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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Please leave a review - one index finger spasm for you, a day made for me. The emergent characteristics of crony capitalism have punished those inclined to go against the grain. My guests and I tackle existential questions, financial topics, current events - while celebrating those with the courage to be different.
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Episode #36: Tiny Computers, Massive Shifts: The iPhone’s Quiet Coup
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1:00:42Welcome 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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1:03:18In 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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1:01:56On 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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50:35Welcome 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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54:41On 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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50:15In 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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1:01:49Welcome 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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58:50On 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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1:02:24Welcome 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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55:06In 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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56:43In 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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52:31Welcome 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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53:33On 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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55:10In 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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Episode #31: Satya’s Quiet Coup: How Microsoft Got Its Groove Back
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51:12Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they unpack the rise of Satya Nadella and how his leadership reshaped Microsoft’s culture, capital strategy, and role in the AI boom. The conversation traces the company’s shift from a Windows-obsessed, top-down org to a more open, developer-friendly platform player—ho…
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Episode #448: From Prompt Injection to Reverse Shells: Navigating AI's Dark Alleyways with Naman Mishra
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47:55In this episode of Crazy Wisdom, I, Stewart Alsop, sit down with Naman Mishra, CTO of Repello AI, to unpack the real-world security risks behind deploying large language models. We talk about layered vulnerabilities—from the model, infrastructure, and application layers—to attack vectors like prompt injection, indirect prompt injection through agen…
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Episode #447: From Frustration to Creation: Building with Chaos Instead of Blueprints
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59:21In this episode of the Crazy Wisdom Podcast, I, Stewart Alsop, speak with Perry Knoppert, founder of The Octopus Movement, joining us from the Netherlands. We explore everything from octopus facts (like how they once had bones and decided to ditch them—wild, right?) to neurodivergence, non-linear thinking, the alien-like nature of both octopuses an…
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Episode #30: From InfoWorld to x.com: The Patterns That Repeat
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53:15Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation winds through a rich mix of personal history, editorial philosophy, and the evolution of tech—from getting fired (twice) to putting Steve Jobs on the cover of Inc. in 1981, from the impact of VisiCalc on Apple II adoption to the deeper meaning of what …
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Episode #446: Decentralized Truth and the Digital Republic
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51:11On this episode of the Crazy Wisdom Podcast, I, Stewart Alsop, sit down with Federico Ast, founder of Kleros, to explore how decentralized justice systems can resolve both crypto-native and real-world disputes. We talk about the pilot with the Supreme Court in Mendoza, Argentina, where Kleros is helping small claims courts resolve cases faster and …
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Episode #445: How Decentralized Tech Could Challenge Nation-States
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51:17In this episode of Crazy Wisdom, host Stewart Alsop talks with Rosario Parlanti, a longtime crypto investor and real estate attorney, about the shifting landscape of decentralization, AI, and finance. They explore the power struggles between centralized and decentralized systems, the role of AI agents in finance and infrastructure, and the legal gr…
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Episode #29: Bridging the Physical and Digital: Investing in the Next Big Shift
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1:00:37Welcome to Stewart Squared podcast with the two Stewart Alsops, featuring special guest Jim Ward. In this episode, Jim shares insights on the "third convergence" and the "reality disturbance," exploring how emerging technologies like AI, XR, and immersive media are reshaping our world. He and Stewart Alsop II discuss the evolution of personal compu…
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Episode #444: The Hidden Frameworks of the Internet: Knowledge Graphs, Ontologies, and Who Controls Truth
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1:00:23On this episode of the Crazy Wisdom Podcast, host Stewart Alsop welcomes Jessica Talisman, a senior information architect deeply immersed in the worlds of taxonomy, ontology, and knowledge management. The conversation spans the evolution of libraries, the shifting nature of public and private access to knowledge, and the role of institutions like t…
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