How to Win by Daniel Gross

Geoff Ralston:
The next speaker, Daniel Gross, is a former YC founder, and YC partner, and he  is going to tell you some really important things about staying sane and healthy and  whole while you’re doing this incredibly hard thing that is being a startup founder. So,  Daniel. 
Daniel Gross:
Thank you. Thank you, Jeff. Alright, hello. Sorry, we’re running a little behind today. It’s  my fault. If any of you are working on curing traffic, I suggest you get  to it a little bit faster. So this was the original title of the talk.  In hindsight, it’s kind of a terrible title, so we’re gonna remove it. This is  actually what I want to talk about today. I think everyone here, fundamentally, is playing  a game, and you want to win that game. Whatever project you’re working on, I’m  sure people here are excited to build the next empire, become the next Rockefellers. And  one kind of view here that I’ve noticed over years of working with different startup  founders, being a startup founder myself is, when you’re a founder, the mentality you get  into is kind of like you’re an athlete. And startups are kind of the Olympics.  It’s one of the hardest things you can do. And what I’d like to do  in this talk today is go over some of the mistakes some novice athletes make  while they’re trying to play in the Olympics, because I do think they’re kind of  repeated. And over the course of the past few weeks, I think you guys have  seen great talks on mistakes people make, say, when marketing, or hiring, or growing your  company. But there’s a lot of mistakes you make with yourself. And I’d like to  help you potentially avoid them. A lot of the mistakes stem from this recurring theme,  which is, you’re working really hard, and not smart. Kind of like this guy, with  the rickshaw. You don’t want to be in this position. Examples of things that will  be in your head if you start a company, especially as you start growing out  a team, are I’m gonna be in the office all the time. Or I will  make sure to be the last one out today. I will work as hard as  I can. And while there’s a lot of value in it, that stuff could kind  of go wrong, because ultimately, input doesn’t equal output. Founders seem to make this mistake  over and over again, and what they forget is, nobody wants to work for a  tired idiot. It’s actually incredibly uninspiring. And so, ultimately, if we were to do a  little quick Harvard two by two metrics here, if you just … This is the  most common startup founder mistake, where you just focus on, I’m gonna pedal the bike  as hard as possible, and you don’t really get anywhere. That’s kind of bad, too.  I would not want the outcome of this talk to be the other extreme, which  is maybe, you could define academia and get really smart, but you’re not pedaling as  hard. What you really want is to be doing both. And so, we’re gonna be  talking a little bit today on how to do that. Before we dig into any  details, I thought it should be interesting to maybe quickly go over why this even  happens as a problem. So out of curiosity, if you’ve ever worked for someone before  that you respected, a manager you respected, please raise your hand. Okay, so about half  the room. Ultimately, when you’re a founder, you kind of want to win the approval  of your pack, be it your team, or other founders. And the problem is, a  lot of first time founders don’t really have that experience of what that thing you  want to look up to is. So they don’t have a mental model for what  to emulate. And as a result, there’s just a lot of common mistakes people make,  because they don’t know kind of what greatness looks like, and so they optimize for  the wrong thing. Alright, so that should set, hopefully, the general framing for the talk.  What does this actually mean in practice? So we’re gonna go over a couple of  different areas. Common mistake with sleep, food, exercise, your mind, and leadership. This is kind  of a Maslow’s hierarchy of sorts to startup success, where I think you can only  tackle the stuff at the bottom after you tackle the basics. What’s really ironic about  the advice I’m about to deliver you, is I’m sure for about half the people  in this room, and I’m sure many more people online, you will make all these  mistakes despite me saying what I’m about to say. It’s kind of fascinating, but I’ll  go through the exercise anyway, just so I can tell you I told you so.  Alright, so sleep. Guys, the reviews are in. Sleep is the ultimate nootropic. It just  takes a couple of hours to apply. There is no way that cutting that hour  of sleep was actually worth it for your company, unless there’s a real emergency. Some  people need five hours of sleep, some people need eight hours of sleep, some people  need nine. Just sleep as much as you need. When I started my first company,  I was very focused on, as I mentioned earlier, just being in the office all  the time, working as hard as possible, and again, it’s really stupid, and in fact,  bad for your shareholders and for your entire company if you’re coming in there with  20% cognition ’cause you’re not sleeping well. I would spend a bunch of weekend time,  you don’t have to spend your company time on this, optimizing your sleep environment. I  think sleep masks are the most underrated product in the world, in terms of the  upside that they give you and the cost is like $20. I sleep significantly better.  There’s a website for this that details it. I would just go through all their  products. I would be incredibly frugal in general in life, and I would spend lavishly  on this one. Again, just think about it as a nootropic. I know there’s a  lot of people that are obsessed with kind of taking l’theanine, or caffeine. This is  a far better nootropic than all that stuff. So just spend on it. I would  try to avoid using an alarm clock, at least for half the week. Again, your  ancestors didn’t have an alarm clock. They survived, you should be able to as well.  