How to find a peer group that lifts you up with Bill Gurley

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2:36There's a lot of focus on mentorship in careers. It sometimes feels like there's this mystical quality around mentors, like a mentor will solve everything. If I could just have a mentor, it will unlock all these doors. Most of the people who have been super important in my career are two-way reciprocal relationships. Honestly, most of them look more like friends than they look like mentors. The most important work relationships often don't come from where you think they will. Mine have always come from a real foundation. They've been people I've worked with or people who just knew me from life.

3:13They were my customers. I was their customers. I met them in an interview. they showed up in my life in a real tangible way, and then we built a friendship. These relationships have been such a powerful force in my life. Every job I've gotten, every hard decision I've had to make, someone has been there for me and helped me figure out the way forward. I've turned to these people and they've helped me move forward, even though they're not that mystical mentor figure, they're mostly my peers. I believe in this so much that it's basically everything I do now. I want to connect with people, but much more importantly, I like connecting people to each other.

3:53From the glue club to the guild, the communities that I build, even to this podcast, I believe that the most powerful force in your career is finding people who have walked in your shoes, that you can build authentic vulnerable relationships with. And I think those relationships can power your dreams. Today's guest shares that belief that peers are one of the most powerful forces behind successful people. And he also thinks that we don't talk about it enough. So today we're going to talk about it. I'm Molly Graham, and this is Work Life, the show where we untangle the messy human side of work.

4:31Bill Gurley is one of the most influential venture capitalists of the last few decades. He spent over 20 years at Benchmark, a famous investment firm in the tech industry, where he and his partners help back companies like Uber, Nextdoor, Zillow, and OpenTable. Bill wrote a book called Running Down a Dream about how people build careers that they actually love. And one of the ideas he kept coming back to is the power of peers. Bill credits peer groups as one of the keys to his own professional success and thinks that it's often overlooked. So we're going to talk to him about how peers have shaped his career and how you can find a peer group that can lift you up.

5:13I just want to start by saying, Bill, that I kind of hate the word mentor. And it's one of those words that I just feel like maybe has kind of lost all meaning. And I mean, you've become kind of vocal recently about the idea that peers matter more than mentors in shaping careers. So I'm curious, what's a peer group in Bill Gurley land, and what is it for?

5:36Bill Gurley: Look, I don't want to dismiss the value of mentors. I think they're critical, and I think the point I would make about peers is that it's a less discussed topic. Kind of to your point, mentors may be over-discussed, and I'm not aware of anything at the school level where they promote this idea, and I actually think it should be promoted in your work organization. And I've tried to do that a couple of times in the past and been surprised at some of the reluctance or resistance. But maybe I'll start with a short anecdote that I love. There's a gentleman named Jimmy Donaldson, and he's 17 years old, and he's not doing well in school, not really liking school.

6:22His mother is pushing him

6:25Bill Gurley: appropriately to go to classes at the community college and to try and pursue a post high school degree. But he's become fascinated with YouTube and it's all he wants to do. It's all he wants to talk about. And I think just as a matter of chance, not necessarily that he pre-thought this out, he got connected to three other people who were also trying to gamify or you might say reverse engineer YouTube and how it works. And it happened to be an important point in time where the platform was quite emergent. Now, Jimmy would say that they spent 15 hours a day on Skype together for four years. Now, that might be a bit of an overstatement, but still.

7:12Bill Gurley: And what they did on those calls was they shared ideas about how to make videos work, how to make them pop, what the thumbnails need to look like in order for them to get promoted. And they would all go study on their own, try experiments on their own, but share to the center. And it turned out that all four of them became quite popular. Jimmy is now Mr. Beast. I think a lot of people get caught up in thinking that they're in a competition. I think a lot of youngsters participate in sports, youth sports. They're encouraged to. And most of those are zero sum games. There's a winner and a loser and the people that aren't on my team or on the other team.

7:56And like you develop this mindset that isn't rooted in kind of giving away the goods and sharing what you know with other people.

8:04Bill Gurley: But it can be really powerful. He was telling that story on Joe Rogan, and he kind of used the meme from Malcolm Gladwell and said, you know, instead of 10 ,000 hours, we've got 40 ,000 hours because everyone shared to the middle. And I think that's a powerful way to talk about how you can gain advantage from sharing with a peer group. And so I recommend that everyone out there, regardless of where they are in their career journey, try and find three or four other people who are in the same rung of the ladder that you are, that are trying to figure out how to be successful. You know, I think outside your organization is better than inside because you get more diversity of ideas and opinions than you will if you're just inside.

