
Crazy Wisdom
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.
Latest episodes

Mar 10, 2025 • 59min
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 funds analyzing parking lots to wildfire response efforts. Check out more about Gabe and Umbra at umbraspace.com (https://umbraspace.com), and don’t miss their open data archive for high-resolution satellite imagery.Check out this GPT we trained on the conversation!Timestamps00:00 Introduction to the Crazy Wisdom Podcast00:05 Gabe's Background and Umbra's Mission00:34 The Story Behind 'Come and Take It'01:32 Space Technology and Cost Plus Contracts03:28 The Impact of Elon Musk and SpaceX05:16 Umbra's Business Model and Profitability07:28 Challenges in the Satellite Business11:45 Investors and Funding Journey19:31 Space Business Landscape and Future Prospects23:09 Defense and Regulatory Challenges in Space31:06 Practical Applications of Satellite Data33:16 Unexpected Wealth and Autistic Curiosity33:49 Beet Farming and Data Insights35:09 Philosophy in Business Strategy38:56 Empathy and Investor Relations43:00 Raising Capital: Strategies and Challenges44:56 The Sovereignty Game vs. Venture Game51:12 Concluding Thoughts and Contact Information52:57 The Treasure Hunt and AI DependenciesKey InsightsThe Shift from Cost-Plus to Cost-Minus in Government Contracting – Historically, aerospace and defense contracts operated under a cost-plus model, where companies were reimbursed for expenses with a guaranteed profit. Gabe explains how the shift toward cost-minus (firm-fixed pricing) is driving efficiency and competition in the industry, much like how SpaceX drastically reduced launch costs by offering services instead of relying on bloated government contracts.Satellite Imagery Has Become a Crucial Tool for Businesses – Beyond traditional defense and intelligence applications, high-resolution satellite imagery is now a critical asset for hedge funds, investors, and commercial enterprises. Gabe describes how firms use satellite data to analyze parking lots, monitor supply chains, and even track cryptocurrency mining activity based on power line sagging and cooling fan usage on data centers.Space Technology is More Business-Driven Than Space-Driven – While many assume space startups are driven by a passion for exploration, Umbra’s success is rooted in strong business fundamentals. Gabe emphasizes that their focus is on unit economics, supply-demand balance, and creating a profitable company rather than simply innovating for the sake of technology.China’s Growing Presence in Space and Regulatory Challenges – Gabe raises concerns about China’s aggressive approach to space, noting that they often ignore international agreements and regulations. Meanwhile, American companies face significant bureaucratic hurdles, sometimes spending millions just to navigate licensing and compliance. He argues that unleashing American innovation by reducing regulatory friction is essential to maintaining leadership in the space industry.Profitability is the Ultimate Measure of Success – Unlike many venture-backed space startups that focus on hype, Umbra has prioritized profitability, making it one of the few successful Earth observation companies. Gabe contrasts this with competitors who raised massive sums, spent excessively, and ultimately failed because they weren’t built on sustainable business models.Satellite Technology is Revolutionizing Disaster Response – One of the most impactful uses of Umbra’s satellite imagery has been in wildfire response. By capturing images through smoke and clouds, their data was instrumental in mapping wildfires in Los Angeles. They even made this data freely available, helping emergency responders and news organizations better understand the crisis.Philosophy and Business Strategy Go Hand in Hand – Gabe highlights how strategic thinking and philosophical principles guide decision-making in business. Whether it’s understanding investor motivations, handling conflicts with empathy, or ensuring a company can sustain itself for decades rather than chasing short-term wins, having a strong philosophical foundation is key to long-term success.

Mar 7, 2025 • 38min
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-person experiences. For more on Andrew, check out his LinkedIn and Instagram.Check out this GPT we trained on the conversation!Timestamps00:00 Introduction and Guest Welcome00:27 Meeting in LA and Local Insights01:34 The Creative Process and Technology03:47 Balancing Solitude and Connectivity07:21 AI's Role in Creativity and Productivity11:00 Future of AI in Creative Industries14:39 Challenges and Opportunities with AI16:59 AI in Hollywood and Ethical Considerations18:54 Silicon Valley and AI's Impact on Jobs19:31 Navigating the Future with AI20:06 Adapting to Rapid Technological Change20:49 The Value of Art in a Fast-Paced World21:36 Shifting Aesthetics and Cultural Perception22:54 The Human Connection in the Age of AI24:37 Resurgence of Traditional Art Forms27:30 The Importance of Early Artistic Education31:07 The Role of Poetry and Language35:56 Balancing Technology and Intention37:00 Conclusion and Contact InformationKey InsightsThe Importance of Solitude in Creativity – Andrew Burlinson emphasizes that creativity thrives in moments of boredom and solitude, which have become increasingly rare in the digital age. He reflects on his childhood, where a lack of constant stimulation led him to develop his artistic skills. Today, with infinite digital distractions, people must intentionally carve out space to be alone with their thoughts to create work that carries deep personal intention rather than just remixing external influences.The Struggle to Defend Attention – Stewart and Andrew discuss how modern digital platforms, particularly social media, are designed to hijack human attention through powerful AI-driven engagement loops. These mechanisms prioritize negative emotions and instant gratification, making it increasingly difficult for individuals to focus on deep, meaningful work. They suggest that future AI advancements could paradoxically help free people from screens, allowing them to engage with technology in a more intentional and productive way.AI as a Creative Partner—But Not Yet a True Challenger – While AI is already being used in creative fields, such as Hollywood’s subtle use of AI for film corrections, it currently lacks the ability to provide meaningful pushback or true creative debate. Andrew argues that the best creative partners challenge ideas rather than just assist with execution, and AI’s tendency to be agreeable and non-confrontational makes it a less valuable collaborator for artists who need critical feedback to refine their work.The Pendulum Swing of Human and Technological Aesthetics – Throughout history, every major technological advancement in the arts has been met with a counter-movement embracing raw, organic expression. Just as the rise of synthesizers in music led to a renewed interest in acoustic and folk styles, the rapid expansion of AI-generated art may inspire a resurgence of appreciation for handcrafted, deeply personal artistic works. The human yearning for tactile, real-world experiences will likely grow in response to AI’s increasing role in creative production.The Enduring Value of Art Beyond Economic Utility – In a world increasingly shaped by economic efficiency and optimization, Andrew stresses the need to reaffirm the intrinsic value of art. While capitalism dominates, the real significance of artistic expression lies in its ability to move people, create connection, and offer meaning beyond financial metrics. This perspective is especially crucial in an era where AI-generated content is flooding the creative landscape, potentially diluting the sense of personal expression that defines human art.The Need for Intentionality in Using AI – AI’s potential to streamline work processes and enhance creative output depends on how humans choose to engage with it. Stewart notes that while AI can be a powerful tool for structuring time and filtering distractions, it can also easily pull people into mindless consumption. The challenge lies in using AI with clear intention—leveraging it to automate mundane tasks while preserving the uniquely human aspects of ideation, storytelling, and artistic vision.The Role of Poetry and Language in Reclaiming Humanity – In a technology-driven world where efficiency is prioritized over depth, poetry serves as a reminder of the human experience. Andrew highlights the power of poets and clowns—figures often dismissed as impractical—as essential in preserving creativity, playfulness, and emotional depth. He suggests that valuing poetry and artistic language can help counterbalance the growing mechanization of culture, keeping human expression at the forefront of civilization’s evolution.

Mar 3, 2025 • 58min
Episode #440: AI Agents, Code Wizards, and What Could Possibly Go Wrong?
In this engaging discussion, Nick Ludwig, creator of Kibitz and lead developer at Hyperware, shares insights on the evolution of AI in coding. He explores how AI-powered agents are revolutionizing software development by managing workflows autonomously. The conversation delves into security challenges, particularly with file systems and prompt vulnerabilities. Nick emphasizes the importance of containerization for safeguarding AI agents, especially in financial transactions, while highlighting the transformative potential of natural language coding in the future.

Mar 2, 2025 • 1h 1min
Episode #439: Beyond Second Brains: What AI Is Actually Doing to Knowledg
In this engaging conversation, Andrew Altschuler, a researcher and educator from Tana, Inc., delves into the complexities of knowledge systems and AI's role in reshaping how we manage information. He discusses the implications of network effects in social media and the rise of digital warlords, exploring resilience against information warfare. Altschuler further distinguishes between secular knowledge and deeper existential understanding, while emphasizing the need for personalized approaches in knowledge management. Tune in for insights on cognition, creativity, and the future of AI in knowledge systems!

Feb 24, 2025 • 55min
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 the mythology needed to make sense of our accelerating world. You can find more of Ivan’s work at nothinghuman.substack.com or follow him on Twitter at @IvanVendrov.Check out this GPT we trained on the conversation!Timestamps00:00 Introduction and Setting00:21 The Bitter Lesson in AI02:03 Challenges in AI Data and Infrastructure04:03 The Role of User Experience in AI Adoption08:47 Evaluating Intelligence and Divergent Thinking10:09 The Future of AI and Society18:01 The Role of Big Tech in AI Development24:59 Humanism and the Future of Intelligence29:27 Exploring Kafka and Tolkien's Relevance29:50 Tolkien's Insights on Machine Intelligence30:06 Samuel Butler and Machine Sovereignty31:03 Historical Fascism and Machine Intelligence31:44 The Future of AI and Biotech32:56 Voice as the Ultimate Human-Computer Interface36:39 Social Interfaces and Language Models39:53 Javier Malay and Political Shifts in Argentina50:16 The State of Society in the U.S.52:10 Concluding Thoughts on Future ProspectsKey InsightsThe Bitter Lesson Still Holds, but AI Faces Bottlenecks – Ivan Vendrov reinforces Rich Sutton’s "bitter lesson" that AI progress is primarily driven by scaling compute and data rather than human-designed structures. While this principle still applies, AI progress has slowed due to bottlenecks in high-quality language data and GPU availability. This suggests that while AI remains on an exponential trajectory, the next major leaps may come from new forms of data, such as video and images, or advancements in hardware infrastructure.The Future of AI Is Centralization and Fragmentation at the Same Time – The conversation highlights how AI development is pulling in two opposing directions. On one hand, large-scale AI models require immense computational resources and vast amounts of data, leading to greater centralization in the hands of Big Tech and governments. On the other hand, open-source AI, encryption, and decentralized computing are creating new opportunities for individuals and small communities to harness AI for their own purposes. The long-term outcome is likely to be a complex blend of both centralized and decentralized AI ecosystems.User Interfaces Are a Major Limiting Factor for AI Adoption – Despite the power of AI models like GPT-4, their real-world impact is constrained by poor user experience and integration. Vendrov suggests that AI has created a "UX overhang," where the intelligence exists but is not yet effectively integrated into daily workflows. Historically, technological revolutions take time to diffuse, as seen with the dot-com boom, and the current AI moment may be similar—where the intelligence exists but society has yet to adapt to using it effectively.Machine Intelligence Will Radically Reshape Cities and Social Structures – Vendrov speculates that the future will see the rise of highly concentrated AI-powered hubs—akin to "mile by mile by mile" cubes of data centers—where the majority of economic activity and decision-making takes place. This could create a stark divide between AI-driven cities and rural or off-grid communities that choose to opt out. He draws a parallel to Robin Hanson’s Age of Em and suggests that those who best serve AI systems will hold power, while others may be marginalized or reduced to mere spectators in an AI-driven world.The Enlightenment’s Individualism Is Being Challenged by AI and Collective Intelligence – The discussion touches on how Western civilization’s emphasis on the individual may no longer align with the realities of intelligence and decision-making in an AI-driven era. Vendrov argues that intelligence is inherently collective—what matters is not individual brilliance but the ability to recognize and leverage diverse perspectives. This contradicts the traditional idea of intelligence as a singular, personal trait and suggests a need for new frameworks that incorporate AI into human networks in more effective ways.Javier Milei’s Libertarian Populism Reflects a Global Trend Toward Radical Experimentation – The rise of Argentina’s President Javier Milei exemplifies how economic desperation can drive societies toward bold, unconventional leaders. Vendrov and Alsop discuss how Milei’s appeal comes not just from his radical libertarianism but also from his blunt honesty and willingness to challenge entrenched power structures. His movement, however, raises deeper questions about whether libertarianism alone can provide a stable social foundation, or if voluntary cooperation and civil society must be explicitly cultivated to prevent libertarian ideals from collapsing into chaos.AI, Mythology, and the Need for New Narratives – The conversation closes with a reflection on the power of mythology in shaping human understanding of technological change. Vendrov suggests that as AI reshapes the world, new myths will be needed to make sense of it—perhaps similar to Tolkien’s elves fading as the age of men begins. He sees AI as part of an inevitable progression, where human intelligence gives way to something greater, but argues that this transition must be handled with care. The stories we tell about AI will shape whether we resist, collaborate, or simply fade into irrelevance in the face of machine intelligence.

Feb 21, 2025 • 37min
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 scaling businesses, and insights into the intersection of technology and human behavior. For more on Jason’s work, visit his site at SureDone.com or connect with him on Linkedin.Check out this GPT we trained on the conversation!Timestamps00:00 Introduction to the Crazy Wisdom Podcast00:13 Jason Nadaf's Vision for Sure Done01:31 The Evolution of E-commerce03:06 Building Multi-Channel Solutions07:00 Challenges in E-commerce Automation11:05 The Role of AI in E-commerce13:51 Accelerationism and Capitalism18:36 The Myth of 'Build It and They Will Come'19:01 Learning from Failed Playbooks19:58 The Role of Bureaucracy and Incentives20:57 Humanistic Energy and Potential25:14 Exploring Neurodivergence and Normies28:53 The Future of Simulation and Modeling31:12 Balancing Stress and Happiness33:42 Final Thoughts on E-commerce and Human DesireKey InsightsThe Future of E-Commerce Lies in Automation and AI – Jason Nadaf discusses how automation has already transformed e-commerce by reducing manual work, streamlining listings, and optimizing multi-channel selling. AI is the next frontier, enabling sellers to create more compelling product descriptions, analyze customer behavior, and predict trends. However, AI still struggles with generating accurate product data from raw materials, requiring human oversight.Big Tech Often Miscalculates Market Adoption – Large corporations tend to assume that building a new platform or marketplace automatically attracts users. Jason shares how two of the world’s biggest tech companies underestimated the effort required to onboard sellers and drive traction, leading to delays in adoption. Success in e-commerce requires a deep understanding of seller needs, rather than relying solely on brand recognition or market dominance.Capitalism is Not as Efficient as It Could Be – While capitalism drives innovation, Jason argues that it often misallocates resources. Talent and potential don’t always correlate with opportunity, meaning that some of the most innovative minds never get the funding or support they need. Bureaucracy within large corporations further slows down decision-making and stifles innovation.Diversification is Essential for Long-Term Success – Many sellers rely too heavily on a single platform, such as Amazon, without realizing how vulnerable they are to policy changes or algorithm updates. Jason emphasizes the importance of spreading risk across multiple marketplaces, search engines, and social platforms to ensure resilience against sudden disruptions.The Acceleration of Technology Will Reshape Commerce – The concept of accelerationism, which suggests that technological progress is rapidly compounding, is particularly relevant to e-commerce. AI, automation, and digital tools are evolving faster than ever, potentially leading to a future where single-person companies can rival large enterprises in efficiency and revenue.Human Intent in Commerce is Complex and Non-Uniform – A major takeaway from Jason’s experience in e-commerce is that consumer intent varies widely across cultures, platforms, and product categories. A successful sales strategy on Amazon might not work on Instagram or TikTok. Understanding these nuances is key to crafting effective product listings, advertisements, and pricing models.Stress and Uncertainty Are Inevitable, But Perspective Matters – As the digital landscape evolves unpredictably, many entrepreneurs and professionals experience stress about the future. Jason suggests that while predicting the future is nearly impossible, adaptability and maintaining a clear perspective can help individuals and businesses thrive. Rather than being paralyzed by uncertainty, focusing on actionable strategies and innovation is the best way forward.

Feb 17, 2025 • 53min
Episode #436: How AI Will Reshape Power, Governance, and What It Means to Be Human
Roko Mijic, an AI ethics and alignment researcher, joins the conversation to discuss how artificial intelligence will reshape society and governance. He highlights the risks of centralized power and proposes decentralized AI as an alternative. Roko critiques space colonization and suggests that oceans might offer a better frontier for humanity. The discussion also touches on AI's role in network states, the resurgence of industrialization, and the potential of nuclear energy in a new world order, urging proactive engagement with these transformative changes.

Feb 14, 2025 • 59min
Episode #435: How AI, Drones, and Rare Earths Will Decide the Next Global Conflict
Troy Johnson, founder of Resource Development Group, delves into the transformative role of mining in global geopolitics. He highlights the strategic significance of rare earth elements like gallium and germanium in modern warfare, particularly in drone technology. The conversation also tackles the U.S.-China rivalry over resource dominance, and how AI is reshaping military strategies. Additionally, they discuss the shift from traditional media to podcasts as trusted sources of information and the evolving dynamics of corporate accountability in the mining industry.

Feb 10, 2025 • 1h 2min
Episode #434: From the Age of Answers to the Age of Questions
Dimetri Kofinas, host of Hidden Forces, dives deep into the shift from an 'age of answers' to an 'age of questions.' He unpacks how AI influences human cognition and decision-making, raising concerns about autonomy. The conversation touches on the evolution of media and its role in shaping societal narratives, especially in light of trauma's destabilizing effects. Kofinas also explores the philosophical complexities of consciousness and the challenges of discerning truth in a media-saturated world.

Feb 7, 2025 • 54min
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 more on Brendon’s work, check out unize.org and his articles at web10.ai.Check out this GPT we trained on the conversation!Timestamps00:00 Introduction to the Crazy Wisdom Podcast00:35 Exploring Unise: A Knowledge Management App01:01 The Evolution of Knowledge Management02:32 Personal Knowledge Management Trends03:10 Object-Oriented Knowledge Management05:27 The Future of Knowledge Graphs and AI10:37 Challenges in Simulating the Human Mind22:04 Knowledge Management in Organizations26:57 The Role of Autonomous Agents30:00 Personal Experiences with Sleep Aids30:07 Unique Human Perceptions32:08 Knowledge Management Journey33:31 Personal Knowledge Management Systems34:36 Challenges in Knowledge Management35:26 Future of Knowledge Management with AI36:29 Melatonin and Sleep Patterns37:30 AI and the Future of the Internet43:39 Reasoning and AI Limitations48:33 The Future of AI and Human Reasoning52:43 Conclusion and Contact InformationKey InsightsThe Evolution of Knowledge Management: Brendon Wong highlights how knowledge management has evolved from personal note-taking systems to sophisticated, object-oriented models. He emphasizes the shift from traditional page-based structures, like those in Roam Research and Notion, to systems that treat information as interconnected objects with defined types and properties, enhancing both personal and organizational knowledge workflows.The Future Lies in Object-Oriented Knowledge Systems: Brendon introduces the concept of object-oriented knowledge management, where data is organized as distinct objects (e.g., books, restaurants, ideas) with specific attributes and relationships. This approach enables more dynamic organization, easier data retrieval, and better contextual understanding, setting the stage for future advancements in knowledge-based applications.AI and Knowledge Graphs Are a Powerful Combination: Brendon discusses the synergy between AI and knowledge graphs, explaining how AI can generate, maintain, and interact with complex knowledge structures. This integration enhances memory, reasoning, and information retrieval capabilities, allowing AI systems to support more nuanced and context-aware decision-making processes.The Limitations of Current AI Models: While AI models like LLMs have impressive capabilities, Brendon points out their limitations, particularly in reasoning and long-term memory. He notes that current models excel at pattern recognition but struggle with higher-level reasoning tasks, often producing hallucinations when faced with unfamiliar or niche topics.Challenges in Organizational Knowledge Management: Brendon and Stewart discuss the persistent challenges of implementing knowledge management in organizations. Despite its critical role, knowledge management is often underappreciated and the first to be cut during budget reductions. The conversation highlights the need for systems that are both intuitive and capable of reducing the manual burden on users.The Potential and Pitfalls of Autonomous Agents: The episode explores the growing interest in autonomous and semi-autonomous agents powered by AI. While these agents can perform tasks with minimal human intervention, Brendon notes that the technology is still in its infancy, with limited real-world applications and significant room for improvement, particularly in reliability and task generalization.Reimagining the Future of the Internet with Web 10: Brendon shares his vision for Web 10, an ambitious rethinking of the internet where knowledge is better structured, verified, and interconnected. This future internet would address current issues like misinformation and data fragmentation, creating a more reliable and meaningful digital ecosystem powered by AI-driven knowledge graphs.
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