Episode Details
EPISODE INFO
- Released
- September 14, 2026
- Duration
- 23m
- Channel
- Dalton + Michael
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
Should you pivot your company? Or do you just have a case of the "pivots"? It's easier than ever to pivot but that might not be the right decision. Dalton Caldwell and Michael Seibel discuss an all-important topic: the pivot. Discussion includes: diagnosing the reason for the pivot, having good ideas, trying your core hypothesis, embrace hard work, why dentist startups becomes a popular pivot choice, are you using your own product, how the AI changes how you can pivot, avoiding "pivot hell" at all costs, force yourself to work on an idea for at least three months, default to your experience, avoiding "cope", making the big move when you have no information, when to declare emotional bankruptcy, making a big move in a post-AI word, making the company work, investor concerns about pivots, why a good pivot feels like "coming home", and more. – Standard Capital is the AI-native Series A fund. Learn more at 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. – Are you an AI builder? Check out StandardDB. Discover offers, credits, tools, and partner programs from the StandardDB ecosystem.
SPEAKERS
Michael Seibel
hostYC partner and co-founder/early executive at Twitch/Justin.tv, known for advising startups on product direction and pivots.
Dalton Caldwell
hostYC partner and startup founder who co-hosts Dalton + Michael, focusing on practical frameworks for startup decision-making and pivots.
EPISODE SUMMARY
In this episode of Dalton + Michael, featuring Michael Seibel and Dalton Caldwell, Should You Pivot Your Startup? explores how to Decide on Pivoting Without Falling Into Pivot Hell Seibel and Caldwell frame pivot decisions as a diagnostic process driven by context—time spent, customer learning, founder alignment, objective progress, and the quality of backup ideas.
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