Author|When Shift Happens
Translator|Yuliya, PANews
In the field of cryptocurrency investment, finding the next hundredfold return opportunity is every investor's dream. As a top global cryptocurrency investment fund, Dragonfly is known for its unique investment vision and deep technical understanding, with a portfolio that includes numerous star projects such as Avalanche, Near Protocol, Monad, and Athena.
In this episode of When Shift Happens, Dragonfly managing partner Haseeb Qureshi shares his legendary journey from professional poker player to top cryptocurrency investor, and how to establish a lasting impact in this rapidly evolving industry. This episode covers the most critical topics in cryptocurrency investment: how to turn cryptocurrency into a team sport, why money can't buy happiness, how to deal with impostor syndrome, and common mistakes made by new investors. PANews has provided a written translation of this podcast episode.
Personal Background
Haseeb: I am Haseeb Qureshi, currently a managing partner at Dragonfly Fund, a global cryptocurrency investment institution managing billions of dollars in assets. Speaking of my career, it has been quite dramatic: starting as a professional poker player, transitioning to a software engineer, then becoming an entrepreneur, and finally entering the VC industry for over six years. Among all my career experiences, cryptocurrency investment, while the most challenging field, is also the one that feels the most valuable and meaningful to me.
Host: What prompted you to ultimately decide to give up your poker career?
Haseeb: It was a very chaotic time. I had built quite a reputation in the poker world, but my reputation took a severe hit due to an incident involving cheating by my students. At the same time, I was growing increasingly tired of poker. I didn't want to look back at 50 and realize that my life had been about playing cards and winning money from others. That wasn't the meaning of life I wanted.
I made a radical decision: I left myself with only $10,000 for basic living expenses, donating the rest or giving it to my parents as retirement funds. I wanted to force myself to start over. At that time, I was 23, and I went back to school to study non-technical subjects like English and philosophy. Being the oldest student in the class, with nothing on my resume except "professional gambler," was indeed panic-inducing.
This decision gave me a new perspective. As a software engineer in Silicon Valley, my annual income was about $100,000, much less than when I was playing poker. But interestingly, my sense of happiness didn't change much. What truly brings satisfaction is learning new knowledge, achieving personal growth, and establishing genuine connections with those around me.
Differences and Similarities Between Poker and VC
Host: Transitioning from a professional poker player to a venture capitalist is a significant shift. How do you view the similarities and differences between these two fields?
Haseeb: The most fundamental difference between venture capital and poker lies in the length of the feedback cycle.
In poker, the correctness of a decision can be validated in a very short time. For example, when you judge that an opponent is bluffing and choose to call, the result is revealed immediately.
In venture capital, however, the situation is entirely different. The quality of an investment decision often takes six to seven years to truly clarify. As we often see, a startup may seem to progress smoothly from seed round to Series A, but could suddenly face a fatal crisis in Series C. This delayed feedback mechanism places extremely high demands on an investor's judgment. It is worth mentioning that it is precisely through rigorous judgment that we successfully avoided projects like FTX, BlockFi, and Luna, which ultimately collapsed.
Host: It sounds like the feeling of making the right judgment is also quite different?
Haseeb: Indeed. This difference is very pronounced. In poker or trading, the rewards of making the right decision are immediate and intense, producing a direct dopamine rush. The sense of achievement from "I won" is very immediate.
But in venture capital, success is a gradual process. It is more like nurturing a tree: there are no dramatic climactic moments, but rather a need for continuous patience and investment. You see a startup growing step by step: each round of financing brings a steady increase in valuation, continuous improvement in operational metrics, and a collaborative search for solutions when challenges arise.
This process requires investors to possess strong patience and persistence. Unlike the quick win-lose judgments in poker, venture capital is more like a marathon, testing long-termism and the ability to create sustained value. It is this gradual growth process that makes working in venture capital particularly meaningful.
Investment Judgment
In venture capital, judgment about people is often more critical than analysis of business models. While investment giants like Naval Ravikant or Chamath Palihapitiya often emphasize breaking stereotypes, the actual judgment process is much more complex. As an experienced investor, I find that there is an important paradox embedded in this.
Junior investors typically need to undergo a cognitive process: understanding that analyzing business models and technological innovations indeed requires continuous learning and in-depth research, often needing to build a systematic analytical framework through studying the history of technology and business. Interestingly, however, understanding human nature is an innate ability we possess.
