based16z - Hyperliquid 交易、早期往事与如何把它做出来

Yo, yo, yo.

Hello.

What’s up, man?

Not much. How are you?

I’m good, dude. I appreciate you joining. This is sort of a mythical one for the chat.

Yes, excited to be on the Thread Guy show.

Hell yeah, man. Congratulations. Congratulations, dude.

Thank you. I made it.

I know, you did make it. All right, here’s where I want to start: I want to do some lore stuff. I was actually looking back. I think the last one of these you did was in 2024—Mando, OSF, Keyword Monkey. It’s kind of a classic.

I’ve told this story a couple times. The first time I ever spoke to you was, I think, November or December 2023. I was living in LA. I was with Frank. You, me, and Frank had a Google Meet, and I was on the call and just liked your Twitter. I wanted to talk to you. I thought you were relatively funny on Twitter.

I was asking you about the market and— a lot of time has passed since 2023. What do you like? What are you interested in? Honestly, you didn’t have that many takes, but the one thing you said was, “Yeah, I don’t know much about much, but this new Hyperliquid thing is pretty sick, and you should probably farm it.”

I said, “What’s Hyperliquid?” And you were like, “I don’t know, it’s this perps thing. Go figure it out.” It turns out to be the most profitable airdrop of all time, one of the greatest coins ever, and I feel like it’s the trade you’re known for in a lot of ways.

1. The Hyperliquid Trade

Yes, I think that has been my best trade ever. I don’t have a ton of good ideas. A lot of getting better at trading or investing has been trying to do less, and good things only come up once in a while that you can really crush. That was definitely the biggest one so far for me, but hopefully there will be a ton more.

How did you identify that? Did you trade dYdX? Did you trade any of these perps? Were you in the Rollbit trade before? How did you identify that?

I was in the Rollbit trade. At the time Rollbit came around, I followed some of these projects. It was early 2023. I had done crypto in 2021 and done pretty well. In 2022, I took off, went back, and finished college. Then I was a crypto VC analyst at a big fund in 2023, but I was also trading on-chain and finding stuff.

I found Rollbit. It was kind of the same crew of people I didn’t really know that well yet—Jez, Flood, and Sisyphus. It was like, “Oh yeah, this is this really cool new slot machine. Everyone loves gambling on it. The coin is really cheap. There’s kind of a revenue story.”

You had to buy it on Solana, which I had experience with from trading dogshit Solana NFTs in 2021. I was like, “Okay, cool.” That was actually a big win for me in 2023. It was kind of my only win.

I thought, “Okay, maybe I’ll try trading perps,” which is usually a terrible idea. I was trying to get some size on-chain, so I would go on dYdX, I would go on this thing called Vertex, and I would go on all these random perp DEXs.

At the time, there wasn’t a ton of leverage, and you would mess up the DEXs even buying 100 Bitcoins. If you wanted to get long 100 BTC, I’d have half on dYdX, a quarter on Vertex, and then a quarter somewhere else. You’d have 3 screens at once trying to get a perp trade on in the US.

Obviously, everyone was like, “Come on, man, just make a Binance account and buy some KYC from Papua New Guinea or whatever.” I was doing it the hard way.

Then Hyperliquid came around. I was looking for venture projects, and I was looking to gamble on-chain, so it was a good combination. I reached out to Jeff immediately after trying it. I was like, “Wow, this is insanely good. CL says good things. What if there’s something here?”

Then I met Jeff, and I was like, “Oh yeah, this is the founder. This is the guy.” You could immediately get the kind of pure-pill vision. I looked him up and went back and watched his podcasts on markets, and he was such a different class of person from anyone I had met in crypto pretty much ever.

I had never met Vitalik, so this was the first kind of super-early dude. I told our fund at the time, in late 2023, “We should buy this at a billion dollars before it makes any money. I think this will be the trade.”

They were like, “Okay, awesome. We agree with you. We’re going to give him a term sheet.” Jeff said, “We like you guys, but no thank you. I need the Bitcoin immaculate conception.”

At that point, I was like, “Okay, well, then I’ll just spend the next year or whatever farming this as my full-time job,” and I ended up doing that. I think it was really a founder bet in a lot of ways because he had a lot of— I mean, people all know this now, I think.

I still love the team and the product. I’m a pretty ADHD, impatient person, so I don’t have as many interesting things to say about it at this point. Obviously, it’s mature. It’s a great thing and continues to be one of the cooler things going on in crypto, but I don’t know if I have a differentiated Hyperliquid take at this stage.

At that time, it was like, here’s this super-awesome guy building something when I was trying to find a better product. It was an amazing confluence of factors that led me to just click-trade $3 billion of Bitcoin, 40x perp volume, for a year, a week, without any perp-trading experience. It was kind of fun.

I honestly don’t even want a differentiated Hyperliquid take, but I am curious about this because I don’t know how big of a trade it was for you. It’s the one that I think I know you for at the beginning.

Whatever you sold it at, I’m sure you did well, but most likely it was significantly lower than what it’s trading at right now and what it traded at maybe a month ago. I’m curious how you think back on a trade like that.

You farmed this thing for a year. You had so much conviction in it. I’m not sure I’ve seen you have one idea that persisted for a year straight. How do you reflect on the execution, and how do you even execute a trade like that?

You bet on this thing, it happens, it plays out, you get your airdrop, it’s in your hands, and it’s the timeline. Everyone’s talking about it. You were convicted early. How do you execute from that stage?

2. The Hyperliquid Exit

The first funny story about it is that I had the keys for all my farming wallets on a shitty old MacBook. It had always been working, and then the week before the drop came out, it died and wouldn’t turn on. It was just cooked, and I had no seed-phrase backup, as some people know.

This was 5 days before the drop. I had gone to Flood’s house through our very legal, deep VPN setup to get ready to claim, and the laptop worked. Then I tried to open it a couple days later, and there was just nothing.

I was calling Shoku and everybody I knew who had those high-up tech contacts. I went to the Apple Store and a specialized repair shop. He was like, “We’re going to have to send this thing to the IDF.” It was very deep.

I was like, this is my ticket. I had been doing well. I had made enough every year in crypto to support myself. I was also working a job. It was kind of a cool thing, but I knew this was going to be the big play at the time.

I was like, “Well, fuck.” I freaked out for a little bit, and then, out of nowhere, I remembered that my old roommate had kept my laptop from my first apartment in New York, in the East Village. I was like, “Yo, dude, by the way, did you potentially keep that laptop? I just kind of need it a little bit.”

He was like, “Yeah, I got you, but can you pick it up in a couple weeks? I’m kind of chilling with my girl right now.”

I was like, “No, I’d actually be really chill if I could come over today, maybe in the next 2 hours.” So I go over to his apartment, and it turned out the old laptop had the old keys. I saved it.

I had gone through the first day of the airdrop and the following 5 days—the run from $3 to $8—without the coins even. So I got the first 3 actually for free, without even doing anything.

I was like, “Okay, great. This is now 90% of my portfolio already at $10.” I logged in, and the first thing I did was buy more. Then I texted Shoku and was like, “Is this a good idea?”

Meanwhile, he was buying my coins. He was like, “Yeah, probably not. You should probably sell and put a bunch in the S&P and change your life.” I think that was actually the right advice in hindsight, and I’m glad that I sold some there.

I ended up selling the rest in the $30-to-$40 range, which I think was probably a mistake. Probably out of impatience, honestly. I think that’s something I will have to learn going forward: What is a forever-hold asset? How do you realize tail outcomes? How do you mentally remove yourself from something?

One of the biggest challenges is especially if you have a big position on, which I usually do. I size positions either really big or not at all.

Mm-hmm.

It takes mental space, right? Especially if you're trying to do other things in trading or investing, or if you have other things going on, it's a weight on you. Figuring out how to let go of that and be okay with, hey, this is kind of a permanent capital story, or this is an asset that I want to be allocated to over the super-long horizon, is something I have yet to learn.

On the change-your-life topic—by the way, congratulations. It should have been me. I had Trader Maidan on a little while ago, and he told the story about when he sold Breakout. It was life-changing money to cash in, and there were 24 or 48 hours of just the greatest euphoria you could ever imagine in your entire life, and then basically back to baseline: “Let’s get to work now,” even after life-changing money. After you secure it, what was it like emotionally? Has it changed how you think about trading, your views on the world, after securing life-changing money?

