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Why Late-Stage VC Is Breaking Down

Fundraising
May 29, 2025
Explore OpenAI's Jony Ive deal, YC's dominance, and VC myths
Topics discussed in the episode:
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How does dilution affect founders over time?
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Can founders build great companies outside Silicon Valley?
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How are unicorn valuations impacting IPOs?
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Why is Series A investing so challenging today?
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Has YC won the accelerator game?
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Should VCs concentrate capital in top startups?
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Why did OpenAI acquire Jony Ive's design firm?
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How important is rapid growth to $100M ARR?
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How should CEOs communicate AI's impact on staffing?
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How to attract top AI talent amid intense competition?

How does dilution affect founders over time?

Holding investments for longer increases the compounding effect of dilution, significantly impacting founder and investor ownership.

\"It took me a while to internalize... now that companies hold for these investments, you hold them for so long. I did not fully understand the compounding nature of dilution.\"

  • Plan for dilution over the company's lifespan.
  • Set realistic ownership expectations.
  • Consider pro-rata investments to mitigate dilution.

Can founders build great companies outside Silicon Valley?

Founders can build successful startups outside Silicon Valley by leveraging local ecosystems and talent.

\"Actually, you know... people... they think you can only build companies in Silicon Valley... but the smart ones are going, actually, I can get better people for cheaper in London.\"

  • Leverage local talent pools for advantage.
  • Find cost efficiencies outside major hubs.
  • Build strong local networks for success.

How are unicorn valuations impacting IPOs?

Many unicorns face challenges in IPOs due to high private valuations and investor protections that complicate public offerings.

\"What this does is it... removes the ability of that late stage high priced round to get in the way of everything... The market is working.\"

  • Late-stage valuations may not match public markets.
  • Be aware of investor terms that hinder IPOs.
  • Understand investor expectations for exits.

Why is Series A investing so challenging today?

Series A investing is difficult due to intense competition for quality startups and a lower conversion rate from Seed to Series A.

\"Weirdly enough, I agree with you... The conversion rate from Seed to A... has gone way down... For the stuff that's working... there is mass competition.\"

  • Prepare for tougher Series A rounds.
  • Strong traction is crucial to stand out.
  • Build investor relationships early.

Has YC won the accelerator game?

YC has become the dominant accelerator, creating a powerful brand and scale that's unmatched.

\"I think your absolute assumption has to be YC has won. It's the greatest, one of the greatest equity businesses ever.\"

  • Joining YC provides significant advantages.
  • YC's network accelerates startup growth.
  • Consider top accelerators' value in early stages.

Should VCs concentrate capital in top startups?

In venture capital, especially in AI, concentrating capital in the best startups may yield better returns than spreading investments.

\"The only way the math works is if you stuff money into the very best company... and that company turns out to be the big winner.\"

  • Focusing investments on top startups can maximize returns.
  • Diversification may be less effective with large funds.
  • Founders should understand VC strategies during fundraising.

Why did OpenAI acquire Jony Ive's design firm?

OpenAI aims to build a hardware device, leveraging Jony Ive's design expertise to create the \"third device\" after laptops and phones.

\"Sam's so smart, right? And he was clear in that video. He's like, I want the third device... And at first I laughed... But then they said, listen, Chat GPT has crossed 20 minutes per day for the average user.\"

  • OpenAI seeks to deepen user engagement with innovative hardware.
  • Collaborating with top talent can accelerate product development.
  • Consider hardware integration to enhance user experience.

How important is rapid growth to $100M ARR?

Founders often focus on reaching $100 million ARR quickly, but investors weigh multiple factors.

\"You'd be an idiot not to weight it at some level... but you'd also be an idiot to weight it 100%. It's an interesting qualifying proxy, but it's by no means dispositive.\"

  • Understand that speed to $100M ARR is important but not everything.
  • Focus on sustainable growth and solid fundamentals.
  • Balance ambition with building a long-term business.

How should CEOs communicate AI's impact on staffing?

CEOs face challenges in balancing messaging about AI efficiencies and employee job security.

\"I think CEOs for public companies are trying to prepare their teams... but the backlash was too strong. So I just think he had to walk it back to 70% of the truth.\"

  • Be transparent but sensitive when discussing AI's impact on jobs.
  • Avoid overpromising on AI-led efficiencies that might cause employee anxiety.
  • Focus on how AI can augment teams rather than replace them.

How to attract top AI talent amid intense competition?

In the AI boom, hiring and retaining top talent is fiercely competitive, especially with giants like OpenAI and Anthropic.

\"Talent has always been a moth to flames with the hottest startups, right? But AI has just amped it up.\"

  • Founders must develop unique value propositions to attract talent.
  • Compete on mission and impact when salaries are matched.
  • Consider global talent pools and remote work to access broader talent.