When to Convince AI Skeptics (or When to Move On)

When should you help an AI skeptic see the value, and when should you move on? Dalton and Michael discuss how founders can navigate AI skepticism among employees, customers, friends, and family, and why a useful firsthand experience often does more than an argument. They explain how to make AI adoption part of your company’s culture, what to ask candidates about AI during interviews, and why customers care more about outcomes than the technology behind them. They also discuss helping the people you care about get started, working around skeptical bosses, and recognizing when convincing employees is taking time away from building your business. Discussion includes: showing instead of telling, why trying an old free model can create lasting skepticism, helping friends and family experience AI’s value, sharing useful workflows with your team, avoiding performative AI adoption, screening for AI use in interviews, setting expectations for employees, selling outcomes to skeptical customers, navigating bosses who block AI, and knowing when to stop debating and move on. — 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, 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. StandardDB.com

Dalton CaldwellhostMichael Seibelhost

Oct 19, 202623mWatch on YouTube ↗

EPISODE INFO

Released: October 19, 2026
Duration: 23m
Channel: Dalton + Michael
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

When should you help an AI skeptic see the value, and when should you move on? Dalton and Michael discuss how founders can navigate AI skepticism among employees, customers, friends, and family, and why a useful firsthand experience often does more than an argument. They explain how to make AI adoption part of your company’s culture, what to ask candidates about AI during interviews, and why customers care more about outcomes than the technology behind them. They also discuss helping the people you care about get started, working around skeptical bosses, and recognizing when convincing employees is taking time away from building your business. Discussion includes: showing instead of telling, why trying an old free model can create lasting skepticism, helping friends and family experience AI’s value, sharing useful workflows with your team, avoiding performative AI adoption, screening for AI use in interviews, setting expectations for employees, selling outcomes to skeptical customers, navigating bosses who block AI, and knowing when to stop debating and move on. — 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, 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. StandardDB.com

SPEAKERS

Dalton Caldwell
host
Startup founder and investor; co-host of the Dalton + Michael show.
Michael Seibel
host
Startup founder and investor; co-host of the Dalton + Michael show.

EPISODE SUMMARY

In this episode of Dalton + Michael, featuring Dalton Caldwell and Michael Seibel, When to Convince AI Skeptics (or When to Move On) explores convert AI skeptics with firsthand wins, not endless debate Caldwell and Seibel argue that the best way to convert AI skeptics is to create a personal experience of value rather than engaging in abstract or moral debates.

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