3. Life After The Big Win

You know, it’s funny, because when I grew up as a young kid, my parents did pretty well—upper-middle-class—but my mom is part of this kind of religious group that’s very much a classic L.A. mom-type group. They’re like, “You gotta meditate, money’s actually evil, and you should really just try to be content with what you have,” and all these things are just kind of desire, along with these Buddhist concepts. So I’d grown up on that.

At the same time, I was always a super-ambitious kid. Originally it was sports, then I got pretty shitty at sports, and then it was math competitions, and school was my big thing—trying to get into a sick college. Then I got into a sick college, and I was like, “I need to get the best job.” Part of being in college, too, was, “Okay, I’m around people who are some of the wealthiest individuals in the world.” I’m running around getting free courtside tickets to NBA games, and I’m like, “Okay, there’s something here.”

So it was a weird kind of self-identity or values thing that evolved semi-unnaturally, and I’d also been doing crypto since 2020 and running it up that way. Finally, you get to this thing where it’s like—I remember, dude, in 2022 I was dating this girl whose dad is a billionaire, a multibillionaire, and she was like, “Man, you spend all day on the computer. You’re trying to run up $10 million? This is no money. Just come chill with me. What the hell?”

So there’s that side of it, and then there’s the side of, yeah, I could get into the Trader Joe stuff, too. Anyway, it came from a lot of convoluted places, so it’s a mixed win in a way. It’s like, “Congratulations, you spent 3 years of your life, 16 hours a day on the computer. Here you go. You got to level 1 off level 0. Now what?”

I’d spent a bunch of time where it was like, “Okay, now I’m retired. Now I’m just going to go party for 3 months, go do a bunch of stupid things, spend time around low-vibrational people, and do things that aren’t really positive for me or feel that good.” That’s honestly what I did in the first few months after that. It was also kind of a gut check because even now, I don’t have an accomplishment I’m probably known as well for besides just hitting this lick, thanks to Jeff. So it’s like, “Oh, wow, I used to feel like I was on the come-up, and now where does my identity go next? Is this all there was?”

There’s a lot of mixed emotions around it, for sure, and it can be weird. But in summary, I was obviously feeling extremely blessed, super lucky, and happy for the karma that got me there. After a few months of puttering around doing the semi-retired derivatives trader bit, I was like, “Okay, I have to get on to what’s next, and I really have to go back to playing games at a high level.” The question of what that should be is still kind of open.

I think I’ve tried to spend more time with earlier private companies and develop skill sets beyond what I had. Obviously, being in crypto a long time, you lose a lot of what you had. I used to be really cracked—I taught a discrete math class, and I was a good programmer and a good writer. Now I’m really good at telling you that because this quantum headline came out, zkSync is going to pump. It’s a very silly way to orient your brand, along with Twitter.

I’ve had to work my way into thinking, okay, trading is still fun and rewarding, and I like having it in my life. How can I do it in a way—there are many areas of crypto trading I can go through, too. Lately, I’ve found literally options trading on majors to be the most interesting, just because it’s liquid and fun. I like variance. That’s a very long-winded, roundabout answer to that question, but it’s kind of my ramble.

Do you think making a lot of money via trading specifically, rather than running a startup or doing something like this, has made you a little bit nihilistic? When I read your tweets, I know it’s a bit, but there’s always some seriousness under the hood. Sometimes you’re having the greatest time ever and you’re euphoric, and it feels like you’re actually loving posting and writing. When you publish articles, it feels like you really enjoy it. Other times, it feels like you’re depressed as fuck when you’re tweeting, and I can never tell where you are on the spectrum.

Yeah, this comes back to growing up, too, and not even just trading. I was a very happy kid, and then around 15 or 16 I went through my aggressively drawn-out, edgy-teenager phase. I was a big Camus kid, getting blackout drunk every weekend, fighting with my parents, and doing all the silly depressed-teen tropes. But a lot of it came from philosophy, because I was originally a big philosophy kid.

I think what helped me in college was that I went from all of that easy nihilism or cynicism toward, ideally, reading Thus Spoke Zarathustra by Nietzsche, as cliché as it may be. It put me in a post-nihilistic kind of space. Day to day, I don’t feel like I have everything figured out in terms of how I think about things philosophically. My mood can fluctuate. Meditation is still good for me. That probably grounds me most weeks.

Are you a daily meditator?

No.

No.

But when I do meditate, it’s good. It’s so funny: I used to use it as a hack. I’d take these math competitions or tests, or do interviews for hedge funds, and I’d be like, “Okay, I’m going to do my 6-minute meditation before,” and then I’d rip on it. I’d be out of my head. I still find that I’ll use it as a crutch like that.

Yeah.

I try to do it more, but obviously there are many things pulling your brain in so many different directions, and you’re a victim of your own habits sometimes as well.

You made a comment earlier, as far as trading goes. You said you size really big or not at all. Can you explain your trading style to me, or at least the type of trades you do best on and make the most money on, positioning-wise?

4. The Asymmetric Trading Style

Yeah. There’s short- and long-term, right? I can go back to when I started trading in 2020. I had $5,000, and I had made it from tutoring and playing online poker. Then I basically just got pretty lucky.

I got into crypto because I was going to work at Andreessen—or I was trying to. I think they rejected me at the last round. I was a college sophomore. I was programming in Cairo. I won 1 ETH in a hackathon for their ZK programming language. I was very sovereign-individual-pilled, so I had an academic kind of approach to crypto, thinking, “Maybe this will be an interesting career avenue,” or at least a fun thing to show on your résumé, because I was a box-checker, résumé-builder kid at that time.

The first NFT I ever minted was this thing called Blipmaps, and I literally got so addicted to minting them because they were so fun to mint. I remember I was with my friend in my college apartment. I basically full-ported into it—about 2 ETH—because I was addicted to minting it. They were 0.1 ETH, and then they went to 30 ETH, so I was like, “Oh, wow. Now I’ve made $200,000,” which is more money than anyone around me had ever seen in their life, except, obviously, at college with people’s parents.

But it was like, “Oh, this is the thing to do.” So then I kind of locked in. I traded NFTs for a year. At that time, what I was really good at was getting lucky the first time, and then I was in the Discord there and could spot things that would do well from an art perspective. Terraforms was big for me.

I was also open to Solana as a thesis, so I did really well just finding Solana early. I think that was thanks to Ansem, who I actually met in a strip club in 2021 in Miami. Fun lore. I was like, “Yo, are you Ansem?” And he was like, “How do you know that?”

At that time, I think a lot of crypto was just about being early, which I think is also true for Robin and Hyperloop later: exploring things and then having that initial filter to ask, “Am I early or not?” and “Is this legit or not?” Now crypto has matured a lot. I find that, in the last year or so, I can be good at finding asymmetries where I can develop high conviction and take aggressive options bets that other people might not take.

This year, all my P&L is from 2 trades: 1, jamming weekly Bitcoin calls on the Besant headline—

That was a good one.

And it’s like, as long as you can put enough in, you can get up to 300x leverage on notional with call options if you’re buying short-dated enough. When it works, it can really work, and in that case, you just feel it. I can find those spots by developing interest.

The other one was Robinhood, right? It was like, “Hey, if you can get insane leverage and just size it ridiculously, you can make a lot of money, kind of like a venture bet, as long as you’re willing to lose all the premium.” It’s been about trying to max-exploit spots where I think I can be right and try to win in huge ways.

I haven’t, because I’ve been working a lot more on non-trading, and so I just have less time to have all that coverage. For example, I can’t be like, “Oh, Variational is going to be a sick farm. I need to get early to that. I need to start developing a bot.” Those are things that I think are either just laziness or just that I’m not up on them.

With Pearl, for example, I knew about it and was kind of interested in it, but I never double-clicked. That’s probably a more sustainable way to make money with less downside. It’s kind of like Jez, right? I think Jez and I were very similar at the time: find something early, develop conviction around it before everyone gets access, and buy it when it’s hard to buy.

