Reid Hoffman | Game On

Foreign hi, I'm Chris Yeh, the co author of Blitzscaling and I'm here with my co author and old friend Reid Hoffman, co founder of LinkedIn and investor at Greylock Partners. Now I've been looking forward to this conversation for some time because we're going to focus on a topic that is near and dear to the heart for both of us, which is tabletop games. In interview after interview, you've spoken about the key role that that tabletop games have played in your life, especially in developing your abilities as a strategist. I'm thinking, for example, of the special Turn the Tables episode of Masters of Scale where June Cohen interviewed you instead of you interviewing some other luminary. But you've never sat down for an extended conversation where the games themselves were the focus. That is, until now, obviously.

Chris, I love this subject. We talked about it and when you suggested it I was like, this will be fun.

So I thought we'd structure this conversation a little differently than we normally do. We usually have questions and answers. But I think what we should do instead is start with an overview from you on why games are such a powerful tool for entrepreneurs and strategists, and then let's go into some of the individual games that have played an important role in your life. So talk to me about games. Why are games so important?

Well, games are pretty central to understanding and getting a detailed knowledge and cohesion around the subject you already brought up, which is strategy. And what is strategy and how does it relate to tactics and how does it all play. And it's one of the reasons why even in where in human history this is developed, obviously is within kind of armies and war groups and so forth. Because when you look at how people started training and developing, well, you'd have war games to figure it out and you would play strategies and scenario analysis as part of doing it. And games give you that ability even as a kid in order to do this. Because the thing that people don't really tend to think about like, well, how do you coherently express a strategy? What is the relationship between the strategy and the goals? What is the relationship between strategy and a tactic? What's a tactic? What's a strategy? What are the things that you can do to condition whether or not the strategy is good or not? When you're generating strategies and you're learning which ones of them tend to work and tend to work in what circumstances against what kind of opponents and what kinds of things, what are the things that you need to do and that's why games is so essential to that. And that's why, you know, when people have asked me in these various business contexts, like, how did you learn strategy? And they're thinking, oh, you went and got an MBA or, you know, something else. I was like, no, actually, in fact, I played a lot of the kinds of games that played out in a strategy. And one of the things that then people think is like, oh, you mean like chess or go? And actually, in fact, while I think chess and go are great games, great tunings of the mind require some real dedication, mental focus, reflect certain kinds of skills. They don't tend to be the kinds of teaching strategy and tactics that I come to appreciate because they're deterministic, right? It's like, well, actually, in fact, there is no outside variables. There are no luck. There is no changing, you know, weather or market circumstances or other kinds of things. The game is totally transparent. You know, you see everything that's on the board, et cetera. And so the kinds of games that I like were the games that did have skill. You could learn rule sets, you could learn combinations. You would learn what is a set of, a general set of strategies and a general set of tactics. But then you had a lot of other kind of maneuvering variables, all the way from rolling dice to, well, really what's happening with your competitors and a bunch of other things, and lack of knowledge about what's going on, which is also much more true to the real world, to the business world, everything else. And that's why games has been so integral to my development as a strategist and as theories of strategy and theories of business strategy.

And it strikes me that there are those two different things that make the games in particular that you've played so critical. The first is that they present the ability to give you immediate feedback. Unlike the real world, where it may take weeks, months, even years for things to play out, a game allows you to go back and forth, try things out in a very short period of time, perhaps just a few hours, and gives you that kind of feedback that you can learn from. But the second point of it, which is really important and is that it's not just about the classic chess and go games, which, as you point out, are the stereotypical things we think of as developing these great strategic thinkers. Your point is. No, that's actually completely wrong. Those games are deterministic. You can go find a chess book that will list the 1500 different chess maneuvers. And this is the Sicilian. And this is the thing that Kasparov did in this particular match. And people will recognize it immediately and that's really cool. But it doesn't prepare you for the real world where you cannot just simply say, well, this is exactly what happened 600 years ago.

Yes, exactly. And what's more, there's a whole bunch of different variables because like if you're doing business strategy or for example war strategy, you don't control weather, you don't control, you know, other kind of surprise breakdowns in supply chains that you're saying, look, I'm pitting my pure strategy in chess or go against the other person's pure strategy, but it's within a very narrow set of moves. And you know, sometimes, you know, this is part of the reason why by the way, even learning some decisioning around poker, which is really good, is because you go well actually, in fact, there's a randomness to what card comes up. And so you need to be adjusting your probabilistic strategy based on, you know, call it Texas hold' Em based on what cards now get turned. And that changes what you was your previous strategy and tactic from before to now adjusting it. And that kind of adjustment is one of the things that's actually in fact through epistemology, through learning, through discovery, through factors, is one of the things that's actually really key to being a really good strategist in life, in work. Right. In the circumstances that are happening outside of the pure game universe.

Exactly. You're not just handed a situation with a clear set of choices like a Harvard Business School case study. You actually have to work through the epistemology yourself, which is what do I believe, what do I not believe? How do I learn? How do I know any of this? And having the randomness of the games, having the interaction with the other players really provides you with some strong training there.

