So, Bill, thank you so much for being here. And I have to say when I first heard about the book and heard that you were writing a book, I was excited about it for the reasons that I talked about. But I went back and watched the UT Austin presentation and I thought I'm even more excited about it now. Then when I read the book, I was just amazed like how many years between then and now. And it feels like it must have been pretty much a full-time job during that time writing this book.
It was about six years or yeah, the project. So the history of the thing is I was at a point in my career I was reading some biographies. I read these three and noticed these through lines and it was when I was blogging actively and I wrote down notes just as I would for any one of my blog posts but it wasn't really related to the venture world and I got invited to do this speech at the MBA program at McCombs and I said to the dean can I use this he said sure and so then that went on YouTube and people started seeing it both people whose life had impacted but also James Clear saw it as an example, the author of Atomic Habits, and he started talking about it. And then I was at this strange event that Chris Saka actually had put on where he invites a bunch of random people that don't know each other. And this one guy, he just kept prodding. It wasn't just me. He prodded everyone. He said, 'What have you done that's creative?' Like just literally pushing pushing. And finally I said, 'Well, I have this presentation.' And like that night he went and watched it and he says, 'You have to write a book.' And he just wouldn't get out of my head. And so he probably deserves the most credit for pushing me to go do this. And then the other side project or the other side thing to know is over the years I became kind of a huge fanboy of well done high-quality non-fiction writing for reasons I can't explain just like a hobby and through that got to know Gladwell and Lewis and some of and studied their work there's a book called the new new journalism. So once I decided to do this creative thing, I took it very seriously and so the structure of the book's fairly unique intentionally. The storytelling in the narratives of the profiles was intentional, right? Like there's a lot of intentionality that went into it.
And you did you also got a co-author or co-writer?
And did you think when you took on this undertaking that it was going to take as much time and as much commitment?
No. No. So partly my co-writer, so the co-writer there was this article that I encourage everyone to read called the greatest bowling story ever that I had read it was in D magazine in Dallas in like I forget what year 2008 and I had read it and like I told you I was a fanboy of non-fiction right so I had read this thing and I reported it to everyone and one day I met this guy. I said, 'You're the guy that wrote that.' And he said, 'You're the guy that gave that speech at Texas.' Like those were the first two things we said. And then it turned out that the way I wanted the profiles to read, he does a ton of work for the Atlantic, like many Atlantic articles, each one of them, maybe a full Atlantic article. So anyway, that's how that happened. But we ended up chatting a lot on Zoom and not getting and the project kind of expanded got bigger and bigger and you kept on putting more and more resources into it. I mean you talk about the career regret survey that you did and then so we started to wonder like how many people might have missed out on what they should have been doing with their life. And we did a SurveyMonkey survey and asked you know if you could start your career over again you know how many of would you want to do over and 70% of the college people said they would want to start over and then we did it again and expanded it and then we did it with Wharton just to like really solidify to make it official. And along the way we also went and read everything we possibly could in the industry and all the work of all the famous authors in the industry. And Daniel Pink had written this book on regrets, the power of regrets. And he had studied regrets across multiple countries, different cultures. And the number one thing people regret at the end of their lives is what he calls boldness regrets. They're regrets of inaction. So people humans are remarkably good at forgiving themselves for mistakes they make. Ah, I learned something, you know. No big deal. Moved on. But the thing that you can't get out of your brain is that thing you always told yourself you were supposed to do that you didn't do.
Sounds a little bit like the concept of loss aversion in behavioral economics, right?
Yeah. Absolutely. Very similar. But he even has graphs. You could probably find them. But like it gets worse. Like as you get older, this regret of inaction like takes up more of your brain space. And when you looked at career regret, talk about conveyor belt careers and how like today we think about how wired people are from the time. I'm fairly convinced and I didn't dwell on this in the book, but I'm fairly convinced that the modern path from say sixth grade through college graduation has evolved in a way that's non-helpful for people stumbling upon, you know, what they're fascinated by. And I'm not the only one that's talked about that. Jonathan Haidt talked about that. He has a chapter in The Coddling of the American Mind called the resume arms race. And we it's so hard to get into college. We start thinking about that as parents when you're in the sixth grade and you know lacrosse lessons and cello lessons and Mandarin lessons and volunteer work and like the activity calendar of a young adult or a child these days is so overscheduled compared to when we grew up, right? You know, and you're just out roaming around.
