The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley With Jimmy Soni – #336

The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley

The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley With Jimmy Soni

Tesla, Facebook, YouTube, SpaceX, Yelp, Palantir and LinkedIn. What do all of these companies have in common? They were all formed, funded, or advised by a small group of men who founded or worked at one company, PayPal. Members of the PayPal Mafia as it’s sometimes called, and who include Elon Musk, Peter Thiel, Max Levchin, and Reid Hoffman, have gone on to drive innovation and entrepreneurship in the 21st Century. Yet for all their influence, the story of where they first started has gone largely untold. In The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley, award-winning author and biographer Jimmy Soni explores PayPal’s turbulent early days. He also reveals the stories of countless individuals and hidden figures who were left out of the front-page features and banner headlines but who were central to PayPal’s success. Jimmy Soni’s previous book, A Mind at Play: How Claude Shannon Invented the Information Age, won the 2017 Neumann Prize, awarded by the British Society for the History of Mathematics for the best book on the history of mathematics for a general audience. Welcome to the SuperCreativity Podcast, Jimmy Soni.

The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley With Jimmy Soni

For More of SuperCreativity Podcast By James Taylor

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The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley With Jimmy Soni

Jimmy Soni 1:16
James, thank you for having me. I really appreciate it.

James Taylor 1:18
So you reached out to me, we connected because we had Sebastian Mallaby on the show. And he was talking about the power law is great book about Silicon Valley, venture capital firms. And one of the things are just reading through your book, the founders, one thing that links his book and yours is they both completely blow out of the water, the idea of the lone creative genius, the instead look at kind of innovation, entrepreneurship through this lens of either creative peers or collaborative teams. So one thing is you had all these different options of how you could write and get into this topic. But what first attracted you to the idea of writing a book about PayPal? And why did you decide to write a book about the founders of this one company, the various founders, rather than just one individual like Peter Thiel? Or an Elon Musk, for example?

Jimmy Soni 2:06
Yeah, that’s a great question. I appreciate you picking up on on that specific thing that this this dispels the myth of one person in a garage, like hacking these companies together, assembling it together. You know, it’s interesting, I hit my last book was about a mathematician and he worked at his name is Claude Shannon, and he worked at Bell Laboratories. Bell Labs was one of these places that also dispelled the myth of the lone creative genius, because they had a lot of geniuses in one place at one time for a series of decades, not just like a short period, this was, you know, a decent chunk of the 20th century. And so I started thinking, you know, this is this, this whole idea of, of clusters of talent. It’s what I write this in my intro, it’s with the producer, Brian Eno called Sidious. Not genius, but serious, right? So I started thinking, like, what are other senior says, use the plural, little awkward, but whenever I started just thinking, what are other groups, there are a few that came to mind in the world of technology, entrepreneurship, there was General Magic, which was this incredible place, you know, a ton of incredible alumni, their product didn’t quite take off. But it was actually, the ambition and the scope was worthy of this just incredible documentary that was done that I think everybody should see. There was Fairchild Semiconductor, which is one of the valley’s more famous clusters, there was Xerox PARC, where a lot of actually like what we use on laptops and computers was first invented. I found really good and media meaning books or docs on those groups. And I didn’t quite find the same like, Hey, this is the condensed story for Pay Pal. And I thought of that as like, Wait, that doesn’t make any sense. Because like, we’re, you know, there, I don’t know, 200,000 tweets about Elon Musk in the last like, what? Five minutes? Right? Or hour? Right? How is it that no one went back and kind of excavated this moment. And it’s like these four years of his life, or the same for Peter Thiel, Reid Hoffman on down the line. And it just struck me like, you know, a lot of my projects come to me, and I’m sure this is true for the things you work on, like you spot like, for me, it’s an empty space on a bookshelf, right? You sort of like see the empty space, and you just, it bothers you. You just get you’re like, I just I remember when I was thinking about it, I just I would call friends and say, this makes no sense. Right? Like, this makes no sense that there’s not a book about this because it was this hugely interesting time. bubble, rise it you know, it sort of gets created, it bursts. All of these people live through that experience. They live through September 11. Together, they IPO the company, that company gets acquired, and then they go on to build YouTube and build Tesla and all the other things they did. Why hasn’t anyone done this? And when I couldn’t find a sufficiently good answer to that question. I just decided they answered for myself.

James Taylor 5:01
And essentially, as I was written reading the book, the thing I kept thinking about was a TV show, I watched probably every club around Christmas time Band of Brothers a TV show, I kind of just want to watch it, it’s kind of a thing, I just do it before Christmas, because there’s like 10 episodes is quite short. But there’s this, they kind of go through the forming stage, and you know, where they like each other don’t like and then the, they have a strong leader that tends to come out or actually a kind of pairing that happens. And it can go through and it really then you see this, this culture that is formed over a number of months and years out of battle. Essentially, I really the book, it felt like it was like just loads of these little mini battles that were kind of going on in this culture was crazy. Tell us because it for people that don’t know the history of PayPal, and you got a lot of detail. It was really initially two different companies, confetti and These were competitors that later became collaborators. So tell us, how are they cultures different? And why did they decide to join forces to what we can know as people today?

