Roundtable_026 - The Internet's Black October

We are back for another Roundtable, and this time we've got Giacomo Zucco joining me, Steve, and Jeff to break down the absolute madness of the last month. October was basically a bloodbath for internet security. From the massive Binance hack to the exploits hitting BTCPayServer and Liquid, and software wallets, everything was broken. We also dig into how AI has fundamentally changed the economics of cyber attacks, why fiat credit systems are inseparable from Orwellian surveillance, the inevitability (but containability) of paper Bitcoin, and whether Ethereum, DeFi and Liquid actually learn anything from their near-death experiences. We also get into tail emissions and quantum FUD, overengineered tech, libertarians getting memed into authoritarianism, and why Bitcoin’s messy culture of constant “cancellation” may actually be a powerful defense mechanism. Chapters (00:00:00) - Giacomo Zucco joins the Roundtable (00:09:38) - Paper Bitcoin risks in a free market economy (00:14:10) - Black October hacks and exploits (00:34:54) - How AI changes hacking economics (00:42:30) - AI development plateaus and hardware specialization trends (01:05:27) - AI models, performance metrics, and the Cobra Problem (01:18:50) - Libertarian culture and the authoritarian trap (01:39:28) - High trust networks and Bitcoin cancel culture (01:51:57) - Learning through pain, and the Liquid hack (02:02:47) - Taproot privacy limitations and multi-sig scripts (02:08:08) - Closing thoughts Guest Links Giacomo Zucco on X (Link: https://x.com/giacomozucco) Giacomo Zucco's website (Link: https://www.giacomozucco.com/) Steve Simple Nostr (Link: https://tinyurl.com/3s6a8yn8) Steve Simple on X (Link: https://x.com/stevesimple) Jeff Swann Nostr (Link: https://tinyurl.com/3sjc3bcp) Jeff Swann on X (Link: https://x.com/agoristview) Affiliate Links Become sovereign, hold your keys, be censorship resistant with the Bitbox hardware wallet. Get 5% off everything in the store with code GUY (Link: https://bitbox.swiss/) Get 10% off the best Bitcoin board game in the world, HODLUP! Or any of the other great games from The Free Market Kids! Use code GUY10 at checkout for 10% off your cart! (Link: https://www.freemarketkids.com/collections/games-1) Host Links ⁠⁠Guy on Nostr ⁠(Link: http://tinyurl.com/2xc96ney) ⁠Guy on X ⁠(Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Takes on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) ⁠Bitcoin Audible on X⁠ (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

I bet you’ve noticed it too. Everything we buy just seems cheaper, flimsier, and worse than it used to be. Some call it the "enshittification" of everything. And almost everyone blames the exact same thing: corporate greed and the failures of capitalism. In this episode, I’m sharing my take on the real reason our world feels like it's falling apart. I use a simple story about two winemakers to show how this broken fiat system actually punishes honest businesses and heavily rewards the ones cutting corners. We aren't in a race to the bottom because companies are inherently evil, but because our money forces them to cut corners just to survive. Yet this is actually a solvable problem. We just have to fix the money first. Chapters (00:00:00) - The enshittification of everything (00:01:13) - “Greed” is not an answer (00:02:29) - Monetary inflation (00:02:55) - The winemaker story (00:04:24) - Honest producer squeezed (00:07:58) - Savings and investment (00:13:00) - Sound money incentives (00:15:20) - Monetary inflation rewards crap (00:17:19) - Beyond wine (00:20:58) - Capitalism vs central banks Affiliate Links Become sovereign, hold your keys, be censorship resistant with the Bitbox hardware wallet. Get 5% off everything in the store with code GUY (Link: https://bitbox.swiss/guy/) Get 10% off the best Bitcoin board game in the world, HODLUP! Or any of the other great games from The Free Market Kids! Use code GUY10 at checkout for 10% off your cart! (Link: https://www.freemarketkids.com/collections/games-1) Host Links ⁠Guy on Nostr ⁠(Link: http://tinyurl.com/2xc96ney) ⁠Guy on X ⁠(Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Takes on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) ⁠Bitcoin Audible on X⁠ (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