Your downside is really limited and your upside can be great. That’s the most classic, pure way to make money in crypto, which is what I did for the first 3 to 4 years in crypto. Now I’ve tried to find these narrative and positioning inflection points that I can just hammer. My P&L really depends on—

Whether I have the self-discipline to wait for the spot where I really know to hammer. Even with MetaMuse, I messed up that trade, I would say. And—

I’m still pissed about that.

Hitting that would have been the 3rd one, because it became so obvious that Friday when it went to No. 1 in the App Store. I kind of tweeted a question like, “Yo, can this work as a consensus?” instead of really developing the conviction and slamming it on calls.

It’s about spots like that, not punting at spots where you’re at 50% conviction or something, and having the patience to do nothing. Yeah.

Where have you lost the most? What setups do you get crushed on?

5. Where Trading Goes Wrong

Perpetual futures. Perpetual futures are terrible, dude. Because I needed to farm Hyperliquid, I would just trade perps all day. One thing about Hyperliquid is that it’s an amazing product. The thing makes you want to sit there and click.

All day.

I actually have little to no edge, or maybe a negative edge, on super-low-time-frame price action, and yet I have the same desire as with call options to be 40x levered all the time. It’s just out of bad habits from trying to farm volume on HL and from the way I developed as a perp trader.

Historically, I’ve had winning periods, but if you look at my all-time P&L, my biggest losses are definitely on perpetual futures. I also had some other big losses buying too many SPX puts last year, if people know that hilarious saga.

That was great.

I just kept wanting something to work that wasn’t working. I think there was something to learn from that: if at first you don’t succeed, actually stop trading. I think that—

Why do you think that didn’t work, by the way? I felt like that should have worked. The 0.3, minus 0.3 meme.

Yeah, I can’t tell you. The S&P is a market where even professing to have an edge is probably very hard, so there’s a certain stupidity in even trying. That would be the first part.

Second of all, the USD is not going up on a purchasing-power basis or in any other sense. As Good Alexander put it, “Oh, you’re trying to short the stock market like you’re trying to get more USD?” It’s kind of a cooked proposition, and I think that may be a structural reason why it wouldn’t work.

I can’t tell you who propped up the S&P 500 during that period, but obviously they were right, because it’s higher now.

Okay, your 2nd-most-famous trade, unfortunately, which I just want to know. Um—

Yeah.

Snapchat.

Oh, yeah. That’s so funny because, at the time this account started blowing up, it was all memecoin trades.

It was.

Which were, for better or worse, kind of a trend. But Snapchat was a spot where, again, I had been talking to 1 of my friends who’s a really great CEO, and I had seen this inflection around the subscription revenue. I had seen it as, like, “Okay, wait, this is going to become free-cash-flow positive after being nuked forever.”

Nobody cares about this thing, and you have a tail call option in specs, because I was pretty bullish on new form factors. Zuck has been trying to beat Apple’s kind of hardware moat for a long time. There’s another thing where my iPhone has been getting worse to the point that I’m actually open to switching form factors pretty soon.

Oh.

So I felt like there was a way to cut in. It was a product that I had seen my brother, who’s younger than me, and a bunch of younger people using, as well as the Burnerverse kind of screenshot. I had just seen Snapchat becoming ubiquitous.

That’s a good one, actually—the Burnerverse.

Yeah, right?

That’s a good one.

Like, becoming ubiquitous again. So all those things kind of came together. I’m still sympathetic to it working, but I think it was just like, hey, Evan’s out to lunch. You’re betting on a bad management team.

There’s no way for the S&P to include it. Sleepy Sol actually wrote, “Why would you even bet on this? Evan doesn’t even care about pumping this because he can’t get into the S&P, so there’s no exit liquidity if he pumps it.”

There were just a bunch of things that I missed. I was like, “Oh, my God, I’m such a genius. I found this great business turnaround case with all these confluences.” But it was like, hey, you missed the huge thing standing right in front of you, which is that it’s a historically terrible management team that barely even has an incentive to pump their stock, and they’re printing stock all day.

You would not only need this to work, but you would need it to work in such an aggressive way that you defeat the kind of structural issues that you maybe forgot about. But that was a fun one to get ragged on. I don’t mind being wrong in public. I think it’s pretty fun.

Honestly, given my win rate historically, I’ve been profitable every year in crypto. My win rate has always been around 25% to 30%, just because of the asymmetry that exists here. So I’m almost always wrong, with good results.

How much are you risking? What percent do you draw down on a conviction trade like Snapchat?

Snap was actually way too much. I probably drew down 10% on Snap because I had bought at the top.

Full port?

Yeah.

Fuck.

Which is not smart at all. In the last 8 months—

Jeez.

I moved 70% of my liquid book into an account that I can’t touch. At that time, I would have 1.5x my net worth leveraged into Snap, which is how I used to trade things on a smaller book, and I was cool with that.

I’ve had 60% drawdowns. I’ve never had a full blowup, but I’ve definitely had 50% to 60% portfolio drawdowns in smaller size, especially when farming hype, because I was perp trading all day.

I was just slowly drawing down over time because I was endlessly paying a bunch of fees. Oh, am I still on? I almost just quit the Zoom application here. I think we’re good.

No, you’re good. You’re good.

Okay, cool. Anyway, I’ve learned to put some money away that’s not related to trading so that I can go back to feeling really confident with the book that I am trading and being willing to take 40% bet sizes on that book without it really risking my whole livelihood.

You mentioned the meme coins. 2024 was a wild year, and I feel like you were really at the forefront of the nihilism cycle for a lot of it, also narrative-wise. How much of an impact do you think coming up trading meme coins has had on the style that you approach markets with right now?

6. Meme Coins Create Bad Habits

Yeah, for me it feels like NFTs were number 1, but then meme coins were an extension of that, where I saw the same thing happening again. It was a weird thing. I think what meme coins taught me in a bad way is that it was so PvP: We all know this thing’s going to zero within—actually, honestly, not everyone said that at the time. People were saying these were going to be a new kind of permanent asset class.

We had Murad, right?

Yeah, we had Murad and all these things, and it was like, no, it’s like NFTs. You’re playing a game where it goes really high and then it goes back to zero. The way you play that game is so different from what you might play with an asset that somebody might want to own forever.

I own a George Droid token forever, but I think there are very few of those people in the market. It probably taught me a lot of bad habits. It caused me to be overly not long enough beta, in a portfolio sense, and to be overly short-termist with things.

There are some other habits to unlearn, but I think some of those can be really true in equity markets today. I was an investor in Saturni’s business. I think he’s been really ahead of the curve on how memetic and narrative-driven equities have gotten.

You can make money trading the meme story on Meta. You can make money trading the SaaSpocalypse headlines on Anthropic blog posts. Those are all the same kind of short-termist, zero-sum playing fields. You can keep playing those, but at the same time, as I’ve talked to CEO friends, it’s also probably better to try to orient your life around playing long-term, positive-sum games.

I actually retweeted a Naval 2018 post the other day. A lot of my initial guidance to go try to get rich was from that era: own equity, own tokens, work long-term gains with long-term people. Somewhere along the way of spending a lot of time in crypto, you can lose that wisdom and have to gain it back, because there’s not a lot of compounding in playing poker all day.

By the way, you take your retweets pretty seriously.

I enjoy retweeting. Myself and my retweets do way better than my tweets. Sometimes I’ll find a tweet with 10 likes, retweet it, and come back to find it has 6,000 likes. I’m like, “Okay, we just—”

I had a friend who wrote a thing about curating as content creation. Even the way I like exploring copypastas—social media is just such a slopped-out platform that I think a lot of posting is one-on-one with curating, copying, collaging, and repeating a chant back into the same space that you’re reading. Yeah.

Going back to the memetics of markets, it comes back to this article. It’s my favorite article you’ve ever written, honestly. By the way, I think the neo-feudalism arc is blocked on your website. You’ve got to fix that fucking thing. The vibe—

Yeah, let me—

Click, slap, click, click on it.

Grok, Grok, get over here.

Yeah, somebody fix that shit. My favorite one that you’ve written, which I’ve referenced infinite times at this point, is “Megachurch.” I honestly don’t know how well it’s worked for me, but conceptually, it was such a fascinating idea to hear articulated. People trade this way, and there have been infinite trades like this.

