How to Conquer Bad Days at Your Startup

Dalton and Michael discuss how great founders handle the worst days of building a startup. They explain why setbacks are part of the job and how to keep working the problem when everything feels like it’s going wrong. They share how confronting the worst-case scenario can put a crisis in perspective, why rapid growth often brings more problems, and how difficult moments can force the breakthroughs your company needs. Along the way, they discuss Sam Altman’s response to being fired from OpenAI, the early days of Twitch, and how Airbnb turned a late-night customer emergency into a surprisingly good experience. Discussion includes: • Why most jobs don’t prepare you for the emotional reality of being a founder • How examining the worst-case scenario can reduce fundraising anxiety • The bandwidth bill that almost bankrupted Justin.tv • How Sam Altman approached one of his worst days at OpenAI • Why startup growth brings more problems, not fewer • How to process a bad day and keep moving • Turning a customer crisis into a better product and experience — Dalton + Michael is brought to you by @Standard_Cap. Standard Capital is the AI-native Series A fund. Learn more at 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, Stoke 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.

Michael Seibelhost

Oct 26, 202614mWatch on YouTube ↗

EPISODE INFO

Released: October 26, 2026
Duration: 14m
Channel: Dalton + Michael
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Dalton and Michael discuss how great founders handle the worst days of building a startup. They explain why setbacks are part of the job and how to keep working the problem when everything feels like it’s going wrong. They share how confronting the worst-case scenario can put a crisis in perspective, why rapid growth often brings more problems, and how difficult moments can force the breakthroughs your company needs. Along the way, they discuss Sam Altman’s response to being fired from OpenAI, the early days of Twitch, and how Airbnb turned a late-night customer emergency into a surprisingly good experience. Discussion includes:
Why most jobs don’t prepare you for the emotional reality of being a founder
How examining the worst-case scenario can reduce fundraising anxiety
The bandwidth bill that almost bankrupted Justin.tv
How Sam Altman approached one of his worst days at OpenAI
Why startup growth brings more problems, not fewer
How to process a bad day and keep moving
Turning a customer crisis into a better product and experience
— Dalton + Michael is brought to you by @Standard_Cap. Standard Capital is the AI-native Series A fund. Learn more at 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, Stoke 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
host
Startup founder and investor; co-host of Dalton + Michael.

EPISODE SUMMARY

In this episode of Dalton + Michael, featuring Michael Seibel, How to Conquer Bad Days at Your Startup explores bad days are inevitable—and they’re how startup founders grow Michael Seibel argues that founders often remember near-failure moments more clearly than headline successes because those crises drive the most learning and growth.

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