Yes, exactly. And that's the reason why these kinds of primarily board games as the dynamic. And then of course the other thing that, that board games which we'll get into a little bit more depth, they also provide you most interesting human games are not one to one. Right. They're not this kind of the arm wrestling contest between two people. Most of them are actually in fact where there's a set of people and that set of interactions played out is also part of what makes games much more the kind of guideline the kinds of circumstances you find yourself when you need to apply strategy and tactics in, in reality to mapping to the circumstances in the world where you're trying to develop strategies and tactics.

Gaming is the original Place that people can learn about co optition and all those different things on that continuum between head to head versus building a coalition and everything in between.

Exactly. One of the games, which I don't think we are going to talk about much, I only played it twice ever, because I decided this is not a game that you really wanted to to playing with your friends was a game called Diplomacy. And Diplomacy. There was a whole magazine devoted to this. And one of the cartoons that I most remember from Diplomacy has this kind of three panel cartoon. And the first question says, will the real Diplomacy player please stand up? And the middle cartoon is the two, the three people in a row. The two people on the outside of the row stand up. And then the third scene in the cartoon, they fall over dead with daggers in their back and the middle human figure stands up. And the problem with diplomacy is the only way to win in Diplomacy was basically to get someone to believe that you were telling them the truth about how you were going to move and then act differently in a way that essentially slaughtered them. And so that kind of the only through deception, which of course is a particular model of one kind of diplomacy. Very cynical. Then it's like, I don't want to play this game with my friends. I might be willing to play a game of diplomacy with people I don't know because it's like, okay, fine, let's see which of us can be most persuasive with strangers. But like the. You know when you're talking to your friend and you're, you're saying, chris, don't you trust me? Of course I wouldn't betray you. It's like, like literally the first game of Diplomacy I played as a kid, I think three people didn't talk to each other for a week afterwards. Like, we're not playing this game anymore.

Yeah. I think that that's one of the things that you also learn about games as you play them. I know, for example, that I've long avoided the game of Risk. Not because I don't think it's interesting, it can be fun, but because my observation was there is at least a 50% chance the game would end with someone storming off in anger. And that was not a good use of time.

Yes. Because, you know, the thing is, you're playing this game, but also you're going through life with these people. Right. So, you know, what does that look like? And that's actually an important part of the lessons of board games.

Well, let's start with the first game that you provided me a List of games. Let's start with the first game on the list, which is actually the first commercially successful printed strategy game, which is Tactics two. How did you encounter this game and what did you learn from it?

Tactics two, maybe in one of the games that I discovered by going down to the game store and saying, hey, I'm interested in this gaming thing, I'm going to buy one and start doing it. I think it advertised itself well as a, you know, kind of an entry board game where the basic things where you had a map and a set of chits with different, you know, infantry and tanks and so forth that had different attributes and would play different ways against each other and you'd have a relatively straightforward battlefield and then you would kind of deploy and play that out. And then there was a set of things that you had to develop and start developing tactics and strategy and how those related. Because the way that conflicts would be resolved, like, oh my, you know, my infantry and the tank are fighting here was through dice rolls, which would have statistics. So it isn't like the tank 100% always took the infantry or the infantry. And so you had to factor that into what you were doing in terms of seeing how things evolved and changed. And you had to have plans B, and you had to be getting a sense of what it was doing. And that was the reason why, for me, I think as a kid, I was like, oh, that's the first game. I should go buy that one. But that's the thing that made me start understanding where you had to develop the questions. Like, for example, part of what you begin to think, well, you. What's your strategy? Well, what's your goal? Who are your opponents? What does the battlefield look like? What are the things that may affect, like your opponents will have strategy and tactics. Well, what's your strategy against their strategy? Why will your strategy prevail? A simple baseline way of understanding tactics is tactics combine to form to your strategic goal. But sometimes, by the way, the tactic is extremely important. Like, for example, you think, oh, I think I know something about how a line of tanks can work in this way, in this combination, given this rule set and everything else that they don't understand, they don't understand that could break through their ranks doing this. And they don't. They don't get that yet. So I can, that can be my strategy. And then my tactics are, how do I line up my tanks? How do I kind of conceal my strategy from them so they don't see it coming? Because you presume that you have an intelligent proponent until it's too late. And then you had to make these kinds of adjustments. Because, by the way, sometimes you have a really good strategy, you have a better strategy than your opponent or opponents, but sometimes luck just doesn't play that way. And you. You make sure that you are, you know, like dice rolls and so forth, and you make sure that you're. You're trying to factor that in as best you can. You have redundancy in your strategy. Sometimes you have a plan B that you can try that may not work as well as Plan A, but. But might actually, in fact, still work, you know, et cetera, et cetera. And. And that. And Tactics two was the thing that got me into that and got me into becoming right, because it was like, oh, this is a lot of fun. And then what you start doing is you're building these mental models of strategy and tactics, and you're thinking about probabilities, and you're thinking about the kind of the role of knowledge and what you know and what you don't know and deception and all of that into the baseline of what is most often called Avalon Hill board games, you know, which is kind of the broad range of this kind of board game. And Tactics 2 was the very first one.

