Letter 100: One Hundred Learnings After Five Years in Crypto
Five years distilled into one (long) post
I started this Newsletter in June 2021, a few months after I decided to go “full time” in crypto. It’s kind of hard to believe it’s been five years since then. So much has happened. I’ve made stupid amounts of money, I’ve lost stupid amounts of money. I’ve met so many interesting people, and made lifelong friends.
More than anything though, I’ve learned a lot. I’ve learned about myself, this industry, the human condition, and so much more.
I wanted to do something a little special and different for this 100th Newsletter, so I sat down and tried to think about all the things I’ve learned over the years, and amazingly I came up with well over 100 things.
I whittled the list down and here are 100 of the most important and impactful things I’ve learned after five years in crypto:
If you struggle sleeping due to market fluctuations, you are overexposed. Excitedly checking prices in the middle of the night? Waking up and afraid to check prices? Overexposed. Do something about it, or the market will do something about it for you.
No matter how much money you make, you’ll always want “more”. Very, very, very, very few people can escape this curse and way of thinking. There’s nothing inherently wrong with wanting more btw, as long as you understand yourself and your goals, and aren’t sacrificing other important things in the pursuit of more.
Money doesn’t directly lead to happiness, but it is an excellent tool for helping you become a happier person (largely by helping eliminate stress). I’m so much happier now than I was five years ago. I credit the majority of that to quitting drinking (which happened a bit over six years ago), but some of it surely comes from the financial comfort I have created for myself and my family.
There is no substitute for hard work. The real winners in every industry are the ones that work hard, not the lazy geniuses. With AI tooling as well, you can outsource a lot of the genius work. It really comes down to grit and determination and tenacity more than anything now.
The amount of work you can get done in a day if you really focus is obscene. Most people get distracted 100x a day and rarely get actual deep work done. Just 1-2 hours of deep work and you’ll fly through your to-do list. If you can manage to do 8+ hours of actual deep work, you’ll be unstoppable.
All tokens trend towards zero. This should be your default position. Then, look for exceptions. There aren’t many, but they are out there. Look for exceptions on different timescales too. You can still make money on a token you think is headed for zero if you get the timing right.
Take profits aggressively. The regret of roundtripping is almost always more painful than the regret of selling and watching the price go up, because, eventually, the price will come back down. If you have a lot of conviction, take partial profits.
The market is rigged. There are cabals upon cabals upon cabals, and you’re not in them. I’m not in most of them either. You can still make money, just know that the game is against you. Fwiw, all markets are rigged. Crypto at least allows for some level of transparency that tradfi markets do not.
Nobody cares about you. Harsh reality, but for the most part, your Twitter friends and Discord friends and Telegram friends are not your Real friends. If you’ve met them and hang out IRL that might be an exception, but until then, they’re just hanging out around you trying to make money — same as you probably are with them.
The longer you spend in crypto, the more jaded you become. This is a near universal truth. Most people are already looking forward to securing their bag, exiting, and never looking back. If that’s not you, find the other rare ones who are truly in this for the tech.
Crypto genuinely offers solutions that no other industry or technology can, and it will change the world for the better. Decentralization, censorship-resistance, privacy. These are incredibly important things that crypto offer. Most people don’t care though, which is sad.
Less is more. Fewer tokens, fewer airdrops farmed, fewer communities joined. Focus on quality over quantity and your portfolio (and mental health) will thank you for it.
CT (Crypto Twitter) is absolutely flooded with undisclosed promotions. Start from a default position of trusting nothing and no one. Do your own research.
There is an inverse relationship between the quality of alpha and number of followers a person has. Ignore what people with 100k+ followers are shilling you, find the real gems from the accounts with less than 10k followers, ideally even less than 1k followers.
Most VCs (Venture Capitalists) are not your friends. They are here to make money first and foremost. They might also want to support builders and ecosystems and what not, but their primary and ultimate objective is always to profit.
The most money I have ever made has come from being early to a big new trend, and then holding some percentage of the bag to insane heights. NFTs, meme coins, AI agents.
In other words, if you want the 100x or 1000x returns, you have to be a little bit crazy and hold beyond what most rational people would do.
