Dalton Caldwell
Co-Founder & General Partner @ Standard Capital
Co-founding Standard Capital, an AI-native Series A firm. Former Managing Partner at Y Combinator.
βResilience, tar pit ideas, pivoting, more, covering startup building, product design, and measurement and analysis.β
Career History
| Company | Role | Years |
|---|---|---|
| Standard Capital | Co-Founder & General Partner | 2025-present |
| Y Combinator | Managing Partner (prev. Partner) | 2011-2025 |
| App.net | Co-Founder & CEO | ~2012-~2014 |
| imeem (acquired by MySpace) | Co-Founder & CEO | ~2003-2009 |
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βYeah. Thanks so much, Lenny. I'm really excited to talk to you today. It's been great.β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βAnd so that is the theme that is a summary and I provide lots of data and lots of stories there, but this is one of those things that the longer I have this job, the more I really, really believe this...β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βThey thought it was really high-tech. They want to do a really high-tech startup, and so they're like, "We're going to build a new VR headset." And yeah, they were good programmers, but they just didn...β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βThere was no universe where they would've made up the idea for Segment because they didn't know anything about how analytics worked, but because they were grinding for multiple years and became expert...β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βAnd they did that. They basically found out about all this procurement software and what the state of the art was and that was the prompt. Again, maybe he told you this, that was basically the process...β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βYeah, I mean, I can't promise that works for everyone, but again, in the very bespoke situation with Rujul, it worked really well because he actually knew exactly once he locked in on that prompt, oh ...β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βOf course. Sorry. Yeah. We got to give Lou the shout-out. Lou did an amazing job. I just didn't know Lou as well before he did YC. But you're right, we got to give Lou the credit.β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βDo you remember when Foursquare clones was all anyone worked on for-β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βYeah. Because again, if you ask someone or put yourself in the investor's shoes, wouldn't you be making decisions the same way? Usually founders are like, "Yeah." If you do that exercise, a lot of thi...β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βAnd again, Whatnot. What's the TAM of the collectible Funko Pop industry? I don't know. I don't think it's that big, man. I don't know if you did that analysis when you invested, but I think is pretty...β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βOh, Cool. Okay. I don't know if I can feed with that. All right.β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
βYeah, you're out of ideas. You're like, "I'm done." If in your heart that you're done, you don't have to keep going through the motions. No one benefits.β
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)