Our nervous system is naturally equipped to interpret others. When you feel distrust towards someone, even if you can't pinpoint a specific reason, that feeling often stems from the many subtle signals you have received.
However, junior investors often overlook this intuitive judgment and instead rely too heavily on surface evidence:
· "Maybe it's my lack of experience, and my judgment isn't accurate."
· "This founder has an impressive resume, and the business plan is well-structured."
· "He has so many well-known partners backing him."
As you gain experience, you gradually realize: you need to learn to trust your intuition. The key is to see through the surface social validations and perceive a person's essential characteristics, considering the choices they might make under pressure, uncertainty, and moral dilemmas. In most cases, your first intuition is often correct.
Stereotypes
Venture capital is essentially a people-oriented industry. Although the field of social psychology faces a "reproducibility crisis," the "accuracy of stereotypes" is one of the most robust research findings. For example, when you feel that highly aggressive people often lack reliability, that judgment is usually accurate.
The human brain is a system that continuously engages in statistical learning. Although contemporary culture tends to deny stereotypes, they can indeed be positive, negative, or neutral. For instance, the stereotype that "Asians prefer rice" is neutral and statistically accurate.
Investment Motivation
Host: What drives you to continuously engage in these yet-to-be-fully-explored fields?
Haseeb: Essentially, the fields I am involved in, whether early poker or now cryptocurrency, have two notable characteristics: high chaos and creativity. This fundamentally differs from traditional linear development fields. For example, quantitative analysis on Wall Street is essentially an intellectual competition; whoever has the higher "score" can earn more returns.
In emerging fields like cryptocurrency, it feels more like exploring an unknown continent. Here, not only is exceptional intelligence required, but also the courage to take risks, the ability to innovate continuously, and the insight to integrate multidimensional information. It is this challenging environment that keeps my enthusiasm alive.
There is no so-called "nobility" in the crypto industry. Unlike traditional VC, you don't need a prominent background or a vast network, nor do you need to have experience founding billion-dollar companies. Genuine effort and continuous dedication are the keys to success.
A bear market acts like a mirror, clearly showing who comes with sincere intentions and who persists quietly. Each bull market attracts a batch of successful Web2 entrepreneurs with substantial funds, but those who ultimately remain are often those considered "alternative" or "crazy," as they are the ones who truly build valuable projects.
Some Thoughts
Structured Learning
Host: Can you talk about your understanding of learning methods?
Haseeb: I believe learning can be divided into two types. The first is structured learning, and the other is unstructured learning.
Structured learning is characterized by a clear learning path and tool support. Taking chemistry as an example, it has a complete textbook system and accompanying learning resources, allowing learners to follow a predetermined path step by step. The key to this learning model lies in cultivating self-discipline and focus. In fact, most of the training we receive in the traditional education system is of this type. However, the real world often does not care about your structured learning outcomes. When you finish college and go directly to work, you quickly realize that almost everything you learned in school is not applicable. The education system is more like a qualification certification process, proving that you possess the basic qualities to receive professional training.
In real professional environments, especially in high-value-creating positions, there are often no ready-made manuals or training materials. You cannot prepare systematically like you would for an academic exam. This requires practitioners to continuously explore and learn in unknown fields, even if there are experts in the field, they often do not have enough time for systematic knowledge transfer.
Host: Can you provide an example of how unstructured learning is applied in practice?
Haseeb: I encountered this learning method early on. When I started playing poker in 2006, there were very few educational resources in this field. Although there were some books, they were not good enough. If you wanted to become a world-class poker player, you could only gather scattered information from blogs, forums, and videos. You had to self-learn, experiment, and take risks, investing your own money, learning from failures, and iterating continuously.
The cryptocurrency field was similar six or seven years ago. At that time, there was only "Mastering Bitcoin" and a textbook from Princeton (authored by one of the co-founders of Arbitrum), with only a few lines about Ethereum in that book. To learn this content, you had to dive into practice, communicate with those at the forefront, create your own curriculum, and iterate continuously.
This unstructured learning is often the most valuable and yields the highest market returns. Those who can master this learning method typically receive the highest rewards, which is precisely what school education has not taught us.
Money Can't Buy Happiness
Host: You previously mentioned that "money can't buy happiness." Can you elaborate on that?