Jimmy Soni 6:11
Yeah, it’s your description is very apt. It’s it’s actually funny that you describe it with Band of Brothers. Because Reed Hoffman use that exact reference. In a quote, he said, because someone sort of talked about how they were like, Oh, the PayPal Mafia, this or the PayPal Mafia that and the problem with that phrase is that it actually reduces the team of several 100 people to just a handful of people. And it makes you think that they all think the same way about everything. I actually have my own misgivings about the phrase, I write about it. And I what I would regard as a pretty balanced way at the end, and there are some people who love it, and a lot of people who don’t really like it. And here’s the kind of effect that it’s sad. But Reed Hoffman use Band of Brothers, he said, he said something to the effect of and I won’t get the quote, exactly right. He said, You know, people tend to think that the PayPal Mafia-like we’re all hanging out together, it’s not really that it’s more like the band of brothers, we all went through this very, very intense experience together. And then when they were writing, the Times wrote this long story about in like the mid 2000s, or late 2000s, around the Pay Pal, alumni and Max Levchin, the CTO said, it felt like we were veterans of an intense military campaign. So your analogy isn’t just something you made up? It’s actually exactly how they feel about their own experience. Right. So you’re spot on, you gave a little bit of background. But you’re absolutely right, there were two companies that formed that merged together to become PayPal. So Elon Musk fresh off his first startup exit from zip to a company that he created in the mid 1990s takes the bulk of what his winnings meaning, you know, the bulk of what he made doing that company and invest it into a company called And, ambition is enormous. What it is, is the idea is like, basically, oh, we’re gonna take all financial services, and unite them under one banner. So if you want a mortgage, a loan, a credit line, if you want to do checking savings, if you want to do basically anything, financial is going to handle it for you. And the idea was, if you do that you reduce friction within the financial system, and you can reduce fees for people that’s, big, vast surpassing vision. On the other side, you have these two relative unknowns who have who are trying their hand at startup entrepreneurship, Max Levchin, and Peter Thiel. And their idea is, is a company called infinity and confited these basic dip their their signature product launched in 1999, was that you and I, if we were at launch would be able to whip out our then hot Palm Pilots, right, this sort of that that arrows, smartphone technology, although I think it’s an exaggeration, even call it a smartphone. It’s not very smart. I do.

The Founders

James Taylor 8:45
I do remember having one lovingly having one for a number of years, he was great lawmaker,

Jimmy Soni 8:49
knowing they were really popular. And their idea which was, which was able was at the time, it was seen as exciting and novel. And it was that the palm pilot had just introduced these little infrared ports into the corner of the device. And if you and I were sitting at lunch, and we needed to swap money, they built up a an application to do that in an encrypted way, meaning that it was a fully secure transaction. If I sent you 10 bucks to the infrared port, it would actually work. It was a real transaction. And that was their product. And they called that product, PayPal, they built an email companion to that product. And it turned out very quickly that like people didn’t want to use these glitchy infrared ports to transfer money, but they really love the email companion product. And so that is how their half of the company was built. In late 1999. These two companies go toe to toe to fight for users on an auction website called eBay. It is the most intense I mean, even in describing it to me they sounded tired when they talked about it the most intense like three to four week period where they are fighting each other doggedly for user growth. Somewhere in the middle of that fight. They basically conclude that they’re that they’re better together. They are apart. Not everybody agrees with this, but they sort of see the writing on the wall. And they’re like, look, we’re just going to bankrupt each other if we continue this fight, and so they decide to merge together and become one company.

James Taylor 10:12
So I thought it was interesting kind of this this, this merger that kind of happened. You can almost see the differences in the culture in the code. Of them, like one was built, I remember was was on was kind of like Microsoft kind of based. So it was kind of quicker to do things. You needed less people, but it was less flexible. The other one was on Linux based as well. And I just thought it was interesting in looking at the cultures like one we felt it was a strongly kind of geeky kind of thing. And another one felt a bit more consumer and kind of reading through the book. And I was trying to think, if I was in that organization at point, who would I naturally gravitate, who were the people that I would feel like I would like to hang out with, and the one person can read through the book. And obviously, everyone talks about Elon Musk was probably the one person I would love to just sit down when was Max Levchin because he felt to me like he had the soul of that business, like, I know you can write a lot of initial code. And last November, I was in Chernobyl, and I got a chance to visit Pripyat, which is where he’s from, which was the former kind of where the Chernobyl site happened. And you watch this journey of this person that gets out of Ukraine and moves to America and starts this thing. And this is the classic American story there as well. And I’ve thought Why is more not being written about Max Levchin and any kind of thoughts on that?

Jimmy Soni 11:41
Yeah, it’s funny. I you know, and this is for your listeners. I didn’t prompt this but it’s the your description of what you just said is the reason that I kick the book off with Max Levchin. You know, people might anticipate that because for a variety of reasons, you might lead the book off with Elon, right? But I was moved to start the book with Max because I thought of him as, in some ways, like a prototypical Silicon Valley story, but also an atypical mind. Right. He is someone who is able who goes toe to toe with Elon Musk, right. And they’re battling over serious engineering questions. And he I just found his story to be remarkable, you know, he emigrated to the United States. When he’s in high school, he finds his way to the University of Illinois, then finds his way out west and begins to build the company that becomes PayPal. And, you know, there’s this article that comes out about him well, after the Pay Pal years, and the person writing it was, I think, from the San Francisco Chronicle, they interviewed Peter Thiel. And one of the things Peter said, is almost a version of what you just said about being the soul of the company, Peter, and I, there wasn’t time nor room to fact check this. But he said something to the effect of, you know, a bunch of people who worked at the company decided to name their kids after Max, because that’s how highly they thought of him. Right. And I found that feeling again and again, when I interviewed people, you know, they they had, they looked up to him and his leadership in the company. Now what’s really interesting is, you know, he’s in his mid 20s. At this point, like the idea of of quote, unquote, leading a company is still something that it feels like it ought to, you know, being a different, somebody else, so many others more grey hair, right, but he is the founding CTO of convexity. He is with the company through its IPO, and it sailed to eBay. And he is the person who either directly or indirectly is responsible for a number of the company’s signature achievements. What is really interesting is that he know he’s one of the people that goes on to develop other things. He develops photos, photo application called slide that he sells to Google. And today, he’s the founder and CEO of a firm, which is the Buy Now pay later technology and has gone public. So he’s done this like multiple times. He’s he was one of the he invested in and help to sort of bring to life glow, which is a fertility application. I mean, people really in Silicon Valley’s like thought of as like leading light thought people think very highly of him. I was surprised that more of the world didn’t know about him like and that’s actually like, why threaded his story throughout. The other piece of it is that, at people’s core is about payments, right? It’s about James being able to send Jimmy 10 bucks right over email really efficiently. But what it really is about is making sure that James is actually James, that you are who you say you are, what Pay Pal is is a very, very, very big fraud fighting application that is like that what people see is the like glitzy interface in the front, a lot of that fraud, fighting a lot of the encryption, a lot of the emphasis on security comes from and is driven by Max Levchin, and the team that he builds it’s not him alone, and he’d be the first to say that and did but there’s a big part of this story that is around him really rigorously thinking through fraud and fraud fighting, that is actually what makes a company successful. You know, he’s also just like, For the person I like, he has a photographic memory and he’s brilliant and it was just fun to engage with him in that way.

