Podcast by @jposhaughnessy & @osvllc | Upgrade your HumanOS 🧠 | Download our free list of 100 timeless, underappreciated books (link in bio).

"The only way we actually solve problems is by experiencing them and mitigating them." Julie Fredrickson (@AlmostMedia) is the Managing Partner of Chaotic Capital and advocated for Montana's Right to Compute Act, the first state law of its kind. The conversation covers what the encryption wars and nuclear power teach about regulating AI, why human data may become the most valuable asset online, and how to think clearly when AI can persuade at scale. Out now on Infinite Loops, with host @jposhaughnessy. TIMESTAMPS 0:00 Intro 1:08 AI Moves Into the Real World 2:32 Is Compute Free Speech? 4:05 Lessons From the Encryption Wars 6:30 Pro-AI Is Not Anti-Safety 8:50 The Case for Rational Optimism 13:21 If Julie Ran AI Policy 15:50 Jim's Case for Sensible Regulation 17:47 Is AI Still in Its Invention Phase? 20:28 How AI Crawlers Change the Web 23:19 Amazon Blocks Meta's Muse 24:20 Why Chatbots Recommend CeraVe 27:53 Being Human as a Job 33:23 Zero-Knowledge Proofs 34:44 Lost Patents and Ancient Scrolls 38:28 Who Owns AI's Data? 40:45 The Statistic Nobody Could Source 42:52 Tracing Where Information Comes From 44:55 Astroturfing Since Jericho 47:45 1984 and Cognitive Security 52:09 Asking AI Where He Was Wrong 54:46 Why Jim Quit TV News 59:32 Being Early on Nuclear 1:02:22 A Reactor Built in a Year 1:04:17 Nuclear Fear and the Precautionary Principle 1:09:07 Aligned to What? Open Source AI 1:11:33 2,089 Days of Writing 1:17:17 What an LLM Found in Her Writing 1:19:39 Using AI as an Honest Critic 1:22:52 What Investors Are Missing 1:26:34 Two Ideas for the World
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The next big job of the AI era might be being a real person online. @jposhaughnessy and @AlmostMedia on why human-made content may become the most valuable thing on the internet. Julie's take: - Human-mediated work will grow - Literacy and people skills probably matter more - Storytellers have a good chance of doing well Vernor Vinge imagined this job in his 2006 novel Rainbows End. On Infinite Loops.
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Why so much of history is still offline? Chaotic Capital Managing Partner Julie Fredrickson (@AlmostMedia) on the archives that never made it online, from cultural records to patents no one technically owns, and why the Herculaneum scrolls show what's possible. On Infinite Loops with @jposhaughnessy
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"The web itself wasn't built for agents and the level of speed that they operate on." @AlmostMedia on how AI crawlers and agents are changing the economics of the open web. Cloudflare data: GPTBot requests up 305% in a year. ChatGPT-User requests up 2,825%. With @jposhaughnessy on Infinite Loops.
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"The only way we actually solve problems is by experiencing them and mitigating them." Julie Fredrickson (@AlmostMedia) is the Managing Partner of Chaotic Capital and advocated for Montana's Right to Compute Act, the first state law of its kind. The conversation covers what the encryption wars and nuclear power teach about regulating AI, why human data may become the most valuable asset online, and how to think clearly when AI can persuade at scale. Out now on Infinite Loops, with host @jposhaughnessy. TIMESTAMPS 0:00 Intro 1:08 AI Moves Into the Real World 2:32 Is Compute Free Speech? 4:05 Lessons From the Encryption Wars 6:30 Pro-AI Is Not Anti-Safety 8:50 The Case for Rational Optimism 13:21 If Julie Ran AI Policy 15:50 Jim's Case for Sensible Regulation 17:47 Is AI Still in Its Invention Phase? 20:28 How AI Crawlers Change the Web 23:19 Amazon Blocks Meta's Muse 24:20 Why Chatbots Recommend CeraVe 27:53 Being Human as a Job 33:23 Zero-Knowledge Proofs 34:44 Lost Patents and Ancient Scrolls 38:28 Who Owns AI's Data? 40:45 The Statistic Nobody Could Source 42:52 Tracing Where Information Comes From 44:55 Astroturfing Since Jericho 47:45 1984 and Cognitive Security 52:09 Asking AI Where He Was Wrong 54:46 Why Jim Quit TV News 59:32 Being Early on Nuclear 1:02:22 A Reactor Built in a Year 1:04:17 Nuclear Fear and the Precautionary Principle 1:09:07 Aligned to What? Open Source AI 1:11:33 2,089 Days of Writing 1:17:17 What an LLM Found in Her Writing 1:19:39 Using AI as an Honest Critic 1:22:52 What Investors Are Missing 1:26:34 Two Ideas for the World
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"Someday I'll be able to spin the globe, and every little part of the world will feel like home." Author and entrepreneur Derek Sivers (@sivers) on the Steve Pavlina idea that changed his life. On Infinite Loops with @jposhaughnessy.
