On The Brink with Castle Island

Weekly Roundup 01/02/26 (2026 predictions, wealth taxes, secret insolvencies) (EP.694)

30 snips
Jan 2, 2026
In their first show of 2026, Matt shares hilarious tales of building a backyard ice rink. They dive into the implications of the draft Digital Asset Parity Act, dissecting wealth taxes and their impact on innovation. Bold predictions include a potential secret exchange insolvency and major moves in prediction markets amid insider trading risks. Discussions touch on a consortium of US banks creating a stablecoin and the evolving threat of quantum computing to Bitcoin. Plus, a nostalgic look at Kickstarter highlights the future of crowdfunding with tokenized equity.
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ANECDOTE

Backyard Ice Rink Project

  • Matt Walsh built a backyard ice rink and struggled with leaks and nightly maintenance.
  • He uses warm water and a big squeegee to resurface it, calling it a whole production.
INSIGHT

Big Players Enter Prediction Markets

  • Coinbase acquired The Clearing Company to enter prediction markets and challenge incumbents.
  • Retail order flow and brand give Coinbase and Robinhood a customer-acquisition advantage.
ADVICE

Monitor Infrastructure Fundraises

  • Watch for centralized perpetuals and payments infrastructure raising capital as on-ramps expand.
  • Track firms like Architect, Coinbacks, and Rocket for infrastructure trends.
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