In this episode
Today I'm talking to Hiten Shah, serial entrepreneur and co-founder of Crazy Egg, KISSmetrics, and Nira — which he sold to Dropbox. Hiten has been building SaaS companies for over 20 years and has quietly become one of the sharpest operators and thinkers in tech. We go deep on metacognition, self-improvement, and what it actually takes to understand yourself well enough to build great companies and great relationships. Hiten opens up about his process for "poking at the world" to test his own thinking, how he uses Enneagram and Human Design with AI to unlock blind spots, and the mental models that have shaped how he works with co-founders, teams, and his own family.
- His "purple bruise" approach to giving advice — and how he trained himself to go from six-month-delayed feedback to next-day impact
- The Batman and Robin framework for co-founder relationships, partnerships, and even marriage
- Why building faster with AI doesn't mean learning faster — and the companies that have figured out the difference
- "Trust takes ten years" — the advice from a relative in India that keeps proving itself right
- His life philosophy: "It was all a dream" — and what that has to do with presence
Chapters
- Intro
- Start Your Year in October
- The Purple Bruise Method
- AI as a Thinking Partner
- Thinking About Your Thinking
- Find Your Triggers First
- Decide Fast With Less
- Entrepreneur Since Age Four
- Shed Judgment, Stay Curious
- When Strengths Become Sabotage
- Batman and Robin Partnerships
- Finding the Right Co-Founder
- Trust Takes Ten Years
- Fast Success Hides Lessons
- Build Faster ≠ Learn Faster
- The Lost Craft of Startups
- Follow Energy, Not Goals
- The Crisis Nobody Sees
- Selling at Peak Value
- Know Yourself Through AI
- One Idea, Many Posts
- "It Was All a Dream"
About the guest
Full transcript
LubaI'm so excited to have you here. Thank you so much for taking the time.
HitenYeah. For sure.
LubaOkay. 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. So it's really impressive. And I think ten years ago I wanted to be someone like you. You know, someone who runs multiple companies, produces a lot of content, does a podcast, blog. I'm still figuring out how to get there.
HitenSo yeah, I think you're getting like...
LubaSlow, very, very slow stuff. So let's start with something that you just mentioned to me before this conversation. 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?
HitenYeah. You know, I think the thing we were talking about was, you know, time is artificial, and we kind of make it up as society and have made it up. So as much as I believe that, like, I want to evolve, improve, iterate myself all the time, there are specific, like, time sort of milestones that I try to figure out how to leverage to make change happen. And I think that that's the broader way I think about it.
And what I've found for myself over the last, let's say, five, six, seven years is by the time Halloween hits, I want to have enough clarity about what I want to change for the next year. So, like, meaning, like, oh, there's these areas that I feel like we should improve, or I wanted to get to X, Y or Z this year and I haven't. There are a few of those areas actually last year where I just didn't get to it. And so then what I do is between Halloween and basically, like, New Year, I'm sort of... The best way to describe it would be, like, poking at the world and then seeing what pokes 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? Am I, like, feeling good about how I'm thinking about it?
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 actually helps me think. Because especially these days, when there's just so much information and things you can dive into, 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.
LubaTotally.
HitenLike, yeah, revenue goals, hiring goals, whatever those goals are. 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 certain things. And, like, I've learned to take advantage of that.
LubaYeah, 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, not as much information will come in, and you have just more time personally to reflect because you're not overflooded with externality, is really helpful. So a couple of things to dive into. When you say you poke at things and see what pokes back, give me the details. What does your process actually look like? So you're on a journey of self-improvement and bettering yourself. What does that inheritance operating system actually mean?
HitenYeah. So, like, I love that you asked it the way you did, because I tend to really want to give, and also get, get is harder, but give very contextual advice. So this idea of poking is amazing. It might be a you thing, it might be a someone-else thing. But based on your personality and how you 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, because I think that'll help. Like, if I'm speaking to someone, I am subconsciously, almost automatically, testing what resonates with them and what doesn't.
LubaIt's almost like you're running the experiment of testing out a conversation with them in the background.
HitenYeah, 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 disgusted reaction, or the opposite? Or what do I get? And so, let's put it this way, I think these types of things are not even superpowers. They're, like, natural abilities we gravitate towards. And oftentimes we don't know.
So once, when I didn't know, 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 everyone at that time, their own time to figure out what to do with what I said. 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 had. But I would hit some root there that, like, almost like 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, like, an accident there, a 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. So what would happen is someone would come back to me six months later and be like, hey, that thing you said to me six months ago, I get it now.
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. And that's what got me to subconsciously, without thinking about it, be able to improve in the moment with a person in 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 six months to literally, I'm getting a text the next day, and the person's like, hey, thank you for that, that was really helpful, 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 it. It wasn't like I was holding anything back. It was more like I was priming them to be open to what I say without the reaction I used to get. Because the reaction I used to get was clearly not providing them with enough value fast enough, in my opinion. Maybe in their opinion it was, but it wasn't.
LubaI'm going to, just for anyone listening, dive into the whole topic of personalities and how you became a student of yourself and people around you, because 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 an 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?
HitenYeah.
LubaLike, 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.
HitenMost of the time the process is very much, like, 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. So that's usually the first low-hanging fruit. 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, what do I not like? And usually that starts with: what is the current state? And without making it a goal, 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. The vast majority of the time, it's how I'm thinking about it. That's, like, probably 90, 95% of the problem.
LubaAnd are you writing things down? Are you talking to AI?
HitenSo I take a lot of notes. AI showed up for this process this year. I have, you know, getting into some of the personality stuff, I will make a project. I've made a project, I've put all my personality stuff in it, and I can chat with it, whether it's my Enneagram or my Human Design or whatever I'm into at the time. I'm into these things. But I'll tell you, 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, because that's more scientific in your mind. I don't think it is. But other people, the Big Five.
LubaYeah.
HitenSo 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 from that, that I built out last year at some point.
LubaWhich AI are you using?
HitenI actually built it in Claude first. And I used to use Claude a lot, and then I moved over to ChatGPT. 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 the work that I try to do around myself.
LubaI saw this tweet the other day that ChatGPT is like your personal coach, 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 what.
HitenYeah, you know, I don't think Claude writes great content compared to ChatGPT, and I know a lot of people do.
LubaYeah, that's a hot take.
HitenAnd my argument is that Claude is good at writing code, not content, and it always will be, because 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, 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 ChatGPT has this problem sometimes. But if I upload a CSV or Excel file, it's trying to run code. Guess what? If I copy the cells and paste them in the blank chat, it's not going to run code, but it 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 run out of tokens, the errors are bad, and it gets unusable really fast. And I found myself switching over to ChatGPT 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, because 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, because whatever I was doing with Claude, I can get ChatGPT to do it as good, if not better. It might take a little more work in some areas, fine, but that's how both of them are. Some stuff is easier in ChatGPT, some stuff easier in Claude, and some stuff completely easier in Gemini. I would actually say Claude 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.
LubaOkay, 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?
HitenI wouldn't use it most of the time. What I'll do is, the poking 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'm going to be like, oh, like, those notes might be like, oh, crap, I used this word and they didn't seem to understand it.
LubaAnd so every single meeting you have, you take notes afterwards?
HitenI used to, yeah.
LubaOh, you used to. What happened?
HitenI hit the goal I wanted, the goal of getting that six-month thing. 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. And you didn't come back to me six months later and be like, you were right. What was happening a lot is you come back six months later and, you were right. Like, if I was right and it took you six months to come back to me, I actually was wrong. I didn't actually help you enough, right?
So the point there is, like, there is an 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. Because bad ways would be like... if you notice, like, when I talk to you, I rarely will ask you a question.
LubaThat's true, actually. Right. Yeah. Why? I guess you want to... That's a good question. You want to hear what comes up naturally, without you leading me in a specific direction.
