Reid Hoffman | Entrepreneurship and Loneliness

Hi, I'm Chris Yeh, the co author of Blitzscaling and I'm here with my co author and old friend Reid Hoffman, the co founder of LinkedIn and investor at Greylock Partners. Now Reid, it's the holiday season. Happy holidays.

You too. And of course all the people listening to us.

Now this year, the holidays are remarkably unprecedented. In fact, they're probably some of the most stressful holidays any of us have ever felt. Yet something that is still true is that during these holidays, especially during these holidays, there's probably a lot of people out there who are feeling lonely. Some of the folks who are feeling lonely are probably entrepreneurs. We've talked about how entrepreneurship can be a very lonely journey at times. What do you think makes entrepreneurship such a lonely journey?

Well, one of the things that people I think conflate is the loneliness of the CEO job with the loneliness of the entrepreneurial job journey. The founders and actually in fact they're both like seriously lonely. There's a bunch of things you need to do in order to compensate for that and adapt and navigate it in healthy and good ways. But I actually think the entrepreneur's journey is even more lonely than the CEOs. The CEO tends to be the, hey, look, the buck stops here. All the decisions that kind of are the, you know, how is the organization going to run? It's challenging to be a friend as well as a boss. It can be done, but is also challenging because of the places where they cross into each other. Generally speaking, as CEO you need to be the boss, not the friend for the care and health and growth and sustaining and thriving of the organization. And that's all true for part of the reason why groups like ypo and CEO groups all get formed as part of this kind of the loneliness thing. Now why is the founders one in particular more intense and more challenging? And I think part of the reason that is is you're taking the entrepreneurial journey. The quote that I often use, you know, throw yourself off a cliff, assemble an airplane on the way down. You're in a free fall position where you have gone out to persuade a bunch of people that this could be a very good journey to be on who've also thrown themselves off the cliff. This could be your family, you, you know, and kind of close partners who are also of course very tangibly co invested with you in this. It could be obviously your employees, it could be investors, it can be customers. Like all of these people are looking to you saying, hey, you said this is a good idea. You said this is Going to work. So we're here with you and actually, in fact, you know, you could see it, you can visualize it, you're working really hard towards it. But these are always risky ventures. And so you have this entire kind of community, this entire network, this entire group of people who have jumped off the cliff. And you know, look, there may be a few people, co founders especially, who are along that journey with you, say, look, I recognize this is a, I've jumped off the cliff and it's a risky journey and I'm doing this with you and I've done it in a risk, intelligent risk judgment way. But very often it's kind of like the look, I'm doing this because you persuaded me that it was a really good idea. And we are all in this poker term, we tend to be much more resulters or results decisioning versus good decisioning, which is based on the results. So as things get stressful or you go through the value shadow and there's things that aren't really working yet, which is by the way, multiple years in the life of a startup, then all of a sudden it's like, well, wait a minute, oh shit, is this journey working? I'm on the right journey. And as a founder you go, okay, I feel that responsibility. And what's more, it isn't just kind of the hey, you know, it's lonely, you don't have people to talk to. It's the, no, there's a whole community of people whose, well beings, whose hopes, whose fears are all wrapped up into this. And I believe that it will work and I'm working so hard to make it so. But like as I encounter my fears, as I encounter my doubts, as I encounter every rational person has like indecision, uncertainty and like what do you do? Because you go talk to anyone, you say, oh, should I create fear as a contagion in my organization? Should I have people who have co invested in this with me go, oh, whoa, whoa, wait, I thought that, I thought we were on track. And so it's super hard in the case of the founders and the entrepreneurs, even in the co founding circumstance, which of course is one of the reasons I like the co founding circumstance because at least the co founders can frequently talk to each other about this.

It sounds like you're describing some of the ways that entrepreneurs feel this loneliness, this tension, this stress. It sounds very personal. And you've been a founder before yourself. You founded Social Net and you founded LinkedIn. How was loneliness a part of your own entrepreneurial journey? At These companies, serious and real.

