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This article outlines the career journey and trading insights of renowned cryptocurrency trader Eugene over the past 3-4 years. After nearly going bankrupt in 2021, he transitioned to investing and founded Tangent Company. He emphasizes risk management, concentrated positions, and teamwork, believing that survival comes first and that one must adapt to the market and learn from mistakes. His trading style focuses on finding asymmetric opportunities and building proprietary frameworks. He has methods for handling psychological issues and insights on bet sizing. He also shares past investment experiences, including success and failure cases. His goal is to build a proprietary fund to support causes like space exploration and advises newcomers to focus on on-chain assets and to give back to society after achieving success.
Editor’s note: This article outlines the career journey and trading insights of renowned cryptocurrency trader Eugene over the past 3-4 years. He grew from the setbacks of nearly going bankrupt in 2021 to founding Tangent Investment Company, focusing on liquidity markets and long-term strategies. Darryl emphasizes the importance of risk management, concentrated positions, and teamwork, advising newcomers to focus on on-chain assets and to be patient. He also hopes to leverage cryptocurrency success to support causes like space exploration, encouraging traders to pursue success and give back to society.
Many people know Darryl (renowned trader Eugene) has an account on X called 0xENAS, where he frequently shares trade logs, monthly reflections, and market insights. He is one of the best cryptocurrency traders in the world, but his journey has also been filled with ups and downs. After nearly going bankrupt in May 2021, he successfully transitioned to being an investor and built one of the most prestigious funds in the field.
Since 2022, I have had multiple conversations with Darryl on my YouTube channel and I hope to transcribe those insights and learnings that have been most helpful to my trading. He is one of the sharpest minds in the field, and I hope this content will be helpful to you as well.
The Journey of Trader Eugene
For those who aren’t familiar, can you share what you’re working on now?
I co-founded Tangent, a multi-strategy principal investment firm where I focus on liquidity markets, while my partner Jason handles venture capital. We also manage a spot portfolio focused on long-term fundamental strategies. Previously, I was the head of Defiance Capital. I entered the cryptocurrency space as a retail investor in 2020, but I’ve grown a lot since then.
You’re now a very successful trader, but I remember you faced some setbacks in 2021. Can you share your mistakes and what you learned from them?
In early 2021, I was completely in a high-risk state, actively using leverage. I made some profits in February, but then jumped back in March—the result was I failed to avoid the crash in May. Due to overexposure and trying to bottom-fish with leverage, I suffered an 80% drawdown at the worst moment, forced to de-leverage core positions at the lows. It was brutal, but it taught me the most important lesson: survival comes first.
I cut my losses and restarted. A significant mistake was over-allocating to a single DeFi protocol that never recovered after the downturn. That loss reinforced the necessity of diversification, no matter how strong my conviction.
The key is to stay in the game. No trade should bankrupt you. Adaptability, risk management, and learning from mistakes are crucial for long-term success. Even today, when we determine the size of our bets, minimizing the risk of bankruptcy is our top consideration.
How has your trading style evolved?
The first step is to understand how you should position yourself—look for asymmetric opportunities with significant upside potential. The harder part is identifying these opportunities in real-time. There’s no crystal ball; it comes from experience, trial and error, and developing intuition.
For me, cryptocurrency still feels very intuitive. When I see a new opportunity, I usually have an instinct about it within minutes, and over time, I've learned that my initial instincts are often correct. Looking back, I try to analyze what triggered that intuition—what specific factors gave me confidence in an investment. These patterns often repeat. While the market is constantly changing, the biggest winners tend to share similar characteristics. Over time, we've built a proprietary framework at Tangent to help crystallize and quantify these traits so that we can better identify them in the future. These frameworks have been immensely helpful in improving accuracy and allowing others in the company to draw from my experiences in the market.
How do you handle psychological issues in trading?
Yes, it’s a big challenge. In a 24/7 market like cryptocurrency, you’re constantly battling emotions of greed, fear, and the feeling that someone will sell you out. Keeping a clear mind is crucial. If I feel my emotions are getting the better of me, I take a step back. Sometimes, I’ll completely step away from cryptocurrency for two to three days to reset.
One key lesson I learned is that you can’t seize every opportunity. You have to accept that you’ll miss certain chances. I stick to my area of expertise. Recognizing your strengths and ignoring distractions is key to long-term success. As GCR once said, 'He who chases two rabbits catches neither.'
How do you view the scale of bets?
