On The Brink with Castle Island
Weekly Roundup 12/05/25 (The Trouble with Taproot, a Prediction Market Paradox, HFSC OCP.2 Report) (EP.689)
AI Summary
Matt Walsh and Nic Carter review the week’s blockchain headlines, flagging lingering quantum‑risk concerns and questioning whether banks are infiltrated by intelligence agencies. They dissect technical and regulatory issues—from problematic Taproot address handling and MicroStrategy’s USD reserve strategy to Kalshi’s move onto chain and the paradoxes of prediction markets, including potential insider‑trading on Polymarket. The episode also covers Vanguard’s new Bitcoin ETFs, the House Financial Services Committee’s OCP 2.0 report, rising crypto leverage, and the looming threat of AI agents exploiting crypto systems, with a skeptical nod to Eliezer Yudkowski’s influence.
Episode Description
Matt and Nic are back with another week of news and deals. In this episode:
Quantum risk again
Are banks filled with spooks?
The trouble with Taproot addresses
Microstrategy's dollar reserve
Kalshi is going on chain
Prediction market predicaments
Are insiders monetizing Google search information on Polymarket?
Are prediction markets insider trading machines by definition?
DAT activist fights
Vanguard adds Bitcoin ETFs
House Financial Services Committee releases their final report on OCP2.0
What's going on with leverage in crypto?
Are AI agents going to start stealing crypto?
Is Eliezer Yudkowski to be trusted?
AI is going to usher in the golden age of fraud
Show Notes
On The Brink with Castle Island
Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)
Hosts: Matt Walsh and Nic Carter (Castle Island Ventures)
Publication date: December 5, 2025
Episode summary
Matt and Nic are back with another week of news and deals. In this episode they discuss:
-
Quantum risk again
-
Are banks filled with spooks?
-
The trouble with Taproot addresses
-
MicroStrategy’s dollar reserve
-
Kalshi is going on chain
-
Prediction market predicaments
-
Are insiders monetizing Google search information on Polymarket?
-
Are prediction markets insider‑trading machines by definition?
-
DAT activist fights
-
Vanguard adds Bitcoin ETFs
-
House Financial Services Committee releases its final report on OCP 2.0
-
What’s going on with leverage in crypto?
-
Are AI agents going to start stealing crypto?
-
Is Eliezer Yudkowski to be trusted?
-
AI is going to usher in the golden age of fraud
About the podcast
Hosts Matt Walsh and Nic Carter of Castle Island Ventures explore news and deals in the public‑blockchain space and talk to leading experts in the industry. Learn more and stay up to date at CastleIsland.vc and follow on Twitter @CastleIslandVC.
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