I met Chris Camillo. This is basically how he trades as well. But to hear it spelled out like that was fascinating, and you referenced—I think you referenced Saylor, but you referenced the Sydney Sweeney–American Eagle trade, which is just my favorite trade ever. I played no part in it. I wasn’t even paying attention when it happened. But did you trade that well? Can you talk about “Megachurch” a little bit?

7. Trading The Megachurch

I traded it okay. I saw that—so, a lot of times when I get these high-conviction spots, like I mentioned the Bitcoin thing earlier—

Yeah.

It wasn’t just that Bessent had these comments. It was that there was a Trump conference coming up, Bessent had these comments, and all the sharpest options-trader dudes I follow had been saying—Stowe was looking for an upside break, and the sharpest options dudes I follow were saying call sellers were offside. There was all this other background context that suddenly rolled into that light-bulb moment where you go, “Oh, shit. Get me to the screen. Let me slam this.”

Got it.

In this case, on American Eagle, I’d been following this dude Sleepy Sol on Twitter, who I really like and who has a bunch of really good insight on consumer names. He had been posting about American Eagle for 3 months, saying, “Hey, this is a turnaround story. It’s trading really cheaply. The business is kind of turning around. Keep an eye on this one.” So it was in the back of my mind.

Got it.

Then I saw that Sydney Sweeney thing come out, and then I saw this guy Wagey Capital saying, “Yo, this is going to be huge for American Eagle.” It all came together instantly in my mind. I was like, “Sydney Sweeney’s the biggest person on Earth. This is going to go the most viral of all time, and the stock is already super cheap according to my expert network here, Sleepy Sol. I can basically full-port this.”

So I basically put 80% of my book into spot American Eagle at a decent size. I was moving the name around.

80% size?

Yeah, because I was like, “What’s my drawdown risk here?” It’s a decent consumer stock that’s not going to go to zero tomorrow, my friend already says it’s good, and my upside is great. This is real asymmetry.

As I’ve learned going forward, sizing smaller actually would have been better. Because I had sized so big, I was glued to the tick chart, and I ended up taking profit on a majority position at around a 40% move. Obviously, that was great—it was very good for my portfolio—but the stock went 3x, right? I didn’t actually realize as much equity as I should have on the bet because I oversized it in that way.

I’ve tried to size down, not because it wouldn’t have made as much money. I think the sizing could be right from a drawdown and upside perspective, in a Kelly criterion sense. But it was wrong in the sense that you have to look at your own emotions and ask, “Is sizing this trade this way going to cause me to manage it differently?”

That’s where I traded it poorly. But that was a fun one where everything came together, and this is the new internet. Now we have Sydney Sweeney doing naked prediction-market ads.

Insane.

We’ve reached the logical post-conclusion of that story, almost like an epilogue.

Why did that happen?

How did that prediction-markets one happen? I don’t know.

Kind of like, how did we get here? Yeah.

How did we get here? Yeah. Every idea that comes out becomes an abused parody of itself on the internet, because, like I said, with curation, repetition, and memetics, the incentive, the pattern formation, and what the algorithm wants you to do is repeat back a twist, a re-quote, or a video reaction to what you already saw.

When people see something like Sydney Sweeney ad rips, they don’t think, “Who’s the next mega-celeb?” They think, “How do I get a Sydney Sweeney ad for my brand?” There’s a very narrow way to interpret that, and once you have that amount of copying, you end up with this garbled, silly version of what was originally awesome.

How impactful do you think Twitter is in your trading performance?

8. Twitter Becomes The Market

I don’t know. Twitter’s weird because, as the account’s gotten bigger, like, when I used to be—when I—

I started this account in 2023. It was at 2,000 followers, and I'd just be like, “Yeah, man.” I'd be a community member, literally. I'd be out there all day like, “Yo, Retardio is the future. Get out of my mentions.”

It was so fun because that was part of the optimistic side of crypto that I remember from NFTs. Even as I have my own nihilist view on it now, it was like, “Hey, we're all rallying around this kind of asset. It's a fun way to come together, and shared ownership is cool.”

As I got further along, if you're able to curate, Ansem is definitely the best in the world at this. Maybe actually one of his best skills is that he found my account—we didn't know, he didn't know it was me IRL—when it was at 3,000 followers and started being like, “Oh, you have some good ideas.” He finds these other accounts that are way better than me instantly. He somehow has that venture ability on Twitter accounts.

I think if you have that, there's a way to get ideas from smart people. One is to look at them on Twitter, and another way is to talk to them directly in group chats or on the phone or whatever. Those are both equivalent. The part that you can uniquely get from Twitter is probably the general feeling or mimetics that you can internalize.

The part that's tough is posting stuff. I think Good Alexander helped cause the NVIDIA kind of scare, and I think Satrini contributed too, right? I've definitely caused some of my own things—

DeepSeek?

DeepSeek, yeah. You remember the NVIDIA trade?

Yeah, that was fucking nuts.

Yeah, that was one of my best trades that year.

How impactful do you think Good Alexander was on that? Do you think it was significant?

I mean, I kind of watched it go from buzzing to buzzing louder to, “Oh, man, this Good Alexander tweet is going to get 5 million views, and it's also causing me to want to short it.”

Whoa.

I feel like that was an accelerant, or the inflection point of that story. Obviously, Satrini had surfaced it, and other smart folks had surfaced it when it'd come out 3 weeks earlier.

It's so funny to see how that kind of works. News is very similar. News comes out, the stock does nothing, and eventually the story reaches that parabola. Then all of a sudden, all the price action shows up the next Monday. That's true for both the DeepSeek trade and for what happened with Meta, largely.

What about HOOD? How much do you think you impacted HOOD?

Probably a little bit, honestly, which is crazy. I was just trying to, when I'm in flow, be like, “Okay, here's my idea. I want to be right in public. I feel good about this. I want to share this with people. Also, I can help spread the story.”

But I think you obviously get to a certain point. I used to buy a random shitcoin on a tracked wallet and then sell it immediately—

Oh, classic.

—just to do the bit of, “Oh, this is all so stupid. I'm just moving this thing around.” I don't think that's a good way for us to be interacting with the market, because it's not scalable at all.

Yeah.

Nor is it positive-feeling. Then you feel like you don't want to take profit on it, because I'm taking profit literally directly from causing this ripple.

Definitely partially. In the best case, I like to be, “Hey, I can help be an accelerant for a story for either a company over the long term or for a trade idea that becomes bigger than it.” I think what's worst is you put out an idea, it goes viral, and it wasn't really right. Therefore, you just did an American shitcoin on it, and that's what I like to avoid, obviously.

But that's part of Twitter too: posting into things and sharing your ideas around. I think people would admit to less of the impact of that. Even SemiAnalysis, which I wrote about this week, is the scaled version of that. This is probably a 9-figure ARR company that literally just does KOL posts to pod shops.

Insane.

That's kind of how the market works at this point, for better or for worse. Obviously, I'm a member and viewer of that system at the same time.

Rather than your trading, what do you think about Twitter impacting the market broadly now? I think you just wrote about this in Mused.

Yeah.

It was X as a platform to basically pump stocks and sell equities, and that's it. That's what everyone—Elon's on there doing it, Axiom and Avengers are on there doing it. Everyone from microcaps to multitrillion-dollar companies is doing the exact same thing on this app all day.

Yeah. It's been pretty obvious to watch Jensen make an account and see what Alexandr Wang is doing.

It's crazy.

Even if you look at—I was trading GitLab this week, and the GitLab CEO is trying to make the most pitiful efforts to get, like, 4 liked tweets about his sword song.

You love GitLab, by the way. It's on my stream docs all the time. Basically, because you tweeted out GitLab again, I'm like, “Should I long it?”

I don't know. GitLab's a funny one for me, because there are parts of the software stack that I understand. That's why CRMs or GitLab or—

MongoDB.

I enjoy the tradability of names when you're more familiar with what they actually do and you've used them. That's what's been so hard about semiconductors for me. I can't tell you what a substrate is. I don't have any interest in learning about hardware. I don't know how a fab or a tape-out works. All these things are just boring to me.

That was true for crypto, and now it's moved into equities. Obviously, semis have been where people have been making the most money, and I haven't participated in that. But at the same time, it's nice to be able to trade something that you generally understand. Even if you don't have to go so deep into it, I think that impacts it.