Haseeb: I started playing professional poker at 17, and at that time, I met many young wealthy people, but they were all very unhappy. In the poker world, you see people in their twenties worth millions, buying luxury cars and watches, but no one cares. If you buy these things just to gain status symbols and not for genuine enjoyment, it is meaningless. Money can indeed solve your financial problems, but research shows that once income exceeds a certain level (for example, $50,000 to $100,000 per year), the increase in happiness sharply declines.
People's happiness comes more from personal progress, growth, and connections with others—friends, family, and interpersonal relationships. This may sound like a cliché, but it is true.
Effective Altruism
Host: What are your thoughts on the effective altruism (EA) movement?
Haseeb: I started getting involved with EA after leaving poker, around 2012-2013, when the movement was just beginning. During the FTX era, EA became quite "cool," which made me a bit uncomfortable because EA is essentially a very alternative idea. Now, with the collapse of FTX, the situation is completely the opposite.
Now we are in a bear market for EA, which is somewhat healthy. When EA was "cool," people would question the motives of those who joined. But now, those who claim to be EA are the ones being questioned, which can actually test people's genuine beliefs in these ideas. Just like with cryptocurrency, the failure of FTX does not affect my belief in cryptocurrency because FTX represents centralization and third-party trust, which is completely contrary to the core values of cryptocurrency.
Host: How do you handle public misunderstandings about these fields?
Haseeb: This involves the distinction between philosophy and politics. Most ordinary people may not delve into the details and are prone to misunderstandings. This indeed makes work in the EA or cryptocurrency fields more challenging, but it is important to stick to core principles and values.
Views on Cryptocurrency
Host: Do you have any unique insights into the essence of cryptocurrency?
Haseeb: The core of cryptocurrency is a philosophy. It raises a fundamental question: should the flow of value and funds be freely controlled by individuals, or should it be controlled by the state? The depth of this question far exceeds the actions of some Bahamian businessman.
I did not enter this field out of a belief in liberalism. In fact, I am not even sure whether cryptocurrency will ultimately benefit the world. It may bring more chaos: weakening state control over monetary policy, increasing the risk of hacking, especially in the AI era, where uncensored and unstoppable flows of funds could have terrifying consequences.
But the key is that the development of cryptocurrency is inevitable. Just like social media, regardless of whether people think it is good or bad, it has already become a part of reality.
Host: You mentioned that cryptocurrency is very different from other technologies?
Haseeb: Yes, that is what makes cryptocurrency unique. Over the past 50 years, most technological innovations have reinforced state power. Think about the internet and artificial intelligence; they have all, to some extent, enhanced government control.
But cryptocurrency is fundamentally disruptive. Just as YouTube disrupted the monopoly of traditional television stations, cryptocurrency is creating "user-generated money." If money were inherently free and programmable, we wouldn't need cryptocurrency at all. Its existence is a response to government restrictions.
Most people believe that technology should ultimately be "tamed" by the government. But what is unique about cryptocurrency is that its core value lies in not being tamed. This makes many people uncomfortable, which is why some try to discuss blockchain technology separately from cryptocurrency.
If we look at what Snowden revealed, we find that the internet has actually enhanced government surveillance capabilities. In contrast, cryptocurrency may be the only significant technological innovation in the past 50 years that truly serves individuals rather than the state.
Keys to Success
Host: Can you share some key principles for achieving success in the cryptocurrency field?
Haseeb: The primary principle is to enhance your technical understanding. While everyone's technical level varies, cryptocurrency is essentially a technological innovation. Without understanding the technology, you cannot build a robust mental model to predict the direction of the industry. You don't need to become a top smart contract developer, but you should at least understand the basic workings of programs and computers. This way, you can judge what is feasible and what are false promises. Improving technical understanding is always the right choice in this field.
The second important principle is to start writing and sharing publicly. Many people feel they have no new ideas and want to wait until they accumulate enough knowledge before they start sharing, which is a huge mistake. I started blogging as soon as I got into cryptocurrency. Looking back at those early articles, they were indeed quite naive, but that doesn't matter. Because:
· No matter what stage of learning you are in, there will always be someone who needs the foundational knowledge more than you.
· The fact that no one paid attention early on is actually a good thing, as it gives you space to practice.
· Improving by 1% every day leads to astonishing accumulation after a year.
Advice for Newcomers
Host: What is the most counterintuitive fact for new investors?
