How to Make High-Stakes Decisions with Only 10% Information ft Hiten Shah (@hitenshow)

0:00 If you meet with me, you're going to get a purple bruise. And it's going to be somewhere where you know you need the bruise. You might have had an accident there or a pain at that bruise before you are aware. But I'm just going to poke [music] it and push on it because I think that's what you need to hear. >> Okay, in my mind, and I think this is true, you're a master of a lot of different things. Learning, systems, growth, figuring people [music] out, figuring yourself out.

0:22 >> And my goal is improve. My goal isn't some metric or some milestone. It's just straight up. Get better all the time. The best way to describe it would be like poking at the world and then seeing what pokes back [music] in order to sort of calibrate how extreme can I make some of the changes. How long can you go through these loops? As long as you want. It can drive you [music] crazy, too. There is no end. You start going down that path, you will find these. And then you can decide whether it's a story you want [music] to keep or not.

0:48 >> Let's talk about that. >> [music] >> Hiten, I'm so excited to have you here. Thank you so much for taking the time. >> Yeah, for sure. Okay, in my mind, and I think this is true, you're a master of a lot of different things. Learning, systems, growth, figuring people out, figuring yourself out, life. Um so, it's really impressive. And I think 10 years ago, I wanted to be someone like you, you know, how someone who runs multiple companies, produces a lot of content, does a podcast, blog. I'm still figuring out how to get there. So. Yeah, I think you're getting there.

1:27 Uh slow, very, very slow steps. So, let's start with something that you just mentioned to me before this conversation. Uh the new year, new year, new you. You mentioned that you start thinking about the new year around October. Tell me more about your process for setting up new goals for the new year. And what do you actually do? Yeah, you know, um I think there uh the thing we were talking about was you know, time is artificial.

1:59 And we kind of make it up as society and have made it up. So, as much as I believe that where like I want to evolve, improve, iterate myself all the time, there are specific like uh time sort of milestones that I try to figure out how to leverage to make change happen. And I [snorts] think that that's the broader way I think about it. And what I've found for myself over the last, let's say, 5 6 7 years is >> [snorts] >> by the time Halloween hits, I want to have enough clarity about what I want to change for the next year. So, like like like meaning like uh there's these areas that I I I I feel like we should improve or I wanted to get to X Y or Z uh this year and I haven't. Um there were a few of those areas actually last year where I just didn't get to the it. And so then what I do is between Halloween and basically like New [clears throat] Year, I'm sort of um uh the best way to describe it would be like poking at the world and saying and then seeing what poke back in order to sort of calibrate how extreme can I make some of the changes, who's going to push back, what's going to push back, uh am I like feeling good about how I'm thinking about it.

3:25 The reason I do that is because starting about Halloween, a lot of things start slowing down. And the world is at a slower pace, which I actually just helps me think. Because especially these days when there's so much information and things you can dive into and focus and things like that are much harder. So, it's kind of a long-winded way of saying like I actually don't have goals. I don't look at it like that. Because I think there are very clear things when it comes to a business where you should have goals, totally. Like Yeah, revenue goals, um hiring goals, whatever those goals are.

4:07 That's all fine. But personally, I'm just trying to improve myself. And my goal is improvement. My goal isn't like some metric or some milestone. It's just straight up get better, get better all the time. There are times in the world when to be honest, it's easier to reflect or easier to do do certain things. And like, I've learned to take advantage of that. Yeah, I totally agree with you that time is an artificial construct, but at the same time having those milestones or seasons when you know, as you said that not as much information will come in and you have just more time personally to reflect because you're not over flooded with externality, uh is really helpful.

4:46 So, couple of things to dive into. When you say you poke at things and see what pokes back, give the details. What does your process actually look like? So, you're on a journey of self-improvement and bettering yourself. What does that in Hitchens operating system actually mean? Yeah, so like um I love that you asked it the way you did because I I I tend to really want to give and also get. Get is harder. But give very contextual advice. So, this idea of is amazing.

5:23 It might be a you thing. It might be a someone else thing. But based on your personality and and how you uh deal with the world you might do this differently. The way I deal with the world is I like to experiment and test things even subconsciously when I don't know I'm doing it. So, I will give you like a very unrelated example cuz I think that'll help. Like um if I'm speaking to someone I am subconsciously almost automatically testing what resonates with them and what doesn't.

6:11 It's almost like you're running the experiments off of testing out a conversation with them in the background. >> Yeah, basically. And it's not like consciously I can describe, oh, she said this, I said that, this happened. I don't mean that. It's more like little nuances and cues of like what interests them or what reaction do I get or do I get a disgusting reaction or the opposite or what do I get? And so, I I I sort of Let Let's put it this way. I think these type of things are not even superpowers, they're like natural abilities we gravitate towards and often times we don't know.

6:53 So, one when I didn't know it it was kind of like this. So, I've been in startups in the ecosystem for quite some time, like over 20 years. And there are people I might have met, let's say, 15, 16, 17, 18 years ago. And I'm actually thinking of someone very specific. And I would give him thoughts and advice in such a way that it would take him and and everyone at that time their own time to figure out what to do with what I said.

7:31 It was usually because I felt like I knew the answer. Like let's say they were asking me advice about their startup or something. I would usually go straight to them, their personality why they do the things they do instead of helping them with the question they actually have. But I would hit some root there that like almost like I I called it like if you meet with me back then, probably this is the best way to describe it. If you meet with me, you're going to get a purple bruise. And it's going to be somewhere where you know you need the bruise, you know it hurt, you might have had a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a there of pain at that bruise before you're aware, but I'm just going to poke it and push on it because I think that's what you need to hear.

8:18 So, what would happen is someone would come back to me 6 months later and be like, "Hey, that thing you said to me 6 months ago, I get it now." And and you know, you might think, "Hey, that's good. Win for them, win for me." But I think like what I realized back then is like I want to improve my ability to help someone so they take action literally right after the meeting. And that doesn't mean I'm giving them tactics or honestly saying or doing anything completely different than what I did before. So, my way of improving that process was meet with someone and then right away after I'm taking notes that I will never look at again.

9:08 And that's what got me to subconsciously, without thinking about it, be able to improve in the moment with a person and a conversation. Because I was helping a bunch of founders, I always loved doing that, and I would talk to them about things, and it went from 6 months to literally I'm getting a text the next day. And the person's like, "Hey, thank you for that. It was really helpful." Blah blah blah blah blah blah. Then I'm getting maybe a text a week later, a month later, and whatever I said to them actually resonated with them. And I just learned to like tune in. It wasn't like I was holding anything back. It was more like I was priming them to be open to what I what I say without the reaction I used to get. Cuz the reaction I used to get was clearly not providing them with enough value fast enough, in my opinion. Maybe in their their opinion it was, but in mine it wasn't. I'm going to, just for anyone listening, dive into the whole topic of personalities and um how you became a student of yourself and people around you, cuz I think that's a very interesting topic. Coming back to your own process and you poking at things around you. So, you said that subconsciously you're always running experiment, because that's how your personality works. And so, throughout the year, around October, you start running experiments on poking different areas of your life to see how they respond. So, what does that process actually look like?

10:33 Yeah. Um Like, what are you poking at? What does that look like? Are you writing? Are you talking to people? Like, with the example of talking to founders, maybe there is a, you know, a Rolodex of people that you're interacting with and you're running quote-unquote experiments. Most of the time it's something that most of the time the process is very much like um it's actually very blunt and can be applied to almost anything, which is just identify the current state and figure out what bugs me about it in all the various areas where I think I want to improve. So, I usually have multiple businesses. Um so, that's usually the first low-hanging fruit. Um uh most of my life stuff is very sorted out, like in terms of family and all those things, living situations, all that. So, most of the time those are not areas that I care to do anything about. So, it's like a business, and it's a blunt process of like what do I not like about this thing right now? Not even what do I want to improve? It's like just what do I not like? And and and usually that starts with what is the current state?

11:54 And without making it a goal, what where where would I like to get to? And then basically just poking whatever I need to poke to figure out where that difference is and how I can make that shift. So, sometimes it's people, sometimes it's a vast majority of the time it's how I'm thinking about it. That's like probably 90 95% of the problem. And are you writing things down? Are you talking to AI? >> So, I take a lot of notes.

12:25 Um AI showed up for this process this year. Um I have, you know, getting into some of the personality stuff, I will make a project, I've made a project, I put all my personality stuff in it, and I can chat with it. Um whether it's my enneagram or my human design or whatever I'm into at the time. I'm into these things. Um but maybe other people are into other things. Right? You put that in there, whether it's horoscope or whatever. I mean, even if you want MBTI cuz that's more scientific in your mind. I don't think it is, but other people do.

12:57 >> Yeah. Um so, whatever it is, put it in there, give it simple instructions like help me help myself or something. You don't need to make it complicated. And then just chat with the project, and it is amazing how contextual it is when it has your context and stuff about you. And I've learned so many things. So, that that I built out last year at some point. Which which AI are you using? Um I actually built it in Claude first.

13:26 And and I used to use Claude a lot and then I moved over to Chat GPT. And you know, I think they're all good for different things now and they're starting to figure out their lanes and I don't think Claude is very good for um the work that I try to do around myself. I saw this tweet the other day that Chat GPT is like your personal CEO and Claude is more of like a CMO. I recently started using four AIs in parallel to see what results they yield, but I'm still trying to figure out which one's best at work.

14:05 Yeah, you know, I don't think Claude writes great content compared to Chat GPT and I know a lot of people do. Yeah, that's a hot take. >> And and my argument is that Claude is good at writing code, not content. And always will be cuz that's what they care about. And part of the reason I don't use Claude for that is Claude has a tendency to like like the hammer they have is code. So everything you give it, it will try to run code for you. When you're writing, I don't want it to run any code. Like even Chat GPT has this problem sometimes, but if I upload a CSV or Excel file, it's trying to run code.

14:46 Guess what? If I copy and paste if I copy the cells and paste them in the blank tab, it's not going to run code, but it's still got all the context. So, I think there's these nuances, but overall I do want to share my main gripe with Claude. My main gripe with Claude is I I run out of tokens, the errors are bad and it gets unusable really fast and I found myself switching over to Chat GPT constantly. So even if it was better, if it doesn't work when I need it, it's not going to work. And this is a consistent pattern. Not to complain about what they're doing, but someone should tell them that like they can build a better product very easily if they just cared about these things.

15:26 Cuz I really don't think they do, unfortunately. So, some of this is just a user complaining about the tool, but other parts of it are like I used to use Claude only. I didn't want to use ChatGPT for this stuff. They pushed me over to ChatGPT. Then I realized, "Oh, for the things I'm doing, I can get everything done with ChatGPT cuz whatever I was doing with Claude, I can get ChatGPT do it as good if not better.

15:54 It might take a little more work, fine, in some areas, but that's how both of them are. Some stuff is easier in ChatGPT, some stuff's easier in Claude, and some stuff completely easier in Gemini. I would actually say COO is actually Gemini in my opinion. And Claude is much more personal. Or not Claude, sorry. ChatGPT is much more personal, and Claude sits there trying to I actually think it's the best for engineers. Today. Okay, that that makes a lot of sense. So, you have a project built out now in ChatGPT, how much time do you spend on poking and reflecting? Uh I I wouldn't use a Most of the time what I'll do is um the poking it is more about like testing things. That's why I kind of gave you that example of like if I'm talking to someone, I figured out how to make that something I can improve just by taking those notes, because I can be like, "Oh, like those notes might be like, 'Oh, crap, I used this word and they didn't seem to understand it.'" And so, every single meeting you have, you take notes afterwards?

16:56 >> to. Yeah. Oh, you used to? What happened? I I hit the goal I wanted to. Oh, the goal of the >> getting that 6-month thing. And I was getting and so now it's like very natural. And we've been in meetings like that, right? Like you were able to think about what to do during the meeting and after it. And you didn't come back to me 6 months later and be like, "You were right." What was happening a lot is they come back 6 months later and he like, were right." Like if I was right and it took you 6 months to come back to me, I actually was wrong. I didn't actually help you enough, right? So, what the point there is like there is a investigative sort of personality trait that I have that I know I have. I'm just trying to utilize it in good ways versus bad.

17:42 Cuz bad ways would be like if if you if you notice like when I talk to you, I rarely will ask you a question. Mhm, that's true actually. Right. Why? I guess you want to Mhm, that's a good question. You want to hear what comes up naturally without you leading me in a specific direction. >> If I ask you a question, that means I have an agenda. I try to make the vast majority of my meetings with no agenda.

18:10 Because when I have an agenda in a meeting, it's usually work. And that means that like I will typically be the person whether other people on the call know it or not to refocus a conversation. Which is very different than trying to help a friend or talk to someone. Right? So, I think I actually have those modes. So, if I'm in like someone I I met a while ago uh and I work with them, they had never been in a meeting with me, like a work meeting.

18:43 And but I work with them, but we never been on a meeting. We got in a meeting and it was just one of those meetings where I was doing a lot of that refocusing. Refocusing with questions, right? Or how do you What do you refocus >> Question Yeah, questions are usually the best cuz you ask a question and everyone starts And if you ask the right question, you know the game, right? So, yeah, exactly. That's why I was going there. So, if I'm in that mode, it's there and then literally she gets off the call and she messaged me saying "Oh, so that's Heathen in the meeting."