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Why does uncertainty keep a mind open? Entrepreneur, author, and speaker @sivers on why he reserves the word "true" for what has no other possible answer, and why his book Useful Not True treats everything else as open to question. On Infinite Loops with @jposhaughnessy.
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Why must parents step back from making every decision for their teenagers? Entrepreneur, author, and speaker @sivers on the moment he realized his 14-year-old son was no longer a kid, and how the parent's role shifts to consultant. On Infinite Loops with @jposhaughnessy.
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What does tech independence look like in practice? Entrepreneur, author, and speaker Derek Sivers on running personal email, files, calendars, and contacts from one small server instead of Big Tech's cloud. On Infinite Loops with @jposhaughnessy. Tech Independence: sive.rs/ti
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Why does unexpected pain hit the hardest? Entrepreneur, author, and speaker Derek Sivers (@sivers) on the core idea of the Pursue Pain chapter in his book How to Live, and why choosing the hard path takes away pain's power. On Infinite Loops with @jposhaughnessy.
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How can one idea in a book change the rest of a life? Entrepreneur, author, and speaker @sivers on the idea that led him to leave the US at almost 40: live somewhere different enough to surprise him daily, and stay until it feels like home. On Infinite Loops with @jposhaughnessy.
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The me that was sleeping in that car and eating cold Burger King whoppers for every meal of my life couldn’t have imagined I would be a Surgeon driving a G Wagon on the daily. I learned a long time ago that No one is coming to save you. You just have to survive.
“A powerful and deeply moving account of a boy forced to grow up too soon and the man he fought to become.” — @robkhenderson You’ve never read a biography like this. Preorders are now live! infinitebooks.com/products/n…
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"Pain's power relies on surprise. If you expect it, it's weaker. If you choose it, it's gone." Derek Sivers (@sivers is an author, entrepreneur, and TED speaker. He founded CD Baby, once the largest seller of independent music online, with more than $100 million in sales for over 150,000 musicians. After more than a year of saying no to every podcast, he said yes to this one. The conversation covers raising a son, why he moves countries on purpose, the certainty slider, leading a team as an explorer, and how AI can make you more independent from big tech. Out now on Infinite Loops, with host @jposhaughnessy. TIMESTAMPS 0:00 Intro 1:30 30 Hours a Week With His Son 4:41 From Manager to Consultant 9:57 Letting Kids Feel the Consequences 15:16 Why He Moves Countries on Purpose 22:31 Who We Become for Other People 28:47 Why Bangalore 32:35 Living Many Lives in One Lifetime 36:41 Using AI to Steelman the Other Side 42:24 A $1,000-a-Year Company for a China Visa 46:47 The Certainty Slider 55:49 Why Saying "I Don't Know" Builds Trust 58:18 Speaking Only When There Is Something to Say 1:00:21 Explorers vs. Straight-Line Leaders 1:07:22 Tech Independence and Punk Tech 1:11:12 How AI Can Make You More Independent 1:20:07 Science Is Punk 1:26:28 Cutting a Paragraph Down to One Line 1:31:25 The Vicious AI Critic 1:34:40 Restrictions Will Set You Free 1:38:07 Useful Not True and the Bridge of Nihilism
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This journey has been long and I never realized what I had truly accomplished - or how much I curse - and until it was written in this book. I pray that my story helps others and can be a source of inspiration. With that said, can you please share this?
“A powerful and deeply moving account of a boy forced to grow up too soon and the man he fought to become.” — @robkhenderson You’ve never read a biography like this. Preorders are now live! infinitebooks.com/products/n…
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“A powerful and deeply moving account of a boy forced to grow up too soon and the man he fought to become.” — @robkhenderson You’ve never read a biography like this. Preorders are now live! infinitebooks.com/products/n…
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What is written inside scrolls burned by Mount Vesuvius? Vesuvius Challenge co-founder Dr. Brent Seales on how 2,000 competitors pulled words from the ashes, one letter at a time. Dr. Brent Seales is the Stanley and Karen Pigman Chair of Heritage Science at the University of Kentucky and co-founder of the Vesuvius Challenge. From his conversation with @nicktawil on Infinite Loops.
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What happens when a 2,000-year-old library can finally be read? Vesuvius Challenge co-founder Dr. Brent Seales on why his technical work is substantially complete, and why the focus now shifts to the scholars who read the ancient texts. On Infinite Loops with @nicktawil.
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What is virtual unwrapping? Vesuvius Challenge co-founder Dr. Brent Seales: the X-ray gives a model of everything inside a sealed scroll, still wound and compressed. The software that flattens it into a readable page is what his team invented. On Infinite Loops with @nicktawil.
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