Trend-Following in Crypto: Jake Ryan on Digital Asset Investing
Key points
Key takeaways from Investor Connect interview with Tradecraft Capital founder and chief investment officer Jake Ryan (October 2026):
From software engineering to Bitcoin. Ryan angel-invested in a blockchain company before buying any cryptocurrency, then bought his first three Bitcoin in 2016 at around $675 each — drawn in by a network that could not be killed after repeated incidents, and by smart contracts and immutability on Ethereum.
Multistrategy shift to quant. Tradecraft Capital moved from a programmatic-discretionary approach to an automated, quantitative trend-following strategy that uses four or five indicators and trades long or short, because digital assets are so highly correlated that asset selection lost its edge and market timing became the main source of returns.
Risk management is position sizing and duration. In a volatile asset class, he would neither make digital assets a majority of a portfolio nor hold none, and he advises holding for three or more years to ride Bitcoin's roughly four-year cycle.
Bitcoin is gold, stablecoins are silver. Bitcoin is held as a store of value rather than a medium of exchange, while stablecoins now carry most day-to-day economic transfers — a modern echo of the gold-and-silver split of the past.
The age of autonomy. A new long-wave economic cycle is being driven by sensors, AI, robotics and blockchain, shifting the edge from information and specialised knowledge to autonomous operations in both the physical and digital realms.
Adoption is earlier than it looks. Trading accounts in 2025 were comparable to email accounts in 1997, and the asset class has not yet had its killer-app moment, though regulation improved under the current administration and the Clarity Act could unlock token structure changes.
What's next. Tokenised real-world assets, with Ethereum the likely base layer from a traditional-finance perspective, plus machine-to-machine transactions and AI agents trading; meanwhile he cautions against stereotypes linking crypto to criminal activity.
Read more: Investor Connect