Sometimes, one thing your ancestors obviously were not exposed to is a lot of light  in the night, and so occasionally, resetting your circadian rhythm, I think for a lot  of folks, especially software engineers, can be helpful. I think if you’re a software engineer,  you probably have … Well, I found at least, most software engineers that I’ve worked  with have about a 25 hour cycle. That is to say, they increasingly wake up  later and later and later. If you take a little bit of melatonin, you can  actually reset that quite well. For various fascinating regulation reasons, most melatonin sold in the  United States is way much more than you need. It’s like three, five, or ten  milligrams. Your body makes point three when it wants to put you to bed, so  that’s what you should take. You literally have to buy this on Amazon, the reasons  for which are fascinating, but outside of the context of this talk. Okay, so we  discussed sleep a little bit. That should be real basic. I don’t think you should  tackle anything else before you’re sleeping well. It’s, again, fascinating. I’m sure most of you,  some of you will follow this advice. A lot of you will continue doing what  you’re doing. But again, I told you so. Alright, let’s talk about food. Okay, so  again, just think of what you’re doing and what you want your team to be.  Garbage food impairs your judgment. I, at some point, realized I was letting everyone else  down on my team if I was not playing at peak performance, if I was  not treating myself like an athlete. So I would not eat crap food. I really  don’t want to go down the rabbit hole of what diets to do. I’m not  a dietician, and I’m not here to be your Tony Robbins, but I would just  focus on whatever you think is healthy. I actually think there’s probably a lot of  psychological benefit to just eating whatever you think is healthy. Frankly, if you believe sugar  is really healthy for you, if you really believe that, maybe that’s fine. Whatever fad  you’re into, just go for it. This is something worth investing in. This is a  contentious topic, but I think it is immoral to have junk food, weaponized junk food,  in your office. I would just get rid of all of it, and focus on  healthy food. You can find healthy foods just as cheap. I also think everyone is  dehydrated all the time. I would try to drink an uncomfortable amount of water. This  is probably the only weird hack I’m gonna give you in this talk. Most of  it’s gonna be frameworks. But practically speaking, yes, you got it. This man is set  up for success. I just think you’ll feel much better if you do. Alright, so  that’s a little bit about food. Again, I think it’s pretty simple. The message here,  the repeated message here is invest in yourself, because startups are one of the most  draining things you can do to your body, to your mind. Let’s talk about exercise.  Okay, this is probably a good idea. Again, just like sleep, the results are pretty  conclusive on this one. One thing I always … Well, taking a step back. If  you don’t exercise, I would at least try to spend a lot of time outdoors.  If you have a team, you can start having one on ones outdoors if you’re  managing that team. If you’re somewhere terribly cold where you can’t spend time outdoors, that  sucks, but well, maybe you should move to somewhere that has more sun. I would  always picture in my mind, ’cause I’m an overly competitive person, that whoever my competitor  was, they were probably working out like four times a week, becoming better, having better  ideas, becoming more creative. If that framing is helpful for you, I would use it.  I don’t mean to be overly prescriptive on what you do. I think anything you  do in the spirit of exercise is good. I don’t have to cite, I can’t,  I don’t have time to cite all the studies that correlate with this. I do  think running is probably the best, in terms of time expenditure to potential reward, if  you can do it. And I think the more interesting question with exercise is not  whether you should do it, ’cause I think it’s pretty clear to everyone on the  planet you should do it, but how to convince yourself to do it, because that’s  the harder psychological bit. The largest mistake I think people make, especially if you’re a  founder of a company, is you have a like, I’m gonna go all in mentality.  You tend to go all into things. If you go all into something like running  the first time, you’re gonna hate it, ’cause you’re gonna sprint. Sprinting sucks. So I  would not overdo it, and I would start really small, and build positive memories you  can grow on. So celebrate success. What you want to do is, pretty much for  everything, but in this particular thing, the trick is to create a positive memory such  that when your brain predicts whether you do that activity the next time, it look  back and thinks, yeah, that was kind of fun. So that may mean running a  mile, and then getting a frappuccino. Just because, what you’ll remember is getting the frappuccino.  But try to really trick yourself into doing this. It’ll definitely pay off. I think  the other thing you can do in order to kind of reduce to willpower required  to do anything is, surround yourself by other people that are doing it. You can  tell other people that you’re running, which is great, ’cause then you’ll kind of feel  like you have to do it, ’cause you told everyone about it. You could surround  yourself with other people that are running. For me, especially through the dark phases of  my startup, this was definitely my light. It helps you relax, it helps you focus,  and you guys are gonna go through a lot of ups and downs. I suggest  setting up these good habits while you’re either at a plateau, or at an up,  because it’s really hard to convince yourself to do anything while you’re down. But if  you set up the mental habit, it’s a little bit easier to come back to.  