What if AI isn’t the threat – but the greatest ReInvention Accelerator of your lifetime?
In this episode, we sit down with Bill Gurley (legendary Benchmark partner; early investor in Uber, Zillow, Grubhub) to talk about his new book Runnin’ Down a Dream and the principles behind building a career you actually want.
Bill breaks down why so many people feel stuck on the “college-to-safe-job conveyor belt,” and why mid-career can be the best time to make a change – if you approach it with the right mindset. We dig into the difference between low agency (AI feels terrifying) and high agency (AI becomes jet fuel), and Bill shares a practical framework for exploring your next chapter without blowing up your life overnight.
In this conversation, we cover:
- Why career regret is so common, and how to reverse it
- Bill’s “Never Too Late” philosophy for mid-career reinvention
- How to build a “dream job folder” and test your next path before you leap
- The smartest way to use mentors, peers, and aspirational models
- Bill’s blunt advice on AI: you can’t stop it, so learn to wield it
If you’re navigating burnout, uncertainty, or the feeling that your work isn’t you anymore, this episode is a permission slip + a playbook. If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you – people designing what’s next.
**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.
Episode Transcript
Bill: There’s this massive irony about AI. If you’re high agency and you are deterministic about what you want to go do, there’s never been a better time and these tools are jet fuel and can help you get where you want to go faster.
Chris: All right, Todd, what do we got going on today? What are we talking about for our reinventors?
Todd: Well, Chris, we’ve got somebody pretty amazing and inspiring on the line today. Bill Gurley is a legendary venture capitalist and general partner at Benchmark Capital. Known for his early investments in companies like Uber, GrubHub, and Zillow. And like most really successful people, Bill is continuously reinventing himself and just published his first book called Runnin’ Down a Dream, an incredibly timely and relevant book for the moment we’re living and 1000% aligned with our mission of helping mid-career professionals reinvent their work and plan wisely for the future. So I’m so excited for this conversation and this book, and we’re gonna cover a wide range of topics, including Bill’s specific advice. For how to think about making a successful career change. And we’re also gonna pick Bill’s brain on what he thinks about the future in general with AI and all the changes that we’re seeing. Just a really good benefit of having a visionary on the line. But before we jump into all this great stuff, Bill, we just wanna give you a warm, heartfelt welcome to our show.
Bill: Thank you. I really appreciate you having me on, and I agree I think the alignment is fantastic and I look forward to getting into it.
Todd: Yeah, thanks so much, Bill. And I gotta say that reading your book, there were a few statistics that really jumped out at me. More than 70% of people say they’re living with career regret. Nearly six in 10 say they would choose a different path if they could start over, and only about 23% of people worldwide say they’re truly engaged at work. Okay. So I felt your book offered a really practical path out of this. And I love the matter in which you express the wisdom via stories of people like Mr. Beast and Bob Dylan and legendary New York restaurateur, Danny Meyer, who I know is a good friend of yours and many of your other uber successful friends, and it really feels like you reversed engineered how to be successful in rapidly changing world. So I’d like to start by understanding what prompted you to write this book and give this gift to the world.
Bill: Very early in my career, I started writing. I started writing and sharing externally, and there are other people that do that, not to put myself in their class, but like Howard Marks and Buffett and Bezos with his annual letter. There are just certain people that like to think out loud, and I, I think you get a lot of benefits from it. I think you learn better. I, I don’t wanna go down that path too much, but I made that decision and so part of what I was known for was my blog post on Above the Crowd. And I got into a habit when I had a new idea or a new thought that popped in my mind of just jotting down notes in a folder and maybe appending to it over time and letting that either develop or not, whatever happened naturally. I was at a point in my career, I was reading biographies the three biographies I read that really clicked in this way for me was Bob Dylan, Bobby Knight and Danny Meyer. And when I finished the third one, I was like, holy shit, There’s things that they each did and they both started on the very bottom rung. Or all three, and they all three went into fields that your parents would tell you to stay way, way far, far away from. And I just loved the idea that it was possible to start on the bottom rung with massive intentionality.