HitenIf I ask you a question, that means I have an agenda. I try to make the vast majority of my meetings with no agenda. 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 the 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 someone I met a while ago, I work with them, they had never been in a meeting with me, like a work meeting. I work with them, but we'd never been in a meeting. We got in a meeting, and it was just one of those meetings where I was doing a lot of that refocusing.
LubaRefocusing with questions, right? Or how do you... what do you question?
HitenYeah. Questions are usually the best, because you ask a question, everyone starts... And if you ask the right question, you know the game, right?
LubaYeah.
HitenSo yeah. Exactly. And 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 messages me. She's like, oh, so that's Hiten in the meeting. I'm like, no, that's Hiten in the meeting that matters. That really matters. Where if we 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 think, like, the muscle for me is actually being able to identify... This is the system, and the core thing that relates to a lot of the things we've talked about, which 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 the thing I've just learned is, like, the world is quieter. That's it. Which helps me think. Because 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 because of meetings or just the energy out there.
LubaWhat is the most effective way for you to think? Is it writing, or is it something else?
HitenI actually haven't found any better way than talking it out. Oh, and self-talk.
LubaWell, what do you mean? Like rubber-ducking?
HitenSort 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.
LubaThat's true.
HitenIt can be talking to ChatGPT about it, or it can be self-talk. But at the end of the day, I think most of what I do is what people would call metacognition, where you're thinking about thinking. Why'd you say this? Why do you say this? Why do you do this?
Now, I was talking to someone who's very good at poker, and he's like, oh, there's this thing in poker. I forgot what it's called. My uncle had me read *Liar's Poker* back in the day. But the person said, there's this thing in poker, and I'm like, what is it? And he's like, well, it's the thing that I see you doing. Do you know you're doing it? And 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, 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 deeper you can go around that, and that way of understanding something, or trying to, is basically some poker strategy.
Again, I probably butchered it, but what I latched on to 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, because 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.
LubaSo 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 trying to reverse-engineer why you're having this thought?
HitenYeah.
LubaHow long can you go through these loops?
HitenAs long as you want. It can drive you crazy, too. 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, we don't even know why we're here. Like, there's no answer. So this is one of those things where it is existential, and you can think about that all day.
But in a specific area, like what I mentioned, if I want to improve my thinking about someone else's problems or businesses, in this case, I did that loop. Okay, I'm talking to them about it. I'm giving them feedback. I go take some notes to just make sure I essentially codify the learnings. I never looked at the notes again, ever. Because usually if there's follow-ups, I'll do them. I have a good memory for those. Those are easy. The harder parts are, like: I said this thing, it didn't resonate. I said this thing, it resonated. I should have said it 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.
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, because I'm leading the witness somewhere, and 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, 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 ask you a few questions to dig in. But we started with something you cared about, and I could go from there. But the amount of questions I'm going to ask, versus someone who is as curious as me, is probably a 10x difference. Because my curiosity, I don't need it answered by you answering my question. I can get it answered by just hearing you talk.
LubaSo then for someone listening and trying to be like, okay, I want to be much more self-reflective, and I want to understand how to set goals, 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?
HitenI 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. 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 a feeling that you did not have prior. It could be negative or positive. We all have them.
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 an easy tactic. Because it's likely you're going to find negative triggers first and go for those, because we all are probably going to go there. But if something's legit triggering you and you don't want it to, or even if you want it to, but you want to improve yourself, you probably should look at what's going on there. So that's the easy one. It's like, why'd you get mad? So the simple thing is, why'd I get mad when they said that? Why'd I get mad? And you can ask that for yourself, you know.
And again, like, there's a lot of theories and psychology around all of this stuff. But at 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, and where the rooms are, and all this stuff. Like, I used to have this thing where my CTO and I, 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. It's got the duct tape, okay? Or if that box is over there, cool. And what that means is there's a box. I don't have to go open the box, 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. Because there are things that we have in our minds that we cannot go look at, but we can probably label them and say, that's a box. So then you know it exists. Otherwise we're not acknowledging it. So whether it's that analogy or whatever the heck works for you, the house or whatever, 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 with.
LubaYeah, I love this whole topic of the 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. 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?
HitenI think I was always like this somehow. And it was honestly just curiosity more than anything else. And 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 I've met don't feel comfortable with that. They can't ask why if they're not going to get an answer.
Another way I think about this, again, knowing yourself, is... When I was working 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. Like, okay, this person worked at, like, Apple, and worked at Dropbox, where I was at the time. And, like, 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: 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 ten. Give me ten, I'll make a decision. Or I'll make a decision that we cannot make a decision, and here's exactly why and what we should go find out. But usually, even with 10%, I can go make a decision.
And so she was saying decisive. What I'm saying is, actually, it's 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.
LubaYeah. 10% of information is... 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 about your thinking, then you kind of fall into the category of overthinkers. And then you can be, like, overthinking that.
HitenIf you've thought enough, though, you can reduce the amount of information you need going forward.
LubaBecause you've had enough experience to see how the...
HitenBut the thinking is the experience, in that case.
LubaThat's very meta, right?
HitenLike, if you think about thinking, you're experiencing something. Well, we normally think of, I experienced that thing. I did that marketing, I did that product thing, or did that sales thing, and that's experience. But, like, if you can just think about a problem, that's actually experience too. So if you're experiencing all these things 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.
LubaThe 10%, did you reach 10% over time, or has that always been the case?
HitenI think that's always been the case. And I think most of it...
LubaDo you think it comes from childhood, or your parents?
HitenI think it just comes from... 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, I'm going to get into another concept, but where freedom of thought is actually incentivized. And so I think that freedom of time, usually you get freedom of time because you don't need to make money for a living. That's the typical way. Or you get time after whatever you're doing to make money. But freedom of thought is actually more 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 many years later that was how you find things. But my parents were physicians, my dad and my mom too. But, 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. 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 by my father that if you have a problem, I need to be your first call. I never really did that, although I should have, because I caused a lot of trouble growing up. 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 weren't theirs are still running in their system.
A lot of what I said, the triggers 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 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 them, right? Because you're essentially removing an attachment to some kind of story or some kind of thing that you kind of got in your head.
LubaWow, so many things to dive into. Just to set the agenda, the 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 tests, personality frameworks. 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 do you feel like you're cultivating the same environment for your kids right now?
HitenYeah. 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...
LubaCan you explain what that is? I actually don't understand what that means.
HitenOh yeah. Yeah, yeah. So most of the time, most kids were told, hey, you have to be home by 9 p.m., okay? This was a time when we didn't have phones, and we actually cared about getting a car when we were 16. So, fortunate enough, got a car. But I didn't have a curfew, because my dad didn't value the fact that I was home at a certain time. He valued the fact that I was okay, over thinking that being home at a certain time meant I was...
LubaOver, like, controlling you and your decisions.
HitenSo he gave me the trust to make good and bad decisions around these types of things. So that was much later. I think younger, when I was four years old, my dad told me I should be an entrepreneur. Then, as I grew up...
LubaWhen you were four years old?
HitenDamn. That's when he started. 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...
LubaDo you think he was trying to fulfill his own dream?
HitenOh, sure. Well, sure he was. But he's also very entrepreneurial. But I'm sure there was some aspect of that. I have a standing conversation I tried to have with him once. He just wasn't able to, because he was in India and we were on a call. 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, but he's like, I've 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 that'll get to kind of some of the answers for some of the questions you had.
So he told me that when I was four. And as I grew up, he told me, get married early and have kids early. And that was probably 10, 12, 13. So I started dating my wife when we were 15. I had kids...
LubaIt's interesting that you were so susceptible to what your dad was saying, because, you know, for a lot of people, they'd be like, oh, my parents said this, and I completely rejected it.
HitenI think the age that he started that at was...
LubaProbably young enough for you.
