Dialogue with Dragonfly Partner Haseeb: Entrepreneurship is not romantic, and investment can be a bit awkward

Core Viewpoint

Hello Airbnb, but I hate birthdays

Luba: I want to start from where we first met. Let me describe the scene at that time. I was in a micro kitchen at Airbnb, and you were walking in.

Haseeb: There were many micro kitchens; I think we were near the "Cairo" conference room.

Luba: That's right, good memory, it was "Cairo." And I clearly remember that you had just written a blog post about salary negotiation that went viral in the tech circle. That post was basically about how you received various job offers from different tech companies, and at that time, disclosing salaries publicly was very controversial. But in the blog, you talked very openly about how much Yelp offered you, how much Google offered you, what Airbnb provided, and how you negotiated Airbnb's total compensation from around $120,000 to about $250,000.

Business Insider also published a popular article about you, featuring your big face. At that time, it felt very arrogant, like "Who is this jerk talking about making big money everywhere?" I read that blog post, and when you walked into the kitchen, I thought, "Oh, it’s that arrogant guy who wrote the blog post."

Haseeb: Wow, I don’t think you’ve ever used that word before. Thank you.

Luba: But then we started talking, and within minutes, my opinion of you did a complete 180. In fact, you even convinced me to join your team because I was still in a bootcamp, and you were already working in the fraud prevention or risk team. I decided to join that team because your pitch was very persuasive, and you were actually very likable.

Haseeb: What did I say back then? Compared to that blog post?

Luba: I remember you told me that as a backend engineer, I would learn a lot, and I had never done backend before. You said fraud prevention was like a cat-and-mouse game, and I would learn a lot.

Haseeb: Is that really what I said? I don’t remember at all.

Luba: Yes, you did convince me. So basically, you completely changed my first impression of you that I had from the article before I met you.

Haseeb: After that blog went viral, I felt naturally noticed. It was a very candid article about my grueling, frustrating, and stagnant job search experience, and then suddenly everything started to turn around. I remember I applied to about 30 companies and didn’t get a single reply.

Luba: I remember you ended up with 12 offers?

Haseeb: No, it was 8. I ended up with 8 offers and chose Airbnb, which was a very hot company at the time. After I finished that blog post, it immediately went viral. At that time, my blog probably had only about 100 readers.

Luba: Only 100?

Haseeb: Yes. Because the readers were basically people I met at App Academy coding bootcamp and some followers from when I was a professional poker player. At that time, I wasn’t a public figure; they just wanted to know how Haseeb was doing. I thought, well, this is my life. I had no idea it would become a big deal. So when it went viral, everyone at Airbnb not only knew how much I made, but everyone also had an opinion about me.

I remember the first week I was called to meet the VP of engineering and the general counsel, and I thought I was going to get fired. I thought, oh no, I just announced that I got such a good offer, and now I’m going to lose it. But they acted very calm. However, everyone at Airbnb looked at me with a sense of "disdain," thinking I shouldn’t be there or that I had gamed the system. I remember going into Slack and searching for my name, seeing how others were talking about me behind my back because they didn’t realize I was right there in Slack.

In short, I had a strong case of "imposter syndrome," even though no one knew about it, I felt that way, but now I felt like everyone was scrutinizing and judging me, and it was indeed the case. I remember helping you debug some random stuff, like Airlock or something. When I could help, I thought, "Oh wait, maybe I can do this; I am actually qualified to work here." So in our first interaction, I felt really good. That was the first time I made a substantial contribution.

Luba: I should mention that after breaking my first impression of you, that interaction also made me feel good. But I’m curious, when you first joined the company and faced people's disdain or odd looks, how did you feel? Were you actively trying to change that image?

Haseeb: I was aware of it because that incident was headline news in the tech circle. In the first few weeks, when I looked at others, I would wonder: is that a look of recognition, or just the look of seeing a newcomer? After a while, I stopped thinking about it because people gradually forgot that I was "the guy who wrote the blog post." But I did care about first impressions, and I realized I had to prove myself through "doing" rather than "talking." And I had my own motivation to prove myself because I was a bit older than other new hires, I didn’t have a computer science background, and I studied liberal arts at a state university. I wasn’t the typical Airbnb employee. This accelerated my need to prove myself to others.