Now, one of the things that's really interesting about what you just said is I think it reflects something that comes up often in the startup world, which is you should not judge things purely based on outcomes. You can make the right strategy, you can choose the right tactics for a particular battle, and then the roles just go against you, and you have to be able to distinguish between, I had the right strategy and tactics, but the roles didn't go my way. And you also have to, as you put it, have a backup strategy, have resilience strategy, be ready for the fact that maybe things won't go the way you think they will.

Yep, exactly. And part of the discipline of that is to realize that you're not always. And this is like one of the things that Annie Duke does very well in her book on poker and decisioning, which is don't be resulting. Like, be decisioning and processing and making sure that you're. You're doing well. And so the postmortem isn't, did I win or lose? That's, you know, not fun. But it's like, did I play a good strategy? Was this a right strategy or was I just lucky? Right, because sometimes, by the way, you were lucky. And sometimes, by the way, like, one of the things I think you learn by Playing these games with luck, is that part of when you say, well, just lucky, it's like, well, actually, in fact, part of life and business strategy is you try to be playing in a way that luck favors you more often. It's not that you make your own luck because that goes all the way back to determinism. And, and like, we like to have this kind of teleological, like, oh, you can totally control it. It's totally, totally the way you are. And I think, no, no, no, what you try to do is you play in a way that you are more likely to be lucky. Things are more likely to break your way. You have more shots on goal, you have a natural title way behind you, you have a network of support in various ways that enables maneuverability. There's a lot of different ways where you can increment your chances at luck that are important to do both as individual strategy and as also obviously company or product strategy or whatnot. And I think that's part of these kinds of games teaching you those kind of mental models and how to both apply precision thinking while also being very adjustable.

There's a game mechanic from the game Dungeons and Dragons which we're not going to discuss at length today, but which I think really captures this, which is the mechanic of advantage. And what advantage means is that for some reason, because you have the help of an ally, because you have used some sort of magical item for whatever reason, you have advantage. And that means instead of rolling the dice one time and then seeing what happens, you get to roll it twice and pick the better result. And the chance to roll the die more than once and as many times as possible really captures what strategy is about. It's about giving yourself the chance to roll as many dice as possible so that you have the greatest chance of winning.

Yeah. And that's actually one of the things that people most often mistake when they approach strategy, as we talked about earlier from a chess and go perspective, is they say, no, no, I want it to be completely deterministic by which I 100% predict that I win. And you go, well, boy, that's a very nice universe if you can live in it, which very, very few of us can, and the very few circumstances look that way. However, once you begin to understand probability, then you begin to go, oh, wait, if I can roll the dice twice, that changes my probability landscape. Right? Because if you say, well, like for example, I got two chances to roll a six on a six sided die, my probability landscape is much bigger. Right. And if I can have Four chances to roll the dice, then it's even much bigger. And so that's the kind of thing that you begin to realize thinking in probabilities and thinking in doing strategies that maximize your chances that the probabilities will go your way.

Now we mentioned briefly Dungeons and Dragons, which is an example not just of a tabletop game, but of a role playing game. And the next game on the list, which you are actually one of the contributors to, is the second most popular role playing game of its era behind Dungeons and Dragons, RuneQuest. How did you end up selecting RuneQuest as opposed to Dungeons and Dragons and talk a little bit about how you ended up becoming a contributor to the game because it's a really cool story.

