Original Title: $4B Crypto Fund, Manhood, Discipline, VC: Haseeb Qureshi Original Author: Life of Luba Compiled & Translated by: CoolFish PS: (Some content has been abridged) Luba: Hi everyone, welcome to the Luba Show. Today my guest is Haseeb Qureshi, Managing Partner of Dragonfly Capital, a $4 billion cryptocurrency venture capital fund. Haseeb and I talked about a wide range of topics, from masculinity, cryptocurrency, Airbnb, and much more. It was a particularly interesting conversation because we've known each other for so long. It was really fun to delve into topics we hadn't discussed before with someone as smart, thoughtful, and familiar as Hasib. Haseeb, it's great to have you here. Hi Airbnb, but I hate birthdays. Luba: I want to start with where we first met. Let me describe the scene. I was in an Airbnb microkitchen when you walked in. Haseeb: There are a lot of microkitchens there, I think this was the one near the "Cairo" meeting room. Luba: Yes, good memory, it was "Cairo." And I clearly remember you had just written a blog post about salary negotiations that went viral in the tech world. It was basically about how you received offers from various tech companies, and publicly disclosing your salary was very controversial at the time. But in the blog post, you were very open and transparent about how much Yelp offered you, how much Google offered you, what Airbnb offered, and how you negotiated your total compensation with Airbnb from around $120,000 to around $250,000. Business Insider even published a popular article about you with your face plastered on it. It felt incredibly arrogant at the time, like, "Who is this jerk who talks about making a fortune?" I read that blog post, and I remember walking into the kitchen and thinking, "Oh, that's the megalomaniac who wrote that blog." Haseeb: Wow, I don't think you've ever used that word before. Thanks. Luba: But then we started talking, and within minutes, my opinion of you completely changed. In fact, you even convinced me to join your team because I was still in bootcamp while you were already working on the fraud prevention or risk team. I decided to join that team because your pitch was very persuasive and you were actually quite likeable. Haseeb: What did I say at the time? Compared to that article. Luba: I remember you telling me that I would learn a lot as a backend engineer, and I had never done backend work before. You said fraud prevention was like a cat-and-mouse game, and I would learn a lot.Haseeb: Was that my story? I don't remember at all. Luba: Yes, you really convinced me. So basically, you completely changed my first impression of you before we met. Haseeb: After that blog went viral, I naturally felt the attention. It was a very honest post about my tough, frustrating, and fruitless job search, and then suddenly everything started to get better. I remember writing about applying to about 30 companies and not getting a single response. Luba: I remember you ended up getting 12 offers? Haseeb: No, it was 8. I ended up getting 8 offers and finally chose Airbnb, which was a very popular company at the time. After I wrote that blog post, it went viral immediately. At the time, my blog only had about 100 readers. Luba: Only 100? Haseeb: Yes. Because the readers were mostly people I met at the App Academy coding bootcamp, and some followers from my time as a professional poker player. Back then, I wasn't a public figure; they just wanted to know how Haseeb was doing. I thought, "Okay, this is my life." I had no idea it would become such a big deal. So when it went viral, everyone at Airbnb not only knew how much I made, but everyone had an opinion about me. I remember being called in to see the VP of Engineering and the General Counsel the first week, and I thought I was going to be fired. I thought, "That's it, I just announced I got such a great offer, and now I'm going to lose it." But they acted very calmly. However, everyone at Airbnb looked at me with a kind of "disdain," as if I shouldn't be there, or that I was exploiting a loophole in the system. I remember searching my name on Slack and seeing what people were saying about me behind my back because they didn't realize I was on Slack. In short, I had a strong "imposter syndrome" back then, and I would feel that way even if no one knew, but now I feel like everyone is scrutinizing and judging me, and it really is. I remember helping you debug some random things, like Airlock. When I could help, I thought, "Oh wait, maybe I can do this. I'm actually qualified to work here." So I felt really good during our first interaction. That was the first time I offered substantial help. Luba: I should clarify, that interaction also felt good after breaking down that first impression of you. But I'm curious, how did you feel when you first joined the company and faced the disdain or strange looks from people?Have you been actively trying to change that image? Haseeb: I was aware of it because it was headline news in the tech world. For the first few weeks, when I looked at