The 'It Sucks That' Problem Method

Henrik Werdelin is one of my favorite entrepreneurs. He’s founded and incubated several unicorns, most notably BARK, the dog happiness company.

Henrik himself is a pretty happy guy — an optimistic guy who likes to ask what could go right? — and on the day we recorded (a few months ago as I was squirreling away interviews for the podcast relaunch), he helped me see through some future of tech gloom I was feeling. I honestly can’t even remember what Trump+tech hellscape we were living through that week, but I do remember that Henrik put me in a better mood. I think he’ll do the same for you, no matter how you’re feeling. 🤗

Henrik believes AI could be a massive force for good. That it could bring forth a whole new — a better! — form of capitalism. He writes about this is in his latest book, Me, My Customer, and AI. He points to those (like Henry Ford) who took advantage of electricity by making drastic, not incremental, changes to how the build things. Our conversation pairs nicely with my recent episode with Azeem Azhar, who said the AI winners will “come from odd places”, as they have in previous tech transformations. 

Here’s more of what Henrik and I cover:

• His concept of "relationship capital"—the moat AI can't clone—and why the companies that win next will be defined by who they serve, not what they make
• The three components of relationship capital: intensity, community, and durability
• The "it sucks that" method for finding problems worth solving (he took it to a fifth grade class; the teacher was not thrilled)
• His vision for the "headless", agentic web, where your startup's MVP is a group of agents, not an app
• The wildly practical AI tools he's built just for himself: a custom CRM that searches by vibes not names, a newsletter bot tuned to his quarterly goals, and an agent that handled his visa paperwork while he was in a meeting
• Why entrepreneurial skills—agency, narrative, resourcefulness—are the ultimate career insurance, whether you start a company or not
• The absolutely ridiculous story of how a prank on a cruise ship led to him meeting his BARK co-founder in a heart-shaped bed

Chapters

• (01:43) - Two Futures: AI Bad vs. AI Really, Really Good
• (05:44) - Why Positivity Is Actually the Riskier Bet
• (09:05) - Electricity, AI, and the Rise of Relationship Capital
• (11:12) - The Three Components of Relationship Capital
• (14:20) - "It Sucks That" — The Best Way to Find a Real Problem
• (19:22) - The Headless Future and Minimum Viable Agents
• (22:40) - N-of-One Software: Building Tools Just for Yourself
• (26:48) - Henrik's Custom Newsletter Bot and AI-Powered CRM
• (30:59) - Warp, Obsidian, and Letting Agents Loose on Your Computer
• (34:45) - Entrepreneurial Skills as Career Insurance
• (36:53) - The Heart-Shaped Bed: How Henrik Met His BARK Co-Founder

Links & Resources

• Henrik Werdelin on LinkedIn
• Audos, Henrik’s latest venture where he hopes AI agents trained in his methods can help thousands of entrepreneurs (donkeycorns!) a year
• Beyond the Prompt podcast, from co-hosts Henrik Werdelin and Jeremy Utley

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Music by Jonathan Zalben