HaseebQureshi

LubaHi everyone, welcome to The Luba Show. Today my guest is Haseeb Qureshi, managing partner of Dragonfly Capital, a $4 billion crypto venture capital fund. And him and I talk about such a rich variety of things, ranging from manhood, crypto, Airbnb, where we both met almost 10 years ago, and so, so many more things.Link

This was a particularly fun conversation because, again, we've known each other for such a long time. We're probably going to be celebrating our 10th year friendship anniversary next year. So it's really fun to spend time with someone who's as smart and as thoughtful as Haseeb is, but also someone that I know so well, and we probably haven't covered some of these topics in as much depth. Haseeb, I'm really excited to have you here. Welcome to The Luba Show.Link

HaseebThank you for having me.Link

LubaOkay, so I'm really excited to start actually where we first met. Let me set the scene.Link

HaseebPlease.Link

LubaSo, I was at Airbnb's micro kitchen, and you were walking in to the micro kitchen.Link

HaseebThey have many micro kitchens.Link

LubaYes.Link

HaseebI think we were at Cairo.Link

LubaYes. Good memory. It was Cairo. Yeah. And I distinctly— so, to set the scene again, you just wrote that negotiation blog post that went viral in the tech community. And the blog post was basically about you getting all these different tech offers. And it was very controversial to disclose salaries back then. But in the blog post, you very openly and transparently talked about what Yelp has given you, what Google has given you, what Airbnb has offered you, and the fact that you then negotiated Airbnb from, whatever, like, 120 to 250 total comp or something along those lines.Link

And to paint that blog post going viral, Business Insider had this really popular article about you with your face plastered on it. And it felt really douchey. Like, it just kind of, you know, felt like, who is this fucking guy talking about making so much money? And so I of course had seen this blog post, and I remember you walking into the micro kitchen, and I had this thought, wow, this is that douchebag guy with the blog post.Link

HaseebWow. I don't think you've ever put it in quite those words before. Thank you.Link

LubaBut then, you know, we started talking, and within minutes my opinion of you completely 180'd. In fact, you also convinced me to join the team that you were on, because I was in the bootcamp at the time, and you already were working on fraud prevention, or risk as it was called. And yeah, I actually decided to join that team because your pitch of it was so convincing, and you were actually so likable in comparison to the article.Link

HaseebWhat was my pitch?Link

LubaWhat was your pitch? I think you were telling me how I'm going to learn so much as a backend engineer, and I'd never done backend before, and how fraud is like a cat-and-mouse game, and I'd be learning so much about so much.Link

HaseebThat was my pitch? Wow. I do not remember pitching you.Link

LubaYeah. Yeah. You pitched me and you got me convinced. So basically, you kind of, like, completely changed that first impression that I didn't even have from meeting you, but had from the article.Link

HaseebBut do you remember that? I remember meeting you in Cairo. I don't remember pitching you on the risk team. My first memory was, I remember I came to help you debug something.Link

LubaOkay.Link

HaseebThat's, like, the first memory. But I remember meeting you in Cairo, and you were, like, grabbing some popcorn.Link

LubaPopcorn. Yeah. Popcorn.Link

HaseebAnd I remember talking to you for a little bit. I did not remember convincing you of anything, but I remember helping you debug something. And you were the newest intern on the team, or, no, you had just graduated from being an intern. You were the newest person on the team, you were the most junior. And I, of course, had just joined the team.Link

LubaYeah.Link

HaseebAnd I felt, naturally, after writing this blog post that went super viral— that was kind of a very revealing post about going through this very arduous, crushing job search that was going nowhere, and then suddenly it finally started to get— I think I talked about applying to, like, 30 companies, not getting a single callback, and then I finally got offers.Link

LubaYeah.Link

HaseebAnd then I finally— eight offers. I finally ended up getting eight offers, culminating in Airbnb, which was a super hot company at the time. And so, you know, fresh off of that, writing that blog post and then having it go immediately super viral, right? So my blog had, at the time, probably, like, a hundred readers.Link

LubaOh, there were only a hundred readers?Link

HaseebYeah.Link

LubaWow.Link

HaseebLike, because it was, like, a bunch of people I knew from App Academy, the coding bootcamp I was at, as well as from my former poker life as a professional poker player, who kept following me after. I was a nobody, you know? Like, I just kind of wasn't a very public person at the time. And so they just wanted to know what was happening in Haseeb's life, and I was like, well, here's what's happening in Haseeb's life. And so I did not expect it to become, like, a big thing.Link

And so when it went super viral, everybody at Airbnb knew not just how much I made, but, like, everybody had an opinion about me as a person. And, like, I remember the first week I got called in to go meet with the VP of engineering and the GC, and I thought I was going to get fired. I was like, okay, well, game over. Like, I just announced that I got this amazing offer, and now I'm losing it. But they were chill about it. But everybody at Airbnb kind of looked at me like I had this stank on me.Link

LubaYeah.Link

HaseebAnd that I wasn't supposed to be there, you know? That, like, I had cheated the system or something. And I remember going into Slack, I could, like, search my name and read the conversations people were having about me, because, like, people just weren't thinking about the fact that, like, I'm here. Like, I'm fucking in Slack just like everybody else.Link

So anyway, I had so much imposter syndrome, which, like, of course I'm going to anyway, regardless of whether people know this about me. But now it's like I have imposter syndrome and I think everyone's looking at me and judging me, which they actually were. And so I remember helping you debug some random thing in, like, a, you know—Link

LubaAir-something, probably.Link

HaseebYeah. I don't remember what it was. Something. And I was actually being helpful, and I remember being like, oh, wait, maybe I can do this. You know, maybe I actually am qualified to be here. So I actually felt really good in our first interaction, or, like, the first substantive time that I was helping you with something. And then you were probably like, oh, this fucking douchebag is—Link

LubaWell, to be clear, I felt really good about our first interaction too, following, you know, debunking my overall first impression based on that Business Insider article. But yeah, I was actually curious, how did you feel with people kind of looking down on you when you joined the company? And were you actively trying to change that image?Link

HaseebI mean, I was aware of it in the sense that, you know, I kind of knew that everybody had read this thing and everyone was talking about it, because it was front-page news in tech circles. And that being said, I think for the first couple weeks, like, when I would look at people, I would wonder, like, oh, is this a look of recognition, or is this just, like, oh, hi, new person? You know, or, like, oh, it's that guy.Link

After a while I stopped thinking about it, because, like, naturally, you know, people just stop thinking about it, or they just forget that you're the guy from the thing. But I was mindful that this is the first impression for a lot of people. And so I have to prove myself not from, you know, what I say, but from what I do.Link

And so, but I felt like I was going to do some of that anyway, because I'm the new guy. You know, I was older than most people who were coming in at my level. I didn't have a computer science background, didn't study technology, didn't go to any— you know, studied liberal arts at a state school. I was not the stereotypical Airbnb new hire. And so I really wanted to prove myself. So that accelerated my need to prove myself to other people.Link

LubaAnd to paint the picture, when you were writing that blog post, TC, total comp, there was no transparency around it. Because obviously now there is Levels.fyi, there's Glassdoor, everyone talks about their compensation.Link

HaseebYeah, there's stuff like, what's it called, Whisper—Link

LubaYeah, oh yeah. Blind.Link

HaseebBlind, Blind. Yeah, stuff like Blind. Yeah, no, at the time that culture was not as well developed as it is.Link

LubaOkay.Link

HaseebNow, it's funny, because, like I said, I had very few followers on my blog, so I wasn't, like, trying to make a big statement to Airbnb. I did not think anyone from Airbnb read my blog or would read my blog, cause, like, why would they? They don't know me.Link

So I actually, when I was doing my job hunt and thinking about how I was going to negotiate, I read another blog post written by this guy, I forget his name, but he was, like, some guy in the rationalist world who wrote basically the same thing that I did. He wrote a post about his job hunt, the offers he got, how he negotiated, what his strategy was. And when I read that, it was extremely useful. Just informative, to just understand, oh, this is what's happening.Link

And, like, on some level, why does it matter? Your job hunt's over. You have your job. Like, you know, who cares? Like, what are you revealing that's going to hurt you at the point at which your job hunt's already over? So I thought, like, it's going to be helpful to the people who are searching for a job, who are maybe at App Academy, who are applying to jobs themselves after going through a coding bootcamp. But for me personally, I don't give up very much by just telling people what happened.Link

I didn't appreciate how political it was going to be to say how much money I had made and the process of getting a job. Because I realized, like, okay, so for people in the tech community, the reason why they care is that, oh, now I know, or people at Airbnb, now I know how much other people are making. So I actually had a few people DM me and say, thank you for posting that, because I didn't know that I was being underpaid.Link

Now, a bunch of people obviously were like, oh, this guy's a douche. But it's funny. I remember this very vividly, because I was looking up in Slack what people were saying. And there was one group where people were like, how could this person have gotten through the values interview? Because obviously this person is a douchebag and not aligned with the values of Airbnb. And then somebody else was like, well, you know, never mind the values interview, how did they get past the tech interview? Obviously this person, you know, they just graduated from a coding bootcamp two minutes ago. They don't know anything. Like, something's wrong with our interview process that this person even got in.Link

And then one of the people who was, like, you know, an L6 or something, who did my phone screen, piped in and said, I was the guy who did his phone screen. He actually did really well. And I read that, I was like, okay, at least somebody out there— like, so not everybody thinks I'm an asshole.Link

But from the perspective of, like, okay, so why did this go viral on Business Insider or on TechCrunch? The reason why it went so viral there was not because, like, oh, this guy is, you know, talking about his salary. It was because, look at how crazy Silicon Valley is. Look at this guy, this loser who has no skills, doesn't know— he went to some coding bootcamp for, like, two months, and now he's getting all this money, and Silicon Valley's so easy to fool, these idiots. Look at this poker player, gambler, you know, con artist, managed to con his way into all these coding jobs.Link

And, like, that was the angle that they ran with. And I understand why that's a sensational story. That's obviously a great story, because the story that people wanted to hear was that there's a tech bubble. And it's like, oh, here's the proof of a tech bubble. If there wasn't a bubble, how could you explain this guy, this total idiot, getting eight interviews just cause he's, like, some, you know, scrappy negotiator or whatever? And so that story, again, it's, like, kind of a broader political story. I was an example of a story they wanted to tell.Link

LubaSo, I love the fact that you mentioned the Airbnb values interview and how people were like, how did he pass the Airbnb values?Link

HaseebYeah.Link

LubaIn my preparation for this conversation, despite having known you for many, many years, I decided, okay, let me actually read your blog. So on your blog—Link

HaseebYeah, of course.Link

LubaIt's a privilege. But anyway, so on your blog, I thought it was really funny how you were like, I'm so excited to join the Airbnb family. I actually cracked up reading that. And to paint a picture for the listeners, you were very different from the traditional Airbnb family. I was encompassing a lot of that vibe and values, you know, being very in, being very social. But you were, like, very much not just an outsider from the technical standpoint. In a lot of ways I was an outsider too, cause I didn't study CS and I was self-taught. But you were, like, a cultural mismatch in some ways.Link

HaseebYeah.Link

LubaSo I'm curious, what were the expectations and reality when you did join, and how did that shape you?Link

HaseebSo Airbnb was probably my first job at a real company. So before any of that stuff, before Airbnb, before all this, I was a professional poker player. And being a professional poker player is just such a different universe than, like, you know, normal gainful employment, where you have, like, a boss and you have OKRs and you have performance reviews and all that. I had never had any of that before in my life.Link

So I worked for a little while at App Academy, which is the coding bootcamp that I went to. They ended up hiring me, but it was, like, you know, a small company with, like, I don't know, 12 people, and they were just kind of teaching people how to code. It was so not what I was prepared for going into Airbnb. And so, of course, I had a naive perspective about what that was going to be like. And I was like, oh, it'll be so great. I'm going to work at this company and I'm going to rise up the ranks and I'm going to do all the things they want me to do. And Airbnb at the time, I think they were ranked, like, one of the best companies to work for.Link

LubaYeah. Yeah. It was really hype, hot, to be at Airbnb.Link

HaseebThat's right. That's right. It was a very, very competitive company to join.Link

LubaAnd very hard technical interview process.Link

HaseebVery, very challenging technical interview. But, like, the perks, the, you know, the fancy, you know, the, I don't know, the coconut water and the nuts and the snacks and the whatever, all the stuff that they give you, it was all very, very nice. Very bougie, comfortable, pampered kind of corporate existence.Link

And I just absolutely did not care for any of that, you know? Like, I think I didn't know how I would respond in that kind of environment. I think I thought, well, you know, I will play the game that is presented to me. But I don't know, constitutionally, I'm not, like, a, you know, I'm not a team player, you know? I'm much more of a go-my-own-way, like, lone-wolfy, like, I will get it done. If you ask me to do something, I will do it. I will do it well.Link

But, like, yeah, I don't want to kind of hang out and celebrate everyone's birthday every day. Like, I mean, it's just, like, literally, we had, like, a 50-person team. Anytime anybody from the team had a birthday, we all got together and we all cut a cake. Which meant, like, every week, every single week, you're sitting down in the same room cutting a cake and singing someone happy birthday. And you—Link

LubaThat was so fun. The cakes were so good.Link

HaseebI just detested that, you know? Cause it's like, let's just work. Let's just do work. Let's get stuff done.Link

LubaI'm surprised that you said you're not a team player, because you lead a large team. You're so good at lifting people up. You're so good at mentoring people, and you work with so many founders that you're helping. Like, that is kind of, like, quintessential team player, working with people.Link

But I guess what you're saying is the whole social activity stuff. Because it is true that anytime you guys do, like, an offsite or any sort of social thing, you would be there, but it's not, like, the thing that you're here for. You're here to win, and to work to win, as opposed to work to, you know, sing kumbaya and, like, be a family and do all of those things.Link

HaseebYeah, I mean, I think that's definitely true. Even today, the way that I run Dragonfly is that, like, you know, we're not all best friends. Or at least they're not best friends with me. Best friends with each other, maybe. It's just not the way that I relate to people, is, like, okay, we work together, so let's be best friends. I am a great partner. I'm extremely reliable. I'm very communicative. I'm very transparent. But, like, I'm not your chum.Link