people, I wondered: Is that a look of recognition, or just the look of someone looking at a newcomer? After a while, I stopped thinking about it because people gradually forget that you're "the person who wrote the blog." But I do care a lot about first impressions, and I realized I had to prove myself by "doing" rather than "saying." And I was already motivated to prove myself because I was older than other newcomers at my level, I didn't have a computer science background, I studied liberal arts at a state university. I wasn't a typical Airbnb employee. This accelerated my need to prove myself to others. Luba: Describe the context when you wrote that blog post. Back then, salaries weren't transparent, unlike now with Levels.fyi, Glassdoor, where everyone openly talks about salaries. Haseeb: Yes, that culture wasn't mature back then. Interestingly, I didn't intend to make any statements to Airbnb. I didn't expect anyone at Airbnb to read my blog. I read another person's blog post at the time, where he wrote about his job search process, offer letter, and negotiation strategies, which was very helpful to me. I thought it would help people looking for jobs, and personally, speaking out wouldn't cost me anything. I didn't realize then that revealing how much money I made would be politically charged. Several people messaged me saying, "Thank you for posting this, because I didn't know I was owed wages." Of course, there was also a group of people who thought I was an idiot. I remember someone on Slack asking, "How did this guy pass the values interview? He's obviously a megalomaniac." Someone else said, "Don't talk about values, how did he pass the technical interview? He just graduated, there must be something wrong with our process." Then an L6 engineer who had interviewed me replied, saying, "I interviewed him, and he did perform very well." As for why it went viral in the media, it wasn't because I was talking about salary, but because people wanted to see "how crazy Silicon Valley is." The media's perspective was: look at this unskilled loser who can earn so much money after just two months of bootcamp; Silicon Valley is too easy to fool. They portrayed me as a poker gambler, a conman who tricked his way into a coding job. It was a great "tech bubble" story at the time. I was just one example of the political story they wanted to tell. Luba: I really liked your mention of Airbnb's values interview. I read your blog for this conversation. You wrote, "I'm so excited to join the Airbnb family." I laughed when I read that.Because you're very different from the traditional Airbnb "family" feel. I really fit in, it was very social. But you're an outsider in every way, even culturally out of place. What were your expectations and reality when you joined? How did that shape you? Haseeb: Airbnb was my first job in a formal company. Before that, I was a professional poker player. It was another universe, no bosses, no OKRs, no performance reviews. Although I had worked at App Academy, it was just a small company of 12 people. I wasn't ready for an environment like Airbnb at all. I naively thought I would get promoted here and do what they wanted me to do. Airbnb was rated as one of the best workplaces at the time. There were all sorts of perks: coconut water, nuts, snacks, a very refined and comfortable work life. But I didn't care about any of that. I'm not a natural "team player." I'm more like a "lone wolf"—if you ask me to do something, I'll do it well. But I didn't want to get together every day to celebrate birthdays. We had a team of about 50 people at the time. Whenever someone on the team has a birthday, we have to get together to cut a cake. That means every week, every single week, you're sitting in the same room cutting a cake and singing "Happy Birthday" to someone. I hated that. I wanted to say, "Let's get work done." Luba: I'm surprised you said you're not a team player because you lead a large team, you're very good at mentoring and guiding people, and you've worked with many founders. Isn't that typical teamwork? But I guess you're referring to those social events where you're there, but that's not your purpose. You're there to succeed, to succeed through work, not to sing "Unity Song" together or act like family. Haseeb: Yes. Even today, when I manage Dragonfly, it's the same. We're not all best friends, at least not with me. I'm a great partner, very reliable and transparent. But I'm not your "chum." Some people need to be true friends with their colleagues, and they might not enjoy working with me. I really resonate with the story of Dennis Rodman in the documentary "The Last Dance." The Bulls were a legendary team with immense trust and teamwork on the court, but the documentary revealed they were almost completely silent off the court. I thought to myself, "Oh, I'm not crazy." Kobe Bryant was the same; he was a ruthless executor, but not very sociable off the court. Luba: Have you tried the Airbnb approach?Haseeb: I tried it, but it was incredibly painful. There were so many