19:11 I'm like, "No, that's heated in a meeting that matters. That really matters. Where if you don't get this right, someone's fired or someone's going to be mad or we're just going to mess this up, right?" So, I I think like the muscle for me is actually being able to identify this is the the system and the core thing that relates to a lot of the things we've talked about, but is being able to identify current state and what we need to change. And I'm just trying to get us to that change as fast as possible. And that's the process that I try to use during the October to December thing. And And the thing I've just learned is like the world is quieter. That's it.

19:53 Which helps me think. Cuz when the world is noisy, I need to go somewhere to think. But I can be in my home and the world is quiet and I can think in a way that I couldn't on a normal day, whether it's cuz of meetings or just the energy out there. What is the most effective way for you to think? Is it writing? Is it something else? I actually haven't found any better way than talking it out. Oh. And self-talk.

20:23 Oh, what do you mean? Like rubber ducking? Sort of. Um sort of, yeah, but more like Okay. So, you asked the question and you mentioned tactics. But talking it out can be writing it out. It can be recording it on a voice recorder. >> That's true. >> It can be talking to ChatGPT about it. Or it could be self-talk. But at the end of the day, like if it's basically um what I I think most of what I do is what people would call metacognition, where you're thinking about thinking.

20:59 Why do you say it this? Why do you say this? Why do you do this? Now, I was talking to someone who's uh very um very good at poker. And and and he's like, "Oh, there's this thing in poker." I forgot what it's called. Uh, my uncle had me read Liar's Poker back in the day. Forgot why. But, um, the person said there's this thing in poker. And I'm like, "What is it?" And he's like, "Well, it's a thing that I see you doing. Do you know you're doing it?" I'm like, "I don't know what you're talking about." He's like, "There's this thing where what you're trying to figure out." And this is what chess and other things do, which is like uh, uh, something along the lines of "I know what you're thinking that I'm thinking that you're thinking that I'm thinking." And he was basically saying the levels the the deeper you can go around that and and that just way of um, understanding like something or trying to is basically some poker strategy.

21:54 Again, I probably butchered it, but what I latched onto is the idea that like if you go back to what I was trying to do subconsciously, if I say something I want to know what you're thinking when I say it. But, I can only do that if I already knew what you were thinking before. It gets really weird. But, like I think you can get better at stuff like that just by thinking about your own thinking.

22:21 Cuz then you can think about other people's thinking much easier. As long as you don't get stuck in personalities of yourself or you have a better understanding. So, when I hear you say you're thinking about your own thinking, I'm thinking that you're trying to figure out how you work and who you are. What does it mean to think about your own thinking? Like you think, "Okay, I'm having this thought." And then you're thinking you're trying to reverse engineer why you're having this thought.

22:47 >> Yeah. How long can you go through these loops? As long as you want. It can drive you crazy, too. There there is no end. I mean, it's like if you really think about it, there's no end to life. Like yeah, we die and all that, but like there's no end, like like we don't even know why we're here. Mhm. Like, there's no answer. So, this is one of those things where it is existential. As you can think about that all day. But, in a specific area, like what I mentioned is, if I want to improve my thinking about someone else's problems, businesses in this case, I did that loop. Okay, I'm talking to them about it. I'm giving them feedback. I go took some notes to just make sure I essentially um codified the learning.

23:30 I never look at the notes again. Ever. Because usually if there's follow-ups, I'll do them. Those I have a good memory for. Those are easy. The harder parts are like, I said this thing didn't resonate. I said this thing it resonated. I should have said that this way, or I missed this thing to say, things like that. So, I would just do that because I wanted to get good at giving people contextual advice. That's very hard to do.

23:56 Now, you would think that asking a lot of questions gets you contextual advice. Actually, figuring out how they think is why you're asking the questions. If I can figure out how you think by you just talking, that's much more interesting to me than by me asking questions. To your point, cuz I'm leading the witness somewhere. If I don't know where to lead them, why the hell am I asking the question? Now, if you came to me and said, "Hey, I have a marketing problem."

24:20 First thing I'll do is, "Okay, what's the marketing problem?" You'd probably say it. And then I would be like, "Okay." And then ask you a few questions to dig in, but we started with something you cared about. And I I could go go from there, but the amount of questions I'm going to ask versus what someone who is as curious as me is probably 10x difference. Cuz my curiosity I don't need answered because you answered my question.

24:45 I can get it answered by just hearing you talk. So, then for someone listening and trying to be like, "Okay, I want to be a much more self-reflective, and I want to understand how to set goals that would be or how to figure out systems and ways for how to improve myself and my own thinking and my own life, what can they take away from your process? I think you have to first realize that most of the things you're doing and why you're doing them are completely not conscious to you in a way that they could be.

25:20 So, the easiest, quickest thing I would say is everyone gets triggered. If you get triggered, and what I mean by that is somebody says or does something or you read something or let's just say more broadly you experience something. That could even be reading an article. And it triggers you. Trigger means it invokes an emotion or feeling that you did not have prior. Could be negative or positive. We all have them.

25:52 If you can find out if you can when it happens, one, remember it happened, and two, find your time whether it's in the moment or after to self-reflect on it, that's the easiest tactic. Because it's likely you're going to find negative triggers first and go for those cuz we all are probably going to go there. But if something's legit triggering you and you don't want it to or you want it even if you want it to, but you want to improve yourself, you probably should look at what's going on there.

26:24 So, that's the easy one. It's like why did you get mad? It's the simple thing is why did you get mad? When they said that, why did you get mad? Or and you can ask that for yourself. You know, and and again, like there's a lot of theories and psychology around all of this stuff, but at at the end of the end of the day, we're living in our own minds. So, all I'm suggesting is that you figure out what house you're living in.

26:47 You know, where the rooms are and all this stuff. Like I used to have this thing where I uh my CTO and I uh we would talk about this and like one of the things we came up with is like, "Oh, there's boxes in the mind." And that box is over there and it's shut and it's got a duct tape. Okay? Or that box is over there. Cool. And what that means is there's a box. I don't have to go open the box to go look in it and I know the box exists. And the more of these boxes you have, the more complicated your life is. So, you try to reduce the number of boxes ideally. So, that was an analogy that I had gotten to which is like because there are things that we haven't have in our minds that we cannot go look at.

27:26 But we can probably label them. And say, "That's a box." So, then you know that it exists. Otherwise, we're not acknowledging it. So, whether it's that analogy or whatever the heck works for you, the house, the whatever, um if you do this, you will come up with those things. And those things will help your life. But those things might be very different than the things I've come up. Yeah, I love this whole topic of mind and understanding yourself because I think that if you truly genuinely understand yourself, you have so many unlocks for what you truly want, how to get there, as you said, what triggers you probably gives you some sort of additional information. What made you Do you remember the moments that you started looking at yourself and looking to understand how your mind works? What triggered this? Were you always like this? Um I think I was always like this somehow.

28:20 And and it was honestly just curiosity more than anything else and being able being comfortable asking why and not having an answer. A lot of people are not comfortable asking why and not having an answer. But I generally feel very comfortable with that. But again, personality. Most people don't feel comfortable with that that I've met. Like you can't ask you can't ask why and not going to answer. An- another way I think about this and again, knowing yourself, is um yeah, when I when I was working like somebody uh some at my last job my only job, somebody came to me and they're like, "Hey, out of everyone I've ever worked with, you're the most decisive person."

29:02 Like, "Okay." This person worked at like Apple and worked at Dropbox where I was at the time and like >> [snorts] >> the the reason I'm mentioning that is like I know for myself that I've gotten really good at and probably was pretty good at this early on it at you can give me 10% of the information and I'm willing to make a decision. And I've noticed a lot of people need 90% not 10. Give me 10, I'll make a decision because or I'll make a decision that we cannot make a decision and here's exactly why and what we should go find it out. But usually even with 10%, I can go make a decision. And so she was looking at the she was saying I've decisive.

29:46 What I'm saying is actually your confidence and conviction in making a decision with very little information. But if you think about it, that's what a founder does. That's all a founder does. They're never going to have enough information. So you have to make a decision with way less information and feel confident in it enough to make moves as a result of it. Yeah, 10% of information is not it's interesting that you are so decisive given you know the 10% of information and at the same time you also think so much because in my mind I'm like if you think so much you have all this meta thinking then you kind of fall into the the category of over thinkers and then you can be like over thinking that decision.

30:31 >> thought enough though you can reduce the amount of information you need going forward. Because you've had enough experience to see how the But the thinking is the experience in that case. That's very meta. Right? Like if you think about thinking, you're experiencing something what we normally think of I experienced that thing. I did that marketing. I did that product thing. I did that sales thing, and that's experience. But like if you can just think about a problem, that's actually experience, too.

31:04 So if you're experiencing all these things and and doing them in a way where there's utility for it, then like, yeah. Like why do you need 80 90% of the information? You don't. 10% is good enough. Was the 10% uh Did you reach 10% over time, or has that always been the case? >> I think that's always been the case, and I think most of it >> think it comes from Yeah, from childhood or your parents?

31:27 >> it just comes from um I know I go back to this word, but I actually think it just comes from not losing parts of curiosity that a lot of people just lose over time. And usually they lose it because they're not in environments where um I'm going to get into another concept, but where freedom of thought is actually uh incentivized. And so I I think there's freedom of time. Usually you get freedom of time cuz you don't need to make money for a living. That's the typical way.

32:03 Or you get time after whatever you're doing to make money. But freedom of thought is actually more um useful and impactful if you think about a lot of things like that. Like you can have a full-time job, but that job doesn't take up your brain space in a way where you don't have that freedom to think. And so I would say that like I learned early on from the environment my parents created that curiosity should be valued, root causing things with five whys or things like that, even though they never said it. I learned about it many years later, was how you find things, but my parents were physicians, and my dad loves my mom, too, but like the It's like research is what they valued and cared about. So, whether they talked about it at home or not, the scientific method and those things were like all around me. They never used those words.

32:57 They weren't like professors or anything like that, but that's the work they did. They liked doing research. They liked doing experiments. So, I was exposed to that, but I was also exposed to like things like I had no curfew, but I was told from my father that if you have a problem, I need to be your first call. I never really did that, although I should have, cuz I had I caused a lot of trouble growing up.

33:22 Um but I was given the freedom to think and explore without a lot of rigid worldviews that weren't mine. I think most people grow up and realize that the worldviews that were theirs are still running in their system. A lot of whys that would trigger this and all that, if you start going down that path, you will find these things. And then you can decide whether it's a story you want to keep or not. If you don't want to keep it, those are the the stories you don't keep from childhood and things like that are actually the ones that are going to help you grow if you stop keeping this.

33:57 Right? Because you're you're essentially um uh removing an attachment to some kind of story or some kind of thing that you kind of got in your head. Wow, so many things to dive into. Just Just to set the agenda ground, I want to dive into how your parents did that, you know, giving you space to think. I want to dive into curiosity. I want to come back to getting to know yourself and personality test personality frameworks.

34:24 Uh also want to talk about your early entrepreneurial journey, because in my mind I'm like, "Oh, you're saying that there is space for curiosity and space to think, but at the same time you're also very busy, I assume, building your first company and then multiple companies. Okay, so let's get started. How exactly did your parents give you that space to think? And how and do you feel like you're cultivating the same environment for your kids right now?

34:50 Yeah, so I think one thing that I shared was as I grew up, I didn't have a curfew. So, that didn't put any limits to >> Can you explain what that is? I actually don't understand what that means. Okay. >> So, most of the time uh most kids were told, "Hey, you have to be home by 9:00 p.m." Okay. This was a time when we didn't have phones and we actually cared about getting a car when we're 16. So, fortunate enough, got a car.

35:19 But I didn't have a curfew. Because my dad didn't value the fact that I was home at a certain time. Okay. He valued the fact that I was okay over thinking that being home at a certain time meant I was okay. >> controlling you and your decisions. >> me the trust to make good and bad decisions around these type of things. So, that was much later. I think younger um when I was 4 years old, my dad told me I should be an entrepreneur.

35:46 Then as I grew up >> were 4 years old? Damn. That's when he started. Um uh and he's a physician and he is Indian and that is very atypical. I don't think any of his peers or colleagues or, you know, cohorts of his age said that to their kids, right? Especially if they were physicians or they were lawyers or anything. >> trying to fulfill his own dream through you somehow? >> I'm sure he was. But he's also very entrepreneurial, so um but I'm sure there was some aspect of that. I I have a standing conversation I tried to have with him once. He just wasn't able to cuz he was uh in India and we were on a call.

36:29 So, I have a standing conversation to dive even deeper into why the heck did he tell me that? Because I had some answers from the past. He's like, "I got more to tell you." I'm like, "All right, great." And he never tells me like he never even speaks like that. Most of what I learned growing up from him was by observing him. And then I'll get to uh kind of some of the answers that uh for some of the questions you had. So, he told me that when I was four. Then as I grew up, he told me get married early and have kids early.

36:56 And that was probably 10, 12, 13. Um so, I met I started dating my wife when we were 15. Uh I had kids It's interesting that you were so so susceptible to what your dad was saying, cuz you know, for a lot of people they'd be like, "Oh, my parents said this and I completely rejected it." I think the age that he started that at was probably It was like four years old. Four years old where you're like, "I don't even know what that means." Yeah, yeah. But they you, I don't know.

37:26 >> Yeah, yeah. Um and so, I think I It's weird. That's a really good one. He gave me so much freedom in every area that these things felt like life lessons that he learned that he's trying to help me have a better life than him, but he didn't overreach. I know that might sound like overreaching, but he didn't it because he's like, "Look, if this is what you want, here's what I recommend." kind of thing.

