Investor Connect: Digital Asset Investing, Trend-Following Strategies, and the Age of Autonomy

Investor Connect: Digital Asset Investing, Trend-Following Strategies, and the Age of Autonomy

October 9, 2026 by investor

On this episode of Investor Connect, Hall welcomes Jake Ryan, Founder and Chief Investment Officer at Tradecraft Capital, a digital asset management firm focused on cryptocurrency, blockchain, and emerging technologies. Jake shares how he moved from software engineering and artificial intelligence into digital assets after early angel investing in a blockchain company and buying his first Bitcoin in 2016, and how his tech background helps him assess long-term project defensibility. 

He explains Tradecraft’s evolution from programmatic discretionary trading to more automated, quantitative trend-following strategies that can go long or short in a 24/7, highly correlated market. Jake discusses what traditional investors misunderstand about crypto adoption and regulation, how he thinks about valuation using revenue-based models and on-chain activity metrics, and his “age of autonomy” framework combining IoT, AI, robotics, and blockchain. He also covers volatility management through position sizing and multi-year duration, the rise of stablecoins, and tokenized real-world assets.

 

Visit Tradecraft Capital LLC at www.tradecraft.capital/

Reach out to Jake at www.linkedin.com/in/jakeryan/, and on x.com/TradecraftJake

 

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Disclaimer:
Hall T Martin is the director of Investor Connect, which is a 501(c)(3) nonprofit dedicated to the education of investors for early-stage funding. All opinions expressed by Hall and podcast guests are solely their own opinions and do not reflect the opinion of Investor Connect. This podcast is for informational purposes only and should not be relied upon for the basis of investment decisions.

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