The best alpha group is a simple group chat with 5 friends. Other chats can be valuable too, but you’ll never beat this one. Find this chat, make this chat, be a part of this chat.
There’s no such thing as a “bullish unlock”. If a lot of tokens are about to unlock and hit the open market, expect the price to drop. Don’t fight supply and demand.
Most people overcomplicate things from the beginning. Buy Bitcoin. Hold it. Go from there. Alts and higher risk plays should come later, once you’ve built your base. And only then, with a very small percentage of your overall portfolio.
Nobody knows what they’re doing at first. Most people still don’t years later. Don’t worry if you feel like a fish out of water; the drylands are flooded with displaced fish.
When everyone is euphoric, it’s time to be cautious. When everyone is scared, it’s time to pay attention. Or as the goat Warren Buffet said: be fearful when others are greedy, and greedy only when others are fearful. Easier said than done, but this mindset proves right over and over and over again.
You will sell too early. You will sell too late. You will almost never get it just right. Get used to the feeling. Or as some washed up unc once said, you will have Infinite Regret (and that’s actually not such a bad thing).
Most of the time the best thing you can do is to do literally nothing. Fight the FOMO and sit on your hands. Fight the urge to panic sell. Doing nothing is almost always the right thing to do, yet so many find it so difficult.
Every cycle, people say “this time is different.” Some things are. Most things aren’t. History rhymes a hell of a lot.
The market doesn’t care about your entry price. Nobody does, and you shouldn’t either. The sunk cost fallacy causes so many people to make bad decisions. “But I just want to get back to even…” is a toxic mindset, and you should try to rid yourself of ever thinking that way.
Zoom out. Then zoom out again. It’s easy to get caught in the day to day vicissitudes of the market but it’s rarely productive to do so.
Bear markets feel like they’ll last forever. Bull markets feel like they’ll last forever. Neither do.
The people loudest on social media are often the worst traders. Know the difference between content creators, larps, builders, edgelords, and actual traders.
Taking profits is not a sign of weakness. It’s a sign of discipline. If you publicly talk about selling and taking profits, you’ll almost always have some pocket watching people sticking their nose into your business telling you how you’re wrong, weak, paper-handed, and how the token is going to the moon. Ignore them.
Diversification doesn’t mean owning 50 altcoins. It means having exposure to uncorrelated ecosystems within crypto, but more importantly, it means have assets outside of crypto.
Set your risk tolerance before you enter a trade, not during it. Understand what your exit price is going to be (or at what price you’ll begin to take profits). Trusting future-you to make the right decision in the moment almost never works out.
The people who thrive over multiple cycles are the ones who are able to manage their risk well. The opportunity cost of going broke is enormous, and the smart ones understand this.
Having cash is a position too. A good one. A very good one. It took me too long to realize and appreciate how valuable it is to have a stockpile of cash. It gives you comfort in market downturns, it allows you to buy things on sale, and it earns you yield. Cash is king for a reason.
One big loss can easily wipe out many small wins. Protect your downside.
Reading whitepapers is useful. Using the product is more useful. You should do both, but know that whitepapers these days are often marketing papers and trumped up versions of what the actual product might be. Be a user, it’s the best way to understand a product.
If you don’t have your own thesis for buying something, with an exit price and plan in mind, you’re probably just gambling. Most people are gambling. Don’t be most people.
The best alpha is often free. It’s buried in long podcasts and boring documentation nobody reads and in tweets by accounts with 500 followers. The cost is the time to filter and find this alpha, but if time is on your side, it’s out there to be found.
Following smart people on X is one of the highest ROI activities in crypto. It’s dangerous because of how much noise there is on X, but curating your own list of smart people to follow that you trust is something everyone should do.
Most “research” people do is looking for confirmation of what they already believe. They make up their mind about wanting to buy a token and then they start researching to go “oh look, I found all these people who agree with me!” and then pat themselves on the back.
Learn to read a block explorer. It tells you more than any influencer will. This goes back to the whole “using the product” idea from before. Be a do-er, not just a reader or watcher or consumer.
Onchain data doesn’t lie. People do. So while the onchain data itself might not lie, it can be manipulated. Be wary of inflated TVLs and metrics boosted by bots and other tactics.
