Trading Crypto Markets With Cheshire

Markets have shifted: update your toolkit, size trades by conviction, and focus where you have a repeatable edge to survive and profit across crypto and TradFi regimes.

Key Takeaways

Choose markets and strategies where you have a real edge; exploit them until they decay, then shift markets, scale resources, or stop—competition quickly compresses returns.
Continuously update your toolkit: add complementary strategies, learn others' methods, and trade lower timeframes when higher-timeframe conviction is weak to get more reps.
Size positions by conviction: medium ideas ~50 bps, high conviction 200–500 bps; use natural stops, reduce sizes when strategies underperform, and increase when they perform.
Treat sentiment, funding, and order-book signals as context—not sole triggers—use sentiment mainly at bottoms; many simple signals have decayed since ETF launches.
Monitor TradFi relative-value indicators and flows: tightened BTC–IGV correlations, miner capex selling, and ETF marginal buying; a true bullish case needs Bitcoin to decouple.
Prioritize longevity and drawdown management over one-hit glory: know your risk appetite and time horizon, preserve capital, and compound returns across regimes.

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