HitenIt was, like, four years old, where you're like, I don't even know what that means. Yeah. But thank you, I don't know. Yeah, yeah. And so I think 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's in it because he's like, look, if this is what you want, here's what I recommend, kind of thing. But he didn't have, like, all these rules. He just had these things, like, hey, I like this for you. He used to do this. You should do these other things.
So now when I talk to him about this, I told him this many years ago, I was like, I'm not going to listen to you anymore. I did all those things. The kids are not going to listen. You know? They're gonna listen to you around here. Are you? Ginger thing? So, you know, there's no resentment, but, like, I don't know, the alternative is definitely the truth.
LubaSo I assume you're not doing that to your kids, where you're, like, four years old: "I have an entrepreneur."
HitenI haven't told them those things, because I think we live in a different world, where those things are accessible and much easier, and don't need the kind of prodding or pushing. But kids-wise, like, my daughter's 11, my son's 15. I think the environment they were raised in was very much... My wife's a founder, I'm a founder, her brother's a founder, one of their cousins is a founder. I don't have any siblings.
LubaSounds like they might be founders.
HitenLike, if they want to, right? 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 the behavior of the parents than it is, like, the...
LubaThe, like, specific things you prescribe them.
HitenExactly. 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 historical, whatever the opposite of baggage is, in my life. So a lot of the crap that a lot of people might be dealing with later, I've already dealt with, because we've been dating since we were 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, 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 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, because even some parents don't argue in front of everyone else and all that stuff.
But growing up, I had these rules, 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 just sounds like there were things that he felt were important for the day and age that I was living in versus him, and some of them were things he wished he would have done, too. Don't get me wrong, he got married early. He had a kid early enough. 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, you know, while he was working too. So he's very entrepreneurial. I think he is an entrepreneur, and he would say that too, probably. But he didn't get to be a businessman. I think that's really what he wanted me to be. And he got his wish.
LubaLet's come back to curiosity. So because of your dad's role modeling and your mom's role modeling of researching, you had this 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? Because 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 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?
HitenI think usually people would probably come at it from, like, I'm not creative, or I'm blocked, or something like that. And 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.
LubaYeah. One thing that 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, or 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 the past. 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.
HitenThat's why it's not childish curiosity. It's childlike curiosity, right? Because childish generally means childish, but childlike basically means: can you look at something as if you've never looked at it before, but you've looked at it a billion times? 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?
LubaSo how do you shed judgment? It's easier said than done. If someone is super judgmental, like, what do they do?
HitenI think you have to figure out... I actually think it starts with understanding where your assumptions are coming from. So this goes into, like, work. Like, 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?
And I try to do that to myself. So if I look at something, I'm like, oh, it works like that, works like that, or does this. Or even looking at that 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? Because if I can do that, then 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...
LubaAnd figure out how it works for you?
HitenYeah. And the basic building blocks, right? And I think, like, that is the type of exercise. And that's, like, very hard to do, because I look at it and I still think fireplace. I don't look at it and 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.
LubaI want to bring your understanding, your curiosity about yourself and how you work, to the famous incident that you had with Hiten 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 refocusing them. How come you didn't realize that earlier, given your interest in self-understanding?
HitenYeah. So I think that the environment you put yourself in, and the assumptions you make about that environment, will lead to some of those things that I was experiencing, where I would...
LubaAnd can you paint some more color? Like, what exactly was happening? How did you realize?
HitenSo at that time, it was my first venture-backed startup. And I had assumptions about what was important. And so what I thought was important was that we were nimble, and moving fast, and trying things constantly. 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 that are paying and all that, I didn't change. 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, still in the past. Back to the old point 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 happens 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 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, because there's an advantage they're going to have at those, if they can figure out what those advantages are. Because instead of experimenting on getting to product-market fit, we should have been experimenting on growth a lot more. I just confused those two things.
LubaYeah, I feel like the vibe of what you just said is very *The Courage to Be Disliked*, which I saw was a book that you found pretty impactful. I generally always believed 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 *The Courage to Be Disliked*, or was that, like, a very impactful read that made you change?
HitenThis is actually the weirdest thing about metacognition, or some of the stuff we've talked about. If I've thought enough about something over time, so, these little processes, then when I read something like that, it's 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, giving names to things that I couldn't quite understand. Because my great relationships mapped to very clear delineation of their task and my task, which is a big part of the book.
LubaYeah. To give a bit of a summary on the book, one of the things is, as you said, what is your task and what is their task. It kind of also reminds me of, do you know Mel Robbins, the podcast host? She has the Let Them Theory. And the Let Them Theory is kind of the same thing, where you just let other people react to things the way they want, and it is not your responsibility to impact their reaction in any way. Your responsibility is to do your thing, be yourself, and just see how the world reacts, and adjust your part of the job if you don't like the reaction. But you're not going to impact how other people, or the other person, is going to react. What are they going to say? Are they going to like you? Are they going to dislike you? So that's just a complete waste of your energy and time.
HitenYep, yep. And so when that clicks for you, you realize that you should be focused on your tasks. And the whole theory is that the reason we have relationship dysfunction is because 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 Batman and Robin. So the example I like to give is, we bought a house and we were remodeling. It took a couple of years. My wife and I. And she stepped in the house 700 times. I stepped in the house 20 times over two years. Guess who was Batman? Which basically means, like, the analogy plays out. I've taught 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've got to Batman-and-Robin as many things as you can. It's not like... Someone told me, oh, so they're always Batman. I'm like, no, no, no. Depending on the task...
LubaTask.
Hiten...or the job, or the thing, someone's Batman, someone's Robin. Because if there's two Batmans, nothing's going to get done, because they're both going to try to do the wrong things, because 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 is 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.
LubaI feel like that's also a common argument with childcare. I was just talking to your 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 he's not managing the au pair also. So, okay, so how do you...
HitenManage two people managing the au pair? It's 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 being Robin. 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.
LubaWith the au pair.
HitenAnd this is what I found in those situations, where he's supposed to be Batman but he's not being Batman. That's usually what that boils down to. So many relationships I've helped at least understand what's going on with the framework.
LubaOkay, so then let's say you understand the framework. I think this is a really good segue into co-founder relationships. So your first co-founder was your brother...
HitenYeah, brother-in-law.
LubaAnd you guys started a company around, like, 15, or you were both 16?
HitenHe was 11, I was 15, when we met. I graduated college, and he was graduating high school.
LubaWow.
HitenAnd that's when we started the company.
LubaAnd then 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?
HitenBatman and Robin. 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.
LubaSo give me more specifics. How do you get clear? 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...
HitenSo I'll talk about two different things. The first thing I'll talk about is how to find a co-founder, because I think that kind of is where you were going, right? Then I'll talk about how to work with the co-founder, because I think those are two separate things.
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 just going to start there, because we don't need to talk about how to get there, because 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 while. That is fine. 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 all it is... I'll tell you also the most common one that comes up as an issue. 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.
LubaOh my God, that's such a common thing lately.
HitenLet me tell you how that comes up, though, and how I try to get them to pull it up earlier. Both people, independently, right?
LubaIt's probably like an article or something.
HitenThey 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 could 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, which is, again, absurdly common. And that's usually a nonstarter. Once that shows up, like, you're done. You're usually done. Because 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, the other person is focused on that.
So, you know, it's funny. Like, I also break the rules a lot, but, like, someone joined a new project. So I also have a side note. To me, these initiatives, like these startups or businesses, are actually project, product, business. And you're just going through those stages. Yeah, product-market fit, 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 the team, I was like, hey, you know, I said this: if you have a question or any of that, you can ask both of us. But, like, whatever she says, like, it might as well be, how you folks have been treating me, as if I said it, right? And I just called it that. And the reason for that is, in that project, or in that product now, or that business, 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, because she knows when to come back to me or whatever.