Alright, so if you got down the basics, you’re sleeping well, you’re eating well, you’re  exercising, then we can start to talk about the more interesting things you could do  and you should be doing to transform yourself as a leader and to really take  your company to the next level. There are a bunch of kind of subcategories within  how to think about optimizing your mind. The largest mistake people make, I think, in  terms of just thinking better, is they focus a lot on feeding their body, and  then they don’t focus on feeding their brain. But ultimately, your brain, I think, is  just constantly doing pattern recognition, and the pattern recognition that it’s doing is very much  powered by the information it’s consumed. And so, you really want to focus on feeding  your mind like you’re feeding your body. What does that mean? In practice, I would  spend at least one day a week not working as hard as you can. And  your goal here is, by as hard as you can, I mean, you want to  do whatever activity will help you feel the most refreshed when you come back to  work. And there’s all sorts of interesting studies of spending time in nature is really  good for this, maybe going to the beach, whatever. I don’t intend to be prescriptive,  but you really need to spend a day a week not working. This is really  helpful, because when you come back to work, you will have … Your brain will  just be different, and it’ll be solving problems in a more novel way, and let  me frame it this way. Your competitors are probably doing this, and they’re coming up  with better answers than you are. So you should definitely take a sabbath. I mean,  it blows my mind that people don’t do this. It’s, I guess, a separation of  the urgent and the important that people struggle to do. I would focus a lot  on reading long form. I think a mistake people make here is, everyone talks about  reading a lot, and people get very obsessed with reading is a thing to do.  The greatest gift someone gave me is this idea of not really caring about what  you read, whether you even finish the book, just trying to read any book, any  time, all the time, every day. Because I, and I think this is common amongst  founders. You get obsessed in this mindset of, I gotta do it, I gotta finish  the book. You get stuck in a crappy book, you stop reading altogether, and now  you’re on Instagram. It sucks. So just pick anything. Continually try to read it. I  find that the value that books give you, they’re not just informational, they actually set  up your mind in a particular way. If you read a biography about a person,  you’ll find yourself thinking a little bit more like that person thought, or like you  read that person thought. And I think that afterglow is really what you’re trying to  get. And I don’t think you can get that from short form content. I would  sign out of all, unless your business is tied to it, in which case, good  luck. I would sign out of all this crap on your phone, and just make  it a little bit harder to use. Yeah. It’s just too good is the main  problem. This is just way too good. Alright, so that’s in terms of how you  should feed your brain. In terms of how you should think, like the software that’s  running in your head, probably the largest thing you want to do is you want  to move from this mode, where you’re playing first person, to this mode, where you’re  playing third person. And what do I mean by that? I mean by that, it’s  a little bit less I’m angry, and a little bit more, I’m feeling anger. The  other term people use for this mindfulness. I’m trying to avoid that and repackage it  in terms that seem a little bit more exciting. But it’s building the habit of  kind of stepping out of the frame, and experiencing yourself almost in the third person.  This is really useful, because … Well, it’s actually not that useful if things go  really well, in which case all of your emotions are awesome. But when things start  going south, it’s gonna become really important. It’s gonna become also important when you start  doing bad things that are mostly a byproduct of your own insecurities. So someone, say,  who reports to you, says something disagreeable to you in a meeting, and it’s quite  helpful to be able to step back and say, what’s happening now is, I feel  insecure, as opposed to, I’m dumb. Which is what actually happens if you’re playing in  first person. You’ll be able to react better, you’ll be able to lead people better.  In terms of how to do it, meditation is one way to achieve this. There’s  a lot of studies that show that it just happens as a byproduct of being  in your mind for more years. So just growing up. But I actually think the  most valuable way to get better at this is to just think about it, is  just have the concept in your head. But it is probably the largest, most important  mental shift I think you can do as a founder, because you’re putting yourself through  an emotional rollercoaster. So that’s kind of a large software shift that I think is  really, really important. In terms of other cheap hacks that relate to your mind, I  think the simplest goal that you should constantly be thinking about is how to spend  as much of your day in flow as possible. Flow is this concept of basically  becoming unaware of how time passes. There’s a book written by a gentleman whose last  name I can’t pronounce, so I’m not even gonna bother. McHail something, about this topic  that I recommend reading. You want to spend as much of your time in flow  as possible, and if you’re really good as a manager, you really want to spend  your entire team’s day in flow as much as possible. People should be moving from  one thing to the next, to the next, to the next, not even really noticing  time fly by. And that is, I don’t have any instant solutions to that, but  you may be kind of noticing a