LU 352: Doubling Down Instead of Shutting Down with Nathan Barry, Founder and CEO of ConvertKit (podcast) With Nathan Barry

ConvertKit is one of the biggest success stories of the 2010s online business world. Today we are joined by their founder and CEO Nathan Barry! Nathan started ConvertKit after realizing the value of email marketing and the ways in which companies were missing important parts of the service he envisaged. We get to hear about this part of the story, leading up to the beginnings of the company and then the early successes that they experienced after launching. A completely transparent company, Nathan shares a lot of vital and interesting statistics from ConvertKit before we get into Nathan’s strategy for targeting new customers that has served them so well. He also emphasizes the importance of storytelling at ConvertKit, believing that customers do not only buy into the service but also the story. We discuss product-led growth, ConvertKit’s recent adoption of the freemium model and public appearances that Nathan makes at the moment, so do not miss it!


  • [00:21] Before we jump into today’s interview, please rate, review, and subscribe to the Leveling Up Podcast!
  • [00:44] The full range of services offered by ConvertKit and their company mission.
  • [01:08] Nathan’s background in design, blogging, and writing, and how this led to ConvertKit.
  • [02:59] Early days at ConvertKit and the success they experienced from the get-go.
  • [04:02] Nathan’s approach to entrepreneurship and why he chooses to focus on one company.
  • [07:29] Growth phases for the company and how long it took to get up to 100k MRR.
  • [10:17] The pricing model at ConvertKit and how they charge. 
  • [10:57] Important numbers from the business and their choice to be transparent.
  • [11:53] Smart targeting and the lessons that Nathan learned about zeroing in. 
  • [15:01] Nathan’s social media strategy and becoming visible to new prospects.
  • [15:57] ConvertKit’s choice to make the shift to a freemium model recently. 
  • [19:56] Benefits of a great free and product-led growth.
  • [21:10] The role of webinars and podcasts in the trajectory of ConvertKit.
  • [24:50] How many podcast appearances Nathan makes at the moment.
  • [25:53] Nathan’s must-read book recommendation!
  • [26:21] A great tool for business growth according to Nathan.
  • [27:32] The founder and company that Nathan is currently following.

Resources From The Interview:

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