37:58 But but he didn't have like all these rules. He just had these things like, "Hey, I'd like this for you." You should do this. You should do these other things. So, now I when I talk to him about this, I talk This was many years ago. I was like, "I'm not going to listen to you anymore. I did all those things. My kids are not going to listen to you. No one's going to listen to you around here." Are you ginger thing? So, I you know, there's no resentment, but like I don't know the alternative is is definitely the truth.

38:18 >> So, I assume you you're not doing that to your kids where you're like four years old? Okay." >> I haven't told them those things because I think we live in a different world where where those things are accessible and much easier and don't need um the kind of prodding or pushing. Um but um kids-wise like my daughter's 11, my son's 15. Um I think the environment they were raised in was very much uh my wife's a founder, I'm a founder.

38:53 Her brother's a founder. >> [laughter] >> One of One of their cousins is a founder. I don't have any siblings. Um Sounds like they might be founders, too. Like like like if they want to, right? Like um But the world might be very different, right? Going forward in a bunch of ways by the time they need to figure this out. So, I think they observe a lot of things and absorb those things and that's how kids are. So, that's why they say like it's more of the behavior of the parents than it is like the the like the specific things you prescribe them.

39:31 >> Exactly. So, why would I tell them anything? If I live my life the way that I think they should, then all I can do is live my life. So, like but I have a lot of um historical whatever the opposite of baggage is in my life so that a lot of the crap that a lot of people might be dealing with later, I've already dealt with cuz we've been dating since we're 15. So, all the weird stuff, all the bad habits, all the things like back and forth or how we operate or how we work together to get stuff done or manage the family is all very clean-cut and clear. And there's no arguments about any of that ever. And so, they never see us fight.

40:15 Right? And it's not that we don't disagree, but like we're not disagreeable either of us. So, it's like easy to manage a something where we feel differently about something. And they see that. So, I don't see them being people who are going to be argumentative and things like that. And they obviously see other people that are like that. Cuz even some parents they'll argue in front of everyone else and all that stuff. And like but growing up I had these rules like like that I created by observing my father. So, if my kids create rules by observing us, that's the best I got. It's better than even what my dad did trying to tell me those three things. But again, he'll explain to me a little more eventually and whatever. But it it just sounds like there were things that he felt were important for the day and age that I was living in versus him.

41:05 And some of them were things he wished he would have done, too. Don't get me wrong. But he got married early. He had a kid early enough. Um but he wasn't an entrepreneur in his mind. But he runs a nonprofit. He's retired. He's busier than when he was working. And he's been running that nonprofit forever. So, you know, while he was working. So, he's very entrepreneurial. I think he is an entrepreneur. He would say that, too, probably. But he didn't get to be a businessman.

41:32 I think that's really what he wanted me to be. And he got his wish. Let's come back to curiosity. Um so, because of your dad's role modeling and your mom's role modeling of researching and you seeing that you had this um mindset of I always need to be curious and to ask why. And sometimes there might be no answers, and that's okay. How can people be more curious? Cuz you The other thing you mentioned is that a lot of people lose their curiosity with time. And that probably happens because of all these different programs that we're constantly running and the boxes that we put ourselves in and the society puts us in. So, let's say you wake up and you're like, "Okay, damn. I'm not curious at all." What do you do to reignite your curiosity? I think usually people would probably come at it from like, "I'm not creative."

42:22 Or I'm blocked or something like that. If you root cause that, it goes back to curiosity. It's somewhere you lost It To me, curiosity in this context is the idea that I think in the context I usually find myself in, curiosity actually involves reserving judgment. So, all I would say is just as you're moving through the world, figure out where you're being judgy. Yeah, one thing that um I remember I had a conversation with someone the other day and they mentioned that our reactions to things are usually our reactions to past projections of things that are very similar. And so, that means that we're not even I think that kind of goes to being present. That means that we're not completely present with the things that we're experiencing, but our mind is constantly trying to map the things we're experiencing to past experiences. So, it's almost like we're living in the present Oh, sorry, in the past and in reactions to past.

43:23 >> That's right. And we're not open to reliving something and looking at it with a completely fresh perspective and seeing how we actually react in the present moment. That's why it's not childish curiosity, it's childlike curiosity. Right? Cuz childish generally means childish, but childlike basically means can you look at something like you Can you look at something like as if you've never looked at it before, but you've looked at it a billion times?

43:54 Can you look at your significant other like you've never seen them before? How do you do that? That to me is how you practice curiosity. Because that means you're shedding the judgment and assumptions you have about the thing at the moment that you're trying to essentially judge the thing. Right? So, how do you shed judgment? It's easier said than done. If someone is super judgmental, like what do they do? I think you have to figure out I actually think it starts with understanding where your assumptions are coming from.

44:21 So, as this goes into like work, like here here's why I'd rather someone talk than me ask a question. Because if someone talks, I can figure out what assumptions they're making very quickly. If I know what assumptions they're making, I know what judgments they're making. Because assumptions are what inform the judgment. The judgment is what causes us to have an impression that might be incorrect. So, it really goes back to an assumption. So, what I'm really trying to do is what is that person assuming?

44:48 And I try to do that to myself. So, if I look at something, I'm like, "Oh, works like that. Works like that. Or does this." Or even looking at a fireplace, I'm like, "Oh, where is the way to light the fireplace?" Haven't found it yet. Might be over there. But like, I don't need to look at it. I don't need to think about it. But like, can I look at it and be like, "What is this thing?"

45:08 Cuz if I can do that, then I've I've I've removed all the assumptions about oh, it's this thing in this like, you know, wall. The wall has a TV. There's a fire like, how do you practice being able to look at something and figure out how it works from first principles. >> basic building blocks, right? And and I think like that is the type of exercise. And that's like very hard to do. Cuz I look at it and I still think fireplace.

45:33 I don't look at it and I think bricks and granite and all that. But if you can start thinking like that, then you're taking it back down to its bare bones. And then you can have a bare bones understanding of something. I want to bring your under your curiosity about yourself and how you work to the famous incident that you had with hidden bombs and realizing that you kind of blew up in a way your own company that you were running and the fact that you were constantly bringing people new ideas and defocusing them.

46:02 How come you didn't realize that earlier given your um interest in self-understanding? Yeah. So, I think that the environment you put yourself in and the assumptions you make about that environment are what lead to some of those things that I was experiencing where I would And can you give pain some more color? Like what exactly was happening and how did you realize? >> So, at that time it was my first venture-backed startup and I had assumptions about what was important.

46:35 And and so what I thought was important was that we were nimble and moving fast and trying things constantly. And and that worked for a very long time because we were pivoting and trying to figure out what we had. But then even though the environment changed, which is we have customers, they're paying and all that, I didn't change. So, the environment at first was like exploratory and all that stuff. The environment after was like product market fit, grow the thing. But I kept operating at least half of my mindset was still in the past.

47:13 Back to the whole point that you made, right? So, if that's the case this is actually why certain people have certain judgments that like I don't think are accurate, but it's like, "Oh, that founder" and this has happened a lot less now, but "Oh, that founder is only good at early stage." It's like not necessarily. That founder might not have actually realized what the environment how the environment changed right in front of them because of what they were able to do. You actually want that founder to be able to do the next stages cuz there's an advantage they're going to have at those if they can figure out what those advantages are. Cuz instead of experimenting on getting the product market fit, we should have been experimenting on growth a lot more. I just confused those two things.

48:02 Yeah, I feel like the vibe of what you just said is very courage to be disliked, which I saw was a book that you found pretty impactful. Um, I generally always believe that in any moment we can change our own mindset and perspective, but there are obviously still innate traits and characteristics that will be an obstacle to how that change might happen. Did you have all of those realizations before you read courage to be disliked, or was that like a very impactful read that made you change?

48:31 >> is actually the weirdest thing about metacognition or some of the stuff we've talked about. If I have thought enough about something over time, so these little processes, then when I read something like that, it's basically basically synthesizing the things I believed already. Right? Or giving me names to things. So, that's kind of what happened with that book. Which is like it gave me names for things that I couldn't quite understand.

49:02 Cuz my great relationships map to very clear delineation of their task and my task, which is a big part of the book. Yeah, [snorts] to to give a a bit of a summary on the book, one of the things is as you said, my what is your task and what is uh their task tasks. It kind of also reminds me of, do you know Mel Robbins, the the podcast host? She has the let let them theory, and the let them theory is kind of the same thing where you just let other people react to the things the way they want, and that is not your responsibility to impact their reaction in any way. Your responsibility is to do your thing, be yourself, um, and just seeing how the world reacts and adjusting your part of the job if you don't like the reaction, but you're not going to impact how other people are other person is going to react, what are they going to say, are they going to like you, are they going to dislike you.

49:54 So, this is complete waste of your energy and time. Yep. Yep. And so, when you click when that clicks for you, you realize that you should be focused on your tasks. So, in the whole theory is that the reason we have relationship dysfunction is cuz I'm focused on their task instead of my task. And we're mixing those or they're focused on my task, right? The framework I have that I got to before the book was um Batman and Robin.

50:27 So, the example I like to give is uh we bought a house and we were remodeling it. Took a couple years. Um so, my wife and I and she stepped in the house 700 times. I stepped in the house 20 times over 2 years. Guess who was Batman? Which basically means like like the analogy plays out. I've talked so many people this analogy, but it's like if you're doing something with someone else, usually it's a significant other relationship, you got a Batman and Robin as many things as you can. It's not like and someone told me, "Oh, so they're always Batman?" I'm like, "No, no, no, no. Depending on the task >> Ask, yeah. or the job or the thing, someone's Batman, someone's Robin.

51:08 Because if there's two Batmans, nothing's going to get done cuz they're both going to try to do the wrong things cuz there's no alignment. If there's two Robins, nothing's going to get done because they're both thinking they don't need to do it. If there's a Batman, it's very clear you're Batman and you're Robin. Now, what happens when Robin tries to go to Batman and give Batman an opinion about what Batman's doing and Batman doesn't want that opinion? Batman gets mad at Robin because what is Robin doing? They're encroaching on Batman's task.

51:38 I feel like that's also a common argument with child's care. I was just talking to a friend the other day and she was complaining about the fact that, you know, she's the one managing their au pair and then she had a really big argument with her husband about the fact that she's not managing their au pair also. So, okay, so what how do you reconcile You can't have two two people managing the au pair. It is clearly that she's Batman, but she doesn't want to be Batman, or she has a problem with her significant other being Batman or or Robin.

52:07 >> But, it's very likely in that scenario she is probably the one that should be Batman anyway, and there's some other problem she's trying to solve for. What the supplement? What is this what I found in those situations, where he's supposed to be Batman, but he's not being Batman. >> [laughter] >> That's usually what that boils down to. So many relationships I've helped at least understand what's going on with the framework. Okay, so then let's say you understand the framework. I think this is a really good segue into co-founder relationship.

52:34 So, you had your first your first co-founder was your brother-in-law brother, yeah, brother-in-law. And you guys started a company around like 15 or you were both 16 or >> he was 11, I was 15 when we met. I graduated college, um and he was uh graduating high school. Wow. And that's when we started the company. And then you're you're also running a company with your wife and I guess still are, and then you had another co-founder. So, okay, for anyone listening, how should people approach partnerships? Batman and Robin. Like like purely like the way I've made it work with so many different types of people throughout the years is getting clear about that delineation.

53:17 So, give me more specifics. How do you get clear? Um there is, you know, obviously a lot of perspectives on doing co-founder dating, realizing what everyone's values are, what their strengths, what their weaknesses. Um So, so I'll talk about two different things. The first thing I'll talk about is how to find a co-founder, cuz I think that kind of is where you were going, right? Then I'll talk about how to work with a co-founder cuz I think those are a few separate things.

53:45 Finding one there's just one exercise that you need to do if you're looking for one. I'm going to assume you found someone who might be someone you want to work with. So I'm going to start there cuz we don't need to talk about how to get there cuz there's a lot of ways to get there. There's infinite ways to get there actually. But once you're there and you're deciding to work together, people do things like work trials together, like work together for a few All that is fine.

54:11 But the fundamental thing that every time I tell this to someone and they do it, they're like, "Oh, thank you. It either saved me or it helped me and we're aligned." And and all it is is I'll tell you also the most common one that comes up as a issue. >> [laughter] >> So most common I'll go there first. The most common one that comes up, which cracks me up every time, is they both want to be CEO. Oh my god, that's such a common thing of lately.

54:36 Let me tell you how that comes up though and how I try to get them to pull it up earlier. Both people independently write It's probably like a an article of some sort. >> They just write independently without each other seeing it what they want. What do you want? What do you want out of working together? And just write that up. You can ask yourself other prompts or whatever, but the general thesis is independently write down what you both are trying to get out of this business. Because then you'll even find things like, "Oh, that person wants to sell it. That person actually wants to build something so big it goes public." Or they both want to be CEO.

55:15 Which is again absurdly common. And that's usually a non-starter once that shows up. Like you're done. You're usually done. Cuz then it's like we both want to be the person that the buck stops at. And co-CEOs rarely will really work. But if you go dig into the co-CEO relationship, it's exactly this Batman and Robin thing. One person is focused on this, other person is focused on that. So, you know, it's funny like I also break the rule a lot, but but like uh someone joined uh a new project. So, I also have a side note. To me, these initiatives are actually like these startups or businesses are actually project product business. And you're just going through those stages.

