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

(instrumental music) ... seen everything people apply to YC with. People all kinda have the same idea.

One of these themes is simple, pragmatic advice: sell shit, make money.

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.

You have this concept of 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.

Recently, you put out a request for startups, 20 categories of ideas that YC wants to fund.

We're trying to mix up some of the information diet about what kind of ideas people might be contemplating they aren't currently.

A lot of people say you're the king of the pivot.

A good pivot is like going home. It's warmer, it's closer to something that you're an expert at.

Are there other patterns do you find across startups that do well?

There's a lot of founders that come this close to it all being over and, through sheer will, kinda just keep it going.

(instrumental music) Today, my guest is Dalton Caldwell. Dalton is managing director and group partner at Y Combinator, where he's worked for over 10 years across 21 different YC batches, including working closely in the earliest days of Instacart, Retool, Brex, Deel, DoorDash, Webflow, Replit, Amplitude, WhatNot, Razorpay, and 20 other unicorns. Prior to Y Combinator, Dalton was the co-founder and CEO of imeme, which was acquired by MySpace, and co-founder and CEO of App.net, which was an early ads-free competitor to Twitter. Dalton has seen and worked with more startups than nearly any human alive. And, in our conversation, we get incredibly tactical and deep on the startup journey: why it all comes down to simply not losing hope and not letting your startup die; what to do when your startup is struggling and how to know when it is time to give up; what makes a great pivot and signs it's time to pivot; how to actually talk to customers; why every single startup goes through a point where they feel like all hope is lost; why investors say no to startups; what most often leads to startups failing; why you need to avoid over-delegating early on; plus startup ideas that you should avoid, and also 20 ideas Dalton is looking to fund. Also, so many great stories and lessons. This episode is action-packed. With that, I bring you Dalton Caldwell, after a short word from our sponsors. And if you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform, Vanta. Vanta's market-leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risks. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's vanta.com/lenny. (instrumental music) Dalton, thank you so much for being here, and welcome to the podcast.