theme across the talk here, which is the  key is to kind of launch and iterate. I would be constantly asking yourself, what  time of day is the best for you to do meeting? What time of day  is best for the team to do meetings? What music makes you productive? Is the  person you’re going to put on a particular project, are they gonna enjoy that? Does  that match their personality? Maybe yes, maybe no. So you need constantly be in this  framework of trying different things and iterating. Don’t be on autopilot. There’s a lot of  information. Data laying on the ground, that comes out of an emission from whatever you  did, by putting a meeting super early in the morning, super late in the day,  bunching meetings together, keeping them separate. I don’t mean to be prescriptive, because I actually  don’t know that there is a global answer, but there’s definitely and individualized one to  you. And the really great people are constantly iterating on whatever that is, trying to  improve themselves. So you should do that, ’cause the competition is doing that. The last  thing I want to talk about is, probably the most important one of you as  you build out a team, which is how to become a really good, really inspiring  leader. There’s a lot of different books on leadership, there’s a lot of different studies  on it. Most of them are garbage. There’s one particularly good one that I’d like  to walk you guys through, which is Robert Keegan’s theory of adult development. Robert Keegan  is a psychologist that has done a lot of work on adult development, distinct from  child development, which folks like [Piashay] have covered quite well. There’s not that much literature  on how adults, say, circa 18 and beyond evolve in terms of their thinking and  thought patterns. And what he’s done is he’s kind of split out five different phases  that people tend to go through throughout life, and not all people make it to  the final two phases. We’re really gonna focus here on stage two through five, since  one is basically really children. And I’m gonna walk you through them, and then we’ll  talk a little bit about how you can kind of advance from one phase to  the next. So let’s talk a little bit about an imperial mind. You can kind  of think of this as a very simple AI. This is someone who is, for  the most part, these are children, but I think we all know some adults that  fit this bill. This is someone who is incredibly selfish, so they’re very focused on  their own goals. That’s the number one most important thing for them. They’re transactional, so  the relationship with other people is really just a way for them to get a  thing done that they want. The view of the other side is untenable to them.  So, oh, what do you think of person that brings up other ideas? Can’t even  get there. Can’t even see how that person would have that view. The challenge with  this mode is that, it’s really hard to get people to cooperate with you over  the long term. As you guys grow teams, you may start seeing this flaw in  some managers. It becomes very easy to see actually when it’s not you, but through  someone else where, people over time are just not interested in working for them or  don’t find them compelling. So this is kind of the most embryonic phase you can  be in as an adult, which I think has some obviously limitations. Once you advance  beyond stage two, you get to stage three, the socialized mind, or as I call  it, the NPC. The non-playable character in the game. This is most adults, and these  are people who are kind of able to see the other side, but they almost  see it too well. And in that sense, they’re kind of NPCs. They have no  internal locust of control. They really care about what other people are thinking about them  all the time, and the social narrative of, oh, people think I’m dumb, becomes their  narrative, therefore, I’m dumb, if that makes sense. So you’ve kind of pendulum swung a  little bit too far, where instead of not caring really about what other people think,  you now are entirely driven by it. Occasionally, we’ll see founders that are kind of  in this mode. It’s just really hard to have an independent mindset when you’re in  this mode, and any great company, as you guys know, that faces a lot of  unknowns, and you have to be able to stare in the abyss and say, there’s  a light at the end of the tunnel. And it’s really hard to do that  if you’re constantly gut checking yourself about what other people think about you. There’s some  value here. The opinion of other people is actually important. It’s a great way to  know if you’re doing something right or wrong. The problem with people in this mindset  is they’re just unable to have their own framework for how to live life, or  their own truly independent ideals. Once you evolve beyond that, you reach the kind of  master player phase, or the self authoring phase. And this is, in Keegan’s view, some  adults. You have less motivation by social affirmation, and you have a kind of consistent,  independent frame of mind. So you have certain values, certain ideals, certain things you hold  yourself by, and you can identify with them, and you know what those are. I  am a person who cares a lot about X. And that’s a part of the  inner monologue in your mind. Importantly, you’re able to take responsibility for your own emotions.  So this comes back to that point of playing in the third person. I’m feeling  angry at you because you said, you kind of assaulted a value I hold dearly.  So you kind of know who you are at this phase. This may actually be  the best phase for a founder. Because you have very clear ideals that you hold  onto, you kind of know who you are, you’re aware of your emotions, and it’s  slightly different from that second phase we were talking about moments ago. You’re able to  kind of play an infinite game with people, where you’re optimizing for the collective group,  not just for yourself. But you do have kind of a sense of where you  stand. There is another phase beyond it, and Keegan’s interesting claim here is that very  few adults make this phase. The kind of self transforming mind. And if previously, we  were talking about a really competent game player, this would be almost a game designer.  