56:00 And yeah, product market fit and all that exists, but it's actually those stages that I think about. So, I have a project that I've been working on that's turning into a product that we're trying to fast-track into a business. I had someone join and literally the first call with um the team, I was like, "Hey, and I just said this, if you have a question or any of that, you can ask both of us. But like whatever whatever she says, like it might as well be how you folks have been treating me as if I said it."

56:35 Right? And I just called it that. And the reason for that is in that project or in that product now or that business, um I'm not spending all my time on it, she is. And I trust her so much where she can Batman the whole thing, I wouldn't care. Cuz she knows where to come back to me or whatever, but this is a person and this is a another side note. This is a I have a few people like this, but this is a person that for the last 10 or 12 years, we both try to talk to each other every week for about a half hour.

57:09 Just cuz we're friends. And I have a few people that I've done that with and like at this point a few weeks ago, well, earlier this year, well, late last year and earlier this year, it just ended up working out where I I get to work with her. So, um but I was very explicit, but in my mind and again, the reason I say that might be opposite of this Batman and Robin thing is like they could go to either of us. But what they might not know is that she's a bad [ __ ] in my head.

57:36 So, if she says something and like I disagree, like I have to convince her or I have to just go with it. But, that's my mental model because I know her attention on that project is going to be much greater than mine right now. And I already know her well enough that like it's not a problem of like we don't have the How can I put it? We don't have any work to do to understand each other.

58:00 >> [laughter] >> Or contact, zero. So, coming back to how someone finds a co-founder, the most important thing is for you and them to write out what they want. >> Individually. Mhm. And then what if it's a no-go, if it's a co-CEO situation, or someone wants to build a small business, the other person wants to scale up a company? Are there any other red flags? Those are the big ones. You're You're just trying to find where you disagree and trying to work through the disagreements. The CEO thing is rarely a disagreement that you can work through.

58:31 The what the goal of this business is is commonly you can work through that because you don't know if that outcome is possible, either of them. So, it doesn't really matter. And you're more just trying to get aligned on what type of business are we building? And that that is usually somebody just having a misconception about the world. Like they don't understand IPOs are hard or they don't understand you don't design a company to sell it usually unless you're expert at that.

58:57 Um things like that. But, but you you want to People don't tease any of this out and instead they do the work trails and build a product. And then they realize it's crap later when they got to figure out their titles or something else. It's like, wait, what are what are what what are our actual shared goals and objectives and really also shared values? And the hacks people do is like I'll work with my best friend or even the hack I did.

59:22 We spent 10 years more than 10 years, half hour every week, we tried to make the meeting. So, at least 30 to 50 times a year. And that was just like friends meeting. You guys were updating >> Talking about whatever, talking about whatever. I help them out, they help me out, whatever. Um and then obviously then it's an assumption of really deep trust and actually understanding someone. Let's talk about that. How do you trust How do you build up trust with with someone?

59:49 And how do you get to know someone really well to I guess deepen that trust? >> My uh It's funny. This is a good one and I'll give you one funny or interesting story. Uh I have relatives in India like a uh a cousin uncle like a uncle relative blood relative. Uh his My great uncle's kid. That's what I said. So, my dad's cousin actually. >> [laughter] >> And they're um extremely successful business people.

60:21 Like extremely successful. Runs in the family. Uh maybe. We were successful than I. Uh in in in in that in that context. Um and I asked him when I was like 15, "Hey, what do I need to know?" Trust takes 10 years. I was like, "Crap." >> [laughter] >> But I every part of me didn't want to agree or believe that.

60:56 But every time I think through that it just keeps coming back to what he said, which is like it takes 10 years. So, if I know it's going to take 10 years, then I'm really just trying to figure out who is who is worthy of that investment. I don't mean like me or like it both both sides, right? So, what relations which relationships are worthy of that investment? So, for example, uh a an uh engineer I've worked with I hired we hired him in like 2010 or 2011 at at Kissmetrics.

61:30 My first venture back company. He came He worked with me until we sold to Dropbox and he's still there. And he'll be there for however long. If I can help it, I would love to work with him again. Um that relationship is now 12 13 15 years easy 15 14 15 years. And I hired him because of some mutual friend we had who was like, "Hey, you're in the analytics space. Hey, he might be interesting for you cuz he he knows databases blah blah blah. I used to work with him." And then I met him like and he came on as the analytics engineer. He ended up being the head of product and engineering at Kissmetrics. And he was our CTO at Nira. He came on a little bit later, but he was working on one of my other projects at the time.

62:13 Um Like I trust him. It felt like it didn't take 10, but it probably took 10. Uh and and I think part of that is like you find people's patterns. And you find this you find all that through longevity. Like like like like through through you know, hitting reality. Hacking that is possible, but that's usually because there's a fundamental value system that is so aligned about the work actually that you don't need the time. So with Marie, my co-founder at Nira, there was a fundamental value system that somehow in some way that we aligned with and we got along.

62:55 And those two things are what hacked that process of trust, but it was a constant trust exercise exercise while with Steve, the the CTO guy, there's no exercise. Like there's even a few patterns we figured out that we're going to change if we if and when we work together again, um that were There were two times it happened and those were so critical that now we both are watching for it. It was just something in our thinking. Had nothing to do with the relationship, it was just more like if we thought differently those two times, those things we were working out would have been more successful. And like we figured that out, but like to be honest, I think it's trust, but it's really identifying those kind of things which you can't do without having enough shots on goal.

63:44 And if you get lucky, you get lucky and the thing works, great. You learn less. That's the funny thing. When things work quickly, you learn a lot less. Like a heck of a lot less. In fact, like when I when something works quickly, the amount of effort I put in to figure out why it worked is way greater than when it works slowly. For obvious reasons, but the reason I do that, which I don't see enough people doing, is cuz if it worked quickly and I don't know why it worked, I can't one, I can't repeat it. Two, I don't understand it.

64:13 Three, I think I'm screwed. Because I basically lost something I don't want to lose. And if you look out there in the world, a lot of founders are one-hit wonders. And they're not able to get past that. And it's simply because usually, when you look at their history, they got they got there too fast. Too fast. >> And they didn't understand how they got there or why they got there. Or it was too easy. But if it's easy, that's that's good.

64:36 Life is good. That's luck. But then you got to figure out what is it that made that good or made that work so fast. Not even made it work so fast, just what made it work. Cuz fast is like there's tailwind, there's a bunch of luck, and you have to discount a lot of that and be like, what is it that we controlled that made this happen? And you could learn nothing, but then you know you can't repeat it, which means the work is harder next time. And most people don't internalize this.

65:04 Yeah, I agree. I feel like the being really fast at making things work is more it's not a blessing in disguise, whatever the opposite of it is, because then you're like, "Oh, you know, you didn't build up a lot of the necessary skills to then repeat repeat the thing." And hopefully you got lucky that the thing worked fast, and you're still working on it. You're still reaping the benefits, but if you have to restart, I sometimes think about, you know, there's a lot of people who say that, "Oh, at school so-and-so was really hard, so I had to apply a lot of grit and work ethic to really figure it out."

65:36 And as someone who I've always been like most good at most like 80% getting 80% somewhere. I've been good at most things, yeah, pretty quick. And I'm kind of jealous of people who weren't that quick, because there are certain muscles that I feel like I wasn't able to build out. And maybe there are some parts of me that I'm like, maybe I'm not giving myself enough credit, but I think the hardship and grit is really, really important. And having the slowness of the lessons is also important, because then we kind of are dissatisfied when the progress happens too quickly, and it's not completely in our own hands, because then we externalize it as like, "Oh, I got lucky. This has happened."

66:14 And you feel like you didn't really actually put the work in. Yeah, and so that's why assessing it will help you see what work you did put in, and help you see like how to repeat it. Whether it's speed or just repeat success, cuz at the end of the day, once you're successful, you want to repeat it. If it took to If you got there quickly, you're not even able to understand how to repeat it, which means if you can't understand that, there's a lot of scenarios you can't.

66:40 You have to rebuild the muscle. Yeah, yeah. >> just ignore the fact that you got there quickly, and you don't understand it. You have to actually internalize that and build the processes you might not have, that you might have thought you needed to, but you didn't, cuz it happened quickly. Here's Here's like the most damning thing I can say about this. Every single time I hear about people interviewing at the fastest growing companies every single time, there is amounts of dysfunction that would not work if the thing wasn't working and didn't have product market fit so quickly.

67:15 Yeah, because 100% of the time. Yeah. Like and most of the time like you dig in and like, wait, is there excellence anywhere from a a proper standard? Or did they just get lucky and the market was >> if they're good, there's excellence in one area. If they're not good and they just got there, there's excellence nowhere. And like it's kind of crazy because those companies, if you think about that, they look the same as a dysfunctional company that's not successful. So, what's the difference?

67:43 There isn't any. They got lucky, but they did something to get that luck. I'm not discounting whatever their thing is, but do they know? And that's why when I find the one excellent piece, I'm like, all right, they know that that butters their bread. That's what I call it. Okay, I want to come back to co-founders. So, obviously a lot of it is people and people's alignments. I feel like now though for anyone's for anyone who's looking for a say tech co-founder, it's harder and I want to hear whether that's what You mean like someone like you that's technical and writes code or like >> No, just like harder to find someone who's down to start a business just because there is so many companies out there. Yeah. It's much easier to maybe go and make money at one of the growing startups. Like why take the risk?

68:27 Do you think it's harder to find a co-founder than say 10, 15 years ago? Because then it was a risky bet and now it's I mean, it's still a risky bet, but there is a lot of other bets you can take with your career. Cuz I hear so many people complaining about how hard it is to find a co-founder. You go to your friends, but the friend is already working at a job they like or they're thinking of a job that pays them much more than taking the risk. What would you recommend people who are in that spot?

68:53 I haven't met co-founder relationships that last where they don't like working together. And so my argument about this would be first, breaking the assumption that you need a co-founder. Sure. Right? Like, I don't actually think you need a co-founder. And now the the world of tech has invented uh founding member. Right, right. So, if I were to start from scratch, I would convince myself that I don't need a co-founder, but I want founding team members. And so, then the bar for what that person can do with you is much lower.

69:35 Because usually a co-founder means like in in the best sense, a lot of what you can do, they can do in areas that are not e- either of your expertise, which is a little bit of a nuance. Or, they're both of your expertise, but you both know that, so then you fill in the deficiencies with the team. Right? Which is what Marie and I did. We're both business people, neither of us write code, and [snorts] we knew consciously that we were both able to do the same things for the most part. Yeah, we had expertise here and there like if there was legal or compliance or anything, that was her thing because Batman and Robin, like, you don't want me doing that because she's better at it and she likes it. Well, she wouldn't say she likes it, but she's very good at it and her natural gravitas is toward things like that and systems and legal like she will read every word in a contract. I've never met anyone that reads every word in contracts. That was before AI, but even with AI, she'll still read every word even using AI.

70:32 That's the person that should do that, right? So, my point in that is that what I mean by liking working together is actually more of like, do the two puzzle pieces fit together and are you getting all the other p- puzzle pieces to have a clear picture of what the seam looks like and what they're going to achieve? I think a lot of people don't enter these uh relationships and these start these businesses with enough consciousness of who and what not who but what do we need to win?

71:02 And do we have it? And that's actually what you want to do with a co-founder, right? Like do you have what you need to win with the people that are around the table that are working on this thing? And when we start logic-ing that out, the easier answer is no co-founder and find people who you can literally pay to work as early team members that are part of the founding team. Yeah, be generous on equity and this and that but you're not picking someone or finding people who would co-found with you.

71:32 You're finding people who have functional roles that you know you need in the business and can deal with the ambiguity of a startup. Let's talk about winning in 2026. Our have a lot of things changed in your own mind for how startups founders should approach winning now with you know the boom of AI, the tools, etc. than like our fundamentals still true or have they changed a lot? Yeah, you know I'll give you um I'll give you three different perspectives. So, the first perspective is my classic one on this that um So, back in the day I learned lean startup from Eric Ries and Sean Ellis.

72:18 I'm adding Sean Ellis cuz I think a lot of the principle that he that he shared around how you learn faster in that loop cuz there the loop is like build, measure, learn. And you're going through that loop as fast as you can. It his learn part was very strong um and more than just tactical strategic because he was a marketer coming in thinking about it. The reason I'm mentioning that is cuz Eric was an engineer Eric Ries or is an engineer and founder and so he was on the build side.

72:51 And measuring is like a combo of both, let's say. So, there's build, measure, learn. So, the number one thing of three on what change and what I think we need to do is that there's this loop. Whether you believe in lean startup or not, every business is going through that loop. They're building something, they're measuring it, and they're learning, and then they're building more. Right? So, now if you think about that loop, >> [snorts] >> what's happened with AI?

73:18 The first thing that that's happened with AI is we can build more. You could argue and tell me, "No, we can build faster." True. Okay, we can build >> my argument. Yeah, but but even in the lean startup, it says build faster, measure faster, learn faster. Like that's actually the words. Fine. You can build more and you can build faster. We'll take I'll take the win there. But just because that's faster does not instantly make measuring faster or learning faster. So, I think the issue we're dealing with is this has gotten faster and we can do more. These other areas haven't yet.

73:53 And the smartest people that understand this that I've seen have made the learn faster faster. Yeah, I feel like with AI you can learn faster, too, right? Not to the same extent as coding faster. Who are the smartest people who have figured it out? So, uh the folks at Gamma have basically there was one tweet uh uh that was based on the podcast that the founder was on with Lenny.