So as you mentioned, the book’s divided into two halves. We have profiles which are stories of success, and principles, which are tools of success. And through a lot of work with a great co-writer and a wonderful editor, we all came to the idea of alternating them, which I adore. It makes the book different. But, anyway, I saw that through line and it just clicked in my brain the way figuring out a new industry or a new technology kind of clicks. And I’d write a blog post. So it was the same methodology I developed, but for something that was kind of outside of what I did day to day. And then one day someone invited me to speak at the University of Texas and I said, can I do this thing? And they said, sure. And I made a presentation, that got posted to YouTube. A few people noticed, most notably James Clear, maybe the bestselling nonfiction author of all time. And eventually people told me, you gotta put this in a book.
And when I got to the point in my career where I was hanging up my boots and freeing up some time, it gave me the attention I needed to do this the way I wanted to do it. And so me and the co-writer spent five years, reading a hundred more biographies, talking to academics in the field, talking to Duckworth and Adam Grant, Daniel Pink, and like all these people that, really defined the category.
Despite the fact that it was a side hustle passion project, once I got into it. I really devoted myself to it. I hope you could tell that the work had that amount of attention when you read it. And that’s the story .
Chris: I mean, bill, it’s a fantastic book. And listen, I still wanna read the book that is your memoir of your career. I think that’s a cool book to read, but I appreciate that you wrote this one first. I think you follow your own principle, always give back. I think you’ve given a gift of permission to the world and I think there’s millions of people who are gonna read this and be encouraged to live better lives.
Bill: By the way, I left one thing out that relates to what you just said. Someone handed me Arthur Brooks’ book Strength to Strength, which is about what do you do when you’re 55 and kind of done with the first career. That’s what it’s literally about the book’s about that and it has a lot of that same message you just mentioned and part of that triggered in me, this is the thing I should go do. The world doesn’t need a book about how to be a better VC. It doesn’t touch that many people.
Chris: Right. No, and, and I think it’s beautiful. It’s a very big picture, encouraging book, inspiring book with those great stories. I mean, it’s a page turner too, and it’s also very practical, right? It gives a some real clear guidance to people. I mean, one thing I think about as a father, right? So I a hundred percent embrace the message that you have, and this is the message of reinvention that Todd and I have as well. Follow your genuine curiosity. Follow your passion and figure it out. And as a parent, I think, Hey, I’m gonna support my kids, even if, as you say, we don’t really know how that’s gonna make money, but that is a factor, right?
I still want ’em to make money. Right. that’s a question I have is how do we balance that? Because a lot of the people in this book, we look back and I could say, well, is there a survivorship bias? Like, did we know they were gonna make or was it about the commitment that brought ’em there? Like how do you think about that axis?
Bill: Well, I mean, you put a lot into a lot of questions. The first thing I would say is, you know, you talk about how do you balance it? Well, I think the world hasn’t been balancing it. The world’s been a hundred percent focused on using this thing I call the College conveyor belt.
It’s almost like an industrial complex that’s been created, to push people towards the safe jobs. I mean, I’d, say two quick things in response to that. One, I think every parent’s intuition, and I have three children of my own, is more tilted to the safe and the money than they realize.
it’s not like they’re making a mistake. It’s the maternal and paternal instinct to want them to be okay that causes you to do it. And I, I think in the back of your mind, you kind of know, oh, well maybe you should do this instead, or. And I have this wonderful letter from someone I know who watched the original presentation and their son, is like a junior in college finance major, and every spare moment of his time he was spending on basketball, and not playing basketball, the art and science and studying of how you win. If you read the Sam Hinkie chapter, that kind of stuff.
And the father told me that the father went through a progression of awareness acceptance, through these stages. And finally got to support and enthusiasm for what the child wanted to do. And he said their relationship blossomed. And the kids’ confidence went up tremendously, and now they’re going that direction.
