Shows
Stewart SquaredEpisode #59: When Information Became the New EmpireIn this episode, Stewart Alsop III speaks with his father, Stewart Alsop II, about Hong Kong’s transformation since the 1997 handover and what it reveals about power, identity, and control in the information age. Together, they trace the shifting relationship between surveillance and sovereignty, explore how technology and data have become new instruments of hard power, and question what autonomy means in a world increasingly defined by networks and algorithms.Check out this GPT we trained on the conversationTimestamps00:00 The Alsops open with reflections on Hong Kong’s post-handover identity and what sove...
2025-10-1645 min
Crazy WisdomEpisode #497: The Demiurge, the Divine, and the Data: Rethinking God in the Age of AIIn this episode of Crazy Wisdom, host Stewart Alsop sits down with Sam Barber for a wide-ranging conversation about faith, truth, and the nature of consciousness. Together they explore the difference between faith and belief, the limits of language in describing spiritual experience, and how frameworks like David Hawkins’ Map of Consciousness help us understand vibration, energy, and love as the core of reality. The discussion touches on Christianity, Buddhism, the demiurge, non-duality, demons, AI, death, and what it means to wake up from the illusion of separation. Sam also shares personal stories of transformation, intuitive experience, and his re...
2025-10-1358 min
Crazy WisdomEpisode #496: Bitcoin After the Hype: A Conversation with Paul Sztorc on What’s RealIn this episode of Crazy Wisdom, host Stewart Alsop speaks with Paul Sztorc, CEO of Layer2 Labs, about Bitcoin’s evolution, the limitations of the Lightning Network, and how his ideas for drivechains and merge-mined sidechains could transform scalability and privacy on the Bitcoin network. They cover everything from Zcash’s zero-knowledge proofs and “moon math” to the block size wars, sound money, and the economic realities behind crypto hype cycles. Paul also explains his projects like Zside and Thunder, which aim to bring features like Zcash-style privacy and high-speed transactions to Bitcoin. Listeners can try Layer2 Labs’ software or learn m...
2025-10-101h 15
Stewart SquaredEpisode #58: Inventing Wonder: A Conversation with the BushnellsIn this episode, Stewart Alsop II, Stewart Alsop III, Brent Bushnell, and a brief appearance by Nolan Bushnell come together for a thoughtful exchange about the evolution of immersive entertainment, mixed reality, and playful learning. The conversation touches on creativity through technology, the merging of physical and digital worlds, and the Bushnell family’s legacy of innovation across art, engineering, and entrepreneurship. Check out this GPT we trained on the conversationTimestamps00:00 – Stewart Alsop II and Stewart Alsop III open the conversation with Brent Bushnell, setting the stage around creativity, play, and immersive expe...
2025-10-0951 min
Crazy WisdomEpisode #495: The Black Box Mind: Prompting as a New Human ArtIn this episode of Crazy Wisdom, host Stewart Alsop talks with Jared Zoneraich, CEO and co-founder of PromptLayer, about how AI is reshaping the craft of software building. The conversation covers PromptLayer’s role as an AI engineering workbench, the evolving art of prompting and evals, the tension between implicit and explicit knowledge, and how probabilistic systems are changing what it means to “code.” Stewart and Jared also explore vibe coding, AI reasoning, the black-box nature of large models, and what accelerationism means in today’s fast-moving AI culture. You can find Jared on X @imjaredz and learn more or sign...
2025-10-0657 min
Crazy WisdomEpisode #494: Recursive Loops, Cult Startups, and the Mirage of AIIn this episode of Crazy Wisdom, host Stewart Alsop sits down with Lord Asado to explore the strange loops and modern mythologies emerging from AI, from doom loops, recursive spirals, and the phenomenon of AI psychosis to the cult-like dynamics shaping startups, crypto, and online subcultures. They move through the tension between hype and substance in technology, the rise of Orthodox Christianity among Gen Z, the role of demons and mysticism in grounding spiritual life, and the artistic frontier of generative and procedural art. You can find more about Lord Asado on X at x.com/LordAsado....
2025-10-031h 04
Stewart SquaredEpisode #57: Silicon, Sovereignty, and Speculation: The Stakes of AI’s Next PhaseIn this episode of Stewart Squared, Stewart Alsop sits down with his father, Stewart Alsop II, for a wide-ranging conversation that moves from OpenAI’s massive semiconductor and Oracle deals, to the nature of money and the gold standard, to shifting dynamics in U.S.–China relations and modern warfare technologies like drones and cyber tools. They also trace the history of networking and video games—from LAN parties and Atari with Nolan Bushnell to immersive experiences like 2-Bit Circus and Meow Wolf—before circling back to how AI and robotics are beginning to reshape both business and reality itself.
2025-10-0259 min
Crazy WisdomEpisode #493: Decentralization as Culture: Trust, Truth, and the Future of ConnectionOn this episode of Crazy Wisdom, Stewart Alsop talks with Agustin Ferreira, founder of Neurona, an AI community in Buenos Aires. Their conversation moves through Argentina’s history with economic crises and the rise of crypto as an alternative to failing institutions, the importance of Ethereum and smart contracts, the UX challenges that still plague crypto adoption, and how AI and agents could transform the way people interact with decentralized systems. They also explore the tension between TradFi and DeFi, questions of data privacy and surveillance, the shifting role of social networks, and even the cultural and philosophical meaning of...
2025-09-2955 min
Stewart SquaredEpisode #56: The Internet’s Business Model Is Cracking..What Comes Next?In this episode of Stewart Squared, Stewart Alsop III sits down with Stewart Alsop II to talk about Cloudflare, its role as the “network administrator” of the internet, and how its business model connects to the larger shifts happening with AI, content, and regulation. The conversation moves through Cloudflare’s core services—CDN, DDoS protection, DNS, zero trust security, and more—before branching into AI’s impact on the open web, lawsuits over training data, Anthropic’s billion-dollar book settlement, and Google’s changing monopoly status. Along the way, they compare today’s uncertainty around AI to the early commercialization...
2025-09-2543 min
Crazy WisdomEpisode #491: Mystical Continuities from the Desert to the Digital AgeIn this episode, Stewart Alsop speaks with Nico Sarian, Executive Director of the Eternity Foundation and PhD candidate in Religious Studies, about the strange currents that run through Armenian history, the fractured birth of early Christianity, and the survival of Gnostic and Hermetic traditions into the Renaissance. The conversation weaves through questions of empire and nation state, mysticism and metaphysics, the occult roots of modern science, and the unsettling horizon of accelerationism, drawing unexpected lines between the ancient world, the bureaucratic order critiqued by David Graeber, and our present entanglement with surveillance and identity. For more on Nico’s wo...
2025-09-221h 21
Crazy WisdomEpisode #490: The Remnant and the Machine: Staying Human in an Age of ControlIn this episode of Crazy Wisdom, Stewart Alsop speaks with Samuel, host of The Remnant Podcast, about the intersections of biblical prophecy, Gnostic traditions, transhumanism, and the spiritual battle unfolding in our age. The conversation moves from Dr. David Hawkins’ teachings and personal encounters with the Holy Spirit to questions of Lucifer, Archons, and the distortions of occult traditions, while also confronting timelines of 2025, 2030, and 2045 in light of technological agendas from Palantir, Neuralink, and the United Nations. Together they explore the tension between organic human life and the merging with machines, weaving in figures like Blavatsky, Steiner, and Barbara Ma...