When we grew up, it was like, 'Get out of the house. I'm locking the door. You're not coming home till 6.' And my mom today, if a mother sent their kid out of the house and locked the door, you'd have CPS showing up at our house.
Well, and well, yeah. And there's some really interesting work once again that Haidt talked about where we were overprotective of their physical life and less know about their online life, right? Which is a different problem, which is terrifying. Unrelated to this. Yeah. But yeah, I so I think we've forced kids into this meat grinder and you start learning to perform. Angela Duckworth was asked recently like she said if I could rewrite her book over again, she said it was 50% passion and 50% perseverance. And she said she'd probably weighted way more on the passion side because she's met all these kids and she teaches at Wharton. She said we met all these kids who have learned to grind. So they've learned how to just get in there and roll through academic work. But if it doesn't come with any innate fascination, I did a TED talk recently which will be out June 8th. But I talk about the fact that like when you're fascinated with something, the learning is free like you study things for fun. Like you get done reading it, you go ah you want to tell somebody you're excited. You get energy. When you study things you don't want to be studying, they sap energy. You get tired. You're like, 'Oh, I need a break.' You know, I got to get up and take a break. And that contrast is massive. Because if you can get your career aligned with something that you're fascinated with, you're going to have this massive unfair advantage where the continuous learning is just going to be effortless. It might even give you excitement.
And parents aren't they're not ill-meaning. I mean, they have your best interest at heart. They want you to have a successful child.
And I don't it's not just parents. It's parents, advisors, teachers, counselors. I've even talked as I've been promoting the book. I often sit down with career counselors at these universities. And I'll tell you a very funny story because we're going to get into some of these topics. But I was explaining to this one, where was I? I was at University of Chicago, I think. And I explained to her what the book was about. It was right before it had come out and she says, 'It's an odd thing for a college counselor to say,' she goes, 'But that'll work for some fields, but not like what about like, you know, English poetry. How could that work for them?' And I'm like, 'Well, you're the one giving them a degree. I don't know why you're pushing back.' But I and then I opened the book and I showed her these two examples. One is a guy who fell in love with the Grand Canyon and turned it into a career and another was a guy who fell in love with Texas horticulture and turned it into a career. They're both profiled in the book. And I showed it to her and I said, 'Well, these are I don't know how much different they are than English poetry.' She goes, 'But I bet those two people worked really hard.' I'm like, 'Yes, yes, yes, that is a requirement.'
Yeah. It's one of the things that struck me throughout the book, and to your point, when you're doing something you love, the hard work actually doesn't feel like hard work and you can do it. You can grind for 10 years, but then you're going to lose steam at some point. But there is no substitute for grinding, for actually working really hard.
And in the TED talk, this isn't in the book, but I also realized the other unfair thing that happens when you're fascinated by something is everyone notices. So when you talk about it, you get excited, you know, and you're studying the nuance of the field and the edge of the field. And so when you're talking about it and you're talking, oh, and I just found out this and I just found out, people like, boy, that kid really cares about that subject matter. And then when opportunities come your way because someone say, 'Oh, you're interested in, you know, Spanish architecture.' Joey, that's like all he's ever studied. And then you start introducing people that direction like job opportunities, everything comes at you because you're known as this person with this massive fascination. And so it just gets easier. Everything just gets easier.
So let me ask you a question. And I was thinking in the dedication to the book, you dedicated to your wife, but you have children and your children are now sort of college, post college, right? Did you write it partially for them? Because I'm sure as a father you were giving them advice.
