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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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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 #446: Decentralized Truth and the Digital Republic
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On 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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In 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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Welcome 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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On 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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Episode #443: Escaping the Algorithm: Building the Future of Social Media with Interoperability
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On this episode of the Crazy Wisdom Podcast, host Stewart Alsop is joined by Jesse and Leo, co-founders of Maitri, a social infrastructure project focused on fostering interoperability between different social media applications. They explore the limitations of current social networks, the importance of community graphs in building trust and reputa…
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Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore the evolution of technology from the rise of the PC, internet, and mobile phone to the current state of AI, cutting through the hype with firsthand insights from decades of industry experience. They discuss concepts like "reality disturbance," introduced b…
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Episode #442: Satellites, Strategy, and Staying Profitable: A No-BS Look at Space Tech
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On this episode of Crazy Wisdom, I, Stewart Alsop, sit down with Gabe Dominocielo, co-founder of Umbra, a space tech company revolutionizing satellite imagery. We discuss the rapid advancements in space-based observation, the economics driving the industry, and how AI intersects with satellite data. Gabe shares insights on government contracting, d…
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Episode #441: Escaping the Algorithm: The Battle for Human Intention
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On this episode of Crazy Wisdom, Stewart Alsop welcomes Andrew Burlinson, an artist and creative thinker, for a deep conversation about technology, creativity, and the human spirit. They explore the importance of solitude in the creative process, the addictive nature of digital engagement, and how AI might both challenge and enhance human expressio…
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Episode #27: From Napster to OpenAI: The Relentless Disruption of Everything
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Welcome to the Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the concept of "convergences" in technology, focusing on the rise of personal computing, the internet, and smartphones. We revisit Nicholas Negroponte’s insights on digital publishing, the second convergence's shift to networked computing, and the emergi…
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Episode #440: AI Agents, Code Wizards, and What Could Possibly Go Wrong?
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Stewart Alsop sat down with Nick Ludwig, the creator of Kibitz and lead developer at Hyperware, to talk about the evolution of AI-powered coding, the rise of agentic software development, and the security challenges that come with giving AI more autonomy. They explored the power of Claude MCP servers, the potential for AI to manage entire developme…
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Episode #439: Beyond Second Brains: What AI Is Actually Doing to Knowledg
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On this episode of Crazy Wisdom, host Stewart Alsop speaks with Andrew Altschuler, a researcher, educator, and navigator at Tana, Inc., who also founded Tana Stack. Their conversation explores knowledge systems, complexity, and AI, touching on topics like network effects in social media, information warfare, mimetic armor, psychedelics, and the evo…
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Episode #26: Steve Case on the Internet’s Wild Ride and What’s Next
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Welcome to Stewart Squared podcast with the two Stewart Alsops. Today’s guest is Steve Case, former CEO of AOL and the founder of Revolution. In this episode, we cover his journey from early internet days to building AOL, the role of venture capital beyond traditional tech hubs, and how policy shapes innovation. Steve also shares insights on the ev…
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Episode #438: What If AI Is Just the Next Political Revolution?
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On this episode of Crazy Wisdom, host Stewart Alsop speaks with Ivan Vendrov for a deep and thought-provoking conversation covering AI, intelligence, societal shifts, and the future of human-machine interaction. They explore the "bitter lesson" of AI—that scale and compute ultimately win—while discussing whether progress is stalling and what bottle…
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Episode #437: From Garage Sales to Multi-Million Dollar E-Commerce Empires
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In this episode of the Crazy Wisdom Podcast, host Stewart Alsop speaks with Jason Nadaf, CEO and founder of SureDone, about the evolving landscape of e-commerce, automation, and the role of AI in shaping the future of online sales. They explore how multi-channel selling has transformed over the years, the inefficiencies of big tech in commerce, and…
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Episode #436: How AI Will Reshape Power, Governance, and What It Means to Be Human
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On this episode of Crazy Wisdom, I, Stewart Alsop, sit down with AI ethics and alignment researcher Roko Mijic to explore the future of AI, governance, and human survival in an increasingly automated world. We discuss the profound societal shifts AI will bring, the risks of centralized control, and whether decentralized AI can offer a viable altern…
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Episode #435: How AI, Drones, and Rare Earths Will Decide the Next Global Conflict
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On this episode of Crazy Wisdom, host Stewart Alsop talks with Troy Johnson, founder and partner at Resource Development Group, LLC, about the deep history and modern implications of mining. From the earliest days of salt extraction to the role of rare earth metals in global geopolitics, the conversation covers how mining has shaped technology, war…
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Episode #25: The Third Convergence: When Reality and Digital Collide
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Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the concept of the Third Convergence, a period from 2025 to 2045 where the digital and physical worlds become indistinguishable, creating what Stewart Alsop Jr. calls the "reality disturbance field". Building on the First Convergence (the rise of personal co…
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Episode #434: From the Age of Answers to the Age of Questions
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On this episode of Crazy Wisdom, Stewart Alsop speaks with Dimetri Kofinas, host of Hidden Forces, about the transition from an "age of answers" to an "age of questions." They explore the implications of AI and large language models on human cognition, the role of narrative in shaping society, and the destabilizing effects of trauma on belief syste…
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Episode #433: The Internet Is Toast: Rethinking Knowledge with Brendon Wong
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On this episode of the Crazy Wisdom Podcast, I, Stewart Alsop, sit down with Brendon Wong, the founder of Unize.org. We explore Brendon's work in knowledge management, touching on his recent talk at Nodes 2024 about using AI to generate knowledge graphs and trends in the field. Our conversation covers the evolution of personal and organizational kn…
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Episode #24: From Ethernet to AGI: Tracing the Threads of Connection
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Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the evolution of networking—from the early days of isolated personal computers to the transformative rise of local and wide area networks, and the eventual dominance of the internet. The discussion covers key milestones like Bob Metcalf’s invention of Ethern…
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Episode #432: The Matrix, The Demiurge, and My Digital Soul
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53:47
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In this episode of the Crazy Wisdom Podcast, I, Stewart Alsop, sit down with Louis Anderson, a fascinating thinker whose journey spans biotech hacking, life in San Francisco's hippie communes, and deep involvement in the Urbit ecosystem. Our conversation weaves through topics like secularism, pseudo-religious structures in modern tech communities, …
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