On The Brink with Castle Island Weekly Roundup 09/05/25 (Stripe’s Tempo, NASDAQ tightens rules on DATs, WLF vs Sun) (EP.663)
6 snips
Sep 5, 2025 Matt and Nic dive into the latest buzz, from discussing the US Open to unraveling the Clippers scandal. They tackle the intricate world of fantasy football strategies and the evolving landscape of betting markets, questioning if prediction markets really outshine traditional bookies. The duo also delves into the implications of NASDAQ's new rules, Galaxy's tokenized stock launch, and Stripe's Tempo L1. Plus, they explore the curious case of Kawhi Leonard's endorsement amidst salary cap violations.
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Tennis As Part Of The Social Circuit
- Nic attended the US Open and found the social circuit aspect striking and exhausting.
- He prefers avoiding the roving elite circuit and values distance from constant exposure to richer people.
Kawhi And The Aspiration Investigation
- Matt described Pablo Torre's reporting on Aspiration and Kawhi Leonard's alleged no-show payments as a deep-dive investigation into filings.
- The payments could be salary-cap circumvention and would be severe for the Clippers if proven.
Use AI To Improve Fantasy Drafting
- Nic used AI to draft his fantasy football team and expects better results than auto-draft.
- He suggests leveraging AI as an alternative to passive auto-drafting to potentially outperform human competitors.