8:53Bill Gurley: And meet with them and talk to them. And I think it's a real important and powerful thing to go do. And I've watched some people do it, but I would say along my career journey, it's a fraction of the people that do it. It's maybe 5%. There are certain groups that do it really well. Founders are really good at it. Most VCs tell founders to go find a CEO group, and most of them do. So that's a weird, you know, little area of the world where it's kind of common practice. Yeah. And then I find some groups that feel like they need an extra leg up or some help will form groups. I've spoken to a really cool group of women VCs that organize themselves and they do a Zoom once a month.

9:45Bill Gurley: They bring in external speakers, you know, and share ideas. It's the same thing with a black VC group. And so there are pockets of people that organize in this way, but it's not generally taught. Yeah. So I actually had a group just like this where, and it's when I first knew you when I was the CEO of Quip, I went out to breakfast with a friend of mine who was the head of operations at Pinterest at the time. And I feel like all we did in that breakfast was just stare at each other and be like, this is so crazy and such a hard job and so weird. And we had such a great breakfast that we were like, we should do this more often.

10:22And so we just started having breakfast once a month and we just started inviting people. And it ended up being like 10 to 12 sort of COO-like people, some of whom you know well, like Jay Simons, who was the president of Atlassian, was in it. And Jeff Doniker, who was the COO of Yelp, was in it. And we met once a month for five years. And we just went through everything together. And so it really resonates with me. Those folks have been so important to me in my career and my life.

10:51Bill Gurley: Yes. Will you tell me a little bit about where did this realization that peers are so important come from in your own life? First of all, I was an engineer for two and a half years at Compaq. And I had one relationship with this guy who was one of the most talented people I've ever worked with. He was super kind with his time and giving. There was another guy in the organization, and he was very sharp-elbowed. So I saw this huge contrast. And then when I got to New York, where I worked for four years at an investment bank, I met this guy, Mike Moveson, who was also a research analyst. I was covering tech.

11:33Bill Gurley: He was covering food, of all things, like food companies. You'd think we wouldn't have much to talk about. But we shared ideas on how to value companies. We shared relationships on the buy side with each other. We shared books, ideas. We're close friends today. We're both on the board of the Santa Fe Institute. And someone I have leaned on as a thought partner my entire career, you know, and it started in that first week when I landed in New York. Yeah. But it sounds like for you at the beginning anyway, it was about finding people that you felt kind of had something in common with you, or at least were like open to learning together and collect, collecting them in some ways.

12:18Bill Gurley: Here's another one that's interesting for, for whatever reason, as I entered the research business in New York, three different people at other firms in my category retired. They were young and I cold called every one of them and And they all became friends and they shared all of their work they had done up into that point in time. And I guess it's a version of it, like being very proactive at networking horizontally. Well, tell me a little bit about that. Like you took a cold call and turned it into a relationship. How did you actually do that with those folks? I think it comes down to just constantly sharing over time.

13:03Bill Gurley: And this is what you want to do with your peer group anyway. Whether it's a book that you found, an idea that you have, it can be a well-reasoned question that's thought-provoking that they appreciate you coming to them with. It can be career opportunities for them. It could be a networking relationship that you want to share. That's something that I've done my entire venture career, like proactive help on networking, even when there's nothing in it for me at the moment in time, you know, because it leaves so much goodwill and people, you know, want to pay it back. So that's something I've done forever.

13:46Bill Gurley: So, yeah, those are the kind of things that keep those relationships alive. And if they're the right kind of person, you'll see the reflection of that. You'll see the exact same things coming your way. And if they're not, then they're not the right type of people for this type of peer group. And I think there are people that are sharp elbowed, that'll take every idea and run and never share it back. I think those people exist. And I would just not invite them in your group or kick them out if you want to figure out that's how they are. Totally. Yeah, I have this thing I say, which is like life is a barter economy.

14:25Like you should do things for people without expecting things in return because you want the world to be full of people that owe you, you know? Like you want to be helpful to people and then over time it kind of like pays itself back to you and it sounds like that's sort of what you did. Always. Yeah.