Understanding tokenomics is one of the most powerful things to understand. Most people still don’t know about market cap, FDV, liquidity pools, locked tokens, staking, etc. You gain a huge edge over most of the market by understanding these (relatively) simple concepts.
Every cycle has a new narrative. They’re profitable waves to ride, but make sure to get off the wave at some point. ICOs, NFTs, Memes, AI Agents. All went to explosive heights, before 99.99% of them crashed to zero.
If the team is anonymous and the code is unaudited, you should know exactly what risk you’re taking. I have sometimes YOLO’d in to trades knowing that the team is anon, and the code hasn’t yet been audited, because I wanted to be “early”. It can work out very well, but most of the time, it does not. Go in with your eyes open in such situations and only gamble with the smallest of positions.
Most people should not trade. Most people should invest. This is true inside and outside of crypto. Most people also don’t think they’re most people, so we’ll always have inefficient markets.
Tax implications are real. Tax is one of those things where an ounce of prevention is worth a pound of cure. Figure out your tax shit sooner rather than later. Future-you will thank you for it.
If your investment thesis changes, it’s okay to exit. Loyalty to a token is not a strategy. Tying your identity to a community and making friends with community members because you all love a token is a surefire way to roundtrip.
You haven’t taken profit until the money is in your bank account. Paper gains are worthless, and gains taken into ETH or SOL aren’t much better. Stablecoins are a bit better, but too easy to donate back to the casino.
In a similar vein, lifechanging money isn’t lifechanging unless you actually change your life with it. If you ever see your portfolio reach such a point, sell. Buy the house, pay off your debt, whatever it is — change your life. If you ran it up once, you can run it up again.
Almost every great trader has systems in place. Almost every bad trader has no systems, and trades at the mercy of their emotions.
Tribalism is one of the worst things in crypto. Bitcoin maxis, ETH maxis, Solana maxis. The truth is usually somewhere in the middle. Keep an open mind.
The people you meet in crypto are often more valuable than the investments you make. This industry has a great way of evening the playing field and you can meet absolute giants from other industries who are relatively new to crypto. You can also meet and make friends with absolute giants within crypto, simply by being a nice person, a curious person, a helpful person.
Crypto Twitter is the best and worst place on the internet simultaneously. I have such a love-hate relationship with it. I basically have stockholm syndrome. Most of us do. There’s so much value and fun to be had on CT, but boy is it a cesspool at the same time. I’ve seen the best and the worst of humanity on there.
Beware how a founder behaves in public. If they get aggressive or overly defensive of their project, it’s a very big red flag.
You will eventually get emotionally attached to an NFT. This will cost you money. That’s okay, not everything is about money. It’s okay to buy and hold something you love just because you love it.
The art market has always been irrational. NFTs are no different. Don’t try and rationalize too much when it comes to art NFTs specifically. “Why is this worth so much?” — things are only ever worth what other people are willing to pay for them. And people are incredibly irrational, so the prices of things will always be irrational too.
The technology behind NFTs will outlast any current meta around NFTs. I truly still believe the technology is absolutely gamechanging and will power the majority of the internet one day.
Not your keys, not your crypto. Time and time again we’ve seen centralized exchanges blow up and take user funds with them, with FTX being the most spectacular example in recent history. Be careful keeping too much money on a CEX (especially unregulated ones).
On the flip side, self custody is also risky. Most people probably shouldn’t do that either. This makes buying and holding and securing crypto inherently risky and tough. Educate yourself about the risks and come up with a plan best for your own situation.
Use a hardware wallet. This is not optional. They are not 100% bulletproof, but they solve a lot of problems.
Assume every DM from a stranger is a scam until proven otherwise. If something sounds too good to be true, it almost always is. Keep your guard up (this is just a good rule in life outside of crypto too, especially with AI attack vectors becoming more commonplace).
Use two-factor authentication on everything. Use an authenticator app, not text based 2FA. For ultimate security, get a hardware key (like a YubiKey) for 2FA.
Operational security is boring to set up and priceless when it matters. We’ve seen an increase in physical attacks targeting people in the crypto industry lately, so make sure you’ve thought through your personal safety and opsec.