2025-09-1957 min
Stewart SquaredEpisode #55: From Justin.tv to Claude Hacks: Lessons in Tech, Money, and SecurityIn this episode of Stewart Squared, Stewart Alsop III sits down with Stewart Alsop II to explore the financial and technical foundations shaping today’s AI and cloud economy, from the staggering scale of CapEx and depreciation schedules to the sustainability of investments by Microsoft, Meta, OpenAI, and Anthropic. The conversation traces historical precedents like the fiber boom, Google’s rise, and the pivot from Justin.tv to Twitch, leading into a discussion of venture capital shifts, IPO trends, and the enduring importance of the “rule of 40.” They also examine Cloudflare’s emerging role in the open internet economy, the rise o...
2025-09-1857 min
Crazy WisdomEpisode #489: The Music Maker’s Stack: From Spotify to On-Chain RevenueOn this episode of Crazy Wisdom, I, Stewart Alsop, sit down with Sweetman, the developer behind on-chain music and co-founder of Recoup. We talk about how musicians in 2025 are coining their content on Base and Zora, earning through Farcaster collectibles, Sound drops, and live shows, while AI agents are reshaping management, discovery, and creative workflows across music and art. The conversation also stretches into Spotify’s AI push, the “dead internet theory,” synthetic hierarchies, and how creators can avoid future shock by experimenting with new tools. You can follow Sweetman on Twitter, Farcaster, Instagram, and try Recoup at chat.recoup...
2025-09-151h 04
Crazy WisdomEpisode #488: Responsibility as Freedom, Belonging as WealthIn this episode of Crazy Wisdom, host Stewart Alsop sits down with Hannah Aline Taylor to explore themes of personal responsibility, freedom, and interdependence through her frameworks like the Village Principles, Distribution Consciousness, and the Empowerment Triangle. Their conversation moves through language and paradox, equanimity, desire and identity, forgiveness, leadership, money and debt, and the ways community and relationship serve as our deepest resources. Hannah shares stories from her life in Nevada City, her perspective on abundance and belonging, and her practice of love and curiosity as tools for living in alignment. You can learn more about her work...
2025-09-121h 00
Stewart SquaredEpisode #54: Preference Stacks, Power Games, and the Future of WarIn this episode of Stewart Squared, Stewart Alsop III and Stewart Alsop II explore the mechanics of the preference stack in venture investing, the difference between economic and voting rights, why Delaware dominates incorporation, and how governance plays out through independent directors and board structures. The conversation ranges from startup financing and information asymmetry to the U.S. government’s new equity stake in Intel under the CHIPS Act, the precedent of the GM bailout, and the Defense Department’s secure enclave program. They trace the lineage from ARPA to DARPA, contrast research versus development, and examine how primes lost...
2025-09-1144 min
Crazy WisdomEpisode #487: Stablecoins as Weapons, Bitcoin as Escape: A Conversation on Money and ControlOn this episode of Crazy Wisdom, Stewart Alsop sits down with Abhimanyu Dayal, a longtime Bitcoin advocate and AI practitioner, to explore how money, identity, and power are shifting in a world of deepfakes, surveillance, automation, and geopolitical realignment. The conversation ranges from why self-custody of Bitcoin matters more than ETFs, to the dangers of probabilistic biometrics and face-swap apps, to the coming impact of AGI on labor markets and the role of universal basic income. They also touch on India’s refinery economy, its balancing act between Russia, China, and the U.S., and how soft power is er...
2025-09-0849 min
Crazy WisdomEpisode #486: Sovereignty by Markets: How Futarchy Turns Bets into DecisionsIn this episode of Crazy Wisdom, host Stewart Alsop speaks with Robin Hanson, economist and originator of the idea of futarchy, about how conditional betting markets might transform governance by tying decisions to measurable outcomes. Their conversation moves through examples of organizational incentives in business and government, the balance between elegant theories and messy implementation details, the role of AI in robust institutions, and the tension between complexity and simplicity in legal and political systems. Hanson highlights historical experiments with futarchy, reflects on polarization and collective behavior in times of peace versus crisis, and underscores how ossified bureaucracies mirror...
2025-09-051h 00
Stewart SquaredEpisode #53: Cycles of Scaling: How AI and Politics Break SystemsIn this episode of Crazy Wisdom, I, Stewart Alsop III, talk with my father, Stewart Alsop II, about the surprising reception of ChatGPT, the role of AI as a modern chaos agent, and the ways disruptive forces echo both in technology and politics. Our conversation weaves through corporate rivalries, the scaling challenges that shape giants of industry, and the geopolitical pressures facing nations like Argentina and Brazil under the IMF. We also draw on history—from Rome and the Iroquois to the early internet and the Telecommunications Act—to explore cycles of rise and decline, before turning to the pers...
2025-09-0454 min
Crazy WisdomEpisode #485: Bitcoin as Silent Revolution, AI as Accelerated IntelligenceOn this episode of Crazy Wisdom, Stewart Alsop sits down with Brad Costanzo, founder and CEO of Accelerated Intelligence, for a wide-ranging conversation that stretches from personal development and the idea that “my mess is my message” to the risks of AI psychosis, the importance of cognitive armor, and Brad’s sovereign mind framework. They talk about education through the lens of the Trivium, the natural pull of elites and hierarchies, and how Bitcoin and stablecoins tie into the future of money, inflation, and technological deflation. Brad also shares his perspective on the synergy between AI and Bitcoin, the danger...
2025-09-011h 08
Crazy WisdomEpisode #484: Pirates, Black Swans, and Smart Contracts: Rethinking Insurance in DeFiIn this episode of Crazy Wisdom, host Stewart Alsop sits down with Juan Samitier, co-founder of DAMM Capital, for a wide-ranging conversation on decentralized insurance, treasury management, and the evolution of finance on-chain. Together they explore the risks of smart contracts and hacks, the role of insurance in enabling institutional capital to enter crypto, and historical parallels from Amsterdam’s spice trade to Argentina’s corralito. The discussion covers stablecoins like DAI, MakerDAO’s USDS, and the collapse of Luna, as well as the dynamics of yield, black swan events, and the intersection of DeFi with AI, prediction markets, and to...
2025-08-2954 min
Stewart SquaredEpisode #52: The Illusion of Choice in Big TechIn this episode of Stewart Squared, Stewart Alsop sits down with his father, Stewart Alsop II, for a wide-ranging conversation on the frustrations of modern UI/UX, Microsoft’s struggles with spam and AI adoption, Google’s approach to knowledge management, and the broader lessons of technological hype cycles from fiber optics to GPT-5. Together they explore how big companies evolve from serving programmers to serving enterprises, touch on the role of regulatory capture in shaping user experiences, and recall stories of early email, Hotmail, AOL, and long-distance calls in the 1960s. Along the way, they connect today’s debate...
2025-08-2852 min
Crazy WisdomEpisode #483: The Limits of Logic: Probabilistic Minds in a Messy WorldIn this episode of Crazy Wisdom, Stewart Alsop sits down with Derek Osgood, CEO of DoubleO.ai, to talk about the challenges and opportunities of building with AI agents. The conversation ranges from the shift from deterministic to probabilistic processes, to how humans and LLMs think differently, to why lateral thinking, humor, and creative downtime matter for true intelligence. They also explore the future of knowledge work, the role of context engineering and memory in making agents useful, and the culture of talent, credentials, and hidden gems in Silicon Valley. You can check out Derek’s work at doubleo.ai...