I believe in concentrated positions. Sometimes we put 80% of the portfolio into our three best ideas. It’s about aligning your portfolio with your most confident bets. The key is to ensure that your position sizes match your level of confidence. Of course, this also means you need strict risk management to avoid massive drawdowns.
How do you explore direction in the internal struggle of wanting to avoid risk while also wanting huge returns?
That's a tricky question. In the first cycle, I took on massive risks—like putting 80% of my net worth into a single asset. While that sounds ridiculous in hindsight, that bold move brought significant returns. Now, as an investor in the second cycle, I’m more cautious, but I still ask myself: what allowed me to make those bold moves before, and how can I replicate those moves now without being reckless? The challenge is to take risks while maintaining the belief I had before, all while being realistic about market volatility.
Past investment experiences
I remember you put 80% of your net worth into AVAX in 2021. Looking back, if given the chance, do you think you would make the same decision again?
This is a difficult question to answer. In hindsight, it seems ridiculous, but that risk exposure allowed me to achieve significant compounding returns. Today, I ask myself if I can still do the same thing. As I’ve matured, I’ve gained a greater awareness of risk and developed a completely different system and framework to prevent major mistakes. Back then, I was more naive, and I believe that mindset played a huge role in my success in the previous cycle. It’s important to be aware of risk, but when the market presents you with opportunities, dare to dream.
So, you’re saying that your current approach is more cautious, but you still need to be able to take on the same risks to achieve those outsized returns?
That's right. While it feels daunting, understanding that you need to make big, concentrated bets is crucial. It's difficult, but the best cycle returns come from this. You must be willing to take those risks, even if they make you uncomfortable.
It sounds like you've built a lot of discipline over the years. Can you share an example of a bad trade you made and what you learned from it?
I’m human too, and I make mistakes often. A recent trade that left a scar was when I over-leveraged $SOL at $210 and didn’t respect my stop loss at $200. The most important lesson in trading is to control downside risk, and to enjoy that limited downside risk, you must execute stop losses. Once you become careless in this regard, mistakes can accumulate in more dangerous ways, and you might be taking on far more risk than you initially planned.
What would you say to your past self?
I ask myself, 'If you sold your entire portfolio today, would you buy back the same assets in the same proportions?' Most people realize they wouldn’t, but they still hold onto poor positions due to emotional attachment. Additionally, opportunity cost is important—every dollar invested in one asset is a dollar not invested elsewhere.
Another thing is to avoid the mentality of 'making back everything in one trade.' This is a common trap. Instead of revenge trading, focus on compounding small victories.
How do you know when to close a position?
This is the hardest part. Many people hold onto losing positions because they are emotionally attached or simply hope things will get better. But the key is to be honest with yourself. If you’ve re-evaluated your thesis and things haven’t improved, it’s time to let go. This is something many retail investors struggle to cope with.
How do you avoid mistakes?
How do you ensure your biases don't affect your judgment?
Having a team definitely helps. In my company, we keep everything transparent, so when I make questionable decisions, people can point them out. Accountability keeps me vigilant. We conduct rigorous and often brutal post-mortems on every major decision and encourage everyone, including new hires, to point out issues with more 'senior' members of the company in an extremely transparent manner. There’s no room for arrogance in the market, and it’s crucial to build a team dedicated to complete honesty without emotion. If you’re trading solo, find someone to share your positions with and get feedback. This helps mitigate emotional decisions.
So, accountability plays a huge role in keeping you focused?
Absolutely. Having a team or even a trusted person to discuss trading can ensure you don't get stuck when things go wrong. If you make a mistake, it’s important to acknowledge it and move on rather than digging yourself into a deeper hole. This accountability can prevent you from making more mistakes.
Can you share an example of how this has helped you avoid a mistake?
Of course. I once shorted a significant amount of Dogecoin during a market event that I thought would trigger a sell-off. One of my team members questioned my decision, and instead of doubling down, I paused to reflect and realized that the position didn’t make sense. This transparency and honest feedback allowed me to cut my losses early and reassess. If I had been operating solo, I might have stuck with that position and watched my losses grow.
What advice do you have for those looking to find their trusted group or circle of participants?
A lot of alpha has already shifted from Crypto Twitter/X to Telegram chats and Discord communities. Twitter/X is a great platform for those just starting to build an online presence and share ideas, but today I prefer Telegram channels as my primary means of communication.
What common traits do successful traders share?
Let’s change the subject. Who do you admire in the market?