The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley

James Taylor 15:05
And there’s some funny stories in it and we’ll maybe get into a few of them. I remember one Levchin when he realized that it was not the kind of Russian hacker groups getting in and trying to do kind of things to, to kind of different types of fraud. Like Levchin starts hanging out in the hacking chat because obviously speak, you can speak Russian as well. So it’s kind of like playing with them. And there’s, there’s loads of really quite funny, very kind of creative ways gonna go. I remember at one point, you were in a book that left you and said, as soon as he got on those hacker groups where he was listening and watching the conversations of people saying how they’re going to take money from PayPal, you also realize, you know what, least I’m in this room, all these other banks, they’re not even in this room. They’re all screwed. You know, they’re not even thinking about this conversation. So live chat is fantastic. I love whenever I get a chance to meet him. I would very much like to do that. But the thing that links I think your book really nicely with Sebastian’s book, The Power Law is, as I mentioned, you wrote about this book being a constellation of talent, but at the core of it is also these creative peers is combinations of two different but complementary people, Levchin and Thiele, for example. So the other person that kind of comes into it is maybe a controversial character for some is Peter Thiel. He seems to be like the one that could really go toe to toe with legend in terms of intellectual talk about that relationship between Peter Thiel and Max Levchin. What was the thing that kind of connected them, how did they spark off each other?

Jimmy Soni 16:35
Yeah, you know, it’s actually one of the things that to take it to take a step back. I love that you identified this specific thing, because I think there are there are these business pairings that we sometimes talk about, we talk about Charlie Munger and Warren Buffett, right, will talk about Steve Jobs and Steve Wozniak. And I think in that Pantheon should be Peter Thiel and Max Levchin as well. And I, by the way, I think, in fact, I know because they’ve spoken about it in other places, as well as with me, each of them has spoken very highly of what the other contributed, right. And so So a good example is that, actually, there’s a, there’s a bunch of great, great stories around this. But there, there is a way in which what Peter does for Max, and he’s spoken about this is give him call it the most ambitious rendering of what Max’s life could look like as an entrepreneur. So initially, when Max pitches his ideas to Peter, he has this idea that like, like, it’s kind of a what a fresh out of college entrepreneur who built several small companies in college, one that succeeded three that failed, it’s what that person might think, is a good idea, which is he wanted to build mobile encryption libraries, and then essentially charge a rental fee for companies to use these mobile encryption libraries. And I think that the connection with Peter does a couple things. One, it gives Max some investment, it gives him some money, some capital to actually like build the company. The second is that he gets him to think more expansively about what the product could be, and does basic things that even Max admitted to me that he wasn’t able to do, like write a business plan, right, and like, write a pitch deck. And so you have this person in Peter who kinda like in, like, outlines that vision can help to enable it in different ways, is a is a recruiter, you know, he plays this role of like, there’s all of these things that an engineer like Max either doesn’t want to do, or doesn’t feel like he’s the best at and into that into those pocket steps, Peter. Now, on the on the other side of it, you know, you do have somebody in Peter who is a like world class, talent, magnet and talent seeker, he can find people and often people who like, almost like, it’s almost like Moneyball for Silicon Valley, like he finds people that everybody else says like, that’s not gonna work. And he finds a way to bring them to their highest and best use. Max spoke, there’s just one really incredible moment where, and I don’t actually think I included the book. So for your listeners, this is not in the book. But you know, in the spirit of sharing it. Max is at one point, like a year into these two products, the Palm Pilot money beaming product, and the email money product. And there’s like some late night at the office, and Peter comes to the office. And he says, Max, what are you doing, and Max, like I’m doing some bug fixes for the for the Palm Pilot product. And they’re like a year into the launch of the product. And the email money product has like millions of transactions, and I think north of 1 million users, and the Palm Pilot product has around 12 or 13,000 users. And so Peter basically just goes like, wait, what you’re like, why are you doing bug fixes on this product that only has 12 or 13,000 users? You’re the CTO of the company like we need you doing these other things that are far bigger, right? And so there’s there’s this kind of clear call it clarifying effect that Peter will often have in the story not just with Macs but with other people where he is able to direct their energy in the place that’s going to add the most value. And, and you know, I tried in my own way, like do You’re the narrative to explore that and explain it a bit on how he does it. But it is there, it’s really there for Max because one of the things that Max is this great thing. You know, his his, he has an investment firm or like an investment fund where he used his to, like do angel investing called hVF. Hard, valuable fun. And, and I my understanding of the backstory is that he really likes hard problems. But he has this moment where he’s like beating his head against a wall about a problem. And Peter just like gently asked him the question like, well, what’s the point of this? I know, it’s hard, but is it valuable? And it was like this revelatory moment for X Ray said, oh, like, it’s not enough to just solve hard problems, they actually have to be valuable, like I might enjoy them. But it doesn’t mean that there’s value in the world about solving them, right. I think that this interplay between these two people was, I mean, it was critical, I don’t think it was absolutely critical. It created the foundation for the company that became PayPal, a company that is still in existence today. And that changed the lives of all of the people in the middle of the story. But that partnership really is is the glue that held certainly half at least half of the company together. At the end

James Taylor 21:15
of the book, you also mentioned you can give credit to different people. One of those was Ryan Holliday, who? I think you’ve had rain on the show. I’ve interviewed him on other things before. And he said he was able to kind of make an introduction to Peter Peter Thiel as well. Were you able to actually have a conversation with Peter to kind of talk about some of these things? Or was it still, you know, looking at what Pete had said in other magazines, interviews, conferences?

Jimmy Soni 21:37
Oh, no, I’ve done I did several conversations with him that were pretty lengthy actually, that where he, he would engage on the subjects in the book and some of the ideas and sometimes I was asking general questions like about the development of technology in the late 1990s and early 2000s. And sometimes I would ask him really specific questions, you know, because there were specific moments. A good example is that he is in New York on September 10, and flies out that night. And it is this very worrying trip, it’s a really hard trip, because they meet with investment bankers, and the investment bankers basically don’t understand the Pay Pal business. And they tell Peter and team like, we’re not gonna be able to take you public. And here are the 25 reasons we’re going to be delayed. And it’s a really hard day, and they catch what is even though there’s bad weather, they catch what is the last flight out that night. And the next morning, you know, they awake, and the nation is in chaos, and the world is in chaos. And so we were we dove into the kind of general trends in meaning technology development, but also really specific stories. Like I asked him to tell me like, What was it like, you know, flying back that day? And what was that meeting like? And what did it mean for the company’s future? And so there was we had a, we had a bunch of really great conversations. And you know, to his credit, he was really generous with his time. And he didn’t really, he didn’t restrict me from talking to anyone. Nor did he asked to see material like he didn’t say, like, I need scrip approval or something. He was very open and saying, you know, here’s what happened, from my perspective, you should talk to other people.