Luba: Describe the context when you wrote that blog. At that time, salary transparency wasn’t as mature as it is now, unlike now with Levels.fyi, Glassdoor, where everyone talks openly about salaries.

Haseeb: Yes, that culture was not mature at that time. Interestingly, I didn’t intend to make a statement about Airbnb. I never thought people at Airbnb would read my blog. At that time, I read another person's blog where he wrote about the job search process, job offers, and negotiation strategies, which was very helpful to me. I thought this would help people looking for jobs, and for me personally, sharing what happened wouldn’t cost me anything. I didn’t realize that talking about how much I earned would be politically charged.

A few people DM'd me saying, "Thank you for posting this article because I didn’t know I was underpaid before." Of course, there were also a group of people who thought I was a jerk. I remember in Slack, someone asked, "How did this guy pass the values interview? He’s obviously an arrogant jerk." Someone else said, "Don’t mention values; how did he pass the technical interview? He just graduated; our process must have problems." Then an L6 engineer who interviewed me replied, saying, "I interviewed him, and he did perform well."

As for why it went viral in the media, it wasn’t because I was talking about salaries, but because people wanted to see "how crazy Silicon Valley is." The media's angle was: look at this untalented loser who can make so much money after only two months of bootcamp; Silicon Valley is so easy to fool. They portrayed me as a poker player, a fraud who tricked his way into a coding job. It was a great "tech bubble" story at the time. I was just a case study for the political story they wanted to tell.

Luba: I love that you mentioned Airbnb's values interview. For this conversation, I read your blog. You wrote in the blog, "I’m happy to join the big family of Airbnb." I laughed when I read this. Because you are very different from the traditional Airbnb "family feel." I was very immersed in that atmosphere, very social. But you were an outsider in every way, even culturally misaligned. What were your expectations and reality when you joined? How did that shape you?

Haseeb: Airbnb was my first job at a formal company. Before that, I was a professional poker player. That was another universe, no boss, no OKRs, no performance reviews. Although I had worked at App Academy, it was just a small company of 12 people. I was completely unprepared for an environment like Airbnb. I naively thought I would get promoted here and do what they wanted me to do. At that time, Airbnb was rated as one of the best workplaces. There were all kinds of perks: coconut water, nuts, snacks, a very refined and comfortable workplace life.

But I didn’t care about any of that. I’m not a "team player" by nature. I’m more of a "lone wolf"; if you ask me to do something, I’ll do it well. But I don’t want to gather every day to celebrate birthdays. We had a team of about 50 people. Whenever someone had a birthday, we had to gather to cut the cake, which meant every week, every single week, you had to sit in the same room, cut cake, and sing happy birthday to someone. I hated that; I wanted to say, "Let’s work and get things done."

Luba: I’m surprised you say you’re not a team player because you lead a large team, and you’re very good at mentoring and guiding others, working with many founders. Isn’t that typical teamwork? But I guess you mean those social activities, where you’re present, but that’s not your purpose for being there. You’re here to succeed, to achieve success through work, not to sing "Kumbaya" and bond like family.

Haseeb: Yes. Even today, when I manage Dragonfly, it’s the same. We’re not all best friends; at least they don’t become my best friends. I’m an excellent partner, very reliable and transparent. But I’m not your "buddy." Some people need to become genuine friends with colleagues; they might not like 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 huge trust and collaboration on the court, but the documentary revealed that they hardly spoke off the court. I thought, "Oh, I’m not crazy." Kobe Bryant was like that too; he was a cold-blooded executor but didn’t socialize much off the court.

Luba: Did you try to fit into Airbnb's way?

Haseeb: I tried, but it felt extremely painful. There were too many extracurricular activities. For example, "Today we’re taking a day off to beautify the city." I thought, "Why? Do we need to do this? Can’t we just work?" It sounds great to many people, but for me, if I wanted to do that, I would do it myself.

Luba: Did that make you realize that it was something you absolutely didn’t want?

