Shut It Down or Double Down: Nathan Barry’s Road to $45M with Kit (ConvertKit)

Nathan Barry, the creator behind ConvertKit (now rebranded as Kit) came to visit my Inner Circle and gave a very special presentation. