Scaling Intimacy with AI

Welcome to episode #1008 of Thinking With Mitch Joel (formerly Six Pixels of Separation).

What if artificial intelligence didn't just build faster startups... but redefined what it means to be an entrepreneur? Henrik Werdelin has been exploring that question for years. As the co-founder of Bark (the company behind BarkBox and the new Bark Air) and Prehype (the startup studio that helped launch ventures like AndCo, Ro, and ManagedByQ), Henrik (who also has a great podcast called, Beyond The Prompt) has spent his career creating businesses that live at the intersection of creativity, community and technology. Now, with his new book Me, My Customer And AI, he's rethinking entrepreneurship for a world where anyone can start a business, but few will build one that truly matters. In this conversation, we explore how AI is changing human behavior, the paradox of accessibility and saturation, and why "interestingness" may be the new metric of success. Henrik explains why the future of entrepreneurship isn't about scale, it's about intimacy, authenticity and knowing your customer better than anyone else. We also discuss his latest venture, Audos, a platform designed to help aspiring entrepreneurs build companies using AI agents, and how this movement could usher in a new "neighborhood economy" where small, deeply connected businesses thrive. From reflections on the early internet to insights about the next wave of AI-driven startups, Henrik's ideas are both practical and profoundly human, reminding us that even in an algorithmic age, it's our relationships, our curiosity and our resilience that will define what's next. Enjoy the conversation...

• Running time: 1:02:18.
• Hello from beautiful Montreal.
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• Here is my conversation with Henrik Werdelin.
• Me, My Customer And AI.
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Chapters:

(00:00) - Introduction to Entrepreneurship and AI. (02:10) - Understanding AI's Impact on Human Behavior. (06:42) - The Evolution of AI Tools and Their Implications. (11:54) - Navigating the Future: Utopia vs. Dystopia. (18:46) - The Changing Landscape of Entrepreneurship. (24:20) - The Role of AI in Business Creation. (30:40) - Radical Humanness in the Age of AI. (37:30) - The Future of Capitalism and Entrepreneurship. (46:33) - The Unbundling of SaaS and Content Creation. (55:43) - Pursuing Interestingness in Entrepreneurship.