You know, one of the reasons why I'm now assiduously dieting to lose weight. I think I gained all my weight. I think I was one of those entrepreneurs to whom food is a drug. And you kind of go, ooh, I partially satiate my anxiety by eating strongly. Now, obviously, you tend to be also using the meals for recruiting and sales and everything else, so you're going out to three meals a day and. And all the rest, which doesn't help, but it's still kind of part of where you are. And that's, I think, my own path. And when you kind of started on the social side, this was a. Never, ever done this before. You know, who are the people who are really serious about this? You know, what are our constituencies? You know, we're going to be running into walls and making mistakes, and are we going to be tolerant of doing that together? And so a lot of the social net journey, you know, involved tons and tons of cycles of trying to keep people in the boat, because one of the things that people don't really realize that's a very valuable part of early hires and core employees and co founders. And also, as they say, look, the degree to which you help us all stay in the boat together is a very positive thing. The more that the founders or the key people have to persuade you to stay in the boat, that's distracting their time and cycles for it. So, like, one of the things that I've come to realize intensely from the social days, because there was a stack of people persuading to join, persuading to keep in the boat, that was taking just tons of cycles on. Look, it's a startup journey, and the startup journey does involve risk. But here's the way we think we can play this risk versus a. Look, we know this risk, and we think we have an intelligent play, and we're working really hard on refining it, and we're gonna take this shot, and if it doesn't work, we'll take another shot as a way of doing it. And so I found at SocialNet all kinds of just super stressful, you know, like, every day was kind of running into stressful circumstances. And, you know, that affected. I think it was one of the reasons I broke up with my girlfriend at the time. And I think it was one of the things that compounded to all these other things because of the difficulties of not even knowing what the next day's stresses would be relative to that. Now, LinkedIn was substantially better, not perfectly, because you'd done A bunch of the learnings. And so by starting LinkedIn with some people from Socialnet, some people from PayPal, which I was also part of the founding team of, you know, that made it so it was like, okay, we had more startup experience. We understood the nature of the fact it was an uneven ground. We understood that providing positive energy for each other, not blind, you know, truth telling, risks, you know, intelligent strategy, fast iteration, change, pivots, all a central, central part of it. But that part of the way that you are good partners together in these early stage journeys is to say, hey, look, we know we're all jumped off this cliff together. We all know that this is super stressful and we are trying to reinforce each other now that still at the case had places where I had key members of the team, even executives, kind of like, I won't name the individual because it's not worth doing in a thing like this, but, but like one of my key executives, like, I was literally driving to the airport to go to a conference to try to help build the marketing position on LinkedIn. And a keel executive goes, oh, I'm, I'm stressed. I'm like, I'm out. And like, as I'm driving to the airport and I'm like, okay, well, I'm not going to go get on that plane, I'm going to turn around, I'm coming over to your house, I'm going to talk to you about it. And that was a cost because, you know, this individual couldn't manage their own stress in a way that, other than calling me and saying, hey, I'm out. And so that was a cost of them being in the boat and them working versus, hey, we're helping each other go through this. And so LinkedIn, because we were more experienced, more experienced crew, understood what more of the psychology was. And by the way, LinkedIn had similar kind of moments that were like, oh, like, this is a good idea. Why did we think this was a good idea? Why did we think this is ever gonna work? You know, it's working for the other people. Why would it work for us? Just like literally 99% of startups, it always happens that way. There are these, like, you know, Airbnb just went public, but this year, you know, and Brian Chesky was talking about it as part of the post ipo. Television was like, oh, God, Covid is destroying the entire travel industry. Are we dead? Right? Is your very first thing. It's like, like, oh, I thought we had this amazing, wonderful thing. And then, oh, wait, we do. We have these amazing hosts, we have these amazing employees, we have, we can make this work. But those asteroid impacts, you know, we see it very visibly with COVID and so. But those asteroid impacts are common on the micro scale for startups and were true for both Social net and for LinkedIn and obviously, of course, PayPal as well.

When I hear you tell the stories of what happened at SocialNet, which became your first company, and then LinkedIn, where you were a bit more experienced, it seems like one of the key things you really learned in the interim is something you often tell me, which is that entrepreneurship, like life, is a team sport, not an individual sport. And a big part of it was if you can get the right team on board and you can set the right expectations around the kinds of challenges you're going to face. Some of those key transitions we talked about in Blitzscaling, for example. And then as a result, the members of the team can help share the burden. It's not like you have to carry it by yourself. Whereas in that story you told about that executive who called you as you're on your way to the airport saying, I'm out, there really wasn't anyone else you could turn to. It was all on you and was something you had to do yourself.