Well, yeah, and we can take a long time with it. So I will do the abbreviated version. I was first introduced to Dungeons and Dragons when I was a nine year old because the kid sitter that my father hired had a very good way of placating young boys, which is you would just kind of run them through a dungeon Dragons thing. And so I was literally the kind of kid who would say, dad, don't you have like dates that you need to, you like you need to go on? Because I think, you know, that'd be a good thing because I, you know, it was a fun thing to do. And so I started obviously with D and D, which is obviously great system and a bunch of other things. But then what I found when I started exploring what my co students were doing, the kids that were playing D and D were doing a lot of what was frequently at the time called power gaming, which is like I have the paladin of a millionth level with a, you know, blah, blah, blah. And it was kind of this weird stick figure ego kind of thing and there were no real dimensions to it. And the thing that I wanted in the gaming was some combination of kind of call it narrative gaming, which is that you're weaving a story, you're characters have stories, they have interactions, they're interacting with a story and so forth. And war gaming, which is you're solving puzzles and problems. And so the game is still trying to. Because, you know, part of the narrative is you're trying to solve the problem, you know, in simple fantasy parlances, you know, are you going to, you know, kill the dragon or save the town or you know, da da, da, da. And then doing that in a more kind of interesting basis. And then. Why RuneQuest? Well, I discovered that the headquarters was in walking distance from my house. I got a Friend of mine who lived in that block because one of the things, they were running it out of a house where they shouldn't be. So they were very nice to their neighbors. And one of my friends was one of the kid neighbors. So they kind of couldn't kick the kids out. Kids out when they showed up. So I showed up with the kids and they're like, kids are getting in the way. And then what I did is they had published a kind of a starter pack, scenario pack, with the next publication of an additional runequest. And I went through it because they did a kind of sloppy, half assed job on it. And I went through it with a red pen and I brought it in to Steve Perrin, who is the. Greg Stafford was the founder and inventor and Steve Perrin was the editor of it at the time. And there were a few other folks who were doing different things like the Different Worlds magazine and the building and so forth. And I brought it in and initially I could see the look on his face, which was like, oh God, this kid is pretending, presuming to tell me my business. But Steve was curious and intellectual and so he cracked the COVID of the thing I handed him, started looking at it and went, okay, hold on, sit down. And then read through it and said, why did you take this? Why did you think that? And walked through it and I went, okay, huh? You want a job, right? And I was like, what do you mean? He's like, well, I got another thing I'm working on. Like, will you go? And this was like, think a Thursday. Will you go look at this and tell me what you think and I'll pay you for it, you know, depending on what you come back. We didn't come to an actual exact hourly rate, but it was like, okay. And so I took it home and looked at a little bit on Thursday. And then, you know, in a way that only an obsessive kid does and you know, all the entrepreneurs, you know, who listen to this will reflect on this. You know, I basically worked on it sleeping like three hours a night between Friday and, and Monday. And then Monday afternoon after school walked over with a. And here's my work. Like, I did it. And that's part of the reason I have a. I have a credit in Borderlands because that was the scenario package. And I was doing everything from tightening up certain of the problems and the plot lines, adding certain characters, deleting other characters, changing what the scope of the math looked like. Because where the war game part of this is, well, if you attack the dragon by going down into the one entrance of the cave that the dragon can breathe fire out of. You're just all toast like that. Just stupid. You have to actually have it because you have to apply your strengths to the weaknesses and where are the places of strengths and weaknesses that apply to a good plot? And I'd been a game master for a number of years then at that point, so I knew how to do this kind of stuff. And so I went through it and they went great. You also have a co edit credit because you just helped tighten this up. And they publish it and gave me a check when my dad's like, where did you even check for this? And I'm like, oh, I did some work, right? He's like, we're depositing it. You're not allowed to spend this. I'm like, okay.

Of course, that is a classic parent move. And I still use it myself and my kids. But I have to imagine he felt pretty proud that you had done something like that.

Well, I think the principal thing, he was like, oh my God, am I raising a mutant kid who's never going to be able to care for himself to, oh, looks like he could at least get a job doing this. So, okay, fine. If you're obsessed about role playing games and whatever this thing called RuneQuest is, go ahead. I think it delayed my getting a paper route by a couple years because I think otherwise he would have insisted on a paper route earlier.

I feel like you definitely came ahead in that particular exchange. I don't think there's a lot to be learned from running a paper route.

When I reflected on it, because I was thinking about this games thing, there were a lot of things that I Learned from the RuneQuest because not only is the narrative story important, but when you think about the narrative story we pulled together on companies and you think about what is our problem solving as a group, what is our mission? Whose identities are connected to the mission in different ways? How are our identities connected together in that mission? That's all part of what a adventure in these role playing game systems look like. And then you actually have various forms of leadership that are connecting the group. Like part of what you do across the is connecting that leadership to that. And then in the most interesting way is what does winning count as with games? Like most of these game systems. And this is one of the things that's really good about the role playing game systems, the RPGs is most of these games are like, well, they give you what your outcome set is. Your outcome set is you Crush the other side in Tactics 2, you capture the flag, you da da da da. And there's one objective function, but actually. And obviously there's objective functions in various forms of games we encounter in life. It's like, you know, do you have a going concern, the business? How much do you grow it? What's your revenue? What's your profit look like? You know, so, you know, someone else who wins the customer account? You know, those kinds of things are, you know, parallels. But on the other hand, like, the game isn't just like, oh, I won because I made a dollar more revenue than you did. Right. Like, there's a lot of other elements to playing the game, like, who are we as people? What is our role in society? These kinds of things. And I think the RPGs were a very good framework for exploring that in different circumstances and kind of playing that out and kind of getting solid on what your identity is. I mean, it's one of the things that I've actually thought would be an interesting thing to create as kind of RPGs that weren't just the, hey, I'm a paladin, I have a sword, and I'm going to go get the dragon and save the town. But things that I had more interesting parallels to the lives that we actually find ourselves in.

Yes. And I think one of the interesting things about role playing games in particular is I think we have a greater understanding now that role playing games are not just games. They're also, in a very real sense, improvisational and collaborative storytelling. And that really gets to the narrative that you were discussing. And that sort of collaboration has made role playing games more popular than ever. They have become an entertainment form that is on Twitch, for example, with the famous critical role, the various podcasts, which are episodes that include gaming sessions. And the thing is, this improvisational comedy, it's not like there is somebody who is in charge and telling everyone what to do. Instead, you're feeling your way through and you're learning to exert leadership in a way that's indirect or via influence. And this is great preparation for the world of entrepreneurship.

Exactly. And great preparation for lots of elements of life. Because the question is, while most of us don't pay much explicit attention to it, all of us are going through life with a story running through our head, actually. In fact, the vast majority of us are going through a collaborative story one way or the other, because we're not the only people in our narrative. And then how do you collaborate on those stories and applying some thought and making It a little bit more explicit and nudges and so forth is a way to have a much better story together.

