You Can Do Everything Right And Still Lose Bitcoin
You Can Do Everything Right And Still Lose Bitcoin  
Podcast: The Wolf Of All Streets
Published On: Sun Nov 08 2026
Description: What happens when you follow the advice for securing your Bitcoin and still lose it? Nathan McCauley, co-founder and CEO of Anchorage Digital, joins me to explain why protecting Bitcoin is becoming more complicated, even for people who use hardware wallets and follow established security practices. Nathan tells the story of a friend who lost Bitcoin despite taking the precautions he believed were necessary. We discuss why self-custody remains essential for financial freedom, why banks may eventually provide easier custody for most people, and how AI is changing both cyberattacks and the defenses against them. We also explore the next generation of financial infrastructure: AI agents with bank accounts, human-controlled spending limits, and access to cash, cards and crypto. Nathan explains why stablecoins will matter without necessarily becoming the payment method for everything, and why responsibility for AI-driven financial mistakes remains unsettled. Kalshi – Trade crypto with leverage in America Trade $50, Get $25 bonus: kalshi.com/p/WOAS Learn more about your ad choices. Visit megaphone.fm/adchoices