Yep. It's part of the thing is, okay, it's my job to do that, but there's no one I can go and throw a stress fit with and say, well, I'm out. It's like, well, okay, well, that's it. And so you have to be the absorber of all of that. And I think there's a set of things that entrepreneurs can do and a set of things that the network around them can do. The first thing is to kind of recognize is like, look, this is a risk game. Right. It's not frequently as human beings, we try to persuade ourselves, very risky or no risk at all. So like, you know, you go driving down the highway, no risk. It's like, well, actually driving down the highway is riskier than getting on the airplane. And people stress out about. Some people stress out about the, the risks of getting on an airplane. There's always these risks. And startup, yes, higher risk in a number of circumstances, especially early stage startups where it doesn't have the going concern that a going business does, which is, you know, more revenue and customers than the cost and a default motion to stay alive and all the rest of stuff. No, no, this is the metaphor of having thrown yourself off the cliff. But the things that entrepreneurs should do is say, okay, One is that I surround myself with people that I can talk to about legitimately about the journey, right? And about like, for example, even the loneliness and even the fear and even the. And I can do that in a way that doesn't seem like I'm projecting failure or projecting a lack of grit or a lack of conviction that I can make it work because of course I'm doing it because of that, but could do it in a way that I was like, look, I'm kind of talking through the experience some. And I'm talking through the experience in a way that it's because I'm trying to figure out how to help this crew, you know, my startup crew, navigate this minefield successfully and build something, you know, kind of truly amazing. And then similarly, when you're thinking about like, okay, so who do you have as investors, who do you have as board members, who do you hire? Is to actually treat as one of the significant things are, are you going to not just be helping with connections and expertise and knowledge, strategy and of do this, not do that. And so, but are you going to fundamentally contribute also on the persistence, that grit, that deep laid chutzpah that you have to go in and go do it and you're going to help with that. Right? Because that is actually, in fact, I think, you know, kind of a super important thing to be as an attribute in New York stage, to be adding in the mix and none of that is to say blindness. Right. You know, as Danielski said, on a master of scale episode is like, you need grit and wit. You know, part of his own entrepreneurial journey with kind was grit and wit and you need them both. And so it's not like just like, oh, I'm going to pound my way through the wall no matter what. And I'm optimistic no matter what. But it's like, look, we're playing forward and we're playing forward to win. And so we're keeping that team spirit, right? That life is a team sport. And so composing your team is really, really central.

As an entrepreneur, I think it goes beyond just the team at the organization. I know that in my own entrepreneurial journey, it was very important to have friends and family outside the companies that would be able to support me and, and that could provide some of that grit, some of that inspiration, some of that emotional support when I needed it. Did you find that happen when you were an entrepreneur, Reid?

I did, and I'd say it was kind of probably more through friends, although relatively few of my friends were entrepreneurs. I think Actually, one of the things that I probably should have done more before my entrepreneurial journey and a little bit more is like, gone and spent more time with my entrepreneur friends. It's actually, I think, one of the reasons why, you know, Peter Thiel, after he and Max Levchin decided they were going to start this company each, he and Max went to their kind of best friend intersecting with entrepreneurial experience. Went to me and said, hey, will you join the board and help us with the PayPal experience? Because, like, I had been talking to him for the last two years about, like, oh, my God, this is so crazy. Like, like, at literally at the end of many days and the end of every week, it was like, well, this is stuff I wish I knew at the beginning. Not facts about the universe, but just like, how to play the game, how to think about it, how to think about these questions about, like, oh, God, it does feel like, literally lonely day after day. Because in leadership, which people, of course, look at founders as leaders too, a lot of people look to you to say, I want the source of confidence from you. I want to believe that we're going to make it because you're projecting that we're going to make it. I don't want your balance investment thesis, like, here's why we have a good strategy, here's why we have a good chance of winning the game. Here's the risk factors, here's the how we're managing them. No, I just want you to say, because you're smart, to say, if we play this game, we're going to win, right? And then I'm going to go work on it. And you're like, okay, and your team will grow with more and more of those people as part of it, which is one of the reasons why it's so useful to bring in people who can help with that in kind of the inner core circle, because that will be part of the drumbeat as you go forward.