2025-08-2549 min
Stewart SquaredEpisode #51: Ray-Bans, Apple Stock, and the Long Game of Power and TimingIn this episode of Stewart Squared, both Stewarts have a wide-ranging conversation that jumps from Claude and Anthropic’s aggressive move against OpenAI employees to the deep history of corporations stretching back to Rome and the East India Company, the mechanics of preferred versus common shares in venture capital, and the recent Figma IPO. Along the way, they contrast speculation and perception in tech markets with hard fundamentals, debate the trajectories of Meta, Apple, and Microsoft in the age of AI, and explore how accounting principles shape both businesses and governments. The discussion widens into geopolitics, from China’s cent...
2025-08-2156 min
Crazy WisdomEpisode #481: From Rothschilds to Robinhood: Cycles of Finance and ControlOn this episode of Crazy Wisdom, host Stewart Alsop speaks with Michael Jagdeo, a headhunter and founder working with Exponent Labs and The Syndicate, about the cycles of money, power, and technology that shape our world. Their conversation touches on financial history through The Ascent of Money by Niall Ferguson and William Bagehot’s The Money Market, the rise and fall of financial centers from London to New York and the new Texas Stock Exchange, the consolidation of industries and the theory of oligarchical collectivism, the role of AI as both tool and chaos agent, Bitcoin and “quantitative re-centralization,” the dy...
2025-08-1858 min
Crazy WisdomEpisode #480: The Patchwork Age and Why AI Can’t Grasp the Human StoryIn this episode of Crazy Wisdom, Stewart Alsop talks with Paul Spencer about the intersection of AI and astrology, the balance of fate and free will, and how embodiment shapes human experience in time and space. They explore cultural shifts since 2020, the fading influence of institutions, the “patchwork age” of decentralized communities, and the contrasts between solar punk and cyberpunk visions for the future. Paul shares his perspective on America’s evolving role, the symbolism of the Aquarian Age, and why philosophical, creative, and practical adaptability will be essential in the years ahead. You can connect with Paul and explor...
2025-08-151h 30
Stewart SquaredEpisode #50: Star Hubs, Server Farms, and the Strange New Geography of AIIn this episode, Stewart Alsop III talks with Stewart Alsop II about Cloudflare’s role in modern internet infrastructure, from its origins with Project Honeypot to its massive global network powering HTTPS, reverse proxies, DNS integration, and zero-trust systems. The conversation weaves through the evolution of enterprise networking since the Cisco-dominated 1990s, the growth of server farms and AI clusters, the history of dark fiber and undersea cables, and how Web 2.0, social media, crypto mining, and today’s generative AI have shaped bandwidth demand. They explore Cloudflare’s new pay-to-scrape policy, the business dynamics with Google, the rise of high-q...
2025-08-1457 min
Crazy WisdomEpisode #479: From Bitcoin to Birdsong: Building Trust in a World of FakesIn this episode of Crazy Wisdom, Stewart Alsop talks with Cathal, founder of Poliebotics and creator of the “truth beam” system, about proof of liveness technology, blockchain-based verification, projector-camera feedback loops, physics-based cryptography, and how these tools could counter deepfakes and secure biodiversity data. They explore applications ranging from conservation monitoring on Cathal’s island in Ireland to robot-assisted farming, as well as the intersection of nature, humanity, and AI. Cathal also shares thoughts on open-source tools like Jitsi and Element, and the cultural shifts emerging from AI-driven creativity. Find more about his work and Poliebotics in Github and Twitte...
2025-08-111h 15
Stewart SquaredEpisode #49: The Next Internet Is Immersive ExperienceIn this episode of Stewart Squared, host Stewart Alsop talks with Vince Kadlubek, founder and Chief Vision Officer of Meow Wolf, about the evolution of immersive art, post-capitalist creativity, and the future of human imagination. They explore how Meow Wolf emerged from a decentralized art collective using recycled materials into a boundary-pushing, experience-driven company with hundreds of creatives on staff. Topics include the tension between business and creativity, alternate reality as a medium, the legacy of the 1960s counterculture, AI's impact on art, and building meaningful physical experiences in a media-saturated world.Check out this GPT...
2025-08-0757 min
Crazy WisdomEpisode #476: More Than Magic: Astrology as the Oldest Data ScienceIn this episode of Crazy Wisdom, host Stewart Alsop sits down with astrologer and researcher C.T. Lucero for a wide-ranging conversation that weaves through ancient astrology, the evolution of calendars, the intersection of science and mysticism, and the influence of digital tools like AI on symbolic interpretation. They explore the historical lineage from Hellenistic Greece to the Persian golden age, discuss the implications of the 2020 Saturn-Jupiter conjunction, touch on astrocartography, and reflect on the information age's shifting paradigms. For more on the guest's work, check out ctlucero.com.Check out this GPT we trained on the...
2025-08-011h 09
Stewart SquaredEpisode #48: The Slow Death of Social Media (And What Comes Next)Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation orbits around the mechanics and ethics of digital walled gardens, from YouTube’s curated algorithms to Meta’s domination of social platforms like Threads and Instagram. The Stewarts reflect on relevance in tech, the decline of platforms like Quora, the ascent of Substack, and the meaning of audience ownership in a fractured media landscape. They explore marketing not as manipulation but as a hunt for shared value, and weigh the implications of spam, AI's blind spots, and even political messaging strategies.Check out...
2025-07-3135 min
Crazy WisdomEpisode #475: The Illusion We Opt Into: VR, AI, and the Fractals of RealityIn this episode of Crazy Wisdom, host Stewart Alsop speaks with Ryan Estes about the intersections of podcasting, AI, ancient philosophy, and the shifting boundaries of consciousness and technology. Their conversation spans topics like the evolution of language, the impact of AI on human experience, the role of sensory interfaces, the tension between scientism and spiritual insight, and how future technologies might reshape power structures and daily life. Ryan also shares thoughts on data ownership, the illusion of modern VR, and the historical suppression of mystical knowledge. Listeners can connect with Ryan on LinkedIn and check out his podcast...
2025-07-2847 min
Stewart SquaredEpisode #47: The Cost of Knowing EverythingWelcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they navigate a sprawling conversation that begins with the unruly complexity of the modern browser and spirals into deeper territory—from Google’s jealous leap into the browser wars with Chrome, to the philosophical implications of Neuralink and the idea of owning one’s own data and mind. Stewart Alsop interviews his co-host Stewart on themes like the architecture of the internet, the anti-fragility of figures like Musk and Trump, and the evolving coordination costs of technology in both business and AI. Along the way, they touch...
2025-07-2446 min
Crazy WisdomEpisode #473: Breaking the Parasite Spell: Metabolic Healing and Remembering Who We AreOn this episode of Crazy Wisdom, Stewart Alsop talks with Larry Diamond, co-founder of Healing with the Diamonds, about his journey from severe metabolic illness to vibrant health and his work helping others do the same. They explore topics like heart-brain coherence, the alchemical journey, insulin resistance, seed oils, and the deeper spiritual dimensions of healing, weaving in references to David Hawkins, Rupert Sheldrake, and the lost wisdom of the divine feminine. Larry shares insights on metabolic testing, ancestral eating, and the importance of authentic living, while also touching on the role of parasites—his term for the forces ke...
2025-07-2158 min
Crazy WisdomEpisode #471: Truth-Seeking Entrepreneurs and the Future of InnovationIn this episode of Crazy Wisdom, I, Stewart Alsop, speak with Thamir Ali Al-Rahedi, host of the From First Principles podcast on YouTube, about the nature of questions and answers, their role in business and truth-seeking, and the trade-offs inherent in technologies like AI. We explore the tension between generalists and specialists, the influence of scientism on culture, and how figures like Steve Jobs embodied the power of questions to shape markets and innovations. Thamir also shares insights from his Arabic book summary platform and his cautious approach to using large language models. You can find Thamir’s work on...