extracurricular activities. Like, “Today we’re taking a day off to beautify the city.” I thought, “Why? Do we really need to do this? Can’t we just work?” For a lot of people, it sounds great, but for me, if I wanted to do these things, I would do them myself. Luba: Does that make you realize that it’s something you absolutely don’t want? Haseeb: Yes. The birthday thing definitely left me with a lifelong trauma. At Dragonfly, we had 50 people, and early on we debated whether to celebrate everyone’s birthday. I insisted: Absolutely not. We could post a message on the Slack birthday channel, and everyone could decide whether to receive a uniform gift, but we wouldn’t put in the effort to celebrate. They have their own lives, and we’re not their friends. Luba: What if someone wanted to spontaneously send a cake to someone in a subteam? Haseeb: No problem, I’m not the Grinch, I’m not stopping people. I’m just saying what kind of interaction norms we need to establish as an organization, and the answer is: professional. I have extremely high standards for responsiveness, reliability, and transparency. But if you don't want to talk about your personal life or making friends, that's perfectly fine. Mentoring founders is essentially teaching people. Luba: Let's go back to the memory of you helping me debug code. You really helped me a lot in the first few months because I was also suffering from severe imposter syndrome, doing backend work for the first time. I remember those late nights when you taught me Ruby on Rails… Haseeb: Because you didn't know Ruby at the time, you were learning on the job. Luba: Yes, I switched from the Android ecosystem and wanted to challenge myself, so the first few months were very difficult. You helped me explain the code and concepts, and you also helped me mentally prepare: since they hired you, there's a reason you're here. Teaching others has always been a very important part of your life. Where does this instinct to teach come from? Haseeb: I do have a strong inclination to help and mentor others. This instinct probably comes from my mother. Not because she was a good teacher, but because she needed to be taught. When our family immigrated to the United States, my dad spoke English, but my mom didn't. She was confused about the culture and norms here. Before I was six or seven, she couldn't cope with the outside world independently, and even after that, her English was very poor. Because my dad was often away on business trips, as her child, I had to help her understand the world and explain things to her; otherwise, she wouldn't be able to survive. I think that's why I'm good at explaining complex things in a simple way. Luba: I understand.I remember when you left Metastable, it seemed to be to launch a course. So your passion for teaching was so deep that you were even willing to make a career change for it, or specifically set aside time for it. Haseeb: That wasn't a change, it was more like a project. I wanted to create an online course about learning about cryptocurrency and blockchain. I taught that course in 2017 at Bradfield School of Computer Science, an elective, paid school where programmers could learn computer science concepts to stay competitive. I taught cryptocurrency then, and later decided to compile the teaching materials into an online course that was more comprehensive and self-sufficient than any other course on the market at the time. Because there was a severe lack of educational materials on cryptocurrency back then, most people were self-taught, including me. I wanted to complete this project between two jobs, thinking it would only take three or four months, and then I would look for a new job after the launch. But teaching is really ingrained in me; it's something I enjoy, and something I feel has great social value. Luba: How do you satisfy the need to teach people now? Haseeb: As a venture capitalist, mentoring founders is essentially teaching people. I also do a lot of public outreach on my blog and podcast. We have a podcast called The Chopping Block. I wasn't the host initially, but I became the host because I'm the best communicator. I mean, hosting requires a lot of different skills, but the most important one is explaining what the story we're talking about is. Luba: Isn't that a bit boastful? Do your podcast colleagues know you think this way? Haseeb: They all agree. At first, I was a little embarrassed, not wanting to seem too arrogant, not wanting to say, "I'm the best at explaining things, so I'll be the host." So I even asked everyone, "Who wants to be the host?" and let someone else do it. Later, the feedback from the outside world changed my mind. Everyone said, "Haseeb, you should be the host, why not you?" I think this is largely because I can explain the complex things in the crypto industry simply in a way that ordinary people can understand. Luba: How did you become so good at communicating, able to speak clearly and explain complex concepts in a way that's easy to understand? Is it through deliberate writing practice, other