"There's a lot of emphasis on the moment at how AI is making everything less secure, and that is a part of the story. Of course, any tool, any powerful tool has its advantages and disadvantages or has the thing bad guys can use it, good guys can use it. But the power that I think this actually gives the individual for doing stuff like recovery, I think that in the long run, there's going to be way more people who use this to recover their funds than people who use it and manage to steal someone else's funds. Because of the information you can give it, I got it to interview me: how did I store the seed words? Did I do it in columns or did I do it in rows? Did I mix it? All that stuff I can choose selectively to give to the AI, whereas an attacker, they're basically going in with a kind of like a blank slate and trying to do an attack from relatively low amounts of knowledge in terms of your setup." ~ STACKTOTHEFUTURE In this Chat, I sit down with my producer and good friend STACKTOTHEFUTURE to unpack how he almost lost half his Bitcoin stack to hardware wallet failures. First from the Coldcard entropy bug scare, then from a degraded Ledger screen and an “invalid checksum” seed. We walk through his AI-assisted recovery process, why tools like BTCRecover and careful prompting can let you fix mistakes without trusting anyone with your keys, and how this led him to build Keybackup, an open-source printable paper backup for Bitcoin wallets. Along the way we dive into AI as a net security positive, self-custody tradeoffs, wallet UX for normies, and the Opsec tradeoffs of being public about Bitcoin. Guest Links STACKTOTHEFUTURE on X (Link: https://twitter.com/stack2thefuture) KeyBackup's Website (Link: https://keybackup.org/) Chapters (00:00:00) - Introduction (00:03:42) - Pearcast and AI workflow (00:06:47) - STACKTOTHEFUTURE joins the show (00:12:12) - Coldcard vulnerability and Ledger screen fail (00:20:47) - More supply chain attacks and fake wallet apps (00:36:00) - Invalid checksum & AI-assisted recovery (00:58:30) - Red-teaming code and the singularity stack (01:30:35) - Upgrading paper seed backups with keybackup (01:42:58) - Opsec, physical security, and PO boxes Affiliate Links Become sovereign, hold your keys, be censorship resistant with the BitBox hardware wallet. Get 5% off everything in the store with code GUY. (Link: https://bitbox.swiss/guy/) Get 10% off the best Bitcoin board game in the world, HODLUP, or any of the other great games from The Free Market Kids. Use code GUY10 at checkout for 10% off your cart. (Link: https://www.freemarketkids.com/collections/games-1) Host Links Guy on Nostr (Link: http://tinyurl.com/2xc96ney) Guy on X (Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Take on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) Bitcoin Audible on X (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

"This isn't one bad week. It's the start of something we all need to be prepared for. Just look at the numbers. Security firm CrowdStrike says the attacks it sees that likely involve AI agents more than doubled in August, then doubled again in September. And if this week is any indication, it's only speeding up." ~ Matt Shumer In this Read, I walk through why this new wave of AI-driven hacks isn’t just another bad week for cybersecurity but the beginning of a structural shift in how we protect ourselves on the internet. Using Matt Shumer’s latest piece “The Internet is Under Attack” as a launchpad, I dig into AI exploit tooling, social-engineering scams powered by human-like voice models, and why trust in remote systems is rapidly crumbling. I close with concrete steps you can take right now to harden your digital life and why Bitcoin, private spaces, and verifiable proofs are going to matter more than ever. Check out the original article: The Internet Is Under Attack by Matt Shumer (Link: https://somethingbig.ai/something-big-is-happening-in-cyber) Chapters (00:00:00) - Introduction (00:01:46) - The Internet Is Under Attack (00:06:01) - Why this is different (00:07:55) - This is going to keep happening (00:09:02) - What this means for you (00:10:03) - What to do today (00:13:09) - Guy’s security habits (00:24:00) - Private spaces vs public web (00:32:58) - AI, work and small business (00:42:50) - Future of security and proof Affiliate Links Become sovereign, hold your keys, be censorship resistant with the BitBox hardware wallet. Get 5% off everything in the store with code GUY. (Link: https://bitbox.swiss/guy/) Get 10% off the best Bitcoin board game in the world, HODLUP, or any of the other great games from The Free Market Kids. Use code GUY10 at checkout for 10% off your cart. (Link: https://www.freemarketkids.com/collections/games-1) Host Links Guy on Nostr (Link: http://tinyurl.com/2xc96ney) Guy on X (Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Take on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) Bitcoin Audible on X (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