Twitter more broadly, yeah, it's definitely the place where capital allocators are reading their slop. Where does somebody log on all day and read? That's where it is. That's why everyone's there.

Just like my own progression from what might have been a more traditional hedge fund career to clicking and trading options on storytelling, the broader market is also moving that way, with Chris Camillo or even varying levels of how people trade at pods. People want to act like an investment committee has some rigor at these long-only funds, but at the end of the day, they're also having 10 hours of screen time, right? These people are making the decisions.

There's a subconscious and conscious impact from that that is now being responded to in the market of information.

“Stock down 30% year to date, mandatory David Senra podcast.” It's so good.

Dude, that's actually so true, though. You'll see, “Uh-oh, the app-loving guy's on there.” When Evan Spiegel went on there after the Snap nuke, I was like, “Man, this is the nail in the coffin for me right here.” It's so—

Cerberus is due. Cerberus is beyond due.

Yeah, Cerberus needs to go on Senra soon.

The thing that's hilarious about your trading style, by the way, is that you're a brutal noti. Every day, based on your positioning, which I feel like you flip a lot, you are the most bullish ever: “The dollar is zero. The United States is going to shit. Defaulting on the debt.” Then the next day, you're like, “Worthless scam. Fuck this,” and you're retweeting. It's nonstop, and everyone follows you. It's all over their feed.

Do you actually think like this, or is it mostly positioning-based? Is every day sort of the worst or the best ever, and do you flip like that?

Yeah, I find that I can switch my mental state very quickly. I find that you have to in order to stay steadfast, because my positions that work, work really well and go hard.

The way I'm going to make money is to realize, “Okay, if I got these Bitcoin calls, I need to hit the move all the way from 67 to 74, 77-plus. If I bail early, then my whole strategy doesn't work.” I need to gain conviction that this is going to work in a really deep way, so I almost psyop myself with, “Okay, it's time to be bullish on Bitcoin.” What's all the…

I’ll even post, like, this week, “Here are some Bitcoin narratives that could work for bulls this week.” And I almost treat narratives—

That was a good one.

—for myself as a way to hold onto the position. It’s a way to be like, “Oh, I want to sell this right now.” It’s like, “No, no, no, think about it. The dollar’s going to zero.” Just repeating those chants and mantras is almost a way to remain convicted. And then, obviously, my subconscious brain is distributed across Twitter a lot, so that’s just a byproduct of me doing that to myself.

Yeah, repeating these mantras that the dollar’s going to zero is nuts. How have you done trading-wise in 2026?

I’ve done pretty well. But it all turned around on literally that Bitcoin trade on Besant. Before that, I wasn’t doing super well, and then I had a streak that was really sick. I had drawn down probably 15% to 20% on the year before that, and then my portfolio went up 2.5x in about a month on GoPro, HOOD, and Bitcoin.

Oh, you hit GoPro?

Yeah, I hit GoPro too. It was one where I actually didn’t make as much as I probably should have, just because I think it ended up being my tweet—

That was—

And so then, like I said—

Exclusively your tweet.

I’m more hesitant to really realize P&L quickly. I still will get out. I don’t want to lose money just because I tweeted it, but I think that could’ve been better, or something like that.

There were some other trades in there. It was the first time all year that I focused on trading all day, because I have a bunch of other responsibilities now. So I took some time to be like, “Hey, it’s been a kind of shitty year. Let’s lock in and see what we can do.” I tried to trade Carvana puts, which was wrong, but I was really online for that at 9:15 a.m.

Trading well for me is really a function of being hyper-online and paying attention to news, price action, and smart people. I think the challenge of the last year and a half has been that, as you want to expand your life into other things, focus and develop skills elsewhere, and drive value to companies on a more long-term basis, you lose some of that ability to perform really well trading. That’s a trade-off I still have to work with.

The thing about your trading style that’s hilarious, at least from what I see reading through your tweets, is that I feel like you’re almost never in a losing trade. You tweet something that you like, and it either pumps 20% in an hour, or the next day you’re the most bearish guy on that position ever.

A lot of your Bitcoin—

Mm-hmm.

A lot of your Bitcoin—

Yeah.

Like, “Okay, Bitcoin’s going to pop 20% today for no reason.”

Mm-hmm.

Now it pops 20% for basically no reason.

Yeah, that was a fun one, too. I admit, somewhere in the middle, I didn’t execute that one as well as the first one, so it ended up being less impactful.

But, yeah, I’ve been a very unwilling-to-hold-drawdowns person. I’ve always been that way, especially because I used to be betting huge percentages of my book. If the price moves 3% against you, it’s like, “Okay, we’re wrong. Move on.”

I think it’s also a habit learned from trading 40x perps. It’s probably a bad habit to some extent. It’s the opposite of Jez being like, “I’m going to Martingale this all the way down.” I’m like, “Oh, man, this thing went 4% against me? Goodbye. Next idea.” It’s either really working or it’s not. I could probably loosen up a little bit, but that’s just how I look at things.

I think you do a really good job of sidestepping the cultural commentary that’s talked about on Twitter all day through little bits and pieces and tweets, but nobody really puts it together and saves it in one place for everybody to read. There are a couple of radicalizing things that you’ve written, and I think the canonical “Loot and—

“Loot and Steal.”

“Loot and Steal” is one that everybody feels. I think everybody, especially young people, feels it, sees it, and watches it unfold. Everyone was here when Trump launched a memecoin, so everyone saw World Liberty Financial. Everyone saw what was happening in the order books for the oil market.

But when you read it all stitched together, it’s sort of like, “Fuck, this is sort of worse than maybe I gave credit for.” When did you start to realize this, and do you feel—I know it’s not the best narrative—but do you feel pressure as a relatively young person to, I don’t know, loot and rob as a patriotic thing to do?

9. The Loot And Steal Thesis

No, I don’t think I see that as a very empowering primary ethic. It’s more of a commentary. Although, certainly, look, I’ve been in the world of cryptocurrency-related things for 4 years, which is largely a zero-sum game to be playing. And I think a lot of people—the smartest people in the world—are going to become quant traders, even. It’s a soft, soft version of this where it’s like—

That’s a good take, actually.

And I think I have huge respect for people like Elon, who are driving a ton of value, and that seems to be their core thing. But even there, I put out yesterday that the dude is tweeting about memory stock price action and pumping Dogecoin at the same time. It may just be for the bit, but there’s some aspect of this in even the most inspiring people you might imagine.

It just feels like—I don’t know. It’s not new, obviously. I’m not a student of history as much as I should be, but there are game-theoretic outcomes here: either the best action is to build, or there’s a Nash equilibrium where the best action for each individual is just to start skimming off the top. That feels like kind of where we are, and it’s hard to say that that should be something you should do.

Yeah.

I’m more just pointing out that the incentives and patterns generally are structured that way.

You’re obsessed with scamming in the medical industry.

I think I met these individuals—who I won’t name—

You’re obsessed with it.

They were making so much money, and they also kind of screwed me over one time, so I—

Really?

This is also personal bias, right? Everything is—

Uh-huh.

Something happens to you in the real world, and then it shows up in your thought patterns. But, yeah, I did run into a case of that that I found very aggressive, and that definitely influenced my thinking on it.

What do you think you’d be doing right now if you were 20 in 2026, or 19, and had just graduated high school? What would you be working on right now? Would you go into trading? Would you start doing crypto now? What do you think the next generation of people should be doing right now? Like the way you—

20?

What would you be working on?

10. Build Your Own Game

I’m spending a lot of time right now working on WAP. I think that’s really interesting. It also embodies a lot of how you might describe the set of options for someone with the goal of achieving things in an economic sense, which I think is a goal for a lot of people and was definitely a goal for me: to get my own economic freedom, because I always felt somewhat hamstrung by it.

My parents could be like, “Hey, you can’t do this. We’re not going to support this,” or, “We can’t afford this,” or whatever. And so that was a big part of it. If you have that as a goal, then I think it’s good to not go into a traditional job and try to do something on the internet for yourself, and build equity in it, or build skill in it, or build specific knowledge.

