Biggest Founder Regrets

ℹ️ EPISODE INFO

Released

November 9, 2026

Duration

17m

Channel

Dalton + Michael

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

Dalton Caldwell and Michael Seibel discuss the biggest regrets founders share when shutting down their startups—and what you can learn from them while you still have time to act. Drawing on hundreds of conversations with founders, they explain why people wait too long to pivot, avoid fixing team problems, and chase last-minute Hail Marys instead of confronting hard truths. They also discuss how to protect your energy, why guilt about investor money can keep a struggling company alive too long, and why founders rarely regret starting a company—even when it fails. Their advice: imagine you're shutting down a year from now, identify what you'd wish you'd done differently, and make those changes today. In this episode:

• Why founders put off hard decisions until they're almost out of money
• The regret of never fully testing your startup’s core hypothesis
• Choosing the wrong co-founder and leaving team problems unresolved
• Why another fundraise or launch won’t necessarily save your company
• Preserving your founder “health bar” and avoiding burnout
• How founders misunderstand their obligations to investors
• Why a failed startup can make you a stronger founder—and a more valuable hire
• Why fundraising often gets easier the second time around

~ Dalton + Michael is brought to you by @Standard_Cap. Standard Capital is the AI-native Series A fund. Learn more at [https://standardcap.com](https://standardcap.com) About Dalton: Dalton Caldwell is Co-Founder and Partner of Standard Capital. He spent 12 years at Y Combinator, where he served as Managing Partner, worked across 25 YC batches, and advised more than 1,000 startups. His investments include Whatnot, Brex, GitLab, PostHog, Stock Space, Rappi, Razorpay, and Oklo. Before becoming an investor, Dalton founded imeem and App.net. About Michael: Michael Seibel is a Partner Emeritus at Y Combinator, where he served as Managing Partner of the early stage accelerator from 2014 - 2024. Michael also serves on the board of three companies: Reddit, Dropbox, and Kalshi. He moved to the bay area in 2006, and was a co-founder and CEO of two Y Combinator startups Justin.tv/Twitch (2007 - 2011) and Socialcam (2011 - 2012). In 2012 Socialcam sold to Autodesk Inc. for $60m and in 2014, under the leadership of Emmett Shear (CEO) and Kevin Lin (COO) Twitch sold to Amazon for $970m.

🎤 SPEAKERS

• Dalton Caldwell

  host

  Managing Director at Y Combinator and startup founder known for advising early-stage companies.

• Michael Seibel

  host

  Managing Director at Y Combinator and entrepreneur (Justin.tv/Socialcam) focused on early-stage startup advice.

🧾 EPISODE SUMMARY

In this episode of Dalton + Michael, featuring Dalton Caldwell and Michael Seibel, Biggest Founder Regrets explores Founders’ biggest shutdown regrets: delayed decisions, team issues, false obligations Michael Seibel and Dalton Caldwell discuss patterns they repeatedly see in shutdown postmortems with founders, focusing on regrets that show up when a startup is ending.

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