Haseeb: The most important thing to realize is that almost all significant cryptocurrency projects are created by crypto natives, not by elites from Google or Harvard. Whether it's Ethereum, Uniswap, or other important projects, they are all created by "eccentrics" deeply involved in cryptocurrency. These people may seem "too obsessed with the internet," but it is precisely they who have built the most important projects.
Host: So, how does one become a crypto native?
Haseeb: The key is to find your unique advantage. Don't try to completely transform yourself into another Vitalik or learn complex zero-knowledge proofs. Instead, you should:
· Clearly identify the area you excel in.
· Maximize that advantage.
· Find the crypto projects or people that need that skill the most.
· Prove your value through practical actions.
It's like entrepreneurship; don't mimic someone else's path, but find a unique positioning based on your strengths. Don't think about "how to get that cool person's job," but rather "what value can I bring to this industry?"
Host: This sounds very much like an entrepreneurial mindset?
Haseeb: Exactly, it is completely the same as entrepreneurship. When you are starting a business, you ask yourself: what am I good at? What problems can this skill solve? You choose areas you love and excel in, rather than blindly trying to do the next Uber. Similarly, in career development, don't try to replicate someone else's career path; instead, plan your path based on your strengths and weaknesses.
Followers ≠ Influence
Host: When I first started managing Twitter, I thought the number of followers equated to influence. But later I found that many high-follower accounts are actually just "content farms," which, while having high engagement, have little actual influence. Interestingly, true industry leaders often have relatively few followers. This is actually a phenomenon known as the "Buton Paradox": in extreme cases, two originally related factors (follower count and influence) can diverge. Can you explain this in detail?
Haseeb: This is a phenomenon that many people can intuitively feel. Accounts with millions of followers may indeed be good at creating content and entertainment, but when they genuinely want to push something to happen, they often cannot achieve it. For example, an account with 5 million followers may want to drive up the price of a certain coin, but no one responds.
In contrast, some accounts with fewer followers can draw the entire industry's attention once they speak up. For instance, Bow, a partner at Dragonfly, is very low-key on Twitter and doesn't even have a social media account, but he is a highly influential figure in the industry.
The Development Curve of Influence
This phenomenon tells us two things:
- You cannot use social media attention to judge influence.
· Many people admire high-follower accounts, believing they must be influential.
· But in reality, the actual influence of many high-follower accounts is limited.
· This often leads the owners of these accounts to experience a moment of "awakening."
- The relationship between follower growth and influence is nonlinear.
· When growing from 200 to 2,000 followers, you can indeed feel a significant change.
· But when growing from 50,000 to 100,000, the actual influence may not change much.
· This indicates that after reaching a certain critical point, the returns on further investment in follower growth are very low.
Host: So, how do you truly build influence?
Haseeb: Many people think that building influence in the cryptocurrency space is about self-promotion, flaunting connections, or quickly cashing in on pre-sale projects. But in reality, the true method is:
· Create value for the industry.
· Help founders solve problems.
· Do meaningful things behind the scenes.
· Provide value in every interaction.
This is indeed much more challenging than simply posting, which is why most people cannot truly build influence—because most people are takers rather than givers.
VC Experience and Reflection
The cryptocurrency industry attracts a wide range of participants, from day traders seeking short-term gains to professional hedge fund practitioners, innovative project entrepreneurs, and venture capitalists supporting innovation. This industry often exhibits characteristics of a zero-sum game, much like a "player versus player" (PVP) game. Long-term participants may face mental challenges, easily falling into a cynical mindset, succumbing to nihilistic thinking, and lingering in periodic false booms, bearing the psychological pressure of rapid monetization.
However, venture capital plays a unique role in this industry; it is essentially a zero-sum game. VCs drive team success by discovering talented individuals and providing necessary support. The success of VCs entirely depends on the success of entrepreneurial teams, and this close alignment of interests transforms what was originally a "single-player game" into a "multiplayer game." This not only creates greater value but also provides practitioners with a healthier mindset and development model. This collaborative approach may be the best way to engage in this disruptive and significant industry.
Impostor Syndrome and Self-Perception
Host: During your transition, did you experience impostor syndrome?
Haseeb: Yes, that feeling has always been there. I think if someone completely lacks this feeling, they are either not thinking deeply enough or lack self-reflection. The key is not to overcome this feeling but to learn to coexist with it. When I first became an investor, this feeling was particularly strong—"I have never created a successful company; why should I give advice to others?" But interestingly, it is precisely this "outsider" perspective that allows me to see problems that founders may not notice.
