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In his series "Crazy Wisdom," Stewart Alsop explores cutting-edge topics, particularly in the realm of technology, such as Urbit and artificial intelligence. Alsop embarks on a quest for meaning, engaging with others to expand his own understanding of reality and that of his audience. The topics covered in "Crazy Wisdom" are diverse, ranging from emerging technologies to spirituality, philosophy, and general life experiences. Alsop's unique approach aims to make connections between seemingly ...
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Stewart Alsop III reviews a broad range of topics with his father Stewart Alsop II, who started his career in the personal computer industry and is still actively involved in investing in startup technology companies. Stewart Alsop III is fascinated by what his father was doing as SAIII was growing up in the Golden Age of Silicon Valley. Topics include: - How the personal computing revolution led to the internet, which led to the mobile revolution - Now we are covering the future of the inte ...
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Episode #465: Proof of Aliveness: A Cryptographic Theater of the Real
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I, Stewart Alsop, am thrilled to welcome Xathil of Poliebotics to this episode of Crazy Wisdom, for what is actually our second take, this time with a visual surprise involving a fascinating 3D-printed Bauta mask. Xathil is doing some truly groundbreaking work at the intersection of physical reality, cryptography, and AI, which we dive deep into, e…
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Episode #38: Trust Issues: From Meme Coins to Mainframes
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Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we talk about what happened to trust—why it’s gone, where it went, and whether it can be rebuilt. We go from the 1990s paranoia about driver’s licenses to today’s AI-powered pendants that record everything, from the erosion of open internet ideals to the rise of app st…
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Episode #464: From Meme Coins to Mind Melds: Crypto Meets AI
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I, Stewart Alsop, had a fascinating conversation on this episode of Crazy Wisdom with Mallory McGee, the founder of Chroma, who is doing some really interesting work at the intersection of AI and crypto. We dove deep into how these two powerful technologies might reshape the internet and our interactions with it, moving beyond the hype cycles to wh…
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Episode #463: Brave New Playgrounds: Real-World Games in a Post-Trust Era
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I, Stewart Alsop, welcomed Ben Roper, CEO and founder of Play Culture, to this episode of Crazy Wisdom for a fascinating discussion. We kicked things off by diving into Ben's reservations about AI, particularly its impact on creative authenticity, before exploring his innovative project, Play Culture, which aims to bring tactical outdoor games to a…
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Episode #37: From IBM to AI: How Business Lost Its Mind and Found the Algorithm
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Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they track the transformation of business from the IBM-dominated 1980s to today's AI-driven landscape, exploring how personal computing, the rise of the internet, and eventually search and social media changed the way companies operate. The conversation moves from earl…
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Episode #462: The Apostolic Internet: Lines of Authority in a Fractured Age
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I, Stewart Alsop, am thrilled to welcome Leon Coe back to the Crazy Wisdom Podcast for a second deep dive. This time, we journeyed from the Renaissance and McLuhan's media theories straight into the heart of theology, church history, and the very essence of faith, exploring how ancient wisdom and modern challenges intertwine. It was a fascinating e…
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Episode #461: Morpheus in the Classroom: AI, Education, and the New Literacy
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I, Stewart Alsop, welcomed Woody Wiegmann to this episode of Crazy Wisdom, where we explored the fascinating and sometimes unsettling landscape of Artificial Intelligence. Woody, who is deeply involved in teaching AI, shared his insights on everything from the US-China AI race to the radical transformations AI is bringing to education and society a…
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Episode #36: Elegance vs. Exquisite: Rethinking Systems Old and New
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I, Stewart Alsop, was absolutely thrilled to have my dad, Stewart Alsop II, and our very special guest, Gilman Louie, on this episode of Crazy Wisdom. We journeyed through Gilman's incredible career, from pioneering video games in the 80s with severe hardware limitations and the whirlwind of the Pokemon card craze, to his instrumental work founding…
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Episode #460: Voice First, Future Forward: The AI Agents Are Here
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I, Stewart Alsop, welcomed Alex Levin, CEO and co-founder of Regal, to this episode of the Crazy Wisdom Podcast to discuss the fascinating world of AI phone agents. Alex shared some incredible insights into how AI is already transforming customer interactions and what the future holds for company agents, machine-to-machine communication, and even t…
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Episode #36: Tiny Computers, Massive Shifts: The iPhone’s Quiet Coup
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Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation ranges across the years that saw Apple shift from a struggling personal computer company to the launch of the iPhone, marking a deeper convergence of mobile technology and cloud infrastructure. The Stewarts explore how the so-called "Web 2.0" years—dec…
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Episode #458: How a Tiny Irish Startup Beat Amazon to the Air
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In this episode of the Crazy Wisdom Podcast, Stewart Alsop III talks with Bobby Healy, CEO and co-founder of Manna Drone Delivery, about the evolving frontier where the digital meets the physical—specifically, the promise and challenges of autonomous drone logistics. They explore how regulatory landscapes are shaping the pace of drone delivery adop…