Haseeb: Yes. The birthday thing definitely left a lifelong shadow on me. At Dragonfly, we have 50 people, and early on, there was a debate about whether to celebrate everyone’s birthday. I insisted: absolutely not. We can send a message in the birthday channel on Slack, and everyone can decide whether to get a collective gift, but we won’t put effort into celebrations. They have their own lives; we’re not their friends.

Luba: What if someone wants to spontaneously bring cake for their sub-team?

Haseeb: That’s fine; I’m not the Grinch; I won’t stop others. I’m just saying, as an organization, what kind of interaction norms do we want to establish? The answer is: professional. I have very high standards for responsiveness, reliability, and transparency. But if you don’t want to talk about personal life or make friends, that’s completely fine.

Mentoring Founders is Essentially Teaching

Luba: Back to that memory of you helping me debug code. You really helped me a lot in those first few months because I also had severe imposter syndrome, doing backend for the first time. I remember those late nights when you taught me Ruby on Rails…

Haseeb: Because you didn’t understand Ruby; you were learning as you went.

Luba: Yes, I was transitioning from the Android ecosystem, wanting to challenge myself, and the first few months were really tough. You helped me explain code and concepts and also helped me with mental reassurance: since they hired you, there’s a reason you’re here. Teaching others has always been an important part of your life. Where does that 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 my family immigrated to the U.S., my dad spoke English, but my mom didn’t at all. She was confused about the culture and norms here. Until I was six or seven, she couldn’t handle the outside world independently, and even after that, her English was poor. Because my dad traveled a lot for work, as a child, I had to help her understand the world, explain various things to her, or else she wouldn’t survive. I think that’s why I’m good at explaining complex things in simple ways.

Luba: Got it. I remember when you left Metastable, it seemed like you were going to launch a course. So your passion for teaching is so strong that you were even willing to pivot your career or set aside time for it.

Haseeb: That wasn’t a pivot; it was more like a project. I wanted to create an online course about learning cryptocurrency and blockchain. In 2017, I taught this course at Bradfield School of Computer Science, which is a paid elective school where programmers can learn computer science concepts to stay competitive. I taught cryptocurrency there and later decided to organize the teaching materials into an online course that was more comprehensive and self-sufficient than any course available at the time. Because at that time, educational materials about cryptocurrency were very scarce, and most people were self-taught, including myself. 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. But teaching really became ingrained in me; it’s something I enjoy and feel is very socially valuable.

Luba: How do you currently satisfy your need to teach?

Haseeb: As a VC, mentoring founders is essentially teaching. I also do a lot of public outreach through blogs and podcasts. We have a podcast called "The Chopping Block." Initially, I wasn’t the host, but I later became the host because I’m the best communicator. I mean, hosting requires many different skills, but the most important point is explaining what the story we’re discussing is.

Luba: Doesn’t that sound a bit self-important? Do your podcast colleagues know you think this way?

Haseeb: They would all agree. At first, I was a bit shy about it, not wanting to come off as too arrogant, not wanting to say, "I explain things best, so I’ll host." So at that time, I asked everyone, "Who wants to host?" and let others do it. Later, external feedback changed my mind; everyone said, "Haseeb, you should host; why not you?" I think it’s largely because I can explain complex things in the crypto industry in simple terms that ordinary people can understand.

Luba: How do you manage to communicate so well, being articulate while making complex concepts easy to understand? Is it deliberate practice in writing, or did you put in other efforts, or is it innate?

Haseeb: To a large extent, it’s accumulated practice; after all, I’ve been teaching for so many years across different fields. Whether it was helping my mother adapt to life in America as a child or teaching others how to play poker when I was a poker player—I had done courses and one-on-one tutoring; then later, when I started programming, I found that the best way to master a new field is to learn first and then teach. There’s a learning hierarchy theory; I forgot the exact name, but I find it very reasonable: the worst way to remember is just reading; the retention rate of reading is very low; the second worst is listening; listening is a bit better than reading; the third is discussing; communicating and discussing with others can greatly improve retention; the most effective is teaching others. Teaching can greatly solidify your own knowledge, and I understood this early on. Teaching in different fields is actually also to make myself more proficient—why teach poker? Why teach programming? The answer is to become better at those things. In fact, while helping others, I gain even more.

