I had Larry and Sergey of Google present to our partnership when there were 25 employees. So at the very beginning and we failed to lay chase. So they presented left and we didn't try and close that deal and two of the best venture capitalists in the world, John Doerr and Mike Moritz, ended up doing that deal. And I can remember at the time there were a couple of nos in our mental models. Biggest mistake of my career.
Welcome to the Carrie Newhoff Leadership Podcast. Hey, I am so excited to bring you something a little bit different today. You know, while we're focused on helping leaders in the church space, that's people who work at churches, volunteer, sit on boards, invest, that kind of thing. Today, I'm going to talk to Bill Gurley. He is the man behind Uber, Snapchat, Twitter, what else? OpenTable, Zillow. What did he do? Well, he invested in these companies when they were very, very early stage. And my goodness, this is a fascinating conversation. We talk about why you, if you're thinking about what you should do with your life, shouldn't chase your passion. You got to chase something else instead. The delusional factor every outlier needs. I find that fascinating. Right? If you're a church planter or you want to reinvent a church, are you delusional? Maybe you need to be. And how to actually find your dream job. So, welcome to the podcast. Really glad you joined us. I want this to be a very good investment of basically 90 minutes for this one. It could have gone much longer. Bill is just fascinating. He is a general partner at Benchmark, a leading venture capital firm in Silicon Valley. Over his investment career, he has invested in and served on the board of such companies as Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow. For more than two decades, he's written about technology and other subjects on his very popular blog, Above the Crowd, and on his social media accounts, he's very active on X. And now, I think you're going to enjoy this conversation as much as I do. My conversation with Bill Gurley. Well, Bill, I've appreciated your work as an outsider for a while now. I think I first heard about you on Tim Ferriss's show years ago, and so I'm really delighted to have this conversation with you. We're going to talk career, going to talk AI, going to talk about everything. Welcome.
Thanks for having me on.
By the way, I think that's such a great word, Carrie. Craft. Like if you think of fields and industries and careers where you look at someone and you say, 'Oh, that guy's an engineer. That guy's an accountant.' But you don't consider what they're doing a craft. But I guarantee you, whoever is best at it in that field, they approach it that way. They think of it that way. And I think it's another great test of whether this is something that really is your dream job and what you should be doing with your life is if you think of it as a craft, almost as an artisan. I need to figure out how to be the best I can possibly be at this thing I'm going to go do. And the other thing I think the word craft elicits is a bit of respect. Respect for the art. And one of the things that I harp on is you should really study the history of whatever it is you're going to go do. And one of the reasons that means so much to me is, one, I think it's a test. If studying the history of the field is rote and boring to you, then I don't know if you appreciate the craft enough, really. But two, it gives you such great walk-around credentials to have the knowledge of the elders in your brain. And both from the content's valuable to have, like it's really good to know the bedrock, but also when you interact with other people and they realize that you have that knowledge, it's very differentiating as to who you are.
Exactly. That you have the potential to be a master at what you do.
You know, we have a great little scene in the book I'll hit on real quick where they're having a world chess tournament and they take a break and do a history trivia quiz and Magnus Carlsen wins the trivia contest. Who's the best chess player of all time? And just the fact that he won that is not surprising to me. He mastered the craft.
Yeah. You know, Bill, I don't know whether you have this or not, and I don't think this was explicitly in the book, but like when you're describing the craft, I'm not a brain scientist, but like when I'm really enjoying this conversation, I had high hopes for this conversation, you're telling me things I wasn't expecting. I feel like when I have a conversation like this, and you know, I want to get better and better at the art of interviewing. I really do. But when an interview is going well, there are moments where it feels like all the dopamine receptors in my brain light up. I just got off the third draft of my new book, which comes out later this year. You've been through book writing. And I mean, book writing is hard, but it reaches a point at which it almost, it's not writing itself, but it's like I don't know how to describe it. It's just like you're in that flow state. You're in that flow state and you're just doing whatever athletes do. And you also have an athletic background. I have in writing, I have in podcasting, I have in this work. Is that some kind of clue for young leaders listening? It's like when do you get in flow state? When are you like you lose track of time? It's like how has three hours gone by? I was studying restaurants. I was reading the history of... I was doing this.