But this is a person... And this is another side note. 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, just because 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 get to work with her. So, but I was very explicit. But in my mind, and again, the reason I say that might be the opposite of the Batman or Robin thing is, like, they could go to either of us, but what they might not know is that she's Batman in my head. 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... How can I put it? We don't have any work to do to understand each other, or context. Zero.
LubaSo 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. And then if it's a no-go, if it's a co-CEO situation, or someone wants to build a small business and the other person wants to scale up a company... Are there any other red flags?
HitenThose are the big ones. You're just trying to find where you disagree and trying to work through the disagreements. The CEO thing is rarely a disagreement that can be worked through. What the goal of this business 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 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 an expert at that. Things like that.
But people don't tease any of this out. And instead they do the work trials and build the product, and then they realize it's crap later, when they've got to figure out their titles or something else, and they're like, wait, 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: we spent ten years, more than ten years, half hour every week. We tried to make the meeting at least 30 to 50 times a year.
LubaThat was just, like, friends meeting? You guys were talking about work, talking about whatever?
HitenI helped her out. She helped me out. Whatever.
LubaAnd then obviously, then it's an assumption of really deep trust, and actually understanding someone. Let's talk about that. How do you build up trust with someone? And how do you get to know someone really well to, I guess, deepen that trust?
HitenIt's funny, this is a good one. And I'll give you one funny or interesting story. I have relatives in India, like a cousin, uncle, like, uncle relative, blood relative. He's my great-uncle's kid, that's why I say it. So my dad's cousin, actually. And they're extremely successful business people. Like, extremely successful.
LubaRuns in the family.
HitenMaybe way more successful than I, in that context. And I asked him when I was, like, 15, hey, what do I need to know? Trust takes ten years. I was like, crap. But every part of me didn't want to agree or believe that. But every time I think through that, it just keeps coming back to what he said, which is, like, it takes ten years. So if I know it's going to take ten years, I'm really just trying to figure out who is worthy of that investment. And I don't mean, like, me, like, both sides, right? So which relationships are worthy of that investment?
So, for example, an engineer I work with, I hired. We hired him in, like, 2010 or 2011 at KISSmetrics, my first venture-backed company. 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. That relationship is now 12, 13, 15 years, easy. 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, because he knows databases, blah, blah, blah. I used to work with him. And then I met him. And he came on as an analytics engineer. He ended up being the head of product and engineering at KISSmetrics, and he was our CTO. He came on a little bit later, but he was working on one of my other projects at that time.
I trust him. It felt like it didn't take ten, but it probably took ten. And I think part of that is, like, you find people's patterns, and you find all that through longevity. Like, 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, we aligned with, and we got along. And those two things are what hacked that process of trust. But it was a constant trust...
LubaExercise.
HitenExercise. While with Steve, the CTO guy, there's no exercise. Like, there's even a few patterns we figured out that we're going to change if and when we work together again. There were two times that happened, and those were so critical that now we both are watching for it. And it was just something in our thinking. It had nothing to do with the relationship. It was just more like, if we thought differently those two times, those things we were working on 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 kinds of things, which you can't do without having enough shots on goal. 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 something works quickly, the amount of effort I put into figuring 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 because if it works quickly and I don't know why it worked, one, I can't repeat it. Two, I don't understand it. 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 there 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 good. Life is good, that's luck. But then you've 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. Because 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.
LubaYeah, I agree. I feel like being really fast at making things work is 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 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, so-and-so was really hard, so I had to apply a lot of grit and work ethic to really figure it out. And as someone who's always been, like, good at getting 80% somewhere, I've been good at most things 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 where 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 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. And you feel like you didn't really actually put the work in.
HitenYeah. 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 repeating success. Because at the end of the day, once you're successful, you want to repeat it. 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 where you have to rebuild the muscle. Yeah, you can't 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, because it happened quickly.
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 are amounts of dysfunction that would not work if the thing wasn't working and didn't have product-market fit so quickly.
LubaYeah, because growth...
HitenYeah, like. And most of the time, like, you dig in, I'm like, wait, is there excellence anywhere, from a proper standard?
LubaOr did they just get lucky on the market...
HitenIf 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? 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's their bread and butter. That's what I call it.
LubaOkay. I want to come back to co-founders. So obviously a lot of it is people and people's alignment. I feel like now, though, for anyone who's looking for, say, a tech co-founder, it's harder. And I want to hear whether that's...
HitenYou mean, like, someone like you that's technical and vibe codes, or like...
LubaNo, just, like, harder to find someone who's down to start a business, just because there are 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? Do you think it's harder to find a co-founder than, say, ten, 15 years ago? Because then it was a risky bet, and now it's, I mean, it's still a risky bet, but there are a lot of other bets you can take with your career. Because 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 to people who are in that spot?
HitenI 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, right? Like, I don't actually think you need a co-founder. And now the world of tech has invented a founding member.
LubaRight, right.
HitenSo 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 the bar for what that person can do with you is much lower. Because usually a co-founder means, like, in the best sense, a lot of what you can do, they can do, in areas that are not 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, and neither of us writes code. And 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 towards 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 a contract. That was before AI, but even with AI, she'll still read every word, even using AI. 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 puzzle pieces to have a clear picture of what the scene looks like and what you're going to achieve? And I think a lot of people don't enter these relationships, and start these businesses, with enough consciousness of, not who, but what do we need to win? 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 you start taking 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 or not, but you're not picking someone, or finding people, who would co-found with you. 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.
LubaLet's talk about winning in 2026. Have a lot of things changed in your own mind for how startup founders should approach winning now, with, you know, the boom of AI, the tools, etc.? Are the fundamentals still true, or have they changed a lot?
HitenYeah. You know, I'll give you three different perspectives. So the first perspective is my classic one on this. So back in the day, I learned Lean Startup from Eric Ries and Sean Ellis. I'm adding Sean Ellis because I think a lot of the principles that he shared around how you learn faster in that loop... Because the loop is, like, build, measure, learn, and you're going through that loop as fast as you can. His learn part was very strong, and more than just tactical or strategic, because he was a marketer coming in and thinking about it. The reason I'm mentioning that is because Eric Ries was, or is, an engineer and founder, and so he was on the build side. 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 changed 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, what's happened with AI? The first thing 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...
LubaThat was my argument.
HitenYeah, but even in Lean Startup, it says build faster, measure faster, learn faster. Like, that's actually the words. Fine. You could build more and you could build faster. I'll take the win there. But just because that's faster does not instantly make measuring faster or learning faster. So I think what we're dealing with is, this has gotten faster and we can do more. These other areas haven't yet. And the smartest people that understand this, that I've seen, have made the learn-faster faster.
LubaYeah. I feel like with AI you can learn faster too, right?
HitenNot to the same extent as coding faster.
LubaWho are the smartest people who have figured it out?
HitenSo the folks at Gamma have, basically... There was one tweet that was based on the podcast that the founder was on, which was Lenny's. 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 in the morning, build it, go do user testing and stuff like that, which is measuring and learning, and get data by the end of the day on a new idea.
LubaSo what did they do to learn faster? They just are in the mindset that we have to learn faster, and they optimize their processes?
HitenThat's because I think they realized this problem, in whatever way they did.
LubaYeah. Now we have a lot that we built, but...
HitenYou got it. So then you have a backlog of learning. But before, you had a backlog of building. You still do. I don't think we code faster. I think we're still at code more, not code faster. But that's okay. Like, it just looks like it's faster. But there's a lot of brittleness, hallucinations, issues with how we do it. I mean, you know, again, not to pick on them, but I like picking on them, I guess, for now: Claude. They launched Claude Cowork. They built it in ten days. It was vibe-coded, I'd call it that, but essentially Claude Code wrote 100% of the code. Guess what? As a user, it shows.