And I think that's okay for some people. For some people, it's like, well, it's really important to me to be, like, true friends with the people who I work with. In which case, I think those people are not going to love working with me, cause, like, yeah, I'm not going to be your best friend just because we work together.Link

But I think for, like, going the distance and being, you know— I actually resonate a lot with hearing the story about Dennis Rodman, who was on the Chicago Bulls. I don't know if you ever watched the documentary *The Last Dance*.Link

LubaMhm.Link

HaseebSo it talks about the rise of the Chicago Bulls. And one of the things that they mention is Dennis Rodman, who was kind of, you know, the third player behind Scottie Pippen and, of course, Michael Jordan. It's kind of a legendary team, and a legendary amount of teamwork they did in order to win— I think it was three championships that they won together, or two championships, maybe it was.Link

But what they reveal in the documentary is that they basically never talked. Which is kind of bizarre, because they worked together, they lived together, they traveled together, they, like, built this incredible partnership on the floor. They had enormous amounts of trust in each other, but basically outside of the floor, they never talked. And I was like, okay, I'm not crazy. Apparently Kobe Bryant was also the same way, is that he just, like, was a relentless executor, but, you know, he wasn't friends with other people outside of the floor.Link

LubaAnd for those legends, was it something that they personally did, or that was the vibe of the entire team, where—Link

HaseebNo, it's, like, other people were friendly, some other people were. Yeah. I mean, obviously that sets the tone, and, you know, people who really need that are probably not going to self-select into that kind of an organization. But no, I mean, I think it's just different strokes for different folks.Link

LubaYeah. Have you ever tried opting in to the Airbnb way, or, you know, companies like Airbnb?Link

HaseebWhen I was at Airbnb, I tried, but I just found it so excruciating.Link

LubaOkay.Link

HaseebBut I just couldn't do it. Like, I mean, there were just so many, like, extracurriculars that people would do, and it's like, are we doing this to show each other that we're doing this, or do we actually want to be doing this? Where it's like, you know, there's, like, oh, today we're going to take the day off and we're going to go and beautify the city. And it's like, why are we doing that? Do we need to do that? Can we just do work?Link

But, like, I mean, this is part of why people think it's such a great place to work, is because, like, oh, that sounds great to a lot of people. To me, that's like, no. If I wanted to do that, I would do that myself, you know? Like, I have other things that I think are important that I could do instead.Link

LubaDid that teach you that that's something that you definitely didn't want, as far as—Link

HaseebYes. You know, the birthdays thing absolutely scarred me for life.Link

At Dragonfly, like, because there's different people at Dragonfly, there's people who are more touchy-feely, or more, you know, social party people, whatever. I'm obviously not. We had a fight early on of whether we are going to, like, actually celebrate everyone's birthday. We have about 50 people at Dragonfly. That's enough that it was kind of like the team at Airbnb, that, like, every single week it's somebody's birthday.Link

And so the question is, are we going to, like, send them a cake, do a thing, like, we all say, you know, every week on the weekly, it's blah blah blah's birthday today, happy birthday, da da. And I was like, no, we are absolutely not doing that. We can send a message in a birthdays channel about everyone's birthday, and they can decide if they want to, like, get a gift, that we send the same gift to everybody every week. But, like, we're not going to think thoughtfully about it. Like, they all have their own lives. They can celebrate their birthdays with their friends. We're not their friends. If we're their friends, they're doing something wrong.Link

LubaWell, what if someone wanted to self-organize and send a birthday cake on behalf of that sub-team to that person? Would that be appropriate, or—Link

HaseebI mean, it's fine. I'm not going to stop— I'm not the Grinch. I'm not going to stop somebody from celebrating somebody else's birthday. I'm just saying, like, as an organization, what is the norm that we set around the way that we relate to each other? And the answer is: professionally.Link

LubaMakes sense.Link

HaseebSo I have very, very high standards for how responsive you are, how reliable you are, how communicative you are, how transparent you are. But if you don't want to talk about your personal life, or you don't want to let people in as a friend, completely fine. Absolutely fine.Link

LubaMakes sense. Oh, I want to come back to something that you said. I want to come back to your first memory of meeting me, which was helping me debug something. So you definitely helped me out a lot in those first couple of months, because I, similarly to what you said, had, like, a huge imposter syndrome being on the team. And I was doing backend for the first time, and I remember the late nights when you would help me with Ruby on Rails, even though you didn't know Ruby at the time. You were learning all the time.Link

I basically joined, you know, a fraud team, which was very out of the park of anything that I was interested in or good at, I guess, by that time, because I wanted to take on the challenge. I also started doing backend, which I'd never done before. I was coming from the Android ecosystem. So I was like, okay, I want to take that challenge of trying to expand my programming horizons, because I didn't study any of that stuff in school. And then, three, Ruby on Rails was in and of itself also a new language.Link

So yeah, it was, like, pretty tough the first couple of months, also being like, why am I here, you know? Why did they hire me? And you, yeah, you helped me out with the code and explaining concepts, as well as just the mental game of it, of, like, you're here for a reason. You know, they're not idiots putting you— like, you literally did a whole internship where they could evaluate you. And it felt like, you know, you were teaching me, mentoring me. And teaching has been a really big part of your life.Link

HaseebYeah.Link

LubaI am curious, where does that instinct to teach come from? Why do you like it so much?Link

HaseebWhere does that instinct to teach come from? It's definitely true that I'm both very inclined to help people and to mentor and teach where I can. I also think I'm very good at it. That's probably come in part from me doing it as much as I have. Even when I was a poker player, I was also a teacher at the same time. I taught a lot of people how to play poker at a high level. And, you know, obviously when I got into programming, I also then taught programming.Link

So I think for me, like, if you're asking about the genealogy of where that came from, it probably came from, honestly, my mother. Not because my mother is a great teacher, but actually more because my mother needed to be taught.Link

So my mother, when my family immigrated to America, you know, my dad moved here, he was, I think, 23, my mom was 22. My dad spoke English. He entered into a master's program at Texas A&M. My mom did not speak any English at all. She basically came to America completely bewildered by the culture, the norms, how everything worked. She, you know, she'd never been out on her own or self-sufficient.Link

And I grew up with a mom who still did not speak English. She didn't speak English until I was probably six, seven years old. And even then, very poorly, right? It was very difficult for her to navigate the world. And so as a child, because my dad would travel a lot, he had to go travel for work, we had to help her to navigate the world and to help explain things to her so that she would understand them.Link

And so growing up, like, that was just something that I had to be able to do, because otherwise, like, my mom was not going to be able to survive. And I suspect that's where a lot of my proclivity for teaching and mentorship comes from. And, like, I think that's part of the reason why I'm very good at explaining things in a simple way, is because I did it so much when I was a kid.Link

LubaUntil when did you have to do it for your parents, or for your mom specifically?Link

HaseebOn some level, I still do it. I think her English started becoming much more self-sufficient maybe when I was, like, 12, 13, something like that.Link

LubaSo quite a long time. Got it. And I think you almost— you were, I think, leaving Metastable to launch a course and teach a course.Link

HaseebThat's right.Link

LubaSo your desire to teach was as deep as, like, potentially doing a career transition, or a career block of, like—Link

HaseebIt wasn't a transition. It was more like a project where I wanted to create this online course about learning cryptocurrencies and blockchains. I taught a course about that at the Bradfield School of Computer Science back in, must have been 2017, which was, like, this kind of elective school, paid school, where computer scientists could go, or, like, programmers could go and learn some computer science concepts to keep themselves fresh. I taught a course on cryptocurrencies then.Link

And then I decided that I could take that material that I developed for that course and turn it into an online course that was more built out and more self-sufficient than anything that existed at that time. Because back in those days, like, there just wasn't a lot of educational material about crypto. Most people at that time were self-taught. I was self-taught.Link

So I wanted to do that in between jobs. I thought it would be a quick thing. I thought it'd, you know, take me, like, three, four months, get it out there, and then I would go get another job. But yeah, teaching has always been in my bones. It's just something that I both enjoy doing and that I feel is really socially important and valuable to do.Link

LubaHow are you getting your need for teaching fulfilled right now?Link

HaseebIt's a good question. I mean, as a VC, I do mentor a lot of founders, and that's intrinsically teaching. I think there's also the people who I mentor within Dragonfly. And then I do a lot of public communication about crypto. I write a lot. I do podcasts, and all that stuff, again, also encompasses teaching.Link

One of the things that, you know— so we did this podcast called *The Chopping Block*, and initially I was not the moderator for it, but I ended up becoming the moderator because I was just the best communicator. I mean, the moderation requires a lot of different skills, but one of the most important things is just explaining what the story is that we're talking about.Link

LubaIs that controversial to say? Are your colleagues on the podcast—Link

HaseebI think they would all agree with this.Link

I think initially I was kind of like, okay, I don't want to be, you know, kind of presumptuous, or kind of, you know, whatever. Like, I don't want to be a dick and say, yeah, I'm obviously the best at explaining things, I should be the moderator. And so I deferred to, like, oh, who wants to be the moderator? Okay, we'll give it to you. And it was external feedback that said, Haseeb, you should be the moderator. Why are you not the moderator?Link

So that, I think, in large part comes from me being able to very simply explain very complicated things that are happening in the crypto industry in a way that most people can understand.Link

LubaHow did you get so good at simple communication, and just actually being both articulate and being able to explain complex concepts in simple words? Has it been intentional, coming through writing, or did you put some— or was it natural?Link

HaseebI think, so, in large part, it's just getting the 10,000 hours in. I've just been teaching for such a long time at different things, right? So whether it was, you know, what I'm talking about, of, like, sort of growing up with my mom and helping her to understand how to navigate American life, or whether it's, you know, when I was a poker player, teaching for so many years as I did. You know, I created courses, I coached people individually. And then, you know, going into programming.Link

Like, one of the things that I've learned is the way that I can master a new domain is first study that domain and then teach in that domain. There's a hierarchy of learning that, I forget what the name of it is, but it's, I think, very, very accurate, which is that, you know, the worst way to retain something is to just read it. Reading has very, very low retention. Second-worst way is to hear it. Hearing it is better than reading it. Third is discussing it. So if you talk about it with somebody, that's going to make it much more likely to retain. And the most effective is to teach it to somebody else. Teaching is incredibly good at solidifying knowledge for yourself.Link

And I learned that at a very early age. A big part of the reason why I teach at different things, like, why did I teach poker? Why did I teach programming? The answer was to make myself better at it. And actually, even insofar as I'm helping other people, I'm actually helping myself even more.Link

LubaSo if someone wants to learn something new and they're very short on time, how do they stretch themselves to teach someone? Like, what is your advice for that situation?Link

HaseebFind somebody you can teach it to. That somebody may be, you know, the person who's right behind you, or at the exact same level of proficiency as you are. Teach them what you just learned in the last 20 minutes. Like, any kind of teaching requires you to repackage what you've learned in a fluid way and transform it into a way that you can actually explain to somebody, and it will land.Link

And as you teach more and more, you develop an intuition for when people are just nodding or when they actually understand. And the easiest mistake to make, and this is the thing that bad teachers do the worst, is that they look for approval, not understanding, right? So if you explain some concept to somebody and say, okay, you know, here's blah blah blah, do you get it? Nobody is going to say, no, I don't get it. So looking for the recognition, the understanding, and even challenging that understanding and saying, okay, explain back to me what I just told you, that kind of thing.Link

I mean, I remember teachers in high school that are just, you know— most teachers are terrible. My teachers in high school were absolutely awful. And it's just so obvious that they weren't even really interested in knowing how much of what they were teaching was getting retained. And as a teacher, that to me is like, why would you not be interested in whether you're succeeding at the task? Like, isn't that the point, right? If you're going to do it, successfully do it. Otherwise, like, why bother? Why are we even here?Link

So as a teacher, I'm always trying to find that understanding. And if you don't find that understanding, you fucked up. As the teacher, you fucked up. Now, it could be you fucked up because you explained it badly. Could be you fucked up because you explained it badly for this person. It's not that the explanation is bad, but that that's not the right explanation that's going to land for this individual. Or it could just be that you were overestimating how interesting you are. And it's not that your explanation was bad, it's that they just weren't paying attention to you. And if they're not paying attention to you, you also failed. A big part of teaching well is to be interesting enough to be worth listening to.Link

LubaIs there anything that you are trying to learn right now that you're about to start teaching people, or are already teaching people?Link

HaseebI mean, in crypto, I'm continually learning things, and I, you know, see the podcast as the place where I often teach people what I have learned, my understanding of what's going on at the vanguard, or at current events within crypto.Link

Outside, actually, so one thing I am doing is I'm trying to keep myself abreast of everything happening in the AI space. And the way that I do that is I have a little study group with some folks that I know, and every week we read a new paper, and we present that paper to the rest of the group, and we try to explain what that paper is, what the main result was, what they accomplished, what their evidence was for that. And explaining a paper makes you so much better at understanding what's in it than just reading the paper.Link

If you just read the paper, you will notice that your eyes, you know, they glaze over everything in the paper, almost like running your hand over a wall. But that doesn't really mean that you understood it, right? The way that you'll know that you understood it is that you actually can explain it, answer questions, push back, and also identify what you don't understand about the paper. If somebody asks you, like, oh, how did they do blah blah blah? Like, I actually don't know how they did blah blah blah. Let me see. Go to that section of the paper and see if you can understand it. If you can't, you didn't understand the paper.Link

LubaYeah, I definitely have a bit of a limiting belief about myself and teaching, because I just never inherently gravitated towards teaching, and as a result, I'm like, I just don't like teaching.Link

HaseebYeah.Link

LubaIt is true that sometimes, if I really care about something, and if it's someone close to me, I'm very willing to explain and, I guess, to quote-unquote teach. And through content, for instance, sometimes you have to explain concepts. Or when I was doing it on YouTube, I would inherently, like, learn about the thing that I'm talking about, because I had to, in a way, explain it. But I would argue that the subjects weren't particularly, like, incredibly complex.Link

