Odds on Open

Matt Schrager, a TD Quant and former Headlands trader who built systematic market making for municipal bonds, walks through muni microstructure and why illiquid fixed income needs probabilistic pricing. He discusses adapting HFT simulation to rare trades. He explores inventory management, scaling prop trading into a bank, finding edge in gnarly markets, and how AI and talent shift the game.

A deep dive into what creates trading edge and institutional credibility in hedge funds. They argue markets are driven by participant incentives rather than randomness. Discussion covers pod-shop advantages, why new trading ideas are scarce, the dangers of short-volatility “gamma” traps, and the practical economics of running and proving a fund.

Sean Emory, an investment manager at Avery who blends data and fundamentals, talks about using alternative datasets like app-store metrics to spot inflection points early. He explains systematizing signals, tracking theses over quarters, and why concentrated portfolios can outperform. Conversation also covers the Six Ms risk framework, AI’s impact on market efficiency, and practical lessons from launching an active ETF.

Scott Phillips, quant trader and founder/CEO of HyperTrend, builds systematic on-chain trading systems to exploit crypto inefficiencies. He explains why simple trend, momentum and carry strategies can yield outsized Sharpe, how price-insensitive holders and VC exits create predictable pressure, and the operational risks and venue choices that shape mid-frequency crypto edge.

Brett Caughran, founder of Fundamental Edge and former PM at Tiger Cub and multi-manager firms, discusses frameworks like ETIC and the Focus 5. He explores how AI reshapes research, why volatility creates opportunities for fundamental investors, and how junior analysts must evolve from data entry to primary research and AI orchestration.

Derek Pilecki, founder of Gator Capital Management and specialist investor in financials, shares how he finds edge in regional banks, brokerages, insurance and info-services. He explains spotting real business change vs market noise. Topics include position sizing and adding to winners, post‑GFC underwriting dynamics, private credit tail risks, AI’s impact on valuation, and scaling concentrated portfolios.

Matei Zatreanu, founder of System2 and data/AI operator for hedge funds, blends generative models with expert-network automation. He breaks down LLM customization, automating qualitative interviews, causal mapping of second-order macro effects, and why top managers treat investing as a craft. The talk also covers talent constraints, multi-manager platforms, and bespoke high-end research services.

Greg Newman, founder and CEO of Onyx Capital Group and a leading oil derivatives market-maker, shares how liquidity providers navigated a market breakdown. He discusses why outright prices mislead, the shift to manual pricing and time spreads, reading physical players like refiners and airlines, and using options flow and off-hours order flow as superior signals.

Annie Duke, legendary poker champion and decision scientist, offers a lively tour of decision-making under uncertainty. She explains bets as resource allocations and why judging choices by outcomes is misleading. Topics include expected value thinking for careers and startups, using base rates and reference classes, mental time travel to reduce discounting, and balancing luck with process.

Zachary A. Levitt, founder and manager of a capacity-constrained multi-manager fund focused on niche relative-value and arbitrage strategies. He explains screening for repeatable niche PMs, inverse-vol weighting with discretionary overlays, sizing around micro-regimes, and running a lean, performance-aligned platform that targets liquidity gaps ignored by larger funds.