On The Brink with Castle Island

Weekly Roundup 10/31/25 (DATs selling coins, prediction market problems, Bessent's pesos) (EP.681)

Oct 31, 2025
This week, the hosts dive into Mastercard's $2 billion acquisition of Zerohash and Fiserv's staggering stock drop, hinting at regional banking pressures. They explore Bitwise's Solana staking ETF launch and question the fate of DATs amid asset sales. A discussion on the questionable legality of prediction markets leads to insights about the structural challenges they face. The hosts also reflect on historical financial crises, Scott Bessent's savvy peso trade, the crisis in Venezuela, and revisit the Iran-Contra scandal.
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INSIGHT

Mastercard Validates Stablecoin Infrastructure

  • Mastercard's acquisition of ZeroHash signals major legacy payment firms committing to stablecoin infrastructure.
  • Stablecoin deals dominated venture activity this week, showing clear industry prioritization.
INSIGHT

Fiserv's Earnings Reveal Bank Exposure

  • Fiserv's stock plunged after weak earnings, revealing vulnerability in fintech incumbents.
  • Their client base of regional banks may amplify downside during regional banking stress.
ADVICE

Align Asset Trading With NAV

  • DAT issuers should sell assets when trading at premiums and buy when trading at discounts to align NAV with shares.
  • Failing to set realistic expectations invites legal and market backlash.
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