I break down four of the biggest lies we’re told about inflation, from the idea that prices must always rise to the fantasy that GDP growth means we’re getting richer. I show how money printing, cheap debt, and fake economic metrics quietly transfer real wealth from workers and savers to the already powerful. If you’ve ever wondered why everything feels more expensive and more fragile, this is a quick demolition of the stories we’ve been sold. Chapters (00:00:00) - Introduction (00:00:21) - Everything should always get more affordable (00:01:16) - Corporate greed cannot cause real inflation (00:02:42) - Inflation only hurts the economy (00:04:16) - GDP is not a useful metric (00:05:37) - Closing thoughts Affiliate Links Become sovereign, hold your keys, be censorship resistant with the BitBox hardware wallet. Get 5% off everything in the store with code GUY. (Link: https://bitbox.swiss/guy/) Get 10% off the best Bitcoin board game in the world, HODLUP, or any of the other great games from The Free Market Kids. Use code GUY10 at checkout for 10% off your cart. (Link: https://www.freemarketkids.com/collections/games-1) Host Links Guy on Nostr (Link: http://tinyurl.com/2xc96ney) Guy on X (Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Take on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) Bitcoin Audible on X (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

"The cost of intelligence keeps falling toward the cost of electricity, and everyone will share in what that intelligence can do. Bitcoin captures the gains directly, while in dollar terms they are inflated away." ~ Early RIders In this episode I read and unpack “The Singularity Stack” by Early Riders, a framework that follows energy as it becomes compute, intelligence, agent work, and finally settles in money. I connect that thesis to Bitcoin, arguing that only a fixed-supply asset can actually capture the deflationary gains of AI-driven productivity instead of inflating them away. Along the way, I walk through my own AI and peer-to-peer-powered production stack as a concrete example of how fast this feedback loop is already moving. Check out the original report: The Singularity Stack by Early Riders (Link: https://earlyriders.com/singularity-stack/) Affiliate Links Become sovereign, hold your keys, be censorship resistant with the Bitbox hardware wallet. Get 5% off everything in the store with code GUY (Link: https://bitbox.swiss/) Get 10% off the best Bitcoin board game in the world, HODLUP! Or any of the other great games from The Free Market Kids! Use code GUY10 at checkout for 10% off your cart! (Link: https://www.freemarketkids.com/collections/games-1) Host Links ⁠⁠Guy on Nostr ⁠(Link: http://tinyurl.com/2xc96ney) ⁠Guy on X ⁠(Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Takes on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) ⁠Bitcoin Audible on X⁠ (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

In this breakdown of the Ledger supply chain hack, I walk through how a tiny hardware implant turned legitimate hardware wallets into seed-stealing spy devices. I cover who’s actually at risk, why buying from resellers is a ticking time bomb, and what self-custody conditions are now non‑negotiable for serious bitcoiners. This isn’t the end of self-custody but a painful step we have to take to make it robust enough for the world we’re heading into. Chapters (00:00:00) - The Great Hackening continues (00:02:05) - Resellers and attack surfaces (00:02:38) - Timeline and who's at risk (00:03:53) - Inside the Ledger implant (00:06:06) - Genuine check still passed (00:07:00) - Who is actually at risk (00:09:51) - Is self-custody dead? (00:13:37) - What does this change (00:15:45) - Conclusion Affiliate Links Become sovereign, hold your keys, be censorship resistant with the Bitbox hardware wallet. Get 5% off everything in the store with code GUY (Link: https://bitbox.swiss/guy/) Get 10% off the best Bitcoin board game in the world, HODLUP! Or any of the other great games from The Free Market Kids! Use code GUY10 at checkout for 10% off your cart! (Link: https://www.freemarketkids.com/collections/games-1) Host Links ⁠Guy on Nostr ⁠(Link: http://tinyurl.com/2xc96ney) ⁠Guy on X ⁠(Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Takes on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) ⁠Bitcoin Audible on X⁠ (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

I break down the biggest lie we've all deeply internalized about the economy: that prices are just supposed to go up. In a productive and advancing society, almost everything should actually be getting more affordable over time. Using a very simple analogy, I show exactly how the creation of new money quietly robs us of the prosperity our hard work should be delivering. Chapters (00:00:00) - Everything should get cheaper (00:01:06) - The apple economy (00:01:58) - Counterfeit money (00:02:20) - Lost productivity gains (00:02:43) - Printing as silent theft (00:03:31) - Who is to blame?\ Affiliate Links Become sovereign, hold your keys, be censorship resistant with the BitBox hardware wallet. Get 5% off everything in the store with code GUY. (Link: https://bitbox.swiss/guy/) Get 10% off the best Bitcoin board game in the world, HODLUP, or any of the other great games from The Free Market Kids. Use code GUY10 at checkout for 10% off your cart. (Link: https://www.freemarketkids.com/collections/games-1) Host Links Guy on Nostr (Link: http://tinyurl.com/2xc96ney) Guy on X (Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Take on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) Bitcoin Audible on X (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

