Odds on Open

Ethan Kho
  • 5.0 (1)
  • BUSINESS
  • UPDATED WEEKLY

Conversations with leading thinkers on trading and investing. Hosted by Ethan Kho. Produced by Patrick Kho.

  1. 6D AGO

    “I think of everything as a bet” - SIG Director Andrew Courtney

    Former Susquehanna International Group (SIG) Head Trader Andrew Courtney breaks down the reality of being a quant trader and market maker at one of the world's elite proprietary trading firms. He reveals what trading floors actually look like—multiple monitors covered with flashing numbers, signals, and price movements that traders analyze all day with zero lunch breaks and constant attention on market microstructure.  Andrew explains how SIG's legendary poker training culture shapes traders' ability to think probabilistically, make decisions under uncertainty, and justify every bet both quantitatively and qualitatively. He shares candid insights about who should (and shouldn't) pursue trading careers, the transition from floor trading to electronic markets, and how the tight-knit network at prop trading firms differs dramatically from consulting or investment banking paths. Andrew now runs Kalshinomics, a prediction markets analytics tool, and writes The Whirligig Bear on Substack where he analyzes opportunities in Kalshi, Polymarket, and emerging prediction market platforms. He goes deep on finding edge in prediction markets—from identifying inefficient markets with liquidity incentives to using ChatGPT and AI tools for handicapping obscure Grammy categories.  Andrew explains market efficiency frameworks, how to assess who you're trading against, and why some markets (like low-volume Grammy categories) offer better opportunities than hyped meme markets. He also tackles the casino-ification of America debate, insider trading concerns in prediction markets, and whether these platforms are a net good or bad for society. We also talk about... The real day-to-day of quant trading and market making at SIG: staring at screens all day, monitoring signals, and staying alert for when markets go off the railsWhy SIG's poker training program—playing for hours daily, turning over cards after every hand, and defending each decision quantitatively—builds world-class tradersHow thinking in bets becomes second nature and why Andrew now frames every decision (like private school vs public school) as an expected value calculationThe cultural differences between floor trading (loud voices, physical presence in the pit) versus upstairs electronic trading (surrounded by sharp peers and data)Why prop trading careers build narrow, dense networks compared to consulting or investment banking, and what that means for long-term career optionalityFinding edge in prediction markets: liquidity incentives, identifying who you're trading against, and why some markets are wildly inefficientTrading strategy and bet sizing: when to use Kelly criterion, how to scale into positions, and Bayesian updating based on how the market reacts to your tradesThe insider trading debate in prediction markets and why Andrew thinks it's corrosive to incentives, trust, and long-term market qualityRisk transfer opportunities: using prediction markets for insurance-like hedging (Florida hurricane risk, California earthquake exposure) rather than pure speculationWhether prediction markets are good for society: the value of probabilistic news context versus the risk of casino-ification and degenerate gamblingCareer advice for aspiring traders: evaluating if you can handle constant screen time, limited networks, and high-variance outcomesHow to apply expected value thinking to everyday life: insurance decisions, risk tolerance, and when not to over-optimize (don't EV calculate marriage)The future of prediction markets: institutional adoption, regulatory uncertainty, and whether amateurs can still compete before professionals crowd out edgeWhy Kalshinomics focuses on analytics and custom interfaces for serious traders rather than trying to be the "Bloomberg Terminal" of prediction marketsLessons from SIG on decision-making, probability, and building systems that extract signal from noise in high-frequency, high-stakes environments

    57 min

  2. FEB 5

    “Conviction is dangerous” - Emerging Markets Hedge Fund Manager Sinan Xin

    Sinan Xin manages an emerging markets tech hedge fund from New York, investing across China, Latin America, Southeast Asia, and beyond. In this conversation, he shares how he builds edge in some of the world's most volatile markets. We discuss: Why conviction can become bias—and how to tell the differenceBuilding durable relationships across geographies you're not fromThe evolution of edge: from reading 10-Qs at the library to AIWhy understanding your own behavior matters more than any toolHow to think about career decisions when everyone's chasing the same thingPortfolio construction strategies for managing emerging market risksWhy the best English-speaking management teams often underperformSinan explains how his background—born in China, raised in the US, working in tech M&A at Lehman Brothers before it collapsed—shaped his investment philosophy. He reveals how standing up a dropshipping website taught him about e-commerce software, why he visits cattle farms at 4am, and how private market relationships help him spot public market inflection points. The conversation turns personal as we explore career alpha vs. beta. Sinan pushes back on the idea that smart people should simply pick "the most liquid market" (like AI today), arguing that true edge comes from self-knowledge, not chasing prestigious outcomes. For anyone thinking about investing, careers, or how to build differentiated views in efficient markets, this is a masterclass in independent thinking.