I used to think that consistency beat talent and quality in content creation, but in an age of infinite content due to AI and bots, you need to be both consistent and talented. More than anything, you need to be human. Being genuine and authentic is the biggest moat you can have when it comes to creating content.
Writing about what you’re learning is the fastest way to learn. It’s what I did with this Newsletter. It’s still how I learn many things.
Sharing your mistakes builds more trust than sharing your wins. The content world is flooded with people posting screenshots of big wins and talking themselves up. Nobody really wants to hear about them. Be raw and real and share your mistakes and losses, and people will love you all the more for it.
Good content helps people. Great content helps people and makes them feel something. Goes back to the humanity thing.
Your voice is your edge. Don’t try to sound like someone else. It’s good to find inspiration from others but be wary of going too far and trying to emulate someone else too much. It’s always better to be the best version of yourself than the second best version of someone else.
It takes longer than you think to build something meaningful. Keep going. The biggest winners in the space across content and projects are the ones that built for years, usually through a bear market, and finally found their success on the other side.
Patience is the most undervalued skill in crypto. The market is a wealth transfer machine from the impatient to the patient. Figure out how to be patient. It really is a virtue.
Strong opinions, loosely held. Update your views when new information arrives. Don’t get stuck in your ways and refuse to listen to the market or what people are screaming at you because of bag bias.
Time in the market beats timing the market. Another cliche, but another damn true one.
Your mental health matters more than your portfolio. Step away when you need to. It’ll actually end up helping your portfolio too — if you’re in a bad mental state, you’re not gonna be making good decisions anyway.
Very rarely does a single trade change your life. Everyone is looking for their lottery ticket, their 1000x that will make up for everything. Reality is usually a lot more boring: habits and systems are how most winners win.
Humility is free and valuable. Arrogance is expensive. Don’t burn bridges, be humble, be kind, it’ll pay off multiple times over.
Product market fit comes from answering the questions “what will help the end user” and “what will make people’s lives better”. Build things that real users actually want.
The best investments in crypto look obvious in hindsight and controversial at the time. Shorting the top when everyone is euphoric will get people calling you a moron. Buying the absolute lows when a project looks dead and down and out is the same, but that’s where the greatest gains come from.
Five years from now you’ll look back at today the same way you look back at five years ago (most likely, you wish you paid more attention back then, you wish you took advantage of the opportunities around back then, etc). Don’t make the mistake of being complacent now and looking back five years from now, wishing you paid more attention.
Airdrops reward the curious and the early. The best airdrops come from trying new things, using new protocols, early, before anyone else. If you’re only ever farming airdrops based on lists that content creators put out, you’re missing out on a lot of the best gains.
A token going up 10x after you sold is not a loss. You made money. Move on.
The best projects ship during bear markets. Watch who's building when prices are down. It’s usually when most people tune out of markets but it’s honestly the time you should be paying attention the most.
Revenue solves a lot of problems. Protocols that generate revenue are often (but not always) the best investments. Find the ones that are making real money and have a plan to use that money to support their token. It’s a very good starting point.
Keeping a trading journal is one of the absolute best things you can do. Document your trades, your entry price, exit price, thesis, and any learnings. You’ll learn soooo much about yourself and improve so much if you do this one simple thing.
I mentioned this earlier about tokenomics but it’s worth its own point: market cap matters more than token price. A $0.00001 token is not cheap if there are a trillion zillion squintillion of them.
Not every dip is a buying opportunity. Some things go down for good reasons, and keep going down. Ignore the people screaming at you to BUY THE DIP (they’re usually just overexposed and what they’re really yelling is BUY MY BAGS).
Taking time off from crypto is healthy. The market will be here when you get back. Don’t feel like you need to be locked in 24/7 forever or you’ll miss something, that usually just leads to burnout and bad decisions.
If you get lucky and win very big on a trade, the absolute best thing you can do once you’ve sold and secured the profit is to take a week off. Go sit on a beach. Reset your mind and your new world. Most people try to double down and find the next win immediately, and 99% of the time end up giving back a lot of their profits to the market because they’re now betting bigger and think they’re a genius when they really just got lucky.
Your first bear market feels like the end. Your second feels like an opportunity. If this is your first one, know that we all felt the same way at one point. Most of us roundtripped all of our profits and gave everything back, sometimes more. Many of the most successful traders lost everything at one point or another. There’s always hope.