And I think there's a very important and subtle point you made, which is the need to find people who have shared this kind of experience, right? You can get emotional support from people who have no idea what it's like to be an entrepreneur, but it can only go so far. My mom, who has a degree in library science, could have told me, don't worry, Kris. I know that if you continue to work on user engagement, you're going to find product market fit and succeed. But I wouldn't believe her because I would say, what the heck do you know about it? So having people who had that experience seems like it was really helpful.

Yeah, 100%. This is one of the reasons to join entrepreneurial communities. You know, whether it's, you know, organizations like Endeavor or, you know, YPO or Entrepreneur, EO Entrepreneurship organization, I think it's one of the things that makes it okay. We can talk to each other about this. You know, the classic thing that we say about entrepreneurship is you're going to let fires burn because, like, there's so many different fires that can kill you. And he tries to put them all out at the same time. Like hiring these two people, getting that customer done, getting that product development done. You're like, okay, we're gonna get all these things done at the same time. Usually you probably won't. You won't get any of them done well enough. And so usually I say, okay, I'm gonna wait on dealing with that customer fire while I make sure that this, you know, kind of building the organization stuff is working. And then I'm gonna come back to that. Am I prioritizing the fires the right way? Am I. Am I right? This is the fire that. That if I get this one done first, I can turn around and do that, or am I misprioritizing and talking to other people who have. And content who have that expertise, who have a point of reflex, knowledge, judgment, et cetera, that can add into your own decisioning, can be super helpful in that. Not just, of course, the, you know, your parent who's like, oh, I believe in you because I love you, and I know that you're driven, and I know that you're learning, and I know that you desperately want to do this. So here I'm just giving you my unconditional love and belief, and you're like, great, I'm glad that I. I feel appreciated. And I'm glad that I know that I have someone who loves me even if I fail at this. That is support that's helpful, but it doesn't help me go, okay, am I actually playing this game the right way? Am I driving the bus off a cliff, or am I managing the turn, avoiding the cliff?

Exactly. If you're performing an emergency appendectomy on yourself, you don't need someone to say, I believe in you. You need somebody to say, listen, I'm a surgeon. Here's what to do.

Yes, exactly.

Well, that's a great segue, because obviously, as entrepreneurs are feeling these feelings of loneliness this season, they have to figure out where they can turn, where they can get help. Now, one place, obviously, is mental health. Professionals, of course, if you are feeling stressed, if you feel depression or anything like that, you should seek out professional help. That's very important, and people should definitely do that. But what are some of the other places that entrepreneurs can turn for help? What kind of content, what kind of inspiration can help them with this challenge?