And, I would bet on ’em being successful, because what I heard from the father was just, the obsession was so high, you know? And I think that’s a can’t lose, position to be in. So anyway, we’ve tilted this other way. And I think getting to balance is just reading the book and thinking maybe with a little bit of both minds simultaneously because we’ve been so far against this other rail.
You know, you mentioned the statistics I have in the book. I think part of that’s a result of this situation. You know, Jonathan Haidt, he calls it the resume arms race, by the time you’re in sixth grade, parents are worried about your college application. They’re telling you to do cello lessons and go volunteer at the uh local food bank and like, the kids they’re running a hundred miles an hour. They’re being taught to grind, but they’re not being taught to explore. And there’s minds like Jonathan, Rick Rubin has a paragraph in his book that kids just don’t get to explore enough. For me, I love word that you use the word balanced. ’cause I think we’re wildly imbalanced right now the other way. And once people have this idea in their brain that they maybe could be more supportive, you know, I have a, I discovered this wonderful anecdote after I wrote the book, so it’s not in the book, but, in McConaughey’s book, Greenlights, he comes to this moment at the University of Texas where he wants to abandon the law track he was on and go to film school and him and his father had discussed him being a lawyer for 12 years. And his father bragged about it to the other. Members of the community. And so there was a lot of weight on this promise. And he had massive anxiety about calling his father took a week or two, finally called him, you know, set up this call.
He says, dad, I think I want to go to film school. And his dad said, well, don’t half ass it. And McConaughey says the last thing he expected and the best thing his father could have possibly said. And it gave him not only permission, but responsibility and all this other stuff. And I, I just love that notion if more of us, I hope the book does that for a lot of people.
But if more of us as parents and advisors could have the, of heartfelt insight to do what his dad did right there, you know, it’s not easy. It’s not easy to do that.
Todd: A nd lemme ask you a question because as you know, like our big focus is helping folks that are mid-career, who are dealing with burnout or transitions, or AI and all these things start to shift over and start to embody some of these principles in your book, which is a different set of circumstances, ’cause these people have, you know, 20, 30 years of trajectory. You talk a lot about getting mentors and finding models. Right, and also surrounding yourself with peer groups. Like these are all great examples of how to explore a career reinvention, things that we talk about in our community, like really powerful stuff. But we found that there’s some inertia for people that are like 20 years into a certain career path they’re one of those statistics that we talked about in the beginning of the book. Right. And now they’re sitting here coming to a podcast like ours, thinking, all right, what do I do? How do I make this shift? And it’s hard because there’s some humility involved in that. There’s some kind of deep personal growth, like, oh my God, I’m now 45 and I have to rethink my life and my career.
Bill: There could be financial constraints too.
Todd: Oh, a lot of financial concerns. So I’m curious, How do you apply your principles to these folks? Particularly if you want to take the lens of looking for mentors and peer groups. ’cause all of a sudden people are like, what? You want me to go on LinkedIn and like reach out to somebody for an informational interview? Right, like so what what do you say to those folks?
Bill: Before I get into it, a couple of notes for the listeners. One, I’m not gonna reveal any of it, but there’s a chapter called Never Too Late in the book, dedicated to this topic. So I’ll let them discover that, here’s what I would say, if you have high agency and determinism. There’s never been a better time to do whatever you want. There’s this massive irony about AI. If you’re low agency and you’ve been through that industrial complex and you arrived at a job with a hundred other people that look just like you, AI looks scary as all get out. But if you’re high agency and you want to go your own direction and blaze your own trail and learn you know, at whatever speed you wanna learn at, there’s never been a better time in the history of the planet to do that. Finding peers, finding mentors, learning, all those things are way, way, way easier today than they ever were. Because of the online world and AI and all the great technology. So first of all, like there’s no excuse. But I’m gonna give you a little more detail and this isn’t necessarily in the book, but there’s a great book I read long time ago by Harvey McKay called Sharkproof, and Harvey’s known for his sales book, but he wrote this one book about careers, and he said put a dream job folder In your file cabinet. Now, this book was 30 years old, so manila folders and file cabinets had a place, that’s probably a digital file today. You know, it might be a Google doc or a Notion or whatever, but just start thinking about it and start building the details of it before you ever leave the job that you’re in because you have these constraints and you’re locked down. But build, almost a model of what it’s gonna be like. And I would start in the mentor principle, I talk about aspirational mentors. Danny Meyer did this, pick 10 people that are doing this thing you think you want to go do and build profiles of ’em. like literally, you know, a Word doc or a Google doc for each one of them.
