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What Should You Expect From Investors?

Dalton Caldwell and Michael Seibel discuss what founders should actually expect from their investors. Where can a good investor make a difference, and which parts of building a startup will always be the founder’s responsibility? They share examples from Justin.tv, YC, and their own experiences as founders and investors. Discussion includes: • What good investors actually do for founders • Why a fast check on good terms can be more valuable than promises of hands-on help • Giving honest feedback without demotivating founders • Learning from successful companies and getting useful introductions • Why young investors whose careers depend on your startup can add stress • Why funding doesn’t validate your idea or give you product-market fit • Tactical advice from Paul Buchheit that helped Justin.tv and Socialcam • The “kingmaking” myth, and why big funding rounds don’t guarantee winners • Treating fundraising as a means to serve customers and build a great business — 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, Twitch sold to Amazon for $970m. — Are you an AI builder? Check out StandardDB..com Discover offers, credits, tools, and partner programs from the StandardDB ecosystem.

Dalton CaldwellhostMichael Seibelhost

Nov 2, 202624mWatch on YouTube ↗

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EPISODE INFO

Released: November 2, 2026
Duration: 24m
Channel: Dalton + Michael
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Dalton Caldwell and Michael Seibel discuss what founders should actually expect from their investors. Where can a good investor make a difference, and which parts of building a startup will always be the founder’s responsibility? They share examples from Justin.tv, YC, and their own experiences as founders and investors. Discussion includes:
What good investors actually do for founders
Why a fast check on good terms can be more valuable than promises of hands-on help
Giving honest feedback without demotivating founders
Learning from successful companies and getting useful introductions
Why young investors whose careers depend on your startup can add stress
Why funding doesn’t validate your idea or give you product-market fit
Tactical advice from Paul Buchheit that helped Justin.tv and Socialcam
The “kingmaking” myth, and why big funding rounds don’t guarantee winners
Treating fundraising as a means to serve customers and build a great business
— 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, Twitch sold to Amazon for $970m. — Are you an AI builder? Check out StandardDB..com Discover offers, credits, tools, and partner programs from the StandardDB ecosystem.

SPEAKERS

Dalton Caldwell
host
Dalton Caldwell is a startup founder and Y Combinator partner who advises early-stage companies on fundraising and growth.
Michael Seibel
host
Michael Seibel is a startup founder and former Y Combinator partner/investor, known for co-founding Justin.tv (Twitch).

EPISODE SUMMARY

In this episode of Dalton + Michael, featuring Dalton Caldwell and Michael Seibel, What Should You Expect From Investors? explores investors can help, but they won’t win for you They argue that investors are often misunderstood as “kingmakers” or all-knowing guides, when in reality they rarely make a startup successful directly.

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