said, '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 actually I think that all of 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. 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 and really there was no time for, he had a son Jake, but there was no time for anything else.
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?
It's nice to have a mixture of friends and acquaintances, some of whom have tied themselves to a particular mast, others who are prepared to wander around and live life more casually. But I've always found it difficult, more difficult to be around people who, and I like them and enjoy being with them, but who appear to be doing nothing.
Vanta automates compliance so your team can spend less time on security reviews and more time getting customers. Vanta cuts audit prep by 82% and gives you instant, up-to-date proof of trust without all the manual work so you can close deals faster and with less friction. Customers report a 526% return on investment and more than 16,000 companies use Vanta, including Ramp, Harvey, and Snowflake. Get started with $1,000 off at vanta.com/invest.
Ridgeline is the first end-to-end system of record with embedded AI for investment management firms running portfolio accounting, reconciliation, reporting, trading, and compliance on one unified platform. 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 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. And you can request a demo at ridgeline.ai.
What did Don Valentine see in you and what did you see in him?
So Don was the founder of Sequoia and he took a risk on me in around 1985 and hired me to join Sequoia when Sequoia was a very small firm. I mean, we're sitting around this table here in your studio and it's probably large enough to accommodate all of the people who worked for Sequoia at that point. And I was a journalist, had been a journalist, but wanted to get into the venture business because I'd 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. All 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 and 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. 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. And Arthur had organized, he was a banker, commercial banker or 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. And then in the 1960s, people won't know the names anymore, but he had helped finance Teledyne, scientific...
Henry Singleton and scientific, Henry Singleton who later became one of the early board members at, first board members at Apple, scientific data systems and then became the chairman and original investor in Intel day one and then a few years later backed Apple. And Don said, 'Look, there's nothing in his background that would have suggested he'd be successful.' And so that was the main reason.
And what did you see in him in the early days? Like what...
Don didn't believe in teaching. He believed in throwing people into, 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 and good things and bad things. And there was another gentleman at Sequoia named Pierre Lamond who was a very formative, 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 and watching good things happen and bad things happen and gradually trying to form my own opinions about things.