Podcast · ~60 min episodes

How I Built This with Guy Raz

Guy Raz · Apple Podcasts (NPR / Wondery) Free Beginner

Long interviews where founders retrace how they came to their problem, the raw material of a good 'why you.' Listening to a few episodes trains your ear for authentic origin stories versus polished ones. A relaxed way to learn what conviction actually sounds like.

  • Real founder stories are specific, personal, and often accidental.
  • The problem usually finds the founder before the company exists.
  • Obsession, not a plan, carries founders through the early years.
Listen on Apple Podcasts ↗

The question it answers

  1. I keep hearing 'why you' matters to investors. What are they actually looking for when they ask it?

Read with it

  1. The definitive essay on where good ideas come from: notice problems you personally have, don't force it. Use it as the lens for... paulgraham.com Essay · ~20 min read How to Get Startup Ideas Paul Graham
  2. A modern, tactical fundraising and pitch playbook aggregating advice from top operators and investors. Strong on how to build... Lenny's Newsletter Article · 25 min read A Playbook for Fundraising (and building your pitch) Lenny Rachitsky
  3. First Round Review turns storytelling from a buzzword into concrete pitch structure, drawing on a former Pixar CTO's approach.... First Round Review Article · 20 min read Take Your Fundraising Pitch from Mediocre to Memorable with Storytelling First Round Review
  4. A YC partner who has read thousands of applications tells you plainly what separates the founders who get in from the ones who... YC Startup Library Essay · Long-form essay / talk How to Apply and Succeed at Y Combinator Dalton Caldwell
  5. Video · ~35 min How to Pitch Your Startup Kevin Hale
  6. This piece takes the exact stance the question is testing: fit is earned, not handed to you on day one. Its line, you earn fit... StartUp to Scale Up Article Founder-Market Fit: What It Is and How to Prove You Have It James Sinclair
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