2025-07-1452 min
Stewart SquaredEpisode #44: Consultants Preach, AI Learns, and CEOs Fall BehindWelcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore why consultants often fail in the tech world, how leadership skills are (or aren’t) taught in business schools, and the historical tension between technical and non-technical CEOs. They trace the evolution of Silicon Valley’s culture, from the idealistic hackers of the PC revolution to Amazon’s strategic rise with AWS and its CIA contract, and discuss whether institutional knowledge should be centralized or decentralized inside corporations. The conversation ranges from the origins of corporations and supply chain mastery at Apple, to predictions with L...
2025-07-0353 min
Crazy WisdomEpisode #468: Forecasting the Market’s Weather: Events, AI, and the Future of TradingIn this episode of Crazy Wisdom, I, Stewart Alsop, speak with Andrew Einhorn, CEO and founder of Level Fields, a platform using AI to help people navigate financial markets through the lens of repeatable, data-driven events. We explore how structured patterns in market news—like CEO departures or earnings surprises—can inform trading strategies, how Level Fields filters noise from financial data, and the emotional nuance of user experience design in fintech. Andrew also shares insights on knowledge graphs, machine learning in finance, and the evolving role of narrative in markets. Stock tips from Level Fields are available on thei...
2025-06-2354 min
Stewart SquaredEpisode #41: Homebrew Aftershocks: Echoes from the Pre-Platform EraWelcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, father and son trace the tectonic shifts that shaped Silicon Valley—from the amateur hardware tinkerers at the Homebrew Computer Club to the institutional rise of venture capital and its entanglement with military-industrial imperatives. They explore how Boston, Texas, and even Johannesburg played pivotal but ultimately eclipsed roles in the story, and how Silicon Valley's dominance crystallized through a nexus of research labs, open-minded capital, and cultural disruption. Alongside this historical cartography, they reflect on the layered timelines of big science, Cold War paranoia, and the co...
2025-06-1250 min
Stewart SquaredEpisode #40: Probabilistic Machines: Living with the Illusion of ControlWelcome to Stewart Squared podcast with the two Stewart Alsops, where this episode takes you on a ride through vibe coding experiments, AI-powered doom loops, and the fading utility of language learning apps like Duolingo in a world of real-time translation glasses. Stewart Alsop shares how he replaced Descript with Claude-generated code, while Stewart II unpacks the uncanny valley between needing to understand code and getting the machine to do it for you. They riff on the evolution of Apple’s infrastructure, Unix origins, the role of kernels, and Microsoft’s unlikely embrace of open source. There’s also a trib...
2025-06-051h 01
Stewart SquaredEpisode #39: Trust Issues: From Meme Coins to MainframesWelcome 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 store monopolies. We compare Apple’s branding collapse to meme coin absurdity, reflect on the fallout from 2008, and wrestle with whether open source and individual agency can still offer an exit ramp. Sam Altman, Trump, China, and the Ap...
2025-05-2957 min
Crazy WisdomEpisode #463: Brave New Playgrounds: Real-World Games in a Post-Trust EraI, 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 pure profit.Check out this GPT we trained on the conversationTimestamps00:55 Ben Roper on AI's...
2025-05-231h 11
Crazy WisdomEpisode #461: Morpheus in the Classroom: AI, Education, and the New LiteracyI, 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 conversationTimestamps01:17 The AI "Cold War": Discussing the intense AI development race between China and the US.03:04 Opaque Models & Education's Resistance: The challenge of opaque AI...
2025-05-1656 min
Stewart SquaredEpisode #37: Elegance vs. Exquisite: Rethinking Systems Old and NewI, 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 In-Q-Tel for the CIA and the eventual creation of Alsop Louie Partners. It was a fascinating look at decades of technological evolution, strategic thinking, and the stories behind some major innovations.Check out this GPT we trained on the conversation
2025-05-1559 min
Crazy WisdomEpisode #459: AI, Mate, and the End of Web Dev as We Knew ItIn this episode of the Crazy Wisdom Podcast, I, Stewart Alsop, talk with AJ Beckner about how AI is reshaping the terrain of software development—from the quiet ritual of mate-fueled coding sessions to the radical shift in DevOps, tool use, and what it means to build software in a post-LLM world. AJ shares insights from his time in the Gauntlet AI program, reflecting on how platforms like Cursor, Lovable, and Supabase are changing what’s possible for both seasoned engineers and newcomers alike. We also explore the nuanced barbell dynamic of skill disruption, the philosophical limits of current AI t...
2025-05-0951 min
Stewart SquaredEpisode #36: Tiny Computers, Massive Shifts: The iPhone’s Quiet CoupWelcome 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—deceptively quiet between the dot-com crash and the smartphone boom—were in fact the foundation for the modern Internet, with fiber laid during the crash powering today's broadband-dependent innovations. From Apple's cautious approach to third-party apps to the implications of subscription economics born partly out of mobi...
2025-05-081h 00
Crazy WisdomEpisode #458: How a Tiny Irish Startup Beat Amazon to the AirIn 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 touches on the future of aerial mobility, the implications of automation for local commerce, and the philosophical impacts of deflationary technologies. For mo...
2025-05-061h 03
Crazy WisdomEpisode #454: From Zero to Git: A Founder’s Guide to the TerminalIn this episode, I, Stewart Alsop III, sat down with AJ Beckner to walk through how non-technical founders can build a deeper understanding of their codebase using AI tools like Cursor and Claude. We explored the reality of navigating an IDE as a beginner, demystified Git and GitHub version control, and walked through practical ways to clone a repo, open it safely in Cursor, and start asking questions about your app’s structure and functionality without breaking anything. AJ shared his curiosity about finding specific text in his app and how to track that down across branches. We also lo...
2025-04-211h 04
Crazy WisdomEpisode #453: Trustware vs. Adware: Toward a Humane Stack for Human LifeOn 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 course-correcting digital dependencies can restore sovereignty. We also explored what it means to design for long-term human flourishing in a...
2025-04-1858 min
Stewart SquaredEpisode #32: Startups, Deadlines, and Drift: The Venture Logic Behind Modern NewsroomsWelcome 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 the structural mismatches that still shape newsrooms and tech companies alike. Topics range from John Doerr’s influence on startup thinking to the archival black holes created by neglected knowledge systems.Check out this GPT we trained on the conversation!...
2025-04-1052 min
Crazy WisdomEpisode #449: The Strange Loop: How Biology and Computation Shape Each OtherIn 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 intuition. For more about German’s work, you can connect with him through email at germanjurado7@gmail.com....
2025-04-0455 min
Crazy WisdomEpisode #448: From Prompt Injection to Reverse Shells: Navigating AI's Dark Alleyways with Naman MishraIn 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 activation key via an LLM and explains why red teaming isn’t just a checkbox, but a continuous mindset. If you want to lea...
2025-03-3147 min
Stewart SquaredEpisode #30: From InfoWorld to x.com: The Patterns That RepeatWelcome 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 it means to be an editor. Alongside reflections on the newsletter era, the internet boom, and the looming AI shift, there’s a core thread about editing as a form of pattern recognition and meaning-making.Check out this GPT...
