Jake Ostrovskis 4.2 7 ideas

Head of OTC Trading, Wintermute
After 1 day
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5/15 min ideas
After 1 week
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5/15 min ideas
After 1 month
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5/15 min ideas
2 winning  /  3 losing  ·  5 positions (30d)
Net: -11.2%
By sector
Crypto
5 ideas -9.0%
Stock
2 ideas -20.1%
Top tickers (by frequency)
BTC 4 ideas
67% W -6.0%
MSTR 1 ideas
HYPE 1 ideas
0% W -18.0%
RIOT 1 ideas
0% W -20.1%
Best and worst calls
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.
BTC The Block Feb 03, 05:25
Head of OTC Trading at Wintermute
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.
HYPE The Block Feb 03, 05:25
Head of OTC Trading at Wintermute
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.
MSTR The Block Feb 03, 05:25
Head of OTC Trading at Wintermute
R
RIOT Jan 16, 15:34
January 16, 2026 at 15:34
Head of OTC Trading, Wintermute
Call buying for
BTC Jan 05, 21:04
January 05, 2026 at 21:04
Head of OTC Trading, Wintermute
The OCC letter from early-Dec has been re-circulating the last few days and allows banks to engage in "riskless principal" Crypto trades. This flow differs from a prop desk. In plain English: a bank
BTC Dec 29, 16:44
December 29, 2025 at 16:44
Head of OTC Trading, Wintermute
Increased overwriting
BTC Dec 26, 13:06
December 26, 2025 at 13:06
Head of OTC Trading, Wintermute
Jake Ostrovskis (Head of OTC Trading, Wintermute) | 7 trade ideas tracked | BTC, MSTR, HYPE, RIOT | Twitter, YouTube | Buzzberg