Absolutely. Well, the next game that I wanted to discuss is a game that we have both played. I remember first encountering it as a teenager when I was away at the center for Talented Youth or CTY Summer Camp. And that is Starfleet Battles, a game designed to appeal to the Star Trek fan in all of us. So why don't you take us through Starfleet Battles? How did you encounter it, what was it all about and what did it teach you?

So the reason why Starfleet Battles add something to the previous two games is not just the IP and the shared fantasy universe and a bunch of other things which are all of course fun. But in Tactics two and in the Avalon board games, some of the Avalon Hill board games tried to add in things like supply chain and so forth. There was always kind of a weird add in to it. And the role playing didn't actually realize like all of the kind of logistics and different kinds of equipment and all the rest of the stuff. And that part of what Starfleet Battles added was, well, actually, in fact, when you're doing these things, look, everyone in a military college and everyone in army realizes actually logistics is centrally important, that you can't have war without a supply chain line. And these things have these underlying production and economic bases and supply bases and so forth. And so it isn't just like, and this is, you know, like once you begin to realize, like, how did Napoleon fail in Russia? It was the. Not just the, oh, well, he mistook the weather, but he mistook the supply chain for how this, you know, would work. And so part of what Starfleet battles required is that you would configure your equipment, you would configure what kind of supply chain would be it. You would be thinking about your equipment relative to the other equipment, you would be thinking about your equipment relative to the battlefield that you would be on. And then you would, to some degree maneuver to try to choose which of the various factions, which I didn't remember all of them until you reminded me of them. But which factions would you actually prefer to be? Because sometimes in this one you'd prefer to be this faction and this one you'd prefer to be this faction because it depended on what the scenario is or what the circumstances that you would be playing. And that in addition to kind of factoring in all of those variables, because by the way, you say, well, how do those variables play in. Well, it's like, okay, well, obviously it isn't just if you're doing a hardware product, what does your supply chain look like for delivery to market and all the rest, and what does your error rate look like and those kinds of things as early, you know, plans on that. But also what are your production capabilities? So like you say, hey, how fast do we rev our software and do we get the learning curve to understand what the customers want and what are the next features faster than our competitors? Well, that's actually part of, you know, how strategy plays out and that's part of the understanding of the battlefield that the kind of Starfleet Battles was the indicator for me. And then as the last part of that, of the things that I kind of learned in Starfleet Battles was also surprisingly important to even the business world is the importance of deception. And you'll say, oh, there isn't much deception. It's like, no, there's tons of deception. It isn't deception like the kind of bad deception of like I'm lying about my product. But there's reasons why, for example, one of the companies that's most locked down about that is Apple. And they go, it's a firing offense to reveal anything about what we're going to be doing because we want the maximum of starter advantage to our product to benefit from creating the new category that we're doing and to do that in a way that we get the maximum inertia and headway so we maximize. No one knowing about it and no one knowing about it is a form of deception. More advanced deception is, oh, you think we're going to do, we're going to release a new thing about this and actually we're going to release this other thing. And again, that's all in the healthy competitive side of things. And so there is no competition without deception. And actually, in fact, Starfleet Battles, basically you can't play Starfleet Battles without having a theory of deception that plays into your strategy of what, what you're doing without just losing. Right. And so that was another part of it, that kind of the supply chain things and the, the match of that to your battlefield and then the role of information and deception and how you're playing it out and how you need to make adjustments from it. Those were all things that I picked up that were like Starfleet Battles became another one of the key ones. And learning strategy and tactics that apply.

To business and Starfleet Battles is definitely one of the most math intensive of these games, without question. And I think it's both in the long term and the short term. In the long term, as you mentioned, there's the question of supply chains and where do you locate star bases and how do you move fleets around and the like. And then in the short term, there is the question of resource management. The ships are designed so that they cannot do everything at once. So you cannot move, power your shields, charge up all your weapons and fire them at once because there isn't enough power to do so. So you always have to be making decisions, sacrifices, understanding that you're not going to be able to do everything the way you exactly want it to be.

Exactly. And that was an important evolution in the toolset models of thinking.

Now, in Starfleet battles, they have a set of factions and several of them are familiar to most Star Trek fans. So the Federation, the Klingons, the Romulans. Many people who are fans of the original series may also remember the Orions, the Slavers, and the Tholians, who appear briefly in the Tholian web. And then there were a couple like the Kzinti, who come from Larry Niven's known space property, but were a part of the Animated series. And things like Hydran and Liren, which were just made up for Starfleet battles, they all have different characteristics. We won't go into the characteristics of each of them now for fear of boring the crap out of our audience. But which of these factions did you tend to play and why?