The more you teach, the more you develop an intuition: you can distinguish whether the other person is just nodding along or truly understanding. Bad teachers seek "recognition" rather than "understanding." If you ask, "Do you understand?" no one will say they don’t. You have to make them explain it back to you. If you haven’t made the other person understand, that’s a failure on the teacher’s part. Additionally, teaching needs to be engaging enough for people to want to listen.

Luba: Are you currently learning something that you plan to teach others or are already teaching?

Haseeb: I’ve been learning in the crypto space. Additionally, I’m keeping up with developments in the AI field. I have a study group where we read a new paper each week, then present it to the other group members and try to explain what the paper is about, what the main findings are, what they accomplished, and what evidence they used to support it.

If you just read papers, you’ll find your eyes scanning the paper almost like running your hand along a wall, but that doesn’t mean you truly understand it, right? The way to really understand it is to answer questions, raise doubts, and identify the parts you don’t understand about the paper.

Luba: I have a limiting belief about my ability to teach. Two years ago, when we had a machine learning group, I also hated the day I had to present because I felt my understanding was too shallow.

Haseeb: That pressure forces you to notice your own motivations. When you’re forced to teach, you have to confront whether you truly understand it. If you don’t want to dig deeper, it indicates you don’t actually care about the topic; it’s a form of self-discovery.

Investing is a Bit Awkward

Luba: Speaking of self-discovery. You transitioned from poker to programming and then to Airbnb. But in your blog post, you mentioned that while you’re excited about web development now, you know it’s not a lifelong thing. What were you thinking at that time?

Haseeb: I knew I wanted to be an entrepreneur. Becoming a developer was the most logical step toward entrepreneurship because if you can’t build things, you need to have other skills to bring to the negotiation table, and at that time, I only had poker skills. My purpose for going to Airbnb wasn’t to get promoted but to learn how to build, meet partners, and build a resume that made people see me as capable.

Luba: When did you feel ready to leave? You left after just a year and a month. Right at the point of equity vesting. Was this planned from the start, or did you feel ready at that time?

Haseeb: It was basically planned. I thought if there was a chance for promotion, I might stay a bit longer, but I didn’t see hope at that time. So I thought, forget it, I’m leaving.

Luba: After leaving Airbnb, how did the whole transition into cryptocurrency happen? It seems like quite a leap. Airbnb is about belonging and cutting cake every week, while cryptocurrency is completely different.

Haseeb: Actually, it wasn’t that big. One of the members of the early fraud prevention team at Airbnb was Brian Armstrong, the founder of Coinbase. He integrated SiftScience. I remember seeing in the codebase, "If there’s an error, email barmstrong@airbnb.com." Later, I met Brian and the early Coinbase team through the "Risk Salon."

Luba: I’m one of the co-founders of the Risk Salon.

Haseeb: That’s right. After leaving Airbnb, I hesitated between AI and cryptocurrency. Ultimately leaning toward cryptocurrency because I felt AI was skewed toward people with traditional degrees and credentials (like PhDs), while I was a self-taught liberal arts person. In the crypto space at that time, there were no experts, no textbooks; everyone was self-taught, and everything was being invented in real-time. I liked that space filled with uncertainty. I entered when the market was hot. You know, the ICO bubble was happening. Everyone was excited. I thought, oh my god, I’m just a guy chasing fame and fortune, feeling like I arrived late. But in reality, no matter how early you enter any field, people always feel they arrived late. I remember a story about Marc Andreessen; he arrived in Silicon Valley around 1999. He said he was worried that by arriving in 1999, everything was basically over. The internet bubble was almost over, and there was nothing he could contribute. So people have always felt that way from the beginning. But it turns out, I think my decision to enter cryptocurrency was the right one.

Luba: Did Marc Andreessen have any influence on you?

Haseeb: I admire his vision; he invented modern venture capital through A16Z. But I don’t want to completely emulate him. His path is very different from mine. My background is quirky, and I took such a quirky path to get to where I am today; I can’t look at anyone else’s blueprint and say, great, as long as I do what they did, 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, where his competitors were all old-school, very different types of investors. I’ve heard many podcasts where he talks about how to build A16Z and how to invest, but his formula doesn’t apply today because it’s a different world, a different environment.

