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Dalton + MichaelDalton + Michael

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 ↗

At a glance

WHAT IT’S REALLY ABOUT

Bad days are inevitable—and they’re how startup founders grow

  1. Michael Seibel argues that founders often remember near-failure moments more clearly than headline successes because those crises drive the most learning and growth.
  2. A speaker describes startup life as exposure to raw, unfiltered feedback and consequences, requiring founders to stay grounded on great days and steady on terrible ones.
  3. They emphasize that bad days are normal, don’t necessarily mean you did something wrong, and should be expected rather than treated as a sign to quit.
  4. They discuss a tactical approach for bad days: name the feared outcome, walk through the true worst case, and realize it is often survivable and actionable.
  5. They share examples where crisis led to rapid problem-solving—like innovating to handle unaffordable infrastructure costs or turning a customer emergency into a surprisingly good experience.

IDEAS WORTH REMEMBERING

5 ideas

Bad days can be the most formative moments in a startup.

He contrasts the fuzzy memory of a major success moment with vivid, minute-by-minute recall of multiple near-death moments, arguing those crises were where real growth happened.

Founders experience higher highs and lower lows because reality reaches them directly.

A speaker describes startups as exposing you to “cold, unfiltered reality,” including hate mail, bad press, and intense emotional swings, unlike the buffered experience inside big companies.

Emotional steadiness matters on both good days and bad days.

The conversation emphasizes that founders must avoid delusions on good days and learn to take bad days in stride, because bad days are normal and recurring—not evidence you did something wrong.

Examining the “worst case” reduces fear and restores clear thinking.

One practical method discussed is to put the feared outcome on the table and ask “So what?”, often revealing the consequence is survivable (e.g., worrying about fundraising when there is ample runway and customers aren’t tracking it).

Resource constraints and crises can force innovation and decisive action.

Michael Seibel shares receiving a bandwidth bill larger than the company’s bank balance, framing it as a forcing function that drives problem-solving and innovation when you can’t rely on a boss or an organization to absorb the shock.

WORDS WORTH SAVING

5 quotes

Tell me the story of the five times Twitch died, almost died. I remember those, like, minute by minute.

— Michael Seibel

I'm not saying you want bad days. I'm saying bad days teach you a lot more than good days do.

— Michael Seibel

But when you're running a startup, you are getting cold, unfiltered reality.

— Unattributed

You're normal. You're not unusual if you feel like you have days that make you wanna quit your startup and give up. Like, yep, that's pretty much part of it.

— Unattributed

Counterintuitively, the better you're doing, the more bad days you're gonna have.

— Michael Seibel

Bad days vs. good days as learning momentsUnfiltered reality of founder lifeManaging ego and despairWorst-case thinking (“so what?”)Crisis-driven innovation under constraintsExpectations about success and stressHandling customer emergencies without panicking

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