Most debates about which chain is better or faster or cheaper are irrelevant to end users. People just want good apps that work and are easy to use.
The projects with the loudest marketing often have the weakest fundamentals. The best marketing rarely comes from the projects themselves, it comes from their users genuinely singing their praises. See: HyperLiquid.
Almost all of the people selling courses on how to make money in crypto are making their money selling courses, or worse, by shilling tokens to you and getting you to buy after them so they can sell into you.
An investment that requires constant monitoring is a job, not an investment. That can be okay, just know the job you’re taking on by buying such things. I’ve lost so much money due to not tracking tokens and airdrops and claims from things I invested in.
Your portfolio allocation should change as your life circumstances change. Single at 19 years old is different from married at 35 with two kids and a mortgage. The general philosophy is more risk when young, less risk when old.
This same philosophy applies to portfolio size. You can afford to take a lot more risk when your entire portfolio is worth $500 and you can replace that if you lose it. You should take a lot less risk if your portfolio is worth $5m. The general trend is you should move from accumulation to preservation as your portfolio size grows.
Most token launches benefit insiders. Team, investors, advisors, etc. They are the ones coming up with the tokenomics, and they usually want to do it in a way that maximizes their own value. There’s nothing inherently wrong with that if they can do it in a way that is value additive and benefits the rest of the ecosystem — founders and investors deserve to make money too of course — but the thing to be wary of is when it’s done in an extractive way, a manipulative way, designed for insiders to dump on retail. Sadly this is all too common.
Many airdrops are worth farming. Few are worth holding after you receive them. Take your profits and move on, or at least, take partial profits.
Knowledge compounds the same way a portfolio does. Small daily learning adds up over years. The best investment you can make is in yourself.
We’re still early in crypto. It doesn’t always feel like it, but zoom out far enough and it is. If you believe this technology is going to be around forever, then people (and AI) hundreds of years from now will look back at these early days of crypto as the very beginning of a world changing movement still.
Life is fucking short. None of this really matters that much. We are blessed with the briefest of moments as a sentient human being, and we all waste so much of this incredible gift on the most useless things. Doomscrolling social media, instagram, tiktok. Getting into fights on CT with anons. Checking portfolios 10x a day. Losing sleep over a meme coin. Getting angry at influencers and VCs. None of it really matters. Don’t forget that. Don’t forget to live life. Have fun. Be happy. Stop and smell the fucking roses. Be grateful and appreciate what you have, rather than constantly comparing yourself to others and wishing you had more. You’re alive. You’re reading this. You’re breathing. That’s incredible. Like, INCREDIBLE. I know that life can be so tough and hard and brutal and unfair to the Nth degree, but if you’re still here, there’s always hope. I’ve hit rock bottom so many times in my life, lost everything, felt hopeless, but there was always hope even if I couldn’t feel it at the time, and there is always a path back. Never forget that. Don’t take life for granted. I lived over 30 years being blessed with very little death in my life. Then I lost my grandmother, my dog, and almost my dad. Those moments taught me more than the rest of the last 5 years combined. And, actually, on the shortness of life… as my namesake Seneca said two thousand years ago:
“It is not that we have a short time to live, but that we waste a lot of it. Life is long enough, and a sufficiently generous amount has been given to us for the highest achievements if it were all well invested. But when it is wasted in heedless luxury and spent on no good activity, we are forced at last by death’s final constraint to realize that it has passed away before we knew it was passing. So it is: we are not given a short life but we make it short, and we are not ill-supplied but wasteful of it… Life is long if you know how to use it.”
Life is long if you know how to use it.
Thanks for reading! I hope you enjoyed these 100 learnings. If just one person learned just one thing from these that improved their life, that’s a win in my book.
Here’s to another 100 Letters.
Cheers.
Disclaimer: The content covered in this newsletter is not to be considered as investment advice. I’m not a financial adviser. These are only my own opinions and ideas. You should always consult with a professional/licensed financial adviser before trading or investing in any cryptocurrency related product. Some of the links shared may be referral links.
Very interesting and insightful, number one hundred is the icing on the cake! 👍