efforts, or is it innate? Haseeb: To a large extent, it's through accumulated practice. After all, I've been teaching for so many years, teaching in different fields.Whether it was helping my mother adapt to life in America as a child, or teaching others how to play poker—I taught courses and provided one-on-one tutoring—and later, as a programmer, I've found that the best way to master a new field is to learn first, then teach. There's a hierarchy of learning theory, I forget the exact name, but it makes a lot of sense: the worst way to memorize is simply reading, as bookmarks have extremely low retention rates; the second worst is listening, which is slightly better than reading; the third is discussion, exchanging ideas and discussing with others, which significantly improves retention; and the most effective way is teaching others. Teaching greatly solidifies one's own knowledge, a fact I understood early on. My teaching in different fields is also about becoming more professional—why teach poker? Why teach programming? The answer is always to become better at these things. In fact, I gain even more from helping others. The more you teach, the more intuitive you become: you can distinguish whether someone is just nodding in agreement or truly understanding. Bad teachers seek "approval" rather than "understanding." If you ask, "Do you understand?" no one will say no. You have to get them to explain it to you. If you can't get the other person to understand, that's a failure as a teacher. Furthermore, teaching needs to be engaging enough to make people want to listen. Luba: Are there any things you're currently learning, preparing to teach, or already teaching? Haseeb: I'm constantly learning in the crypto space. I'm also keeping up with developments in AI. I have a study group where we read a new paper each week, then present it to the rest of the group and try to explain what it's about, what the main findings are, what they accomplished, how they accomplished it, and what evidence they used to prove it. If you just read a paper, you'll find your eyes scanning it, almost like running your hand over a wall, but that doesn't mean you really understand it, right? The way to truly understand it is to answer questions, ask questions, and identify where you don't understand the paper. Luba: I have a limiting belief in my ability to teach. Two years ago, when we had our machine learning group, I also hated the days when it was my turn to present because I felt my understanding was too superficial. Haseeb: This pressure forces you to be aware of your own motivation. When you're forced to teach, you have to confront whether you truly understand it. If you don't want to delve deeper, it means you don't really care about that topic; it's a form of self-discovery. Luba: Speaking of self-discovery. You went from poker to programming, and then to Airbnb.But in your blog post, you said that while you're excited about web development now, you know it's not a lifelong commitment. What were you thinking at the time? Haseeb: I knew I wanted to be an entrepreneur. Becoming a developer was the most logical step towards starting a business because if you can't build things, you need other skills to bring to the negotiating table, and all I had at the time was poker. My purpose in going to Airbnb wasn't for a promotion, but to learn how to build, meet partners, and build a resume to make people think I was a capable person. Luba: So when did you feel ready to leave? You left after only one year and one month. Right at the point of stock vesting. Was this planned from the beginning, or did you feel ready at the time? Haseeb: It was basically planned. I thought I might stay longer if there was a promotion opportunity, but I didn't see any hope. So I thought, well, I'm leaving. Luba: After leaving Airbnb, how did the whole process of getting into cryptocurrency happen? It seems like a pretty big leap. Airbnb was about belonging and weekly pie-cutting, while cryptocurrency is completely different. Haseeb: Actually, it wasn't that big. One of the early members of Airbnb's anti-fraud team was Brian Armstrong, the founder of Coinbase. He did the SiftScience integration. I remember seeing "If there's a bug, email [email protected]" in the codebase. Later, I met Brian and the early Coinbase team through the Risk Salon. Luba: I was one of the co-founders of the Risk Salon. Haseeb: That's right. After leaving Airbnb, I hesitated between AI and cryptocurrency. I ultimately leaned towards cryptocurrency because I felt AI was geared towards people with traditional degrees and qualifications (like PhDs), while I was a self-taught liberal arts student. In the crypto space at the time, there were no experts, no textbooks, everyone was self-taught, and everything was being invented in real time. I liked that space full of uncertainty. I got in when the market was hot. You know, the ICO bubble was going on. Everyone was excited. I thought, "Oh my god, I'm just a fame-seeker, I feel like I'm late." But actually, no matter how