On The Brink with Castle Island

Weekly Roundup 08/15/25 (DAT fine print, stablecoin L1s, banks vs stables) (EP.656)

11 snips
Aug 15, 2025
Join Matt and Nic as they dive into the latest in crypto, discussing the nuances of Digital Asset Tokens and their market implications. Hear about Stripe and Circle's new stablecoin Layer 1s and the irony surrounding Stripe's entry. Reflect on Do Kwon's plea deal, the potential fallout of a 51% attack on Monero, and complaints about stablecoin yields. They also explore the challenges of traditional banks in adapting to the evolving landscape of digital assets while sharing a light-hearted take on breakfast cereals along the way.
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ANECDOTE

Fundraising Frenzy And Tokenized Whiskey Jokes

  • Hosts recount a wave of fundraising for crypto treasury companies, including Heritage Distilling and large DAT raises.
  • They use playful comparisons to tokenized whiskey and mezcal investments to illustrate the frenzy.
INSIGHT

DATs Hide Substantial Fee Leakage

  • Digital asset treasuries (DATs) often act like closed-end funds with significant fee leakage to managers.
  • BitMEX/hosts highlight hidden long-term advisory fees and option grants that can materially reduce investor returns.
ADVICE

Read SEC Filings Before Buying DATs

  • Read SEC filings and schedules carefully before buying DAT shares to find multi-decade fee commitments.
  • Avoid DATs with long advisory fee terms or minimum guaranteed manager payments that cannibalize returns.
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