“Why I Don’t Believe in ‘Founder Mode” | Ask Dave Kashen

You've mentioned to me before that you don't believe in founder mode. Can you tell me more about that? Why do you not believe in it? So I guess you could answer it that way, or— Sure.

So, you know, Brian Chesky gave this talk at a YC event and he talked about founder mode and sort of how he had hired all these like senior execs and felt like he was supposed to delegate and let, you know, get out of the way and let them do the things and, you know, run with their ideas. And in some way it didn't work very well. And he realized that he needed to be in quote unquote founder mode, like back to the beginning where he was like really involved with the details. I think it was especially around product, but not only. And so that it was almost like there was this tide toward delegation. You know, it's like this polarization, right? Like, micromanagement is bad. You know, you should delegate. A good CEO— you know, founder has to become CEO. Good CEO delegates, hires a great team, gets out of the way, gets out of the weeds. And so in a way, I think he— what people liked about this speech was it gave them permission to like get back into the weeds, right? Like, oh, because, you know, there's times as a founder where you want to be in the details and you care and like you don't want to stay out of the details just because of this abstract idea that you shouldn't be in the details. And so I think it struck a chord because I think a lot of founders receive that same message that like as the company grows up, you're not supposed to be in the details. That's not a high leverage use of your time, and you're supposed to just, you know, be high level and delegate. And they— I think a lot of founders want to be in the details around certain aspects of the business. And so I feel like it was like this, um, permissioning to get back into the details. And, you know, it's like, it's like the pendulum just, you know, swings in both directions. So there was this polarity around delegate and let go. And then the issue I have with founder mode is it's like this, this— now it's the polarity the other way, you know, almost like that's the new dogma is that you should be in the weeds and in the details. And it, you know, sort of gave a lot of founders permission, I think, to, um, funny enough, like micromanage and overly— like, it is scary to delegate. I work with a lot of clients who, as they're scaling their startup, they recognize that they can't— you know, they're just taxed, like they're maxed. They don't— they can't get to scale if they need to run and decide all the things that they're running and deciding. So they know, but it's scary to let go, you know, especially when things aren't being done the way they would do them or big customers are on the line. I talked to a client recently who realized he's like, I'm burnt out, I'm stressed. It's not because of the job. It's because every time, like, something's going wrong, I step back in and try to, like, handle it all and manage it all. And it's too much, but it's scary to let go. So I think there's a risk in founder mode that it sort of gives permission to back off from the fear of letting go and stay in all the weeds and the details in a way that doesn't allow you to scale. So like any dogma, it's probably, you know, like a broken clock is right twice a day. Like there are some moments where getting really involved in the details as the founder is awesome and something you really want to do, and it serves the company and the team really well, and other moments where it doesn't. And so I think any idea, like, you know, I don't know what we call the opposite of founder mode, CEO mode or delegate, delegator mode versus founder mode. They're not like modes you want to get stuck in, right? Like imagine your car was like stuck in, you know, 5th gear all the time, like, but in traffic that wouldn't work very well, right? So like you don't want to get stuck in any mode. You want to be discerning about, oh, in this situation, like, you know, I don't know, there's some product innovation that maybe I'm as the founder in a unique position to have enough context to really guide. And so I'm gonna step back in and I'm not gonna be dogmatic that I should never be involved in the details. So I'm gonna go into the quote unquote founder mode and get really involved. And in these other situation, oh, I had, you know, I don't know, for go-to-market, I have a really competent head of marketing, head of sales that actually, would do a better job than I would, well then I, you know, best to let go and get out of the way. And that's a thing to think about too for founders. Like one of the cool things about being a founder and being a CEO is there's not really one right way to do it, you know, especially CEO. And so there are CEOs who are really kind of product and engineering minded. And so for them it might make sense. And they, you know, part of what I, when I say makes sense, It's not just sort of in abstract what's best for the business, it's what do you wanna do, right? Because if you as the CEO and founder are doing the things that light you up and energize you and you're passionate about, that's good for everybody, right? You're gonna bring more energy and aliveness into the business and people are gonna feel that, it's gonna overflow. So if you love product and you love getting involved, that might be great for the business and you can design around that and hire around that. There are others who are more like the evangelical CEO, want to be out, you know, speaking and talking to customers and more in like customer-facing. And so, you know, is founder mode being deeply involved in product or deeply involved with customers? No, it's, it's being involved in the thing that you're uniquely great at and love to do. So I think that makes a lot of sense. And so again, where founders kind of justify or logic themselves out of doing the things they love to do. It's really nice to give yourself permission through this notion of founder mode, like, oh, I get to do the product or even engineering, right? Even coding now and then, you know, like there's times when if you're a genius software developer and that was what uniquely made the company successful, like whether it's coding or running, you know, running engineering projects. Like there's times where that actually makes total sense for the business for you to come in for like the tip of the spear projects or really complex stuff. So I think it broke through the dogma of as a founder, you know, you only do high leverage activities and high leverage activities are only those that are really abstract and, you know, where you're just managing and delegating. And I think there's actually a real discernment to what level to fly the plane, to use that metaphor. When do I come down and get really to the ground? And when do I go 30,000, 60,000 feet? And like everything, the art of leadership is discernment. It's not about having one mode that you're stuck in. It's about discerning what actually serves the company best. And I do think what lights you up and what you're uniquely great at and aligning how you spend your time with that is what serves you and the company best. That's like part of creating win for all. So, that's my biggest, I guess, resistance or reaction to the way most people have interpreted that whole founder mode is like, okay, it's, you know, where we've now moved from delegate and stay at the high level to get involved with all the details, don't let go. And I think there's a risk that that kind of protects you from having to do the scary thing of letting go when that actually is what serves best.