2025-03-2753 min
Stewart SquaredEpisode #29: Bridging the Physical and Digital: Investing in the Next Big ShiftWelcome 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 computing, the internet, and mobile technology, drawing connections to past industry shifts and the role of venture capital in funding the future. Jim also reflects on his experiences with Apple, Lucasfilm, and launching groundbreaking campaigns like PowerBook and Windows 95.Check out this GPT we...
2025-03-201h 00
Crazy WisdomEpisode #444: The Hidden Frameworks of the Internet: Knowledge Graphs, Ontologies, and Who Controls TruthOn 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 to knowledge, and how AI is shaping—and being shaped by—structured data and knowledge graphs. To connect with Jessica Talisman, you can reach her...
2025-03-171h 00
Stewart SquaredEpisode #25: The Third Convergence: When Reality and Digital CollideWelcome 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 computing and digital media) and the Second Convergence (the networked internet revolution), this new era promises profound shifts in technology, human behavior, and society. We discuss augmented reality, artificial intelligence, and the implications of immersive digital experiences, touching on everything from Pokemon Go to the Apple Vision...
2025-02-1353 min
Crazy WisdomEpisode #434: From the Age of Answers to the Age of QuestionsOn 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 transhumanism. For more from Dimetri, check out hiddenforces.io.Check out this GPT we trained on the conversation!...
2025-02-101h 02
Crazy WisdomEpisode #424: Resonance Revolution: Marketing, Neuroscience, and the Future of Human Decision-MakingIn this episode of the Crazy Wisdom Podcast, host Stewart Alsop is joined by Christopher Demetrakos, founder and CEO of Manzanita KK, a neuroscience-based marketing consultancy in Japan. Together, they explore a wide range of topics, including the evolution of marketing from intuition-driven strategies to neurochemistry-based resonance, the mechanics of human decision-making, and the implications of new technologies like LLMs and immersive advertising tools. They also tackle profound questions about societal shifts, cultural identities, and the future of humanity in an era of technological acceleration. For more on Christopher’s work, you can find him under the username "Demetrakos" ac...
2025-01-061h 13
Crazy WisdomEpisode #417: Layers of Power: Language, Tech, and the New Rules of Free SpeechOn this episode of the Crazy Wisdom Podcast, host Stewart Alsop is joined by Katelynne Schuler, a thinker and innovator in the realms of psychology, religion, and philosophy. The conversation spans a wide range of compelling topics, including the layered nuances of Korean social hierarchy, the evolution of political language, and the shifting ideologies within Western conservatism. They explore the rebranding of the KKK, the deeper implications of free speech in a world dominated by digital platforms, and the unseen influence of corporations on government censorship. Katelynne also shares her insights on the psychology of "falls from grace" and...
2024-12-131h 08
Crazy WisdomEpisode #416: AI, Attention, and the Battle for Reality: A Mind-Bending Journey with Eric FisherIn this episode of the Crazy Wisdom Podcast, host Stewart Alsop reconnects with Eric Fisher, one of the show’s earliest guests. Their conversation weaves through profound topics like the evolution of AI, the potential consequences of large language models (LLMs), and how AI might reshape both spirituality and education. Eric shares reflections from his time at Facebook, offering behind-the-scenes insight into the creation of algorithmic feeds and how those decisions echo into today's world of AI-driven interactions. Together, Stewart and Eric explore the nature of human attention, the future of work, and the potential divide between tech-driven living an...
2024-12-0955 min
Crazy WisdomEpisode #414: AI vs. Human Potential: Stewart Alsop III and Alexander Explore What’s NextOn this episode of the Crazy Wisdom Podcast, host Stewart Alsop chats with Alexander, a Gen Z innovator passionate about technology, particularly AI and blockchain. Together, they explore Alexander’s creative approach to tackling challenges like reading dense white papers, the dynamics of AI in software engineering, and the philosophical implications of emerging tech, from blockchain’s elegant simplicity to AI's transformative potential in reshaping industries. Alexander also shares insights from his journey in crypto and smart contract development, providing a glimpse into how technology and human ingenuity intertwine in the modern era. For more, follow Alexander on X at...
2024-12-021h 05
Stewart SquaredEpisode #17: From California to Buenos Aires: Gaming Bureaucracies in the Digital AgeWelcome to Stewart Squared podcast with the two Stewart Alsops! This episode explores the fascinating concept of residency hacking, blending digital nomadism with innovative approaches to establishing legal residency in multiple jurisdictions. Stewart Alsop II discusses his transition from California to Buenos Aires, strategies for obtaining Argentinian residency and citizenship, and the unique appeal of South Dakota for U.S. state residency. Along the way, the conversation touches on global mobility, bureaucratic challenges, and evolving political and economic systems.Check out this GPT we trained on the conversation!Timestamps00:00 Introduction...
2024-11-2547 min
Crazy WisdomEpisode #410: From Space Economies to Spiritual Roots: Technology’s Role in Shaping HumanityOn this episode of the Crazy Wisdom Podcast, Stewart Alsop sits down with Ben Kohlmann, an investment partner at Qubit Capital, to discuss topics ranging from Argentina’s socio-political shifts and libertarian experimentation to frontier technologies like AI, space exploration, and energy abundance. Ben shares his insights on how technology can enhance human flourishing, grounded in both innovation and a philosophical perspective. The conversation touches on everything from cultural and historical shifts to the future of interplanetary economies and the challenges of regulatory frameworks in space. You can connect with Ben on Twitter @BenKohlmann or email him at ben@cu...
2024-11-1851 min
Crazy WisdomEpisode #407: Transhumanism Lite: Using Urbit and Spaced Repetition to Hack Your Brain, Not Replace ItIn this episode of Crazy Wisdom, Stewart Alsop hosts ~littel-wolfur to explore spaced repetition, the dynamics of learning algorithms, and the philosophy behind Urbit. They break down Urbit’s promise as a peer-to-peer platform with roots in a deep, almost otherworldly commitment to resilience and a long time horizon. Alongside ~littel-wolfur’s take on memory as the strange balance of laziness and persistence, they dig into shrubbery, Urbit's latest namespace innovation, and the challenge of creating tools that last. From generational shifts to the philosophy of technology, Stewart and ~littel-wolfur contemplate whether Urbit’s rebellious craftsmanship might be the founda...
2024-11-0857 min
Crazy WisdomEpisode #406: The Productive Side of AI: Moving from Consumption to CreationIn this episode of the Crazy Wisdom Podcast, host Stewart Alsop welcomes Leon Coe, founder of Amplify Intelligence, to explore the cutting edge of AI and its practical applications in workflows, agentic systems, and beyond. They discuss the evolution of autonomous agents, the shift toward combining traditional code with large language models, and how these integrations are reshaping both business processes and personal productivity. The conversation touches on the potential for AI to transform repetitive tasks, the role of probabilistic versus deterministic AI models, and Leon’s perspective on the future of a more AI-enabled economy. Leon also shares th...
2024-11-0456 min
Crazy WisdomEpisode #405: The New Digital Nomad Dilemma: Financial Advice for an Untethered LifeIn this episode of Crazy Wisdom Podcast, Stewart Alsop is joined by Jenna Biancavilla, a multi-entrepreneur and founder in financial services and tech. They discuss Jenna’s experience navigating complex regulatory landscapes in finance, her insights into global work dynamics, and her unique approach to asset management for business owners and families. Stewart and Jenna also cover the challenges of building a tech platform from the ground up, exploring cultural and logistical hurdles along the way. You can check out Jenna’s latest venture at BeSvvy.com where she connects clients with trusted advisors.Check out this GPT...