They wouldn't want me to answer that question. I think you know actually I'm going to see one of my sons later tonight and he asked me to bring him 10 copies for his students. He's a So, this is interesting. I mean, because this relates to the subject of the book and the TED talk. He's a Mechy from Carnegie Mellon. He interned at Logitech and Tesla, but after that second summer, he came to his mother and I said he wanted to be a school teacher.
And so he entered Teach for America. He's teaching nearby.
And he was TAing and he said he got two compliments one day. One for being a good TA and teaching and one for being a good engineer. And he said one felt 10 times better than the other. That's awesome. So that's really good. My second child, so my first is a sophomore, my second is a freshman. The freshman is a business degree, which every white boy in America gets a business degree. That's just the way it goes. But he is the last person in the world to be, you know, to go into business. And I tell him all the time, you know, I think you'd really like to be a teacher. I think you should really think about that because it's just his personality. But I would say because in the epilogue is my story and I did two different careers before I got into venture.
So I was that that was my next question.
Yeah. So but so I'll pause on that point. For young people, I would say it's perfectly fine to not know to not have this. Like I don't know what percentage of people at age 18 know exactly what they're fascinated by. And the entire chapter titled Chase Your Curiosity has tons of different exercises, many borrowed from some of the best in this field on how to kind of wander around and learn and experiment with other things. And I think it's perfectly fine to not know. And I think it's highly useful to know whatever you're doing is not it, right? So you can keep moving.
So, so let's go through your career because you did make several three different changes. CS at University of Florida and you end up at Compaq, which you know, Compaq in 1989 was tech in 1989 was a fraction of the size tech is in the global economy today. But it's probably not understating the case that Compaq in 1989 was the Anthropic of today.
It was hot. So, you were hired by the hot company.
Yeah. And you stayed there for a while and said the hot thing isn't for me. Yeah. I was and I want to be careful about how I present this because I think it's very specific to me. As a practicing engineer, we started the third computer project. Back then, you know, PCs were known for the Intel processor inside of them. So there'd be a new Intel processor, you'd have a new PC. Anyway, the third one looked a lot like the second and looked a lot like the first. And I was like, man, I don't know that like I want to do 20 of these, right? Because it's going to, you know, get a little mundane. And I asked myself, do I see myself doing this 30 years from now? And I think it's a good test in retrospect I don't think that's in the book, but that is like in retrospect that's what I was doing. And I could go see and meet and talk to people that were in their late 50s that had been an engineer their whole life and with no judgment against it may have been quite fulfilling for them, but like I could say, is this what I want to be? And I got to a no. It also turns out that at night at home I had stumbled on this book, One Up on Wall Street by Peter Lynch. I had opened a Prodigy account. I was trading stocks, you know, at home at night, right? Well, you can't trade at night, but I was researching stocks at home and so I think there are clues in your hobbies, you know, there clues in what you choose to do with your spare time.
Well, and as an undergrad, and this is one of the great things for, you know, you're a year or two out of undergrad, the easy thing to do then is to go to graduate school and make a complete pivot on your career.
Right. And that's what I did.
Yes. And I had been reading the trade rags because I was in the business and I could see that there was software, there was other parts of the stack. I was interested. I had fallen in love with Borland's Turbo products back then and was coding with them and they went public while I was working there and I bought the stock. So business was fascinating to me. So I got an MBA and I attacked business school in a proactive manner like what am I going to get out of this? Like I'm paying for it. Like I'm choosing to do this. They owe me and I was going to suck spending a lot of money for it. I'm going to suck as much information out of as possible which is not how I attacked undergrad.
And what you talk in the book about how you in graduate school you all of a sudden started to become a reader. Like how does that happen?
I don't know. Can I put that in my kids? I don't know what happened. I had not been much of a reader at all up until that point in time and I had read One Up on Wall Street and I had read a couple other things like that, but when I got to business school, it just flipped. I don't know. I don't know if that's ever happened to anyone else.
So then and you can tell the story, but you go to then the you know.