But at the time when we were doing the machine learning study group, I think it was about 2 years ago now, remember how we would go through a rotation where a person had to explain what was going on in the lecture that we studied? I always dreaded those days, understandably, because it is true, you have to do so much more to explain it to others. And I always felt like, okay, you know, I'm not doing that great of a job, probably, explaining and teaching, because my own understanding of the subject was more surface-level than it should have been. And that allowed me to, like, push myself to learn, kind of try to learn, find the time to spend time on the topics when I was presenting. But I need to do something with this, like, limiting belief that teaching is just not my thing, because it's very ingrained.Link

HaseebWell, but it also forces you to notice your own motivation to really understand, right? So again, like, when you're just reading something, you're, like, running your hand across a wall. Like, that can be satisfying for something, right? Just to get a general sense, like, oh, here's what's on this wall. But, like, when you are forced to teach something, you're forced to confront whether or not you actually understand it. And if you don't actually understand it and you don't want to understand it, that's actually very important information for you to understand about yourself.Link

LubaIt's like, oh, actually, I don't care about that subject as much as I think.Link

HaseebExactly. Like, I don't actually really want to deeply understand this.Link

LubaYeah, that's true.Link

HaseebAnd it's important to, like, look at that and not be like, oh, well, I'm ashamed of myself and I'm a bad person for not wanting that. It's more knowledge that you should have about yourself, which is that, oh, this is not important to me, or this is not that important to me.Link

Whereas there are probably other things that, if you realized you didn't understand them, you'd be like, well, fuck, I really want to understand it then. So, you know, you're obviously an entrepreneur. You're building in the dating market. If you realize that, like, oh, there's something about dating economics I don't understand, because I can't explain it to somebody else, that is really bad. I need to go fix that, right? But if you instead were like, oh, I don't understand this about the dating market, I don't care—Link

LubaYeah.Link

Haseeb—that I don't understand it. I'm not really motivated to go and figure out what I'm missing. You can treat that more as self-discovery than as a personal failing.Link

LubaSo, speaking of self-discovery and learning, you went from poker to learning engineering, web development. You went to Airbnb, and actually in one of your blog posts you were like, oh, you know, I know I'm really excited about web development right now, but I know this is not going to be for life.Link

HaseebYeah.Link

LubaHow did you know that? Like, what was going on through your mind then? What did you think you would want to do eventually?Link

HaseebI knew that I wanted to be an entrepreneur.Link

LubaOkay.Link

HaseebAnd I knew that becoming a developer was the most logical step toward eventually starting a company. Because if you can't build something, you have to have some other skill that is useful to bring to the table. And I didn't have any other skills. I, you know, I was a professional poker player. So it's like, okay, I got to have something valuable to bring to the table if I want to build a company. And so being able to build the thing is probably the skill that I'm going to have, cause who knows what else I'd be good for.Link

So that was my motivation coming into Airbnb. So my goal was not to rise the ranks at Airbnb. My goal was to learn how to build stuff, meet co-founders potentially, and kind of build some pedigree, so that people would respect me and think that I was a competent, capable person.Link

LubaSo at which point did you feel like you were ready to leave? Cause you left a year and one month in, basically.Link

HaseebYeah. Right on my vesting cliff is when I left.Link

LubaYeah. Was that the plan all along, or did you just feel like, okay, I'm ready to go?Link

HaseebIt was basically the plan. I was thinking that maybe if I could get a promotion, that I would stay longer, if I thought there was a line of sight to promotion before I left. But that was not in the cards.Link

LubaYeah, I remember how that whole thing went down.Link

HaseebYeah. Yeah. So I was like, all right, never mind then. I'm out.Link

LubaAnd so when you left, you were like, okay, I'm going to go try my hand at entrepreneurship. And then you entered crypto. How did the whole entering-crypto phase happen from Airbnb? Cause it's quite a leap. You know, you were working at a travel company, tech travel company—Link

HaseebThat cares about belonging and hosting and giving people cakes every week for their birthdays.Link

LubaI know. I know. Crypto is very different.Link

HaseebIt's funny, because it's actually not as much of a leap as you might think. Because at Airbnb, actually, one of the early members of the fraud team at Airbnb was Brian Armstrong, who was the founder of Coinbase.Link

LubaWait, well, I knew Brian Armstrong worked at Airbnb, but I didn't know he was on the fraud team.Link

HaseebHe was on the fraud team.Link

LubaWow.Link

HaseebHe did the Sift Science integration.Link

LubaAre you serious?Link

HaseebYeah, which I remember because I worked on some of his code.Link

LubaYeah. Yeah. Yeah. I worked on some of the Sift Science too.Link

HaseebYeah. So, yeah, that's right. There were some places in the codebase where it literally says, like, if error, email barmstrong@airbnb.com. I remember, like, taking out that code. So I met Brian Armstrong, as well as Soups and a lot of the folks at the early Coinbase team, from Risk Salon, which is, like, when a lot of the anti-fraud—Link

LubaI was the co-founder of the Risk Salon.Link

HaseebThat's right. That's right. That's a plug for you. I did not forget that at all.Link

LubaSo I'm taking all the credit for your entrance to crypto.Link

HaseebThat's right. It's all you. That makes it all you, in the end.Link

LubaYeah. Yeah. Yeah. It was all me all along.Link

HaseebYeah. Yeah, that's right. But after I quit Airbnb, I was actually not sure if I wanted to go into machine learning or into crypto. I knew I wanted to build a company, but I didn't know in what domain I was going to build this company. And I was weighing the pros and cons of, do I want to go into AI, do I want to go into crypto?Link

And what ended up weighing me towards crypto— I was very bullish on both of them. I was passionate about both of them. But what weighed me towards crypto was that I became convinced that AI really favored people who had traditional experience and credentials. So somebody who had, you know, a PhD, had been studying this for a long time. There's a lot of prior art. And of course, you know, I was an autodidact, you know, college liberal arts major. You know, I was not the kind of person who's advancing the vanguard of AI.Link

Whereas crypto, there were no experts in crypto back then. Crypto was a brand-new domain. Everybody was self-taught. There were no textbooks. There were no classes. There was no anything. You just had to go in there and figure it out. And it was all being invented in real time. And to me, I just thought, like, one, this is really exciting, but two, this is exactly the kind of thing that I'm good at, is going into a space of total uncertainty.Link

So I went into crypto, which was a space of total uncertainty. You know, nobody knew anything. There were no experts. There was no old guard. I mean, in retrospect, I can say that now. At the time, it felt like there was an old guard. It felt like, oh, there's people who have been here since 2013, 2012, 2011. There's, you know, the true OGs. I'm a brand-new baby. I'm coming in here when everything's hot. You know, the ICO bubble was on. Everybody was excited about crypto. And I was like, oh man, I'm just, like, a clout chaser. You know, I felt like I was coming in late.Link

And of course, people always feel like they're late, no matter how early they end up being to anything. I remember a story about Marc Andreessen, when he arrived in Silicon Valley, I think in '99. And he said that he was worried that when he arrived in Silicon Valley in '99, it was basically already all over, that the internet boom was pretty much done and there was nothing more for him to add. So people have always felt that way since the very beginning. But it turned out, I think I made a good call about coming into crypto. I mean, I don't know. We'll see. Maybe I would have done well in AI. I have no idea. But yeah, we'll see how it all plays out.Link

LubaHas Marc Andreessen influenced you in any way, as a technologist or investor?Link

HaseebHas he influenced me? I mean, I certainly admire him for his prescience in, obviously, everything that he's done within just traditional tech investing, and then him being the first big— I have. I've met him twice, I think.Link

I don't know that he remembers or that it registers for him, but obviously he's a legend in the industry, being the founder of Netscape and the founder of a16z, which kind of invented modern venture capital. But I'd say, yeah, he's somebody who I admire. Although I wouldn't say I necessarily want to emulate him.Link

LubaWhat about how he is in the world you don't want to emulate?Link

HaseebI wasn't thinking in particular about how he is in the world. I think it's more that the path that he took is very different from my path, right? It's like, I mean, I think this is true for almost everyone, is that I am just such a weird character. Like, I've come from such a weird background. I've taken such a weird path to where I am that I'm not really going to be able to look at anyone else's blueprint and say, great, if I just do what they did, I'm going to be successful. I don't think that's really true, right?Link

Marc Andreessen was, you know, the founder of Netscape, a very successful investor, built a16z in a very different environment, when, you know, the venture capitalists that he was competing against were just total old-school, very different, you know, types of investors. I've listened to a lot of podcasts and stuff where he's talked about how he built a16z and how he invested, but his formula is not a formula that would work today, because it's a different world, a different environment.Link

LubaI guess because you said that he's not someone that you want to emulate, or his path is not the path that you want to emulate—Link

HaseebYeah.Link

Luba—that maybe there is a path that you want to emulate. Is that true, or was that just a choice of words?Link

HaseebYeah, maybe it's a choice of words. I think in general I'm somebody who, I don't look to others for an answer of how I should do what I do. I think there are lessons that I can incorporate, but those lessons are pretty bounded in that time, that place, that situation, that circumstance. But for the most part, I've always assumed that I'm going to need to reinvent a blueprint that's going to work for myself, and that I need to think from first principles how I'm going to win in this domain. So trying to build the next a16z is not how you build the next a16z. You build it by responding to the moment and the different environment in which you find yourself, compared to when a16z first started.Link

LubaIs emulating someone or not similar to having role models, or are those two things completely different?Link

HaseebThey're related, but not exactly the same thing. I definitely wouldn't think of Marc Andreessen as a role model either. I think there are people who I really admire. Yeah. I really resist the language of role models, or of emulation generally as a concept. I think there are virtues that certain people embody that I respect, and that may even inspire me to want to embody those virtues. But the idea of a role model is, like, oh, you know, I want to be like Mike.Link

LubaYeah. Yeah.Link

HaseebThis person is, like, who I want to be, and I should find ways to get myself closer to who they are, and then maybe I will also be like them. I think that's usually a mistake, and it's usually not correct.Link

LubaYeah, I agree with that. I never resonated with the concept of role models either. It's just, you look up to certain people because you admire certain qualities. But the idea of a role model is almost like, oh wow, I love every single aspect of this person and I want to be them, which is very counter to finding your own path and being you and figuring out what that is. So I agree with that.Link

HaseebI mean, there are certain people for whom, like, they are genuinely really close to a certain type that resonates with this person, right? So if you're just like, look, my background is actually very similar to this person, they took this path, I'm going to take that path too. I don't think there's something wrong with that per se. But I think that kind of a strategy would be a total failure for someone like me, because there is nobody I can think of who has anywhere near as weird of a background as I— no, not, like, as weird, but weird in the same way.Link

LubaSo, speaking of taking paths, you left Airbnb and decided to dabble and then really dive into crypto.Link

HaseebYeah.Link

LubaStarted a company, joined Balaji with Earn, and then joined Metastable as an investor. Where did that transition of, like, hey, I'm going to play quote-unquote VC— because I think at that time you were kind of thinking about playing VC as a stepping stone—Link

HaseebYeah.Link

Luba—come from? Why did you decide to not give another shot to founding, but try this path instead? Like, was it Naval that really convinced you that that was it, or was it completely your own independent first-principles thinking?Link

HaseebYeah, so it was Naval. At the time when I first met Naval, I was working on a startup, and we actually had an M&A offer from one of the big crypto companies, and I was asking Naval—Link

LubaNot Coinbase?Link

HaseebCoinbase was one of the companies that was trying to acquire us.Link

LubaYeah. I guess it was Earn that was acquired by Coinbase.Link

HaseebEarn was acquired by Coinbase. I left Earn, started a startup. And that startup had acquisition offers, one of which was from Coinbase.Link

And so I initially met Naval to ask him for advice about how to navigate this potential M&A conversation. And he pitched me, oh, you don't want to join this company. I'm like, well, I kind of do. That's why I'm here. He's like, no, no, no, no. If you go get acquired by Coinbase, it's going to be super boring. You're gonna be run by your compliance department, right? Like, Coinbase is run by lawyers. It's going to be super boring. You should become an investor.Link

And I was like, I'm not an investor. I don't know how to invest. You know, I own index funds. Like, I'm not an investor kind of person. I don't know anything about finance. It doesn't matter. You don't need to know anything about finance. Like, investing, like, learning the mechanics of investing is actually easy. I can teach you the mechanics of investing. The hard part is judgment. Judgment is what's scarce, not investing knowledge.Link

And so he ended up convincing me to become an investor, and that's how I ended up shelving my startup and going onto the investing side. But I thought at the time that I'm not going to permanently be an investor. I thought, I'm gonna be an investor for a while, I'm going to make some money, but obviously investing is kind of cringe. Like, this is not the coolest thing you could be doing. The real thing, like, the actual thing that matters, is, like, building companies. So obviously I'm going to do this, hang out, and I'm going to go build another company. And little did I know that the place where I ended up building a company was actually in venture.Link

LubaIs investing still kind of cringe?Link

HaseebYes, it is absolutely kind of cringe.Link

LubaWhy?Link

HaseebI mean, it's also really fucking interesting and super cool, but it's definitely kind of cringe.Link

LubaWhat makes it cringe?Link

HaseebWhat makes it cringe? I mean, it is the quintessential genteel career, right? So it's like, I mean, we don't do this. I mean, this is part of, like, my whole kind of, you know, the way that we run Dragonfly. But, like, VCs traditionally, like, they take the summers off. They, like, don't respond to things on weekends. They take vacations all the time. It's, like, a kind of cushy job that you do after you've had, like, a long career and you retired and you're just, like, a great elder statesman of the industry. It's like, great, you know, I'll be a VC and I'll give advice to people, and that'll be my kind of fake job.Link

That's how a lot of people think about VC. That's how a lot of VCs actually operate. And I do not operate that way. Like, just constitutionally, I cannot do that. Like, when I play, I play to win. And if I'm not playing to win, I don't want to play.Link

LubaBut you can still be playing to win while, I guess, giving advice to people.Link

HaseebYeah, you can give advice to people. I'm not arguing about giving advice to people. It's more just, like, are you treating VC as, like, a part-time job slash, you know, high-status vacation? And a lot of people do.Link

LubaBut I feel like it's so hard to do that right now, given how competitive the deals in VC are. There's so many VCs.Link

