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THE FEAR

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Jon and Justin talk about "optionality" in bootstrapping. (Justin is concerned, Jon thinks we should just enjoy the moment).

  • DHH: "Part of what gave us the confidence to turn down the whole world of venture capital was a small sale of equity to Jeff Bezos. That gave our personal bank accounts just enough ballast that the big numbers touted by VCs and acquisition hunters lost their lure."
  • Are we at peak podcasting? Things are good right now - will they be good for 10 years? 20 years?
  • Fred Wilson: "Taking money off the table."
  • How much did the founders of Buffer, Robinhood, etc. take off the table? Article.
  • Des Traynor: "A founder is spending 60 months of their best years in their startup (instead of their career). That is a substantial upfront investment; it's like a seed round, but instead of money, it's your life."
  • How much richer than us is Jeff Bezos?

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Thanks to our monthly supporters
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  • Greg Park
  • Mitchell Davis from sixsides.co
  • Marcel Fahle, wearebold.af
  • Bill Condo (@mavrck)
  • Ward from MemberSpace.com
  • Evandro Sasse
  • Austin Loveless
  • Michael Sitver
  • Colin Gray
  • Dave Giunta

πŸŽ™οΈ Podcast hosting is provided by Transistor.fm.
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162 episodes

Artwork

THE FEAR

Build Your SaaS

588 subscribers

published

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Fetch error

Hmmm there seems to be a problem fetching this series right now. Last successful fetch was on October 10, 2025 14:42 (2M ago)

What now? This series will be checked again in the next day. If you believe it should be working, please verify the publisher's feed link below is valid and includes actual episode links. You can contact support to request the feed be immediately fetched.

Manage episode 272079277 series 2121450
Content provided by Transistor.fm. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Transistor.fm or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://player.fm/legal.

Jon and Justin talk about "optionality" in bootstrapping. (Justin is concerned, Jon thinks we should just enjoy the moment).

  • DHH: "Part of what gave us the confidence to turn down the whole world of venture capital was a small sale of equity to Jeff Bezos. That gave our personal bank accounts just enough ballast that the big numbers touted by VCs and acquisition hunters lost their lure."
  • Are we at peak podcasting? Things are good right now - will they be good for 10 years? 20 years?
  • Fred Wilson: "Taking money off the table."
  • How much did the founders of Buffer, Robinhood, etc. take off the table? Article.
  • Des Traynor: "A founder is spending 60 months of their best years in their startup (instead of their career). That is a substantial upfront investment; it's like a seed round, but instead of money, it's your life."
  • How much richer than us is Jeff Bezos?

Want to reply to something we said?

Thanks to our monthly supporters:

Thanks to our monthly supporters
  • Rewardful.com
  • Greg Park
  • Mitchell Davis from sixsides.co
  • Marcel Fahle, wearebold.af
  • Bill Condo (@mavrck)
  • Ward from MemberSpace.com
  • Evandro Sasse
  • Austin Loveless
  • Michael Sitver
  • Colin Gray
  • Dave Giunta

πŸŽ™οΈ Podcast hosting is provided by Transistor.fm.
πŸ“Ί Learn
how to start your own podcast!

β˜… Support this podcast on Patreon β˜…
  continue reading

162 episodes

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