So I tended to play Romulan or Federation Romulan because once I realized that a key thing in this whole thing was deception, Romulan and cloaking technologies ended up being a pretty central way of reconfiguring battlefields. Doing things like you would build some small. Like, you know, y' all tend to think it's of us geeks and at the moment, everyone else tune out because we're gonna geek out for like 60 seconds on, on this. But it's like, oh, it's a. It's the Romulan warbirds that cloak and so on. Well, actually, in fact, like, one of the things I would do in Starfleet battles is I would build these little tiny cloakship that would lay mines, right? And so the actual thing would be using the cloaks to reconfigure out of mining fields to use. The fact that I could lay a minefield that the other person didn't know would be there rapidly during the actual combat was a point of deception in the thing that would go, ooh, I'm gonna win, because I see he's exposed his flank here, and it's like well, I exposed my flank there because I laid a huge. I just finished laying a huge minefield along that flank to tempt you to come in on that flank. And that was why the Romulans and then the Federations, because the Federations were the best generalists. It was the. If you didn't really know what you were gonna encounter, there was a lot of different variables. Say there were five different people playing and so that you wanted to be able to have most flexibility and adaptability. The Federation generally was the right set.

For that and just to really drive away the audience. The reason why Reid's strategy of using the cloakships to lay mines is so brilliant is because in Starfleet battles there's a concept of overloading your main weapons. And overloading your main weapons is the main way you break through shields. You basically overload them, power up to double power, but that means they have a shorter possible range. So the way you won in these games if you wanted to win decisively, is you had to close to point blank range. And that left people completely vulnerable to Reid's nuclear space mines.

Yes, exactly. It was a come closer, come closer look, little old me, I'm weak here, you can finish off some of my important ships. Right? Yeah, that was the fun thing. And, and by the way, an important illustration is, it's a common is how strategy and tactics come together, which is people frequently go, well, you first use strategy, then you figure out tactics. Or you only do tactics and strategies naturally merge and you actually need both and you need to be iterating between them. And it was like, look, I realize I have this mine laying tactic. I can then configure strategies around it that can be a winning strategy. Because by the way, it isn't just that I laid the mind, it was that I. Because you had to be able to get the other person to come into the minefield. That was really important. How do you get them coming in the. Well, you do this other tactic and so forth. And then what happens if they don't take your tactic? They go, okay, we didn't take the bait on that. What else do you do? That kind of thing is the requirement for going through it. And it's part of the interplay between strategies and tactics.

We could talk about Starfleet battles all day long, but again, we're trying not to completely drive away the audience. Let's move on to the next game. Wooden ships and iron men. So Instead of the 23rd, 24th century, we're now talking about the 17th and 18th century, the age of sail and cannon, armed vessels. Talk to me about wooden ships and ironmen.

So there may be other games that had this very particular gameplay element, but Wooden Ships and Ironmen is the one that I discovered it and I actually thought it was a very good way. Like just what we were just talking about is like understanding the interplay strategy and tactics and getting a fast loop on it. The fundamental tactic was you sitting there with ships. And the whole point was you're trying to sink the other ships and not have your sink. So what would happen is in a turn you would have to plot your ship's motion. And then as the term ticked off, and I think it was like 30 ticks in a turn or something. So each movement. And so you had only two choices that you could make for the next 30 ticks, which is do you stop your motion? So you could say, okay, I'm going to stop, right? And when do I fire? Because I can fire once during this. And so what you're doing is it's that raw kind of against opponents because the other people have to do the same thing. And so what you're doing is you're thinking through what do I think that that person's likely going to do with where their ships are currently. And by the way, of course, you go through turn and then turn and then turn, and then the, you know, the ships are in various positions and what do I think that they're going to do for their next 30 ticks of motion? And how do I get into a good position where I could shoot at them, given that anticipation? And when do I shoot and where do I think they're doing as part of that? And that gave you a very quick cycle between like a strategy and tactics because they give these micro tactics of do you stop moving? Because you go, oh, like it's worse for me to keep moving so I stop. And then when in this 30 ticks do I predict will be my optimum chance to shoot, right? And obviously the person who shoots first has the advantage of you might do the damage that then hampers the other person shooting back, because this is the classic 18th century broadsides and so forth. But you might also, like, for example, classically, if they had to shoot at you obliquely to do a little bit of damage, and then they move into where you could broadside. Great. And sometimes, by the way, you might even hold on to your shot because you go, okay, I know where they're going to move. I don't want to allow them to Move there. And so they'll stop moving to not allow me to broadside them because I want to keep them in position. And then you'd still shoot, but you'd shoot unaffectively for that period, but you kept them in motion. So you had all of those very detailed thing that you would play again and again and again and again and again and again in each turn. And that. That was. I found a very fun way to kind of be matching out this play. And it was the first game that I discovered this mechanic with. And it's a very fun mechanic to hone your thinking and hone your skills.

And it really is, in this case, iterative scenario planning, where you're coming up with scenarios and you're figuring out what to do, and you're recognizing that it's a dynamic system because your actions will cause the opponent to change their decision. But it's not like you can just simply react. You have to make a plan every turn.

Yes, you make a plan. And by the way, if you made a bad plan where you just say, okay, stop, because, you know, usually speaking, if you got to tick two and you stopped, you're like, okay, you're probably like, this was a bad turn for you. Right. Because you're trying to get into position in a good way. You know, that's part of the reason why wooden ships and ironmen. Yeah.

You would only want to do that stopping on tick 2 if you had planted your nuclear space mines earlier and that enabled you to finish them off.

