The Risk Takers Podcast You're Probably Underbetting...Here's How You Bet More | Ep 128
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Nov 5, 2025 Gamblers often underbet in crucial moments due to psychological barriers. The hosts discuss the impact of emotional pain on sizing up bets and how to strategically take large swings for potential big wins. They emphasize the need to identify one-off opportunities versus ongoing markets while addressing the parallels between dating sites and betting markets. Recent scandals and regulatory pressures in betting are also covered, alongside the benefits of low fees on platforms like Polymarket that could reshape market dynamics.
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Scale Up By Calibrating Your Edge
- Start sizing up with a conservative assumed edge and refine it by betting the market and collecting data.
- Use Kelly as a framework but calibrate assumptions and err conservatively on bankroll and edge estimates.
One-Time Spots Deserve Painful Sizing
- One-shot, short-lived edges require much larger sizing than you intuitively expect.
- If a losing bet wouldn't hurt, you probably bet too little in a true rort/one-time spot.
Account For Psychological Drawdowns
- Accept that Kelly-style swings will feel awful and size to personal tolerance for drawdowns.
- Avoid adding hidden conservatisms like an undersized declared bankroll or regressing the market without accounting for their effect.