And put their name and a photo and you know, study how they did it. If they wrote a biography, read it. If they’ve been on YouTube doing interviews, watch ’em. If they’ve been on podcasts, listen to ’em. And then you can sit there and. Pay the $200 for the better version of Chat GPT and almost talk to them. Like you can just put what would so and so say if I ask ’em these questions? And like, you can study them and, and it’s such a useful exercise. And, if doing that is tedious or boring, that’s not the place you should jump towards. Like, this should be fun and exciting to do that exercise I just described.
and then as you do that and you study all of them, you’ll start to think about what might my next step be? Who might I reach out to? How would I go about this? Like it starts to feel more real the more you put yourself in that place. And I don’t mean physically, I mean mentally put yourself in that place, you know, in your free time. Spend your free time doing that. One, you’ll test whether this is something you really have the passion and curiosity for that you should have if you’re gonna take this leap. But two, I think you’ll fill in some of those pieces. You’ll answer those questions for yourself.
Todd: Mm-hmm.
Chris: I think you’re answering such a big question for people because you have. Six principles. We have six tenets in our community. One of the most difficult ones is the clarity in the beginning, getting clarity about what direction am I going? And what we say is we say, take action, run smart experiments. And I think you’re saying something very similar to that. And for people who are midlife and their mid-career and they’ve got this job and they’re thinking, well, where am I gonna fit that into the day? Bill I think what you’re getting at is something that I like hustle culture gets wrong. Which is, it doesn’t require as much discipline so to speak, when it’s love, when you are pulled to it.
Bill: absolutely correct. a, there’s a book many people have read called Flow. And if you love what you’re pursuing, time passes before you know it. Like you never are sitting there going, oh my God, when do I get off? Like, when does this stop? It never happens. It just doesn’t happen. I talk about in the this should be something that you would choose to do instead of watching the Netflix episode that you’ve got queued up. Like it needs to compete with that in order to qualify for something you should definitely, if you’re mid-career and about to. stop doing what you’re doing. It should qualify at that level. It should be that exciting to you.
Chris: Bill, if you knew the amount of technical hoops I jumped through to make sure I could be on this call with you today. ’cause I love what I do so much. If this had been my corporate job 10 years ago, I would’ve been like, Internet’s broken. I can’t make it sorry. So I I totally agree.
Bill: I wanted to get back to your, uh, survivorship bias thing. You know, one thing that gives me quiet confidence about that question is I’ve already heard from so many people who saw the original video and started doing these things and got to a better place. So instead of top down from the winner I’m hearing from the people that are on the journey. I got a great letter from this guy, Dan Casey, who’s got quite a social media following. He saw the original video. He, um, loved football. He coached Pop Warner in his free time. And after he saw that video told himself, you know, one day I’m gonna spend my time with football and not what I do every day. And it took him seven years, but you can find him on social media. he has a website for how to think about offensive play calling. He has an app software application that you can use. He’s well known in the football media world. Like they follow him and talk to him. And he is, he is on cloud nine, he’s, that he’s doing this thing that was a hobby and I’m fairly certain most hobbies can be turned into careers.