74:27 And it really got me because it really demonstrated this loop and how they're going through it fast. So, what they said is in one day they can validate or invalidate a new idea. And the way they do that is someone has an idea, prototype it in the morning, build it, go do user testing and stuff like that, which is measuring and learning it, and get data by the end of the day on a new idea. >> So, what did they do to learn faster?

74:53 They just They just are in the mindset that we have to learn faster, and they optimize their processes. That's >> Because I think they realized this problem in whatever way they did. Yeah, now we have a bunch of code builds, but We can build faster, but we can't learn. Yeah, you got it. So, then you have a backlog of learning. Well, before you had a backlog of building. You still do. I don't think they code faster I I think we're still like code more and not code faster. But, that's okay. Like like it just looks like it's faster, but we have a lot of There's a lot of brilliance, hallucinations, issues with how we do. I mean, you know, again, not to pick on them, but I like picking on them, I guess, for now. Claude. They launched Claude co-work. Oh, yeah.

75:30 >> They built it in 10 days. It was vibe coded. I call it that, but essentially. But, Claude code wrote 100% of the code. Guess what? As a user, it shows. Yeah, I saw a couple a couple of articles of what the what task does score can actually get done, and there is a lot of errors or a lot of misunderstandings. >> that AI built the code. Whether that's good or bad for Anthropic, completely different story, but when I think about it that way, it demonstrates >> and the product, yeah.

76:03 Guess what? They built faster, they didn't learn fast. They didn't. You could argue they did, oh, they shipped it. You could have learned You could have learned in a lot of ways without shipping it the way they did it. I would have developer preview Not developer, I would have like knowledge worker previewed it, or some kind of preview like that instead of the way they did it. It is really It [snorts] almost I'll stop on picking on them, but like it almost does them a disservice.

76:30 It's basically saying that Claude code writes code like this, but it writes it fast. Okay, now what are you going to do? And that's not even speaking to the tech debt in their core product. You could feel the tech debt in their core product if a product person and use it. This is why I churned. Like they don't want to build this for me. It doesn't feel like it. Well, ChatGPT does. What am I going to use?

76:52 And Gemini, they're just going to throw features at it cuz that's Google's way to kind of feature their way out of the problem, very Microsoft style now. Which is fine because I'll use all the tools they give me for free or paid or whatever because they're very powerful, but they're not the same as these. So, I would just say that some companies have internalized this, others have it. And and that leads to my second point. Cuz I think the second point is that the way we think about speed is almost upside down.

77:25 So, and it goes back to the loop and all this stuff, but like I think it's very impressive that Anthropic shipped Claude co-work in 10 days. I think it's completely impressive. What's not impressive is the stuff I said, right? So, we're now at a weird place where we can ship faster or sorry, ship more. But if it's faster, that means that we're able to learn faster, but then what we do about it matters. So, I think our discipline in product development and this is going to sound really weird has gone down as more things are able to be shipped when I think the discipline should go up as more things are being shipped. And the discipline is around hey, learn faster, but point number two is point number one is basically just cuz we can build faster doesn't mean we can learn faster. We need to fix that.

78:18 That's like one thesis for this year. The second thesis is everyone needs to ship a heck of a lot faster than they are today. Cuz we ship or we die. So, I think last year proved and and and the company I want to give a lot of credit to here is Perplexity. Because they shipped their brains out is what it felt like, to the point where everyone had to react. Like, the reason ChatGPT Atlas exists >> Mhm. Because of Comet.

78:46 >> Because Comet existed first. And yeah, it's not like this idea was novel by any of them. Cuz Daya and the browser coming, fine. But like, look at that. And now what? Cuz these browsers matter? Should ChatGPT have Atlas? Should Preplexity have Comet? Like I ta- taking a If I were the founders, if I were the product people, I would consider shutting those two things down. Because it was built fast. It was built in last year's world of building fast. This year's world of building fast is different. Build fast and make it valuable.

79:21 Last year was just build fast. Cuz Preplexity was never trying to make anything valuable at the time. It felt like, at least. They were It felt like they were in a weekly uh product cycle where they would invent something on Monday and ship it by Friday, or ship it by the next Monday. And they were going in this loop. That's what it felt like. I've no idea what was going on. But as a user, it felt like that. In the market, it felt like that. But I think that pushed everyone to the point of trying that.

79:48 And I think we don't just have to try that, we just have to do it. Mhm. So, at Crazy Egg, we ship something big every month. And big meaning either it can be on Product Hunt, or it's a significant feature for existing customers. And that's just a mandate. And yeah, maybe we'll miss a month. I hope not. This month I Last month we didn't publicly talk about it, but we shipped something very significant to our paying customers. We just didn't want to make it free. So, we didn't put it on Product Hunt or make a big deal out of it.

80:16 Ironically, it's funnels, and it's the same thing we built at Kissmetrics. Um and this month we're going to ship something else. If I could help it, I would want to ship that size thing every week. Because if you don't have the attention, you don't get the customer. And that's the world we live in now. It was always like that, but now getting that attention requires you to ship new stuff. Cuz the only way to get attention is add value. Like an ebook does not add value. A post on LinkedIn does not add value in this way. It's to a customer or a potential customer. The thing you shipped does. Cuz after demonstrating that, if you're doing it well, which I don't think Perpetual Notary did, but we heard you.

81:00 We learned you needed this, and we shipped it. And here's why we think it's the right thing to ship. I think we need to get that disciplined. So, I think we need to ship fast, but we need to go from undisciplined shipping fast to disciplined shipping fast. So, just to reiterate for um for anyone listening, so point number one, we need to learn faster. Like sure, we can build faster, but learning is kind of slow. Two though is we need to adjust to the speed of how fast we can build things because they're much faster with AI tools. Right. What's the third one? Yeah, the third one is I think the the third one is more personal to me and how and what I would say is the state of startup knowledge.

81:48 And what I continue to see is that all the basics that I thought were codified and deeply understood, when I talk to a first-time founder, they are not. And a lot of the things that I created or guides or internal documents or or things like that, I will send to them. Like hey, here. Just do this. Like don't go talk to 15 people or find some consultant or that. Just go yourself. Do this thing in this document, and it'll work for you.

82:24 That's kind of like like like somebody I I they've seen a few of these for me and somebody's like, "Oh, you know, that's a secret document network." No, I'm like it's just the way to get someone to understand something that I feel like they already should or already should have the knowledge that this is the right way, but yet they're questioning it. Not even what I sent them, but it's just generally how do I do this?

82:44 There's answers everywhere. Why do you think that we haven't caught up to the right way to do things to all the playbooks? I don't know if it's caught up or or fell behind. Like like meaning like I I don't know if we need to like meaning the solution I don't think is catching up because that's what I felt like we had to do back in the day. I think it's relearning. Well, why did we lose the knowledge then?

83:08 Uh tech became an industry. Versus a craft? Yeah. The craft of startups does not exist right now that I can see. Maybe in pockets. The amount of companies that are run by folks that don't know what they don't know is the issue. And then investors aren't telling them. Investors would do it back in the day. But coming back to growth though, is it I guess yeah, it's important to know things so that you can repeat things, but if you're a startup that's just like, "Okay, you know, we're growing, we're printing money." Why do we need to care to pause and figure out how to do things right? Because they might break at any point of time?

83:49 I I think like it it's it's a good question. I think this goes back to people's mental model and even that thing I said about, you know, pre-product market fit and the shift of the heat and bombs to post. I think what happens is the mindset you use to start the company is not the mindset you need to scale the company. So, the mindset they might have used is we can do everything our way. Okay. Cool.

84:18 At some point your way won't scale. Do you know what areas it won't scale in? Do you know what you need to do to make that thing scale? A lot of a lot of the common one is like most of the companies until they hit like hundreds of people, some of them, not most, they have flat orgs. But then things don't get done. And then they wonder why things didn't get done. They felt basic. Well, it's cuz you made the org flat and now it's hundreds of people with a flat org.

84:45 With no real key of who reports to whom. There was this concept called holacracy day. People tried all kinds of funky things. And then what are we back to now? A hierarchy, an org chart. And in fact, we should be embracing it even more because there's so much talent out there that fits in the org charts. Why would we tear up the org chart for no reason? Yes, reviews and all that and big company stuff, I'm not into that. But you still need structure and people need a mental model of who do I go to for X, Y, or Z. You have a flat org, you don't have that. But you can do a flat org for a certain amount of time with a certain amount of people. But that's a good example of like doing things your own way. I I it reminds me of a couple of times I listened to the episodes of Acquired that were about older companies, like companies that started a hundred years ago. Yeah, exactly. Or like Costco. And I was like, damn, they innovated on a lot of this org stuff a long time ago cuz I feel like in the valley because it's all about innovation, innovation of org structure, or how we're going to do a sitting plan, or how we're going to do reviews, the mindset is always be experimenting and innovating. But it is true that there have been very significant uh s- learnings throughout like a year hundreds of years of building companies that actually work and they're already proven to work. So it's like why reinvent the wheel? I I just caught myself thinking that I didn't know that this has already existed and been proven for years and years and it's not like a Silicon Valley innovation. It it it's Having worked at a very large company, very large being large, not very large, like 3,000 people, um I can totally see and really deeply respect why some people who had experienced that don't like it and don't want to do that in their own companies.

86:38 But having not had that experience first and instead had the only experience of trying to build my own, >> [snorts] >> I look at what they're doing there and I have a different perspective. You don't want to bias towards thinking that scale causes issues when really environment causes issues regardless of scale. So there's something that happens in those environments that lead to the hierarchy and the structure being abused.

87:10 While you could build the same hierarchy and structure not abuse it. And make sure the culture is right. So you go back to environment and culture versus I'm going to have a flat company or flat org. Cuz at some point like here's the problem, like everyone wants to make more money. Like not everyone, but like in general if you're working in a tech and you're an employee and you have a role, you want to make more money.

87:36 The clarity of how you do that To move up the ladder. is really important. I felt like working in a larger company too many of my conversations with my colleagues were around these kind of things. Because they lack clarity even with all the structure that existed. Or they didn't like the clarity. That's a different story. Like they didn't like how it worked. Okay, cool, start your own company, it's fine. I did that, right? Um but so I think like when you think about like this, we throw away things for the wrong reasons.

88:07 And one of the things is org and hierarchy and all that. But I also studied org behavior in college. I made my own major. This is things I think about probably more than most founders. Simply because like it it just comes naturally now, but like >> [snorts] >> you know, I used to love to say this. I could walk in a company and and walk up to someone's desk and find out everything about the culture by asking them one question. And that question was simply what are you working on and why are you working on it?

88:36 Yeah, you'd be You'd be surprised how many people don't have a clear answer. Or they especially the why part. >> say cuz my boss boss says so. Which is fine, but but certain type of culture versus because this is the biggest problem in the business and this is the metric I can move to help with that and so I'm focused on this thing that helps with that. That That is a better answer. That is the answer I I wish more people would have in the world. Cuz if they have that answer, then we know there's less dysfunction in the organizations.

89:08 I want to come back to you deciding to take a job and selling your company to Dropbox, but while we're on the topic of, you know, being a founder and um and how the world has changed, how should someone listening decide what to spend their attention on? Um they might want to start a company, they might not want to start a company. Like in a world that's changing so fast and there is so many things happening, how do you decide what to spend your time on and what advice can you give to listeners?

89:38 I think the micro the micro way that I would describe how you discover the answer is is probably what I would suggest. And then we can talk a little macro or broader. But the high-level before I get into that is it has to be contextual. So that's why the micro thing I would say is I think you and I have talked about this, but it's like at some point I realized that like I need to focus on what gives me energy.

90:10 So, all you want to do really the first answer that question is like what gives you energy and what takes it away from you. And also like in some cases what's the neutral? There really isn't neutral. Cuz good is neutral. So, what gives you energy? What takes it away? Cuz sitting here is neutral. But am I like after this, am I going to have more energy? I can already tell you the answer is yes, because I've talked with God I've spent time with you and I like talking to you and we like hanging out and talking about this stuff and now we're doing it on camera. Fantastic, right?

90:42 Um and that's good. But I know that, that's why I'm doing this. That's why I said yes, right? Um while other things like convincing legal to let me ship a product did not give me energy. So, you know what I did at Dropbox? They were already into this and kind of doing it, but I was a product manager, but I took I took myself out of that room and I made the engineers talk to the legal and compliance people cuz I realized one doesn't give me energy. As in I have no problem with the legal people. I'm happy to jam on it, but it's not doing anything for me, which means it's probably not going to help the business. So, if I can get out of that, I will.

91:24 But what I also realized and this is what I mean by the nuance, I didn't care about why it wasn't giving me energy because that wasn't as important. I was like, okay, how do I solve this problem so I don't have to deal with it. What I realized is the vast majority of what legal says, engineering has to do. And the way I was operating engineering at least as a PM cuz I had no reports, but the way I was like working with them was they have ownership I wanted our team, the engineers to have full ownership over the code they wrote.

91:53 So, the way I did that is I got out of the way and they knew when to come to me when they needed a decision they couldn't to on their own. That's generally how I like to manage, but that was kind of like the the the situation that I sort of developed. But that micro like thinking, and I say it's micro because you asked a macro question. But I would go micro because that's how you determine those things that give you energy and don't. Like for example, some people are like, I need passion for the idea or whatever.

