Investor Identity
John is a crypto investor with an unusually boring strategy, and he means that as a compliment.
Buy high-quality digital assets, hold them for years while the rest of the market discovers what he already figured out. Don't do much else.
He knows this means missing opportunities. He's fine with it. As he puts it: “Chasing every opportunity means you miss most of them.”
His investing philosophy comes from King Solomon, which is not a sentence you read often in crypto:
“Buy the truth and sell it not.” -Proverbs 23:23
Where he plays
Bitcoin and Ethereum first, with the rest of the crypto market as a smaller, more opportunistic allocation. He believes there's still real underappreciated value across altcoins. He just isn't willing to bet the portfolio on it.
Background
John is the host of Milk Road Macro and a digital asset investor focused on long-term value creation in crypto markets.
Credentials:
- General Partner and Head of Research at TRU Capital
- Relationship Manager & Digital Asset Strategy Advisor at Iniativ Equity Partners
- Digital Asset Consultant
- Former Vice President of Client Services and Relationship Management at Aladdin by BlackRock
- Former Writer for Discover Crypto
Portfolio Structure
How he invests
3 to 10 positions, heavily concentrated in Bitcoin and Ethereum, and no limit to how much cash he holds (it all depends on his market outlook).
Bitcoin and Ethereum are three-year-plus holds. Altcoin trades can be shorter, within a cycle.
No leverage. No speculative trading. Spot crypto, held with conviction, and that's the entire mechanism.
He also has a rule for handling drawdowns that's mostly about managing himself: hold, post Batman GIFs on X, and wait. If something drops 25 to 30% and nothing has actually changed except that people are scared, that's the opportunity. But he waits for confirmation first. Don't try and catch a falling knife.
What he's looking for (and what he avoids)
Four questions, in order:
- Are we in a Bitcoin bull market? If not, be patient.
- Is the market undervaluing this asset based on demand, revenue, or some other number you can actually point at?
- Did a genuinely strong project just take a sentiment hit for reasons unrelated to the project? Think Solana crashing after FTX blew up.
- If yes, accumulate and hold for years while the market figures it out.
He focuses far more on buying the bottom than selling the top. Dollar-cost average in, dollar-cost average out. When your stomach drops and there's blood in the streets, buy. When you feel euphoric and want to screenshot your portfolio, sell.
The hard nos are short: no leverage, no memecoins, no meme stocks, no panic selling, and no calling the top.
He takes a little profit every cycle, quietly, on big green days deep into a bull market. If a blow-off top shows up and a bunch of on-chain indicators fire at once, he'll sell a bit more. He wants a confluence of signals, never just one.
Two rules he lives by: don't trade on emotion, and don't sell winners to buy losers.