Chris Burniske Taught Me a Valuable Lesson About Crypto Investing I Wasn’t Expecting To Hear.
"Anticipate your future emotions now so you don’t make a stupid decision later."
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Direct 1-2-1 access.
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If you want the inside track, you’ll find it by visting my store:
Chris Burniske is one of the sharpest and most respected thinkers in the crypto space.
He also happens to be a nonchalant surfer with, and I mean this genuinely, a surprisingly refreshing level of insight that underpins his investing philosophy:
“When I’m looking for a spot to surf on any given day, I’m always looking for the best spot that has the fewest number of people, because I’m not going out there to compete with other people. I’m going out there to ride a wave. I want to be intellectually drawn to certain projects, and I want to ride that wave, and not so much get distracted by a wave that has hundreds of thousands of people on it.”
With how knee deep I am into NFTs, SUI, and now PNKSTR, this message couldn’t resonate more.
You have to be intellectually honest with yourself and look a few steps ahead to spot these opportunities, especially in the places people aren’t surfing.
Back when I was a normie stock investor, I always wondered how folks managed to get into assets so early, right at the ground floor. What the heck were they seeing? I’d hear their mythical “gates-to-Valhalla” stories, nearly fall off my chair, and then immediately brush it off as “right time, right place”.
People love to assume these public figures aren’t “market buying” like the rest of us, that they’re insiders operating in VC cheat mode. But that couldn’t be further from the truth.
Burniske was very public about scooping up Solana in 2022, right after the FTX debacle sent it from $247 down to $8.
He was stepping in with size around when SOL was at the $10 mark.
“Still longing $SOL while haters spinelessly pile onto the downside momentum. When ‘solana’ recovers, it’s not me who’ll be haunted by the thought, ‘Instead of jeering, I could have been buying $SOL at ~$10.’”
Despite the excuses on the timeline today, the investing opportunity and landscape are the same for all.
You can buy crypto tokens on the market, which may or may not be good investments. You’re essentially an unqualified angel investor (by traditional standards), with massive potential on the upside and equally brutal downside risk.
But it’s the upside that sucks you in like a riptide you didn’t see coming, because the potential is too monstrous to ignore.
Chris Burniske once said if something in Crypto gives you an “allergic reaction”, NFTs, meme coins, whatever it is, that’s exactly the thing you should look into more deeply.
Lean into it.
Because while you’re feeling intensity in a negative direction, someone else is feeling that same intensity in a positive direction.
Buckle up and let’s get into it.
The when-to-buy, when-to-sell framework in Crypto you’ve never heard before.
In 2014, Burniske had a total savings pot of $10,000.
He committed roughly $5,000, about half his liquid net worth, to Bitcoin at an average cost basis of $300 to $500 per BTC, while sitting at his kitchen table in New York.
When Bitcoin later crashed to $200 during the Mt. Gox collapse and the wave of regulatory FUD, he held his ground. He saw the volatility as a feature, not a flaw, and his investment as an asymmetric bet with a downside of losing some savings and an upside of 100x.
By late 2017, when BTC crossed $20,000, that $5,000 had grown into more than $300,000.
He calls this his pivotal origin story because it exposed the fallacy of waiting for “proof” in young, fast-moving markets. As he puts it, you don’t try to time conviction. “You size it small enough to survive the catastrophic drawdowns.”
That’s been the bellwether of his investing career.
Make modest bets on high-conviction ideas when most people are still doubting them. But it’s his recent comments about the current crypto market that taught me a valuable lesson I wasn’t expecting to hear.
He’s been urging his close friends to follow a simple framework he uses to bring clarity to their portfolio management.
It’s his framework for when to buy and when to sell:
Okay, let’s say you sell here, right? How are you going to feel? How good are you going to feel if it goes down versus how bad are you going to feel if it goes up?
Now let’s say you don’t sell. If you don’t sell, how good are you going to feel if it goes up versus how bad are you going to feel if it goes down?
Use that quadrant, because you can compare the good and the good, and the bad and the bad. The feeling for opposite actions and opposite market moves.
You don’t want to be too emotional, but for me, I think it helps people think about where they would experience more emotion or remorse or regret.
Just anticipating that future reality so that they don’t do something stupid in the future. And I think for a rational investor, somebody who’s careful about trying to build wealth, that matrix works well.”
The biggest mistakes in Crypto come from one thing.
It’s overriding a macro framework with emotion.
One of the biggest lessons from my eight years in crypto came from something Raoul Pal said, and it’s been glued to my brain ever since: “If you ever override a macro framework with emotion, you will come unstuck.”
The apparent confusion at the moment is that people are using the 4-year business cycle rather than the ISM business conditions index.
So, the price going down (which, granted, is painful) is letting emotion creep in.
I always find the best approach is to sit in this delta-neutral spot mentally and not let extreme emotion creep in either way.