Luba: Speaking of forging your own path, you left Airbnb and decided to really dive into cryptocurrency. You founded a company, joined Bology with Earn, and then became an investor at Metastable. How did that transition happen from founding a company to playing the VC role? Why did you decide not to try founding a company again but instead choose this path? Was it Naval who truly convinced you, or was it entirely your independent principled thinking?

Haseeb: It was Naval Ravikant. The first time I met Naval, I was working on a startup, and we actually received an acquisition offer from a large cryptocurrency company, and I was consulting Naval and met him.

Luba: Not Coinbase?

Haseeb: Coinbase was one of the companies that wanted to acquire us.

Luba: I think Earn 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 was from Coinbase. So I initially met Naval to consult him on how to handle this potential acquisition conversation. He persuaded me, oh, you don’t want to join that company. I said, well, what should I do? That’s why I came here.

He said, if you get acquired by Coinbase, it will be boring. You’ll be working in compliance. Coinbase is run by lawyers. It will 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 the type of investor. I know nothing about finance. He said, it’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. What’s hard is judgment. Judgment is scarce, not investment knowledge. So he ultimately convinced me to become an investor, which is why I set aside my startup and turned to the investing side.

But at that time, I thought I wouldn’t be an investor forever. I thought I would be an investor for a while. I would make some money. But obviously, being an investor is a bit awkward. It’s not the coolest thing you can do. The real thing, the truly important thing, is to start a company. Obviously, I would do that; I would hang around for a while, and then I would go start another company. But what I didn’t know was that the place I would end up founding a company would actually be in venture capital.

Luba: Is investing still a bit awkward for you now?

Haseeb: Yes. Because venture capital is traditionally a very "elegant" profession; everyone takes summer vacations, doesn’t respond to messages on weekends, like a retirement job. I’m not that kind of person; I play games to win. Many small funds’ management fees allow partners to live very comfortably; they don’t need to engage in fierce competition. Even many partners at large firms are in that state. But Dragonfly is not like that; we are very aggressive.

Luba: But I think in the current VC deal competition being so fierce, it’s too hard to do that. There are so many VCs.

Haseeb: Of course. That’s why very few VCs are competitive. What do you think others are doing?

Luba: If you don’t treat it as a game to win, how can you make money through VC?

Haseeb: Understanding some of the economics of VC is important. First and foremost, many VC funds are smaller funds. If you raise $50 million and charge a 2% management fee, that means you have $1 million a year. This $1 million a year is not just your salary. It’s the total amount you pay for all salaries and any other expenses not covered by fund fees. So you hire people, hire a CFO, hire someone to handle investments, operations, etc. Maybe you can take home $500,000 a year. So a three-person fund with a $50 million fund is not a big fund. That’s a small fund. Many people can raise $50 million, hire two people, and take home $500,000. That’s a pretty decent salary for anyone. You can coast along; you don’t have to be very competitive; you don’t have to win every deal.

Luba: Then you’re most likely co-investing in deals rather than leading them.

Haseeb: Yes, you’re not leading; at this scale, you don’t have to compete for allocations with everyone. You can get some, but you’ll be excluded from most hot deals; Sequoia will win, A16z will win. But that’s not my concern. I’m not A16z. Even many partners at large firms are like that.

For me, the way I operate, I don’t play VC like that. The people at Dragonfly don’t play VC like that. If they think that way, then this place isn’t right for them. So that’s how I built this company. That’s why, although VC is awkward, I think the way we do VC is not awkward. But from the outside, you can’t tell the difference.

I’m Haseeb, and I’m Awesome

Luba: What made you decide not to start a company anymore and stay in the investment world?

Haseeb: I gradually realized that entrepreneurship 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 as an investor, it’s actually always interesting. Being an investor involves a lot of bullshit. But being an investor is actually trying to understand the world, holding views on the direction of the world, and the best way to prove yourself right is through the investments you choose. In a way, there’s no purer way to express your views on the future than through investing. I think I didn’t truly realize this until I achieved some success as an investor.