14:40Bill Gurley: Always. Yeah. Always. I did that with this group that I mentioned to you, The Breakfast Club in particular, because I met this guy, Jay Simons, who you know, who was the president of Atlassian for a long time. And he was so nice to me. He taught me about SaaS. And then I was like, I want him to be my friend. I want him to be my peer. And so I invited him to the breakfast club to try to be helpful to him. And then we built this amazing friendship over now 10 or 15 years. But it's like such a powerful way to turn a relationship that could be transactional into something that's actually meaningful.

15:13Bill Gurley: Yeah. And one thing that I think important since we started the call talking about mentors, there's a vulnerability that's allowed with peers that's just not there with mentors. And there's a support that comes from peers that's just not there with mentors. And so these groups, I think, have a community benefit to you that's extremely important. There are bad days in your career journey. Since I wrote this book about how to chase your dream job, people will say, well, if I'm having a bad time at work, how do I know if maybe this isn't my dream? And if you have a group of peers that are all working at other companies, you can explain to them what's going on and get a sense of whether this is something native to that career journey or maybe something specific to your situation.

16:08Bill Gurley: And that can be super helpful. It may just mean you need to repot in a different company, not give up the career chase, right? And they can help you get that information that you wouldn't have otherwise.

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18:55Bill Gurley: I need your approval. Approved. Thanks. Oh, agents, where would we be without you? Hmm, somewhere with a lot more tabs open. Create your first Monday agent in minutes at monday.com.

19:16Out of curiosity, like, do you have some stories or a story where you used peers or a peer group to help you make a difficult decision or get unstuck?

19:28Bill Gurley: Yeah, I mean, certainly on big life decisions. I remember when I had convinced myself that being a sell-side analyst wasn't my dream job. And I got approached by Frank Quattrone, who wanted me to keep being a sell-side analyst. And I didn't quite know what to do with it. And I called Roger McNamee, who was a customer, a client of mine, who knew a lot more about the valley than I did and walked him through the whole thing. And he was very crystal clear about what I should do. And I followed his advice and it worked out extremely well. You use this phrase in your book, which you mentioned, Running Down a Dream.

20:12Amazing book. Everyone should go read it. But you use this phrase, co-climbing. Will you explain that phrase?

20:19Bill Gurley: Yeah, I just, I mean, you can go back to the Mr. Beast example. You know, he said, you know, everyone can win. In the book, there's a whole chapter on this. But these two gentlemen, early in their career, are both working in development and athletic departments, which means helping to raise money from alumni. They're a year or two in, they go to a conference, meet, start a text group, slowly invite in other people like you did with your group. And eight of them today are Division I athletic directors at the top schools in the country. And so much so that there was an article written that the NCAA is worried they have too much power in their collective block.

21:04Bill Gurley: And so that's co-climbing, right? They all started at the bottom rung. Just think of a ladder and now they're all at the top rung. And, you know, the second chapter of my book is about lifelong learning and how important it is to constantly learn as much as you can. And so when you think about that being critical, this group is super helpful. And if you are in an organization where you're dealing with new things and we both worked In the startup world, you know, those companies are taking advantage of dislocations at technology disruptions. And in that situation, the more you can learn quickly, you know, is super valuable and important.

21:48Bill Gurley: And as we sit here on this big wave of AI, sharing how you're using AI and how you're unlocking things, you can rocket ahead right now. And if you're, whatever role you're in at whatever company you're at, if you're the person that knows more about what AI can do for your firm in that role, you're super valuable, like hyper valuable. Totally. And so that's a real-time example of the type of information that can be shared across a group like that. Yeah, well, and I really loved your point about vulnerability and being able to be vulnerable with peers in a way that it's harder to be with someone that you look up to or want to think well of you.

22:29Whereas with peers, I think you could be like, I don't know how to do this. How are you doing it? Yes.

22:33Bill Gurley: The best way to get smart is to admit when you don't know stuff. So people ask like these leading questions like, well, I'm sure you know this. And then it feels really difficult to say, no, tell me. but that's the exact right thing to do. So, you know, if you want to even sound more confident, say maybe I should, where do I need to go study? Is that something I should really know about? Let me know, but don't ever pretend when you don't like just always ask, you know, always ask. Yeah. I would even say with mentors, I would take that attitude because eventually if you do that all the time, the number of times it happens going to drop because you're, you're eventually going to build the information set and the confidence you need.