2024-11-0154 min
Stewart SquaredEpisode #14: How We Got Here: A Journey Through Tech’s Defining WavesWelcome to Stewart Squared podcast with the two Stewart Alsops! This week’s episode takes you through decades of technological evolution, from Stewart Alsop II’s early experiences with personal computing and the internet boom to today’s era of AI and space exploration. They dive into how technology adoption has shaped our lives, discuss the cultural impacts of tools like VisiCalc and Mosaic, and explore the big shifts driven by Starlink and generative AI. For more insights, check out Stewart Alsop II’s Substack newsletter where he shares his perspective on tech’s most recent transformations.Check out...
2024-10-3138 min
Stewart SquaredEpisode #13: AI Hype vs. Reality: Cutting Through the NoiseWelcome to Stewart Squared podcast with the two Stewart Alsops! In this episode, we tackle the evolution and current state of artificial intelligence, with Stewart Alsop II critiquing the hype surrounding generative AI and questioning its tangible benefits to individuals, while Stewart Alsop III discusses how AI is becoming an effective tool for tasks like coding and research. Together, they reflect on how previous tech booms, like expert systems in the 80s and neural networks in the 90s, fizzled out, drawing comparisons to today’s AI landscape. For more insights, check out Stewart Alsop II’s article Still Haven't Seen...
2024-10-2448 min
Stewart SquaredEpisode #11: The Internet’s Genesis: How the 1990s Opened the Floodgates of InnovationWelcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, Stewart Alsop III and his father, Stewart Alsop II, take a deep dive into the early days of the internet, technology trends, and the nature of predictions with "skin in the game." Stewart Alsop II, who was at the forefront of tech journalism and venture capital, discusses pivotal moments like the rise of personal computing, early AI predictions, and the development of the Internet. His insights highlight the intersections of technology, business, and regulation.Check out this GPT we trained on the conversation!
2024-10-1038 min
Crazy WisdomEpisode #396: From Chaos to Crypto: How Argentina’s Turmoil is Fueling Global InnovationIn this episode of the Crazy Wisdom podcast, Stewart Alsop speaks with Diego Fernandez, co-creator of QuarkID and the Secretary of Innovation for Buenos Aires. They discuss the future of innovation in Buenos Aires, focusing on how technology can simplify citizen interactions with the government and empower individuals through control over their identity with Web3. The conversation explores the potential of decentralized technologies like blockchain to transform government services and create new opportunities for innovation, especially in Argentina's unique economic landscape. In the episode Stewart forgot the name of something about the innovation of digitizing real world...
2024-09-3052 min
Stewart SquaredEpisode #9: The AI Whisperer: A New Era of Prompt-Based ProgrammingWelcome to the Stewart Squared podcast with the two Stewart Alsops, featuring special guest Joe Alsop. This episode covers the evolution of technology from the rise of personal computing to the current advancements in artificial intelligence. The discussion touches on the challenges of early programming, the progression of software development, and the revolutionary shift toward natural language programming. Joe Alsop shares insights into simplifying programming for users and reflects on how AI is shaping the future of software and user interaction. Stay tuned for more engaging discussions on tech's past, present, and future.Check out this GPT...
2024-09-261h 07
Crazy WisdomEpisode #394: Can AI Actually Think? Exploring the Future of Intelligence and AutomationOn this episode of Crazy Wisdom, I, Stewart Alsop, sit down with Ben Ford and Michael Greenberg for a dynamic conversation. Ben is the founder of Mission Control Dev, and Michael is the founder of Third Brain, a company focused on automating business operations. We explore a variety of topics, including the real meaning of "artificial intelligence," how AI is impacting various industries, and whether we truly have AI today. Michael introduces his concept of "Third Brain," a digital layer of operations, while Ben reflects on his military background and how it shapes his current work. Both offer unique...
2024-09-2358 min
Crazy WisdomEpisode #392: From Digital Footprints to Transhumanism: Navigating the AI-Driven FutureIn this episode of the Crazy Wisdom podcast, Stewart Alsop speaks with Anand Dwivedi, a Senior Data Scientist at ICE, returning for his second appearance. The conversation covers a range of topics including the evolution of machine learning models, the integration of AI into operating systems, and how innovations like Neuralink may reshape our understanding of human-machine interaction. Anand also touches on the role of cultural feedback in shaping human learning, the implications of distributed systems in cybersecurity, and his current project—training a language model on the teachings of his spiritual guru. For more information, listeners can connect wi...
2024-09-1658 min
Stewart SquaredEpisode #7: Satellites, Warfare, and the End of Terrestrial TechWelcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore pivotal moments in technology, starting with the personal computing revolution, the evolution of smartphones, and how AI is shaping our future. Stewart Alsop II reflects on abandoning his "constellation of devices" theory after realizing, during a fishing trip in Iceland, that using multiple gadgets only complicates life. The discussion flows into AI, ecosystem control by companies like Apple, Google, and Samsung, and the future of tech integration, including the potential impact of satellite communications. Tune in for a thought-provoking conversation bridging past innovations with...
2024-09-1243 min
Stewart SquaredEpisode #6: Evernet Dreams: The Intersection of Satellite Tech, Battery Innovation, and Constant ConnectivityWelcome to Stewart Squared podcast with the two Stewart Alsops! In this episode, they dive into the history of personal computing, the evolution of the internet, and the development of mobile phone technology, all within the context of AI and the Evernet theory. They discuss the intriguing advancements in satellite technologies, like Starlink's portable internet solutions, and Apple's integration of satellite communication with the iPhone. They also explore the challenges and future of battery technology, touching on innovations like lithium-ion and magnesium batteries. The conversation moves into the commercialization of space, examining how these technologies might converge to shape...
2024-09-0545 min
Crazy WisdomEpisode #385: In Algorithms We Trust? The Power and Perils of AI in Our LivesIn this episode of the Crazy Wisdom podcast, Stewart Alsop chats with Taren Pang, a full-stack developer with a rich background in architecture, Web3, and AI. The discussion covers the evolving role of algorithms in shaping our online experiences, the importance of transparent AI and blockchain technologies, and how tools like Urbit and Bitcoin could reshape business in a decentralized world. Taren also shares insights on programming with AI and his journey of transitioning from architecture to the tech industry. For more on Taren's thoughts and work, stay tuned for future updates as he refines his focus....
2024-08-2353 min
Crazy WisdomEpisode #384: Beyond the Horizon: Exploring Consciousness and Reality with Erik NewtonIn this episode of the Crazy Wisdom Podcast, host Stewart Alsop welcomes back Erik Newton for a profound conversation on consciousness, personal growth, and the nature of reality. Together, they explore the challenges of expanding awareness, balancing intention with surrender, and the philosophical implications of emerging technologies like Neuralink. Erik shares his deep reflections on fatherhood, the complexities of human suffering, and the pursuit of peace in a chaotic world. For more insights from Erik, you can connect with him on Twitter at @NewtonLaw.Check out this GPT we trained on the conversation!Timestamps
2024-08-1954 min
Stewart SquaredEpisode #3: San Francisco: The Empire at Its Peak or on the Brink?Welcome to the Stewart Squared podcast with the two Stewart Alsops! In this episode, Stewart Alsop II and Stewart Alsop III discuss the complexities of San Francisco’s tech scene, the future of AI, and the evolution of tech infrastructure. They explore how San Francisco’s self-perception contrasts with a broader sense of national decline, draw parallels between historical empires and modern society, and debate the real impact of AI beyond the current hype. The conversation also touches on the concept of "federation of devices," the bubble-like behavior in the AI industry, and the influence of figures like Elon Musk...
