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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this compelling episode of AI & I, Dan Shipper interviews Henrik Werdelin, co-founder of Prehype and BarkBox, about the emerging concept of "portfolio entrepreneurship" and how AI is democratizing business creation. The conversation explores Henrik's ambitious goal to launch a million businesses that each generate $1M in revenue through his new platform, Audos. (05:30)
Henrik is the co-founder of startup studio Prehype, which helped launch BarkBox (now public) and Ro Health. He's currently co-founding Audos, a platform designed to help millions become entrepreneurs using AI. Henrik is also the author of "Me, My Customer, and AI" and hosts the podcast "Beyond the Prompt" with Stanford professor Jeremy Ottley.
Dan is the founder of Every, a media company and startup studio that emerged from Prehype. He's known for his work in media entrepreneurship and his writing about AI and business strategy. Dan hosts the AI & I podcast and has been exploring portfolio entrepreneurship through Every's various products and services.
Henrik emphasizes that successful entrepreneurship begins with identifying who you want to serve for the next ten years, not what product you want to build. (17:42) As he puts it: "You can't start with an idea. You can't start with a technology. You can't start with a market size. You have to start with who do you want to serve for the next ten years and what is a fundamental problem that they have that you feel that you can solve." This approach allows entrepreneurs to build multiple solutions for the same customer base, creating what he calls "relationship capital" - a sustainable competitive advantage in an AI-driven world.
Dan adds a crucial insight to Henrik's customer-first approach: instead of trying to figure out who your customer is, focus on understanding who you are. (19:39) This self-discovery process involves building things, putting them out in the world, and iterating based on what resonates with you personally. Dan shares how it took him three years to admit he really wanted to be a writer, which then informed how he structured Every. This authentic self-knowledge creates natural customer-founder fit and sustainable business models.
Henrik introduces the concept of "relationship capital" as potentially the only remaining moat in an AI age where everyone can build anything. (16:27) This capital has three dimensions: depth (how much customers feel seen by you), density (how much they feel you belong in their community), and durability (whether you have permission to offer more than your initial product). Companies like Nike have strong durability - you can imagine a Nike hotel - while others like Hilton don't - it's hard to imagine Hilton shoes. This framework helps entrepreneurs build lasting businesses that can expand naturally.
Henrik predicts that successful entrepreneurs won't build single-agent businesses but will serve customers through portfolios of AI agents. (13:58) He explains: "A founder will serve a customer, and then they will have multiple agents that will have to be part of this portfolio of tools that they offer to their customers." This approach allows entrepreneurs to solve multiple problems for the same customer base, compounding their relationship capital and creating more valuable, sticky business ecosystems.
Henrik shares his "micro-moments" framework for career decision-making - identifying 30 concrete, specific activities that put you in flow and make you happy. (31:43) These aren't big abstract goals but specific experiences like "walking over the Brooklyn Bridge in the morning" or "being in brainstorm meetings with smart people." When evaluating opportunities like the BBC Digital job he was offered, he measured them against these micro-moments and realized none would be included, helping him choose the entrepreneurial path instead. This framework helps entrepreneurs make authentic career choices aligned with their natural energy and interests.