The Risk Takers Podcast Building an Unexploitable Betting & Trolling Strategy w/ The Shipper | Ep 121
Sep 17, 2025
Join The Shipper, a professional bettor and former PointsBet trader, as he shares his insider experiences on account longevity and priming strategies. He advocates for a poker-style bluffing technique in betting, highlights the competitive edge of team collaborations, and offers insights into building your own betting models. The Shipper also humorously critiques today's betting landscape and reveals the art of Twitter trolling with silent retweets. With stories of market exploits and the future of sports betting, his expertise is both enlightening and entertaining.
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Startup Trading Trains Real-World Skills
- Working as a trader at a disorganized startup-internal book teaches more practical skills than formal programs.
- The chaos forced traders to touch risk, pricing, live models, feeds and promos, accelerating learning.
Randomness Beats Pure Automation
- Human traders and timing matter more than pure automation when spotting sharp bettors.
- Introducing randomness into books' rules makes advantage play much harder to exploit.
Courtside Blackjack Rebate Exploit
- A customer gambled a million dollars at a casino while courtside to trigger a promo rebate.
- That player exploited host rebates and cost the book roughly $400k before being caught.