Dalton Caldwell
Managing Director & Group Partner at Y Combinator
Managing Director and Group Partner at YC for 10+ years across 21 batches; worked closely with Instacart, Retool, Brex, DoorDash, Webflow, Replit, Amplitude, and 20+ other unicorns in their earliest days; former founder of imeem and App.net.
Dimension Profile
Key Themes
Episode Summary
Dalton Caldwell, who has worked with more startups than nearly any human alive through 21 YC batches and 20+ unicorns, shares deeply practical startup wisdom centered on his 'just don't die' mantra. He introduces the concept of tarpit ideas that trap founders with false positive feedback, explains how to know when to pivot vs persevere, and argues that the fundamentals — sell, make money, talk to customers — matter more than anything else.
Leadership Principles
- → Just don't die — being coached and reminded of the fundamentals puts you in the right mindset for survival
- → Tarpit ideas seem like unsolved problems and get positive feedback, but people have been starting that startup since the '90s — avoid them
- → Sell shit, make money — the most pragmatic startup advice is also the most important
Notable Quotes
"One of my mantras is just don't die. Being coached and being reminded of the fundamentals and basics puts you in the right mindset."
— On the most important startup advice from someone who's seen thousands of startups
"Tarpit ideas — seems like an unsolved problem. You'll get all this positive feedback from the world and people have been starting that startup since the '90s."
— On the most dangerous type of startup idea
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