HaseebOf course. That's why so few VCs are competitive.Link

LubaWhat do you think the rest of them are doing? How can you make it monetarily as a VC if you don't play to win?Link

HaseebWell, a lot of people— okay, so it's important to understand maybe some of the economics of VC. So first and foremost, there's a lot of VC funds that are smaller funds. If you raise $50 million, right, $50 million, let's say you charge a 2% management fee. Okay, that's normally what is typical for most funds. So if you have $50 million, a 2% management fee, that's a million dollars a year that you're making.Link

Now, it's a million dollars a year not just for your salary. It's a million dollars a year for all the salaries that you're paying, as well as any other expenses that aren't covered by your fund expenses. So you hire, you know, a CFO, hire somebody to deal with, you know, whatever, investing operations, whatever it is. Maybe that leaves you 500K a year that you're making, okay, as your take-home.Link

So, three-person fund, $50 million fund. That's not a big fund. That's, like, a small fund. There's a lot of people who can raise $50 million, hire two people, take 500K take-home. That's a pretty good salary for anybody. And you're coasting. You know, you don't have to be super competitive. You don't have to, like, win every single deal.Link

LubaAnd then most likely you're co-investing in deals. You're not leading deals.Link

HaseebYeah. You're not leading. Like, at that size, you don't have to compete with everybody for allocation. And, like, you're getting some stuff. You know, like, you're getting boxed out of most of the hot deals, but of course, they're hot deals. That's why they're hot. Like, yeah, of course Khosla's gonna win it, or Sequoia is going to win it, a16z is gonna win it. No skin off my nose. I'm not a16z.Link

And then it's even true for a lot of partners at these big firms. You go to, like, you know, Menlo Ventures, right? It's, like, a good firm. You go to NEA, it's a good firm. There's a lot of partners at these firms that, like, they take the summers off. They don't work weekends. They just, you know, yeah, they're like, you know, they've had a career, they've done stuff.Link

And it's not that everybody has to do those things. Obviously there's a value to having a relaxed job. If you're in a different phase of your career, you're not looking to kill yourself or to be super, super competitive. That's, of course, a very reasonable thing to want at that stage in your life. I'm not at that stage in my life, and I'm not that kind of an operator. I am very, very competitive in the things that I believe in and want to do well.Link

So for me, the way that I operate, I don't play VC that way. The people at Dragonfly don't play VC that way. If they do, this is the wrong place for them. So that's the way that I've built this firm. And that's why, although VC is cringe, I don't think the way that we do VC is cringe. But from the outside, you don't really know the difference.Link

LubaDo you remember the moment when you felt like, oh wow, VC is actually it, I don't want to go back to starting a company?Link

HaseebI don't know that there was a moment, but I certainly changed my mind over time, as I came to realize that startups are not very glamorous. Like—Link

LubaBut you were just saying how the way you like doing VC is not very glamorous either.Link

HaseebThat's true. It's not really about glamour. Yeah. No, no, I'm not saying that I want glamour, but it's more that, like, being a founder is such a thankless, brutal job, especially in crypto. It's even harder than I think it is in most other domains. And being an investor is actually unfailingly interesting. There's a lot of bullshit that goes into being an investor, but being an investor is actually the best way to try to understand the world and have a view about where the world is going, and be proven right or wrong based on the investments that you choose. In a way, there's no purer form of expressing your views about the future than through investing. And I don't think I really appreciated that before I had some rounds under my belt as an investor.Link

And then after I left Metastable and, you know, ended up building out Dragonfly, the thing that I realized most of all was that I really wanted to prove that I was good at it, because the time that I spent at Metastable wasn't long enough to prove anything.Link

LubaHow long was it at Metastable?Link

HaseebIt was a little bit over a year that I was at Metastable. And—Link

LubaAnd whom did you want to prove it to? To yourself, to Naval, to the world?Link

HaseebNot Naval. Naval actually believed in me. Which was atypical. But—Link

LubaOf Naval, or atypical of people believing in you?Link

HaseebAtypical of people believing in me. I feel like the throughline in my life has been that I believe in myself way more than other people believed in me.Link

So, like, you know, I mean, you can imagine that, you know, being a poker player, you know, I learned by myself, nobody taught me, and, like, I kind of rose the ranks very quickly. And I always believed that I could. And who, you know, who's going to believe, like, some random kid is going to be able to become a top-ranked professional poker player? And then I went from that to, like, okay, now I'm going to go learn how to code. And naturally, people don't believe that you can just learn how to code. Like, no, you didn't study computer science, you didn't go to a top university, you didn't work an internship, you didn't do any of those things. Like, no, I just learned it.Link

LubaDo you think that was kind of selective vision on your part, that you were more willing to see people who didn't believe in you than people who believed in you? Because I think if it's your story that, hey, you're always an underdog, and I'm always—Link

HaseebOkay. I think this is your story, that you think that I think this about myself.Link

LubaNo, I don't know, because I'm just thinking that when I decided to take a leap to learn how to code also— I mean, I was a little younger than you.Link

HaseebSure. Yeah.Link

LubaBut—Link

HaseebYou were in college.Link

LubaYeah, I was in college, but I was studying chemical engineering. Like, I still—Link

HaseebSure, you could make— you were studying at Waterloo, surrounded by all these people who are applying to coding.Link

LubaI wasn't, like, a former poker player, but I think it was still, at the time, pretty unconventional. Right now it's very conventional to, you know, teach yourself how to code, go into tech with whichever degree you might have, which is amazing. But at the time it wasn't as common. But I had a lot of belief in myself that, hey, I can do this, and I can prove to myself and to the world that I can get a job in Silicon Valley.Link

But I also do feel there were definitely people who didn't believe that would be possible. But I very much remember there were a lot of people who very much believed in me. And I saw both of them. Yeah. And for some reason I'm like, there must have been people who believed in you too. Like—Link

HaseebThere were a few. I would say maybe, like, two or three people I can think of that believed that I would be able to pull that off. But I didn't fully believe it at the time that I came out to Silicon Valley, because I just didn't know. I didn't know how difficult it was. I just didn't know this world. I'd read about it, you know, I'd seen TV shows about what Silicon Valley was like, but I never actually had any concrete experience with any of it. And so, you know, when I first came to Silicon Valley, my goal was to get a job at Pivotal Labs.Link

LubaWow.Link

HaseebDo you know what Pivotal Labs is?Link

LubaOf course.Link

HaseebYeah.Link

LubaIt was kind of like Atomic Labs. It was one of the venture studios.Link

HaseebYeah. It was like a consultancy. It was like a tech consultancy. It was definitely cool at the time.Link

LubaEspecially in Canada. Pivotal Labs—Link

HaseebWas it? Okay. Yeah. All right. I mean, it's not like Google.Link

LubaYeah. It's not—Link

HaseebIt's not like Google or Airbnb. It's like getting on, you know, the varsity team.Link

LubaYeah.Link

HaseebYou know, it's like, that was my goal. I was like, if I can get to Pivotal Labs, I've made it. And, like, I wasn't even thinking about Google or Airbnb, because I was like, obviously there's no fucking way. I'm not tracked. Didn't go to a great university. I'm just learning how to program for the first time. Like, they would never hire somebody like me, you know? And I just didn't know. I had no idea what was possible, what was not possible, when I first came to Silicon Valley.Link

So the idea that, like, people believed in me— I mean, people believed I was smart. But did people believe that I was going to be able to get a job at a top tech company? No. I can't think of a single person who thought that I was going to get a job at a top tech company when I came out to Silicon Valley.Link

LubaAnd so with investing, you needed to prove to, like, non-believers and to yourself that you could be good at it.Link

HaseebYeah. Well, not just that. Like, I wanted to prove to myself that I was good at it. You know, when I was at Metastable, I came into Metastable as a GP, but there were other GPs who had founded the fund. And I was very frustrated that they weren't listening to me. I was advocating for them to make decisions that they decided not to do. Those decisions turned out to be correct. Almost every single thing that I advocated turned out to have been a good call. But they just weren't willing to do it. And, you know, I interpreted that as, they don't trust me. They don't believe that I can do it. They don't believe that I'm right. They don't believe that my judgment is good.Link

Then after I left Metastable, I started looking at some of these other firms that already existed within crypto. You know, I talked to Paradigm, I talked to Polychain, and I wanted to come in as a partner. And these firms, either they weren't interested in having me join as a partner, or they were like, well, you know, maybe you can work your way up to partner, like, I don't know if you've really done that much. And I was like, fuck you guys. You guys don't believe that I can do this.Link

So, I mean, to be clear, I had very little proof that I was anything, you know? Like, I didn't have a big brand, didn't have, you know, all these years of investments under my belt. I was a relatively new entrant into crypto. I had just learned about it in the last year. So there were all sorts of reasons for them to have that reaction to me, which is, why would I believe that you can do this? What evidence do you have that you can do this?Link

But I believed, like, of course I can do it. How could you not know that I'm fucking amazing? I'm the man. Of course I can do it. If I decide I'm going to do it, I'm going to fucking do it. And so that delta between what I believed about myself and what other people believed about me, I can't remember a time that wasn't there.Link

LubaSo were you intentionally looking for a position where you could really prove this to the world, to others, to yourself, in a position of power? Or were you seriously considering joining other firms at a lower-level position?Link

HaseebI was totally considering it. And I was open to it if I felt like there was really room for me to quickly prove myself. But at the end of the day, I ended up deciding to partner up with the guys at Dragonfly.Link

LubaWhat's the story? How did that happen?Link

HaseebSo, what happened was, so I knew the original team. So the original team was two guys, Bo and Alex, who originally ran Dragonfly. And I knew Bo and Alex because they were big investors into Metastable. And I first met them— I first met Alex through Naval, because he had also worked with Naval at AngelList.Link

So I got to know Alex, and when he knew that I left Metastable, him and Bo immediately tried to recruit me. And there were a number of firms that were interested in me. They were not the firms that I was interested in, but they were interested in me, and they wanted to bring me on as a partner. They were mostly pretty small. And the thing that I came to appreciate about Dragonfly— initially I was like, yeah, no way, I'm not joining this firm. Because I was like, you know, who are these guys? They're no-names, you know—Link

LubaDon't you know who I am?Link

HaseebYeah, exactly. I'm Haseeb. I'm fucking amazing. But they were very insistent on wanting me to join. But the thing that I realized more than anything, especially through my relationship with Bo, was that Bo, more than anybody I had met, absolutely trusted me. Almost immediately when Bo met me, he realized that, you are extremely ambitious, you want to win, you are really, really good, and you will stop at nothing until you get there. And Bo's feeling was that, I have the exact same ambition for what I want to build. And he immediately trusted me and told me, if you come join Dragonfly, I'm going to make you an equal partner.Link

LubaHow did he have that level of confidence? Did he work with you closely at Metastable? Does he just have really good Spidey senses? I mean, you've worked with Bo for quite some time now.Link

HaseebBo, I think it all just comes down to judgment. Bo has been a VC for a very, very long time. Very, very intuitive. He's very different than me. I'm a very analytical, very kind of, you know, calculating person. Bo is the complete opposite. Bo is pure intuition, pure kind of social reading.Link

LubaAmazing host.Link

HaseebHe's an amazing host. He's one of the best, like, communicators and kind of socially skilled people I have met in my entire life. And he is amazing at things that I suck at, right? Obviously, I'm the guy who, like, fucking hates birthdays. So Bo is the consummate opposite of that. But then the things that Bo's bad at, like, he is not analytical, he's not rigorous, he's not calculating, I am extremely good at that, right? I'm obviously technical, and, you know, I can do the underwriting and a lot of this other stuff.Link

And so he immediately respected me for the things that I'm really good at, and I immediately respected him for the things that he's really good at. And that's one thing, I think, that makes for a really strong partnership, is not just that you respect each other, but that you are able to defer to each other in the domains in which each of you believe the other is excellent.Link

So when it comes to fundraising, relationships, you know, kind of the cultivation of people, Bo is world-class, and if we disagree, Bo's right. And when it comes to technical analysis and underwriting and this kind of stuff, when Bo and I disagree, he knows that I'm right and he defers to me. So that kind of trust and relationship, although the two of us are very different, very different generations, we immediately had a really, really powerful and stable trust in each other. And that's, I think, the reason why I decided that, okay, I can work with this guy.Link

LubaHaving had such a great partnership with Bo, what has it taught you to look for when you're looking at teams and co-founders? And what about people who are actually very similar but they decide to work together?Link

HaseebWell, there's nothing wrong necessarily with being similar. Being similar is totally fine. I think it's just a different kind of working style that you need to have with somebody like that. Like, I think it's okay— to be clear, it's more common to have a team that's similar than different.Link

When you are different, the important thing is that you actually trust each other in the domains in which you are each specialized. If you don't have that, if it's like, okay, this person's really good at this, but I don't actually trust them in that domain, or I'm going to try to override them in that domain, that's where being really different is fatal.Link

So I think a lot of what it comes down to, seeing how teams work together, is seeing their dynamic, seeing how they interact with each other, especially how they interact with each other in uncomfortable or difficult situations. Which is why very often, when I'm talking to a team and trying to size them up, I'll often try to put them in an uncomfortable situation.Link

So, you know, I will ask them— so let's say, you know, you're a founder and your co-founder is sitting over here. I'll say, so what are this person's responsibilities? And, you know, people very often will say, okay, well, let me hand it to him. No, no, I want you to explain what his responsibilities are. And then I want to see how he reacts to how you explain his responsibilities. And then I'll ask him, what are your responsibilities? Do you agree with that? Is there anything you left out? And just seeing how they react to that interplay.Link

Another thing that I'll ask often is, how are you splitting the equity? And, you know, very often it's something that people don't, like, talk about in front of each other, especially if it's unequal. If it's unequal, then I really want to hear about it. And so I'll ask, you know, how are you splitting the equity? And, you know, very often the answer is 50/50, but sometimes the answer is not 50/50. And then I'll ask, okay, why are you splitting it equally? Do you not think that one of you has a bigger contribution? And I'll see how they react to that question.Link

And, you know, like, getting in to see how strong is this relationship of trust between these two people. What do each of them think that the other one is good at? And how confident are they in each other and each other's answers? That is a lot of what I'm looking for in a team.Link