2024-08-1541 min
Crazy WisdomEpisode #381: Why We Still Matter: Human Decision-Making in an AI-Driven FutureIn this episode of the Crazy Wisdom Podcast, Stewart Alsop speaks with Francisco D'Agostino, a business development expert focused on helping entrepreneurs expand into new markets. They discuss a range of topics, from the ethical implications of emerging technologies like AI to the historical parallels with figures like Oppenheimer, who grappled with the consequences of their creations. The conversation also touches on the human aspects of business development, cultural considerations in market expansion, and the potential future of AI in shaping societal structures. To learn more about Francisco and his work, you can follow him on Instagram at @Pancho...
2024-08-1240 min
Crazy WisdomEpisode #379: Tech, Tribes, and Transformation: Paul Spencer’s Patchwork AgeWelcome to the Crazy Wisdom Podcast! I’m your host, Stewart Alsop, and today’s guest is the insightful Paul Spencer of Zeitville Media. In this episode, we explore Paul’s thought-provoking ideas on the Patchwork Age, a concept he developed in 2020, which examines the breakdown of large cultural institutions and the reorganization of meaning on individual and micro-tribal levels. We discuss the interplay of technology, the influence of the 90s, and the emergence of hybridized cultural forms in the 2020s. Paul also shares his perspective on the role of puritanical thought in contemporary society and its impact on commun...
2024-08-051h 27
Crazy WisdomEpisode #378: The Connective Tissue of Innovation with Cody HergenroederIn this episode of the Crazy Wisdom podcast, host Stewart Alsop welcomes Cody Hergenroeder, a versatile creator deeply invested in product management. They explore the intricate relationships between symbolic systems and product management, discussing how these domains interconnect within the corporate environment. Cody shares insights on the role of connective tissue in organizations, the nature of memory and knowledge, and the evolving impact of artificial intelligence on society. This episode also touches on AI's role in modern note-taking and the broader implications for knowledge management. For more about Cody's work, visit his LinkedIn.Check out this GPT...
2024-08-0253 min
Crazy WisdomEpisode #377: Mapping the AI Mind: Beckett Dillon on Knowledge Graphs and BiomimicryStewart Alsop's guest on the Crazy Wisdom Podcast is Beckett Dillon, an AI innovator renowned for creating the Anima biomimicry and Nexus internal knowledge map LLM models and data sets. Their conversation covers a range of topics, including the intricacies of biomimicry, the concept and implementation of knowledge maps in AI, and the innovative experiments Beckett has conducted to enhance AI responses. Additionally, they touch on the ethical and practical implications of AI development and the importance of open-source contributions in the field. For more insights, you can connect with Beckett through his Linkedin page.Check out t...
2024-07-291h 00
Stewart SquaredConferences: Why do people start them?In this episode of Crazy Wisdom's special series, Stewart Squared, Stewart Alsop III and his father Stewart Alsop II delve into various topics. They discuss the fragmented theme of AI, AI wearables, and technology conferences, including anecdotes and the purpose behind such events. They explore the evolution of tech products, mentioning companies like Apple and Google and their approaches to product development and market fit. Additionally, they touch on personal experiences with notable tech figures like Steve Wozniak and Steve Jobs, along with insights on organizing and running successful tech conferences. The discussion also covers the intersection of technology...
2024-07-1344 min
Crazy WisdomCrowdsourced Innovation: How Nick Burns Navigates Product DevelopmentIn this episode of Crazy Wisdom, Stewart Alsop hosts Nick Berns, founder of a software product company and a marketing firm focusing on SEO. They discuss a range of topics, including the intricacies of couch surfing while working remotely, the evolution of Airbnb, and Nick's journey in product development and AI-driven SEO. They also explore the challenges of marketing for developers and introverts, with Nick sharing insights into his productivity hacks and strategies for finding product-market fit. For more information about Nick's work, visit his portfolio at fryingneurons.com, follow him on Twitter at fryingneurons, or check out his...
2024-07-0843 min
Crazy WisdomFrom Federalism to Cryptoeconomics: Modern Trust MechanismsIn this episode of the Crazy Wisdom Podcast, host Stewart Alsop sits down with Stuart Christoph, CEO of Tocwex Syndicate, to discuss the evolving landscape of trust in digital economies. They explore the intricacies of the Tocwex Syndicate and FUND, focusing on the concept of trust versus trustlessness in blockchain systems, the role of trusted identities and oracles in urban ecosystems, and the separation of infrastructure and institutions. They also touch on the implications of federalism in the U.S. and the future of dispute resolution in a global, digital context. For more information, visit tocwexsyndicate.com and follow...
2024-07-051h 02
Crazy WisdomDecentralized Media and the Evolution of Cultural ValuesIn this episode of the Crazy Wisdom podcast, your host Stewart Alsop is joined by Raffi Grinberg, Executive Director at Dialog. They explore a range of topics including the essence of dialogue, consciousness in robots, human progress, and the ethics of monotheism versus paganism. Raffi shares insights on the cultural significance of the divine mother, the impact of social media on society, and the potential future of decentralized media. They also discuss the idea of a fourth branch of government to manage digital space, the challenges of large-scale bureaucracies, and innovative approaches to maintaining company agility. For more about...
2024-07-0153 min
Crazy WisdomNavigating the Digital Revolution with Steve CaseWelcome to the Crazy Wisdom Podcast! I'm your host, Stewart Alsop III, and today we have a special guest, Steve Case, the former CEO of AOL and current chairman of Revolution. In this episode, we cover a wide range of topics, including Steve's early career and the founding of AOL, the challenges faced during the dot-com era, and the importance of partnerships in driving success. We also discuss Steve's transition into venture capital, his work with the Rise of the Rest initiative, and the regulatory challenges faced by tech companies. Read Steve's profile in Revolution's web page here for...
2024-06-2857 min
Crazy WisdomAI at Your Service: Revolutionizing Tasks with Omar ShayaIn this episode of the Crazy Wisdom Podcast, Stewart Alsop interviews Omar Shaya, the founder of Multion. They explore the transformative potential of AI in everyday tasks, discussing how Multion acts as an AI agent to perform web-based activities like booking flights and making reservations. The conversation also covers the evolution of AI models, the future of programming, and the integration of AI in coding. For more information, you can visit Multion's website at Multion.ai and follow them on Twitter at @Multion_ai. Check out this GPT we trained on the conversation! Timestamps
2024-06-2153 min
Crazy WisdomCrypto, AI, and the New Age of Wisdom with David WeinsteinIn this episode of the Crazy Wisdom podcast, Stewart Alsop hosts David Weinstein, former Chief of Staff at the Near Foundation. They cover a range of topics including the Near Protocol and its scalability, the intersection of AI and crypto, the importance of propositional truth, and the future of learning with AI. David shares insights on the limitations of technology in solving existential problems and explores ideas for a new kind of Wisdom School that focuses on holistic education and collective intelligence. Find out more about David Weinstein on Twitter at @DW_Stein and his Substack at davidweinstein.substack...
2024-06-1458 min
Crazy WisdomNavigating AI's Impact on Society: Insights with Ekue KpodarIn this episode of the Crazy Wisdom Podcast, host Stewart Alsop speaks with Ekue Kpodar about a range of topics, including knowledge management systems, AI's role in employee training, and the potential of combining large language models with knowledge graphs. They explore the concept of value aggregation in social media, the relationship between data science and follower growth, and the implications of AI in augmenting human capabilities. The conversation also touches on the future of AI agents, energy consumption in AI advancements, and the geopolitical impacts of energy policies. Additionally, they discuss Argentina's economic situation, Bitcoin's role in unstable...