Yeah. I mean, obviously there's a book titled Flow and there's other people that have worked on that particular idea quite a bit. But yes, I think that when you are doing the thing that you love, you enter the flow state quite frequently. And when I say learning for free, I think that's synonymous with what you're talking about because it doesn't seem like drudgery. You lose track of time. It is giving you dopamine just to learn about the field or to think about the field or to study the field. And if you're fortunate enough to find that place, I think you become this kind of superpower. You become this athlete in that field that would be very hard to compete with. You know, some people like to give the career speech, I think they're just being provocative, but there's some very famous people that give this pitch: 'Don't do what you love. Do what you're really good at.' And there's two problems with that. But one of them gets to this point. If I'm in a field where I'm just good at it and the human next to me is good at it and has this adoration for constant learning in the field, they're going to outrun you. Like they're just going to outrun you. And if they get flow while they're doing it and you don't, they're gonna outrun you. And so that's the danger of that approach, I think. Angela Duckworth, who wrote the famous book Grit, did a podcast like 10 years after she wrote it. So she argued in Grit you need perseverance and passion. And in this podcast, she said, 'I probably shouldn't have done it 50/50. I should have put more on passion than perseverance.' And her belief now is that we've taught, especially in some prep schools and whatnot, we've taught these young adults to grind, like just to grind obsessively. And they get good at it. But if they don't have this love with the topic that they're working on, that eventually becomes burnout. Like they just eventually wear out. And so, yeah, if you're getting into flow, you're getting free energy from doing this thing. And it really is just an unlock. It's like such a powerful unlock.
Danny went out and found some mentors in Europe, you said, through some family connections. That's an FAQ on this podcast and in the work I do with leaders because we have a lot of young leaders. And it's like, how do I find a mentor? How do I find a mentor? You know, if I'm getting into venture capital, how do I get an hour with Bill Gurley? Like, please explain that to me. What are your thoughts on finding mentors and how does that work?
Yeah, we have a chapter in the book on mentors and I divide it into two halves. And you know, when Danny first sat down and said, 'Okay, I'm going to go do this,' he made a list of what I call aspirational mentors. So, he didn't beg them. Like one of them was Wolfgang Puck. There's a, in the book I think we list all of them, but like there were 10 people that were at the top of the restaurant industry. Some of them were changing the restaurant industry, so it wasn't just the most historic, but they were 10 that were important. And he made a little poster of them. He studied each of them. He wrote notes on each of them. And I think one thing that one mistake people make about mentors is they immediately think, 'Oh, I'm supposed to cold call the best and the brightest in the world.' And there's like, we go from being like bottom of the totem pole to Wolfgang Puck. You can't do that. And I love this notion of aspirational because you can learn from all those people and you can study them and it'll be very helpful to you. And very likely if you're winning, you're going to meet one of them one day and it's going to be awesome and you're going to know all about them and your ability to interact with them at that point in time is going to be so advantaged by the fact that you had studied them this whole time. But anyway, aspirational mentors are people you study. In today's world with podcasts and YouTube and AI, you can study these people like 10 to 100 times easier than it would have been 20 years ago. So, it's just unbelievable access to make that work for you. So, that's the first half. The second half for real in-person mentors, I think just don't get greedy. Like, there are people that are two levels down from the top who no one's asking to be a mentor that knows a lot more than you do if you're on the bottom rung. And so I think it's important to find people that are going to have the time to take it seriously that can still help you. And by the way, you can get multiple mentors on different vectors of whatever it is you're trying to learn about. So you don't need this holistic person where you'd end up wasting a bunch of their time. You can get someone that's good at X and someone that's good at Y and someone that's good at Z. But be more realistic as you start to climb this ladder from the bottom rung and pick someone that's a couple of rungs above you rather than, unfortunately, and once again I think it's well-intended, most when most people talk about mentors the word is so heavy it implies this guru that's basically inaccessible so that doesn't really work.
Yeah. If you were to do, and I could not agree more with that advice. I mean, some of the guests on this podcast have been aspirational mentors for me, but I didn't start with them 11 years ago. You build up a reputation, you build up an audience, you get to know people, you get introductions, you cold call some people. And sometimes it works and sometimes it doesn't. But I think you hit on something that's really different now. You can DM an aspirational mentor. I mean, theoretically, somebody could DM you. Email addresses, despite all the privacy attempts, are widely available on the internet. You can take some logical guesses and drop a cold call email. What advice do you have for young leaders on that? Like, don't jump up three levels, but let's say you had a chance to legit, you've done the hard work, you have a chance. I want to be in investing. I get a chance to pitch Bill Gurley on a coffee or whatever. What are some dos and don'ts?