LubaHow can someone cultivate trust? Like, let's say they're just naturally a person who has trust issues.Link

HaseebIf you have trust issues, don't start a team. Like, that is not a good foundation. Like, maybe be a solo founder. But if you have trust issues, you are not going to be a good co-founder. So—Link

LubaSo you just generally believe that it's not possible to work through it, to really work on yourself, or whatever your bias might be, to be able to fully trust people?Link

HaseebI think a startup is not the place for you to work out your trust issues.Link

LubaBut let's say you're not starting a company yet. You know that this is something you need to work on.Link

HaseebFine. So, okay, I need to know more. Trust issues is a very broad category. What kind of trust issue are you imagining?Link

LubaLike, let's say you are very controlling. You don't trust that other people will do a good job, and as a result you start micromanaging, and you're like, oh, you know, I don't trust this person to complete the thing that we agreed they're going to be doing, so I'm just going to take over and be, yeah, really unknowing about it.Link

HaseebSo, okay. So all right, I will answer that in a more abstract way, which is trying to actually diagnose what that means, to say that I am a controlling person because I micromanage the people around me. It could be that that's actually correct. That's not a mistake. Because if you work with people who are unreliable and who you do need to micromanage in order to get the right outcome, then what you're describing is not a trust issue. What you're describing is a correct response to your environment, right?Link

So if you work with people who are, you know, let's say low-skilled labor, who are unreliable, who don't care about their jobs, then, look, that's the behavior you're going to get, right? Everybody's had the experience of working, like, you know, a job where the people don't want to be there. And if they don't want to be there, then they're not going to work very hard, and they're going to need to be micromanaged, right?Link

In a job where people do want to be there, and where people are really intrinsically motivated to do their jobs and do them well, that's when micromanaging is actually a mistake, right? People get micromanaged at McDonald's because if they don't, they're not going to work hard, because it's a shitty job. Nobody wants to be at McDonald's. But you don't need to get micromanaged when you are, you know, employee number one at a startup, because you want to be there. You are there at the frontier, building something really interesting.Link

So if somebody has the same reaction to, you know, dealing with somebody who doesn't want to be there as with somebody who does, then maybe the answer is that you are just miscalibrated about understanding the people around you. If the solution is to just have a deeper understanding of what is motivating this person and what makes them effective, then great, problem solved.Link

If the problem is your anxiety, if this is a way for you to solve the fact that you are anxious if you are not imposing this on other people, then that's a different story, and I don't think showing you something about the world is going to solve that problem for you, right? So if your problem is one of anxiety, go see a fucking therapist, you know? But if your problem is that I'm micromanaging people when I don't need to, then I can show you, aha, this is a mistake that you're making. And by learning the mistake, you can solve the problem.Link

LubaThat makes sense. I want to switch gears to meaning.Link

HaseebOkay.Link

LubaAnd ask you, like, now that you've proven to the world and people around you that you are indeed, I assume, a good investor— did you prove it to the world?Link

HaseebI think I'm on my way to proving that.Link

LubaOkay. So you're on your way to prove that you're a great investor. It's going to take time, obviously, to return the funds. Is that where you draw meaning right now? And the reason why I'm asking about meaning is because in your, especially in your early blog posts, because you were a lot more personal in your early, I guess, younger days—Link

HaseebYes.Link

Luba—than you've gotten, like, later with age, or with time, or with your career progression.Link

HaseebWhat are you trying to say?Link

LubaI'm not trying to say anything specific. It just got less personal. Less sharing of yourself online.Link

HaseebSounds like an accusation.Link

LubaSure. You can take it as an accusation. Let it be that. So, you talk a lot about meaning, and, you know, just kind of talking about, like, will I mean something in the world?Link

HaseebYeah.Link

LubaWhat meaning did you seek then, and how has it changed?Link

HaseebThen, being in my early 20s. Yeah. It's hard to fully place myself back into what it felt like in my 20s, but I think the thing that I wanted more than anything is greatness. And greatness in something. I don't think it was that I wanted to accomplish some particular thing, but it's more that I wanted to prove that the endowment that I am born with, the body, the mind, the experiences, the capabilities, are capable of greatness. Of being great at something. And I don't know what it is.Link

And that people— you know, I could tell people this, like, oh, I'm really smart and really capable and really hardworking, and, like, I could do all these things, I'm just choosing not to. That people wouldn't believe me, that they wouldn't buy it, that I haven't proven it, and that the burden of proof is on me to show that that is possible.Link

And that it in some way is my, like, moral obligation that if I have talent, if I have capabilities, to actually cultivate them and to do something with it. And that if I don't do that, I have squandered it. I feel that really deeply, or at least felt that very deeply at the time when I was young. If I wasn't very talented, if I didn't think that about myself, then I don't think I would have that desire.Link

LubaSo given that that is what you thought, is that something you continued to believe in, in that meaning for you personally is in achieving greatness at something?Link

HaseebI mean, yes, I think it's still true. Although I don't know that I would put it in those words today. I feel like that's a very adolescent way of describing where meaning comes from. But I think there's a kernel of it that's still true, which is that, I think now I resonate much more with thinking about it in terms of excellence and mastery and virtue. I don't think so much about greatness, because I think I realize that greatness is more about other people. Greatness is a relative term. Whereas, you know, excellence and mastery is more of an internal thing. You're not really great if nobody agrees that you're great. But you can be excellent. You can master a domain regardless of whether other people know that you have, or whether other people acknowledge that you have.Link

So I think as I've gotten older, that's more what resonates with me and what grounds my motivations. But there's always some desire to prove things to other people. I don't think that's ever going to go away for me. And it's not even real people. Very often it's imagined people. It's the people in your past. It's the eyes with which you see your old self. You want to prove to those eyes that, no, no, no, no, I was not this. I'm not this boy that you once saw me as. I was not this, you know, searching adolescent. I became someone. I did something with myself. I didn't waste what I was endowed with.Link

LubaDo you think it's wrong for people to seek validation from other people? Not from your past or future self, but really, really crave and desire that validation, for someone to say that, hey, you're capable, you're smart, you're worthy?Link

HaseebNo, I don't think that's wrong at all. I think it's mostly necessary for most people to have some degree of social validation. Like, we are social animals. It is extremely distressing to a human being, a Homo sapiens, to know that other people in the tribe do not think that you are worthy. Like, it's just, some part of our hindbrain is always tracking what the rest of the tribe thinks of us. And, you know, a huge part of our brain is dedicated just to understanding what other human beings think about us. So I think this is pretty intrinsic to how humans are wired. I don't think this is, like, oh, you're a bad person if you think about what other people think of you. I think that's simplistic, and even just kind of puritanical, to believe that that's wrong.Link

Now, is it healthy? It's a different question. There's some amount of that that's always going to be there, and you just have to come to terms with it. In the same way, like, look, you're always going to be hungry. You will never abolish hunger from your body. But you should not be driven by hunger. You should not let hunger be the primary motivation that drives you through life. We call that gluttony. That's how you become a morbidly obese person, if your primary motivation is hunger.Link

In the same way, proving yourself to others, or getting validation from other people, if that is your primary motivation, it becomes a disease, right? It becomes, you know, like gluttony. And so I think there's some amount of it that you will have. You shouldn't pretend that you don't care what other people think. But it should not be the primary way in which you orient yourself to your own motivations.Link

LubaAnd what shaped this belief for you? Was it—Link

HaseebWhich belief?Link

LubaLike, the belief that it's fine to have ego. Some amount of ego is healthy, and you should self-examine whether that is the only primary driver that you have, or whether it's coming from an unhealthy place and you need to kind of work on that, examine that, fix that. Is that something that you learned through your own journey? Was it shaped by your interest in Buddhism, or interest in other, maybe, philosophies, or stoicism?Link

HaseebYeah, I mean, it's an insight that flows through many different wisdom traditions, which is both self-acceptance and striving for virtue. So stoicism is much more about virtue ethics. I think there's a sense in a lot of stoicism that one should erase the focus on oneself, or how one is perceived by others. I think this is a very naive interpretation of stoicism. I think if you read, like, you know, Marcus Aurelius or some of the original Stoics, it's very clear that actually they do think it's important how you are perceived in your social standing. Because a human being is a member of a society as well as an individual. And as well as any sort of interior life, you have the exterior of your life, and they're both part of your responsibility as a good citizen.Link

I think that's correct. How you are perceived by others is not the only thing that matters. Sometimes the world is genuinely wrong. Sometimes the crowd is genuinely wrong, and the right thing to do is to go against the crowd and to give them the middle finger. But there are times when that goes too far, and too much of your sense of self is being derived from other people. Or, sorry, there are times when you can be too self-effacing, or too much not considering the fact that you live in a society and your relationships with other people are deeply important, from the ways in which you might hurt them unnecessarily without getting anything out on the other side.Link

So you can go too far in either direction. But I think the traditions of wisdom that I most resonate with are ones that are more realistic, right? So the realism is that, hey, it's not good to derive your entire sense of self from how others perceive you, but it's also not good to pretend that you don't. It's not good to totally put your sense of self in how other people perceive you, but it's also a mistake to have zero of it come from how other people perceive you.Link

LubaAnd how do you derive meaning and purpose now?Link

HaseebHow do I derive meaning and purpose now? How do I derive meaning and purpose now? It's a very difficult question to answer when you frame it that way, because, you know, it's kind of like asking, like, you know, how do you keep your lungs breathing? And the answer is, like, I don't know.Link

LubaWhat gives you purpose and meaning now?Link

HaseebI mean, my answer is the same. Yeah, the same question. Which is that I have purpose and meaning, and it's one of these things that, like, you notice when your lungs stop working. But can you really explain, like, what your lungs are doing to continue breathing? It's like, no, I'm just breathing. Like, it's intrinsic to who I am and what I'm doing. In the same way, like, you know, what gives me meaning and purpose? Like, well, you know, every morning I do jumping jacks, and that's what gives me the meaning and purpose. It's like, no, everything about what I'm doing comprises the meaning and purpose.Link

LubaYeah. I wanted to say, about the ego thing, that you and I had this conversation very recently, where I feel like we live in a world right now where having any amount of ego is, like, bad, and everyone needs to get rid of ego and be completely, yeah, completely egoless, for lack of a better word, and really try to tap into who they are at the core. But you are right that we are social creatures. So you kind of do realize who you are through the mirror of others.Link

And sometimes you need to have conviction to prove others wrong, or to take your own path and give yourself a different grading than people around you give you. But I've come to, I guess, more of an acceptance and conclusion that, hey, this whole idea of examining your ego and trying to get rid of it at all costs is kind of the wrong idea. Because, to what you said, it's like going just down one of the extremes, where the opposite extreme is being incredibly egotistical. And life needs to be balanced, and the truth is somewhere in the middle.Link

HaseebIt's also about the question of, do you respect the society in which you find yourself? Because there are genuinely societies in which you should say fuck you to everyone, right? There are people who are born into dysfunctional families, who are born into countries where they don't identify with the culture, but they identify with a different global culture that they might find themselves in contact with. And I'd say I wouldn't want to spurn somebody who does that. I think there are times and places when the right answer is to say, yeah, you live in a society, but your society sucks, and fuck that society. There are groups— not all human groups are great, obviously.Link

But if you respect the society that you're in, then I think you should have some amount of deference to— as you put it, society is a mirror. It shows you some aspect of who you are. It's not necessarily, okay, well, everyone tells you that you're X, that doesn't mean that you're X. But they're showing you something about yourself by the way that they react and engage with you.Link

LubaKind of similar to meaning, I have this quote from one of your early blogs.Link

HaseebOh shit. Okay.Link

LubaThat says, "Wonder if the book I write is going to be worth anything." And that was your poker book that you were thinking of writing. "Wonder how people will remember me when I die. Wonder why I am so desperate to mean something." Very deep and soul-piercing. But I guess that was the search of the adolescent.Link

HaseebYes.Link

LubaThe adolescent search for meaning. But I'm curious, how do you think about legacy these days? Like, is that as big of a deal as it was in your early 20s?Link

HaseebIt's not.Link

LubaIt's not?Link

HaseebIt's not. I think legacy— I mean, I don't know, different people feel differently, but I care a lot less about legacy, you know, now. I cared a lot when I was in my early 20s. I think, you know, when I was in my early 20s, after I wrote the book that I ended up writing, which was the book called *The Philosophy of Poker*, after that I wanted to write another book. And I thought that book was going to be, like, my memoir. So, like, the book about my life, how I became who I am, and all this other stuff. Like, this is my life, witness me.Link

And now I'm like, God, kill me if I ever write a fucking memoir. And it's ironic, because I've done way more stuff now than I had at the time that I was, you know, saying all this stuff. But I realize now how incredibly unimportant it is to me to be witnessed. Like, obviously, and it's not like— that doesn't mean that I want to lose contact with the world, or that I don't want to be in conversation with the world. But to have people say, look at me and my legacy, look at all the great things that I did, wail for me when I'm gone— I want the people I care about to care about me when I'm gone. I don't really care if other people do. It just doesn't matter.Link

LubaWhen did that change?Link

HaseebIt's hard to pinpoint, but I think just as I've gotten older and more, I think, honestly, more self-confident and more relaxed in who I am and in what I believe I can do. I think when you don't know whether or not you can accomplish anything in your life, you're desperate to want people to believe that you can. And that's, you know, the desire to etch your name into the wall of history comes from that. Now I'm pretty confident that, I mean, it's not that I can do anything I want, but I'm pretty confident in my own abilities and my own determination to do things if I set my mind to them. And I don't feel the need to have to prove that to other people.Link

LubaBut I think you care about the legacy of Dragonfly? Or do you completely separate the two?Link

HaseebI do to some extent. Like, I don't know that I care about the legacy of Dragonfly. I care about Dragonfly. The legacy of Dragonfly is, like, what happens after Dragonfly is gone. I don't know that I care about the legacy of Dragonfly. I care about Dragonfly while it's here. I want it to be successful. I want it to be revered. I want it to be helpful to the people who work with it. I want everybody who works with Dragonfly to say, Dragonfly is fucking amazing. They're the best VC in this industry. These are the people I always want to be working with.Link