Both to elaborate the point you just made, which, of course, you know, look at, we're both Californians, so it's like, hey, go see your therapist. And, you know, the. What's the joke about California is like, hey, my therapist will work it out with your therapist. The mental health professional is a very good thing. But, you know, we in California tend to be advanced in our thinking about that. But also, of course, it could be your priest or your rabbi or, you know, mentors, like, think a lot about, it's worth reaching out to the people because by the way, to some degree, you're giving them a gift of showing, I trust you. Like, this is very difficult for me. And I trust you, and I think very highly of you that you might be able to help me. And people tend to be responsive to that. So I think that's a good thing to identify who are the sources of wisdom, of strength, of perspective, and then to have them bring you in the mix. And it's obviously, you know, sometimes your significant other is a great person for this, but obviously your significant other is also taking a risky roller coaster journey. So sometimes, you know, someone who's a little bit independent of that. So that's people now in content sources. You know, one of the funny things is people tend to think about a lot of entrepreneurship content is that it's all about the tactics, it's about the techniques. It's about like, oh, how do I get viral growth and what are the ways I measure it? And, you know, what are the dashboards and, you know, what are the different ways to possibly make it happen? Or SEO or like, I'm recruiting and I'm sourcing salespeople or engineers. What do I do with that? And I'm looking for an engineer and how do I reference check? Or I'm looking for a manager and how do I reference check? And by the way, all of that, of course, is super important because, you know, part of the thing that is both scary and delightful about the entrepreneurial journey is a fire hose of new challenges and learnings and so forth. Even when you've done it before and you go, look, I know how to hire employee number five and employee number 15 and that kind of thing, it's still A new problem because it's a new market, it's a new set of competitors, it's a new technology base and a set of different things going on. And, and very rarely is it very close to the old one. There's a lot of new parts of it. Now, that being said, this is one of the things I've come to appreciate with Masters of Scale and other areas of content, is that one of the functions of this content isn't just the tactics and the how tos and the. And the what it is, but also the, the emotional context of. Right. Other people also run this minefield. And while it's super scary and it's stressful and people don't think succeed in getting through, people do get through and I can emotionally connect with them. I think that one of the things, especially because of course, the podcasting format just like this is that connectivity that, oh, I hear a human voice. I hear a human voice talking about the kinds of challenges and problems that I am facing and maintaining that energy of optimism, maintaining that it is doable. Right. That yes, we can, that hope is, is rational, that this is a possible hero's journey, and that my success in it, while risky, is part of how I'm contributing to the world. And even as the effort goes, and that I should, and that having that hope burning within me is actually not stupid, but actually, in fact noble, is actually, in fact part of aspirational humanity. And so that is, I think, the kinds of content that are also a very useful part of the repertoire. Not just the how to, but the why and the kind of the spirituality of it and the conviction of here we are, we are trying to build the future together.

That is one of the very powerful things about podcasts like this, or Masters of Scale, which is that they are scalable. It would certainly be incredibly valuable for someone to be able to turn to you and ask for your help, like that executive did when he or she said I'm out, and you were able to go in and counsel them. But obviously you don't have time to do that for everyone. On the other hand, recorded podcasts like this one could be listened to tens of thousands, hundreds of thousands, or even millions of times, reaching all those different entrepreneurs who really need it.

Yeah. One of the things that I think is an under deployed role in Silicon Valley, and I've been trying to figure out how to increase it, because I think this is also helpful, is a little bit like our earlier discussion about mental health professionals. A lot of coaching is thought about as executive Coaches is one on one coaches. And one of the things that I thought was really excellent about Bill Campbell and then the Trillion Dollar coach book that Eric Schmidt and others wrote about Bill was that essentially I actually think that one of the things we have learned some of and I hope we're going to see a lot more of, is team coaches. Like, I could almost see that as part of like when you're forming a executive staff coach, you know, of having a kind of like a little bit of a team coach who's kind of there with you, helping you guys, you know, kind of navigate that. Because there's a reason why it's kind of a quasi outsider, you know, focusing on now obviously as a company scales, as Google was doing, you know, it made sense for Bill Campbell to be full time there and do that. And that's obviously one of the places a little unstable because obviously it starts with when you're 20 people, 20, you don't really need a full time coach. But you know, as you get to, in our blitzscaling parlance, more of a village, you know, hundreds, then you of course, like, okay, well maybe now you need a full time coach. But I think that's actually one of the things that I would hope that we would see more of. And the coach, you know, doesn't only need to be rah rah as much as, hey, I'm trying to help us all stay on the same page in communication. On the same page for what the vision is, on the same page for the frictions that evolve to do we think each other doing the exact right job? Are we maintaining trust and faith in each other? Part of how I got into this was not so much Bill Campbell, who I did meet a couple times, but actually Fred Kaufman, whose book Conscious Business and the Meaning Revolution. I think both books are really, really great because it's kind of the question about the, you know, how to have. I think I describe him as the priest for Adam Smith, kind of the spirituality of this kind of capitalism. And that it is actually meaningful. It isn't just this, oh, you're just in it for money, which of course a bunch of people are. And so. But why you could actually have a mission and the mission's real. And the fact even though the mission is targeting a very successful business, that doesn't undercut that. It's real mission for business. And so I think that anyway, that is, I think another role that I think is important within the loneliness thing. And then what I would say is part of the things that I think Entrepreneurs face. Because I know I face this when I look at this, like, oh, if I go and confess uncertainty, if I go and confess fears, doubts, am I undercutting my chance to success? Because everyone says, you know, persist, you know, have grit, you know, show your determination. Am I doing that? And the short answer is, with some people, you are. You have to be very careful about who you talk to, because if they hear it from you, they go, oh, that means you're not as convinced. You're not. You don't believe that you can really make it. But that's part of the seeking the right people. Because you don't want people who are just saying, oh, there's no fear here, there's no risk here. But you also don't want people to go, oh, my God, I totally agree with you. I'm abandoning the ship because you're like, no, no, no, I'm not talking about this because I disbelieve. We can get there. I'm talking to you because I'm working through these things so that we can get there more strongly. We can navigate what the issues are. And I myself am a reasonable person who has eyes, who has ears, who can see the risks that we're trying to navigate and what we're trying to do. And I think that's a super important part. So I'd say with. To the entrepreneurs who are confronting this very proactively, build those trusted bridges with folks who go, okay, I'm on this journey with you and I'm trying to help you. And that doesn't mean I'm close eyes, you come and say, oh, I'm totally fearful about this. Yeah, you should be fearful. That's a huge landmine. Right, right in front of you. Now, maybe you can navigate it, but fear is rational. Right? And here we go.