LubaYeah, I saw a couple of articles on what tasks Cowork can actually get done. And there's a lot of errors, or a lot of misunderstanding.
HitenIt shows that AI built the code. Whether that's good or bad for Anthropic is a completely different story. But when I think about it that way...
LubaMarketing products? Yeah.
HitenGuess what? They built faster. They didn't learn faster. You could argue they did: oh, they shipped it. They didn't learn. But in a lot of ways, without shipping it the way they did... It was a 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 almost... I'll stop picking on them, but, like, it almost does them a disservice. It's basically saying 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 you're a product person and you use it, this is why I turned. 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? And Gemini, they're just going to throw features at it, because 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 haven't.
And that leads to my second point. So I think the second point is that the way we think about speed is almost upside down. And it goes back to the loop and all this stuff. But, like, I think it's very impressive that Anthropic shipped Cowork in ten 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 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 one is basicallyjust because we can build faster, it doesn't mean we can learn faster. We need to fix that. 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, because we can ship already. So I think, if you're a product company... 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 is because, of course, Comet existed first. And yeah, it's not like this idea was novel by any of them, because Dia and The Browser Company could be fine. But, like, look at that. And now what? Does browsing even matter? Should ChatGPT have Atlas? Should they have Comet? Like, 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.
Last year was just build fast, because Perplexity 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 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 have 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 puts everyone to the point of trying that. And I think we don't just have to try that, we just have to do it.
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, but it's a mandate. Last month we didn't publicly talk about it. 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. Ironically, it's funnels, and it's the same thing we built at KISSmetrics. And this month we're going to ship something else. If I could help it, I would want to ship that size of 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, because the only way to get attention is to add value. A book does not add value. A post on LinkedIn does not add value, in this way, to a customer or a potential customer. The thing you ship does, because that's demonstrating, if you're doing it well, which I don't think Perplexity and others did: we heard you, 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.
LubaSo just to reiterate, for anyone listening. So point number one, we need to learn faster. Like, sure, we can build faster, but learning is kind of slow, too. So 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?
HitenYeah, the third one is, I think... The third one is more personal to me, and what I would say is the state of startup knowledge. 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 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, this document, and it'll work for you. And somebody, they've seen a few of these from 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 should have the knowledge that this is the right way. But yet they're questioning it. Not even what I sent them, but generally, how do I do this? There's answers everywhere.
LubaWhy do you think that we haven't caught up to the right way to do things, to all the playbooks?
HitenI don't know if it's caught up, or fell behind. Like, meaning, like, I don't know if we need to, like, meaning the solution. I don't think it's catching up, because that's what I felt like we had to do back in the day. I think it's relearning.
LubaWell, why did we lose the knowledge, then?
HitenTech became an industry.
LubaVersus a craft.
HitenYeah, 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. The investors would do it back in the day.
LubaBut 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 are 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 in time?
HitenI think, like, 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 Hiten 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 use is, we can do everything our way. Okay, cool. 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... 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. That felt basic. Well, it's because you made the org flat, and now it's hundreds of people with a flat org with no real key of who reports to whom. There was this concept called Holacracy back in the 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.
LubaIt reminds me of a couple of times I listened to the episodes of *Acquired* that were about older companies, like companies that started 100 years ago. Yeah, exactly. Or, like, Costco. And I was like, damn, they innovated on a lot of this work stuff a long time ago. Because I feel like in the Valley, because it's all about innovation, innovation of work structure, or how we're going to do a seating 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 learnings throughout, like, 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 just caught myself thinking that I didn't know that this had already existed and been proven for years and years, and it's not, like, a Silicon Valley innovation.
HitenHaving worked at a very large company... Very large meaning large, not very large, like 3,000 people. 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. But having not had that experience first, instead having only the experience of trying to build my own, I look at what they're doing there and I have a different perspective. You don't want a 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 leads to the hierarchy and the structure being abused. While you could build the same hierarchical structure and 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 a flat org.
Because at some point, like, here's a problem. Like, everyone wants to make more money. Like, not everyone, but, like, in general, if you're working in tech and you're an employee and you have a role, you want to make more money. The clarity of how you do that...
LubaTo move up the ladder.
Hiten...is really important. I felt like, working in a larger company, too many of my conversations with my colleagues were around these kinds of things, because they lacked clarity, even with all the structure that existed. Or they didn't like the clarity, that's a different story. Or they didn't like how it worked. They could start their own company. It's fine. I did that, right?
So I think, like, when you think about it like this, we throw away things for the wrong reasons. 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. These are things I think about probably more than most founders, simply because, like, it just comes naturally now. But, like, you know, I used to love to say this: I could walk into a company 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?
LubaSo, yeah, you'd be surprised how many people don't have a clear answer. Or especially the why.
HitenOr they say, because my boss said so. Which is fine, but that's a 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 is a better answer. That is the answer I wish more people would have in the world. Because if they have that answer, then we know there's less dysfunction in organizations.
LubaI 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 how the world has changed, how should someone listening decide what to spend their attention on? 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 are so many things happening, how do you decide what to spend your time on, and what advice can you give to listeners?
HitenI think the micro way that I would describe how you discover the answer 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. So the first answer to that question is, like, what gives you energy and what takes it away from you? And also, like, in some cases, what's neutral? There really isn't neutral, because good is neutral. So what gives you energy? What takes it away? Because 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 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? And that's good. But I know that that's why I'm doing this, why I said yes, right?
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 myself out of that room, and I made the engineers talk to the legal and compliance people. Because I realized, one, it 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.
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 with engineering, at least as a PM, because 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. 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 make on their own. That's generally how I like to manage. But that was kind of, like, the situation that I sort of developed.
But that micro 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. For me, it's actually... and passion is probably the wrong word, but I need conviction 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 mean, I 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. 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, most of us, a lot of us, have so much privilege, so to speak, where we can make choices like this, where we can decide to analyze this and make a decision and do more of what gives us energy, 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... you could call it vibes, call it whatever. But the second I start feeling those bad vibes, or I'm losing energy, I'm like, okay, what do I need to change?
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, because it's dictated. Which means the engineer just needs to go implement it and fix it. If there were deeper things, they'd come to me. But this whole system was out of, hey, that doesn't give me energy. And I used to think... or not me, like, my co-founder actually would be 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, which we all do, 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. Even think about, like, a conversation you're having with your partner. 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 and it doesn't give you energy, that's a mismatch. Because a lot of times these conversations give one person energy and not the other, and it's not a fight, but the people don't realize it. And then later on they part ways. But it was usually because of the erosion of that.
LubaYeah, 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, try a bunch of things, 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.
HitenExactly.
LubaWhat about macro?
HitenI think macro, and this is my third thing. We didn't even get into the third thing.
LubaNo, we did get... okay, we partially got it.
HitenFor the... it does relate to the third thing. I think the macro is that...
LubaOh, the third thing was about the startup fundamentals.
HitenOh yeah. There we go. Yeah, yeah. There you go. So this is...
LubaThis is the fourth thing.
HitenIt's 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... I've had a computer since I was eight, and I don't have the why or the answer, but I think we are generally all dealing with an existential crisis, 100%, that nobody understands. So when you ask that question about macro, or when I go macro and I try to break it out into 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. We are uncertain about what's going to change, how it's going to change, and why it's going to change. To 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 in all the data center stuff, that...
LubaIt's almost like investing into dropping off the cliff.
HitenEven 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. Like, yeah, well, that investor probably doesn't understand what I'm saying here, which is it's so existential. Either you invest in that or you're investing in nothing in tech. You're either investing in that or you're investing in nothing. 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.
LubaYeah.
HitenRight? So if that's the case, that we don't know what we don't know, and no one knows... We have investments, like, in the world, in nuclear now, and chips. Like, the president's coming out and saying, no, no, your electric bill won't go up. Like, what? Like, Microsoft's 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, 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. Could you have predicted that three years ago? I don't know anyone who could have. And that's, 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 has been a founder... This is why a lot of the founders are coming back, I think, and doing stuff. Because we are very good at dealing with change. If you've done it once, and you see what you're seeing out there right now, you're like, oh, change, bring it.
