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SPI 244: Bootstrapping a Startup with Nathan Barry from ConvertKit

Nathan Barry is back, and in this episode, he’s giving you a look under the hood at his own email marketing company, ConvertKit. If you’ve ever wondered how to bootstrap a business, this is the episode for you.

Nathan has built and grown ConvertKit using customer funding and money from his own pocket—and that’s all. He’s here today to reveal how he did it, and what you should expect when bootstrapping a business of your own. You’ll learn how he structures his business, how it’s grown, where it’s headed, who gets paid when, and lots, lots more.

As an advisor and current customer of ConvertKit, I’ve watched Nathan accomplish amazing things with his business. Don’t miss this story—you just might hear a few things that’ll inspire your own business growth, too!

Thanks for Listening!

Thanks so much for joining me again this week. Have some feedback you’d like to share? Leave a note in the comment section below!

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If you have any questions (or would like answers to hear previously submitted voicemail questions!), head on over to This bite-sized show has over two million downloads and counting!

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Special thanks to Nathan for joining me this week. Until next time!

Today’s Guest

Nathan Barry

ConvertKit’s Founder and CEO shares his journey in bootstrapping a business and growing a software company from the ground up.

You’ll Learn

  • What kind of growth to expect when bootstrapping your business.
  • How ConvertKit is doing in revenue, subscribers, and more.
  • How Nathan uses his advisors, and what they do for ConvertKit.
  • Small steps Nathan and his team take to grow their business each day.
  • Why bootstrapping isn’t for everyone.
  • Major pitfalls and oversights to avoid when building your business.
  • Why you should embrace rejection and criticism when validating your business idea.
  • How long it took until Nathan began taking a salary.
  • Why Nathan doesn’t hire part-time, and more!


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