Self-Custody for You and Your AI | Roland Bewick
âWith 12 words, you can travel the world. Your money arrives in the country before you do. It cannot be taken from you.â Roland Bewick builds the software that makes that sentence trueâand just taught an AI agent to do the same thing. Episode Summary Most Bitcoin wallets promise self-custody but keep offering the easy custodial shortcut. Alby killed theirs. In January 2025, the team shut down a custodial wallet processing over a million transactions a month and told users, Run your own node orâŚ
Your Data's Already Gone. Now What? | James Lee
âYou cannot have data compromised that you do not have.â James Lee has spent two decades watching breach transparency collapseâfrom near-total disclosure in 2020 to just 30 percent today. The president of the nation's leading identity crime nonprofit breaks down why your Social Security number is worthless on the black market. Why your driver's license isn't and what individuals can actually do when the system designed to protect them has already failed. Episode Summary James Lee has seen theâŚ
Your Money, Your Data, Your Mind | Jesse Posner
âIf somebody gets control over your personal AI â all your health data, all your financial data, all your emails, everything you've thought about â they own you.â Jesse Posner built FROST threshold signatures and shipped BitKey at Block. Now he's building Vora because he realized individual self-custody is still a LARP â and the stakes are about to get much higher. Episode Summary Most people think a hardware wallet means they've solved self-custody. Jesse Posner spent years at Coinbase andâŚ
S03E03 Aaron van Wirdum â Bitcoin's Origin Story and the Unfinished Fight
âThe cypherpunks who tried to build digital cash before Bitcoin might one day be remembered like America's founding fathers.â Aaron van Wirdum spent five years writing The Genesis Bookâand warns the fight for money outside of government control isn't over. EPISODE SUMMARY Bitcoin didn't appear from nowhere. For decades before Satoshi, a scrappy band of cryptographers, privacy activists, and heterodox economists tried to build digital cash that could operate outside government control. They allâŚ
S03E02 Jason Hughey â Companies Don't Keep Promises. People Do.
Enron had âintegrityâ as a core value. FTX had none at all. Both collapsed. Jason Hughey argues the problem isn't whether companies state their valuesâit's whether those values function as actual decision-making frameworks or just motivational posters on the wall. Episode Summary Most organizations betray trust not through malice but through design. Jason Hughey breaks down the two paradigms shaping every workplace: top-down control systems that optimize for short-term extraction, and emergentâŚ
S03E01 Oscar Merry â What Joe Rogan Lost for $100M
âIf you choose to go exclusive on Spotify, you're essentially saying to 70% of your existing and potential audience, âSorry, you can't listen anymore.ââ Oscar Merry watched Joe Rogan lose influence despite a $100 million paydayâand built Fountain to prove there's a better way. Episode Summary Oscar Merry's Alexa skills hit #1 in productivity and earned $30,000 in six months. He moved on when the technology couldn't match the visionâand the gatekeepers made clear it wasn't going to. Now asâŚ
S02E16 Pippellia â Reputation Without a Kill Switch
âWeb of Trust is any network of relationship where trust is distributed and emergentâit's not imposed by someone else.â Pip builds the infrastructure that makes decentralized reputation actually work. While platforms like Twitter sell verification for $8, he's applying Google's PageRank algorithm to Nostrâand giving it away for free. EPISODE SUMMARY Right now, if you want to know whether an account is real or a bot, you're trusting Twitter or Meta to tell you. That model is failingâplatformsâŚ
S02E15 Christian Keroles â What Dissidents Know About Bitcoin
âIt's not enough for me to be taken care of if everyone else on the planet is living in a digital gulag.â CK explains why HRF treats Bitcoin as essential infrastructure for human rightsâand why dictators keep failing to build alternatives that work. Episode Summary One billion people live in democracies with stable currency and property rights. Seven billion don't. Christian Keroles, Director of Financial Freedom at the Human Rights Foundation, argues that Bitcoin flips this equationâgivingâŚ
S02E14 Why Ads Keep Winning
Big Tech captures $670 a year from the average American through attention and data. Voluntary payment has never broken past 5% adoption in 50 years of trying. So why does it still matter? Because it's not about replacing ads. It's about having somewhere to go when the platforms decide you shouldn't exist. Episode Summary Voluntary payment sounds like the answer to surveillance capitalism. Pay creators directly, cut out the middlemen, become the customer instead of the product. The philosophy isâŚ
S02E13 Cory Doctorow â Why Every Platform Betrays You
âThe smallest government you can have is determined by the largest corporation you're willing to tolerate.â Cory Doctorow didn't just coin âenshittificationââhe mapped the precise mechanics of how every platform you depend on will eventually turn against you, and why voting with your wallet won't save you. Episode Summary Cory Doctorow breaks down the three-stage process by which platforms lure users in, lock them down, and extract maximum value until the whole thing collapses. UsingâŚ
S02E12 Average Gary â From classified ops to open source
Operating under a pseudonym fits the ethosâsovereignty starts with controlling your identity. Average Gary brought the âthinking shooterâ principle from Naval Special Warfare into Bitcoin: you don't need to know every answer, but you need to know where to find it. His path from military intelligence through Microsoft to large-scale Bitcoin mining reveals how decentralized systems reward proof of work over credentials and why open source tears down the walls between citizens and the institutionsâŚ
S02E11 Stephen DeLorme â Bitcoin and Freedom by Design
âIt's really difficult to engineer freedom techâsolutions that require you to kind of take ownership of your money, take ownership of your data. These things typically have engineering solutions that are harder to build; they might take a longer time to build, or it might actually require the user to kind of learn something new.â Two days after Square unleashed Bitcoin payments on four million merchants, we're asking the uncomfortable question: what if buttery-smooth UX beats self-custody everyâŚ