Then, after I left Metastable and ultimately built Dragonfly, what I realized most was that I really wanted to prove that I’m good at this. Because I didn’t stay long enough at Metastable to prove anything.

Luba: Who do you want to prove it to? Naval? Yourself? Or the world?

Haseeb: The main theme of my life is: I believe in myself much more than others believe in me.

When I wanted to learn coding, no one believed that a poker player without a CS degree could get into a top tech company. At Metastable, the suggestions I made later proved to be correct, but the partners at that time didn’t trust my judgment; they just didn’t want to do it. I talked to Paradigm, talked to Polychain. I wanted to join as a partner. Those companies either weren’t interested in me joining as a partner or said, well, maybe you can work your way up to partner step by step. I wasn’t sure if you really did that much. I thought, "Screw you; you don’t believe I can do it." To be clear, I had no evidence at that time to prove I had any ability. I wasn’t a big deal, didn’t have a big brand, didn’t have years of investment experience. I was a relatively new entrant in the cryptocurrency field. I had just started to understand it in the past year. So they had that reaction to me for various reasons, which was, why should I believe you can do it? What evidence do you have to prove you can do it? But I believed I could do it, of course. How could you not know who I am? I’m Haseeb. I’m awesome. I can definitely do it.

If I decide to do it, I’ll damn well do it. So, I believe in myself much more than others believe in me; I don’t remember a time when that gap didn’t exist.

Later, I met Bo and Alex from Dragonfly. Bo is a very intuitive person who trusted me almost immediately. He saw that I had ambition and was ruthless to win. He promised that if I joined, he would make me an equal partner. Bo had been a VC for a long time and was very intuitive. He’s very different from me. I’m more analytical and calculative. Bo is the complete opposite; he’s purely intuitive, purely social. He’s one of the best communicators and socializers I’ve ever met. He’s very good at things I’m completely not good at. And I’m the guy who hates birthdays, so Bo is the complete opposite. But Bo isn’t good at things like he doesn’t analyze, isn’t rigorous, isn’t calculative. And I’m very good at those.

Source: RootData

I think that’s a powerful factor in a strong partnership—not just that you respect each other, but that you can defer to each other in areas where you think the other excels. So when it comes to fundraising relationships, building interpersonal relationships, Bo is world-class; if we disagree, Bo is right. When it comes to technical analysis and underwriting, if Bo and I disagree, he knows I’m right, and he will defer to me. So, even though we are very different, from very different generations, there was an immediate, very, very strong and stable trust between us. That’s why I decided, okay, I can work with this guy.

Luba: How does this inform what you look for in teams and co-founders? For those 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 such people just requires a different way of working. I think it’s clear that teams being similar is more common than being different.

When you’re not different, it’s important that you truly trust each other in your respective areas of expertise. If there’s no such trust, like, "This person is great in this area, but I don’t really trust their ability in this area," or "I’m trying to undermine them in their area," then the real differences can be fatal.

So I think observing how teams collaborate is largely about looking at their dynamics, seeing how they interact, especially how they interact in uncomfortable or difficult situations. That’s why when I talk to teams, trying to assess them, I often try to put them in uncomfortable situations.

For example, if you’re founders and co-founders, and one of you is sitting here, I would ask, "So what is this person’s responsibility?" People often say, "Well, let him explain." No, I want you to explain what his responsibilities are. Then I want to see how he reacts to you explaining his responsibilities. Then I would ask him, "What are your responsibilities? Do you agree? Did he miss anything?" Just to see that interaction and how they respond to that interaction.

Another thing I often ask is, "How did you allocate equity?" You know, this is usually something people don’t like to talk about in front of each other, especially if the allocation is uneven. If it’s uneven, I really want to hear about it. So I would ask, "Why did you split it this way?" or "How did you allocate equity?" You know, the answer is often 50/50, but sometimes it’s not 50/50. Then I would ask, "Well, why did you decide to split it evenly? Don’t you think one person contributed more?" Then I look at their reactions to that question. Understanding how strong the trust is between these two people, what they each think the other excels at, and how much confidence they have in each other and each other’s answers is a big part of what I look for when assessing teams.