23:17Yeah. So you started to talk about this idea that peers and being around, you know, a set of people can change the trajectory of your life and your career and sometimes like reframe what you even think is possible. I'm now part of, as you, it sounds like you are, I'm now part of a bunch of these and I run some communities that basically facilitate this and I see it regularly change the trajectory of people's lives. When you put two people together that you think are extraordinary, they build a relationship and it just takes them places that you can anticipate.

23:51Bill Gurley: There's a word I love, optionality. Another way to think about it is the probability of luck increases. If you read any biography, there's usually two or three things that happen to somebody along the way that seems surreal. Oh, what you happen to be there when this person was walking by and that, and the more the possibility set increases because you have these eight other people out looking out for you to a certain extent. Right. And they know what you're excited about. And when they meet other people that are excited about those same things, they connect you together. And those things don't happen if you don't have those networks.

24:36I love that. It's, I love the, I love the potential for luck goes up because we all know that luck is such a part of big, powerful careers, but it's funny. It reminds me like when I was at Google very early on, I was in the communications department and I built a bunch of friends there, right? Cause that's what you do when you're 25. Uh, and, but then I left and then everyone left and they all went on to be the heads of communications at like every single other company in the technology industry. And suddenly I had friends that were like the head of communications that like Tesla, you do it. Yeah.

25:07Tesla, Twitter, but you know, these were people where I could call them and pick up the phone. And I always say to people, like when you're leaving a company, the only things you take with you are what you learned and the people. So like, you know, just like realize that that's a huge asset, which I think is part of what you're saying. Like you build these relationships over time, and eventually they pay you back in some form or another. So I want to go back to Benchmark just for one second, because you said venture is a very sharp elbowed competitive industry, but Benchmark is very famous for having an unusual partnership structure where it's equal economics and collaborative decision-making.

25:46I want to hear just a little bit about how you think that shaped you and you think that shaped the success of the firm that you helped build. Yes.

25:56Bill Gurley: And I wasn't a founder. I came in shortly after the founding. And the founders had worked in a hierarchical firm, which many partnerships are structured that way, law firms, different types of consulting firms. And in those firms, the senior most people take the majority of the economics and your goal is to work your way up over 20, 30 years to take part in that. And the founders of Benchmark felt that the young people in a venture firm actually add a tremendous amount of value. I've come to believe that as well. And therefore, they wanted to start a firm where everyone was equal. I don't know if they really had the foresight to know all the positive things that would come out of that decision.

26:46Bill Gurley: And I'll share a couple of negatives as well, but the positives are just no one's, you know, targeting one another. Everyone's trying to help one another. And if you are successful as a VC, we're going to split that equally as if I'm successful. So there's a tremendous amount of built-in collaboration and built-in help. When you bring in a new partner, you want them to succeed radically because then you do well and they benefit from that. And so if you're in a hierarchical firm, there's a lot of if I win, you lose kind of thing. And that dynamic just completely left the room. And so it was very collaborative, very supportive.

27:32Bill Gurley: It was very easy to express vulnerability and to ask for help when you needed it because everyone was rowing in the same direction. And I feel like so wildly fortunate to have moved into something like that and takes a lot of anxiety off the table and a lot of tension out of the room.

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31:02I want to just go to some of the sort of complicated sides of peer groups. Like one of the things that came up for me, you mentioned a lot of founders in Silicon Valley have peer groups and that that's sort of a place where that has naturally been built and they can really elevate and support those founders. But I also think peer groups can like distort your thinking. Like you are so enveloped with people that think the same way as you or they just like reinforce bad thinking. Like, do you see that? Do you see sort of the adverse effects of peer groups?

31:35Bill Gurley: I do think, as I mentioned, I felt that it was more powerful to go outside of your company than inside of your company. And that's part of the reason. Like you want to identify new ways of doing things, not reinforce old habits. And I think one of the things that hinders companies from growing over the long term is they develop blinders or they develop sacred cows that they're unwilling to look around or beyond and they get stuck. But if you get a lot of super curious people and you get people from something different, you know, from where you are, I don't think that happens. I think you debate things intentionally.