When Dragonfly's gone, when crypto's over, when I'm dead, who gives a fuck what people say? If anyone remembers Dragonfly, doesn't matter. There's so many businesses in the history of the world that nobody will ever speak of or dream of ever again. And that's okay. They don't need to.Link

LubaWhy do some people care so much about legacy? Is it completely, like, is it being more on the barbell of ego?Link

HaseebIt's definitely a kind of ego. Why do they care so much about legacy? I mean, who knows? Maybe I'll care about legacy when I'm, like, 70 or something. I mean, that certainly seems to be when people start fixating on these kinds of things.Link

LubaOr maybe you'll start caring about legacy when you start having kids.Link

HaseebMaybe. I mean, that's very different, right? If legacy is literally your kids, I think it's just caring about your kids, you know? Like, caring about legacy is, like, I want people to remember that I was here, and I want them to say my name after I'm dead, right? So there's, like, I think, what is it, like, Andy Warhol? They said, like, you know, everybody dies twice.Link

LubaOne time when your body dies, the second time, the last time someone says your name.Link

HaseebYeah. Yeah. And I don't know that I care that much whether or not people say my name after I'm dead. I want to have an impact while I'm alive. That's the thing that matters to me much, much more than the impact after I'm dead.Link

LubaOne of the questions that I had was about your writing, and the fact that it was, like, really, really personal, and how you said it was for people to witness you and your experience and your emotions. And with time, it's gotten a lot less personal, at least on your blog. And I think on Twitter, you don't really share a lot of personal things outside of personal opinions on topics and ideas.Link

HaseebPersonal opinions are personal.Link

LubaYeah, sure. It's not, you know, personal opinions. Emotional explorations, like, hey guys, I know I haven't written here a lot, but—Link

HaseebYeah. Okay. All right. All right.Link

Luba—I've been agonizing about my future and whether I'm going to mean something. Like, it was very deep.Link

HaseebTrue. True.Link

LubaAnd is it related to the fact that you just don't care about this, like, people witnessing you, and legacy? Or was the transition from this personal dialogue with your 100-people audience, that then grew, just kind of naturally evolved because you grew older?Link

HaseebIt's a few things at the same time. So one of it is definitely that it's just, like, me getting older. And, like, you know, a lot of people kept a LiveJournal when they were in their teenage years, and then eventually, like, okay, you know, I'm good, I don't need to do this anymore.Link

A part of it is also just that there's less going on, right? Like, the emotional turmoil that one experiences in these liminal phases in one's life just is a lot more interesting to write about, and there's a lot more to process than there is for me to process right now.Link

There's also just, the stakes are higher, right? So if I'm writing about, like, oh, you know, I'm thinking about firing this person, I don't know what to do. Like, okay, everybody at my company reads my blog. You know, they're going to be like, oh, who's he thinking about firing? So, like, there's a lot of things like that, that obviously once your life circumstances change— like, when you're just, you know, a rank-and-file engineer, who cares, you know? It's like, oh, I'm worried about my career. Am I ever going to run—Link

LubaYeah. Yeah, but you had that transition a lot earlier, before you started running Dragonfly.Link

HaseebYeah. True, true, true. I mean, obviously my post about my salary was very piercing. Obviously that's why people got so upset about it. Thought I was a douche, apparently.Link

But the other thing I will say is that the other part of it is that I think I just feel a lot more secure than I did at the time. And a lot of it comes from just having a much stronger sense of self, that I don't feel the need for those hundred people, or thousand people, or 10,000 people to validate me, to see me, to, like, notice, like, oh wow, this person out there is struggling and going through these things. And, you know, one feels an enormous amount of solidarity when you write something, put it out in the world, and have other people witness it. I think I really needed that at that time in my life. And although I still go through hard things, I don't think I need it.Link

LubaOn the point about being secure, it was really fun for me to read your tweet that went super viral the other week, about advice to 20-something-year-old men on, I guess, how to make the best out of your 20s, how to be a man in your 20s.Link

HaseebYep.Link

LubaSince when are you, you know, giving advice about how to be a man?Link

HaseebI continually give advice, but there— I mean, there was some viral tweet about people giving advice to your 20s. Yeah, it was like, oh, men in their 30s, give advice to men in their 20s. And I don't usually do that kind of stuff, but I—Link

LubaWhat inspired you to give advice?Link

HaseebI don't know. I just was imagining myself in my 20s.Link

LubaSo, in your 20s— the other reason why I bring it up, you write a lot about becoming the man you want to be, and about manhood. So, yeah, who has shaped your idea of what it means to be a man? When did you come into your manhood? When did you feel like a man? And tell me more about this advice that you have for 20-year-olds, and maybe 30-year-olds too.Link

HaseebWhen did I become a man?Link

LubaI don't know. Maybe.Link

HaseebDamn. That's tough. Growing up, I felt like I didn't really have a very coherent picture of the kind of man I wanted to be. I saw the kind of man my dad was. I saw the kind of man that, you know, I saw in the world around me as I was growing up. And none of them seemed like the kind of person I wanted to be. And that for me was very, maybe just confusing, about how the goals that I had, of what I wanted to do in the world, aligned with my sense of manhood.Link

You know, I think a lot of the, you know, things like being very focused on school is not very manly. I was very interested, when I was going to school, I was studying philosophy, and also something not very manly. Ended up becoming a poker player, which I guess is kind of masculine, but, like, not, you know, like, I'm building, you know, brick-and-mortar things with my hands.Link

And the sense— I mean, because I think also poker was such an isolating game, like, as a profession. Because although you're playing with other people at a poker table, you're really on your own, in the sense that you're the only one in your corner. Nobody else is rooting for you. Everybody else wants you to lose. It's not a team sport. And so you really are you against the world.Link

And I think manhood comes in very large part from responsibility. It comes from being able to shoulder things for other people and stepping up to the plate. And I think it's actually very hard to cultivate that from something that is so individualistic, like poker. So my ideas of manhood, where do they come from? I mean, they came from all the different images and people and, you know, places that I've been. But the thing that I realized that resonates for me most with masculinity is strength and responsibility. So if you are strong and you can be responsible for other people, that's what makes you a man.Link

LubaI feel like in the modern world, and it's not that I feel like, it's kind of facts, people take on less, or are willing to take on less and less responsibility. And there is more and more desire to have your life be incredibly frictionless. And that comes with apps that we use, with services that we use, with interactions that we have with other people. Because of how the world is shaped in terms of consumption, we expect very little friction in our day-to-day interactions with people.Link

And as a result, the common complaint for men is that men are not able to take responsibility. I mean, coming from the world where I was building a company in dating, that is a huge complaint for women, that they don't feel like they're, you know, in traditional terms, safe, protected by a man who can make decisions and take responsibility for her, for others, for decisions in his life, for even, like, finding his own path and purpose. Do you see that at all, through your own, like, evolution through life, just men that you interact with, what's happening in society broadly? Is that what inspired you to write the post with advice to young men?Link

HaseebThat is particularly what inspired me. But I'm very aware that, like, society on the whole has become more feminized over the last 30 years. And, I mean, many people have observed this, is that just, you know, beauty standards for men have become more feminized. Like, there's fewer signals of kind of uniquely masculine traits. Like, the kind of people who you see as movie stars are, you know, if you just look 30, 40 years ago, they had more traditionally masculine traits and more traditional masculine builds.Link

And it's obviously true that you see more and more institutions becoming more feminized, right? And so this is one thing that Tyler Cowen has written about very convincingly, is that academia in particular has become much more feminized. Where it used to be that, you know, maybe there's gender parity between male and female teachers. Now the majority of people who work in academia are female. And, you know, for boys that are in schooling, they are basically taught to repress their masculine instincts, which is mostly about, you know, being disruptive, energetic, physical-type stuff, and to instead conform to what most of the girls are doing, which is more verbal, social, and quiet and studious.Link

And all of this stuff results in a society where we see increasingly disparate outcomes earlier on in life between men and women, where actually women are doing better in school, in health, in getting jobs, in kind of being functional members of society, than men are. And this is in large part because society has started to shift to become more women-friendly. In large part, rationally, welcoming more women entering the workforce and entering into more and more parts of society. But that has also led to a world that is less accepting of masculinity, or not accepting, but sort of less encouraging of masculinity and masculine traits.Link

So I think in this world, especially in the advent of things like MeToo and, you know, wokeness and all this other stuff, a lot of men and boys increasingly feel like masculinity is somehow something to be hidden. Where it's somehow something that's, not a moral failing, but maybe just, you know, kind of passé, maybe not the dominant way that people ought to be behaving in today's society in order to be successful, in order to be liked, in order to be respected, in order to be accepted.Link

And as a result, I think that leads to a lot of confusion among young men about how they're supposed to behave, what is supposed to be modeled for them. Are they just supposed to remove the thing about them that makes them men, and to try to conform more to this kind of androgynous, homogenized view of what society is supposed to be rewarding? No. I think this is obviously doing a disservice to men.Link

And that's, you know, there's a lot of movement now of trying to come up with positive messages and role models for men, to try to more pro-socially masculinize young men. I resonate with that story. I think it's right. I see it playing out the same way that many other commentators have. And that was part of the spirit under which I wrote that tweet. Is, what are the messages— when I was young and I felt like I didn't have a clear picture of what kind of a man I wanted to be, that was actually going to be rewarded and resonate in the society— what would have been most useful for me to hear when I was 21?Link

LubaSo given that the society is already shaped in a way where it's more, as you said, women-friendly, and as a result, not just women-friendly, but it almost undermines the traits of natural masculinity, what should we do as a society to change that, outside of positive messages? Cause positive messages is one, but it requires a certain amount of conviction that, hey, I'm just going to go against the grain and I'm going to follow this, like, more masculine path to find my purpose, and to be responsible for people, be more traditionally, like, a man. But it's not being welcomed or invited by the broader society.Link

HaseebI don't know. I do not consider myself to be a very good social planner. I think I have a lot more clarity about what to do as an individual than I have on how to reorganize society. I don't think anybody really knows what is the right way to reorganize society around trends that seem to be happening pretty much everywhere in the world. Like, as an individual, you know, as a young man, or as somebody who has the ability to influence young men, I have a lot more clarity about, okay, what can I do? What can you do? What can different people do? Like, the individual is the locus of impact.Link

As a society, I think a lot of these things, like, you can't really put the genie back in the bottle, right? Like, the degree to which institutions have changed, the degree to which the nuclear family has changed, the degree to which dating has changed, they're not going to unchange. You can't really rewind history in that way. Like, you know, things like family size, or divorce rates, or, you know, all these different things, right? Video games, porn. We are not going to undo these. These are now part of the furniture of society. So you can rearrange yourself on the furniture. You can decide what furniture to spend more time on and less time on, but you can't really delete any of the furniture. It's just there.Link

LubaSo being a man means taking responsibility and being strong, right?Link

HaseebMhm.Link

LubaFrom your blog in the early days—Link

HaseebDo I contradict myself?Link

LubaYeah— no, no, no. Actually, not. "My choice is not between happiness and unhappiness, but between strength and weakness. To value strength above all else, body, mind, spirit, this is the path to being a man." So, very much resonating with what you're saying now. Persistence. Yes. But does this specific excerpt resonate with you still?Link

HaseebIt does. That's a really good line. Yeah. Yeah. I completely agree with that. And I recognize that very much as being the way that I felt when I was in my early 20s, which is that I knew that I was not strong. I knew that I was not somebody that both— I knew I was not somebody who I respected, and I was not somebody who was strong enough to be able to take care of other people. And I think now I am. And that's part of the reason why I feel much more secure in myself as a man.Link

But you have to, you know, when you're that young, you don't really know, right? I mean, I knew enough to know that I wasn't. But I think most people, like, you can't really know, because, you know, very few people at 21 actually have enough responsibility to be able to answer that question in reality.Link

LubaHas your definition of strength changed over the years?Link

HaseebNo.Link

LubaNo. Same thing.Link

HaseebSame thing.Link

LubaDo you then think that for men it's strength and responsibility, but for women it's happiness? Or, I mean, I know you can also say that you're not qualified to give your opinion.Link

HaseebI'm not an expert on femininity, so I don't think it's my place to opine.Link

LubaWhat is your relationship to masculinity now?Link

HaseebWhat is my relationship to masculinity now? That's a very interesting way to phrase that question. What is my relationship to masculinity now? It's something that, when you're young, you fret about much more, because you don't know if you have earned your comfort with yourself. I feel now, much more so than I did at that time, that I have earned my comfort with myself. And the only person that you can get that comfort from is you.Link

So you know what your own— or maybe you don't know what your own standards are. Actually, I think probably at 21 you have no idea what would make you satisfied that you are yourself the kind of man you want to be. It's one of these things, like, you know it when you see it. I think I am now somebody who, I'm very secure in who I am, in my masculinity, and, as I mentioned, in my sense of self. I don't feel like I have anything to prove to anyone. I mean, I have some things I want to prove, but nothing that I need to prove.Link

LubaSo if I'm, say, a man, and I'm 22 or 23, and I have this restless sense of trying to figure out my purpose in life and what kind of man I want to be, what are the things that I should be doing?Link

HaseebI mean, first thing, you have to define what that means for yourself.Link

LubaHow do you define that for yourself? Cause, you know, right now there is also a bunch of outsourcing of thinking generally. You know, it's going to be even more prevalent with AI. How does one learn the skill of thinking for themselves?Link

HaseebI think it's actually very rare to outsource your thinking. I think most people who are reading, listening to podcasts, watching, you know, their favorite person on YouTube, or they're, you know, whatever it is—Link

LubaListen—Link

HaseebWhat's that?Link

LubaOr listening to The Luba Show, you know.Link

HaseebOr listening to The Luba Show. I don't think that means they're not thinking for themselves. Like, other people who you believe are wise and have something useful to tell you should be an input into your understanding and the way that you think. So if you are just completely accepting the views and perspectives from somebody and just importing them directly, you know, kind of like a raw file format, directly into your brain and into your worldview, that means you're not thinking for yourself. But I think that's actually pretty rare. I think most people do think for themselves. Although, you know, I'm very happy to criticize other people.Link