early you enter any field, you'll always feel like you're late. I remember a story about Marc Andreessen, who arrived in Silicon Valley around 1999. He said he was worried that when he arrived in Silicon Valley in '99, it was basically all over. The dot-com bubble had almost burst, and there wasn't much he could contribute. So people have had this feeling from the very beginning.But it turns out I think my decision to get into cryptocurrency was the right one. Luba: How has Marc Andreessen influenced you? Haseeb: I admire his vision; he invented modern venture capital with A16Z. But I don't want to completely emulate him. His path is very different from mine. I have an unusual background; I've taken such an unusual path to get where I am today that I can't look at any other person's blueprint and say, "Great, if I just do what they do, I'll succeed." I don't think that's true. Marc Andreessen is a very successful investor who built A16Z in a very different environment, facing completely old-school, very different types of investors. I've heard a lot of podcasts and stuff about how he built A16Z and how he invests, but his formula doesn't apply today because it's a different world, a different environment. Luba: Speaking of going your own way, you left Airbnb and decided to really delve into cryptocurrency. You started a company, joined Bology with Earn, and then joined Metastable as an investor. How did that transition from starting a company to playing a VC role happen? Why did you decide to stop trying to start a company and choose this path instead? Was it Naval who truly convinced you, or was it entirely your own independent, principled thinking? Haseeb: It was Naval Ravikant. When I first met Naval, I was working on a startup, and we actually received a merger offer from a large cryptocurrency company. I was consulting with Naval and met him. Luba: Not Coinbase? Haseeb: Coinbase was one of the companies that wanted to acquire us. Luba: I think it was Earn that was acquired by Coinbase? Haseeb: Earn was acquired by Coinbase. I left Earn to start a startup, and that startup received acquisition offers, one of which came from Coinbase. So my initial meeting with Naval was to consult him on how to handle this potential merger conversation. He lobbied me, oh, you don't want to join this company. I said, what should I do then? That's why I'm here. He said, if you get acquired by Coinbase, it'll be boring. You'll be working under compliance. Coinbase is run by lawyers. It'll be boring. You should become an investor. I said, "Become an investor? I'm not, I don't know how to invest. I only buy index funds. I'm not that type of investor. I know nothing about finance." He said, "That's okay, you don't even need to understand finance. Investing, learning the mechanisms of investing is actually easy. I can teach you the mechanisms of investing. The difficult part is judgment."Judgment is scarce, not investment knowledge. So he eventually convinced me to become an investor, which is why I ultimately shelved my startup and turned to investing. But I didn't think I'd be an investor forever. I thought I'd be an investor for a while. I'd make some money. But obviously, being an investor is a bit embarrassing. It's not the coolest thing you can do. The real thing, the actually important thing, is starting a company. Obviously, I'd do that, I'd hang around for a while, and then I'd start another company. But what I didn't know was that the place where I ended up starting a company was actually in venture capital. Luba: Is investing still a bit embarrassing now? Haseeb: Yes. Because venture capital is traditionally a very "elegant" profession, with people taking summer vacations, not replying to messages on weekends, like a retirement job. I'm not that kind of person; I play the game to win. Many small funds' management fees are enough to make the partners very comfortable; they don't need to participate in fierce competition. Even many partners in large companies are like that. But Dragonfly isn't like that; we're very aggressive. Luba: But I think it's too difficult to do that in the current competitive VC deal environment. There are so many VCs. Haseeb: Absolutely. That's why very few VCs are competitive. What do you think everyone else is doing? Luba: How can you make money with VC if you don't treat it as a game to win? Haseeb: It's important to understand some of the economics of VC. First and foremost, a lot of VC funds are small funds. If you raise $50 million and take a 2% management fee, that's $1 million a year. That $1 million isn't just your salary. It's the total amount of all the salaries you pay plus any other expenses not covered by fund fees. So you hire people, hire a CFO, hire someone to handle investments, operations, and so on. Maybe you can save $500,000 a year. So a three-person fund. A $50 million fund, not a big fund. That's a small fund. A lot of people can raise $50 million, hire two people, and take $500,000 home. That's a pretty good salary for anyone. You can coast along; you don't