Bitcoin's Tax Future and Community Strength

This chapter explores the potential abolition of capital gains tax on Bitcoin, urging lawmakers to rethink its classification as a monetary asset. It discusses the growing interest of CEOs in Bitcoin, the impact of innovative financial strategies, and the significance of stablecoins within the cryptocurrency landscape. The speakers emphasize the resilience of Bitcoin amidst volatility and the importance of community connections and historical understanding for newcomers.

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My guest today is Caitlin Long, Founder and CEO of Custodia Bank, a 22-year Wall Street veteran, and one of the most influential voices in Bitcoin policy and financial regulation. A Harvard-trained lawyer and early Bitcoin advocate, Caitlin played a central role in turning Wyoming into the most crypto-friendly legal jurisdiction in the United States, helping pass over 20 blockchain-enabling laws. In this episode, Caitlin walks us through her ongoing legal battle with the Federal Reserve, the hidden mechanics of Operation Chokepoint 2.0, and why access to a Fed master account is the front line of financial freedom. We discuss the stablecoin wars, the surveillance threats of CBDCs, and how privacy, law, and innovation are colliding inside the US banking system. Above all, this is a conversation about fighting centralized control, defending open access to money, and building the legal rails for a Bitcoin-native financial future.

► This episode is part of the "Bitcoin Vegas 2025 Special" in collaboration with Ben Samocha, Founder of Israel’s CryptoJungle and Crypto Talks podcast.

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Caitlin’s Twitter: https://x.com/CaitlinLong_

Custodia Bank’s Website: https://custodiabank.com/

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