But what that is is just constantly changing, and I’m probably too old even to understand what the coolest one is. Maybe it’s building Roblox games now, right? There are some kids going insane on that. I think part of the WAP thesis is just: the smartest and most motivated people in the world are going to try to figure out their own things to do, and it’s going to be an ever-changing and ever-evolving meta.

So it’s even beyond crypto. I wouldn’t tell someone, “Hey, go into crypto trading.” If you had a real passion for that, I’m sure you could still do well starting from nothing. You can do it—you can make it do anything as long as you love it. But I would say, yeah, you’ve got to work on something that’s interesting to you, that you’re working for yourself, that’s probably a little bit new, and is hard to explain to old people—

Hard to explain to old people.

And that you’re going to have fun with.

At one point, I wanted to be a math professor, so you can also go do a career that's probably under-supported. Oh, I guess math specifically is blown up by AI, but—

Yeah.

I think doing deep study—I don't know. I can't give any better advice. I still think that—it's funny, someone tweeted the other day that this 2018 Naval advice is going to be stale in 6 months. But I read through it again, and that was the most impactful document, aside from Taleb's books, that I read from a pragmatism standpoint in college.

What was the advice?

I can't describe it as well as he did, but you should read the thread. The thread is called How to Get Rich Without Getting Lucky, I think.

Okay. Yeah, yeah, yeah.

I'm not going to paraphrase the guy, but it was—

Yeah.

It's very similar to this: build equity, build specific knowledge, study math, game theory, literature, philosophy—broad foundational things. If you can automate what you're doing at all, then it's not the right thing to be doing, and you're going to be automated soon. This was even before the AI stuff. It was: work with people that you really enjoy spending time with, that you could imagine working with in 20 years.

It was: build up distribution on the internet, make podcasts, make tweets, and make Instagram posts. All the kinds of things that I guess are now almost cliché advice, but I still find them to be foundationally true. I haven't found a document with more 2020s Lindy advice than that.

What is your math lore?

What is my math what?

Lore. Like—

I was just like that. I was trying to make it to an elite school, and I was trying to compete. What I was good at that was relevant to that was math competitions and things like this. I did not make the International Mathematical Olympiad, but I was pretty close. I did some research in high school at a local university that was collaborative and published on my advisor's thing.

I really like playing with puzzles. I think—or I find writing—

Yeah.

—to be similar. It felt creative too, because when you really get a solve on something, it's kind of like that same light-bulb moment that I now get a little bit from trading. The 2 things that really bring me joy are that light-bulb moment, whether it's on a trade, a math problem, a writing concept, or a sentence you put together. I don't know what I was going to say for the second one, but that one's really good.

The second one is pairing it with creativity, where I made something from this. A problem solution can even be similar in that way. I almost wanted to become a quant afterward, because I was like—

Whoa.

This is what math can be good for. I was interviewing at Citadel and shit. I ended up doing venture capital instead out of school while I was trading. But I like the creative aspect of it, TLDR.

I'm curious. This is kind of a complete side note, but I'm curious where you think things are going toward the 2028 elections. There are a couple of combining forces here. One, you write about the “eat the rich” stuff a decent amount. And also, you're a guy who becomes a billionaire when it's no longer cool to be a billionaire, or dangerous to become a billionaire.

You also wrote this post I liked a lot. It was quote-tweeting DoorCash, and you were talking about how deep in psychosis the AI crowd is after making a lot of money, and that you were in a similar spot in 2021 with NFTs. You were saying, “NFTs are going to change the world, they're going to do this, they're going to do that,” just because you're up 500 bands or whatever for the first time.

Yup.

There's this mash-up where everybody hates it. The vast population—the underbelly—hates this stuff so much, and then the people who have the most power are particularly deluded by it because they've made so much fucking money. Brad Garlinghouse and all of these guys are infinitely, generationally paid through this, and it feels like the 2 things are clashing a little bit. How do you think that plays out?

Yeah, I have no idea. That's an interesting thing to synthesize. Let me think for a moment. The eat-the-rich stuff—like all of these political movements and extremisms, even—there's been way more antisemitism, way more anti-rich sentiment, and way more nationalist stuff. On the other hand, there's way more pro-communism. All these are classic historical responses to a more high-volatility society, right?

Not necessarily for the better, probably for the worse, but these things are not new. I think in our time uniquely, because people want to call it peak capitalism or something like this, we've assigned every ethic toward money in a lot of ways. Maybe that's an overly biased statement based on my own time spent in crypto, but it certainly feels like money and literally online status.

And so that becomes the focal point, both as a way to delude yourself—someone who's up a lot of money on a trade might delude themselves about the veracity of what they're saying—and as something to point to as a powerful evil to fight against.

My friend had a good take: it's hard to have a Marxism in a consumer-first society, because Marxism is based on production and seizing the means of production. Actually, our whole value system isn't even about producing anything. Again, to bring up Elon, he seems to care about what we produce. But most people, if you look at what they're flexing or talking about or how they structure their life, it's more about, “I want to be able to consume at the level of that person.”

And so every movement that's these same historical echoes tends to revolve around, “I deserve to consume too, and you are consuming too much, and you're a billionaire, and you are the focal point of my anger.”

“You're the focal point of my anger” is good. Another one you talk about a lot, and I'm curious where you think this is going, is your relationship with Twitter and social media broadly. I honestly don't have a great question on this one, but I want to call out something I wrote down that I thought was pretty funny.

We were talking about Instagram and how 70% of Instagram posts are sponsored ads of some sort, and this is a problem because that means 30% is being wasted because they're not already ads. Is there any reversing this? I feel like a lot of people look back on pre-2016 social media algorithms, when it was actually not an FYP, it was just a Following tab, with a lot of nostalgia.

But then there was this era when Nikita shows up and he's like, “Okay, I'm going to change the FYP. I'm going to get rid of all the ads, all the viral shit, you know, the four-note prong, and I'm going to make it people you follow.” I remember being like, “Bro, I don't fucking want to see the tweets from the people that I follow. Give me the viral, give me the bait, give me the slop, give me the topic of the day.”

How does that play out? And do you use TikTok? Are you on Instagram? Do you use these platforms?

11. Building Beyond The Feed

I don't have TikTok. I don't have Instagram—

You don't have Instagram at all?

No, neither one, primarily because you're entering a parallel world when you choose to enter a social media application, and it wasn't a world I was especially interested in participating in. It wasn't helping me make money. I could do okay dating; I don't need help there, and I don't need help with anything else that it's bringing me.

So it felt like if I have an app on my phone, I'm going to spend 3 hours scrolling on it. I don't have the self-control not to do so, and so I had to just fully cut—

Yeah, you mentioned that.

Same with YouTube; I don't have it on my—

Yeah, you mentioned that.

On my phone either. I usually do that occasionally—I'll say to my friend, “Yo, check out this video from 2018 when I was a young child,” right? But I'm not up on the YouTube meta.

And so I think using a consumer application, especially a social media network, but also video and stuff, is just an adversarial game between you and the person who owns it. Ads, UGC, and whatever other version of an ad there is are just the most explicit way to make that financialized and to say, “Hey, I have this person kind of enraptured in front of the screen right now.

What would you like to do with them? Or what would you like to buy from their consciousness? And so, that’s the end. The only time you don’t have to be doing that, first of all, is the solved, most efficient version, so everything will become that, right? But second of all, the reason you didn’t have to before is because you still had some notion of, “Hey, we’re just trying to grow the user base of this, and so I need to optimize for their utility to some extent as a function of being able to monetize them in the end state.”

Is there a way to reverse it? No. I think by using one of these platforms—obviously, Twitter is a lot of fun for me. I consider it to be creative, and it also sometimes helps me find ideas to make money. But I would probably still be better off not using it, to be honest. I think that’s mostly true for every consumer application.

That’s one thing that I’m trying to find now, which is part of Whop and other things: what’s a way to use those same mechanics to make the incentives better, such that what’s good for the user is also good for the thing making money? I think that was part of what Substack was kind of close to being. If you do paid stuff—payment in general over ads—I mean, ads can also be good, but I think that’s a good way to think about those incentives. Anyway, I’m rambling a bit at the end here.

No, it’s great.

Yeah.

You mentioned Whop a couple of times. I don’t know exactly what your involvement is, but I’m curious: why do you want to work on something, and how does it change the way you interact with the world when you’re solo trading against other people versus working on some broader idea?