So I think a lot of it, the answer is, like, look, you should listen to other people. You should observe many different men, many different women, many different people. See what you admire, what you detest, what you find to be phony, what you find to be authentic, and try to think about what it would look like to model all of the traits in yourself. They won't necessarily look the same as they will for somebody else. But, like, to really seriously engage with that, like, what would the version of Luba do? What would she be if she were the person I most admire? Becoming that yourself, becoming the person that you most admire, is what it means to consummate your masculinity, in my mind. Or femininity.Link

LubaYeah. On that note, it kind of links to your point in the earlier days about the pursuit of greatness. In some ways, it's like the pursuit of the great version of yourself that you want to become. How much of life should be full of enjoyment, versus enjoyment being secondary to that pursuit of greatness?Link

HaseebI think enjoyment— well, how much should life be about enjoyment versus the pursuit of greatness? I don't think there's a single answer to that.Link

LubaWell, again, in your earlier writing, it was all about, hey, enjoyment is very second-order. I'm not really pursuing enjoyment here. I just want to be the best version of myself and I want to be great. Has that changed? Are there—Link

HaseebIt hasn't changed for me. Is it the right answer for everybody? I don't think enjoyment versus greatness is the right dichotomy. I think the way that I would frame it is flourishing. So the Greeks called it— not just progress. So the Greeks called it eudaimonia, which kind of literally translates to flourishing, like a plant flourishing.Link

And I think flourishing doesn't necessarily mean, oh, okay, my bank account is flourishing, or, like, oh, my skill set is flourishing. It means flourishing in some fuller, deeper sense that, again, you know it when you see it. It may involve a feeling of happiness, but it's not the same thing as just, oh, you should be happy. Because the person who is happy is not necessarily the version of themselves that is most flourishing, right?Link

There's a version of me that's on a beach in, you know, Hawaii, just getting fat and eating Cheetos and watching VR, and, like, maybe that version is really happy. Like, maybe you say, oh, you're not really happy, you're just, you know, in this stupor of, you know, pleasure and whatever. It's like, no, no, no, I'm really, really happy. I am completely loving my life and everything about it, and I don't want anything else. You would reject that. You would say, well, you can tell me that you're happy, but that's not happiness, that's something else. And I don't think that's right. I don't think that it's true that it's not happiness. But it's not flourishing.Link

And flourishing, in a way, it's like, how do you know if a plant is flourishing? It's not just that, okay, the plant has a lot of water. You can water the hell out of the plant. It's not just, oh, the plant is, you know, really big. Okay, that doesn't mean that the plant is flourishing either. The plant is flourishing when it is at its greatest degree of complexity, when it becomes the full version of the plant, right? And that flourishing doesn't necessarily mean that, like, it got a ton of water. It doesn't mean that it did all the things. It meant that it became the full flower, right? Or the full, whatever it is, full plant. That's the way I think about it for a human being, is that it may be a happy process to flourish, it may not be a happy process to flourish, but becoming the fullest flower that you can be, that's what flourishing means.Link

LubaYeah. I think in simple terms, it's realizing your potential.Link

HaseebIt can be.Link

LubaOr, like, realizing yourself to the version that you want to become.Link

HaseebYeah. Because it's always, your potential in what?Link

LubaYeah.Link

HaseebBecause everybody's pluripotent, right? I could go and become a fucking pole vaulter. Probably not well, but, you know, I could do it. Maybe if I spent my entire life just doing pole vaulting, I'd be, like, pretty good at pole vaulting, you know? Or maybe that's a joke of an example. Let's say instead, you know, something else. I could be a writer. I could be a, you know, whatever. Who knows? I could be an electrical engineer. I could go into government, right? These are all forms of excelling at something, but they don't equally capture what I mean by flourishing.Link

LubaWhy is society so obsessed with the pursuit of happiness? Why isn't it rebranded into flourishing?Link

HaseebWell, because happiness feels good. Why would it? I think, like, happiness is obviously more compelling if you're not told to believe otherwise. Like, you would have to be told that it's better to be a really impressive person than to just, you know, jerk off all day and eat Cheetos. Because most people jerk off all day and eat Cheetos. They don't try to become great people.Link

So, like, the real question is, like, how does one get so warped that one does not want to just wirehead yourself and constantly be, you know, awash in dopamine, by consuming all of the wonders of modern, you know, onanism? And the answer is that you have to be told to want that. Somebody has to tell you that you should want to be a great person. You should want to be good to other people. You should want to be reliable for other people, such that the world is better off for you having been here. You have to be told that. You have to be given messages. You have to be shown that this is honorable and that this is great.Link

And if you're not shown that, of course you're not going to believe it. You're going to, you know— if you grow up in a town, or in a society, or in a community, or in a neighborhood where what you're shown is just pure greed, or pure criminality, or pure, like, look, these are the people who get ahead, go join the mafia, go kill some people and become the most powerful person, that's the best thing to be— you'll do that too.Link

LubaThis makes me think of religion, and how a lot of religious teachings kind of, you know, teach you to be virtuous, to be a great person, to be good to your neighbors, to be good to your family. Is that what we should come back to, to reinstill those values into society, now that we have even more things to—Link

HaseebI mean, I said before, I'm not a social planner, you know? So, like, should we go back to religion? I mean, we can't. There is no going back to religion, unless you want to start another crusade. Like, people are going to believe what they believe. So again, as an individual, I think I can give a message that pushes back against a void that's in the zeitgeist, but I can't make that void go away.Link

LubaOkay. So part of the thing of becoming a man is being strong mentally and achieving the things that you would want the best version of yourself to achieve, which comes to discipline. You're really, really disciplined, and you have systems that allow you to be more disciplined.Link

HaseebYeah.Link

LubaWhat are your guiding principles of discipline these days? Has it evolved at all since when you were trying to cultivate discipline in yourself at a younger age?Link

HaseebYeah.Link

LubaAnd, yeah, what's your advice to someone who wants to become disciplined?Link

HaseebYeah, I was much more draconian when I was in my early 20s. So when I was in my early 20s, I fasted twice a week. I never drank anything besides water. I still do that. Although I sometimes drink tea and things like that.Link

LubaOh wow. I didn't know that. I mean, when you—Link

HaseebNo, no, I don't drink tea by myself. I drink tea when people offer it to me. And—Link

LubaYeah. You were also very, very draconian on your diets. Paleo.Link

HaseebYes.Link

LubaNow you're a little more chill.Link

HaseebI'm a little more chill now, but at the time I was extremely, you know, never bread, never sugar, never, you know, never potatoes. And, yeah, all sorts of things like this. And I've let up on a lot of these things because I think I've realized, you know, it's kind of like, many of these things were sort of talismans that allowed me to know that I was cultivating discipline in myself.Link

And a lot of it was because I also knew that I was a very undisciplined person. So, you know, when I was growing up, like, when I was in high school, I stayed up late every single night. You know, I slept, like, three, four hours. I'd play computer games until late in the night, never do my homework. I would do it the morning before. I'd sleep through class. Like, I was just a shitty smart kid. And I kind of made it through by the skin of my teeth, just because I had enough natural intelligence to be able to skate by. But I was completely undisciplined.Link

And when I became a poker player, it became even worse, because poker, you can play, you know, you can play poker late hours of the night. You're surrounded by people who are super unhealthy. You're very isolated, because, you know, you're not going to an office. You don't have colleagues. It's a very chaotic lifestyle.Link

And so I knew that I was not a disciplined person when I started to implement a lot of these rules for myself. And I stuck to them, and sticking to them for me was incredibly important, because it showed me that I was capable of being that kind of a disciplined person. And I think that, more than anything, was probably the thing that mattered, was proving to myself that, okay, if I impose this level of discipline on myself, I can do it. And if I can do that, then if I decide to do something else, I'll be able to do that too.Link

It's almost like building up these contracts with yourself and making sure that you don't break them. There's a rule that I really cultivated in myself, is that if I made an agreement with myself, I would not break it. And that's the only way that you can really develop trust in someone.Link

LubaI think that's the only way you can truly develop self-respect as well.Link

HaseebThat's right. That's right.Link

LubaSo how has that changed now? So you're a little more loose. Is it because you've proven to yourself that, if necessary, you can do it? Or is it just now part of your nature, where you started off with being incredibly undisciplined, and now, with so much discipline throughout years of your life, or I guess almost a couple of decades of your life now, it's now a part of your personality that, hey, you're actually a very disciplined person, so you don't have to think about it too hard?Link

HaseebIt's a good framing. I think it's a little bit of both. I think probably the biggest thing is that I've realized that, you know, in the beginning of a relationship with somebody, a small piece of information will lead to a big update in who this person is, right? So if you meet a new friend and they stood you up the first time you're going to meet, it's like, okay, wow, this person is, like, a flaky son of a bitch. Like, first meeting, you're going to stand me up? Like, that tells me, like, I know that you're at least 50% unreliable, you know, if you stand me up on the very first meeting. But if it's the eighth meeting, the ninth meeting, the 10th meeting, this person stands you up, it's like, oh, you know, probably something came up, and, oh, their dog got hurt, or I don't know, who knows?Link

And so the longer that you know somebody, and you feel that trust in that contract with that person, the more you realize, like, oh, this doesn't actually mean that much about this person, that they failed to fulfill this contract. And I think that's very true in terms of my relationship with myself. Is that as I saw more and more of myself being able to hold on to that discipline, when you start to softly let go of certain parts of that discipline, you see the rest of it doesn't unravel. It's like, oh, I can still rely on myself, even if I sometimes, you know, whatever, drink tea or eat potatoes or whatever the hell it is. And so I think that's also where a lot of that security comes from. Is that if you'd asked me in my early 20s, I think I really would have told you, if I don't do all of this, I don't know if I'll do any of it.Link

LubaSo for someone who wants to become very disciplined, is it about making those contracts with yourself and proving to yourself that you can indeed keep them?Link

HaseebYeah, I mean, that's the rule, is never break a contract with yourself. And if you don't think you can keep it, don't make the contract.Link

LubaWhat if you, you know, took on a contract, and then midway through the contract you realized that that contract wasn't that important to you?Link

HaseebThen have that conversation with yourself, you know? Like, again, as long as you are not violating your expectations for yourself, that's ultimately what it comes down to. So, you know, if you text your friend and you're like, hey, I'm not really hungry, are you sure you want to still go to this dinner? He's like, no, it's fine. Okay, you didn't violate the contract. It's you not showing up that is the real violation of the contract.Link

LubaI think you're going to a Vipassana in a couple of weeks.Link

HaseebThat's right.Link

LubaAnd it's been—Link

HaseebI think it's next week, or— no, sorry. Two weeks.Link

LubaTwo weeks. Yeah. Yeah. In a couple of weeks. And it's been, like, a yearly thing that you do, that allows you to set vision for the next year, to solidify the lessons that you've learned this year. Tell me more about that practice, and why did you pick that as the way to reflect on your life?Link

HaseebI don't know that I picked it so much as I—Link

LubaIt picked you.Link

HaseebIt picked me. I mean, that's a little trite, but I'll take that.Link

Yeah. So a silent meditation retreat is really like nothing else that you can do. It's intensely isolating, maddening, lonely. And it forces you to really confront anything that you have not stared at face-on in the corridors of your mind. Every single painting that you're hanging in your head, every single door that you haven't opened in a few years, you will explore every nook and cranny of your mind if you are on a silent meditation retreat. And it is intensely clarifying for questions that you have not given yourself the space to ponder, or the time to ponder.Link

A lot of it is, like, okay, things going on in your life, relationships, people you've wronged, people you haven't spent enough time with, you know, things that you're not prioritizing. There's also just things like your death, your childhood, your education, your family, like, what it is that you are on this earth to do. A lot of these questions that you just don't sit around every day confronting, but you will confront if you have enough time with yourself. So that's why I do it. I find it clarifying in a way that is almost impossible to achieve any other way.Link

LubaAnd is that the primary way you're setting goals, vision for yourself every year, or do you have any other methodologies to do so?Link

HaseebI mean, you know, professionally we set goals on a more regular cadence. In terms of personally, I do sometimes try to take stock and set goals, but almost always at the end of the year, oftentimes after a meditation retreat, I will set these kind of larger, more inclusive personal goals for myself.Link

LubaHow many days do you recommend going to Vipassana for, to really reap those benefits?Link

HaseebI'd say at least four days. If it's shorter than four days, it's kind of not hopeless-feeling enough. You kind of need to go through the valley of darkness. And everybody says that usually, like, on the third day is when you go a little crazy. And that's, like, you know, you got to give yourself that gift of going a little crazy.Link

LubaAnd why did you pick— well, I already asked you why did you pick Vipassana. But, you know, there is psychedelics you can take, there is therapy you can do.Link

HaseebYeah, it's not the same thing. It's absolutely not the same thing. You've never done a meditation retreat?Link

LubaNo. I mean, I was planning to do it. Yeah, this fall.Link

HaseebIf you do it, you will understand what I'm talking about. It's not like taking psychedelics. It's not like getting therapy. It's the most basic and naked confrontation with your own self. It's just you and yourself, for however many days.Link

LubaSo say you, you know, you've discovered those lessons, you have done the recounting of how the year has gone, what you want to change in the next year. Do you do any sort of intermediate, like, half-a-year, quarterly reviews of, how am I actually doing on the thing that I said to myself I care about? Or is it just a reflection at the end of the year?Link

HaseebMostly just reflection at the end of the year. I do keep track of my goals. You know, I have them written down, and I will occasionally revisit them just to think about how I'm doing. But—Link

LubaHow do you write them down? Is it just, like, written in a notebook, in a doc?Link

HaseebIt's in a doc.Link

LubaHow often do you look at them?Link

HaseebMaybe, like, three times a year.Link

LubaOkay. Okay.Link

HaseebNot often.Link

LubaIs it, like, on your calendar? You—Link

HaseebNo. No. No.Link

LubaYou just randomly remember?Link

HaseebAnd I have a group of friends that we share with each other our year-end goals at the end of every year. And so every year we have, like, a long email thread that we've had over the years, that we'll share with each other. Here's my goals for the year.Link