92:28 For me, it's actually I'm passionate probably the wrong word, but I need conviction in that that the people I'm working with can help us achieve our goals. I don't care what the goal is. I don't care what the business is. I don't care what the idea is. If I feel good about who's around the table and our ability to work together, I'm in. Don't care what it is. We could be building anything. That's kind of my mental model, but I know what gives me energy, which is the people I work with.

92:57 Nothing gives me more energy than the people I work with. And I know that. That's me. So if you just figure out what gives you energy, what doesn't. Like some people are like, I just want to code all day. More power to you. If you can find a situation where you can do that and that gives you energy, that's what you should focus on. So I think as humans, we have most of us a lot of us have so much privilege so to speak where we can make these choices like this where we can decide to analyze this and make a decision and do more of what gives us energy if if not just do only what gives us energy. So I think I'm trying to optimize for doing either neutral things, which is nothing, or going straight to what gives me energy. So the second I see it, you could call it vibe, you could call it whatever, but second I start feeling those bad vibes or this I'm losing energy, I'm like, "Okay, what do I need to change?"

93:45 And it wasn't that the legal people were giving me bad vibes or anything. It just never gave me energy to like debate them or do that, but I was always willing to make a choice if they had a choice for us to make. But usually it's like copy or this or that or really small things that like I can't even help with much cuz it's dictated. Which means the engineer just needs to go implement it in a box effect. If there are deeper things, they'd come to me.

94:08 But, this whole system was out of hey, that doesn't give me energy. And I used to think oh or or not me like my co-founder actually would came to me like oh, you don't like them? Like no, no, no. I actually love those legal people. I love all that. But, like the process doesn't give me energy. And someone better than me can do it, which is the person who wrote the code, who is working on the thing that needs to go appease these people. We all do, but and make it so we can ship the thing we want to ship. So, that's just a very work example, but like you put that example around everything. You even think about like a conversation you're having with your partner.

94:41 Is it giving you energy or not? It's your partner, so there's probably some kind of rubber band leeway, right? Stretching leeway. But, at the end of the day, the more conversations you have that don't give you energy, the more you're probably not going to like that person over time. Like I'm just being honest, right? And if it gives them energy, it doesn't give you energy, that's a mismatch. Cuz a lot of times these conversations give one person energy and not the other.

95:05 And it's not a fight. But, people don't realize it. And then later on they part ways. But, it was usually cuz of the erosion of that. Yeah, 100% I think it goes back to what we started with just the time to reflect on how I feel about certain things, certain people, things that I'm doing. So, to summarize to figure out what you want to do day-to-day is try a bunch of things to figure out are they giving you energy, are they not giving you energy, is it neutral, and then do more things that give you energy. Exactly. What about macro?

95:34 I think macro um and this is my third thing. We didn't even get into the third thing fully. >> we did get Okay, we partially got into the third thing. It does relate to the third thing. I think the macro is that Oh, the third thing was about the startup fundamentals. >> Oh, yeah, there we go. Yeah, yeah, there you go. So, this is a >> This is >> the fourth thing. >> Yeah, this is not the fourth thing, but it's adjacent, but it was what I wanted to get into with that, which is relevant here, which is like basically um the amount I I don't think and I've had a computer since I was eight.

96:11 And I don't think the ch- I don't have the why or the answer. But, I think we are generally all dealing with uh existential crisis. 100% >> that nobody understands. So, when you ask that question about macro or or when I go macro and I try to break it out to micro and macro, I would say there is no macro. There's no macro right now. Because there is an unprecedented amount of change that is coming.

96:43 We are uncertain about what's going to change, how it's going to change, or why it's going to change till the point where all we're doing, the people who have the means, are investing in it in one way or another, whether it's the companies investing all the data center stuff, the chip It's almost like investing into dropping off off the cliff. Even even earlier today, I was talking to a friend, and he's like, "Everyone except one investor of mine doesn't understand why I'm burning cash on AI to build AI into our products."

97:20 Like, yeah, well, that investor probably doesn't understand what I'm saying here, which is so existential. Either you invest in that or you're investing in nothing. In tech, you're either investing that or you're investing in nothing. That mean that could mean that your product has nothing to do with AI, but the way you're running your business has everything to do with AI. Yeah. >> Like, that's just where we're at. >> Yeah. Right? So, that's the case that we don't know what we don't know.

97:46 And no one knows. I mean, we have investments like like in the world in nuclear now and chips. Like the president's coming out and saying, "No, no, your electric bill go up." Like, what? Like Microsoft coming out and saying, "No, no, we won't let your electric bill go up." Like, these are the things that are Wait, what? Like like think about it. Like you're talking about electricity and corporations sucking up so much electricity that the constituents in the country are worried about the electricity bill.

98:19 Could you have predicted that 3 years ago? I don't know anyone who could have. But and that's just like one real nitpicky thing I'm going after, but like how many of those exist right now? So, how much uncertainty does all that kind of stuff create? So, I think the idea like I honestly think anyone who who has been a founder This is why a lot of the founders are coming back, I think, and re- and doing stuff because we are very good at dealing with change.

98:48 If you've done it once and you see what you're seeing out there right now and you're like, "Oh, change? Bring it." Right? You just have to have the click of why. Because you might be retired. You might be like Sergey who needed someone to tell him, "Hey, you're a engineer. You're a computer scientist. You're not a You're a founder, but you're computer scientist first. What the hell are you doing sitting on the sidelines? What a kick in the ass.

99:12 Like I got to say. Right? I mean, I assume it happened cuz he said it happened, but like man, if these people are starting company or not starting, but are investing their time in their businesses like they haven't for forever. What are all of us doing? Like what do they see that we don't see? I think it's very simple. Founders are very good at change. So, we should be doing things where we are trying to figure out what the changes that's happening and make impact somewhere. But where that is or whatever, I think you have to find it in the microwave because there's so many options and there's so much change. And it's likely that like for example, even with Claude like the co-work thing like a lot of people have already came out and said, "Oh, there's so many startups that are killed because of that thing."

100:06 Yeah, but they built it in 10 days. If your startup is killed because of something Anthropic could build in 10 days or five code 10 days, you have a problem. You didn't know what you were doing in the first place. I'm sorry. There's caveats and there's edge cases where it's a real problem cuz you're building the exact thing, fine. That's a different problem, but it's still a problem. Maybe you shouldn't have been building that thing. But like, yeah, like that's the world we live in.

100:29 And that's Anthropic. Like we used to say that about companies like Google. When they ship something, oh no. This is Anthropic like they're not that old. Now they're massive. They're one of the top companies on the planet right now, but they're not that old. Why are we scared of them? They don't know anything special. Like really, they're not scary. I mean legit, that company is not scary, but like why are we saying that oh social media and Twitter and amplification of whatever. Okay, fine.

101:00 They haven't killed anyone. They're not going to kill anyone. Like we all have like if anything like again, I'm very bullish on AI as a lot of people are for reasons that are like, "Look, if Google is putting AI in front of consumers and ChatGPT is or OpenAI is and Anthropic is, that's only good for us cuz that means more people are getting used to how this stuff works." For anyone who is not in a founder mindset and is actually scared of change because that is a lot of people too, how do you stay grounded in so much uncertainty.

101:38 Um Okay. So, the most cliche thing I can say is focus on what you can control. I think the reason founders are good at change is because they've gotten Got to control a lot of things. at at figuring out what they can control, figuring out what they can't control, and figuring out what they could control. The could control part is the secret. Can, cannot, easy. Could is where you go, oh, if I do this and that and this, you know, the scheming entrepreneur of all of us, but then I can control that thing. Sure.

102:12 That's the art of entrepreneurship is figuring out what you can actually change to make it so you can control it. So, that would be my like sort of way of thinking about it, which is like, hey, look, if you focus on what you can control, then you're not going to be so scared of everything. If that changes, hopefully you you discover a way to kind of iterate and improve that, right? So, that's my one answer. I think the broader question that I would have for someone who's feeling like this is, why are you feeling like that? And then I would get into all the all the stuff of like, well, again, just to go there for a second, when was the first time you felt like that?

102:55 And I would just walk through like, what is it that what is the something, what is the story, what is the trigger because as much as we believe everything's going to change, I'm sitting on a couch in a place that like like >> That hasn't changed. It's like, where's my flying car? What was the case? The microphones are better. Cool. The cameras are better. Yes, they are. Amazing. Um What has changed? Right. Fundamentals have haven't really changed.

103:27 >> have to live our lives, still have to eat food, we still have to survive, we still have to make money for now. Yeah, there's people saying we might not have to make money in the future, but >> Oh, really? Is that happening? AVI or whatever what is it? The abundance. UBI, universal basic income. Hey. Hasn't happened yet. >> Someone else's problem to figure out. The way I think about it is if there's a line of sight to that, great. Otherwise, why are we worried about it? I can't control them. Right.

103:52 Okay, let's come back to Hiten's journey. So, why did you decide to go to Dropbox? And give me some context. So, you left Crazy Egg and it was still running to start or was it or like a side project? >> I left Crazy Egg to start another analytics company called Kissmetrics. So, I left back then. >> Yeah. And I haven't worked on it until literally last year. >> But was it running still? >> Yeah, my wife was running it.

104:13 >> Okay, got it. So, it was running self-funded as business for 20 years. Wow. >> Um and then uh basically the main reason we sold the company and wanted to sell it is cuz we noticed that we were at what I call a peak of value. So, it's like a crypto chart. Goes like that, you figure something out, it goes here. If you're at that peak and it's a real peak, you're somewhere in the curve. >> Yeah, yeah. And it's not dropping, it's going to drop. And then you're going to have to find a way to get it back up.

104:46 And that is every company. And that part is the hardest part. This part we think is the hardest part, but it's when we figure something out and it and it stops working. Or or or you can just see that. So, we were at a peak of value. >> Kissmetrics? No, this was >> Neuro. Okay, okay. Wait, so what happened to Kissmetrics at that point? >> um we had a journey. I left that company and didn't want to do anything else. Um we we were one of the first to have like privacy class action lawsuits and stuff.

105:18 >> That was when you decided to take your reflection break to figure out what you wanted to >> or less. Yeah, and and um CEO took over and stuff like that. I I helped replace him as well and went back in for 6 months and came back out. Uh and then kind of haven't touched the business since. Uh other people are running it and doing it. It was venture backed. Uh then I took a few years uh and that's when I met my co-founder for and we were actually first building for lack of a better word a Gleam competitor. So, enterprise search tool.

105:50 Then we realized that IT and security actually had a bigger problem. So, all pre-AI. Uh and so we started focusing on that and then that turned into Nira cuz we rebranded. Uh and then um yeah, we were just at a peak value because the things we were doing were just about to start becoming important to enough companies. And the reason for that is we were basically protecting company documents from unauthorized access. But, we built a tool where even if you had 100 million documents, you could see them in our tool as a IT or security person and see all the permissions.

106:24 And with a couple clicks, you can find a million of them. Couple more clicks and you can change all the permissions on them, right? Like if something has a public link, make it restricted, right? Well, AI came around. These chatbots had access to all the documents. So, if you're a company that doesn't have transparency, which is most companies on on like salaries, then someone could in theory type in what's my boss's salary and get an answer if they had access to the wrong documents or documents they shouldn't have access to. So, because of what we were building, it really fit in line with what people really even today still need before rolling out like AI tools.

107:07 But then, so the company reached peak value, but given you were always a serial entrepreneur controlling your own destiny, why did you decide to cuz I'm sure you could have negotiated it such that you didn't have to go work at another company? >> think that um Was it curiosity to explore what big orgs were like. I think it's very hard to work out at the at the earlier stages a situation where your uh you're not coming with the company.

107:33 So, that was one thing. So, yeah, it was might have been doable, but I would have still had to spend some time. So, instead it was just easier to like not make that an issue, right? Because it wasn't like anyone on the other side of the table at the time didn't know that I've never had a job in my life. They all knew it. >> [snorts] >> So, no one was coming in like, "Oh, this crazy person's going to come here and be crazy." They were like, "Oh, this crazy person's going to come here and they're going to be crazy, and we know why."

108:04 Right? Um but thankfully I was able to help recruit my boss. Um I would uh you know, I've never worked for anyone again, but I would definitely work for him again. Uh I don't wish that upon him though. Uh or or anyone else, but I'm I think we did okay. Um but like basically companies don't founders don't realize when they're at a peak of value. And and when you have investors on your cap table, you can either you know, say, "Hey, look, this is an experiment.

108:37 We're going to keep going and like try to make it big." Which we could have done. We had 18 months of runway. >> [snorts] >> But instead, we were like, "Well, the way the previous year went and the year before that went pointed to um the kind of work we would have to do to transform the business probably once again, to be honest. Because at that peak of value, there were just things we had to do to service that even better, make a bigger stink out of it, blah blah blah.

109:09 Um that we could have done and we were going to do, and those were our plans. But then if if someone was going to come come along and help help us get to some of those goals faster, it made more sense since the peak of value meant that we were going to be in a slog. And we don't know if we'd raise the next round considering the slog and the way the markets were. And in hindsight, the best decision was actually to sell the company.

109:39 Because so many things collapsed after in the world and they were already collapsing before cuz growth was very hard in 2023 uh cuz budgets were collapsing at the time. And so an earlier company doesn't have as much uh stability. We had enough but not enough to say, "Hey, if we go to the next 18 months, we're going to get a series B B for sure." And so between the peak of value and that calculation it made more sense. Yeah, so it was just that self-awareness that it was better to sell. Yeah, and and it's also like doing what's right by everyone around the table. Whether it's the investors, the team members my co-founder and myself, etc. And like that the funny thing is when you raise money in this world so startups, tech you're supposed to try to make it big. That's the point.