And secondly, what do you contribute generally? Why would someone want you to work with them?

To answer the second point—why people want me to work with them—I think I’ve built a good understanding in crypto about storytelling, and the same thing I talk about on X: how to frame and think about things. I’m also pretty good at giving product feedback, designing products, or coming up with ideas for products. I’m not necessarily the best coder or Figma user, but I can help steer people’s product direction as long as I give myself enough time to pay deep attention to it.

I can be good at that. Then, marketing and everything else—I think I also have some internet-version understanding of. Not the best in the world by any means, but I have some ability to make things happen in that way. And what does anyone need help with? People need help with recruiting. People sometimes need help early on raising money. There are other things that I can help with in softer ways.

Whop specifically has just been front of mind. It’s what I spend the most time on now, it’s my largest investment, and it’s a team that I really respect a lot, especially the founder. I’ve helped recruit people to it, and I hope it’s a more pure-pilled version of this post-AGI world in which you’re either going to be a slopped-out, doom-scrolling vegetable machine with a UBI, or there’s another way.

Let’s try to set up a system that takes all the tailwinds from the ways that cool—and not-so-cool—people have made their own way on the internet, and try to broadly grow that and make it accessible for everyone. You need some income to be able to do what you want. I think what I was originally going to be was just doing music all the time. I used to make a ton of music in high school, and I thought, “I’ll just be an ambient music producer.” Then I thought, “Wait, I’m going to be super broke.”

The same thing happens with less-than-great ideas, right? They get ruled out. Finding ways that people can make money from what they actually want to do is also a good ethic, and it’s something I really support. It’s a combination of a way to shape the world and an ideology that comes from my world. There are a lot of crypto adjacencies, a lot of people from internet hustler culture, and these sillier parts of the internet. But there’s also a way to build this toward something that can be a positive way for people to spend their time.

How doomer or optimistic are you about where things are going?

I don’t know. Obviously, I can be too doomery on Twitter, and Twitter probably impacts that as well. I try to be an optimist in my daily life about where things are going for myself, my family, and my friends, because I think it’s probably bad to live any other way. Obviously, sometimes you can get pessimistic, but I try to root that out.

In a more macro sense, I probably have a pessimistic framing of things often. I think I often read things through this lens of small systems versus large systems. I look at the small systems around me and ideally try to be a hyper-optimist, and then, with large systems, I tend to have a cynical bent. Maybe it would be better not to have that, but that’s true of me today.

Going back to the social media thing really quickly: no Instagram, no TikTok. I’m realizing, as I frame this question, that I’m infinitely fried in my brain, but the first thing that comes to my mind is, how do you occupy your brain if you’re not on fucking TikTok and YouTube? What is your information flow? I can’t imagine you have 10 hours of screen time on Twitter all day. What are you doing with the rest of the time?

No.

What are you doing with the rest of the time?

I read a little bit. I text in group chats a lot. If I’m in New York, I spend a lot of time with people in real life, having conversations or hanging out. I definitely spend too much time on Twitter, so we could look at my screen time there.

I look at charts and raw data, and then I spend time working on either Whop or occasionally other smaller companies. That might mean I’m in Figma, in code, writing, or on calls. Days definitely get filled. I don’t think any of us have a problem with that. I actually hope I can get to a place where there’s more time spent doing nothing, essentially. I think that’s probably a good thing.

You mentioned earlier that you off-ramped a lot of capital. Once you reach at least a couple of levels of crushing it in the markets, what are you allocated to in the long-term stuff? More specifically, how do you approach trading when thinking about when you flip the switch to not blow up—to not lose it all?

The way I’ve always done this, which is going to sound so stupid—and there’s probably a financial advisor sitting here thinking, “What?”—is that I literally just keep short-term Treasuries, around 70% of my portfolio, and then I take big bets on things that I have really strong conviction in with everything else.

The way that works is, if I blow up the entire big-bets book, I still have 70% left to try again. That’s how I’ve looked at things. I’ve looked at my portfolio almost always as bullets. I’ve also been looking at allocating a little bit toward real estate soon, because I’ve had so many annoyances renting, just for a life-setting decision. But I’m not super bullish on it, because there are a lot of boomer demographic issues coming up.

Dude, the apartment post was nuts, by the way. Holy fuck.

Dude, that was crazy. I could explain it, but look, they came back literally—we were like, “Okay, 60 came up—”

Holy fuck.

“—and they’re like, ‘Check this one out.’” And I’m like, “Okay, man.” Then they’re going to—he’s trying to get a commission, bro. He’ll be set for the year.

My question is, who’s renting that?

Groups of 3 or 4 dudes, maybe 2, or maybe 1 guy who’s got really wealthy parents. Their family is a family office, and his parents are like, “Yeah, find an apartment for our kid. No budget cap.”

Or it’s a lot of people I spend time around, where 3 or 4 pretty successful dudes are like, “Okay, we want to live in a sick space, but I don’t really want to pay $70K a month personally for rent—or $80K or whatever—so let’s all split it up. We each pay 20.” Those fill up quickly like that.

$70K is nuts. Do you want to trade for the rest of your life?

I don’t know. It’s an open question.

I've actually been having this conversation with friends recently.

What are you leaning—

No idea.

Interesting. You just wake up and you're like, “I feel like trading today.”

Yeah. There's a part that's a good addiction in that I love it, and there's a part that's a bad addiction: it's a high-dopamine, gambling-adjacent kind of activity to be doing. So it's really trying to look within myself and ask, is the passion I have for it really pure, or is it coming from a place that I can evolve beyond?

How much worse is your daily outlook on life when you're losing money in a trade? Are you—do you—

Gong! That's definitely—there's definitely some volatility. As ex-girlfriends will tell you, there's some volatility, and it shows up in my mood based on whether I'm making or losing money on a daily basis.

Are you often down for a month? How does it work?

I mean, yeah, energy is such an imperceptible thing sometimes. Am I going to the gym? Am I smiling? Am I—

Smiling. Fuck, dude.

—having fun in my voice? All these little reads you can pick up, you know? It's not like I'm crashing out super hard, but maybe I'll be drinking more and doing drugs more, or something bad, if I'm not in a good vibrational state. I definitely allow too much P&L swing, especially because I trade a pretty high-variance style, to affect my vibrations week to week. It's obviously better not to do that. I'm sure the best traders in the world don't have that, but for me, it definitely shows up.

All right, I'm going to ask you 2 things, then I'm going to give you a rapid-fire and let you go.

Okay, cool.

What is your—okay, this is kind of a broad, weird question, but I don't know. I think for a lot of relatively young internet-money Twitter people, you're sort of a symbol of, like, “Based16z did it,” so they kind of—yeah, you have some impact. What is your relationship with money, and how has it changed from not having it to having it? The reason you agreed to come on the stream, by the way, is you got rage-baited on Twitter, but you called—

Oh, I did.

—you got baited crazy. But—

I was too hammered. I met this girl at dinner. She was like, “I'm going to Scottsdale after we talk.” I was like, “I'll take you to Scottsdale.” I was hammered for 36 hours, and I was like, “Okay, time to tweet this.” Then I was like, “Oh, this is terrible.” But it was kind of fun, and then I ended up coming here, so things all worked out for the best.

I definitely had a very scarcity-driven, whack relationship with money as a kid. Not that I was poor in any capacity, but I was in a town where I was in the middle-class part of the town. There was a hyper-wealthy pocket about 15 minutes from me. I talked to a friend from high school recently who had a similar experience, where we would spend all our time at those kids' houses because their parents were old and didn't care and let us party all the time.

We would just become imbued with this idea: “Wow, they have this lifestyle.” There was jealousy and a bunch of negative things that you shouldn't be thinking about. When I wanted to go to college, I wanted to go to an elite private college, and my parents were like, “This is basically going to destroy our family, dude. What are you doing?” I think that messaging really scared me, even though we ended up getting through it. My parents worked really hard to help me, I paid for part of it, and it was good.

I think there's something I learned about it. I definitely was overly focused on it, though. You probably should have less focus, I think. Afterward, there was a period where I was overly into spending money. That still can come up sometimes. I think probably the best relationship with money is to not have too much attachment to it in a scarcity or spending way, and to hopefully just be acquiring capital for purposes that are beyond the acquisition of more capital.