Todd: This is exactly what we talk about, getting clarity, and you said it in the beginning of the book. That, that’s actually the hardest part is actually finding that fascination. And you made some Recommendations of other books, which I love that you did that because it’s like, spend time getting clarity, spend time getting that vision because that’s what’s gonna drive everything else.
Bill: One thing that I think is super important, especially for younger people, and this this this gets at, the issue that some of your listeners run into. It’s okay to change careers. It’s just okay. Like, and many people do. If you get 10 years post-college, over 50% of people are no longer in a job related to their major. And I think it’s like, uh sunk cost aversion We spent so much time, K through 12, four years in college, maybe a master’s. And you’re like, I can’t leave this. I’ve invested in it. but that’s, not what people do. You’re putting that mental block on yourself, you know did that sunk cost? Like you’ve seen in the book, I use this phrase, life is a use it or lose it proposition. Like, you gonna keep doing that till you die just because you’ve had those previous investments. it doesn’t matter. Like you need to optimize the many years you have left on this planet. And that’s all that should matter, not what, not what you did in the past.
Todd: I say that all the time on this podcast. You know, This life is a blip in the Matrix, and that’s why I love this book because it’s a wake up call to say, yes, that is true. So what can I do? And you mentioned another phrase that you use at Benchmark, and I’m gonna quote you. Good judgment comes from experience, which comes from bad judgment.
I’m curious what you mean by this, and given what we’ve been talking about today, like how does this apply to, let’s say, a mid-career professional that’s looking to reinvent their career and listening to this conversation? What does
Bill: Yeah, I mean, I, the saying is what it means, like, especially in venture, like you make a ton of mistakes. And part of the message is don’t get hung up on the mistakes. That’s the pathway towards wisdom. Like you’re, you’re making your way there. The corollary to that, which is super important around mentors and peers, If you can hear about that mistake from someone else that created the experience and not have to live through it yourself, that’s really intelligent. So learn as much as you can from others so that you don’t have to learn the hard way, even though learning the hard way is actually more indelible in your brain.
Chris: I think the venture capital lens is really interesting, right? Because if we look at it like, I know that I was held back for so long by this idea that I always had to get everything right. You know I’ve said to Todd a bunch of times in this podcast, biggest mistake I ever made was getting good grades as a kid because everybody put me on that conveyor belt. And I think venture capital is one of those things where you can look at it and say you only have to get a certain fraction of bets, right? You don’t have to get a lot Right. But you gotta get the ones that you get right. You get ’em really right.
Bill: You gotta recognize that a failure is a big part of it and not get overwhelmed by that part either, and learn to live with that’s not easy, but yes, you are exactly right.
Chris: I think the resilience factor here, and especially for our mid-career professionals who are looking to reinvent, I think there’s a pressure that we might feel to say, Hey, I’m 45, I’m 50, whatever it is, I gotta get this right. That’s not the right energy. I think it’s a little counterintuitive where you have to have hold it loosely and experiment a bit.
And Bill you said you went through a few phases yourself. And what we tell our people is you actually tap into your experience. It’s not like you’re reinventing anew, and I think that is something that you did in your career too, right?
Bill: Yeah, I twice, I started two careers that I actually loved. Maybe likes the better I did well. and enjoyed them and I think they were stepping stones for where I ended up. I think they helped build to there. But in both cases I got two or three years in and asked myself this question, which is, do I see myself doing this 30 years from now?
I even walked around the office and thought about the people that were lifetime in that career. ’cause there were some already there. And I could. See what that meant and said, is this what I want with my life? and it’s not a judgment on them. It was a question for me way into the future.
And that mental process caused me to say, no, I need to move in a different direction. It’s a similar version of this thing Jeff Bezos calls the regret minimization framework, but he says when he was thinking about starting Amazon, you know, he had a very successful career at D.E. Shaw and David Shaw wanted him to stay and he told himself. When I’m 80, what advice would I give myself about this decision I’m about to make, which also echoes Stephen Covey’s Begin With the End in Mind. And I think those kind of exercises are really valuable for your listeners just for a gut check about is this what I want it to be forever? You know, and if not, what are you gonna do about it?