Yes, exactly. Which no such things.

Now, the game that you are probably most associated with, because it has come up time and time again in various interviews, is what is known as a German game, probably the preeminent German game, Settlers of Catan. So talk about this game. How did you first encounter it? Are you patient zero for settlers here in Silicon Valley? And talk about why you love it so much?

I'm certainly not patient zero. Settlers of Catan is part of a phenomena known as German board games. And the German board game phenomena is German families, through work mandates and everybody else tend to get home at 5. So the one hour of television that American families tend to aggregate around, it's multiple hours. And so they tend to have a lot of more interesting board games, board games, more complex rules, harder to learn, like, you know, Settlers of Catan. Like, my recommendation to everyone, including my smart friends, is don't just go pick it up, read the rules and start trying to play it, because it's going to be very frustrating. Find someone who knows how to do it and have them teach you with a set of different kind of teaching games. And like, for example, one of the things I've learned about teaching my friends, and that's part of the reason why you're. Oh, are you Patient zero is playing first with kind of cards down, where we're all kind of playing the game together, where we see everyone's cards and doing everything and, and facilitating that so they can get a mechanic for what a good decision and a bad decision is. Because it's very easy to ignorantly just lose badly in Settlers of Catan, despite the fact that it has all of the other kind of characteristics that I like about general games, probabilities, roles and so forth. Because you can win. Like, you could have person A with a really good strategy and person B with a mediocre strategy, and person B wins because their resources rolled all the time. Now, if person B really doesn't understand settlers at all and misplaced their initial settlements and roads, well, then, even then you have to be super lucky. So, you know what? I remember actually doing a game of this where I was, I was teaching Richard Waters, who is the, you know, one of the editors of the Financial Times, and he got very close to winning and he was like, well, wait, isn't this just a really bad game? I was like, look, I set it up. If you had to choose your positions and so forth, it wouldn't have gotten this way. Yes, the rules happen to play out in a way that it was favoring you to me. And so it makes you think the game's only luck. But actually, in fact, there's a lot of things that play into this. How do you maneuver luck? Which is one of the things I like about Sellers. So anyway, back to the discovery was a friend of mine, Tom Todaro, who I worked together with at PayPal and done other things with, who was like, well, have you ever played Zettlers of Katana? I was like, no, never even heard what it was. And it was like, well, you should do this. So this is a much later in life game. I'd actually already at that point been decades away from having played board games and of course got slaughtered. The first, you know, five to 10 games that I played, you know, is one of the things, you know, another good learning moment, these things is learning how to do them and so forth. And the reason why I then became a propagator of the game, not just playing with Tom and, you know, kind of the people he was playing with and our mutual friends, but also Teaching other people is that I decided that Settlers of Catan was the closest game to the entrepreneurship side. And the reasons are because it's a resource and building generation game where there's probability on that. But then most centrally, there's a trading mechanic. And part of that trading mechanic is like, hey, we're trading. And you know, it's this kind of funny thing where each person's doing a trade because they think it's closer to have them winning. The one thing that's really not entrepreneurial about settlers at Catan is that there's one winner. And so, you know, the notion of, like, settlers would be more naturally if there was first place, second place, third place, fourth place, and that was the way you were doing it. Because then, by the way, everyone would still continue to trade because they would go, well, it matters the difference if I'm third place or fourth place versus, you know, only first place. Right. But within that mechanic, the trading mechanic is part of the thing that makes settlers a lot of fun, because it's like, no, no, don't trade with them. Trade with me. And this is why you want to trade with me. And this is why it helps you. And, you know, this is a little bit of the don't trade with them, you know, that person because they're in first place, et cetera. And that dynamic is, I think, very central to the entire, like, you know, no, entrepreneurship happens by itself. It's which investors you're working with, which customers you're working with, which supply chain you're working with, which people are you hiring, which platforms are you building with, and on and so forth. And so all of that kind of played into it. And then along lines of adding trading to this whole dynamic of the fact that you need to shift your strategy regarding to how probability plays out, because you might have started with a, hey, look, I've chosen my positions well in the following kinds of probabilities. I think the probabilities are likely going to end up in this particular kind of way. And so therefore, I've got a good initial plan, but, oh, gosh, these numbers have enrolled a lot. How do I alter my strategy? And fortunately, because one of the things that's interesting and good about Settlers of Catan is that, like, there's one winning condition, but there's a multiple paths for getting there, and you could shift to an alternative path for getting there. Like, you know, for those settlers at Catan geeks in the audience, it's like the discovery card strategy and so forth. And so that's part of the reason why, like, I've been a huge fan of Settlers for now could be approaching two decades.

I think it is approaching two decades because PayPal goes all the way back to the late 1990s. So I do think it's two decades now. Now, one of the things that I found interesting in that discussion of Settlers, which again, this is probably something that is low class, you're not as familiar with. But on television, they have all these reality television shows. Actually, the technical term is unscripted because there's nothing real about them. But there are many of these which are structured as a bit of a competition where people are competing against each other in various ways. One such show was a show called the Apprentice that will talk about in a little bit. And the thing about the shows is they have these challenges, they have these things that you're supposed to do. But in many ways, the way to win is to win the social game. The ability to persuade people to be an ally and to take your side. And it's a constant thread that I think applies in the real world as well. We see this in the interaction of various companies in the corporate space stage. So I think that social game element of Settlers really comes through and is really one of the things that makes it special as well.

