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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.


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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