LubaYeah.
HitenRight? 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 an engineer, you're a computer scientist. You're a founder, but you're a computer scientist first. What the hell are you doing sitting on the sidelines? What a kick in the ass. Like, I gotta say, right? I mean, I assume it happened, because he said it happened. But, like, man, if these people are starting companies, 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 change is that's happening, and make an impact somewhere. But where that is, or whatever, I think you have to find it in the micro way, 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 Cowork thing, like, a lot of people have already come out and said, oh, there's so many startups that are killed because of that thing. Yeah, but they built it in ten days. If your startup is killed because of something Anthropic could build in ten days, or 5 or 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 because 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.
And that's Anthropic. Like, we used to say that about companies like Google when they shipped something. Oh no, this is Anthropic. Like, they're not that old. Yeah, 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, they could be not scary. But, like, why are we saying that? Oh, social media and Twitter and the amplification of whatever. Okay, fine. They haven't killed anyone. They're not going to kill anyone. 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, or OpenAI, is, Anthropic is, that's only good for us, because that means more people are getting used to how this stuff works.
LubaFor 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?
HitenOkay, so the most cliché 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 good...
LubaAt control, and a lot of things.
HitenAt 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 schemer entrepreneur in all of us. But then I can control that thing. Sure. That's the art of entrepreneurship: 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 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 that is, why are you feeling like that? And then I would get into all the stuff of, like, well, again, just to go there for a second, when was the first time you felt like... And I would just walk through, like, what is it?
LubaWhat was the trigger?
HitenWhat is the story? What is the trigger? Because as much as we believe everything is going to change, I'm sitting on a couch in a place like this...
LubaThat hasn't changed. It's like, where's my flying car? Nothing changed.
HitenAnd it was always... The microphones are better. Cool.
LubaThe cameras are better.
HitenYes, they are amazing. What has changed?
LubaRight. Fundamentals haven't really changed.
HitenWe still 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...
LubaOh, really? Is that happening?
HitenUBI. Oh, what is it?
LubaThe abundance...
HitenUBI, universal...
LubaBasic income.
HitenHey.
LubaSomething that hasn't happened yet.
HitenSomeone 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 that.
LubaRight. 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? There was, or like a side project?
HitenI left Crazy Egg. I'd just started another analytics company called KISSmetrics, so I left back then. Yeah, and I haven't worked on it until literally last year.
LubaBut was it running still?
HitenYeah, my wife was running it.
LubaOkay. Got it.
HitenSo it was running as a self-funded SaaS business for 20 years.
LubaWow.
HitenAnd then basically the main reason we sold the company, and wanted to sell it, is because 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.
LubaYeah, yeah.
HitenAnd it's going to drop. And then you're going to have to find a way to get it back up. And that is every company. And that part is the hardest part. We think this part is the hardest part, but it's when we figure something out and it stops working, or you can just see that. So we were at a peak of value.
LubaThat was KISSmetrics?
HitenNo, this was Nira.
LubaOkay, okay. Wait, so what happened to KISSmetrics?
HitenKISSmetrics? We had a journey. I left that company and didn't want to do anything else. We were one of the first to have, like, privacy class-action lawsuits and stuff.
LubaThat was when you decided to take your reflection break, to figure out what...
HitenMore or less. Yeah. And a CEO took over and stuff like that. I helped replace him as well, and went back in for six months and came back out. And then kind of haven't touched the business since. Other people were running it and doing it. It was venture-backed.
Then I took a few years. And that's when I met my co-founder. And we were actually first building, for lack of a better word, a Glean competitor. So an enterprise search tool. Then we realized that IT and security actually had a bigger problem to solve, pre-AI. And so we started focusing on that. And then that turned into Nira, because we rebranded. And then, yeah, we were just at a peak of 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 an IT or security person, and see all the permissions. And with a couple clicks you can find a million of them, a 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, 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.
LubaBut then, so the company reached peak value. But given you were always a serial entrepreneur, controlling your own destiny, why did you decide to... Because I'm sure you could have negotiated it such that you didn't have to go work at a company.
HitenI think that...
LubaWas it a curiosity to explore what big orgs were like?
HitenI think it's very hard to work out, at the earlier stages, a situation where you're not coming with the company. So that was one thing. So, yeah, it 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. So no one was coming in like, oh, this crazy person is going to come here and be crazy. They were like, oh, this crazy person is going to come here, and they're going to be crazy, and we know why.
LubaThey'll figure it out.
HitenRight? But thankfully, I was able to help recruit my boss. I would, you know... I'll never work for anyone again, but I would definitely work for him again. I don't wish that upon him, though. Or very self-aware, or anyone else. But I think we did okay.
But, like, basically, founders don't realize when they're at a peak of value. And when you have investors on your cap table, you can either, you know, say, hey, look, this is an experiment, we're going to keep going and, like, try to make it big, which we could have done. We had 18 months of runway. But instead we were like, well, the way the previous year went, and the year before that went, pointed to 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, that we could have done, and we were going to do, and those were our plans.
But then if someone was going to come along and 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 didn'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, because so many things collapsed after in the world. And they were already collapsing before, because growth was very hard in 2023, because budgets were collapsing at the time. And so an earlier company doesn't have as much stability. We had enough, but not enough to say, hey, if we go the next 18 months, we're going to get a Series B for sure. And so between the peak of value and that calculation, it made more sense.
LubaYeah. So it was just that self-awareness that it was better to sell.
HitenYeah. 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, or myself, etc. And, like, 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. Otherwise, go self-fund a company, especially with vibe coding and all that. You could do that and not have to raise any money. But if you raise money, go big or 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 18 months and try to figure it out. And no one was going to stop us. They didn't even have the ability to, mostly. 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 were all right with, then, like, if we found an opportunity to do that, we should do that. So that's kind of the full calculation that happened.
But really, it's just peak of value. If you're at a peak of value, your job should be to try to capitalize on that peak of value, regardless of anything. Like, even if you want to go public, like, you're at a peak of value, like, you should entertain, 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 had a 50/50. My co-founder might say less, because she's more conservative, but I think it was a 50/50.
LubaThat makes sense.
HitenEspecially knowing what I know now. Like, more conviction on certain things, you know?
LubaOkay, in the interest of time, I really want to dive into the topic of personality tests, since we haven't, and that's a very interesting topic. So I was very surprised to find out that you were into Human Design, which I feel like is kind of niche. 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.
HitenI think people who have very clear goals that they've had 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, because they are probably not going to perceive a problem.
LubaBut 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 of questioning is when you go down personality tests.
HitenI just want to make that clear, because people listening might not realize why they don't care about this.
LubaOr maybe this makes me think of, if something's not broken, why dive into a lot of, you know, self, like, self-digging?
HitenThere's people close to me, in various ways, that will never care about this stuff. And so I just wanted to address them first. They will just not care. And the only thing I can think of, or 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 it. But you are right, the second that gets tripped up, this can be helpful.
LubaSo on those people, because I'm kind of jealous of the person who's so clear about their goals. Are the goals very simple goals, very clear goals, or not really? Like, what's the archetype of that person?
HitenYou 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...
LubaDo you think they know themselves? Or do you think they're so convinced that they know themselves, but it's not actually true?
HitenI think that they haven't found a value in knowing themselves better.
LubaOkay. That's fair.
HitenWhy do you need to know? If you find a value...
LubaIt doesn't matter.
HitenIf you find the value, you're gonna dig in. To your point, like, they have a problem. So the value is, I've got to solve the problem. I've got to solve the problem. So they'll find the value in trying things to solve the problem. And that is why people go on the ayahuasca trips, all that kind of stuff, right? Like, symbolizing, go find myself. It's like, you're right here. You don't need to go find yourself. You're right here. You don't need anything. Like, anyway.