Chris: Todd, are we ready to invite Bill to be a coach in our community? ’cause he speaks our language man singing our song,
Todd: Bill just so you’re, you’re aware and so we have a community, so we have a peer group of of midlife professionals that are reinventing. Right. It’s, it’s very in line with what you talk about. And the first thing we have them do is what we call the clarity course, which is basically the practice of writing your own eulogy, which, you know, Stephen Covey talks about that i’ve been coaching people for years to do that, to just get imaginative for a minute and to stop the wheels turning and just, what could happen, right? If my life and my work worked out to the most idealistic way. Like without any limitations, and I’ve found it to be just an uber practical thing to do right?
So, yes, like we’re totally in line. I also wanna ask you, ’cause you mentioned before, AI and you obviously look, we have you on the line. You’re a visionary. You’ve been in technology. There’s also this element of being tactical as we’re looking at the future of work in our careers, and I know you have a very optimistic view of AI.
I’ve interviewed Bill Burnett, know, from Stanford in designing your life, and he also is optimistic, and we read your article in Financial Times about it, and I agree a hundred percent with your sentiment that there’s loads of opportunity. But I’m curious, what are you seeing from your vantage point in terms of how much of a shakeup, what industries are gonna shift? Like how should we hold this as mid-career professionals? The fact that the world is changing really, really fast right now and AI is coming
Bill: Before I talk about who I think is most at risk, I want to make a few points about, dislocation and technology. So one, it’s been happening forever. The word Luddite is about something that happened in Europe with looms and how it threatened seamstresses. Go read that Wikipedia entry on that, like, just to get in touch with how long this has been going on. And 98% of Americans used to be in the agricultural business, and it’s less than 2% today. That that may not help you, come to terms with what might be happening to you. But, it’s one of these things that’s outside of your control. You know, that was another Covey thing, like what’s inside of your circle of influence and what’s outside. You’re not gonna stop AI. Like even if you’re mad and you join a, a user group or you call your congressman, you’re not gonna stop it. So sitting around in pity party worried about this thing or, or even if you could talk to government into fixing it, what are the odds that that actually works? You think some government retraining program’s gonna save millions of people’s lives?
I think there’s zero chance that would be successful. So recognizing that it’s outside your control. What, what can you do? Well, there’s a lot of anthropologists that have highlighted we evolve with our tools. You know, the farmer with the tractor is way more productive than the farmer without one.
And so the best thing you can do is learn how to use the tools as well as you possibly can, and whatever industry you’re in, if you know the edge of what’s possible with AI in your industry, you will be valuable in that industry. You’ll be the type of person they want to promote to the top of the ladder to figure out how the organization’s gonna evolve going forward. And so, perhaps counterintuitive, but you wanna run right at it. There’s, there’s this story I love, I think it was Björn Borg retired early and he tried to make a comeback and while he was retired, they switched from wooden rackets to these big headed graphite rackets. And he tried to make his comeback with the wooden racket and he just got smoked. You know it may be idyllic or whatever, but this is part of why. I’m a heavy, heavy believer in continuous learning and I don’t think enough people think about it in their career, but learning about AI and how to use it is a requirement right now. This is a big tech dislocation. You need to understand it. And if you don’t, it might run you over and hit you over the head and there’s nothing I can do I or say to stop that from being a reality.
Chris: I love the way you frame that though Bill, because this is something that’s happened a thousand times over. You talked about the Luddites. People thought the printing press was going to be like the end of society, right? it’s happened many times and yeah, this feels like a singularity and this is a very big impact .
Bill: And it’s different, it’s hitting some white collar jobs really fast paralegals. I’ve talked to people that run large law firms that have drastically reduced their paralegal footprint. And so it’s real. I don’t want anyone to say, oh, he’s in denial. And like, I’m not, it’s real.
