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Dalton + MichaelDalton + Michael

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 ↗

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

At a glance

WHAT IT’S REALLY ABOUT

Investors can help, but they won’t win for you

  1. They argue that investors are often misunderstood as “kingmakers” or all-knowing guides, when in reality they rarely make a startup successful directly.
  2. They describe several ways investors can help: motivation and confidence-building, honest feedback delivered without demoralizing the founder, and perspective on best practices if the investor has seen great companies.
  3. They say concrete, reliable investor value is wiring money on good terms and being responsive, and that over-involvement like frequent “strategic” meetings can be counterproductive.
  4. They emphasize investors cannot give you product-market fit, won’t know your customers better than you for long, and won’t solve the hardest problems—founders must do that work.
  5. They frame fundraising as a means to execute toward customer value, warning that believing “raise money → win” reverses cause and effect; winning enables easier fundraising, not vice versa.

IDEAS WORTH REMEMBERING

5 ideas

The best investor “help” can be motivation and belief-building.

Dalton Caldwell says good investors can make founders feel they “belong,” believe they can do it, and feel “fired up,” which he frames as one of the most valuable kinds of help one person can give another.

Often the most helpful investors are the least intrusive.

Michael Seibel argues the baseline, reliable value of investors is that they give you money (and actually wire it), and Dalton adds that a “top 10%” investor may simply be fast, fair, and responsive by email without trying to run the company.

Honest, well-calibrated feedback is a rare but real investor value-add.

Michael says great investors can say the uncomfortable truth without demotivating you, sharing an example from Justin.tv where someone bluntly pointed out that hand-building consumer hardware wasn’t the exciting/viable part.

Investor perspective is valuable only when it’s grounded in real experience with great companies.

Dalton says investors who’ve seen strong companies can “level set” best practices, while Michael emphasizes this only works if the investor has real exposure to good companies; Dalton suggests asking investors what their best funded companies are and checking with those founders.

Introductions can be high-leverage when they connect you to real operators and ground truth.

Both discuss introductions as a concrete benefit: Michael cites a story about getting connected to great CEOs to learn best practices, and Dalton notes an investor introduction is how he and Michael originally met.

WORDS WORTH SAVING

5 quotes

Raising money from an investor, uh, does not mean they can help you be successful.

— Dalton Caldwell

Taking money does not imbue you with product-market fit.

— Dalton Caldwell

And, and if someone seems to either explicitly say or imply they can help you get product-market fit, they are liars.

— Dalton Caldwell

This is the issue with junior investors- ... is that if their career is riding on you- ... they are not gonna be a source of strength.

— Dalton Caldwell

When you win, you raise all the money.

— Dalton Caldwell

Misconceptions about VC “help” and investor marketingMotivation, confidence, and psychological supportMoney as the baseline value of investorsHonest feedback without demoralizing foundersBest-practice perspective from investors who’ve seen great companiesIntroductions to operators and other foundersLimits: product-market fit, customer knowledge, and “kingmaking” myths

High quality AI-generated summary created from speaker-labeled transcript.

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