This is someone who is not really held back by any sense of who they  are as a person, and what values and ideals they have, and is able to  basically embrace and extend any of the opinions and ideas of people around him. So  they’re constantly being recreated by the group that they’re in, if that makes sense. You  could almost, an engineering metaphor would be that this person can kind of run any  idea that comes to them in VM. They can properly evaluate it. They’re genuinely curious  and interested in other people, they’re willing to drop an entire ideology and swap it  for another one in moments, if it makes sense for them. And unlike that second  phase, it’s not being driven by what will other people think, it’s truly being driven  by the quality of that idea and ideology. The other very interesting thing about these  people that I find fascinating is, the tendency to think in systems. So when someone  is bringing up an idea, being able to very quickly realize, oh, they’re bringing up  that idea because of X, Y, and Z, because that’s their position in the organization,  or that’s their background, or that’s the environment they grew up in. It’s almost like  you’re seeing the entire map, or you’re on the 100th floor of the building, and  you’re seeing the entire city unfold underneath you, as opposed to being on the first  floor. They make the interesting case that this is the vision, this is where you  want to get to. It’s actually not clear to me for founders that you want  to be here until you have product market fit. There’s something very interesting about these  people, which is, they’re generally, I find, they’re very good at managing very high quality  talent, who needs to be properly heard, needs to be properly understood in order to  be inspired to come into work every day. But danger of making metaphors, but when  you think of Elon or Steve Jobs, it’s not clear that you end up here.  It’s a little bit more stage four. They have an idea, and they’re just gonna  railroad it through. But I think it’s an interesting thing to hold onto long term,  and I definitely think that as you guys grow, and as your companies, you start  building out a strong executive bench, this is actually what’s required to get players to  be interested in working for you. You have to really be able to set up  an environment where they can live their own ideology, and they feel challenged by you,  and they feel like you’re willing to adopt it, and you can actually put together  people with very different ideologies and kind of get them to mesh together. It’s like  you’re designing the game, as opposed to being an individual player. So the question is,  okay, given where one is, and there’s a case to be made that we can’t  really ever evaluate where we stand on this kind of thing. How do you move  on to the next phase? How do you become less maybe self centered, and more  focused intrinsically in motivating others to join your cause? I think knowing the concepts actually  can really help, ’cause then you can kind of label some thoughts that you have  and say, well, that’s stage two, not five. And if you guys are interested in  this, you should just Google Bob Keegan and read any of his books. Time, according  to him, just kind of moves a person along a continuum here. There’s, of course,  this question of derivative, how quickly you’re moving. One very practical thing that I’ve learned  to do over the age, over the limited amount of time I’ve had on this  planet is, when interacting with people, especially people that you hire, I would only try  to ask questions you’re generally interested in hearing the answer of. It’s kind of interesting,  especially in interviews, to hear people ask these rogue questions they don’t really care about,  because that’s the conventional question to ask, and then they don’t really listen to the  answer, and then they’re not really having a good interaction with the person. So try  to nerd snipe yourself with this idea of, what would be the most fascinating question  to ask this person now? Even if it’s someone who is saying something that you  drastically disagree with. It’s an interesting brainstorm of, what is something they would say that  would cause me to change my opinion? That will just make, I think, life more  interesting for you, and maybe help you kind of work through that continuum. So that’s  a little bit on leadership. A lot of this, especially if this is the first  time leading a team, a lot of this is stuff that you’ll just figure out  as you go along. I do think it’s helpful, a little bit, to have these  concepts in your mind, in terms of what’s good and what’s bad and where you  want to be. Okay. So I want to give you guys some closing thoughts. I  think it’s really important that you, that the metaphor of the Olympics wasn’t me kidding  around. I remember when I did YCombinator in winter 2010, James Lindenbaum, the CEO and  founder of Heroku came by, and he gave a talk. And he said, a related  flavor of this, which is he said that you should bill yourself at 500 dollars  an hour. Which, at the time, seemed insane to me, until I found out that,  of course, that my lawyer was billing me at 750 an hour. But the point  is, your time is really precious, and especially as your team grows, you will be  increasing the choke point for getting things done. And so, you really have to treat  yourself as an athlete if you want to survive this game, ’cause all of the  responsibility is on your shoulders. And you cannot cave. You cannot cave and go for  the urgent instead