Well, you combine two things there. So, I would say first on the DM thing, like I've put more time, not really money, more investment of my own time into Twitter versus or X versus the others. But it is so amazing once your network starts to grow, the number of people you might want to talk to that you see they follow you and now you can DM. It's like this unbelievable unlock and it's really powerful. And this digital, this ability to connect digitally is another element of speed of learning and mentorship that's available today that wasn't available 20 or 25 years ago. But you have to be in it to do it and you have to understand the edge to get a benefit from it. But I think it's unbelievable. There's people sharing their best information possible. They're doing it out in this public space. And if you happen to say something they like or they read something you wrote and like it or follow you, now all of a sudden you've opened a communication channel. It's crazy. So anyway, I think you want to be rolling around in these tools. Like it is the modern toolkit and it's very easy to dismiss whatever comes up next. You know, I'm guilty of being better at Twitter than I am Instagram because you know I'm older and that's the one that I got to know and TikTok I'm even less. So it happens. But anyway, I think you need to roll around in it. In terms of approaching someone, I think it's really valuable to know as much about them as possible because it's respectful and that can land in a very powerful way. Two, I think you want to ask for something that's very concrete and finite. Like I don't think you want to ask for, 'Hey, will you be my mentor for all of eternity?' I think on your first attempt, you should be asking for a very specific piece of advice like a particular problem that you've done or a piece of work that you've created that you want them to opine on. But it needs to be something where the ask looks like it's a maybe 5 to 10 minute investment from the other side just for the first one. Because if you propose something that's going to look like it's infinite time or unknowable amount of time, it's going to be very hard for that person to opt in just because they couldn't do it across the number of inbounds that they're getting. And then the other thing I would say is if you happen to be aware of a particular interest or even better a new interest of the mentor, that's an area where you might be able to bring something to the table. So, I mean, I don't want to talk too much about social media, but let's say you were really great at TikTok. And that mentor's not exploiting that channel, and you had an idea. You could as part of engaging saying, 'By the way, two or three of your peers are crushing it on TikTok. I think I know why. I could probably write up an analysis for you or maybe I wrote it up. I've attached it in case you're interested. I think you might really benefit from this.' Like if there's an opportunity to do something like that, now you're bringing something to the table.
See, in both of those, I love your answer because in both cases, it assumes that you're adding value, not just asking. Like it's true on social media, it's been surprising how many of the people I know today that I only admired from afar discovered me because like you, I started blogging in the early days of blogging and they would read my stuff and go, 'This is really good.' And then occasionally they would reach out. That's how my best friend who used to work at one of the biggest churches in the country got to know me 15 years ago. You know, he discovered me. Some other people who become very good friends discovered it. But I was adding to the world, not just asking. And I think that's really important for people to hear. Similarly, in the cold call, what great advice, like specific, measurable, short, do your homework, like you know, 'Hey, I read your book and you cover this and you cover that. But one question that hit me was blah blah blah.' And then just be grateful for whatever you get.
And maybe add some value in a new area. Okay, that's super helpful. And I would be the 10,000th person to say this, not the first, but you got to let the no or the no response just roll off your back. You can't let that build up any kind of anxiety. Like, it's fine. Maybe they didn't see it, maybe they didn't read it. Maybe they're not the type of person that likes to give back. It's fine. Like, let it go. Like, no big deal.
The other thing you talk about is peer-to-peer mentoring. And I'm not a sports guy like you are, so I'm sure to our listeners they would get a lot more out of the names you drop in that section of the book. But you talk about I think it ends up being seven friends who eventually became college ADs for football, I think it was.