What's the most retarded thing you bought when you got a bag for the first time?

The first time I ever got money in college, I started buying a bunch of those terrible Balenciaga shoes. I would have this whole, like, retarded shoe collection. That's why I started taking Uber Blacks everywhere in college, too. I'd be like, “Yeah, so basically I made a bunch of money, and I got 6 different pairs of Balenciaga shoes that looked super distressed and a bunch of expensive jeans,” and I'd take Uber Blacks everywhere and go to the club. That was a classic first-money vibe that was very stupid.

D. Gills wants to know about the Cadillac story.

Oh, dude, here's another dumb one. Shout-out ZQ if you're listening to this. I was a little buzzed, and I said to my friend, “Dude, having a driver full time is so dope. I should do that.” My friend has 2 Escalades that he owns with a driver, and he's like, “Dude, you can buy this one from me right now.” I was like, “Say less. I'll buy this Escalade from you tonight.”

So I did that. I wired him the money the next day. I'm not a very organized person. I was actually recently able to get an assistant to help with that, but I was like, “Okay, great. I have this Escalade. Now what?” He's like, “Well, you have to do the title and come pick it up.” I was like, “That sounds like a lot of work, dude. I don't know about all this.”

I ended up leaving it, and he was like, “Okay, I'm going to drop it off for you in this parking garage.” It stayed in this New York parking garage for about 2 months. The battery freezes, at which point he was like, “Dude, you have to go get it. I'm getting calls.” It was a $2,500 bill to take it out of the garage.

I took it out of the garage and drove it back to ZQ. I was like, “Dude, you deal with this. I don't want to—I don't even want to think about this anymore.” To this day, he still has it somewhere, I guess. I still paid him for it, and I've never used it. That's just—it's depreciating every year. But I do own a car.

That was good. How's the assistant?

She's great. It's really awesome. I feel super excited about that. It was just a couple weeks ago, and I won't dox anybody, but she's dope and I'm excited. I'll come up with threads a lot and then not finish them, so it's helpful with doing that, helping me get organized, and then helping me—

I think I've been lazy. Part of it is self-discipline, and then part of it is just setting up better infrastructure for yourself. I think I'm working on both.

That's pretty good. All right, I have about 5 rapid-fire questions, and then I'll let you go. Number 1, I have to ask a question: how much do you need to retire? And is there actually a number to retire at in 2026?

No, no. This is such a dumb meme, dude. There's this line from Office Space. This is a classic kind of '90s or maybe early 2000s movie. The guy's like, “Man, I really wish I had a million dollars.” And the other guy's like, “Oh man, so you could do what?” And he's like, “Dude, so I could just sit around and not have to go to work. I wouldn't do anything.” The other guy's like, “Man, my cousin's broke. He doesn't do shit.”

I think people have the wrong view of freedom in that way. Obviously, money can be good; it depends on how you define it for yourself. But you don't need to be trying to get to a number. It's something I thought about at that time too, long ago. You're never going to get to the number, first of all. Some dude out there just ran up $100 million and is like, “Oh man, I really have to get to $1 billion.” There's no end to that kind of treadmill.

And B, people living in economic scarcity makes everything harder and is challenging. But people, I think, mostly, except in some cases, have the ability to do what they should do. That'll be the way I look at it.

That was a really good one. Who's the most impressive person you've ever met?

This is a good question. I mean, there's a few angles to this.

There is.

I think—I mean, there's a most impressive—

There are a few angles I'll go at it from, in different dimensions. This guy, June, whom I met in college, was the most impressive person I ever met in terms of just raw intellect. I would hang out with this guy, and I thought I was okay in math, but he would be able to distill any concept immediately and solve math problems that took 2 people 3 hours in 2 minutes.

Like his brain just made the world make sense so much faster, by an exponential amount, than anyone I'd ever seen. I was taken aback, to some extent. And then beyond that, I'm looking for someone that I'm really just impressed with. I'll name another anonymous friend—I won't name them—but I think something that really impresses me is when people have a super calmness about them, as well as peace to them. I think that's one of the most impressive things you can have, and something that I'd like to work on myself. So this other person, I think, has that.

Two pretty good answers. What do your hometown friends think of you?

I don't know. I ran into a hometown friend in Arizona this weekend, and he was just like, “Dude, it seems like you're having a good time. What do you even do? Is that really—? My friend said that's your Twitter account. What are you doing with this? You live in New York.”

I think I haven't kept up with most of them. The ones that I have kept up with, it's the same as it ever was. I think some of the best friendships, like with friends from high school, never change regardless of what goes on in each person's life.

All right, last one, and I'll ask you some cringe motivation, and then we'll call it. If you're, like, 30—I don't know, 35—with a billion dollars, like infinite money, what is the optimal place to live?

Wait, give me a second. Hold on, give me 5 seconds.

Okay, you're good.

Okay, I'm back. Could you repeat the question? Sorry.

Yeah.

I got a little anxiety.

If you're, like, 35, with a billion dollars, infinite money, what is the optimal place to live? Like peak, peak, peak, peak place to live.

I don't know, man. It's obviously personal. Do you like skiing? Live in a ski town. Do you like surfing? Live by the beach. I think multipolar is fun. I've been trying to find a place in Miami to rent. I've been unsuccessful so far, but I want to add that as a place. I spend time mostly between New York and California.

I think New York is amazing in the U.S. Outside the U.S., I'm under-traveled. I love Tokyo and a lot of other spots in Asia and Europe, and these things. But I don't know. It's nice to live somewhere where I grew up in the culture. The U.S. is amazing, obviously, and I speak the language.

But I think that's an answer for everyone, for themselves. I think having a few places that you bounce between is maybe underrated by old-school boomerism and probably overrated by our gen, but I do like it.

Old-school boomerism. Dude, I appreciate you doing it, man. I wasn't sure you would ever get the basics, because it's been a long time since you did one, so it's been... Bro, it's been fun to watch. Jenny Run, I think you're definitely one of the better posters on the app, and I appreciate when you come out and post what you're in, talk about why you made a trade, and why it played out a certain way.

A lot of people in the chat, myself included, really enjoy following it. It's kind of a brutal sign-off, but look, there are a lot of people who are trading who have not done as well as you have, or they're relatively new and haven't really figured it out yet. Even outside of trading, just young people in the world trying to position themselves: What do you do? And even information-flow-wise, how do you position yourself? What do you do over the next couple years where it does sort of have this overarching, you know, Loot and Rob type of long degeneracy, whatever it is, type of feeling?

So I'm curious. Thanks for doing it, and what do you tell people that they should do? How do they find their thing to do well and position themselves for where things are going?

Well, thank you very much. I'll return the compliments to you. I've been very impressed with how you kind of just kept it consistent through this show. It feels like you're kind of the big media presence to come out of our whole space, honestly, in this format. So I'm super sick and glad you had me on.

What I would say to that question is, you're never going to win at a video game if you don't really fuck with playing the video game. Nobody got insanely good who didn't really enjoy Call of Duty. I think if you're really young, you should spam a bunch of shit. Don't get too locked in. Try this, try that. It's like max shots on goal to find something, and then if you get any early signs of success—plus, even better than an early sign of success is just an early sign that you get addicted in a good way—then just press, press, press.

I think that's how I look at a lot of things. Things are done with experimentation, right? I had tried doing music production, then I had tried doing math research. Then I had tried being like, “Okay, I'm a blogger,” and then I'm like, “Okay, I do venture capital and I do poker.” Eventually, yeah, I just got lucky—early success in this NFT thing—and I really enjoyed it. I was like, “Okay, press, press, press. Let's see what happens.”

Eventually, you want to compound on something, right? But I think if you're really young, you have so much time, more than you think, and so much optionality, more than you think. You should take advantage of it, because you can discover for yourself and not have to choose what is cool.

Dude, despite the Twitter presence, you're a sneaky optimist, man. It's refreshing. You are.

I try to be. The Twitter is a whole other persona, you know?

That's your heart, man. You are. based16z, dude, absolute pleasure. Until 2030, when we get a part 2. Thanks again for coming on, dude.

Cheers. Thanks, Fred.