of the important. It’s just not acceptable. If it’s helpful, I would  just assume that the others have figured this out, and they’re ahead of you, and  you just need to catch up to them. So you just assume that they’re well  rested, they’re eating properly, they’re thinking properly, so when you find you’re … I certainly  had nights when I was running my company where I found myself at the office,  three o’clock in the morning, eating Skittles. This is not a good scene. This idea  of switching to third party camera mode, and experiencing yourself in the third person is  really important. You guys are gonna have days, months, weeks, where you get punched in  the face a lot. Like someone wants to quit, and you lose a customer, and  things aren’t growing. The only way to survive that, and when you’re in that mode,  still play all the right chess moves, is to experience your emotions in the third  person. Otherwise, you get caught up in it, and it’s just lame, honestly. So I  spend a lot of time thinking about that. The particulars of any hack don’t really  matter. I don’t care if you don’t actually drink water. The key thing here is  to launch and iterate yourself, kind of. You have a lot of data going on  about what’s good, what’s bad, what days make you feel good, what days make you  feel bad. And just collect that information, and retrain your model, over and over and  over. I would very much try to just be genuinely curious of other people. I  think if you are, you’ll find out, other people are just the most interesting thing  on the planet. Far more so than VI, or whatever engineering problem you’re solving. It’s  far more dynamic than a computer. And if you get really interested in what drives  other people, what motivates them, you’ll get really good at recruiting other people, you’ll get  really good at motivating other people, but you have to really treat it as a  system that you’re genuinely interested in. Always try to ask compelling questions of other people.  Don’t bore them, don’t bore yourself. The last thing is a concept that’s a little  bit hard to convey, but was one of the most helpful shifts I went through,  which is, you want to move from playing very finite games in life to infinite  games. And what I mean by that is, ten thousand different things, but I guess  at a high level, you have … I think when you get started, you tend  to get very worried in various interactions that you have with people that it’s zero  sum. That it’s a win lose situation. Maybe there’s an idea you have, but you’re  not sure if you should share it with someone, ’cause maybe if you give it  to them, then they’ll go out and run with it, and then they’ll steal all  the credit, and you’ll be the [Winkelvoss] and they’ll be Mark Zuckerberg or something. And  it’s really important to let those thoughts go. You very much want to make believe  you’re playing an infinite game that doesn’t really have an end. The scoreboard is really  unclear, and you’re just trying to engender as much good will as you want. There’s  a great book on this topic called Finite and Infinite Games, that helps set this  kind of mental frame. Because it’s very hard to explain in words, but … Whoa.  Someone’s playing Mario. But you want to, I guess, move a little bit from being  focused on winning one particular interaction, to winning the overall set of interactions. Said differently,  you’re running a marathon, you’re not sprinting. So that’s it. So that’s a little bit  of a rant, hopefully a semi-productive rant, on what you need to be doing in  order to kind of improve yourself, in order to advance to the next level. And  at the very least, should be a good overview of some incredibly common startup mistakes  people make. To the 50% of you that actually follow this advice and avoid those  mistakes, awesome. And to the 50% that don’t, or probably 90% that don’t, I told  you so. Thank you so much. You want to … Sorry? 
Geoff Ralston:
Want to do a Q&A? 
Daniel Gross:
Q&A, yes. Sure. 
Speaker 3:
Do you have any experience with people who left a comfortable position at the corporation,  and then having to deal with ups and downs [inaudible] ? 
Geoff Ralston:
Can you please repeat the question? 
Daniel Gross:
Yeah, so the question was, for people that leave comfortable corporate positions, how they handle  the rollercoaster of a startup. I think … Yeah, so occasionally, you see founders who  … There’s basically two reactions to this. If you leave your kind of great job  at Google, and you go join a startup rollercoaster. One reaction is, a version, effectively.  Oh, I don’t want to deal with that, not focus on it, or I got  very used to having, taking an extra day off on the weekend, so I’m just  not gonna give that up. Those companies, sadly, don’t do well. And I think those  people are unhappy in the process while they’re doing it. Startups are ultimately, you’re playing  on expert mode, and it only makes sense if you’re gonna commit. A lot of  other people, I think most founders that we’ve worked with, humans are resilient. And so  you kind of figure it out. I think the real take on it is not  whether the person got too comfortable. It’s really like, are they innately interested in working  on the problem they’re working on? That’s what I think is going on with a  lot of those people, is they leave a Google to start a company because they  feel like they should start a company, as opposed to really being interested in making  something, if that makes sense. So that’s the thing I would focus on. Because if  you’re really interested in something, of course you’ll spend all day thinking about it. Sure. 
Speaker 4:
If you’re trying to minimize the amount of time you spend online, but your business  forces you to go on Facebook or Instagram or Twitter for whatever reason, how do  you recommend mitigating that problem, or dealing with the mental health effects of that? 