When you offer advice as an investor, it often receives special attention. For example, a company may have obvious issues, such as poor marketing strategies or product positioning, which everyone internally can see, but the founder may overlook. Yet when an investor—even a relatively inexperienced one—offers the same advice, it often gets the founder's attention.
This "magic" partly comes from the investor's external perspective, unaffected by the "gravitational field" of the company. For instance, Polygon was operating six different product lines at one point, and I told the founder, "You have too many product lines; the market will find it confusing. You need to simplify the product lines to make the story clearer." This suggestion received a positive response, even though I may not have been the only one to make it.
Success vs. Failure
Host: In venture capital, what is the biggest "success moment"?
Haseeb: To be honest, there is no such thing as a "big breakthrough moment." VC is a day-to-day, continuous accumulation process. Even when you receive a check at the exit of a project, that feeling is more like "finally arrived" rather than "wow, unbelievable." This characteristic makes VC healthier than other forms of investment.
Host: How does it feel to make mistakes? Can you share a specific example?
Haseeb: In the VC industry, the biggest mistake is often not making a wrong investment, but rather missing out on good projects. This is because VC follows a power law distribution, and missed opportunities can be more fatal than failed investments.
For example, my biggest regret is missing the Series A funding for Uniswap. At that time, we analyzed all the data:
· Profitability of liquidity pools
· Trading volume
· Advantages and disadvantages of the pricing mechanism
Our analysis was "smart" and "correct," but we completely missed the most important point: the revolutionary innovation brought by Uniswap—an entirely automated system that allows anyone to list and trade any asset.
The Eternal Dilemma of Investment
Haseeb: As an investor, you will never be completely satisfied because:
· You either regret missing a good project
· Or you regret not investing more
· Or you worry about selling too early or too late
But this discomfort is normal and even a good thing. If you feel too comfortable, it might actually be a dangerous signal.
As a VC, I have become relatively calm about timing the market exit. The key is to understand:
· Don't pursue the perfect exit timing
· Set reasonable goals: for example, exiting within 40% of the peak is very successful
· Overly pursuing precision can be dangerous and may lead to missing the entire cycle
· It is impossible to accurately time the bottom or the top.
Maintaining Public Image
Host: As a public figure, how do you cope with the drastic changes in external evaluations?
Haseeb: This is indeed challenging. Take the example of 2021-2022, when the overall image of the cryptocurrency industry underwent a huge transformation. Especially after the collapse of FTX, the entire industry was affected. Due to my association with effective altruism, I was also impacted after FTX's collapse. Suddenly, you are no longer invited to parties, and people are reluctant to connect with you.
As a venture capitalist, how others perceive you is indeed important because that is your business. But I have found that the best way to deal with this situation is to:
· Stay transparent
· Speak your true thoughts
· Continuously create value
In this industry, you will inevitably offend some people. I have annoyed: the Solana community, the Cardano community, and other major project communities. But there is a characteristic of this industry: memories are short. For example, I once wrote a critical article about the EVM (Ethereum Virtual Machine), and at that time, the Ethereum community was very angry with me. Now, many people actually consider me an Ethereum maximalist.
When facing controversy, you can ask yourself: "Is this a battle I truly care about?" If not, delete the controversial content and move on. In this fast-paced industry, there is no need to get caught up in every controversy.
Future Outlook
Host: Looking ahead to the next 12 months, what are you most focused on?
Haseeb: From a macro perspective, the market direction will largely depend on the Federal Reserve's policy moves. The institutionalization of cryptocurrency is an irreversible trend, but this process will be relatively gradual and unlikely to experience dramatic fluctuations.
It is worth noting the shift in institutional attitudes. Take BlackRock as an example; from 2019 when we were still striving for their recognition, to now when they have become active advocates for Bitcoin ETFs, this shift is quite significant. The progress made in institutional recognition of the cryptocurrency industry over the past five years has far exceeded the perceptions of many market participants.
Based on the current market environment, I expect the growth trend in the next two to three years to be more rational. However, it should be noted that the cryptocurrency market has its uniqueness, and once it enters a new market cycle, the market direction may break conventional expectations. This shift could stem from adjustments in risk appetite or changes in the interest rate environment. Overall, I hold a cautiously optimistic view of the cryptocurrency market, but I expect the volatility to be less than that of the 2021 cycle.
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