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Episode #457: Surviving the Dark Forest: Cryptography, Tribes, and the End of Institutions
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On this episode of Crazy Wisdom, I, Stewart Alsop, spoke with Neil Davies, creator of the Extelligencer project, about survival strategies in what he calls the “Dark Forest” of modern civilization — a world shaped by cryptographic trust, intelligence-immune system fusion, and the crumbling authority of legacy institutions. We explored how concepts …
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Episode #35: From the Great Society to the Great Fragmentation
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Welcome to Stewart Squared podcast with the two Stewart Alsops. Today’s episode moves beyond technology to explore a deeply personal and historical reflection on the Great Society under Lyndon B. Johnson, sparked by a late-night email about the political and cultural shifts of the 1960s. The conversation weaves together vivid childhood memories of …
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Episode #456: What Happens When Your AI Thinks Like You (On Purpose)
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On this episode, Stewart Alsop talks with Suman Kanuganti, founder of Personal.ai and a pioneer in AI for accessibility and human-machine collaboration. Together, they explore how Suman’s journey from launching Aira to building Personal.ai reflects a deeper mission of creating technology that enhances memory, communication, and personal empowerment…
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Episode #455: The End of IPOs and the Rise of Tokenized Everything
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In this episode of the Crazy Wisdom Podcast, I, Stewart Alsop III, speak with David Packham, CEO and co-founder of Chintai, about the real-world implications of tokenizing assets—from real estate and startup equity to institutional finance and beyond. David shares insights from his time inside Goldman Sachs during the 2008 crash, his journey into b…
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Episode #34: From Magellan to the Machine: Bill Gross on the Search for Meaning
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Welcome to Stewart Squared podcast with the two Stewart Alsops. In this wide-ranging conversation, they’re joined by legendary entrepreneur and Idealab founder Bill Gross to trace the arcs of personal computing, the early Internet, and today's AI boom. The episode explores Bill’s early work with products like Lotus Magellan and GoTo.com, reflects o…
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Episode #453: Trustware vs. Adware: Toward a Humane Stack for Human Life
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On this episode of the Crazy Wisdom podcast, I, Stewart Alsop, sat down once again with Aaron Lowry for our third conversation, and it might be the most expansive yet. We touched on the cultural undercurrents of transhumanism, the fragile trust structures behind AI and digital infrastructure, and the potential of 3D printing with metals and geopoly…
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Episode #33: From Mainframes to Minds: Rethinking the Architecture of Intelligence
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Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation starts with a personal quest into vector databases and linked data, but opens into a sweeping narrative of how the Internet—built on protocols like TCP/IP and scaffolding like URIs—evolved from Cold War military infrastructure into the backbone of our …
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Episode #452: Text as Interface: Rethinking Human-Computer Symbiosis
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In this episode of Crazy Wisdom, Stewart Alsop talks with Will Bickford about the future of human intelligence, the exocortex, and the role of software as an extension of our minds. Will shares his thinking on brain-computer interfaces, PHEXT (a plain text protocol for structured data), and how high-dimensional formats could help us reframe the way…
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Episode #451: Narrative as Infrastructure: Why Culture Now Runs on Memes
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In this episode of Crazy Wisdom, I, Stewart Alsop, sit down with Trent Gillham—also known as Drunk Plato—for a far-reaching conversation on the shifting tides of technology, memetics, and media. Trent shares insights from building Meme Deck (find it at memedeck.xyz or follow @memedeckapp on X), exploring how social capital, narrative creation, and …
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Episode #32: Startups, Deadlines, and Drift: The Venture Logic Behind Modern Newsrooms
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Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation weaves through the evolution of media, venture capital’s long shadow over technology, and how editorial instincts have (or haven’t) adapted to the pace of software. Stewart Alsop II brings firsthand insight into the early days of digital publishing and…
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Episode #450: 102% Backed and 100% Transparent: Inside the Wyoming Stable Token
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On this episode of Crazy Wisdom, I’m joined by David Pope, Commissioner on the Wyoming Stable Token Commission, and Executive Director Anthony Apollo, for a wide-ranging conversation that explores the bold, nuanced effort behind Wyoming’s first-of-its-kind state-issued stable token. I’m your host Stewart Alsop, and what unfolds in this dialogue is …
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Episode #449: The Strange Loop: How Biology and Computation Shape Each Other
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55:10
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In this episode of Crazy Wisdom, Stewart Alsop speaks with German Jurado about the strange loop between computation and biology, the emergence of reasoning in AI models, and what it means to "stand on the shoulders" of evolutionary systems. They talk about CRISPR not just as a gene-editing tool, but as a memory architecture encoded in bacterial imm…
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