I think that model is perfect for church leaders, right? Because everybody knows somebody else, right? When we talked about it early on, I said I wanted to circle back to this. Yes. So, is this it? Yeah, I think this is the, so it's probably the book has six principles interlaced with a bunch of profiles of people that once again started on the bottom rung and most of them became the very top of their field. But one of the principles, probably my favorite, is titled 'Embrace Your Peers.' And I think it's a concept, you know, mentorship is a concept that's been widely discussed and widely recommended. This one I think is less intuitive, but there are examples of people that built peer networks. And when I say the word peer, I'm talking about someone who is on the exact same journey or climb that you're on. That's not two rungs above. They're on the same ladder rung you're on and you're both trying to get to the same place. And the thing that's great about if you can find multiple people like that is you get shared learning. So it's not just you that's learning, you're learning what they're learning. Now it requires that you be super comfortable with sharing what you're learning with them. And one of the reasons why I think this particular approach hasn't been recommended as much is a lot of people, especially people that want to be successful, are overly competitive and they're what I would call sharp-elbowed. And the notion of giving your best ideas to someone that's climbing in the same mountain you are feels anti-intuitive to them and even feels like a bad idea. But I don't think there's, this great book about finite and infinite games. We build a lot of our mental models from studying finite games like sports events and whatnot or board games and there's one winner, they end and there's a winner and that's it. But infinite games, which life is, there's not just one winner. And most of these fields there's a large number of winners. And so you got to get this out of your head that I'm competing with every single human that's in this field because that's a very lonely journey. And if you can, and the example you mentioned when we started talking about this in the book, we have a chapter about these seven young people who are working at the very bottom rungs of their athletic departments. They're all executives in the athletic administration at colleges and they meet at a conference and they start texting each other and sharing ideas and when they leave the conference they go back to each of their respective schools but they now have this text group. So oddly, they all end up top number, you know, athletic directors at seven of the top schools in the country. And when we sat down and talked to them all, like this co-learning thing was a huge part of why they were all so successful. And it got more and more sophisticated each year. And like in the latter years, they were doing two or three day meetings. They're bringing their wives. They're inviting special guests to come speak on topics they don't know about. Like, and then they take that away. And I say it's odd they were all that successful when you get in the weeds and see what was happening and that co-learning. It's actually not odd. It's actually intuitive that's what happened. But it's very, I don't think it's intuitive to go do this. I think most people, 'Hey, go start sharing with this other person that you might be competing with' is not something that's logical to do.
Yeah. You know, it's almost like they started an impromptu DIY mastermind, right? Just with that text group and then annual gatherings and then they sort of became three-day events. And I think that is such low-hanging fruit that most people miss. And you brought up in the ministry. I mean, unless your houses of worship are right next to each other, you're not competing really with these other people. We're all on the same team. If you can find, we're supposed to be peers in other cities that are on the exact same journey you're on and get into this area where you're sharing different things you try. You probably try something new every, you know, once a week, right? And some of it works, some of it doesn't. And if that can be eight people sharing that experimentation, there's another story in the book in that peer chapter that's far away from ministries or athletic directors, which is Jimmy Donaldson, who is a young 17-year-old kid who loves YouTube, like he just loves YouTube, flat out loves it, and starts playing around with how to basically be successful on YouTube. And meets three other people. They do a daily Skype call for like 16 hours a day and Jimmy Donaldson becomes Mr. Beast, you know, who is the most successful YouTuber on the planet. And you know, at the time when he started doing that, his mother wanted him to go to college. He was not particularly interested in it. He was wildly interested in this. And he says after the fact, referencing the Malcolm Gladwell book 10,000 Hours, he said, 'The hell with 10,000 hours, we're getting 40,000 hours.' Because there were four of us learning at the same time. And they were learning how to master this new craft of being good at putting videos on YouTube. And he also said if a fifth person had been on that call, they would have made a million dollars. Like the techniques they were uncovering were so new and so powerful that if you mastered them at that point in time you got immediate financial reward out of it.
Yeah, there was only one Mr. Beast out of that group but everybody else, I think you said they grew their followers to like a million followers. They all did well financially. It didn't all do as good as him. But the point being, you know, it's very similar to the athletic director story but this I think in the ministry this is a huge opportunity. Like if you can, especially if you can find people who enjoy the same type of worship and same type of congregation that you are and you can find other people like that in other parts of the country and everyone's experimenting with techniques and social media and other ways of growing audience and congregation, I bet it'd be super valuable.
Yeah, that's what I found 20 years ago in the what is now the Irresistible Church Network. It was just like-minded leaders. We're trying to build that out. We are building that out in the Art of Leadership Academy. One of the things, Bill, that you've had experience with, you've hinted at it, right? They're not all Open Tables, they're not all Ubers, they're not all Zillows. You lose some bets, too. Yeah. In venture capital and Jimmy Donaldson, I mean, his story is fairly well documented now. I mean, he spent years posting videos that got zero views, three views, failure, and his mother had every right to say, 'Listen, you're disastrous at this. Please go to school.' I would like, it seems to me like we've moved into an era where people almost want the success more than they want that curiosity. It's like I just want you to show me like, you know, with all of the leaders you met, what is the tension between loving the craft as we've identified it versus no, I just want to succeed. I want the hacks. And then what is the long-term prognosis for each mindset?
