

'Weird if it didn't work'
Aug 15, 2025
Explore the intriguing mindset of 'Weird if it didn't work' compared to 'could work' in startup success. Discover how understanding product-market fit is crucial for new segments and why real demand should be distinguished from mere interest. Learn why it's essential to create compelling narratives for investors and hire effectively for replicable success. The hosts dive into practical strategies for engaging customers, testing demand, and focusing on what truly matters in building a thriving startup.
AI Snips
Chapters
Transcript
Episode notes
Late Startup Rediscovered Why They Win
- A later-stage startup realized they had product-market fit in one segment but had to rediscover it for new segments.
- Founders sometimes don't actually know why customers buy until they reverse-engineer demand.
Make The Buyer Explicit With Demand Thinking
- Demand-side thinking forces you to state explicitly what customers are buying, avoiding seller assumptions.
- Using case-study style validation reveals the real 'jobs to be done' customers pay for.
Undiversified Founders Need Different Calculus
- Founders must optimize to minimize the chance of not succeeding rather than diversify like a VC.
- That mindset shifts choices toward approaches that would be weird if they didn't work, not just things that could work.