It seems like there's also this like association with founder mode being around like a lot of just hustle and grind and like do it or die kind of a thing. How do you, I guess, perceive that? And I mean, you also like you talk about play to win, right? So it's like, how might playing to win differ from this founder mode, do or die kind of thing?

Yeah, I guess that's interesting. I could see that. Most of what the way I've heard founder mode interpreted is around that, like getting involved in the details. And yeah, there is a lot of lore and philosophy and talk about, you know, 996, right? Which I think came out of China, which is like 9 AM to 9 PM, 6 days a week, right? And like hustle and grind. And what I think is important to recognize here is like there's a distinction between quantity of hours worked and we could say enjoyment of hours worked. And I think what happens is people conflate the two and they think, in order to be a great founder, I need to basically struggle, right? I need to work a lot of hours and hope those hours feel hard and stressful and like a grind, right? You hear that, oh, you gotta grind, founder grind. And so I think, and then I come along sometimes and I'm like, no, you can do it with ease and joy. And people hear that as few hours worked. And that's not actually what I mean. And so that's the first thing I think to recognize is like, you can work a lot of hours, you know, call it 60, 70, 80, 90 hours. And have those hours be really enjoyable and be in a state of flow. And, you know, there are some founders who love to work and they love to be engaged in the business. And maybe they're at a point in their life where that feels like a great choice to spend most of their waking hours. Now, again, I do think there's a place where, like, we have to honor the fact that we're human beings and human beings work rhythmically. And we need to rest and renew to be at our best and to be in a state of flow. But taking that aside for a second, if you want to work 80, 90 hours, great, right? There's nothing wrong with that. And if you think that those 80, 90 hours have to be a struggle, I just think that's not true. And I think it's a little bit of a tragedy that you think that because you could spend those 80, 90 hours in a state of flow, working in a way that you enjoy, where it feels like play and it's fun and exciting and enlivening. And so to me, if you think that has to be a struggle, I think that's a big— a bit of a tragedy. Now, if you want to struggle, great. Like, again, like, I don't say there's one right way to do things, but I think if you have a limiting belief that it has to be a struggle, I want you to at least invite founders to examine that limiting belief and see, could you actually believe it could be joyful? Could you spend the time, you know, like we were saying, like most of your time doing the things you love to do that light you up in a way that you love to do them? And if that's a lot of hours, great. You know, there's a lot of different— obviously a startup is not a startup. There's a lot of different startups in different industries with different advantages, with different, you know, technologies. And so Are there market realities? Yes, I do think there's times where you're in a really competitive environment where there's not a huge moat you're building, and it might be that input actually does equate to output. But I think most of the time, input and output are not as— like, quantity of input and degree of output are not as correlated as people pretend they are. And, you know, like, A really simple example of this, the guy who started the auto repair shop in your town is an entrepreneur. I don't think that Sam Altman, Brian Chesky, Elon Musk work a million times more hours than that guy, and yet they've created a million or maybe a billion times more value. So it's pretty clear that like the quantity, at some point, the quantity of hours you worked is not the thing that determines the value you create. Like that's kind of obvious. So, you know, all things being equal, would more quantity create more output? Maybe. But again, I'd say, you know, we all, we've all had the experience of, you know, an hour we're at, like we're, we're in flow, we're at our peak. We come up with this idea that move the needle, maybe a quantum leap in what's possible for the company, versus that 90th hour where we're languishing and we're just falling asleep but still typing. An hour is not an hour, right? And so, I do think there's some optimal point in the curve where how many hours can you work in a state of flow? There is probably some point where if you try to push beyond your natural limits, you go out of a state of flow into a, like, kind of survival zone. And some of this, you know, I learned from, um, the book The Powerful Engagement, where, like, we just naturally, if we try to push too hard for too long, we go into survival zone where we're still pushing hard but less productive. And then if we end up burning out— and I do think, you know, a lot of founders are experiencing burnout because they're both they're not optimizing the quantity of hours, but moreover, because the quality of the experience they're having in those hours is really low in terms of enjoyment and aliveness, joy. And that has a lot to do with their mindset, you know, whether they're operating from threat, where they're focusing on like the frustration of wishing they were already somewhere they're not, or the fear of like, oh gosh, if I don't do this, these bad things will happen. Instead of being in that state of flow where they're just, you know, focusing on the desired future state and, you know, in an inspired, you know, way motivating themselves and their team to create what they want.

