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Y CombinatorY Combinator

Why Investors Can’t Fix Your Company – Dalton Caldwell and Michael Seibel

Dalton Caldwell and Michael Seibel on common pitfalls in the advice from different types of investors and why you, the founder, are ultimately responsible for the success of your company. Chapters (Powered by https://bit.ly/chapterme-yc) - 00:00 - Why investors including YC can't fix their company? 01:56 - Investor with the finance background 02:33 - Balance Sheet 04:14 - Big Company Exec 05:37 - What does failure look like for a lot of our companies? 08:01 - Successful entrepreneur in non-tech 09:49 - Junior investor 12:25 - Influencer / Famous person 12:58 - What is the advice that founders get from other entrepreneurs? 14:25 - Founders 14:42 - founders 15:54 - Extremely young investor (Scout) 17:17 - Wrap up 17:22 - YC partner common bad advice 19:44 - Personal accountability 19:57 - Big takeaway 21:20 - Great investor advice

Michael SeibelhostDalton Caldwellhost
Feb 23, 202224mWatch on YouTube ↗

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

At a glance

WHAT IT’S REALLY ABOUT

Why Investors, Including YC, Can't Fix Your Startup's Problems

  1. Seibel and Caldwell walk through common investor archetypes, including finance people, big-company execs, non-tech entrepreneurs, junior investors, influencers, fellow founders and very young scouts, each giving advice shaped by their own experience.
  2. They argue that much of this advice isn't wrong in itself but is mistimed, such as throwing money or hiring executives at a company that hasn't reached product market fit.
  3. They admit YC partners also give bad advice, notably treating the lean startup path of an early MVP and talking to users as the right path for everyone.
  4. Their central message is that no investor can tell a founder exactly how to win, so founders must take personal accountability and decide how to use the advice around them.
  5. The best advice they received came from people who pointed out problems or synthesized what was working, ideally from someone with no financial stake.

IDEAS WORTH REMEMBERING

5 ideas

Advice reflects the advisor's background

Each investor type tends to prescribe the tools they know, such as money, scaling processes, franchise-style control, or their own personal experience. Founders can often trace advice back to the type of person giving it.

Good advice is often mistimed rather than wrong

Seibel notes that throwing money at a company or hiring executives is right post-product market fit. The trouble comes when it's given always, including before product market fit.

Early failure often means zero real customers

Caldwell says failure for many YC companies is getting no real customers at all, not missing a Series A. Big-company thinking may not even register that you can fail this badly.

Incentives shape what investors tell you

Junior investors need quick markups to protect their careers, so they push fundraising and scaling and say things are working. They are cheerleaders with good intentions, but it is hard for them to dig into what is broken.

Influencers don't solve distribution

Caldwell says founders often feel they got a raw deal from celebrity posts, and Seibel says the most reputable ones don't promise distribution. Founders seeking a silver bullet set expectations too high.

WORDS WORTH SAVING

5 quotes

When all you have is a hammer, everything's a nail. And so if what you know is money, the solutions usually involve money.

— Dalton Caldwell

Silver bullets don't exist.

— Michael Seibel

The founders that made it work believed in themselves, and they knew that we couldn't fix it.

— Dalton Caldwell

The best investors point out the problem. They don't give you a solution. They just point out the problem.

— Michael Seibel

They all have your interests in mind, but none of us can tell you exactly what to do to win. None of us.

— Michael Seibel

Investor types and their biasesFinance-background investors and money-based solutionsBig company execs versus zero-to-one experienceJunior investors and incentive to mark upInfluencer and celebrity investorsYC partners' own bad adviceFounder accountability

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

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