We finally stopped being lazy and brought a guest onto the Roundtable. Max Hillebrand joins Steve, Jeff, and I to talk about the absolute madness happening in the freedom tech space right now. Max has been using AI agents to solve challenging computer science problems for White Noise and the Marmot protocol. We talk about the possibility that we are moving toward a future where the average user base for a custom piece of software is exactly one person. I share how I sent my AI agents after a spam caller company to track down the CEO's personal cell phone, and Steve explains how he's automating his bar's point-of-sale system with some interesting techniques. But we don't just stick to software. We also discuss the need for open-source modular and repairable hardware. And of course, we cover the latest in the Bitcoin space. We review the latest exploits, how exchanges are handling flagged coins, and Steve pitches an incredibly clever way to measure Bitcoin's true purchasing power without ever looking at the fiat price. It was a wild conversation with the guys about where this whole decentralized, peer-to-peer future is actually heading. Chapters (00:00:00) - Episode intro (00:09:42) - AI cycle and Freedom tech update (00:38:29) - Sovereign Engineering cohorts (00:41:27) - AI, decentralization, and the global brain (00:48:33) - Responsibility, hierarchy, and decentralized companies (00:57:59) - Open source cars, power tools, and hardware (01:25:41) - Current Bitcoin drama (01:47:19) - Measuring Bitcoin purchasing power with UTXO size (01:56:29) - Marmot protocol and MLS group encryption explained Guest Links Steve Simple Nostr (Link: https://tinyurl.com/3s6a8yn8) Steve Simple on X (Link: https://x.com/stevesimple) Jeff Swann Nostr (Link: https://tinyurl.com/3sjc3bcp) Jeff Swann on X (Link: https://x.com/agoristview) Max Hillebrand Nostr (Link: https://tinyurl.com/y4bsmpkk) Max Hillebrand's website (Link: https://towardsliberty.com/) Affiliate Links Become sovereign, hold your keys, be censorship resistant with the Bitbox hardware wallet. Get 5% off everything in the store with code GUY (Link: https://bitbox.swiss/) Get 10% off the best Bitcoin board game in the world, HODLUP! Or any of the other great games from The Free Market Kids! Use code GUY10 at checkout for 10% off your cart! (Link: https://www.freemarketkids.com/collections/games-1) Host Links ⁠⁠Guy on Nostr ⁠(Link: http://tinyurl.com/2xc96ney) ⁠Guy on X ⁠(Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Takes on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) ⁠Bitcoin Audible on X⁠ (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839)

In this Take, I break down why the biggest AI labs, while deeply unprofitable sitting on massive future compute obligations, are racing toward trillion-dollar valuations. I explore how open-source competition, especially from China, is crushing their moat, and why that pushes them toward lobbying for fear-driven regulation, immunity, and government partnerships. Ultimately, I argue that the AI panic is about preserving a failing business model and building a centralized surveillance infrastructure, and why we shouldn’t be the ones paying their bill. Chapters (00:00:00) - Introduction (00:00:27) - OpenAI’s insane obligations (00:01:51) - Anthropic’s profit illusion (00:02:40) - Trillion-dollar IPO dreams (00:03:12) - The open-source threat (00:04:38) - Engineering the panic (00:06:10) - Regulatory moat and control (00:09:11) - What this is all about Affiliate Links Become sovereign, hold your keys, be censorship resistant with the Bitbox hardware wallet. Get 5% off everything in the store with code GUY (Link: https://bitbox.swiss/guy/) Get 10% off the best Bitcoin board game in the world, HODLUP! Or any of the other great games from The Free Market Kids! Use code GUY10 at checkout for 10% off your cart! (Link: https://www.freemarketkids.com/collections/games-1) Host Links ⁠Guy on Nostr ⁠(Link: http://tinyurl.com/2xc96ney) ⁠Guy on X ⁠(Link: https://twitter.com/theguyswann) Guy on Instagram (Link: https://www.instagram.com/theguyswann) Guy on TikTok (Link: https://www.tiktok.com/@theguyswann) Guy's Takes on YouTube (Link: https://www.youtube.com/@GuysTake) Guy Swann on YouTube (Link: https://www.youtube.com/@theguyswann) ⁠Bitcoin Audible on X⁠ (Link: https://twitter.com/BitcoinAudible) The Guy Swann Network Broadcast Room on Keet (Link: https://tinyurl.com/3na6v839) References from the episode The Hater's Guide To AI Debt (Part 1): https://tinyurl.com/3tvvsbee The Hater's Guide To AI Debt (Part 2): https://tinyurl.com/5n95nwpy