110:39 Otherwise, go self-fund the company. Especially with white coding all that, you could do that and and not have to raise any money. But if you raise money, it's go bigger go home. And if you don't know that then you're not going to think about these businesses correctly. So one way would be like, "Oh, YOLO. Let's go the 18 months and just try to figure it out." And no one was going to stop us. They didn't even have the ability to, mostly.

111:01 Or if we can get the right deal, the right price, the right, you know, reason to sell, whether it gets realized when you're over there is another crapshoot. But the right reason, which we're all right, then like if we found an opportunity to do that, we should do that. So that that's kind of um the full calculation. >> picture that happened, but really it's just peak of value. If you're at a peak of value, your job should be try to capitalize on that peak of value regardless of anything.

111:33 Like even if you want to go public, like you're at a peak of value, like you should entertain like like what are you worth? Or what can you get away with? But of course, if you have high enough conviction or have a calculation where like, "Hey, I think we can get past it." Sure, go for it. Like we had ideas. We probably probably had a 50/50. My co-founder might say less because she's more conservative, but I think it was a 50/50.

111:54 That makes sense. Especially knowing what I know now. Like more conviction on certain things, you know. Okay, I in the interest of time, I really want to dive into the topic of personality tests um since we haven't and that's a very interesting topic. So I was very surprised to find out that you're really into human design, which I feel like is kind of niche, uh and then enneagram also. Tell me more about why should someone care about these frameworks and how to effectively utilize them for your own self-improvement.

112:24 I think people who have very clear goals that they've had for um forever and don't have a reason to deviate, don't need any personality test or any of that because I would make an argument that they might not have much of a reason to try to understand themselves cuz they don't they are probably not going to perceive a problem. But I feel like sometimes goals change. You might feel like you have very clear goals up until a certain time and then something happens and then you start questioning. So I think the start questioning is when you go down personality test I just wanted to make that clear because people listening might not realize why they don't care about this. Or maybe I this this makes me think of if something's not broken, why dive into a lot of you know, self self-digging? There's people close to me in various ways that will never care about this stuff.

113:24 And so I just wanted to address them first. They will just not care. And the only thing I can think of is or not think of the the reasoning I would have is their goals make it very easy for them to feel like they understand themselves well enough that like they don't need to entertain. But you are right. The second that gets tripped up, this can be helpful. So on those people cuz I'm kind of jealous of the person who's so >> [laughter] >> so clear about their goals, are they very like are the goals very simple goals, very clear goals, or not really? Like what's the archetype of that person?

113:59 You know, it's really weird. The people I can think of, they know themselves so well that they don't think about knowing themselves. So if you ask them, do you know yourself? They're like, what do you mean? Like literally they can't even compute the question. Because that's not how they think. >> know themselves? Or do you think they're so convicted that they know themselves, but it's not actually true? I think that they haven't found a value in knowing themselves better.

114:30 >> Better. Okay. That's fair. But then you know, if you find a value >> matter. If you find a value you're digging in to your point. Like they have a problem, so the value is I got to solve the problem. I got to solve the problem, so they'll find the value in the in trying things to solve the problem. This is why people go on the ayahuasca trip, all that kind of stuff, right? Like similar thing, go find myself. It's like you're right here. You don't need to go find yourself. You are right here. You don't need anything.

114:54 Anyway. Yeah. Okay, so for people who are very clear, they know themselves, this is, you know, skip this section, not important. Then for you can >> you know yourself, or you don't care, right? For this it's fully fine. So for for in in general the this area is very simplistic for me and again it probably goes back to personality which is simple. If I can get information about myself to help me understand myself, I just want that information. I don't really care where it comes from. I don't really care if it's esoteric.

115:28 I want to try it. I want to see and if I get value from it, it's my job to get the value. So my co-founder taught me the statement that someone taught her which is take the best and leave the rest. So Marie taught me that and like sometimes someone will say something to me about something like dude just take the best leave the rest. Like you don't like what I said or you don't like some part of it? No problem. Is there some good in there? Yeah, okay, great.

115:50 Take that. You want to talk about it? I'll help you. You want to ignore all of this stuff? I don't care. Right? Like so I think with some of this stuff folks get very caught up in the how does this thing know this? Yeah, yeah. Instead of what can I do with it and does it resonate? So I think a lot of this whether it's human design, enneagram MBTI, uh In-color Insight is another one. There's a bunch of these.

116:17 All of them in one way or another help me understand either myself or others and then as a result of that help me understand relationships. Mhm. And so in your experimentation your favorite ones are enneagram and human design. >> Yes. And how much time do you just spend on each framework that you touched to figure out whether there is value? I guess there was some scientific process involved in figuring that out. No, it was more bumping into things and trying them and seeing if I like them. What's an example? Human design. Like what's an example of how you would Give me an example of something you learned from human design and you running an experiment to figure out whether >> Oh got it, got it. Um >> [snorts] >> I think Enneagram's interesting on this one. So, at Dropbox like um in the internal uh uh the we had an operating system thing. So, the internal operating system that had a org chart and a bunch of other stuff.

117:16 Um there's a field for your Enneagram. Cuz he Drew really likes Enneagram. He's an Enneagram 7. I think it's out there. Oh, I'm an Enneagram 7, yeah. And [clears throat] um I'm a 9, and my boss is a 5, or was a 5. Do you believe that just interrupt you for a second that you need to look at the primary Enneagram? Cuz you know there is like three top Enneagrams. Is there any value? Cuz I'm a primary 7, and then I'm a 9.

117:43 >> a wing, yeah. Uh maybe for yourself it's more helpful, but it does help because it helps you see a bias. So, you'll bias one way or another, right? And there's also a triad type thing. Uh like a three, a six, and a nine. It's funny, my brother-in-law's a three, my wife's a six, I'm a nine. Like um >> Okay, so Drew really likes Enneagrams, so at Dropbox you guys were really into it. >> had Enneagram. So, it was like it wasn't like I wouldn't say like it was cultural, but I'm sure at some point it was.

118:12 Because we know his, a lot of people will put theirs, I put mine. Slack instead of the, you know, circa 2019 pronouns, you put in your Enneagram. There you [laughter] go. That's the new thing. >> I like that better. >> Uh yeah. And so, basically I had ChatGPT ChatGPT set up where I could go and be like at one point um because my boss is someone I've known for 20 years, the time we would get on a one-on-one or call was very precious cuz like we both valued it, even if there wasn't much to say. So, we tried to do it, but he He a VP, so it was very hard, right? And I even told his EA at one point, maybe more than once, "Hey, if it's 1:00 a.m. on a Saturday and he can make it, I'm fine. Like, I'd love to talk to him.

119:01 This is one reason I'm here, right? Probably one of the bigger reasons, cuz working him with him was incredible. Um I learned a lot and I didn't even think I'd learn anything, not from him, but from generally that experience, but or I didn't think I'd learn things I would take with me in the way that I am, is what I should say. >> the biggest thing you learned from him? >> Um There's a lot of things I learned from him. I think I learned more about myself from him by him managing me in the way he did, because it helped me understand things about myself that I quite didn't click on. I'll give you a couple examples. One I was getting into, which was at one point our one-on-ones, like we weren't we didn't have them consistently.

119:44 And and you know, there is one mantra, which is like if if you're managed by someone and you're not having one-on-ones, one one mantra is like, "Oh, they trust you. You don't need to have them." And that was where it was at, right? But I wanted them cuz I wanted to spend the time with him. And I know he was fine with that, because he he wanted the same, but it was very hard. So, one point I hit ChatGPT, this is after like 6 weeks or something of no one-on-ones, but we were in other meetings, everything was fine. I'm like, "Is everything okay?"

120:13 Like, I'm I'm a nine and I'm like just trying to align and, you know, my human design it knew, so it knew what I was looking for, very clearly actually. So, he's like, "Oh, yeah, yeah, you're fine." I'm like, "What do you mean?" Well, he trusts you and these things you're telling me about the signs are essentially him trusting you, right? So, don't worry about it. And obviously it was true. I wasn't really worried about it, but I was just curious how it was going to explain it to me, how ChatGPT was going to explain it to me, because what What found is in this work, like the person personality and all that work, chat GPT is actually able to help me see things I couldn't see before in the same way or ever. So, another good example was like I started talking a little bit about how I built things there with chat GPT cuz I was like really curious about it. I'm like, "Hey, you know, I built things in a certain way. I thought about it this way."

121:10 Yeah, about 80% of it is what I would normally do, but there's this 20% like why? Like why did I think about it like that? Why did I do that? It came back and said, "Well, you're a systems thinker because of your personality and this this." And it went pretty far. I didn't even use systems thinking, but that was essentially what it was saying. And then it basically went back and said basically you built you built that way you built the products you worked on that way because you were in an environment where that way of building was the only way you were going to make sure you Basically, you were trying to make sure that whatever you built continues for a long time.

121:56 And it basically said the way you built those things was specifically designed around that need you had and what you saw needed to be done to make sure it last beyond your time there. I was And And like I can't dive into the specifics, but like because of Dropbox and not wanting to share, but it was like so spot-on about like why I built that way. And that way was not like it wasn't it wasn't To be clear, it wasn't the processes of building. It was actually the That's why I don't want to share but the output of what we built. It's like you built it that way for this reason. I'm like, "Holy crap, like you're right. I I subconsciously was building that way for that reason.

122:44 One thing that comes up for me on that is how to decouple it from decouple your reaction from being like, "Oh, you're right. This is true." from treating it as one of those confirmation bias things. Like reading a horoscope, you know, you can always find things that you think are true. Yeah. Uh and then getting convinced that the way it described the thing that you did to yourself is genuinely absolutely true. Um taking something basically for its face value. I think that goes back to what we all say now or starting to say more, which is like essentially the two words are judgment and taste.

123:22 If they give me some [ __ ] I'd know it. So, but that's my taste and judgment and I've spent enough time knowing myself without AI that like if it's Honestly, in that personality site, for whatever reason, I've never gotten anything not valuable or incorrect, in my opinion. But yeah, it can gaslight me, for sure, right? Like sycophancy, all that. Fine, fine, but like cutting through that, it's like, did I get value from understanding that? Tremendous amounts of value. Tremendous amounts, cuz now I'm like, "Oh, okay.

123:54 I don't need to build like that in other scenarios or if I'm building like that, there could be this hidden reason I didn't see before." I want to I I want to ask some really greedy questions. So, you mentioned at the very beginning of our conversation that you have this project set up that in ChatGPT now that understands you and I assume that it's based on Enneagram and Human Design. Tell me more about how this project is set up. This This is actually the one I use for these things.

124:18 Yeah, yeah. So, it's a project. What's in the project file? >> Yeah, so the project files are um my Enneagram. Like just the Like the instruction >> test. >> Like the instruction knows my Enneagram. I just told it nine, maybe a wing, whatever. I mean >> Okay, okay. >> Cuz it's AI, like you can put as much context in there. ease. so this is an instructions. It's not a file to be uploaded. >> is an instruction cuz there's not much more to it.

124:40 >> Okay, you're like an Enneagram 9. >> Well, and I assume the AI already knows about Enneagram, which is true. >> Yeah, which is true, yeah. >> But if I was using AI that didn't for whatever reason, like a local one or some whatever it is, even local ones. >> Yeah, let's just talk about ChatGPT. So, you put >> if it's ChatGPT or Claude or even Gemini, it knows it has that knowledge. So, I would tell it that. I would tell it my human design, and then I would give I the artifact for more like my human design chart.

125:09 Or any other context that I want to share in there, cuz it doesn't have my chart. Even if I gave it my data and all that, it's not going to go make me my chart. So, I want my chart, and but I can assume it knows about human design cuz there's a lot of publicly available material, tons and tons. Perfect, great. So, it's mostly things like that. So, if I had a MBTI report, any reports I had, my In-Color Insight, did that many years ago, I shoved that in there, too, even though it's kind of old and stale. Um Yeah, and then I would have a I had a chat, a long-running chat on that one, but I could easily have done more that was about checking like what my boss thought about things, but that chat I started with, this is his Enneagram, and in his case uh he built a manual. Like, you know, some people do the operating manuals, especially execs.

125:55 So, he built a manual. And that manual uh was what I used in the chat, not as project files, but in the chat be like, uh my boss is an Enneagram type five. This is his manual of how he thinks about it. I even had it first say, I'd love for you to interpret this because an Enneagram five wrote it. Like, you know, kind of like a >> Yeah, yeah, yeah. Yeah, right? And that was interesting. Uh nothing bad, just very interesting to see how it broke it down, why he wrote it.

126:23 >> Right. >> Which is stuff you might not understand, either. And so, that was cool. [snorts] But then it was like asking these kind of questions, or you know, that one um that one what I did also is I actually took his manual meter project for it. Okay, yeah. >> it was like it was like the Morgan bot. And then I was even helping colleagues, but like it was giving like such accurate Morgan-like feedback. That's amazing.

126:49 >> Because it was between knowing his Enneagram five and then knowing his and having his manual. And so now that you have this project with instructions and your human design chart, whenever you have more of a personal I you want or you have >> this where it says this. I felt like it kind of yeah. Uh-huh. Easy. Got it. Okay, that's awesome. Yeah. Okay, completely switching gears. I want to know how you post so much content.