James Taylor 23:05
And he one of his stories was the recount. I’m not sure it was from the interviews or people can have previously heard about the story was how they came to arrive at the office for Thiele capital, and see 1000 Sand Hill Road, which I thought was a very kind of, like fake it to make it into a bit of creativity as well. So can you tell us that story? Because I love that little bit? Yeah.

Jimmy Soni 23:26
It’s great. It’s it’s, you could you could call it like a hackers approach to trying to get the right address on your business card. Right. So one of the people that that Peter hires very early on is a gentleman named Ken Howery. Ken and Peter had connected because Ken was a Stanford undergraduate and Peter had been back on campus for a couple of Stanford review events. And they stayed in touch and Peter offered Ken a job working with to Capitol and one of his inaugural assignments I don’t know if it was the first but it was one of the first was we need an office and it’s really important that the office have a Sandhill Road address because they don’t lead people to take us seriously because at this time, that real estate meant something right it really was it could noted you know influence and and and respectability and you you are you are a somebody. So the problem is everybody wants addresses there. And so Ken how he told me the story of how he spent basically a full day just like going sort of door to door like looking at office spaces that they either couldn’t afford or weren’t available. And it gets to this one address. And the person who owns the building is outside his name is Tom Ford. He’s actually kind of a call it like a like a real estate legend. You know, he’s passed, but he he had scooped up a bunch of real estate in that area. And one of his quirks was that he really liked would go outside and if he saw something wrong with his property would fix it himself. He was like he was a very, it was sort of a Midwestern ethic about him, right? He meets Kenari and Ken says I’m looking for an office he’s expecting like there’s no availabilities. No vacancies, and Tom Ford says, Well, come on, let’s go. Let’s go take a look at the map. And he looks at the map of this particular property, and he spots a clause is not spoken for. And he says, Well, would you be okay with a with a with a broom closet essentially and Kansas will? Sure let’s take a look at it. And that is the inaugural to capitol office because they retrofitted broom closet. Were kind of how we actually did by the numbers to put on the outside. There were no windows. And Mac’s told me the story. He said, No, I said that. I told him the office story. And he said, No, I remember that office. He said, sometimes if I was working in there, I had to suck in my my stomach and push the chair up against the table so that somebody could pass by me that’s how thin it was. It was actually a closet. It was not an office

James Taylor 25:38
are wonderful. And there’s lots of other ones that this as well. But also, it’s nice about some of these little strange kind of quirky things ended up resulting in inventions which we deal with every day, I think Sanjay Bhargava, inventing authentication using bank payments. So with this this problem that people were having, how do you authenticate someone that they are who they say they are. And just by sending these to open a micro payments, you know, we’re thing that and we can know this, but that can it came from someone sovereign, but I think the other one was the sending money by email kind of early on. It was almost like it was a, you know, they they kind of created a but they didn’t even think anything of it. It was not even so there’s so many stories in the book, where they kind of created these little things, little side things, it wasn’t really a main they had solved a little problem. And these became the main thing as well. I thought it was fascinating.

Jimmy Soni 26:30
What and I would argue this probably one that everyone who’s listening is used at some point in the last 24 to 48 hours, which is CAPTCHA. So the first commercial application of the captcha, these little tests that you have to use to prove that you’re human, like if you have to find a fire hydrant. And there’s like a bunch of things that are not fire hydrants that the first app commercial application of that was at PayPal, it was how they fought bots that were creating fake PayPal accounts. Because what was happening is all these bots were creating PayPal accounts in order to cash in on bonuses, you needed the ability to force someone to prove they were human, or meaning force a computer to prove that it is not a computer. And they developed the captcha and obviously that is just standard, you know, throughout, it’s changed a lot for obvious reasons. And it’s gotten visual, not letters. But it is fundamentally the same technology that was first applied there. And it was this this thing where they had a problem. And they had to come up with a solution really, really fast to to fix it. And a series of those solutions still dot the landscape of financial services today. And I just I wanted to dive into the creativity of how that happens. 

James Taylor 27:38
And one of the things that you often feel very strongly in the book is, these were, they weren’t long hours, they were working all that they were doing all nighters all the time, as a written thing would accompany work like that today, with a young company with, you know, 1920 21 year olds, would they work in that same way? Do you think that ethics still is there in in tech and Silicon Valley? Or do you think that’s something that we can look back in the past and say, we will get mad men and 1950s?

Jimmy Soni 28:10
You know, it’s a really good question. And I I, my disclaimer is I don’t work in technology. Right? And so I don’t have to, I don’t, I don’t, I’m not sure that my answer will be accurate. What I can tell you is some of the feedback that I’ve gotten from people who do work in technology about the book. And I had this one person write me a note. And he said, You know, I’m glad that in the book, you didn’t run away from writing about how hard it was, and how long the hours were. You didn’t glorify it, but you didn’t dismiss it either. And what this person was saying was a version of what I had heard from other people, which is, if you are trying to bring a new thing into life in the world, it is often the case that it doesn’t happen within a contained number of hours every week, that the story of startups whether they want to talk about it publicly or not, especially at the beginning, is the story of just like gratuitously hard work, right. And I think that people maybe you know, today we’ve sort of we’ve had evolutions on this front, we know that there’s some value in the brain taking a break, we have more science to back up the value of rest. But I think that even in the face of all of that, there is still something about the startup culture that is just about like working to bring your vision into reality, no matter how hard it is, and knowing that it will be hard and there will be long hours. Do I think that’s always positive? Probably not. And I wasn’t casting a moral judgment or making a recommendation when I was writing the book. All I heard was just story after story of Yeah, we go home and Friday night and like everybody was expected to be in the office on a Saturday. And I and I will say like, I I wonder how one could do it another way, especially in the earliest moments where you’re just trying to have traction, and there’s so much to be done and the team is so small. It seems to me that it would be really hard to accomplish it other wise. But I also, you know, the disclaimer is maybe there is and we know that there’s another type of story to be told. But I can’t think of a major technology company that didn’t have this kind of intensity in its first, let’s say, one month to 24 months, it would seem to me to be almost inconsistent with by that kind of world of work.