have to be very competitive, you don't have to win every deal. Luba: And then you're most likely to be co-investing in deals, not leading them. Haseeb: Yes, you're not the lead investor. At this scale, you don't have to compete with everyone for a share. You can get some things, but you'll be excluded from most of the hot deals. Sequoia will win, A16z will win. But that's none of my business. I'm not A16z.Even partners at many large companies are like that. For me, the way I run my business, I don't do VC that way. The people at Dragonfly don't do VC that way either. If they thought that way, then this isn't the right place for them. So that's how I built this company. That's why, while VC is embarrassing, I don't think the way we do VC is embarrassing. But from the outside, you can't tell the difference. Luba: What made you decide to stop starting your own business and stay in the investment world? Haseeb: I gradually realized that starting a business isn't romantic, especially in the crypto space. Being a founder is a thankless and brutal job. It's much harder than I think in most other fields. And being an investor is actually always very interesting. There's a lot of bullshit in being an investor. But being an investor is really the best way to try to understand the world, to have a view on where the world is going, and to prove yourself right or wrong based on the investments you choose. In a way, there's no purer way to express your vision for the future than through investing. I don't think I really realized this until I achieved some success as an investor. Then, after I left Metastable and eventually founded Dragonfly, what I realized most was that I really wanted to prove I was good at this. Because I didn't stay at Metastable long enough to prove anything. Luba: Who were you trying to prove anything to? Naval? Yourself? Or the world? Haseeb: The main theme of my life is: I believe in myself far more than anyone else. When I wanted to learn coding, nobody believed a poker player who hadn't studied CS could get into a top tech company. At Metastable, my suggestions later proved correct, but the partners at the time didn't trust my judgment; they just weren't willing to do it. I talked to Paradigm, I talked to Polychain. I wanted to join as a partner. These companies were either not interested in me joining as a partner, or they said, okay, maybe you can work your way up to partner. I wasn't sure if you'd actually done that much. I was thinking, "Screw you, you don't believe I can do it." To be clear, I didn't have much evidence to prove I was capable. I wasn't a big shot, no big brand, no years of investment experience. I was a relatively new entrant into the cryptocurrency space. I'd only been learning about it for the past year. So their reaction to me, for all sorts of reasons, was, why should I believe you can do it? What proof do you have that you can do it? But I believe I certainly can. How could you not know who I am? I'm Haseeb. I'm awesome.Of course I can do it. If I decide to do it, I fucking can do it. So, the gap between how much I believe in myself and how much others believe in me—I don't remember a time when that gap didn't exist. Then I met Bo and Alex from Dragonfly. Bo is a very intuitive person, and he trusted me almost immediately. He saw that I was ambitious and would do anything to win. He promised me an equal partner if I joined. Bo had been in VC for a long time and was very intuitive. He and I were very different. I'm more analytical and calculating. Bo is the complete opposite; he's purely intuitive and purely social. He's one of the best communicators and socialites I've ever met. He's incredibly good at things I'm completely bad at. And I'm the kind of person who fucking hates birthdays, so Bo is the complete opposite. But the things Bo isn't good at—like he's not analytical, not rigorous, not calculating—that I'm very good at. I think that's a crucial factor in a strong partnership, not just mutual respect, but the ability to listen to each other in areas where you both believe in each other's strengths. So, when it comes to funding relationships and building connections, Bo is world-class. If we disagree, Bo is right. When it comes to things like technical analysis and underwriting, when Bo and I disagree, he knows I'm right, and he'll listen to me. So, despite being very different, very different generations, we immediately developed a very, very strong and stable trust. That's why I think I decided, okay, I can work with this guy. Luba: What qualities does this tell you when you're observing teams and co-founders? What about people who are very similar but decide to work together? Haseeb: There's nothing wrong with being similar, it's perfectly fine. I think working with people like that just requires a different approach. I think it's clear that similar teams are more common than different ones. When you're different, what's important is that you genuinely trust each other in your respective areas of expertise. Without that trust, like with [RootData]…