127:14 What's the system? Yeah, yeah, there's no >> so many tweets, blogs. >> I need to do better on some of that. I'm going to. But the truth is it's lots of notes. Basically like I think there's a systematic workflow whether it's conscious or not that people go through around creating content. I I a long time ago I studied it cuz we were building a bunch of content stuff and wanted to understand it. And that's just studying like how how people create a blog post, like nothing fancy.

127:45 But that got me to a framework and um or some kind of thing which is like the key to writing the content is actually the idea. And one idea can actually lead to a lot of content. So there's almost a flow of idea topic content. Same idea, different topic, content, right? So that mental model made me realize that like I can pull up all kinds of old notes that I've written. Maybe even some of those after a meeting.

128:16 And it's gold and they're >> write a lot of notes now? What's your system for writing notes? >> I just use the notes app on And right now do you use voice to text? I'll I'll use voice to text. Sometimes I'll do voice memos. Yeah, everything. Now everything can just be shoved into AI to organize it, find insights, all that. So it's more about like to me it's more about capturing all the raw inputs. >> Got it. Got it. So you have a bunch of notes, okay. Yeah, and and then literally like when I write something I go look through the notes, find some sentence or statement, and then like figure out what I want to say about it, work with ChatGPT as needed, whether it's editing, brainstorming, deep research, whatever.

128:54 I'm just using it as an editor. I'm using it as a researcher and editor. Are you systematic about when you sit down to actually distill your notes to write content? Or are you Cuz for for example, one thing that I always struggle with is my desire for spontaneity and my desire for being systematic. And those desires exist at the same time. I'm not a very like I'm kind of in between being very routine-oriented and not. And so then I'm like, "Okay, I need to build out a system." I start with building out a system, and then I have this desire to bomb the system.

129:28 So like if you're good at spo- at spontaneously having an idea and wanting to just share it, then I'm skipping a lot of the steps in a good way, and I'm just posting it. So you're allowing yourself to do that. >> Yeah, like for example, after this I might walk away with some insight in just my mind, and I might just just post it and call it a day. So that's that's probably the main mechanism. I think the second mechanism is closer to what you're saying, but what I found with things like this, I'm posting X amount in Y amount of time.

129:56 I'm posting once a day. I'm posting once a week. I'm And then trying to just Essentially it's old-school content calendar crap. And it's forcing yourself to have that, and then sitting down at a like What what tools are you using for your content? And do you schedule content? I assume you schedule content. >> Uh I schedule content cuz I have to. Otherwise it goes out at any time, which is bad. Uh so I use Typefully only for scheduling.

130:19 >> Typefully, that's for Twitter or for anything? Uh Twitter, anything actually. >> Got it. >> I used to use Buffer. I think Buffer's a little heavyweight for it and Typefully really figured it out for Twitter where it it's a lot more intuitive the way it worked for me and it's less of a power scheduler, but it's very good. I don't use any of their AI features. I haven't found them to be very good. I don't care for them. But the raw scheduling, that's the one I use now cuz and I've tried many things over the years even back back in the day. I was one of the first 5,000 users on Twitter.

130:49 Wow. >> Um, we actually built a twit it was called twit this at the time, t w i t this for whatever reason, not tweet this, but we actually built a button before the button existed tweet this or whatever. Now they don't matter. Um, so really early there we even built a I had an engineer build a script, a PHP script when that was a thing to do scheduling. This is before Buffer and all those things existed. So something I've been doing a long time. Uh, is the short of it. But it that's for scheduling cuz that makes that easy.

131:19 And the majority of it is just whatever I I actually use deep research a lot. Cuz I find that to be really helpful whether it's Perplexity for some of it or ChatGPT or even Claude um, in order to get context or examples or help me validate something I'm thinking when I'm writing something bigger or more thoughtful. Um, but yeah, it's about sitting down and doing that but no fancy tools. Like honestly for the longest time before I jumped on Typefully cuz I wanted to cross posting, I would use tw You know Twitter has a native scheduling feature?

131:52 >> Yeah, yeah, yeah. Yeah. But now you also do video content, you've had podcasts multiple times. Um, what is the process there? For the video content, I found a team that iterates like it's a product. And so I we're still iterating, but we're getting there. Uh, now you know, with my lisp and the voice, uh, we're working on uh, some stuff where we can fix that problem uh, in the content. Um, so that I've been looking for this team for a long time and they just happen I found them a couple years ago and really enjoy working with them. They're also working on like I have a daily operator length newsletter right now. They're the ones that built out that and are working on it. So they're they're like one team that's very focused on content for me, but that's very much non-text all video, right? Like even all those links I'm finding those links. They're not finding them.

132:49 Um, but they're building the systems and helping me view a bunch of them and that's just an experiment we we all wanted to run. Um, I'm trying to think if there's anything else useful there. I I I think it's so easy to create content these days. Like like my I'll give you another example. A very good friend of mine, um, he's more challenged with writing, but when he speaks, it's awesome. So I helped him create processes. Sometimes I'll do it for him where I'll take a transcript of his and turn it into really good content. Cuz he's really good at speaking. Like like when he speaks, you totally get what he's saying. If he tries to write it, it's just not the way his brain works. So he struggles. So then I'm like, "Hey." And I told him this like a year and a half ago or something.

133:32 "Just give me your transcript. You're brilliant. Just give me your transcript. That's awesome and I'll help you turn it into content." And it was super easy. Like his transcript was that good. Like they're some of the best like ways I can take that and get it on brand in one shot or two off just his transcript. But that's because his voice is in there. He speaks very eloquently and properly about the things he's talking about. I also told him, "Hey, say it like this." Or give him a little bit of a prompt back in the day of like how to speak in there. But once we figured that out, we were able to do that. So to me it's more like with AI, number one, and number two like with AI and the ability to have AI be multimodal with all these things, there's so much more open to how people can express themselves.

134:16 Can you give me one concrete idea for how you take one inside or an idea and turn it into multiple pieces of content? Like basically digesting one idea into say five tweets. Yeah, I think one way to think about that if you really want to push it really far is if you This is why I mean like I use it more as a researcher and editor. I'm not really trying to use it as a writer per se. But you could use it as an idea generator.

134:42 >> Yeah, you could use it as a writer too. I'm not saying it's like out of scope. I'd rather use it as a writer for my product marketing and the marketing pages. But voice and things like that are still a struggle. Although I found a lot of ways to get it good enough all right. But basically like if you Okay, how about this? You give me an idea. And I'll tell you how to walk through it.

135:09 Okay, very simple idea that I think can be turned into a lot of pieces of content, but I'm always like oh content should always be original. Take action, action precedes clarity. How would you turn it into a lot of different pieces of content? >> Sure, yeah, that's great. Um So I think what I would do is the first thing I would do on something like that is actually like tell and this is if I'm playing around with idea. So this is like more of an exploration exercise to find topics.

135:42 But I don't think you can write something without knowing who you're writing for. So first of all, that's that's why it's just an idea. The topic includes a bundle of who you're writing for and what it should say and whatever, in my opinion. So I would put that in ChatGPT and be like I would I would love to get different perspectives on this statement. And then usually when do just something like that, it'll get so much gold in what it gives me back.

136:13 Cuz it'll say, "Well, if you're this type of person, or this type of person, it would think like this, think like that, all that, this and that." And so, from there, usually whatever response it gives me, I get inspired by that. And then I find where I want to go dig deeper and kind of expand and broaden the topics. Another one that I find really powerful in this context, it would probably work, is the prompt is literally "Write me a deep research Write me a comprehensive deep research prompt to dig into this." And I'll give it more context. Because I'm really debating whether this will resonate or that will resonate or this will. Then it'll give me the prompt, then I'll go run the prompt.

136:51 And I'll go bring the research back to that chat, cuz I'll do it in separate chats. I'll be like, "Okay, this is what I got back. How should I think about this?" Or how should we think about it? Or how What What are the pros and cons and all that? So, I'm more using it as that thinking partner that I that you essentially never had to help you help you essentially deconstruct, reconstruct, repurpose an idea. Well, I feel like the idea that I gave you is very simplistic. What would be an idea that you would create multiple pieces of content from? Just give me an example of an idea.

137:21 >> I I actually thought it was good. If you're going for that kind of content. >> motivational content? >> Yeah, yeah, absolutely. I think it was good cuz And you might even find more practical stuff right from there as you start sort of digging in, right? But, a more practical one The one of my my favorite one, actually, and I think everyone should be doing this, and is basically like like tell a story. So, I'd rather start with a story.

137:50 And a story that's real for me. We talked about many stories today. So, if I Let's say I want to write about entrepreneurship. Well, I probably need to find a good hook. A great hook for me is when I was 4 years old. Got that hook. >> Yeah, yeah. So, I'd probably go to try to be like, "I really want to write about this. Here's a voice memo of me talking about that story. Help me turn it into something useful or some content for other founders who are going to sort of learn this lesson that I have in mind about this.

138:25 Which is like the earlier you start the better. I started at 4 years ago. But, I just made that up. But, it can help me find all those hooks and all those things. And so, I'll just work with it as a editor to help me like edit down, edit up, do the research, bring it back, and then figure out how I should say it. I also have an advantage that like I have a ton of content and writing out there that like I can You could write for >> have a results of that, I can get things that are closer to my voice with less edits. But, it's still very hard to get AI to write in someone's voice. It's not impossible.

139:00 I've gotten very close to it. But, if you don't edit it, you're going to find things that don't sound like you. But, maybe but a lot of people don't know what they sound like. So, that's a little bit of a or don't know how to sound like what >> Figure that out first. To wrap up, I wanted to ask you some short questions. What is your life philosophy in one sentence? It was all a dream. I have to ask a follow-up about this.

139:24 Can you elaborate? >> [laughter] >> We're having an experience right now. Mhm. However, you remember it and I remember it is going to be different. Right? After it's done, we can't go back. Did it exist? Or was it a dream? Your dream, my dream, separate dreams. But, we're still here together. But, the experience we had is very different. Yeah, there's commonalities.

139:55 But, your our memories of it are like a dream. Some of them we remember, some of them we don't, some of them are nightmares. So, yeah, I I the philosophy is it was all a dream. So just to interpret it, my interpretation of this philosophy is that everyone lives in their own head and you can control your reality because everyone's perception of the reality is different. That's definitely a part of it. Another part of it for me is the idea that if we put a lot of weight on everything we experience, but if we think of it as a dream, we're going to put less weight on it after the dream and probably put the appropriate weight like in the moment and all that while we're there and have the presence.

140:44 So one word, presence. The sentence, it was all a dream cuz I think that's how you get to presence as weird as that sounds. I love it. Um what is one trait that you have that you're really grateful for? Yeah, I I I I don't know where I I I I I I started going into a few options and started getting into how did I get those traits, but that's not the question you asked. So the simple trait I'll say is uh the one I probably value almost more than any other trait is empathy.

141:14 Oh, interesting. I thought you would say curiosity. Hm? Okay. One might lead to the other depending on how you think about it in certain aspects. What advice do you give the most? There's a statement that I said to my co-founder but before that I said it to the person who introduced us. Has nothing to do with that relationship or anything. And so this is probably the one I would say that I I I don't exactly I'm not able to say it to most people exactly like this, but underneath if anyone's gotten an advice for me they're going to understand this, underneath it is essentially the statement, which is the only way to do more is do more.

142:00 Take that however way you want. It's super philosophical. It It can be unpacked in many different ways. And I'm not saying do more. That's the only thing. The only way to do more is to do more, but I'm not saying do more. That That That is the most confusing thing you can imagine, but it is true. The only way to do more, if you want to do more, is to do more. But I'm not advocating that you do more.

142:23 I'm just saying if that's true Yeah. Yeah. Yeah. What are you doing? Yeah. Right? And then you start thinking about that from me being a founder, most successful founders out there. I don't know a founder who's not doing more to do more. Like Like Like Yeah. Yeah. Yeah. Why does Elon have so many companies? Why does Google have so many products? Uh the only thing that I'm that this makes me think of is that you need to really understand yourself to see what the what is the outcome that you want.

142:53 And if the outcome is you that you want is to have a ton of things, then the only answer is to do more, but perhaps that's not the outcome that you want. And then there is a different path. Yeah, but you went to things. You're more with things. They don't have to be things. Or just like life that you want to live. >> More execution, more ideas. Like Like let's put it this way. In today's world, I think this is more real than ever.

143:19 I think the only way to grow is to have more shots on goal. And the only way to have more shots on goal is that philosophy. Is to do more things. Yeah. Whatever way you want to look at it. Yeah. And what are you excited about in the next 10 years? Although I realize next 10 years is very uncertain, what are you excited about in the next year? Or 5 years? I I think I'm The word that comes to mind is opportunity. And I think like like part of this is just looking back and saying like cuz I I I I I probably think a lot more than I should.

143:57 So, looking back, it's like where was where were the things where I I felt like I could have done more. And the word opportunity is what comes up. It's like if there's an opportunity in front of me being able to capitalize on it or leverage it or use it or even softer things. We're at a place right now where there's a abundance of opportunity. I think there always is. But right now there's a abundance of opportunity because of a uncertainty around how fast and exactly how things are going to change.

144:36 Which is some of the most fun times you can possibly have. As long as you're not sitting there worrying about everything that you don't control. So, those are all the caveat. Then, thank you so much for your time. This was an awesome conversation as always. Thank you.