Crazy Wisdom - podcast cover

Crazy Wisdom

Stewart Alsoptwitter.com
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 unrelated subjects, tying together ideas in unconventional ways.

Episodes

Episode #464: From Meme Coins to Mind Melds: Crypto Meets AI

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 what’s truly foundational. Check out this GPT we trained on the conversation Timestamps 00:00 The Intersection of AI and Crypto 01:28 Bitcoin's Origins ...

May 26, 202548 minSeason 15Ep. 94

Episode #463: Brave New Playgrounds: Real-World Games in a Post-Trust Era

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 adults. Ben also shared his journey of teaching himself to code and his philosophy on building experiences centered on human connection rather than pur...

May 23, 20251 hr 11 minSeason 15Ep. 93

Episode #462: The Apostolic Internet: Lines of Authority in a Fractured Age

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 exploration, touching on everything from apostolic succession to the nature of sin and the search for meaning in a secular age. Check out this GPT we t...

May 19, 20251 hr 6 minSeason 15Ep. 92

Episode #461: Morpheus in the Classroom: AI, Education, and the New Literacy

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 at large. Check out this GPT we trained on the conversation Timestamps 01:17 The AI "Cold War": Discussing the intense AI development race between Chin...

May 16, 202556 minSeason 15Ep. 91

Episode #460: Voice First, Future Forward: The AI Agents Are Here

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 the nature of knowledge itself. Check out this GPT we trained on the conversation! Timestamps 00:29 Alex Levin shares that people are often more honest...

May 12, 202553 minSeason 15Ep. 90

Episode #458: How a Tiny Irish Startup Beat Amazon to the Air

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 adoption globally, why Europe is ahead of the U.S., and what it takes to build scalable infrastructure for airborne logistics. The conversation also touch...

May 06, 20251 hr 3 minSeason 15Ep. 88

Episode #457: Surviving the Dark Forest: Cryptography, Tribes, and the End of Institutions

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 like zero-knowledge proofs could defend against deepening informational warfare, the shift toward tribal "patchwork" societies, and the challenge of b...

May 02, 20251 hr 2 minSeason 15Ep. 87

Episode #456: What Happens When Your AI Thinks Like You (On Purpose)

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. They touch on entrepreneurship, inclusive design, and the future of AI as a personal extension of human potential. For more information, visit the P...

Apr 28, 202555 minSeason 15Ep. 86

Episode #455: The End of IPOs and the Rise of Tokenized Everything

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 blockchain starting in 2016, and how Chintai is now helping reshape the financial system through compliant, blockchain-based infrastructure. We talk ab...

Apr 25, 202550 minSeason 15Ep. 85

Episode #453: Trustware vs. Adware: Toward a Humane Stack for Human Life

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 geopolymers as a material path forward. Aaron shared insights from his hands-on restoration work, our shared fascination with Amish tech discernment, and how...

Apr 18, 202559 minSeason 15Ep. 83

Episode #452: Text as Interface: Rethinking Human-Computer Symbiosis

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 we collaborate and think. They explore the abstraction layers of code and consciousness, and why Will believes that better tools for thought are not ...

Apr 14, 202555 minSeason 15Ep. 82

Episode #451: Narrative as Infrastructure: Why Culture Now Runs on Memes

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 open-source AI models are reshaping not just the tools we use, but the very structure of belief and influence in the information age. We touch on ever...

Apr 11, 202557 minSeason 15Ep. 81

Episode #450: 102% Backed and 100% Transparent: Inside the Wyoming Stable Token

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 both a technical unpacking and philosophical meditation on trust, financial sovereignty, and what it means for a government to anchor itself in transp...

Apr 07, 202554 minSeason 15Ep. 80

Episode #449: ​The Strange Loop: How Biology and Computation Shape Each Other

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 immunity; they question whether LLMs are reasoning or just mimicking it; and they explore how scientists navigate the unknown with a kind of embodied int...

Apr 04, 202555 minSeason 15Ep. 79

Episode #448: From Prompt Injection to Reverse Shells: Navigating AI's Dark Alleyways with Naman Mishra

In 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 agents, and even how a simple email summarizer could be exploited to trigger a reverse shell. Naman shares stories like the accidental leak of a Windows a...