I toyed with the idea of venture. I mean if you think about it, I did you know what a venture capitalist was? Well, I did a little bit, but yes, I mean, Doerr was on the board of Compaq, believe it or not.
And my sister had started there four years earlier and had options. And so, I kind of like started to understand this game a little bit, right? And I met with a couple I did like the coffee. Oh, can I get a coffee? And they told me like, go work for 20 years. I'm like, well, that's not very helpful. And anyway, I'll try and speed it up. So, but along the same time, because I was interested in tech and business, I was reading Fortune and Forbes and the journal, and there was this team at Goldman Sachs of Southside analysts, Dan Benton and Rick Sherlin. They were just quoted all the time. And I was like, that's pretty cool. They're like studying the industry and people view them as experts. So I went to New York and knocked on doors and begged for that job.
And amazingly so you get that job.
And then through like sheer force of will and a little bit of luck you become the tech analyst.
And by the way in getting that job there's a concept in the book I have that called make yourself a candidate of one. I think the best jobs for like you to really thrive are ones where you go and create the opportunity yourself. Like not I think like the odds that you're going to thrive in a job where you waited until someone had a wreck and or the worst for me possible in my brain. This was part of why I wrote the book is the college like job interview through the career office where you're like lined up like 20 people 15 minutes each like how are you going to differentiate yourself in that you know type of situation and what are the odds that your dream company and your dream career is happens to be interviewing at your school like it's near zero right near zero it's less than 5% unless you intentionally went to some school like in anyway. So I think you can create a make yourself a candidate of one and I think almost nearly everyone that breaks into venture does that because there just aren't there no bulletin boards for venture jobs.
Well and I'm sure you get asked this question all the time. I get asked the question all the time, you know, how can I get a job in venture? And my answer I'm curious. Do you have a pat answer? I have a pat answer, but what's do you have?
So I 15 years ago wrote a four-page PDF letter to answer that question and I would just send it to people when they asked. And in the near the last 25% I'd say, if you want my help, do these 15 things and then come back to me. And like only two people ever came back through. But when I was doing one of these in Boston at MIT, I was having this conversation. I said, you know, a bunch of kids kept asking me for the letter afterwards. So I posted it. So I posted it on my Twitter account like five weeks ago. The whole letter.
I'm going to go read that.
I don't think you need to.
Well, I mean I don't need to, but but I will.
To take you back anyway. So then I get this job as a sell-side analyst. And it's fabulous. It's so fascinating. You get, you're 28, 29, and you get to meet with CEOs and CFOs. I ended up covering Compaq on Wall Street and Dell and met Michael and like it was such a blast. But yet again, three years in, one night, I remember like it was yesterday, you know, in Wall Street when you're that age, you're working. I'd get to work at 7, 6:30 and I'd leave at 10, you know, and I'm on our floor, Park Avenue Plaza, 36th floor, and we had the whole floor and the four corner offices were the most senior analyst. And I went and did a lap and I stopped in front of each of those offices and I said, 'Is this who I want to be 30 years from now?' And by the time I was done with that loop, I knew it wasn't this wasn't it. Despite how much fun I had and how much access I had. And so I didn't quit the next day. Oh, I'm out of here. I started planning for the next move.
So when you one question for you about sort of taking the leap or taking this jump, a lot of times people are terrified like they're going to they don't have the flexibility. I can't because I have this or I have that. You know, I tell young people like minimize your obligations early on because it maximizes your chances to take risks.
Um, but I totally agree with that. And I was fortunate. I kind of grew up with parents that taught me to be frugal. And so I never I never got out of I worked with tons of young people on Wall Street that immediately got the house in the Hamptons and like the membership club and they were stuck like right away when I nervous about bonuses, you know, like I never had to worry about. When I first got onto the startup side, the first company I was CEO of, one of my board members was talking about hiring a VP of sales. And he said, 'One of the things with salespeople is you hire them, they spend all the money that they make because that's what sales people do. So you want to make sure that they're driven by their commissions.' Yes. So it's the in that case, I understand. Yeah, I've got the big car payment, the everything else.