James Taylor 30:20
As I was reading it, I was thinking, Well, you know, we’re here now, but work life balance that’s going to push more. And I’m reading I think, what if that? I mean, you know, you’ve got a young daughter, I believe, and you know, what about that young parent? How would they deal with and I know that word, the word young parents working at the thermostat? And I thought, how did they do it? Because I can understand maybe the, you know, the young 25 year old single person doing all nighters and drinking Red Bull, but there was people there who were parents, you know, they had other responsibilities?

Jimmy Soni 30:49
No, and I’ll tell you the honest answer, the honest answer is it was really brutally hard. And the people that it was hardest for or was were parents, because you had a senior, you had senior managers who didn’t have kids, many of them. And then you had a group of people who didn’t have children. And I spoke to them. And I actually, it’s funny that you say that because I as a parent, I would ask them, I said, Look, you’re one of the few parents like on this roster. How did you make this work? And to a person? The answer was, it was just very, very hard like it it strain families, it was difficult it was it was a period of their lives where you look back and some of them describe Hey, pal, PTSD, right, then, like, that’s how hard it was. But they also said, and this is to the team’s credit, one of the one of the people I interviewed who was apparently had look, was it difficult? Sure. But one of the things about PayPal was that if you’ve got your work done, and you and you were effective at what you did, you know, it was a culture where like, you could actually set more of the rules for yourself in terms of hours and timing, then people would say, so, meaning this person was saying, like, you know, they kind of knew that I knew my swim lane very well, and that I would get my work done efficiently. And then I could go off and work and do whatever I wanted to do. It wasn’t necessarily about clocking in at nine and clocking in at five, or you know, clocking in and out and clocking out at 9pm, it was much more about Dude, are you effective? Do you get the things done that you say you’re gonna get done. But I will say the people I admire most in the story, are the people who were young parents of young children at that company worked so hard during this period. And you know, my hat’s off to them, because I’m not sure I could have done the same.

James Taylor 32:27
Now, I’m probably kind of arriving the gorilla in the room. Elon Musk, when you kind of went out, it can kind of go directly into the Elan, and there’s some stories there. And obviously, his character comes bass very strongly. But there was something else that linked all the characters in this book was as well as just their intellect and their drive and their ability to put in the hours the hard work was their curiosity. And you describe in the book Elon Musk having an aha moment where he reads the Hitchhiker’s Guide to the Galaxy, I think, when he’s younger. And he said, a lot of times, the question is harder than the answer. And if you can properly phrase the question, then the answer is the easy part. So going into this book, what were the what was the what was the defining question that you were looking to try and answer you were trying to kind of get to the root of rather than thinking about us, because there’s so many different ways you can you can go into what was your guiding style in this book?

Jimmy Soni 33:23
Yeah, you know, it’s a good, you know, pardon the pun or not, but like, it’s a good question. I, I would always think about when I was writing, I would always say to myself, like, how does this particular moment or scene help explain how the company came to be? Right? Because the temptation is to do what a lot of people do, which is focus on controversy, because it sells or to focus on, you know, the high profile figures because they sell, right. But I would try whenever possible to return to the question of what I’m writing about is a four year window with one company and there are a lot of people who made that company possible. Does what I’m writing serve a purpose here? Right? Meaning does it serve to advance the story of the company of Pay Pal? One of the things that people will notice if they read the book is that after Elon is departure from the company in late 2000, I don’t actually write about him all that much. And people might be like, Oh, I wanted that, or I need that. And for my, for my purposes, it was always well, he’s not in the company anymore. He’s doing other things. So he’s not sort of directly relevant to the Pay Pal story. And I think that like that question, kind of always got me back, which was I’m not telling the Mac story or the Elan story or the reed Hoffman story. I am telling a story of several 100 people, does this serve that particular purpose and mission? The Hitchhiker’s Guide to the Galaxy thing is fun. And you know, I will say that There’s an irony in having spent this much time thinking about what is arguably like today, the least interesting part of his life, meaning what other people are interested in, right? Like, I spent a lot of time, you know, examining understanding, talking to him about the years call it like 15 to 2829, right, like there abouts. And it’s this very generative period in his life, you know, he goes to, from one, college to an E transfers to the University of Pennsylvania, he gets accepted to Stanford decides not to go to grad school, builds his first startup then builds a second startup, he almost dies twice, right? Like there are all these things that happened in his life. But like in the last two weeks, all anybody wants to know is this this sort of his perspective on these other matters, right contemporary technology with his acquisition of Twitter. And I will say it’s actually it was, it’s been really helpful to have explored the early years of this person around whom there is a lot of discussion and chatter, because I came to appreciate that many of the, we take for granted so much, so much of what he’s done and how to overcome. And it strikes me that in a different way, but in the same way that you expressed about Max Levchin story Elon is is a classic immigrant entrepreneur story, right down to the details, right? comes here with very little goes very far. Doesn’t Know anybody has to build his his success and his Rolodex has helped along the way from different people has teammates who are interesting and vibrant and colorful. But just in the same way that Max is a story of someone coming here with very little and succeeding, Elon is the same. And in a way, it was a real privilege to explore the early, you know, the, or the different the early years, the years that weren’t, you know, the Met Gala? They weren’t, they weren’t what you see now, because you learn so much about what a person is, when they’re making those choices, you know, and asking him about, how did you how did you decide to go from this to this, and not talking at all about the things that are going on today? That was a great gift and an unreal, fun part of this project?