Daniel Gross:
Okay, so the question is, if you business kind of demands of you to be  online, how do you handle falling into the simple maximizer trap. One very funny thing  we used to do in my company is, we all had our monitors facing each  other, if that makes sense, and so there was kind of a circle. And there’s  a weird accountability that gets enforced when you do that. Of course, no one is  actually watching your monitor, they’re busy doing your own work. But you have a little  voice in your head that’s saying, maybe they are. So that’s a fun hack that  I think works quite well, kind of team enforceability. I think the other solution to  this is not really tackling that problem, but really focusing on something else, which is  growing as quickly as possible. And if you do, this will just have to be  a demon you slay in the process of growing as quickly as possible, ’cause you  cannot grow if you’re watching YouTube. Unless you’re watching your own videos. Yeah? 
Speaker 5:
Hi. I was wondering, what’s your personal mantra about startup life? Elon Musk says that  launching a company is, well, he had a friend that said, eating- 
Daniel Gross:
Chewing glass and staring into the abyss? 
Speaker 5:
Yes. And my personal line is, it’s an involuntary vow of poverty that requires a  zen-like state of mind. What’s yours? 
Daniel Gross:
Okay, so the question is, what’s my mantra regarding startups. I don’t know that I’m  smart enough to have a mantra about it. But probably if I were to have  one, it would be something akin to what I mentioned earlier. It’s like playing a  video game on expert mode, where the video game is really managing your own psychology  and trying to build a product that works. I do think we shouldn’t frame this  as something that is painful. I think there are a phenomenal amount of ups that  go with the downs, and for every Elon Musk quote where he’s chewing glass and  staring into the abyss, he also gets to see his roadster in space. That’s pretty  good. So yeah. So I think it’s just, I mean, you have to really enjoy  building stuff, ultimately. Yes? 
Speaker 6:
Thank you very much, Daniel. This has been fantastic. I really like how this sets  up a system of poor self alliance, and identifies [inaudible] . But I’ve also set  up some mentorship and communities to support myself. Is there something you would talk to  about how you found community, or creating something to support you as you fought through,  and what’s worked and what hasn’t? 
Daniel Gross:
Well this is … Okay, so the question is, strategies around building community and peers  in order to kind of help yourself become better. This is, actually, I think, one  of the main benefits of startup school, and assuredly, one of the main benefits of  YC, is that you get put in a peer group with other people. And what  happens is, you very quickly figure out, humans are fascinating. They subconsciously almost figure out,  where am I in the peer group, who is next to me, who is ahead  of me on the leaderboard, who is beneath me, where do I stand, and how  can I advance myself? I think this is also one of the reasons why Ivy  League campuses are so good. It’s not really the curriculum of the Ivy League. It’s  the fact that you’re suddenly surrounded by peers who are motivating you to be better.  So startup school is, I think, one very interesting way of scalably trying to give  that to as many people as possible on the internet, because we know that when  you’re kind of with relative peers, you’re always trying to figure out how to improve  yourself. Yeah, so doing startup school is one answer to your question. To me, the  largest value of YC is, I was suddenly challenged by the fact that I thought  other people in my batch were really darn good, and I kind of realized I  could compete on the same playing field. So I’d encourage you guys to apply to  YC, and also figure out other … I don’t know if there are other online  communities where you can kind of have that same sense of competing on the leaderboard.  Okay. All the way back. 
Speaker 7:
Kind of going off of that note, when you’re in an environment like this, it  seems like everyone is really great at doing the exact opposite of what you just  talked about. But it seems to land some pretty good results. How do you counter  that [inaudible] ? 
Daniel Gross:
So the question is, how do I counter the proposed reality where people are doing  the opposite of this presentation, and achieving greatness. And I guess I would question the  premise. I’m not sure I agree with you. I’m pretty sure that any successful unicorn  founder that you meet today would kind of agree with what I said here, which  is, even if they were doing all this crap that I defined as a mistake,  they wish they hadn’t. So there’s one interesting, really interesting view, which is, this is  a necessary pain you have to go through. You wish you hadn’t, but it was  worthwhile. I’m not sure I buy that. Life doesn’t have to suck. And you don’t  have to make mistakes to be successful. Please. 
Speaker 8:
Hi Daniel, I’m [inaudible] . 
Daniel Gross:
Oh, that’s good to know. 
Speaker 8:
This is amazing. No, for sure. I was a founder that was working 120, 140  hours a week, for a social network, and then I realized, social doesn’t work. I  still have the mission. What would you recommend during, while you’re trying to think of  the next solution, next product? What would you recommend founders to do? It’s actually still  kind of [inaudible] , or do something else meanwhile? 
