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Title:Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (YC)

Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss: • Why founders need to adopt the mindset “Just don’t die” • The most common reason startups fail • When to pivot, and characteristics of a good pivot • The concept of “tar pit ideas” and examples of bad startup ideas • Why investors say no to startups • The importance of market size in investment decisions • The pitfalls of founders over-delegating • Effective ways to talk to customers • 20 ideas Dalton is looking to fund — Brought to you by: • Eppo—Run reliable, impactful experiments: • Vanta—Automate compliance. Simplify security: • Coda—The all-in-one collaborative workspace: Find the transcript at: Where to find Dalton Caldwell: • X: • LinkedIn: Where to find Lenny: • Newsletter: • X: • LinkedIn: In this episode, we cover: (00:00) Dalton’s background (04:41) The value of simple advice (07:04) Dalton’s advice: “Just don’t die” (08:39) Knowing when to stop (11:45) Deciding to pivot (14:26) Characteristics of a good pivot (17:53) Knowing when to pivot (19:03) Zip’s journey and finding a market (21:22) Why Dalton says to “Move towards the mountains and the desert” (23:45) Tar pit ideas (26:49) Understanding why investors say no (29:14) The importance of market size (32:16) Avoiding over-delegation and hiring senior people too early (36:43) Why startups fail (40:30) Effectively talking to customers (45:17) Examples of startups hustling to talk to customers (48:01) Patterns of successful startups (52:05) YC’s Request for Startups (55:37) Early days of Silicon Valley (01:05:33) Contrarian corner: growth hacking for early startups (01:09:28) Failure corner (01:11:15) Closing thoughts (01:12:22) Lightning round Production and marketing by For inquiries about sponsoring the podcast, email Lenny may be an investor in the companies discussed.


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