LubaYeah. Okay. So for people who are very clear, they know themselves, this is, you know, skip this section. Not important.
HitenIf you think you know yourself, or you don't care, right, for this, it's fully fine. So in general, 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. 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. I'll 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. Take that. You want to talk about it? I'll help you. You want to ignore all the other stuff? I don't care, right?
So I think with some of the stuff, folks get very caught up in the, how does this thing know this?
LubaYeah, yeah.
HitenInstead 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, Color Insights is another one... There's a bunch of these. 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.
LubaAnd so in your experimentation, your favorite ones are Enneagram and Human Design.
HitenYes.
LubaAnd how much time do you 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.
HitenNo, it was more bumping into things, then trying them and seeing if I like them.
LubaWhat's an example?
HitenHuman Design.
LubaLike, what's an example of... Give me an example of something you learned from Human Design, and you ran an experiment to figure out.
HitenOh, got it, got it, got it. I think Enneagram is interesting on this one. So at Dropbox, like, internally, we had an operating system thing, so an internal operating system that had the org chart and a bunch of other stuff. There's a field for Enneagram, because I think Drew really likes Enneagram. He's an Enneagram seven. I think it's out there.
LubaOh, I'm an Enneagram seven. Yeah.
HitenAnd I'm a nine, and my boss is a five, or was a five.
LubaDo you believe... So just to interrupt you for a second, that you need to look at the primary Enneagram? Because, you know, there's, like, three top Enneagrams. Is there any value? Because I'm a primary seven and then nine.
HitenYeah, a wing. Yeah. 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. Like a three, a six, and a nine. It's funny: my brother-in-law is a three, my wife's a six, I'm a nine.
LubaOkay. So Drew really likes Enneagram. So at Dropbox, you guys were really into...
HitenSo we had Enneagram. So it was like... I wouldn't say, like, it was cultural, but I'm sure at some point it was, because we know his. A lot of people will put theirs. I put mine.
LubaIn Slack, instead of the, you know, circa-2019 pronouns. You put yours in your card.
HitenThere you go. That's it.
LubaI like that better.
HitenYeah. And so basically, I had ChatGPT set up where I could go and be like... at one point... Because my boss is someone I've known for 20 years. The time we would get on a one-on-one or a call was very precious, because, like, we both valued it, even if there wasn't much to say. So we tried to do it. But he was 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 a.m. on a Saturday and he can make it, I'm fine. Like, I'd love to talk to him. This is one reason I'm here, right? Probably one of the bigger reasons, because working with him was incredible. I learned a lot, and I didn't even think I'd learn anything. Not from him, but from generally that experience. Or I didn't think I'd learn things I would take with me, in the way that I am, is what I said.
LubaWhat was the biggest thing you learned from him?
HitenThere's a lot of things I learned from him. I think I learned more about myself from him, by him managing me and the way he did, because it helped me understand things about myself that I hadn't quite clicked on. I'll give you a couple of examples. At one point, our one-on-ones, like, we didn't have them consistently. And, you know, there is one mantra, which is, like, if you're managed by someone and you're not having one-on-ones, 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, because I wanted to spend the time with him. And I know he was fine with that, because he wanted the same, but it was very hard.
So at one point I hit ChatGPT. This is after, like, six weeks or something of no one-on-ones, but we were in other meetings. Everything was fine. I'm like, is everything okay? Like, I'm a nine, and I'm, like, just trying to align. And, you know, my Human Design and stuff... I knew what I was looking for very clearly, actually. It's like, oh 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 I found is, in this work, like the personality and all that work, ChatGPT 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 ChatGPT, because 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. 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. It 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 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're basically trying to make sure that whatever you build continues for a long time. 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 lasts beyond your time there.
I was like... I can't dive into the specifics, 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, to be clear, it wasn't the processes of building. It was actually the... That's why I don't want to share it. 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 subconsciously was building that way for that reason.
LubaOne thing that comes up for me on that is how to decouple your reaction of 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.
HitenYeah.
LubaAnd then getting convinced that the way it describes the thing that you did, to yourself, is genuinely, absolutely true. Taking something basically at its face value.
HitenI think that goes back to what we all say now, or are starting to say more, which is, like, essentially the two words are judgment and taste. If it gave me some bullshit, I'd know it. But that's my taste and judgment. And I've spent enough time knowing myself without AI that, like, honestly, in that personality side, 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. Because now I'm like, oh, okay, I don't need to build like that in other scenarios. Or if I'm building like that, there could be this hidden reason that I didn't see before.
LubaI want to ask some nitty-gritty questions. So you mentioned at the very beginning of our conversation that you have this project set up in ChatGPT now that understands you, and I assume it's based on Enneagram and Human Design. Tell me more about how this project is set up.
HitenThis is actually the one I use for these things.
LubaYeah, yeah. So it's a project. What's in the project files?
HitenYeah. So the project files are my Enneagram.
LubaLike, just the...
HitenLike, the instruction knows my Enneagram, and I just told it the nine, maybe a wing, whatever, I mean.
LubaOkay, okay.
HitenBecause it's AI, like, you could put as much context as you can.
LubaYeah. So this is an instruction. So it's not a file.
HitenThe Enneagram is an instruction, because there's not much more to it. Like, none. Well, and I assume the AI already knows about Enneagram...
LubaYeah, which is true.
Hiten...which is true. But if I was using an AI that didn't, for whatever reason, like a local one, or whatever it is, even a local one...
LubaYeah. Let's just talk about ChatGPT.
HitenYeah. So 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 the artifacts are more, like, my Human Design chart, or any other context that I want to share in there, because it doesn't have my chart. Even if I gave it my date and all that, it's not going to go make me my chart. So I want my chart. But I can assume it knows about Human Design, because there's a lot of publicly available materials. Tons and tons. Perfect. Great. So it's mostly things like that. So if I had an MBTI report, any reports... I had my Color Insights, I did that many years ago. I shoved that in there too, even though it's kind of old and stale.
Yeah. And then I had a long-running chat on that one, but it could easily have been 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, he built a manual. Like, you know, some people do the operating manuals, especially execs. So he built a manual. And that manual was what I used in the chat, not as project files, but in the chat. I'd be like, 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...
LubaYeah, yeah.
HitenYeah, right? And that was interesting. Yeah. Nothing bad. Just very interesting to see how it broke it down, why he wrote the stuff, you might not understand either. And so that was cool. But then it was, like, asking these kinds of questions, or, you know, that one. What I did also is I actually took his manual and made a project for it.
LubaOkay. Yeah.
HitenIt was like the Morgan bot. And then I was even helping colleagues with it. But, like, it was giving, like, such accurate Morgan-like feedback.
LubaThat's amazing.
HitenBecause it was between knowing his Enneagram Five and then having his manual.
LubaAnd so now that you have this project with instructions and your Human Design chart, whenever you have more of a personal... you know, when...
HitenWhen I want to understand this, or I said this, I felt like...
LubaYou start talking.
HitenYeah.
LubaAha.
HitenEasy.
LubaGot it. Okay. That's awesome. Yeah. Okay. Completely switching gears, I want to know how you post so much content. What's the system?
HitenYeah, yeah.
LubaThere's so many tweets, vlogs.
HitenI need to do better on some of that. 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. A long time ago, I studied it, because we were building a bunch of content stuff and wanted to understand it. And that's just studying, like, how people created blog posts. Like, nothing fancy. But that got me to a framework, 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 lots 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. And there's gold.
LubaDo you still write a lot of notes now? What's your system for writing notes?
HitenI just use the Notes app on...
LubaAnd right now, do you use voice-to-text?