2024-06-0756 min
Crazy WisdomAlgorithms in the Air: Vladimir Osipov on AI's Role in Language Learning and AviationIn this episode of the Crazy Wisdom Podcast, host Stewart Alsop chats with Vladimir Osipov, co-founder of Lingolette, about his journey from hobbyist to professional software developer, his various interests from airsoft to flying small planes, and the impact of AI on software development. They explore the nuances of solid-state physics, language learning through immersion, and the innovative features of Lingolette that leverage AI to create personalized learning experiences. Tune in to hear Vladimir's insights on using AI to stay competitive, the importance of adaptive content in language learning, and more. Check out Lingolette here and connect with Vladimir...
2024-05-3154 min
Crazy WisdomSynthetic Data and AI's Future: Insights from Alchemy.ai's John BallentineIn this episode of the Crazy Wisdom Podcast, Stewart Alsop talks with John Ballentine, the founder and CEO of Alchemy.ai. With over seven years of experience in machine learning and large language models (LLMs), John shares insights on synthetic data, the evolution of AI from Google's BERT model to OpenAI's GPT-3, and the future of multimodal algorithms. They discuss the significance of synthetic data in reducing costs and energy for training models, the challenges of creating models that understand natural language, and the exciting potential of AI in various fields, including cybersecurity and creative arts. For more information...
2024-05-2451 min
Crazy WisdomBeyond the Black Box: Exploring the Human Side of AI with Lachlan PhillipsIn this episode of the Crazy Wisdom Podcast, host Stewart Alsop welcomes Lachlan Phillips, founder of LiveMind AI, for a compelling conversation about the implications of decentralized AI. They discuss the differences between centralized and decentralized systems, the historical context of centralization, and the potential risks and benefits of distributed computing and storage. Topics also include the challenges of aligning AI with human values, the role of supervised fine-tuning, and the importance of trust and responsibility in AI systems. Tune in to hear how decentralized AI could transform technology and society. Check out LiveMind AI and follow Lachlan on...
2024-05-2155 min
Crazy WisdomNavigating Probabilistic Realities: Principles, Sheet Metal, and AI Reflections with Aaron LowryIn this episode of the Crazy Wisdom podcast, host Stewart Alsop sits down with Aaron Lowry, an experienced consultant and returning guest. They discuss a wide range of topics, including Lowry's work in rebuilding custom vehicles, the value of blending aesthetics with engineering, and the challenges of balancing principles and propositions in problem-solving. They also explore the evolving world of artificial intelligence, contrasting its limitations with human intelligence, and consider its impact on creative expression. Connect with Aaron on Twitter at @Aaron_Lowry for more insights into his projects and ideas. Check out this GPT we trained...
2024-05-0658 min
Crazy WisdomAI and the Art of The Possible: A Dialogue with Albert ChunIn this episode of the Crazy Wisdom podcast, I, Stewart Alsop, had the pleasure of hosting Albert Chun, Director of Operations at Invisible Technologies. We explored the latest advancements in large language models, particularly focusing on their implications for content creation, coding, and video generation. Albert provided insights into the evolution of software engineering towards prompt engineering, the philosophical debates surrounding AI and humanity, and the impact of AI on creativity and discipline. We also discussed the role of AI in education across different socioeconomic contexts and pondered over the future of AI in decentralized systems. Albert shared some...
2024-04-2243 min
Crazy WisdomSilicon Dreams: Rob Glaser’s Impact on the rise of personal computingWelcome to the Crazy Wisdom podcast, where we explore the interplay of technology, society, and the mind. In this special "Stewart Squared" series, we dive into the stories and insights of pioneers who have shaped the digital world. Today, we're thrilled to feature Rob Glaser, founder and CEO of Real Networks, a trailblazer in the realm of streaming media. Join us as Stewart Alsop III and his father, Stewart Alsop II, delve into Glaser’s fascinating journey from his early days at Microsoft, revolutionizing the world of software with Microsoft Word, to launching Real Networks and navigating the tumultuous wa...
2024-04-0855 min
Crazy WisdomDigital Dollars and Cowboy Values: The Wyoming Stable Token StoryIn this episode of the Crazy Wisdom Podcast, Stewart Alsop sits down with David Pope, CPA, CGMA, and Commissioner of the Wyoming Stable Token Commission. They delve into the innovative financial landscape of Wyoming, particularly focusing on the development and implications of stable tokens. The conversation covers the legislative journey, economic strategies, and the broader vision of integrating digital assets into Wyoming’s financial ecosystem. Additionally, they explore philosophical aspects of leadership, partnership dynamics, and the profound connection between humans and animals, drawing parallels between management theories and equine psychology. Timestamps 00:05:00 - Discussion on the use an...
2024-04-0149 min
Crazy WisdomFrom Silicon Dreams to AI Realities: Navigating Tech's Next FrontierThe podcast episode features a conversation between Stewart Alsop III and his father, Stewart Alsop II, and their guest, Joe Schoendorf from Accel, a prominent venture capital firm. Joe shares his insights on the transition from the early PC computing industry to the rise of the internet and eventually to the AI revolution. They discuss factors like the creation of the cloud, AI, and other technological tools that have greatly accelerated the speed of innovation. The podcast also covers the history of Silicon Valley, the evolution of venture capital, and the roles of today's young CEOs in tech startups...
2024-03-0447 min
Crazy WisdomIdentity in the Age of Artificial Intelligence: A Journey WithinIn this episode of the Crazy Wisdom Podcast, Stewart Alsop is joined by Jack Thomas. Jack shares his transitions from nuclear engineering to philosophy and now machine learning, revealing his approach to learning and understanding complex concepts. They explore existential risks and the advantages and challenges of AI, the importance of understanding the mathematics behind machine learning, and the future of programming. Jack also shares his views on the positive and negative impacts of disruptive technologies, and the significance of adhering to ethics and morality when innovating. Check out this GPT we trained on the conversation Timestamps
2024-03-011h 02
Crazy WisdomFrom Early Apple to AI: Donna Dubinsky's Tech OdysseyThis is a new series of Crazy Wisdom where I invited my dad Stewart Alsop II to bring people from his past as a tech journalist and uncover the best stories from the 1980s, 90s and early 2000s about the personal computing revolution and apply them to the AI revolution currently happening. Our first guest Donna Dubinsky talks about her career experiences at Apple, handheld innovator Handspring, her work as the CEO of Palm (of the Palm Pilot handheld mobile device), and current AI work at Numenta. She and Stewart Alsop II both go deep on how...
2024-01-291h 13
Crazy WisdomChristianity in the Era of AI: Insights from Matthew BoschIn this episode of the Crazy Wisdom Podcast, Stewart Alsop explores various complex topics such as artificial intelligence (AI), the Christian faith and the potential impacts each one can have on modern society. Matthew Bosch shares his personal journey of converting to Christianity in adulthood, as well as his perspective on the intersection of religion and AI. He points out the potential dangers involved with AI, specifically regarding the human tendency for 'God Complex', and agrees with the host in asserting the necessity of a spiritual or higher power to help people navigate life's complexities. Both the Stewart and...
2024-01-0243 min
Crazy WisdomWhat It's Really Like Being a VC (feat. Stewart Alsop II)In this episode I sit down with my father Stewart Alsop II to talk about being a journalist, being a VC, his favorite investments, and how he thinks about stress and anxiety.
2018-12-0358 min