Yep. And I think that's again, part of the reason why your architecture for which games was like, yep, Settlers is a good penultimate game to talk about is because that dynamic of how you interact with other people who are also building things and you. The interaction isn't just, I'm trying to win and isn't just bluffing or anything else, but is a trading negotiation strategy is a very important part of business and life generally now.

You have become, in addition to a game player, a game producer. I know that there is a version of Settlers called Settlers of Silicon Valley that you've produced. And there's also another game which ties in with the Apprentice, which is the game trumped up cards. So why don't you talk a little bit about trumped up cards? And how did that come to be? How did that become something that you've now produced? Not just trumped up cards, but various.

Expansion packs for the mechanic behind trumped up cards is a kind of a classic mechanic. Apples, apples, cards against humanity, et cetera. And cards against humanity made me realize that there's a really fun thing in a game playing circumstance to share perspectives on something difficult, something absurd, et cetera. And I went, ooh, this is a really good idea of reusing this mechanic on his own. And so when Trump started his candidacy in 2016, I was like, look, this is so absurd. What I will do is I will make this card game, basically as a gift for my friends, is to kind of highlight the absurdity. And so you could have a little, hey, we're playing this kind of fun little mechanical card game. But we could be in a way that illustrates the various things about Trump. Like, you know, he's actually never done anything public service or philanthropic. He's actually terrible at governance. Like, as a business person, he's one of the very few business people who can drive a casino into bankruptcy. You know, he brands a lot and so forth. And the most successful thing he's ever done is the Apprentice. By the way, super good at it. He's 11 out of 10 on that is like, I know how to do sound bites and attract to audiences, and if I'm not constrained by speaking truth, I can tune to what people want to hear and say that in very vigorous ways, which unfortunately made him a good campaigner for politics. So initially it was just like, hey, let's have a card game to highlight the absurdity. And then, of course, as he won the Republican primary and then the presidency, it was like, okay, well, let's. As opposed to just doing this as a gift for my friends, let me also make it available to the world at large. Because that statement of this absurdity needs to not just be made privately, but actually publicly. And so the idea is to have, like, when people encounter it, like, there's some descriptions about, like, well, like, well, that can't be on this card. It's like, well, no, actually, in fact, here is the fact that that underlies this card. That has to do with Trump and his claims that he's a great businessman and a great deal maker and a great candidate or a great president. And why, in fact, all of that is absurd.

Well, I can tell you it's funny. Obviously, you're known for a lot of things, but when I was actually shooting that television show Mental Samurai, one of the people who was there, all these competitors or avid game players, one of the people was saying, you know what is my favorite favorite game in the world? It's this game called Trumped Up Cards. And when I told them that I knew the guy who produced it, they were so excited. It was astonishing. Probably one of the only times that somebody's been really excited to hear about my friend Reid Hoffman because they played his card game.

Well, I remember when you relayed that story, and that was A shared delight.

Yes. So as we look back over these games, one of the things that struck me is A, it's been instrumental in shaping your worldview, shaping you as a strategist, shaping your approach to entrepreneurship, investing and all these other things. But B, what's interesting is there's this period of time, like you said, for a couple of decades you didn't play these games and now you've come back with a vengeance, even creating these games. What do you think caused that interregnum and where do you see games and their role in your life in the future?

Well, so a little bit of like creating the trumped up cards is that the benefit of these kinds of games is that there are ways that which we can spend time together in a fun way and then learn. You might learn strategy and tactics, you might learn about each other. I mean, one of the games we didn't talk about, because I think this is a different kind of learning, not the strategy and tactics applied to business, but Trivial Pursuit was a phenomena in its time. And actually, in fact, these kinds of games are useful in how do we not just learn strategy and tactics, but also about ourselves, about each other, about discussion, about negotiation. You know, hence the Settlers of Catan and the knockoff, which I don't sell because I want everyone to buy a copy of Settlers of Catan. If you've already bought a copy of Settlers of Catan and I know you, then I'm willing to give you a copy of, you know, Startups of Silicon Valley. But the pattern of this is learning these things together and doing it in a fun way. And I think that's part of the reason why I've started thinking again about, I wonder what other games design might be and who knows if I'll get enough time to it. I have some ideas, but all of these things are a triage on time and we'll see if that comes about.

Well, I think that that is about as good a summary as we could hope for. It's a way for people to learn, but to learn together. And as you've said many times, all of life, especially entrepreneurship, is a team sport, not an individual sport. And I think that these games definitely reflect that 100% well, since you are fully vaccinated and I am getting there, I will look forward to a point in time this year when we will get together and play games in person.

I look forward to that as well.

Well, 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 and of course, you can follow Greylock on Twitter reylockvc. I'm Chris Yeh. On behalf of Reid Hoffman, thank you for listening.