It’s different than what’s come before. Mainly ’cause it’s hitting white collar first and fast and that causes a lot of anxiety. But I stand by what I said and maybe for your audience, if it hit you hard, maybe it’s an opportunity for you to jump in an entirely different direction.
Maybe you could be thankful that it’s giving you the, the push you need to go do something different. But said earlier in the podcast. If you’re high agency and you are deterministic about what you want to go do, there’s never been a better time and these tools are jet fuel and can help you get where you want to go faster.
They’re enablers but yet those first things have to be true. You have to have this obsession that makes practice feel free and then these tools will help you in ways you can’t possibly imagine. There’s a famous Austonian that’s in the Never Too Late chapter, Bert Beveridge. Who created Tito’s at the age of 40. It’s such a great story,
But he has a phrase he gives other founders and entrepreneurs around Austin where he says, you have to find a way to turn hardships into motivation. I guess he’s a master of it, but like if you can, tell yourself now I’m gonna go win, and and turn it into fuel. It’s a superpower. I think it’s hard to do, like, I don’t wanna say that’s hard to do, but he’s a big promoter of that ideal.
Todd: I’m gonna ask you about one of the tools that you talk about a lot, which I’ve heard before. This notion of giving back. No matter where you’re at in the process is something that you argue will propel your reinvention, propel your success, like open you up. And it feels counterintuitive because especially for our audience, the people that are in this stressful stage of reinvention, and it’s like, it’s a lot about me.
What do I do? I have financial worries. I have worries about what my next stages are. It feels very insular and throughout your book, and it’s not just a giving back. There is also this amazing quote that you said around how like the top Nobel laureates, have these other interests. They have these hobbies of dancing, of doing magic. Like you know that there’s something about having some level of lightness and other interest and also giving back. Can you speak to this, because I think this is counterintuitive to a lot of the people that are trying so hard to pound a square peg through a round hole, but you’re arguing that there’s actually other ways to go about life that will create more success.
Bill: Let me start with the first one. So there was something I think I really connected with in the Bobby Knight book where, he aggressively pursued mentors in a way that, you’ll read about it in my book, but I think it’ll make you wanna read his biography. It’s kind of an unprecedented level of mentor pursuit, like showing up at conferences, one thing he discovers is these people are willing to share with him. They don’t treat their information as some proprietary advantage that can’t find. So much so that he ends up as a player in a head-to-head game where the other coach had shared a bunch of stuff with his coach and they ended up winning. And he’s like, should I reflect on that as that person made a mistake. Or do I internalize it as there’s this give to get kind of concept. The more I give, it’s gonna come back to me in spades. And, he talks about it in his book over and over again. One thing you realize, if you study Bobby Knight, and you know, at this point he’s kind of gone down in history for some of the outbursts and that part of his persona, but he probably has the richest coaching tree in the history of the sport. The number of people that worked under him or played under him that have gone on to coach in the league is nothing short of, of just jaw dropping inspiring.
And if you’re holding onto everything, if you view everything as proprietary. If someone that works for you wants to go explore on their own or try and cut out on their own and you get mad and call ’em unloyal, that’s a different type of overly competitive mindset that I think leads towards unhappiness at the end of life. And what I’ve seen from these great people is they just don’t get caught up in it that way.
They get excited for people that move on. They get excited for people that win on their own, even if it means competing with ’em one day. Like the benefits worked, whatever the cost may be. And so one of the things I try and teach people to do is adopt that mindset right out of the gate. If anyone asks you for advice, take the time because you want everyone to give you advice. There’s karma in the universe. I, I do believe it. And you will also develop a reputation that will take you a very, very long way if you are that type of person. And take the time, write the think you note, send the gift. Whenever you achieve anything, think of 10 people that helped you get there and send them a little note. It will pay back in spades and you’ll feel better about yourself and you’ll develop the right mental mindset for really long term success. From my point of view.