Okay, so pretty much main distinction is doing what lights— what lights you up, which puts you in a totally different state and will likely have you just leaning into what you actually want to do versus forcing yourself to do something you don't want to do, which would be struggle and all that stuff.

Yeah, I let you think of it like force versus flow, right? Like, are you forcing it? Are you, you know, a lot of effort trying to make something happen that you think you should, or versus more like following aliveness, doing the— doing what you really want to do, again, in the context of playing to win and wanting your companies to be successful. But even the word playing to win, like the operative word is playing, right? And there, you know, the, the reason I talk about playing to win a lot is because a lot of founders think that if they let go of attachment to the outcome, they will no longer be motivated to win. Right. It's like, oh, you know, I was like, well, could you just 'Could you let go of attachment to your startup being successful?' Or even more scandalous, I'll say, 'Are you willing to see how your startup failing could be just as good as your startup succeeding?' And they're like, 'What the— no way!' But if we really look at it, you know, 'Can you know with certainty that your mind is right, that your startup failing is like the good outcome— I'm sorry, your startup failing is the bad outcome and your startup succeeding is the good one?' It's like, What could happen if your startup fails? What do you— what might you get to learn? How might you get to grow? How might you wake up spiritually? How might you burn up your ego? How might you let go of all these employees and let them go do other cool things? Maybe your next startup will change the world in some way, you know, like, can you really know with certainty that this startup being successful is like the good right path for your life? And usually eventually people will be like, okay, maybe I could see how I could let go of attachment and my startup not succeeding could be okay. But then they immediately get scared they're going to lose their motivation. And that's where I say, well, like, do you ever play intramural sports? And they're like, oh yeah. And some people, yeah, or rec league or whatever. It's like, do you just kind of go out there and like, you know, lazily run around the field or do you play to win? And they're like, oh no, you know, not always, but often like I play to win. I'm like, well, what, why? Like, it's just more fun that way. Like, exactly. Like, you could choose to play to win because it's more fun. You're playing to win, so you're more likely to win than not playing to win. But you could do all that without being attached to winning. And, um, you know, what creates attachment is the thought that winning is the right thing, and also that your well-being, your sense of peace, joy, fulfillment, uh, or safety or freedom or worthiness are somehow dependent on you winning and being successful, which they're not. So play to win without being attached to the outcome.

That's good. It's good. I just now had a thought about— it's like when you play, when you're playing a game, just like sports or whatever, it's like the feedback loop is so fast. So you get that, you know, instant, I guess, gratification. Yeah, it's a whole lot more, I guess, feel like play. Just, just kind of speaking, uh, for myself versus like, I guess in business it seems like that feedback loop is extended so much that it doesn't feel as much like—

it can be. I, I think— I don't think it's just the, the feedback cycle time. I think it's also that you don't take it personally.

Mm-hmm.

Right. When you don't take it personally, it feels like play.

Okay.

Makes it feel serious and not like play is taking it personally, i.e., making it mean something about you. If you're, if you're playing rec league soccer and you miss a goal, most of the time you don't make that mean something about you, your worth, your future, right? You're not like, oh God. You know, I'm, I'm not going to be safe. I'm, oh my, I'm no longer, you know, I'm not going to have freedom. I'm not worthy because I missed that. You're just like, oops, missed it, you know. Okay, like, I'll, you know, maybe you learn something like, oh, you know, maybe I need to run a little faster, or, you know, whatever, get my laces on the ball or something like that. So you, you're, um, you're— the way you interpret the feedback is about winning the game It's not about you as a human being. Whereas if you miss your target, you know, or miss your goal in your startup, often it's like, oh God, you know, I'm not as good a CEO as I thought I was, you know? And now it's like, oh, company's gonna fail. I'm gonna be out on the street. I'm gonna be ashamed. Everyone's gonna hate me. I'm not gonna have any friends. I'm gonna end up, you know, scared, hungry, and alone. Like we make it mean all this stuff about us and our future. Instead of just, oh, like in this game of Monopoly called business, like that didn't work. You know, I tried this thing and it didn't lead to the result I wanted. Okay, let me try this other thing, right? That's what we do often in sports or in actual games. Like if you're playing Monopoly or board game, it's like, oh, what, what about that didn't work so that next time I can do it more effectively, as opposed to I'm just bad or I'm ineffective or I'm, you know, and, or my whole future is ruined. So I think the real key is, you know, when you don't make it mean anything about you, it can feel like play.

I see. Yeah, it makes sense.