Daniel Gross:
So the question is, what’s kind of a good way of coming up with your  next product idea? 
Speaker 8:
Yeah. 
Daniel Gross:
Or pivot. You also mentioned in your question that you were working on … One  thing I wanna be clear to everyone here is, I’m not proposing you don’t work  hard. In order to win, you have to work hard. I’m proposing you don’t moronically  work hard, and not sleep. Because then, you’re gonna have to work much harder, even,  to catch up. But your question was how to come up with startup ideas. Okay,  I think the … So there’s a lot of great content on this topic. PG,  Paul Graham has probably written the best of it. I’m not gonna be able to  one up him. But I think the, a common mistake that comes to mind right  now, in terms of mistakes people make when they try to come up with startup  ideas is, they’re very focused on trying to come up with an idea in a  very limited amount of time. And it’s not clear to me that stuff works in  a pressure cooker. I think, to me, I’ve had my best ideas when I haven’t  had any kind of immediate goal, have to come up with an idea, and they  just start kind of coming to you. I have a Google doc of maybe a  thousand different ideas, of which I’ll build probably none. But, I think the point is,  it’s much easier to think of this when you’re not necessarily in a pressure cooker.  And I’d really question the fact of, maybe you don’t need a startup idea. One  of a very common mistake I see in a lot of YC applicants is, they’re  obsessed with starting a startup, which is actually not what you want to do. My  greatest hope when I have an idea today is that someone else will build it.  I have no interest in going through the whole startup thing. So if you don’t  have any great ideas, that’s not a problem, that’s not a bug or a flaw.  Yes? 
Speaker 9:
How do you get out of this pressure cooker, and how do you manage the  risk? What’s a good [inaudible] to think about risk? 
Daniel Gross:
So the question is, how do I get out of the pressure cooker, and how  do I manage risk. Two different questions, I think, if I understand the second one  properly. I think the best way to get out of the pressure cooker is, I  would just take a day a week, Saturday, and just, like I mentioned, not work.  Physically, go north of, if you live in San Francisco, go north of it and  walk in the woods for a while. That’s great. And I don’t think you need  much more than that. How do I think about managing risk? That’s a very big  question. Boy. I think a lot of it depends on … Well, I think a  very common mistake, maybe this will be somewhat novel or interesting. A common mistake people  make when managing risk is, they pattern match type one and type two decisions improperly.  That is to say, this is the Jeff Bezos framework of, you got your type  one decisions, where the cost of downside is catastrophic. Type two decisions where ultimately, if  you make the mistake, nothing bad happens. And I think a very common flaw is,  you think things are type one, when they’re in fact type two. And more often  than not, the right call is to just go for it, whatever the risky path  is. Because the downside scenario you’re imagining is a little bit too creative, probably. So  I’ve definitely found when I’ve taken the riskier approach, I definitely have been rewarded by  life, and I’ll probably continue saying that until suddenly I’ll just die because I decided  to jump out of an airplane. That was a bad idea. So maybe there’s a  survivorship bias problem. But more often than not, the riskier path is the right one.  One more question. Sure. Sorry. 
Speaker 10:
Let’s say you’re on board with all this, but the problem is that your co-founder  is not really that easily prioritizing this stuff. Can you talk about sort of co-founders  doing some prioritizing? 
Daniel Gross:
Sure, yeah. So the question is how to get your co-founders on board for doing  this stuff. And again, I should re-embellish. Doing this stuff doesn’t mean chilling. It means  not dying while you’re building your company. So I think a lot of it is  the framing. And I think if you’re not careful with the framing, it comes across  as, let’s bring the perks of Google into our startup life, which is a recipe  for disaster. It’s hard. This is a weird piece of advice, ’cause like I mentioned  three or four times, a lot of people refuse to, or are just unable to  accept it, and they need to fail and fall on their face before they retrain  the model. In general, though, I think this is a very interesting question. What to  do in situations where you disagree with your co-founders, especially if there’s no tiebreaker. Super  common problem. Another founder. Product decisions. What do you do when you disagree? One useful  hack I did for a while with my co-founder, ’cause we were great friends, best  friends in fact. But we used to have these bitter product disagreements. You can just  cycle through different months where people have responsibility on a particular area, and so you  can say, look, for the next six months, you’re running product. I may not agree  with you, you get to run product. And then six months afterwards, we’ll check in.  Maybe we’ll swap over. But just really defining time constrained areas where a person gets  ultimate ownership is one, I think, underrated solution to the co-founder disagreement problem. So hopefully  that’s somewhat useful. Alright. Thank you all for listening. Sorry we started late, and I’ll  be around here if you guys have any questions I can help answer.
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