James Taylor 37:11
And as I was reading the book, and I was thinking, well, what would if I was to gift someone like three books to understand Silicon Valley nap time, probably I was thinking of it like this book. Give them you know, Sebastian Mallaby his book, I think it’s great to understand the money side of things. And the third book, which kind of links on to this, which is your commission on writing this book, which is talking about how did this company, not just the individual that the company, is creativity, Inc, by Ed carrier, because that’s really about that’s really about then it goes to the culture. And I’m reading that book he talks about, it was almost like, like baking a cake. And like, just, you know, you don’t want too much of one ingredient, you want this and it’s like these things. You want the salt and the sour and the spice and you want all these kind of things together and reading the book that I got that sense there was all these different flavors, these different tastes of people within it. And on their own. So many skills be highly overpowering. But when you put them together, they actually they were actually pretty cool. So I’m gonna go back to what we talked about creative pairings. And in this book, you pay a tribute to editor Alice Mayhew at Simon, who passed away during his junior writing this book, you also had a contribution with the late Jane will Entus on the book, Jeff carousel. Talk to us about how did these pairings augment your own creativity, your creative or how do you enjoy working with these people? Because this is these are your creative powers these editors nice,

Jimmy Soni 38:40
right? Yeah, you know, Alice was a was a giant. I’m glad you you mentioned her, you know, she was like, she was like, the she was like, Simon and Schuster is Lebron James. Right? She was like the person there who has worked with a lot of the writers that I grew up reading and admiring, you know, Doris Kearns Goodwin, Walter Isaacson, like the biggest people on the planet, former presidents Supreme Court justices, you worked with Alice Mayhew, and it was a rite of passage, because part of what people know about Alice and what has been written about her in public, you know, and she is very hard. Like, she will just flat remember, there were so many times when she would just flat out, call me out on something or just like, take, like, send back an email. It was like how, you know, how could you do this? And it was in service, though, of producing a book that was better, because she was willing to have that level of honesty with with her authors, right? It was actually one of these funny things, because there’s this like alumni, not alumni group, but you know, informal alumni like people who had worked with Alice. And as I got to know some of these people, some of them are, you know, 1020 years older than I am, I’d find out that they actually had the same fear that I did whenever they write to Alice because they never knew it was going to come back right. Because she was so bracingly honest. But she helped to She lit the place on fire in the sense that, you know, I can’t I don’t even know how many books have books, the first one killed surprises and were made into movies and like had this kind of big bigness about them. Right. I mean, Walter Isaacson was at Steve Jobs, deathbed. And that was the book that Alice helped to edit. And I think the biggest thing that she did for me with this project, is that she got it right away, because it’s sort of hard like you sort of are pitching it and you’re like, Pay Pal and be like, Pay Pal. That’s not that big of a deal. Like, what’s the deal here? She understood right away. She said, No, this is about like the founding period of this generation of technology entrepreneurs. She got it, believed in it, fought for it, and was a real advocate. Like she would say she would make analogies to me in emails that I would write to her like, I remember the last email she wrote to me before she passed away by Senator chapter one, which is this like, really, like kind of, you know, a lot of Hurly burly a lot of stuff happening. And she wrote back and she said, I felt like I was there, though. I’m glad I wasn’t most of the time. That’s great.

James Taylor 41:04
Story. She was getting into the story.

Jimmy Soni 41:07
Exactly. And she’s like, that was great. And then she also said, you know, Edison would be amazed. Because I think she understood that innovation and this type of creative work. It’s not it’s not tidy, right? It’s really messy. And it can be very their egos and personalities can come into the mix. And so that that was also the Edison story, right? This is a sort of larger than life figure had his hand and everything was very, very exacting and demanding. She saw these historical parallels. Working with her, helped me improve as a writer, I mean, because you just had to bring your A game like it was just one of those like you didn’t send bad work to Alice Mae, you you just you couldn’t

James Taylor 41:43
find that. And then the work you did with Jane Mullins, I didn’t know about this. This is a bridge or in in Brooklyn. Yeah. carousel carousel. What was this collaboration was this was a kind of CO CO writing collaboration.

Jimmy Soni 41:58
Yeah, it’s so random. I mean, it’s the most random, it sort of shows do these projects come together? So I had my daughter six years ago, she fell in love with Jane’s carousel in Brooklyn. It’s this carousel on the waterfront right in your neighborhood called Dumbo. And she, I, my daughter would just keep writing this thing. And I mean, like we wrote it. I mean, I’ve written an obscene number of like, hundreds of times, right? Because it was like one point, there’s like nothing to do. It was like cold and you go to the carousel, because it’s somewhat indoors, and you can, you can make a day of it. So I kept writing this thing and noticing that it was in much better shape than a lot of other carousels in New York, and that it was just better. Like it just the colors are more vibrant. The whole thing was amazing. And I wrote Jane a note, I just wrote, I wrote chain and email, I found her email address. And I just sent her a note and said, you know, thanks. It’s like, I think this really cares. I was really busy. My daughter loves it. And here’s some photos. And you know, I’d love to learn more about it. And she was great. She wrote back and said, Let’s have lunch. And so we started to get to know one another. And I said to her, I was like, because I learned in the course of that that the carousel took 30 years to restore, and she did the restoration herself. She was sanding the carousel down with exacto knives and discovered the original color of the horses so that she could recreate it and do what she called a historically faithful restoration. It was an amazing process. I mean, amazing. But I couldn’t fathom one person spending 30 years working on a carousel restoration. And so I said to Jane somewhat offhandedly. But let’s sort of half off handedly, I said, you know, you should really do a book about this, like a coffee table book. describing the process of restoring the carousel like this is a historic carousel was built in 1922. This year is actually the 100th anniversary of the castle. So it’s been around for 100 years. It’s been through, you know, World War, Great Depression, etc. Actually, sorry, World War, multiple other wars, things like that. It was in Ohio, it almost was almost lost to a fire. You know, there were all these things that happened to it. And so this is like a dramatic story of this carousel. And she said, you know, people have talked me about writing it. And I don’t know. And then we just kept talking and one thing led to another, we decided to do it together. And she was a packrat. She kept all the archival material, the images, the photos, she actually kept the exacto knives in a box of exacto knives. I worked with her on a tragically she passed away just before the books debut. But we were able to capture the actual story of the making of the carousel. And it’s you know, it’s a book by Pheidon just incredible company that were the collaborative with her on it. And, you know, to my mind, I think the thing that I admired about her is actually just the same thing I admire about some of the other figures that I wrote about in technology, which is, endurance is at the heart of a lot of these stories, right. So creativity isn’t just about having the spark or having the apple hit your head. It’s actually about enduring. It’s about deciding that you’re going to bring the thing into existence and knowing that you’re going to face about a million obstacles between here and the finish line, but deciding to go anyway, that sounds like a cliche, except that the cliche turns out to be true in every act of creation of anything significant ever, right? Whether it’s the iPhone or Jane’s carousel, they all have this. They have skeptics. They have doubters. They have forces opposing them. You wouldn’t think this, but there were all these people who live in Brooklyn who did not want a carousel in that site, you wouldn’t think there’d be any opposition to a carousel, but there was huge opposition to it. So if you had to become a political campaigner to fight for the future of the carousel, I think of endurance is one of the unheralded virtues within creativity, it you have to have it without it, that the creative thing can just be an idea on a page.

