Should You Keep Working on Your Startup?

Dalton Caldwell and Michael Seibel discuss why you should continue working on your startup. Discussion includes: Running out of hope is why most people give up, the natural state of startups is that they are failing, if it doesn't feel like it's working you are probably right but you can fix it, founders get stuck thinking that things happen quickly, repeating year one, good reasons to quit, why you should stop being your worst critic, copying other people, not talking to users, enjoying the ride, disassemble the "if I only had a job at Anthropic" myth, seeking agency, why you are not alone, why you should find wins, why you shouldn't compare to others, escaping the trough of sorrows, 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, Retool, 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 a group partner and leader 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 SeibelhostDalton Caldwellhost

Sep 7, 202614mWatch on YouTube ↗

EPISODE INFO

Released: September 7, 2026
Duration: 14m
Channel: Dalton + Michael
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Dalton Caldwell and Michael Seibel discuss why you should continue working on your startup. Discussion includes: Running out of hope is why most people give up, the natural state of startups is that they are failing, if it doesn't feel like it's working you are probably right but you can fix it, founders get stuck thinking that things happen quickly, repeating year one, good reasons to quit, why you should stop being your worst critic, copying other people, not talking to users, enjoying the ride, disassemble the "if I only had a job at Anthropic" myth, seeking agency, why you are not alone, why you should find wins, why you shouldn't compare to others, escaping the trough of sorrows, 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, Retool, 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 a group partner and leader 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
Managing Director at Y Combinator and co-founder of Justin.tv.
Dalton Caldwell
host
Y Combinator partner and startup founder focused on advising early-stage companies.

EPISODE SUMMARY

In this episode of Dalton + Michael, featuring Michael Seibel and Dalton Caldwell, Should You Keep Working on Your Startup? explores startup success demands persistence through the inevitable trough of sorrows Seibel and Caldwell argue that most startups fail because founders give up during predictable low points, so persistence is often the deciding factor when money and health aren’t immediate constraints.

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