    1 hr

  3. JAN 29

    “AI Makes Analysts Lazy” - Hedge Fund Manager Alix Pasquet on the Importance of Analog Training

    In this episode, hedge fund manager Alix returns to Odds on Open to tackle what he calls the most important problem facing young investors today: the complete loss of analog training skills that created the greatest investors of previous generations. Alix runs a hedge fund that deliberately avoids AI tools for analysts, believing they're "extremely dangerous" because they optimize analysts in ways that sub-optimize fund performance. He breaks down why creativity comes from constraints, not abundance—why getting to consensus faster with AI actually makes you worse at generating alpha. The core issues: Gen X is the last generation trained with analog tools, the "junior-senior problem" where hedge funds realize they don't need junior analysts anymore, the attention span crisis, and why Silicon Valley executives don't let their kids use the products they built. Alix introduces the "10K and a pencil" approach, inspectional reading techniques to extract 80% of a book's value, frameworks from Charlie Munger and Peter Kaufman, Art of War principles applied to predator-prey business dynamics, and why reading trains every critical investment skill—pattern recognition, visualization, reading between the lines, leaps of judgment.

    1h 23m

  4. JAN 22

    Why 20% of Hedge Funds Fail After One Year - Claudia Quintela on Why Managers Need Business Sense

    Disclaimer: This is not a financial promotion and must not be seen as advice, but only as an educational piece Cláudia Quintela has spent 25 years connecting early-stage hedge fund managers with institutional capital. She's worked across FX, macro, and systematic strategies at State Street, UBS, Morgan Stanley, and Blenheim Capital, one of the world's largest commodity managers at its peak. In 2017, she founded Vibe Advisors, an independent advisory boutique focused exclusively on helping emerging managers—particularly systematic, CTA, and macro funds—navigate the hardest part of launch: raising that first $50 to $200 million when you have limited track record, tight capacity constraints, and institutional investors demanding day-one infrastructure. She specialises in the messy reality of early-stage fundraising: fee pressure, seed negotiations, managed account structures, positioning for allocators who need to sell your strategy internally, and translating complex quant models into language that gets you through the door. Her client base skews heavily toward liquid macro and model-driven managers. Today, Cláudia runs a portfolio career: advising fund managers and investors, writing weekly about entrepreneurship and capital raising, hosting webinars on AI tools for investor relations and marketing automation, and speaking on panels about women in finance. She's an advocate for the sisterhood and believes the next generation of emerging managers will look different from the last. Based in London and originally from Porto, she holds an MSc in Finance from LSE and is a CFA charterholder. She's here to talk about what actually works when you're trying to raise institutional capital at the hardest stage—and how emerging managers can build smarter, leaner operations using the tools that didn't exist when she started.

    1h 6m

  5. JAN 15

    How I Built a 1.4-Billion-Dollar Quant Fund - Deepak Gurnani on Founding Versor Investments

    In November 2025, I hosted a fireside chat at Columbia University with Deepak Gurnani, founder of Versor Investments, a $1.4 billion [1] quantitative hedge fund based in New York with offices in New York and Mumbai. Deepak spent two decades at Investcorp, where he built and led the firm’s hedge fund division. In 2013, he stepped away to found Versor with a singular goal: to build a research-driven quantitative firm focused on leveraging alternative data. This conversation is a continuation of the story we began on Odds on Open with Nishant Gurnani and DeWayne Louis, two of Versor’s partners. In that episode, we explored the systematic strategies that Versor runs. In this fireside chat, we go upstream to understand how it all began. We talk about: - Deepak’s journey from IIT to Citigroup to Investcorp - How the hedge fund industry looked in the 1990s versus today - What it really takes to spin out and build a quant firm from scratch - Why Versor adopted cloud computing and alternative data years before most peers - How small firms compete with giants like Citadel, Millennium, and Jane Street - What Deepak looks for when hiring researchers - Why “value proposition” is the starting point for any new fund - The mindset required to build something that lasts Versor LinkedIn Page: https://www.linkedin.com/company/versorinvestments/ Research Repository (“Athenaeum”): https://www.versorinvest.com/athenaeum/ 1. Data as of December 31, 2024. AUM as per SEC definition for the purposes of item 5F on the ADV Part 1a. For important disclosures, please visit: https://www.versorinvest.com/terms-and-conditions/

