Jake Ostroskis — Head of OTC Trading at Wintermute (3 trade ideas)

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Date Ticker Direction Thesis Source
Feb 03, 2026 WATCH Bitcoin is currently trading strictly on the "Momentum Factor." It is not trading as a debasement hedge (Gold) or a risk-off asset. Since BTC is effectively a high-beta proxy for the Nasdaq, the primary risk is a rotation out of Tech/AI stocks (e.g., if Microsoft or NVIDIA roll over). If the "juice comes out of the AI trade," crypto will suffer a correlated drawdown regardless of its own fundamentals. WATCH Nasdaq and AI equities. If Tech momentum breaks, SHORT/AVOID Crypto. A sudden geopolitical shock could briefly flip BTC back to a "digital gold" correlation, invalidating the tech-beta thesis. The Block
Prediction markets and permissionless perps o...
Feb 03, 2026 LONG Hyperliquid is launching HIP-3 (Permissionless Perps for RWAs like Silver/Stocks) and HIP-4 (Prediction Markets). The chain is generating significant volume and fees, yet is considered "undervalued" relative to peers. In a market starved of organic yield, protocols with "genuine revenue" and "buyback mechanisms" become the only defensible investments for institutional committees. Hyperliquid's speed of execution (bypassing slow DAO governance) allows it to capture market share from slower incumbents like PolyMarket or Coinbase. LONG the ecosystem/token. It is the "only exciting thing" in the current market structure. Regulatory crackdown on permissionless derivatives; technical failure in oracle pricing for RWAs during off-market hours. The Block
Prediction markets and permissionless perps o...
Feb 03, 2026 LONG MicroStrategy (MSTR) has a massive USD balance sheet and can service its debt. Conversely, smaller "Digital Asset Treasury" companies are sitting on unrealized losses and are trading below their average purchase price. The "Treasury" model relies on reflexivity: stock price goes up -> raise cash -> buy coin -> coin goes up. On the way down, this breaks. Smaller players may be forced into a "death spiral" where they must sell assets to survive, crushing their stock. MSTR is capitalized enough to survive; the others are not. LONG MSTR (Flight to quality/liquidity), AVOID small-cap crypto treasury stocks. Bitcoin price drops by 50%, putting even MSTR under pressure. The Block
Prediction markets and permissionless perps o...