Good Work with Barrett Brooks

Nathan Barry: Everything We Learned Growing ConvertKit to $40M (and What We'd Do Differently)

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Nathan Barry is the Founder and CEO of ConvertKit. In previous careers, Nathan has been a designer, author, and blogger. After learning the power of email marketing, he gave up a successful blogging career to go all-in on ConvertKit. Outside of work, Nathan spends his time playing soccer, woodworking, and chasing after his three boys.

This week, Barrett and Nathan sit down for a candid conversation about the ups and downs of building a $40M company, and what they wish they had done differently. They also dive into their strategies for growing personal brands, the power of clear roles and communication in projects, building strong team relationships, creating a supportive yet high-performance company culture, and much more. 

In this episode:

  • [00:00] - Intro
  • [04:20] - Why Barrett left ConvertKit
  • [15:18] - Building confidence as a leader
  • [22:59] - "We should have fired more people"
  • [37:57] - Creating a healthy feedback culture
  • [44:13] - Strategies for better communication
  • [58:14] - Designing comp and benefits
  • [01:07:46] - What we nailed on the growth side (and what we could have done differently)
  • [01:23:10] - Lessons learned from Barrett's departure
  • [01:36:20] - Podcasting for the long haul
  • [01:52:16] - On brand differentiation
  • [01:55:52] - Who Nathan is becoming


    • Get full show notes and links at https://GoodWorkShow.com.

    Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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    Good Work with Barrett BrooksBy Barrett Brooks
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