    47 min

  6. JAN 12

    This Ex-Poker Pro Built a Hedge Fund by Betting Against Beta – David Orr on Asymmetric Bets

    Ethan Kho interviews David Orr, a former professional poker player turned hedge fund manager. They discuss David's journey from poker to founding Militia Capital, his investment philosophy, and the lessons learned from both industries. David shares insights on risk management, the importance of finding asymmetric bets, and the challenges of the hedge fund industry. He also offers advice for aspiring investors and reflects on the future of hedge funds.

    1h 3m

  7. JAN 12

    How Leading Multi Strat Funds Hire - Recruiting Director Jesse Skaff on the Hedge Fund Talent War

    Discover how top multi-manager hedge funds like Citadel and Millennium attract the brightest minds, the evolving talent strategies in the industry, and the unique traits that set successful candidates apart. Whether you're an aspiring finance professional or just curious about the inner workings of hedge funds, this episode offers valuable insights into the competitive landscape of financial services.

    49 min

  8. 12/28/2025

    How the World’s #1 Prediction Markets Trader Finds Edge! - Domer on Trading Global Political Events

    What’s the difference between prediction markets trading and equities trading? On Odds on Open, the world’s #1 prediction markets trader Domer explains how prediction markets work as a form of information-based trading, where news and signals can arrive at any moment, forcing continuous price discovery and repricing. Unlike stock markets, where returns often depend on long-term growth, valuation multiples, and market beta, prediction market strategy focuses on information timing, news flow, and market reaction to new data. Rather than forecasting final outcomes, traders focus on event-driven trading, short-term price movement, and probability trading, exploiting mispriced probabilities and trading event contracts instead of holding positions to resolution. This approach allows traders to generate expected value (EV) and highlights the difference between active trading vs passive investing.Domer also explains how many participants concentrate on high-volume headline markets, while traders look for prediction market edge in event contracts trading across smaller markets. On platforms like Polymarket and Kalshi, opportunities exist in alternative markets and micro events that are less crowded and prone to pricing errors. By specializing in specific market categories and focusing on liquidity, volume, and time horizon, traders can adjust position sizing and holding periods to match their edge. This approach mirrors quantitative trading and event-driven strategies, where domain knowledge and execution outperform broad speculation.Other subjects discussed...How prediction markets trading focuses on short-term price movement and active trading rather than holding event contracts to resolution.Prediction market strategy is based on exploiting mispriced probabilities to generate expected value (EV).Prediction market edge is most common in micro markets and sub-events with lower liquidity and attention.Event contracts trading rewards traders who identify information-driven repricing before markets adjust.Information-based trading in prediction markets reacts to discrete news rather than continuous market noise.Probability trading requires distinguishing mean reversion from true regime shifts after breaking news.Losses in prediction markets are often caused by crowded trades and poor position sizing, not direction.Position sizing must scale with edge and uncertainty to preserve long-term expected value (EV).Platforms like Polymarket and Kalshi allow large traders to temporarily distort prices.Capital concentration in alternative markets can create opportunity for smaller traders.Long-term success depends on repeatable decision-making rather than individual outcomes.Prediction markets exhibit less random variance than equities because prices move on information.Poker develops risk tolerance and variance management applicable to prediction markets trading.Regulation is likely to limit influenceable event contracts while allowing large markets to grow.

    1h 4m
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About

Conversations with leading thinkers on trading and investing. Hosted by Ethan Kho. Produced by Patrick Kho.

Information

  • Creator
    Ethan Kho
  • Years Active
    2025 - 2026
  • Episodes
    44
  • Rating
    Explicit
  • Copyright
    © Ethan Kho
  • Show Website
    Odds on Open

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