Luba: How does a person cultivate trust? For example, if they are inherently someone with trust issues.

Haseeb: If you have trust issues, don’t start a company, at least don’t find a partner. Entrepreneurship is not the place to solve your trust crisis. If you’re controlling and detail-oriented, it might be because you’re surrounded by unreliable people. But if you’re still like this in a top startup, then it might be your own anxiety issue; go see a therapist.

I Don’t Think I Think About "Greatness" That Much Anymore

Luba: I want to switch topics and talk about "meaning." You’re on the path to proving you’re a great investor, which takes time and clearly requires returns for the fund. Are you drawing meaning from this now? In your early personal blog, you talked a lot about meaning, just discussing things like "Will I have meaning in this world?" What were you seeking at that time? How has it changed since then?

Haseeb: At that time, in my early twenties, it’s hard to fully put myself back in that feeling, but I think what I wanted most was to become great at something. I don’t think it was about accomplishing a specific thing; it was more that I wanted to prove that the talents I was born with—my body, mind, experiences, abilities—could achieve greatness. In a way, it was my moral responsibility that if I had talents and abilities, I should cultivate them and do something with them. If I didn’t do that, I would be wasting them. I felt that deeply at that time, or at least I felt it deeply when I was young. If I wasn’t very talented, if I didn’t see myself that way, then I don’t think I would have that desire.

Luba: So, given that was your thought at the time, do you still believe that, for you personally, meaning lies in achieving greatness in something?

Haseeb: Yes, I think that’s still true now. Now I can think of it more in terms of excellence, mastery, and virtue. I don’t think I think about "greatness" that much anymore because I realize greatness is more about others. Greatness is a relative term, while excellence and mastery are more intrinsic. If no one agrees you’re great, you’re not really great. But you can be excellent; you can master a field, whether others know or acknowledge that you did. So, as I’ve grown older, this resonates more with me and serves as a foundation for my motivation. But there will always be some desire to prove myself to others. I think that will never disappear from me.

Luba: Is there anything wrong with seeking validation from others?

Haseeb: No, we are social animals. But that desire shouldn’t be the primary driving force; otherwise, it becomes pathological, like bulimia. You can’t pretend not to care about others’ opinions, but you can’t let it dominate you.

Luba: I saw a quote in one of your early blog posts that said, "I want to know if the book I write will have some value." That was about the poker book you wanted to write. "I want to know how people will remember me after I die. I want to know why I crave meaning so much." Very profound, touching the soul. But I think that was an exploration of meaning in adolescence. But I’m curious, how do you view legacy now? Is it as important to you as it was in your twenties?

Haseeb: I don’t care much about legacy now. In my early twenties, I wanted to write a memoir; now I think that’s silly. I don’t mind if no one remembers my name after I die; I hope the people I care about will care about me after I die. I don’t really care if others care. It’s just fine.

I care about Dragonfly. The legacy of Dragonfly is what will happen after Dragonfly disappears. I don’t know if I care about Dragonfly’s legacy. I care about Dragonfly while it’s still here. I want it to succeed; I want it to be respected; I want it to help those who work with it; I want everyone who works at Dragonfly to say Dragonfly is the best VC in the industry, and these are the people I’ve always wanted to work with. When Dragonfly is gone, when cryptocurrency ends, when I die, who the hell cares what others say? If someone remembers Dragonfly, it doesn’t matter. So many companies in world history will never be spoken of or dreamed of again, and that’s fine. They don’t need to be remembered.

Luba: To what extent should life be filled with enjoyment, and to what extent should enjoyment be secondary to the pursuit of greatness?

Haseeb: I prefer to use the term "flourishing" (Eudaimonia). Like a plant, it’s not just about having water and growing fat, but becoming its most complete version, reaching the highest complexity. This isn’t necessarily a happy process, but it’s about realizing all your potential. Society is too obsessed with pursuing simple "happiness" because it feels good. But becoming a great person, a reliable person to others, requires someone to tell you to pursue those values.

Luba: Talk about self-discipline. Do you still have those strict habits now?