I think that unfortunately, the combination of very well-intentioned parents and very well-intentioned counselors and advisors to young adults have gotten to a place where they're very concerned about the economic stability of this person passing from being a teenager to a young adult to an adult. And they very much want them to chase a traditional job that just feels safe. And you know, we sit here now where many of those safe jobs are under threat from AI. But if you go back before AI, you know, there's a 2023 Gallup poll and only 23% of Americans say they're engaged and thriving at work and the rest are not. And so you don't have a situation where a lot of people feel like these people we're talking about that are in flow that want to study all the time. A lot of people aren't in those places. And I think at least part of it is we've become quite overstructured in how we turn children into young adults and teenagers into young adults. And different people have talked about it. Jonathan Haidt in Coddling of the American Mind called it the resume arms race. And we all know we're guilty of it. We all know it feels a little odd when you're pushing the six-year-old to basically resume pad for their college application process with cello lessons and volunteering at the, I don't know where, but like it's all performant. It's not, you know, they're doing it for the sake of doing it. And the kids' time is just way more used up. Rick Rubin in his book said, you know, as children, few of us are taught to understand and prioritize our feelings. For the most part, the educational system doesn't ask us to access our sensitivity, but to be obedient, to do what's expected. Our independent spirit is tamed. Free thought is constrained. So it's, and on top of that, like the colleges, if you go back 20 or 30 years, they wouldn't let you pick your major to the end of your sophomore year. At many schools now you have to apply to a major as part of the application process. And so you're once again, you're just being forced into a tighter and tighter, narrower and narrower path that doesn't really allow you the freedom to go find this type of curiosity thing that I think is important to find. And so, one thing I would really encourage, whether it's parents or counselors, if you happen to see a spark that might be, you know, like Danny is with restaurants, like fan that flame. Like, do anything you can to help that individual feel like that's possible. And as a parent myself, I know it's hard. Like if you think this particular individual could go be a McKinsey consultant, you know, they'll do very well financially. But if they really are passionate about being a basketball coach, that's okay, too. You know, like if they're really passionate about it, they're going to have a way more fulfilling life doing that and they're going to fill up with energy. They're going to be in that flow state all the time. And the other thing I've told some young kids who are very purpose-driven, almost every single person we cover in the book that ends up thriving in their business, and Danny's a great example, ends up touching so many lives. Like they end up having so much positive impact on the world because they redefine their industry and then they share back into that world. And if you met someone that worked for Danny, anybody that's ever worked at one of Danny's restaurants, it's like one of the highlights of their resume. They talk about it for the rest of their life. Like it's a piece of walk-around collateral that you were involved in this big tent that Danny created over time. And so anyway, I think that's really, as I mentioned with the Jerry Seinfeld story and the book he read, like I hope that we can give as many people as possible permission to go live this life of flow, as you say, because they're in the right place. And the book, I want the book to speak to the young people who are making the decision on what they're going to go do with their life, but I also want the book to be helpful as a guide to the people that are around that young person and giving them advice on how you should maybe approach that situation when it comes up in the future. And I think if you teach yourself to be more open-minded and encouraging, you're going to find, I got this great email from a parent that had watched the video that I mentioned, the early version of this book, and their child was at a reputable college in finance, I believe, and came home one day and said, you know, I'm really spending all my spare time in this other thing. And it wasn't as certain as finance or anything like that. But the parent told me about their journey from acceptance to embracing to encouraging. And as the parent went through those stages, the relationship between the parent and the child blossomed. And the confidence, the parent said the confidence of the child went up dramatically as well and hopefully they'll go thrive in that new industry. But it was such a heartwarming email to get.
Now, we have a software engineer and an accountant as our two sons, and we've had that conversation. You know, they're both in their 30s now, but they're like, 'We felt that pressure to get that career.' And I'm like, 'Yeah, guilty as charged.' And so it will continue to lead to some interesting conversations.
One data point that was uncovered by Dave Evans in the great book Designing Your Life. If you look at the stats, like four or five years out of college, 40% of people are no longer in the career that their major was. And when you get to 10 years, that number drops even further. And so it's important I think for people to know that because we've put so much weight on this college journey and this degree that you maybe have created this belief that you have to stay in that lane. Like, oh, I've invested all this time, like why would I ever consider leaving? And I think just helping young adults understand that people do move around. And by the way, some of the people that move around, David Epstein in his book Range, like some of the people that move around are the ones that have the biggest impact on a field. Like they come into it late, they studied something else and they bring new ideas. And so it's perfectly fine. I think that's another lesson that's important for people to understand. It's perfectly fine to repot yourself, to move around, to try something new. And the one caveat I would give on that which I think is important is don't overspend early in your life. Like don't spend right up to, because then you're stuck. Then you don't have the flexibility.
