Momentum is Everything | Leigh Drogen on Building Lasting Strategies in Crypto

In this episode, we sit down with Leigh Drogen of StarKiller Capital, alongside guest co-host Kai Wu, for a deep dive into crypto investing strategies, momentum in digital assets, and market-neutral DeFi yield opportunities. Leigh shares his perspective on where we are in the crypto evolution, the parallels with past technology cycles, and how to survive and advance in one of the most volatile asset classes in the world. From time-series and cross-sectional momentum to the economics of yield farming, this is a comprehensive look at building systematic strategies in digital assets. Topics Covered: The parallels between Web1 → Web2 and today’s crypto transition Why the “fat protocol” thesis is giving way to the “fat app” era The role of Bitcoin vs. Ethereum in the next stage of crypto adoption The “survive and advance” investing philosophy Time-series momentum and cross-sectional momentum in crypto How VC behavior is changing momentum dynamics Sector-level momentum and narrowing lookback periods StarKiller’s approach to asset selection and quality screens Building a market-neutral DeFi yield strategy Bootstrapping network effects and early liquidity provisioning Diligence, counterparty risk, and managing protocol risk The competitive landscape and where the biggest edges remain in crypto Timestamps: 00:00 – Crypto’s infrastructure milestones and evolution 02:53 – The “fat protocol” vs. “fat app” thesis 08:09 – Bitcoin’s role vs. Ethereum’s potential 14:20 – “Survive and advance” and limiting drawdowns 19:20 – Time-series vs. cross-sectional momentum 23:00 – VC selling behavior and regime change in momentum 31:47 – Sector-level momentum trends 36:13 – Shorter lookback periods and market speed 39:56 – StarKiller’s investable universe and filtering process 48:00 – Designing a market-neutral DeFi yield strategy 52:56 – Rewards farming and bootstrapping network effects 58:00 – Market-making vaults and APR opportunities 01:00:10 – Managing counterparty and protocol risk 01:04:02 – Has crypto alpha become more competitive? 01:07:41 – One lesson for the average investor