I saw a tweet from Stanley Druckenmiller that resonated with me. He mentioned that we should compete with the opportunity set, not with the benchmark. If you perfectly seize an opportunity, you’re just meeting expectations, not exceeding them. You’re really competing with yourself, improving over time. The goal is to minimize mistakes, and if you do that, you will naturally become a better trader or investor over time.
What common traits do successful traders share?
Successful traders are very good at handling stress. When the market is volatile, they can make decisions without panicking. This isn’t something that can be easily learned—it’s a natural skill. If you have this ability, hone it. If not, recognize that and don’t force yourself into high-pressure environments. It’s crucial to recognize your strengths and weaknesses and choose a position that suits you accordingly.
What are the most common mistakes traders make?
I often see people celebrating prematurely before things have materialized. This happens when people get caught up in the 'I’ve made it' mindset due to portfolio gains, and they start making significant lifestyle changes. They think that the money on paper is real money, and then go out and buy things they don’t need, like expensive cars or luxury watches. But the reality is, money isn’t real until it’s in your bank account and you’ve paid your taxes. I always view cryptocurrency this way—it’s a game until it turns into cash. When people don’t understand this, they often mismanage their wealth and lifestyle.
Advice and Expectations
What are some common misconceptions people have about cryptocurrency?
One of the biggest misconceptions is that you should allocate capital based on fundamentals. People assume that if a project has strong fundamentals, the price will rise accordingly. But in reality, the market doesn't care about fundamentals 90% of the time. Real profits come from predicting which narratives will become popular before others do. Fundamentals matter when there are catalysts, but most of the time, the key is to catch the next trend and increase your position when you see it. At least that's my experience. It's a bit like knowing something is about to happen, and then it suddenly does—you grab it as much as you can because the speed and magnitude of market movements can far exceed your expectations.
What advice would you give to someone entering the cryptocurrency space today to succeed?
Honestly, if I were entering the cryptocurrency space today, I would question whether it’s worth it. But if you still want to enter, I would say a few things: First, focus on on-chain assets. They are the assets with the greatest upside potential and can provide the fastest compounding growth for smaller portfolios. But the on-chain market won’t last forever—on-chain assets have specific seasons, and when those seasons end, you need to be able to trade on centralized exchanges. The ability to trade in both arenas is crucial, but I would focus on mastering one and becoming proficient in the other, rather than trying to master both at the same time.
You’ve been in the cryptocurrency space for a while. What are your personal goals for the next 10 years? Do you think cryptocurrency is just a means to an end?
First of all, I absolutely love this game. Competing with the best traders and investors in the world is one of the main reasons I entered this field. In the next 10 years, my goal is to build the best proprietary fund in the cryptocurrency space. Long-term, my sights are set on the stars.
I have always dreamed of contributing to humanity's progress to interstellar species. A large part of that is supporting space exploration in any way possible. One of my bucket list goals is to go to space before I die.
Wow, that's incredible. So, do you think cryptocurrency is more than just wealth accumulation—it’s part of a broader vision?
That's right. A lot has been said about the mission of cryptocurrency, and I don't need to repeat it here. For me, beyond that, cryptocurrency is a platform for achieving extraordinary wealth, giving us the opportunity to compete globally. I hope to leverage this success to support larger causes, such as biomedical research, space exploration, and environmental conservation. In my company, as well as through personal investments with my co-founders, we have actually invested in robotics, biocomputing, home cancer detection, and cutting-edge technologies related to or interested in cryptocurrency. Sometimes the founders are even former cryptocurrency practitioners or interested in cryptocurrency. All of this is interconnected.
What advice do you have for those who want to succeed in the cryptocurrency space right now?
My motto is simple: 'Live, Laugh, Long.' 'Live' means taking care of yourself and enjoying life while you're young. 'Laugh' means appreciating where you are and making the most of every moment. 'Long' means being patient, understanding when to allocate resources, and knowing where you want to contribute. If you live with this mindset, you’re not only contributing to society, but you’re also planning for the long run. That’s how you succeed, not only in cryptocurrency but in life.
That’s a great mindset. Do you have any final advice for the audience?
One thing I want to say is to give back to society. If you have succeeded, remember that someone paved the way for you. Expressing gratitude and sharing your knowledge is one of the most meaningful things you can do in this field.
From a trading perspective, don’t become too attached to your positions. The market will always surprise you. When you make a mistake, cut your losses quickly and humbly acknowledge the error. Most importantly, view your investments as scores on a scoreboard—until the money is in your bank account, it’s not real money. If you remember this, you’ll avoid some of the biggest traps in this field.