On The Brink with Castle Island Weekly Roundup 09/26/25 (Tether worth $500b?, Cloudflare’s stablecoin, DAT insider trading) (EP.669)
10 snips
Sep 26, 2025 Matt and Nic dive into Tether's astounding potential $500 billion valuation and discuss its implications. They analyze Cloudflare's ambitious plan to launch a stablecoin for web payments and the challenges Circle faces with reversible transactions. The duo also highlights the SEC's investigation into nearly 200 digital asset trusts for insider trading, while examining the European banks' initiative to create a MiCA-compliant stablecoin. They tackle the impact of stablecoins on traditional banking and preview upcoming Senate hearings on crypto taxation.
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Coin Center Dinner Takeaways
- Matt and Nic described attending the Coin Center dinner and praised Hester Peirce's keynote as unusually strong and humorous.
- They recommended supporting Coin Center for its long-standing legal defense of blockchain users.
Tether Valuation Surprise
- Tether reportedly sought $20 billion at a $500 billion valuation, surprising Matt and Nic versus their prior estimates.
- The hosts noted that Tether's large Bitcoin and gold holdings complicate simple valuation comparisons.
Cloudflare's Agentic Payments Play
- Cloudflare announced a USD-backed 'Net Dollar' stablecoin and an X402 protocol to enable agentic web payments.
- Matt and Nic argued native web payments via stablecoins could simplify onboarding and enable micropayments for agents and devices.