HitenI use voice-to-text. Sometimes I'll do voice memos. Yeah. Everything, okay? Because 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.
LubaGot it, got it. So you have a bunch of notes. Okay.
HitenYeah. And then literally, like, I want to write something? 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. I'm just using it as an editor. I'm using it as a researcher and editor.
LubaAre you systematic about when you sit down to actually distill your notes to write content? Because, 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 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.
HitenSo, like, if you're good 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.
LubaSo you're allowing yourself to do that?
HitenYeah. Like, for example, after this, I might walk away with some insight into my mind, and I might just post it and call it a day. So 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. I'm posting once, say, I'm posting once a week, 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...
LubaWhat tools are you using for your content? And do you schedule content? I assume you schedule content.
HitenI schedule content because I have to. Otherwise it goes out at any time, which is bad. So I use Typefully, only for scheduling, Typefully.
LubaThat's for Twitter, or for anything?
HitenTwitter. Anything.
LubaActually. Got it.
HitenI used to use Buffer. I think Buffer is a little heavy, weighty for it. And Typefully really figured it out for Twitter, where 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. Because, and I've tried many things over the years, even back in the day... I was one of the first 5,000 users on Twitter.
LubaWow.
HitenWe actually built a... It was called Twit This at the time. Twit This, for whatever reason, not Tweet This. But we actually built the button before the button existed. And it was Tweet This or whatever, now it doesn't matter. So, really early there. We even built a... I had an engineer build a script, a PHP script, and that was a thing to do scheduling. This was before Buffer and all those things existed. So it's something I've been doing a long time. It's just the short of it.
But that's for scheduling, because that makes that easy. And then the majority of it is just whatever. I actually deep-research a lot, because I find that to be really helpful, whether it's Perplexity for some of it, or ChatGPT, or even Claude, in order to get context or examples, or help me validate something I'm thinking, when I'm writing something bigger or more thoughtful. 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, because I wanted to do cross-posting, I would use, you know, Twitter has a native scheduling feature.
LubaYeah, yeah, yeah. But now you also do video content. You've had podcasts multiple times. What is the process there?
HitenFor the video content, I found a team that iterates like it's a product. And so we're still iterating, but we're getting there. And now, you know, with my lisp and the voice, we're working on some stuff where we can fix that problem in the content. So I've been looking for this team for a long time, and they just happened. I found them a couple of years ago and really enjoy working with them. They're also working on, like, I have a daily operator links newsletter right now. They're the ones that built that out and are working on it. So 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. But they're building the systems and helping me view a bunch of them. That's just an experiment we all wanted to run.
I'm trying to think if there's anything else useful there. I think it's so easy to create content these days. Like, I'll give you another example. A very good friend of mine, 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, or I'll take a transcript of his and turn it into really good content. Really good at speaking. 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: just give me your transcript. You're brilliant. Give me your thoughts. Awesome. And I'll help you turn it into content. And it was super easy. Like, his transcripts are that good. Like, some of the best... AI 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 gave 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, 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.
LubaCan you give me one concrete idea for how you take one insight or an idea and turn it into multiple pieces of content? Like, basically, digesting one idea into, say, five tweets?
HitenYeah, I think one way to think about that, if you really want to push it really far, is if you... And 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.
LubaBut you could use it as an idea generator.
HitenYeah, 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've found a lot of ways to get it good enough, or right. But basically, like, okay, how about this: you give me an idea, and I'll tell you how I'd walk through it.
LubaOkay. Very simple idea that I think can be turned into a lot of pieces of content. But I'm always like, all content should always be original. Take action. Action precedes clarity. How would you turn it into a lot of different pieces of content?
HitenSure. Yeah. That's great. So I think the first thing I would do on something like that is actually, like... And this is if I'm playing around with the idea. So this is, like, more of an exploration exercise to find topics. But I don't think you can write something without knowing who you're writing for. So first of all, that's why it's just an idea. The topic includes a bundle of who you're writing for and what it's to say and whatever, in my opinion.
So I would put that in ChatGPT and be like, I would love to get different perspectives on this statement. And then usually, when I do just something like that, I get so much gold in what it gives me back. Because it'll say, well, if you're this type of person or this type of person, you'd 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 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 this will resonate, or this will. Then it'll give me the prompt. Then I'll go run the prompt, and then I'll go bring the research back to that chat, because I'll do it in separate chats, and be like, okay, this is what I got back. How should I think about this? Or how should we think about this? What are the pros and cons and all that? So I'm more using it as that thinking partner that you essentially never had, to help you essentially deconstruct, reconstruct, repurpose an idea.
LubaI 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.
HitenI actually thought it was good, if you're going for that kind of content.
LubaOr, like, motivational content.
HitenYeah, absolutely. I think it was good, because you might even find more practical stuff right from there as you start sort of digging in, right? But a more practical one... One of my favorite ones, actually, and I think everyone should be doing this, is basically, like, tell a story. So I'd rather start with a story, and a story that's real for me. We talked about many stories today. So 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 four years old, I thought...
LubaThat.
HitenSo I'd probably go 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, which is, like, the earlier you start, the better. I started at four years old. 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 an 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...
LubaYou could...
HitenAs a result of that, I can get things that are closer to my voice with fewer edits. But it's still very hard to get AI to write in someone's voice. It's not impossible. 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 themselves.
LubaFiguring that out first. To wrap up, I wanted to ask you some short questions. What is your life philosophy, in one sentence?
HitenIt was all a dream.
LubaI have to ask a follow-up about this. Can you elaborate?
HitenWe're having an experience right now. 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, but 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. The philosophy is: it was all a dream.
LubaSo 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 reality is different.
HitenThat's definitely a part of it. Another part of it for me is the idea that 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. So, one word: presence. The sentence: it was all a dream. Because I think that's how you get to presence, as weird as that sounds.
LubaI love it. What is one trait that you have that you're really grateful for?
HitenYeah, I don't know where... 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, the one I probably value almost more than any other trait, is empathy.
LubaOh, interesting. I thought you would say curiosity. Okay.
HitenOne might lead to the other, depending on how you think about certain aspects.
LubaWhat advice do you give the most?
HitenThere's a statement that I said to my co-founder, but before that, I said it to the person who introduced us. It has nothing to do with that relationship or anything. And so this is probably the one I would say. I'm not able to say it to most people exactly like this, but underneath, if anyone's gotten advice from me, they're going to understand this. Underneath it is essentially the statement, which is: the only way to do more is to do more. Take that however you want. It's super philosophical. 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 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. I'm just saying, if that's true...
LubaYeah. Yeah, yeah.
HitenWhat are you doing?
LubaYeah.
HitenRight? And then you start thinking about that from me being a founder. Most successful founders out there... I don't know a founder who is not doing more to do more. Like, why does Elon have so many companies? Why does Google have so many products?
LubaThe only thing that this makes me think of is that you need to really understand yourself to see what is the outcome that you want. And if the outcome 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.
HitenYou went to things. You equate more with things. They don't have to be things.
LubaOr just, like, the life that you want to live.
HitenMore execution, more ideas. Like, let's put it this way. And in today's world, I think this is more real than ever. 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.
LubaIs to do more things.
HitenYeah, whatever way you want to look at it.
LubaYeah. And what are you excited about in the next ten years? Although I realize the next ten years is very uncertain. What are you excited about in the next year, or five years?
HitenI think the word that comes to mind is opportunity. And I think, like, part of this is just looking back and saying, like... because I probably think a lot more than I should. So looking back, it's like, where were the things where 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 an abundance of opportunity. I think there always is. But right now, there's an abundance of opportunity because of the uncertainty around how fast and exactly how things are going to change, which is some of the most fun times you can possibly have. As long as you're not sitting there worrying about everything existential that you don't control. So those are all the caveats.
LubaThank you so much for your time. This was an awesome conversation, as always. Thank you.