LubaWow, that's very nice. Do you guys keep each other accountable?Link

HaseebIt's not that we keep each other accountable throughout the year, but that we do reflect at the end of the next year. Did we accomplish the goals? How do we feel about how we did on the goals that we set?Link

LubaHave there been any times where you created a story for why you have not achieved a goal, so that you could look good in front of your friends?Link

HaseebNo. No. I mean, yeah, it's pretty honest. But I think also, like, it's very common that you'll set a goal and not accomplish it. Sometimes it's because it was the wrong goal. Sometimes it's because the goal was too ambitious. Sometimes because you just didn't have the space to be able to prioritize it. So I think if you're hitting 100% of your goals, you're not setting goals aggressively enough.Link

LubaSo given, you know, we're going into the end of the year, I think this episode will come out at the beginning of the year, which is still very much a time to reflect on how you want the year to go. Has your process of how you set goals, in terms of, are they super metrics-driven? Are they incredibly specific? Are they kind of broad? Has that changed over the years? Or are you following more or less the same, like, goal-setting framework?Link

HaseebI think the framework is pretty simple. I mean, I try to make sure that my goals are all measurable and very, very clear, so I'll know whether or not I accomplished it. It's not, like, get better at blah blah blah. You know, like, okay, well, I accomplished that in five minutes, cause I got a little bit better. So you want to make sure that your goals are things that are clear, and you will know for certain, did I hit the goal or did I not hit the goal, and you'll know the exact day that you do.Link

LubaSo what's an example of a very clear goal that is specific enough and also ambitious enough? Or, like, the way you track it allows you to see that it was ambitious enough?Link

HaseebYeah. So, I mean, some of the goals that I had set— I mean, there's either outcome goals or process goals, right? An outcome goal is, I want to achieve XYZ. So, you know, I want to raise my next fund by blah blah blah date. I want to raise at least this amount of money. A process goal is that I want to, you know, every week do a, you know, AI paper review, at least, you know, 40 weeks out of the year, right? So that's a process goal, that, okay, I don't know that I'll achieve anything by doing that, but I will do this process, and hopefully a good outcome results from engaging in that process. So I set goals for myself that are of both kinds.Link

You want to make sure that the goal is realistic. So, like, give yourself enough flex that, you know, if you miss one week, your goal is not dead. Like, I am planning to do travel, have stuff come up, be in the, you know, whatever, have other constraints that make it difficult for me to accomplish this goal with 100% efficacy. So building in the flex of, like, okay, this is tough, but it's clearly setting high expectations for myself.Link

LubaMakes sense. Thank you for the rundown. I'm going to ask a bunch of questions without necessarily a specific theme, so it's almost like a lightning round. Or treat it how you— sorry.Link

HaseebShould I answer quickly?Link

LubaNo, no, not necessarily. I'm just telling you that there isn't a cluster of questions on a specific topic.Link

HaseebYeah.Link

LubaWhat insights about life have you acquired that feel obvious to you now, but not to others?Link

HaseebMoney doesn't make people happy.Link

LubaI feel like that's obvious to a lot of people now.Link

HaseebI think it is not obvious to a lot of people. Or maybe another one is that you should spend your money on experiences, not on things.Link

LubaMaybe we're just in the bubbles where, you know, we're—Link

HaseebYou're in the self-help bubble, so you get all this shit. Yeah. No, I think most people do not do either of those two things.Link

LubaInteresting. Okay. What do you think people waste the most energy on?Link

HaseebWhat do they waste the most energy on? Hm, that's a really interesting question. What do they waste the most energy on? Okay, you go for it.Link

LubaI think people waste a lot of energy—Link

HaseebThe most energy.Link

LubaOr— the most energy—Link

HaseebThe most energy.Link

Luba—on thinking about things that they're going to be doing at some point down the line in the future, versus actually doing them in the moment.Link

HaseebAll right, that's a good one. I'll say they waste the most energy worrying about what can go wrong.Link

LubaThat's actually a good one. This reminds me of a conversation you and I have had multiple times about catastrophizing. Yeah. That people always have this idea, this very innate idea, that the worst-case scenario is going to be a giant catastrophe in any given situation, and that usually is, like, very emotional and irrational. Is that similar to what people are wasting energy on, like worrying slash catastrophizing?Link

HaseebYeah, I mean, there's, like, worrying where you're just, like, spinning your gears, like, thinking about, oh, what if my girlfriend's going to break up with me? What if this thing is going to happen? What if blah blah blah? So there's, like, spending time worrying about that stuff, and, like, spending energy worrying about this stuff, that's not useful.Link

But then also there's, okay, if you're going to worry about— like, it's not to say you should never worry. You should definitely worry. There are things worth worrying about. But when you worry, do you worry correctly? And that's more what I'm pointing to, is, like, hey, if you're gonna worry about the downside risk, right? Like, if you're worrying about, oh, should I, you know, take my partner to a war zone? It's like, okay, yeah, you shouldn't do that. You should worry about doing that. That's a bad idea. There are really things to worry about.Link

But then there's, okay, you know, if I quit my job, I'm worried that I'm going to lose my apartment, I'm gonna, you know, end up becoming homeless, I'm gonna have to go move back in with my parents, I'm going to— and it's like, okay, well, that is not at all the likely outcome. The vastly more likely outcome is that you will quit your job, you'll go look for a new one, and you'll get one. And if you don't get one, maybe you'll go for a little while before you get one. And if you don't get one, then you'll try to go back to your old job, and they'll probably take you back. And there's, like, all these things in the middle before this, like, gigantic catastrophe that you're imagining. That's, like, a 1% chance.Link

LubaYou and I had to talk about it when I was leaving the—Link

HaseebThat's right. Because you were like, I'm going to die, I'm gonna be homeless, and they'll have to ship me back to Belarus, and I'm going to move in with my parents, and I'll have to relearn Belarusian, or Russian.Link

LubaRussian.Link

HaseebOkay. So, catastrophizing.Link

LubaCatastrophizing. Who are your mentors today?Link

HaseebWho are my mentors? I'd say probably my primary mentor has been Naval. Before him, I would say Ned, this guy Ned Ruggeri at App Academy. He was a mentor to me. He taught me a lot. Kind of took me under his wing. Besides that, I'd say I haven't really had mentors besides them.Link

LubaDo you have a dream mentor?Link

HaseebA dream mentor?Link

LubaIt's, you know, how some people are like, can you be my mentor?Link

HaseebYeah, I do get that a lot. Do I have a dream mentor? I can't think of one. Again, there's people I admire and respect, and people I'd love to spend time with.Link

LubaOkay. Who are the top three people you'd like to spend time with? You know, this is The Luba Show. It's an opportunity for those people to hear.Link

HaseebWho do I want to spend time with? Hopefully they're listening, and then they—Link

LubaYeah, exactly. That's what I'm saying. Yeah, that's why I'm asking you this question. This is your choice.Link

HaseebWho do I want to spend time with? I'd love to spend time with Ilya Sutskever. Probably number one person I'd love to spend time with. He is just absolutely fascinating. Like, every time I listen to him talk, I just get this depth of knowledge and insight about what's going on in AI, and just, I don't know, I just love listening to him. Second person I'd love to hang out with is probably Tyler Cowen. He's an economist. I also listen to much of what he puts out and what he writes. And—Link

LubaI went to an event recently where he was.Link

HaseebOh yeah?Link

LubaYeah.Link

HaseebDid you meet him?Link

LubaI did not. No, there was a bunch of people, and there wasn't, like, really a direct opportunity to meet him, but—Link

HaseebYeah.Link

LubaIt was in the periphery.Link

HaseebI did meet him once, extremely briefly, at an event, like, 2017, a long time ago. We didn't talk, but I— oh, I love your work. Just went and sat down in my chair.Link

And then who else would I love to meet? I mean, I'd love to meet Christopher Hitchens, but he's dead, so I can't meet him. But probably, if I could meet anybody living or dead, he would be the number one person.Link

LubaWho's the third alive person?Link

HaseebThird alive person?Link

LubaYeah. Yeah.Link

HaseebYou didn't say that they had to be alive.Link

LubaOkay, now I'm specifying the—Link

HaseebYou're adding extra constraints now.Link

LubaYes.Link

HaseebOkay. Okay. They have to be alive. A reanimated Hitchens. They, like, plug him into Neuralink and then just get—Link

LubaWell, you can probably already do that with an LLM, you know? Train the LLM.Link

HaseebIt's not the same. It's not the same. You know, it's too stiff.Link

LubaThat's your answer?Link

HaseebThat's my answer.Link

LubaOkay, great. Okay. Who shapes your thinking most right now?Link

HaseebWho shapes my thinking most right now? Who shapes my thinking? Am I being shaped?Link

LubaSure. Yeah.Link

HaseebI don't know. Maybe the aliens are shaping my thinking. Maybe I have LLM psychosis and they're shaping my thinking.Link

LubaI think that's possible.Link

HaseebYeah, I think that's, you know, that's probably the answer, is that, like, GPT-5 is shaping my thinking.Link

LubaAre you mostly using GPT-5 these days?Link

HaseebYeah. Yeah. I use Claude as well.Link

LubaWhat about Gemini, now that it's on Chrome?Link

HaseebI use a little bit of Gemini. Why, are you trying to sell me something? I use a little bit of Gemini, but mostly when it's, like, uniquely good at the thing. But yeah, I use mostly ChatGPT and then some Claude.Link

LubaWait, are you using one of the AI browsers?Link

HaseebNo.Link

LubaWhich browser are you on?Link

HaseebI'm on Chrome.Link

LubaOh, you're not using Gemini on Chrome? It's my hypothesis that everyone will convert to Gemini, because it's now on Chrome, and most people use Chrome.Link

HaseebI don't use Gemini in Chrome.Link

LubaOkay, got it. Well, I've also only tried it a couple of times. I haven't converted yet, but—Link

HaseebYeah. Okay. So, I mean, I have Gemini as a tab in Chrome.Link

LubaOkay, got it. Got it. Okay. What's the best coaching advice you've ever gotten?Link

HaseebCoaching advice, like, from a coach?Link

LubaCoaching advice specifically on leadership.Link

HaseebThe best coaching advice I've gotten on leadership. Someone coaching me on leadership?Link

LubaYes.Link

HaseebI don't remember.Link

LubaOkay, it's fine. Skip that question.Link

HaseebOkay, skip that question. Bad question.Link

LubaI hear you talk about movies a lot, but I actually don't hear you talk about books a lot. What are some books that shaped you?Link

HaseebSome books that shaped me? What are some books that shaped me? I'd say *Siddhartha* was a book that shaped me.Link

LubaYeah. What a great book.Link

HaseebWhat other books shaped me? I don't know. There are books that I love. I don't know that I've been shaped by so many books. I don't know. I resist that question. I don't feel very shaped.Link

LubaMaybe that's something to examine and explore.Link

HaseebYeah, I think I shaped myself, mostly. I don't think, like, I was so shaped by other things.Link

LubaI think you take too much credit.Link

HaseebYou think so?Link

LubaYeah.Link

HaseebWell, if I did get shaped, I don't think it was from books so much.Link

LubaOkay. Are there any recent books that you've read that you really enjoyed, that you would recommend?Link

HaseebI listened to an audiobook very recently that I thought was very good, which is totally orthogonal from anything your audience would care about. It is, I think, like, *Great Trials in History*. So it's, like, basically these sort of historical vignettes told through famous trials.Link

LubaI don't think it's that orthogonal. It's people, and people's incentives and motivations.Link

HaseebYeah, potentially. Yeah. Okay. But yeah, it's like, you know, the trial of Socrates, the trial of, you know, Galileo, going all the way to, you know, O.J. Simpson.Link

LubaVery cool. Top three movies everyone must watch.Link

HaseebEveryone must watch?Link

LubaYes.Link

HaseebWhy must they watch them?Link

LubaBecause you recommended them.Link

HaseebOkay. All right. Okay. Top three movies everyone must watch. I mean, my favorite movie ever made is—Link

Luba*Titanic*.Link

HaseebThat was number two.Link

LubaWell, really?Link

HaseebNo, not at all. I've actually never seen *Titanic*.Link

LubaAre you serious?Link

HaseebI am absolutely serious. I've never seen *Titanic*.Link

LubaYou must see *Titanic*.Link

HaseebI know what happens in *Titanic*, so I don't think I need to see it. But no, I never saw it. Okay, so, *Parasite*.Link

Luba*Parasite*.Link

HaseebI'm guessing your number one is *Titanic*.Link

LubaI do like *Titanic*. Bless you.Link

HaseebExcuse me. Okay. So number one, *Parasite*. Number two movie that everybody must see, I would say *Samsara*. And number three movie that everybody must see— hm, everyone must see, I don't know. It's hard to call the number three. I'm imagining, like, what you're going to, like, send out to the aliens.Link

LubaYeah. I'm bad at number three, because number three is, like, there's a finality to it, and I always like to keep, you know, the door open.Link

HaseebDoor open. That's right. That's right. I don't know. Maybe something like *American Beauty* or something.Link

LubaYeah. Yeah, it's a great movie. It's a great movie. What do you still feel like you haven't figured out?Link

HaseebWhat have I not figured out? A bunch of stuff. I have not figured out what compels animal spirits to change in markets. I've not figured out why societies move away from liberal values and towards illiberalism. I've not figured out why people can so easily forget things that they believed very recently. A lot of these things still feel very unintuitive to me, very surprising to me. It's, like, the ways in which individual behavior changes so much in groups and in societies. That is still a little bit of a mystery to me.Link

LubaHave you given up on those questions, or—Link

HaseebHave I given up? I mean, some of them I've given up on, and I just think they're kind of inscrutable. Like, just, complexity theory makes it so you'll never have a simple explanation of it. Others of them, I'm still trying to get a better mental model of.Link

LubaAnd last but not least, a very important question.Link

HaseebYeah.Link

LubaIs crypto happening?Link

HaseebCrypto is definitely happening. It's happening as fuck.Link

LubaAwesome, Haseeb. It was great to have you here.Link

HaseebThank you for having me. Goodbye.Link

LubaThank you for taking the time.Link

HaseebThis was the best podcast of my life.Link

LubaAmazing.Link

HaseebBest podcast I've ever had. Thank you.Link

LubaAwesome.Link