Haseeb: I was more extreme in my early twenties. I would fast twice a week, only drinking water. I still do that now, although sometimes I drink tea or something. I used to strictly follow the paleo diet, avoiding sugar and starch. I had to prove to myself that I was disciplined through these "amulet-like" rules.

In high school, I would stay up late every night, sleep three or four hours, play computer games until late at night, and never do homework. I would do it before class and then sleep in class. I was a bad kid, a bit clever, barely scraping by with my natural intelligence. But I had no discipline. When I became a poker player, it got worse because poker can be played late into the night, and you’re surrounded by super unhealthy people; you’re very isolated because you don’t go to an office, you don’t have colleagues. It’s a very chaotic lifestyle. So I knew I wasn’t a disciplined person. When I started implementing many of these rules for myself, I stuck with them. For me, sticking to them was extremely important because it showed me that I could be that disciplined person. I think that’s more important than anything else; it might be the most important thing; it proved to me that if I could impose that level of discipline on myself, I could do it. If I could do that, then if I decided to do something else, I could do it too.

Luba: I think you’re going to a contemplative meditation retreat in a few weeks, which has become a routine for you every year, allowing you to set a vision for the next year and learn to solidify the lessons learned this year. Why did you choose this as a way to reflect on life?

Haseeb: I don’t know if I chose it or it chose me. We’ll see, but I accept it.

I mean, a silent meditation retreat is truly unparalleled.

It’s extremely isolating, maddening, and lonely. It forces you to confront anything you haven’t faced before, exploring every corner of your mind, every picture in your head, every door you haven’t opened in years. If you do a silent meditation retreat, you’ll face every question you haven’t given yourself the space or time to think about. Many of these are about what’s happening in life, relationships, the people you owe, the people you haven’t spent enough time with, the things you haven’t prioritized. There are also questions about your death, your childhood, your education, what you’re doing on this planet. Many of these questions you wouldn’t sit down and face every day. But if you give yourself enough time to be with yourself, you will face them.

So that’s why I do it. I find its clarifying effect is almost impossible to achieve through any other means.

Luba: So, is this your main way of setting goals and visions for yourself each year? Or do you have other methods?

Haseeb: Professionally, we set goals at a more regular pace. Personally, I sometimes do try to take stock and set goals, but almost always at the end of the year, often after a meditation retreat, I set these larger, more inclusive personal goals for myself. I try to ensure all my goals are measurable and very, very clear. So I will know if I’ve accomplished them. Not like "getting better at something"; you want to ensure your goals are clear, and you will definitely know whether you achieved them or not; you will know exactly what day it was.

Luba: To truly gain those benefits, how many days do you recommend going on a retreat?

Haseeb: I recommend at least four days. If it’s less than four days, that desperate feeling isn’t strong enough. You almost have to traverse the dark valley.

Lightning Round

Luba: Now we move into the lightning round. What life insight have you gained that is now obvious to you but not to others?

Haseeb: Money doesn’t make people happy.

Luba: What do people waste the most energy on?

Haseeb: Worrying about catastrophic outcomes that are unlikely to happen (Catastrophizing).

Luba: Who is your current mentor?

Haseeb: I think it’s mainly Naval. Before that, it was Ned Ruggeri at App Academy. He was my mentor. He taught me a lot. Besides them, I haven’t really had many mentors.

Luba: Do you have a dream mentor?

Haseeb: A dream mentor? I can’t think of one. I have people I admire and respect, people I enjoy spending time with.

Luba: Three must-watch movies?

Haseeb: The first is "Parasite," the second is "Samsara," and lastly, maybe "American Beauty."

Luba: Do you still feel like you haven’t figured something out?

Haseeb: I haven’t figured out what drives the animal spirits in the market to change. I haven’t figured out… I haven’t figured out why society is moving away from liberal values toward libertarianism? I haven’t figured out why people so easily forget the things they recently believed in? Many of these things are still very counterintuitive and surprising to me. Like, the way individual behavior changes in groups and society is still a bit of a mystery to me.

Luba: Is cryptocurrency really happening?

Haseeb: Cryptocurrency is definitely happening. It’s happening damn well.

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