Mar 31, 202548 minSeason 15Ep. 78

Episode #447: From Frustration to Creation: Building with Chaos Instead of Blueprints

In 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 and AI, and how the future of education might finally reflect the chaos and creativity of human intelligence. Perry drops insight bombs on ADHD, dyslexi...

Mar 28, 202559 minSeason 15Ep. 77

Episode #446: Decentralized Truth and the Digital Republic

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 more transparently, and how this ties into a broader vision for digital governance using tools like proof of humanity and soulbound tokens. We also ge...

Mar 24, 202551 minSeason 15Ep. 76

Episode #445: How Decentralized Tech Could Challenge Nation-States

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 gray areas emerging around autonomous technology. Rosario shares insights on trusted execution environments, token incentives, and how projects like Pha...

Mar 21, 202551 minSeason 15Ep. 75

Episode #444: The Hidden Frameworks of the Internet: Knowledge Graphs, Ontologies, and Who Controls Truth

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 the Internet Archive in preserving digital history. They also explore the fragility of information in the digital age, the ongoing battle over access t...

Mar 17, 20251 hrSeason 15Ep. 74

Episode #443: Escaping the Algorithm: Building the Future of Social Media with Interoperability

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 reputation, and how to create a digital environment that prioritizes meaningful human connection over algorithmic engagement. The conversation also touches ...

Mar 14, 202558 minSeason 15Ep. 73

Episode #442: Satellites, Strategy, and Staying Profitable: A No-BS Look at Space Tech

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, defense applications, and the shift toward cost-minus procurement models. We also explore the broader implications of satellite technology—from hedge f...

Mar 10, 202559 minSeason 15Ep. 72

Episode #441: Escaping the Algorithm: The Battle for Human Intention

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 expression. Andrew shares insights on the shifting value of art in an AI-driven world, the enduring importance of poetry, and the unexpected resurgence of in-p...

Mar 07, 202538 minSeason 15Ep. 71

Episode #440: AI Agents, Code Wizards, and What Could Possibly Go Wrong?

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 development workflows, and what it means to have swarms of digital agents handling tasks across business and personal life. If you're curious to dive deeper, c...

Mar 03, 202558 minSeason 15Ep. 70

Episode #439: Beyond Second Brains: What AI Is Actually Doing to Knowledg

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 evolution of knowledge management. They also discuss the intersection of cognition, ontologies, and AI’s role in redefining how we structure and retrieve...

Mar 02, 20251 hr 1 minSeason 15Ep. 69

Episode #438: What If AI Is Just the Next Political Revolution?

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 bottlenecks remain. The conversation expands into technology's impact on democracy, the centralization of power, the shifting role of the state, and even th...

Feb 24, 202555 minSeason 15Ep. 68

Episode #437: From Garage Sales to Multi-Million Dollar E-Commerce Empires

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 the philosophical implications of accelerationism and capitalism's efficiency. Jason shares his personal journey in building SureDone, lessons from s...

Feb 21, 202537 minSeason 15Ep. 67

Episode #436: How AI Will Reshape Power, Governance, and What It Means to Be Human

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 alternative. Roko also introduces the concept of ICE colonization—why space colonization might be a mistake and why the oceans could be the key to humanity’...

Feb 17, 202553 minSeason 15Ep. 66

Episode #435: How AI, Drones, and Rare Earths Will Decide the Next Global Conflict

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, warfare, and supply chains. They discuss the strategic importance of minerals like gallium and germanium, the rise of drone warfare, and the ongoing batt...

Feb 14, 202559 minSeason 15Ep. 64

Episode #434: From the Age of Answers to the Age of Questions

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 systems. The conversation touches on media manipulation, the intersection of technology and consciousness, and the existential dilemmas posed by transhuman...

Feb 10, 20251 hr 2 minSeason 15Ep. 65

Episode #433: The Internet Is Toast: Rethinking Knowledge with Brendon Wong

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 knowledge management, the future of object-oriented systems, the integration of AI with knowledge graphs, and the challenges of autonomous agents. For m...

Feb 07, 202554 minSeason 15Ep. 63
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