Chris: It’s an interesting notion because like Todd was saying, coming from a perspective of people who maybe are thinking insular and inwardly focused, but also just in the scheme of capitalism, we talk about this now. Like that’s a pretty radical notion in a way, right?
The collaborative element, and I think it’s great to hear from a very successful venture capitalists around this, that the way to success does not have to be zero sum. We can lift all boats together. I think that’s pretty amazing.
Bill: I’m a big fan of this tiny booklet called Finite and Infinite Games, and. I was looking to see if I had it around, the concept I can just share. You don’t have to go read the book. Most games are finite. There’s zero sum, there’s a winner and a loser. There’s a beginning and an end to the game, and unfortunately, many of our strategies are built from studying finite games. And it turns out that life is an infinite game it’s not a finite game. And there’s many winners. Like in downhill skiing, maybe there’s one winner in, Business and a lot, like a lot of industries, a lot of career. There’s tons of winners.
To think in this proprietary sharp elbowed way, you’re gonna make your job so much harder to climb all the way up the ladder than if you think in a collaborative way. And I will one kind of secret about Silicon Valley, it’s wired that way.
It, I can’t tell you why, but when you are young and you go to Silicon Valley and you start asking people for their spare time and advice, they say yes, a lot.
There’s something in the water. It may just be that so many people move around between so many companies and so many jobs, and there’s so many people that are trying to learn, and so many people that had asked for advice before, I don’t know exactly why, but it’s a bit magical.
It’s a really wonderful part of Silicon Valley, maybe my favorite aspect of Silicon Valley is that that is true. And I saw a documentary on Netflix on songwriters in Nashville. Not the artists themselves, but the songwriters that write the songs, and it sounded exactly the same. Some kid moves there and says, I wanna be a songwriter. And someone who’s got four songs that have been a Grammy says, oh, I’ll help. Like I can’t even explain why, but even just telling that story gives me a smile and happiness. I love the notion of that. I love that that’s possible. There’s something wonderful about it.
Todd: Yeah, it’s like kismet. There’s just something energetic about it that we’re all human, we’re all in this together. And as we’re coming to a close of this interview, ’cause Bill, I mean, I’ll be honest, we could talk to you for like three more hours and just pick your brain on every word in the book. I hope you can feel how resonant this is for us and how excited we are for you and your book and we hope that this goes out far and wide. And I just wanna end on that note this notion of like create a culture of rooting for other people you know of rooting for everyone in your life to be successful. Our whole thing is this reinvention community where we’re building a peer group of reinventors that are mid-career, and what we’re trying to get across is, yeah, let’s root for each other. Let’s figure out ways that we can support one another in this world that is changing. And there is stress and anxiety, as you mentioned. And so, I want everyone to read this book. I want people that are parents to read this book so that way, they can wire in their kids with some of these mindsets very early and tools very early on. And also for people that are in our stage of career reinventors, mid-career, really important to start that rewiring of your mind and thinking process so that way you can really find that success and that fulfillment and that joy faster. ’cause that’s what I feel at the core of this Bill is like a kindness. I said in the beginning, there’s a gift to the world that you’re giving by doing this book, and I really felt that, and I feel it now. And I just wanna just send you some appreciation, brother, and we’ll do everything that we can to get this out far and wide
Bill: I mean, I said at the beginning, Bill, you really embody that principle of always give back with this, and just for people who are listening. This book is a great book. It’s really inspirational. It really is a fun book to read. The stories are great. I love the conceit you have where we don’t know who the story’s about until we get into it, and I think that’s really cool.
Chris: It made it a real fun mystery to solve. I solved one or two, but uh, it’s pretty great. And, and it, real, real page turner really enjoyed it and really I think it’s a life changer. I think it’s gonna become a sacred text of reinvention for our community for sure.
Bill: A lot of what you just mentioned was very intentional. Like I studied some of the best nonfiction writers of all time. I spent six years on the book, so, I’m thrilled to hear that came out that way. Thank you guys.
Todd: Thank you.