James Taylor 45:27
I’m so glad, because I’m co writing my first book just now. And the other writer is a writer who lives in in New York, in New Jersey. And it’s interesting kind of working with her she’s a journalist is her background. So she’s very good at like, focusing on like, deadlines. And and I’m not, because I’m a professional speakers, my main thing, and I’m used to getting on stages and telling stories to an audience and having that interaction, and she’s doing it in the written word. But it’s just, it’s an interesting kind of working with someone who’s very, very different from you and thinks in a very different way from you. And one of the things my career that we’re working on is that she’s very good at just drilling, drilling, digging, digging. So when you were working with Jane, how are you complimenting just from from a technical standpoint, we you sitting down with her and you essentially her her? I was gonna say a scribe to work in getting all the things from her or she kind of building out things, and you were helping structure, what was the what was that relationship? Like?

Jimmy Soni 46:29
Yeah, you know, it was more than that. It was, it was two things. One is that, you know, when we first started working together, I think in my head, I had an idea of what the story could be. But the more she would share, I would actually just help structure the tale in a way that like we had a beginning, a middle and an end. But the actual interaction was that we would sit and I would interview her. So I had these long interviews that we taped, where I would say, Okay, let’s get to the part where the carousel arrives in New York, and it’s basically just survived a fire and it looks like, you know, junk and you’ve just bought this thing randomly. Let’s walk through what was the day that it? How was it? What did it look on the day of arrival? Where did you ship it? What did you do? How did you begin? And so, you know, I think I asked all the questions that somebody looking from the outside in might want to ask, and then what we would do is we would just sit for these conversations, and then I would go off and write stuff. And the idea was to pack as much, you know, people buy cognitive books for different reasons than they buy narrative nonfiction, or you know, they’re buying it mostly for the images and that sort of stuff. But what I wanted to make sure is that 100 years from now, if someone ever wants to know the story of the carousel, they get as close to Jane’s version of it as they could, based on what she shared with me and the documents she shared with me and the memos and the notes and all of that. And that’s the the principal interaction was I was basically interviewing her I was sort of doing with her what I did with Elon, which is, let me ask you about some things. And I’m going to ask you some questions you’ve probably answered before. But I’m going to ask you a lot of stuff you haven’t actually been asked before. Or I’m going to ask you to go in the Time Machine and take me back, you know, to this date. And like, let’s go back there. And in both cases, whether it’s sort of January lawn, you know, it was fun, like these are these were fun conversations, because I was asking them to sort of, again, go back, it was more nostalgic, then, you know, where were you on this, this in this date, it was more like an impressionist paintings. Give me a sense for what this was like.

James Taylor 48:29
And enough time has passed. So some of the sharpness has maybe come off in a good way and about as well. This whole episode, we’ll obviously be talking about creativity. How do you keep your own thinking fresh? What influence do you try to surround yourself with all the time?

Jimmy Soni 48:46
Yeah, it’s a good I wish I had a better answer to that. No, I look, I read a lot. I, you know, almost always in the middle of three different books at one time. I would say that, that I’m a big issue. For me, it’s, it’s about I suppose that I do two to two or three things to keep the creativity bustles relatively fresh. One is I I love documentaries. I’m not a documentary filmmaker or anything. But I watch a lot of documentaries. And I find that that especially when I’m tired and I like don’t have the the sort of zeal to read a book or whatever. I find that docs are a really good way to just like kind of explore different things that I wouldn’t necessarily have exposure to. You know, there’s just so many good documentaries that are actually underrated and under watched. Like it’s funny because they don’t have the same kind of massive theatrical quality or theatrical release that a lot of films do. But I love documentaries. So that’s one one way

James Taylor 49:47
I guess we’re in a golden time of documentary making. Yeah, it’s almost tell me about the vowel in the documentary which is supposed to be incredible, which I think is also in Brooklyn or New York, certainly. So we are pretty Golden Time of the of documentary making.

Jimmy Soni 50:03
And I think that what it allows it allows you to do is it allows you to take stories in one genre, but make them appealing to people in a totally different setting. So a great example is, you know, I’m not necessarily somebody who knows the world of music super well. But the documentary Defiant Ones isn’t about Dr. Dre and Jimmy I Avene. And in Jimmy IV is the founder of Interscope Records, and together, they help to create beats headphones. Now, what I like to know to know about their lives, or like their entrepreneurial lives, not really, but because HBO did it as this four part very, very well done documentary series on them, I was exposed to a world that I otherwise like didn’t have a lot of, like, you know, and then like, the roadmap for right to understand producers, or to understand lyricist or that sort of stuff. So that’s kind of one thing. The second thing is I tried to look for, like, I can’t read a study like, like, if I, if I noticed a trend, I’ll sort of nerd out on the trend to like, let’s say, like two or three to the two or three book level. So like, I’m super interested in like nuclear energy right now, right, because I think nuclear has gotten a bad rap. I think that we kind of conflated nuclear war with nuclear energy, it sort of has a branding problem like it, you know, we think of Hiroshima. But like, there’s actually sort of like boring work in reactors that needs to be done. And I think there’s some real power there. I so I’ve been reading books about nuclear energy, just because I want to learn more about it. So I sort of tried to go to like, what I what I think of as like the two to three book level on any subject. And then the other thing I think, is, from creatively, I also always try to think about what project or projects I’d want to be working on, I do find that like, if I don’t have something that I’m actively like, creating my creativity, muscles actually atrophy because there’s no application to the stuff that like it, I kind of need a goal, I need a target. I’m not somebody who can, who just sort of has the self discipline to like, I hate to say this, but it’s like, they’re sort of learning for the sake of learning. And that’s all well and good. And I admire the people who can do it, I’m not one of them. I need a project or a purpose or a thing. And then I bring all the resources to bear and I’ll read really widely, and I’ll find out everything I can about the late 1990s Internet and Pay Pal and Elon his life. But if I don’t have a target, if I’m just doing it for fun, like I you know, there are other ways I certainly did my time.