Chris Burniske nails this, but in a way I had never heard before.
“I think the first thing to recognise is that a super-cycle narrative is a symptom of euphoria. It’s actually something that I would look for as confirmation for me that strengthens my conviction that something’s not right. It doesn’t make it harder for me to be bearish, it makes it easier. And I think that’s an important unlock that a lot of people have to go through: not feeling the tug of really strong momentum at extreme moments of the market, either bull or bear, but instead seeing how strong that momentum or that tug is. It’s euphoria at the top, it’s hysteria at the bottom, and you use that as the marker or the confirmation that something’s not right and it’s not going to last forever in the direction everyone is saying it’s going to last.”
A top signal in Crypto most will never see.
Burniske has a fascinating, very first-principles way of spotting when a market cycle is ending.
He often gets quizzed on podcasts about how he correctly called the top in 2021, and it came down to a mix of factors, some of the most interesting I’ve heard.
One was the rise of new coins on the charts, which fuels a “supercycle” narrative in one direction and usually triggers people to do the exact opposite.
But there was another factor he mentioned that I wasn’t expecting at all.
Chris Burniske (reflecting on 2021):
“First, there’s the super-cycle narrative. That’s a symptom of euphoria.
Then you look at the charts: they’re parabolic on the new names. And people are saying, oh, well, BTC and ETH aren’t quite parabolic, but the thing is — and this is where it helps to have been in crypto for a long time — you understand the maturity of these assets. You know that as they get bigger, as they get more liquid, they’re going to move a little less.
So BTC will move the least, then ETH, then probably next cycle SOL. And you start to understand the risk spectrum in that way. But we were seeing parabolic prices.
Something I was seeing on the venture side was that innovation was slowing while deal pace was increasing. Basically frantic deal pace, where people are like, nice to meet you, we closed yesterday, kind of thing.
And even the ways entrepreneurs treat VCs changes bear to bull. In a bull, you’ll have a lot more entitled behaviour from entrepreneurs. And I think the important thing for a VC in a bear is to not pay it back by being entitled — because the balance of power swings. In a bull, the entrepreneur has all the power. In a bear, the VC has a lot of power.
So just observing more bad entrepreneur behaviour — or just uncouth entrepreneur behaviour — that was happening a lot into late 2021. There were a ton of markers.
When you have a crazy convergence of things like that, it’s a very strong indicator. I’m never using one indicator.”
Final Thoughts.
The core lesson is this: the most significant opportunities in Crypto show up long before the crowd arrives or when they’re heading for exits.
And the only way to spot them is to resist bias, avoid emotional thinking, and lean into the assets or ideas your instinct initially wants to dismiss.
Most people do the opposite.
They shake their fists at the sky instead of doubling down on their education or their highest-conviction assets because the astronomical upside comes with downside volatility.
It’s a product and a feature of the space, not necessarily a risk.
Right now, the market is caught in a tug-of-war. On one side, you’ve got the memetics of people clinging to the four-year cycle and convincing themselves that now is the time to sell.
On the other side, you’ve got a backdrop of improving financial conditions.
And if we take Chris’ final point, we’re in a market where VCs hold the power, and founders are back to being boots-on-the-ground instead of riding euphoria.
No new coins are going parabolic as Solana, Luna, or Avalanche did in the last cycle. Nothing in the sentiment on the timeline suggests euphoria. In fact, it feels like the opposite. And when it feels like the end, that’s often the moment you want to lean into the opposite side of the bet.
Be drawn to projects the same way you’d be drawn to the best waves, the ones with the fewest people on them. Let yourself be intellectually drawn to specific ideas, but keep your position small enough that you can survive any period of decline.
I recently had a technical analysis call with an expert trader who walked through the last bear market. FTX collapsing, Luna imploding, banks going under, and an actual real-life bank run with mom-and-pop investors queuing down the street, all had people screaming that was the end for Crypto. That bear market lasted six months.
So while people think it’s apocalyptic out here, these things do not last.
I really like Chris Burniske’s regret-or-remorse model because it gives you a mental framework that helps you feel better about your decisions, even if it’s not the perfect time to sell. Because let’s face it, you’re not going to truly know. So it just needs to be right for you.
My take probabilistically is that we may have a short period of decline here, maybe into early next year, but the macro backdrop is incredibly strong.
Improving business conditions are the most significant driver of asset prices. And if that doesn’t end up being true, it would mean the most critical factors in markets, since markets began, suddenly no longer work.
The only thing you can do is anticipate your future emotions now so you don’t make a stupid decision later.
I’ve now opened a digital store with two things people keep asking for:
Direct 1-2-1 access.
The full breakdown of the assets I’m personally investing in.
If you want the inside track, you’ll find it here:
Powerful observations!
Useful advice. My core holdings have a time horizon for a couple decades, so I don’t care whatsoever about short term volatility. For my play money gambling, I don’t care if they go to zero which many have lol.