Well, in a year that has been so unprecedented and inconceivable, so full of turbulence, we could hardly ask for a better guide, a better member of our network than you to help us figure out what to do along the way. I think it's been very important that we could share many of these thoughts and lessons and learnings with the audience out there. With 2020 about to exit through the rearview mirror, are there any final thoughts you'd like to share with all those entrepreneurs out there?

Well, obviously, this year has been unprecedented in all kinds of ways. You know, you've got not just the pandemic, but in California, the wildfires. You've got political fires all over the place, not just in the U.S. you know, many countries. And it's been scary, it's been difficult, and, you know, part of that loneliness and part of that fear. You know, one of the things that I like to point out to leaders, founders are leaders, CEOs are leaders, executives are leaders, but also individuals are leaders in their organization and their communities, is that precisely when you are encountering these difficult times, stress, fear, doubt, suffering, that's the time where you can actually. It also gives you a chance to. To show heroism. It gives you a chance to show even in your own suffering. It's one of the things where I say, look, yes, I'm navigating, yes, I'm dealing with the asteroid that has crushed so many small and medium businesses, SMBs, throughout the US and other countries. Yes, I'm dealing with that. But let's look at how we can do this together, and let me be a leader in pulling our wagon train together. The best metaphor that I think of for entrepreneurship as pioneering. And too often, people. Oh, pioneering. That's like individuals like you're a scout going Lewis and Clark across the Pacific Northwest. And you're like, no, no, I mean pioneering a lot more like Bob Putnam in Bowling Alone and his other excellent works, which is it's a wagon train. And helping form that wagon train and helping each other. You know, being. There's this new book coming out, Mutualism. Being Mutualists, about how we're helping each other and being the lead in helping set that up doesn't mean that everyone needs to follow you. It's, hey, let's link arms, let's link hands, and let's step forward into doing that. And one of the things that I love about entrepreneurs is that entrepreneurs are part of how the new industries get created, the new jobs get created. I mean, part of what we're going to need desperately in 2021 to recover from this disastrous year is a whole bunch of entrepreneurship. And obviously, one miracle that we'll be seeing is this miracle where vaccines used to take years to create. Because of the global networks, because of the collaboration across countries and science and data and ideas. We have multiple vaccines that have been created in months and are deployed and working in countries already. And so this is a miracle of modern times. And so when you face fear, when you face doubt, that's precisely a time to say, this is a chance. This is a ability, an opportunity by which I can express leadership, I can express heroism. And so always remember that when you encounter it as difficult it is. And then, of course, you know, rely on your allies, rely on your friends. Rely on your colleagues, rely on the people who are close to around you and your mentors and all the rest. And life is a team sport. So good luck.

Well, I think that's a perfect note to thank all Those heroes of 2020 who've helped demonstrate to all of us that we are not truly alone. Thank you so much, Reid. That concludes this episode of Gray Matter. You can subscribe to gray matter on soundcloud.com greylock partners. You can also find new episodes and blog posts on greylock. Com. You can follow Greylock on Twitter at greylockvc. I'm Chris Yeh and thank you for listening.