James Taylor 52:26
Now we although we’ve been people as a technology company, and we haven’t really spoken too much about technology, I guess, but what technology do you use to either kind of free up your time for your creative work? Or maybe to augment the work you do as a writer?

Jimmy Soni 52:44
Yeah, yeah, man, it’s a it’s a great question. I’m pretty low tech in the sense that, you know, I use sort of the basic tools. And I’m not sitting here with like a quill in a thing of ink, right? Like I have a laptop and a phone. But I actually, for the work I do, which is the book work, which is like long form nonfiction, you have to be really careful that you don’t let technology become a distraction. And so I actually make it a point to kind of not go tech to tech heavy button for the sake of like, let’s leave people with something that they can use. All my interviews, I transcribed to a really, really good AI transcription service called And otter is great, because if you’re paying for a human person to do transcriptions, it can the cost can really add up. They’ve built this really, really elegant and very seamless technology. And I’m not like I don’t work with them or anything is just, I’m a fan. They were it was so helpful to have that during my interviews because I could look at the text and see what it it read like not just see what it sounded like, which is really powerful. One of my my kind of favorite tools is just like Google Docs has so much magic in it that goes under explored and under utilized. Like they have this voice typing feature in Google Docs that is scary, accurate. And I owe them so much. Like it’s really like they’ve saved my bacon on multiple occasions of this voice typing thing because it eliminates writer’s block. If I can just talk into a microphone and see the words appear on the screen, and then I have a bad first draft to start with. And then I’ll offer one more, which is when I wanted to reach out to people who worked at PayPal, one of the best services I use was this company called Rocket reach. Rocket reach is really good and again, you know, you have to be careful when you’re sending out cold emails but I was there with a purpose I wanted to find out what this you know what employee 37 thought about their time and PayPal. Rocket reach was enormously helpful in finding email addresses to contact people so those are the three but but honestly otherwise, I I actually try to like keep technology at bay a little bit. I’m not, you know, I’m not jumping into Metaverse writing

James Taylor 54:52
because I was gonna say ya know people mentioned Ryan Holiday earlier. You know, he has this kind of note system or his you know his cards. We If that’s how, because there was obviously so much research you’re having to do on this, I was thinking, How are you, you know, getting a handle as a using Evernote? Or is it what are you using to corral all this stuff? And on the research even before you start writing? Yeah,

Jimmy Soni 55:14
so that’s actually the latter another piece of technology, not technology. But it’s a good piece of software called Scrivener. Scrivener for long form projects, like novels, or screenplays or nonfiction books. It really is amazing. It’s like someone took Microsoft Word and told it to go to the gym for like a year. And Microsoft Word came out and it was all like beefy, you know, it has all these tools and functions that you didn’t know you needed until you start using it. And then right away, you’re like, oh, this makes so much sense for just compat compiling, and like you said, corralling the research and corralling all this material. It makes it super easy. And I recommend it to people who are doing book-length projects. Because you sort of don’t know you need it. And then the moment you start using it, you can’t imagine your life without it. Yeah.

James Taylor 55:59
So how are you moving between Scrivener and Google Docs is Google Docs where you actually sit down to start writing? And you’re just using? collating everything. And yes, how you’re using those?

Jimmy Soni 56:09
That’s exactly right. So I when I’m gathering string, when I’m just like mining raw material, it’s all happening in Scrivener. And it’s all organized there in a relatively disciplined way. I write the chapters and piece material together in Google Docs, there’s a couple of reasons. One is you can kind of do it anywhere, right? Meaning if you have your phone, or if you have your laptop, you have no excuse not to be working. The other thing is like, I mean, I don’t know if anybody grew up in like the blue screen of death era of computing. But if you did, you’re always paranoid that something’s gonna collapse. I feel like an entire generation of people that live with the blue screen of death are probably like cloud services power users, just because we were so traumatized by being like mid document and having to give you a blow up on us. And so I ended up using Google Docs, I’m totally afraid that like, I’m not going to press Ctrl S and save right. And so I ended up using Google Docs that way. The other thing that Google Docs does for me with books is I use Google Sheets like which is their, their spreadsheet software. And I kind of can track like, if you went back to my Google sheets on Pay Pal. This is even before I sent it to the publisher, there were eight separate versions, V one, two, all the way through V eight. And I can have links to all of them in Google Sheets, and they were all linked to Google Docs. And so it meant that I was never like, futzing around trying to get back and forth from Scrivener to this to that. I just had sort of two windowpanes, open whatever chapter I was working on that day, and the Google Sheets organized, crazy master control system. And that was that helped me keep everything in square. And it also meant that if I ever felt like something I wrote in a previous version was better. I can go back to it in a heartbeat and not have to worry like not have to have this like panicky like oh my God, where is it? Which version is it? That helps me deal with version control?

James Taylor 57:48
Fantastic. Well, these are some great tips for any writers, aspiring or professional writers out there as well. The founders is out now, where’s the best place for people to go? We’re going to put a link to book two and get a copy of that. But where’s the best place for people to go to learn more about you and your other writing your other books?

Jimmy Soni 58:07
Yeah, my website is just I’m also on Twitter. I’m at Jimmy a Sony. I’m admittedly like not the most active Twitter user, but I do use the DMS and I check those pretty regularly, especially right now. And then if you want to reach out to me just through email, it’s just hello, And I would love to hear from people I like I like corresponding with readers. We always teach me new things. I’m the mother of one of the people I wrote about just reached out to me 24 hours ago and basically made my week and so I love hearing from readers.

James Taylor 58:40
Well, Jimmy, thank you so much for coming on this super creativity podcast. I wish you all the best with this book and future books.

Jimmy Soni 58:46
Well, James, thank you so much for having me. And thank you so much for doing this.

James Taylor 58:49
You can subscribe to the super creativity podcast on Spotify, Apple Podcasts or wherever you get your podcast while you’re there. Leave us a review. I would really really appreciate it. I’m James Taylor. I knew been listening to the super creativity podcast.

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