32:15How do you think, I mean, you talked about sort of the idea of like kicking people out of a peer group or knowing when it's sort of an unhealthy relationship.

32:25Bill Gurley: Yeah, I mean, I'll do the obvious ones first. Like if someone, you know, takes networking relationships and takes ideas and never gives back to the center, there's an obvious one. if someone takes information that's shared in the group in a way that's where you expect you know some type of confidentiality and they're out blabbing about it on twitter like immediately after the meeting that would be a bad sign and you'll feel these things like you'll feel them naturally you'll feel is this a friend or is this someone I'm that I feel is a little bit of a snake Like these are very human things that you would notice.

33:07Bill Gurley: I'll share another thing that I've thought about a lot over time but never written about, and I don't quite know if I'll do it justice in explaining it. But I find often when people meet new people in new relationships, eventually they'll say something provocative or something that you might not expect just to see how the other person reacts and to see if they do the same thing. There's an amount of vulnerability sharing that builds a lot of trust in relationships. And if someone always shows up kind of in sales mode with this perfect sheen of who they want the world to think they are, and I've met a lot of those types of people, I don't think they're the right ones for these kind of things.

33:54Bill Gurley: Like you want to feel that they're human and vulnerable and make mistakes and are willing to talk about them and that kind of thing. You develop trust through those kinds of conversations. Yeah. There's a community of women leaders that I built that's very small and invite only and intimate. And one of the things we have the hardest time naming for sort of who belongs and who doesn't in that community is what you just said, which is, it's like people that are willing to go there. You know, my only version of it is like, there's like level one kind of questions, you know, who are you? What do you do?

34:25Like whatever. And then there's like level three, which is what I call it, which is like, tell me about like your deepest shame and like, what's the worst mistake you've ever made. And there are just some people that can't, can't get past level one, you know, like we, we have the problem in that community of only going to level three, where it's like, we sometimes forget to be like, where do you live? Um, but I think that there's just some people you can't crack, you know?

34:48Bill Gurley: Yeah. Yeah. I feel that. Um, you talked about how competitive the venture industry can feel. And I think for folks that are in industries that feel zero sum, whether they are or not, it can be hard to reach out. It can be like really hard to be vulnerable. I'm curious if there's a story for you of taking that risk or opening up or just like how do you overcome that fear? Well, one thing you can do is just look a further step away. Over the years, you know, I would eventually, you know, have networking discussions with people that were band producers. You know, they're identifying somebody and then trying to create a contractual relationship and trying to make them successful.

35:37Bill Gurley: So you have a dynamic that's similar. And, you know, what other industries are like that? Hell, with AI, you can say, you know, you can just jump in and say, here's what I do for a living. what's an industry that has a similar motion that's not directly competitive and it'll spit out 20 ideas. Do you feel like those relationships are less valuable because they aren't in your industry or they don't understand exactly like what's going on in your career? Well, at the end of the chapter on this topic, I say there's an advanced level of this, which is I call faraway peers. And I don't think it works for people that are in the first, you know, three to five years of their career.

36:19Bill Gurley: I think it works better when you're much further along. But some of the people that have had the biggest breakthroughs, Nobel Prizes type stuff, have repotted from one industry to another. And they just bring a completely different mental framework. And when you talk to people like that, it requires a lot more sifting. There's a professor that calls these far analogies. If you're going to borrow something, you know, for your restaurant from, you know, someone that's in the hotel business, that's a little close. If you're going to borrow it from someone that's in the software business, it feels super far away.

36:58Bill Gurley: But there may be a nugget in there. And if you develop the right kind of relationship, and you have these types of conversations, your biggest breakthrough ideas might come from people that are farthest away. It just takes longer. It's harder. Yeah. And I hear you saying like, if you feel like you can build relationships that are in your industry, particularly when you're earlier in your career, that's really valuable. It does require vulnerability and authenticity. But if you were trying to do this today, how would you actually start over and what would you do? Well, I think I've been saying this as I promote my book, All of the six principles that I recommend are way easier today than they were 20 or 30 years ago.

37:41Bill Gurley: The technology tools make it so easy. LinkedIn's a great useful tool for this. You know, I think on the social networks, whether it's Twitter or Reddit, like you can find people that are functional equivalents and interact with them in these digital worlds. And a lot of people build these types of relationships virtually first and then meet them later. And I've built a lot of relationships that way. How do you do that, though, and not have it seem weird? Well, you show up with an authentic interest in something. That's why the first principle in my book is discover what it is you're fascinated by.

38:21Bill Gurley: And then you just start getting involved in the communication and the sharing on those digital networks. So you're not just pinging somebody out of the blue. You're having conversations first and then seeing how those interactions evolve. And then eventually on many of these networks, if you double opt in, you can DM. And now you're having one-on-one conversations and you're on your way. If you look back and think about the peers that have been most valuable to you and obviously some of the stories you've heard, what are the qualities that you would optimize for now that you maybe didn't fully appreciate earlier in your career?

39:02Bill Gurley: One of the things that I reflect on when you ask that question is, especially in Silicon Valley, just how surprised I was along the way at how many people said yes to a early meeting, a question, a phone call. The Silicon Valley in particular is set up in a way where I guess because so many people got help on the way up. It's just people are very open to giving of their time. And so one thing I might say to people is like, you know, until you get out there and start talking to people and asking, you know, you really don't know. In the mentor chapter, I advise people against shooting too high. like you know when we talk about mentors everybody's like oh i'm gonna go get warren buffett to teach me how to invest and and that's not gonna happen and if you go two or three or four rungs down the ladder you might be the first person that's called somebody and said hey i'd love to get your advice on how to navigate this industry and they're going to be flattered because they've never been asked that before and so you know work your way up the ladder don't start at the top, you know, be more reasonable about how you do these things and you'll be surprised.

40:23Bill Gurley: You'll just be really, really surprised at how easy it can be. Yeah. You know, never, I don't even think you should ever call a potential mentor and say, will you be my mentor? I mean, I think that just comes across as a little aggressive and creepy. You know, you, you build this relationship over a series of meetings very slowly and you, you careful not to ask for too much too early on. I think getting advice on a single question is the best way to have a short but productive conversation with someone. Yeah. It also shows that you value their time. No doubt. I think that's true of peers and of folks that might seem ahead of you.

41:07It's just reaching out with something that's tangible instead of just generic really shows people that you like thought about them, you know? No doubt. Yeah. I love it because I think you and I are so philosophically aligned on a lot of this stuff. I'm curious, like, what else would you add? What else would you want people to hear as they're thinking about, like, how to invest in peers and the folks around them?

41:32Bill Gurley: You know, I think I'd leave it with this notion of once you get this group going, root for them like you would the team that you, you know, follow the most, you know, if you're in one of these groups and someone gets promoted and you feel like that's negative for you and something's not right there, like you should be so tickled pink that they're doing well and you should let them know and you should really, really tell them how thrilled you are that they, you know, thing happened to them. And if this group roots for everyone in that way, I think one of the funny things that happens is it's almost like an infectious ideal of winning that starts to permeate everybody.

42:21Bill Gurley: And I think you slowly but surely convince everyone, one, that they're capable of winning as well, and two, that they don't want to be left behind. The peer group starts to elevate itself along the way. Well, and it really reinforces your point about like, life is not zero sum. And actually like, to me, what I hear underneath that is the belief that if you invest in this collective, you can be more successful than, you have to believe that, right? You have to believe that it can, everybody can be more successful if you're rooting for each other. This is something I started doing despite it being a sharp elbowed business.

42:58Bill Gurley: somewhere around, I don't know, three or four years into my venture career, when another VC at another firm would have a win, I would send them a note. I would just say, wow, that's impressive. And I think that is useful. Yeah. I love that. All right, Bill Gurley. Well, thank you so much. This was so great. Thanks for having me on. Yeah. I appreciate it. Work Life is a production of Ted and Pushkin Industries. This episode was produced by Isaac Carter and Leah Rose. Banban Chang is our story editor. Mixing by Hansdale Shi. Ted's executive producer is Daniela Balarezzo. Constanza Gallardo is the executive producer for Pushkin.

43:43Special thanks to Roxanne Hilash, Valentina Bohanini, Laini Lott, Tansika Sungmanivong, and Ashley Murphy. If you like the show and want more, come join the discussion on my Substack Lessons. I'm Molly Graham. Thanks for listening.

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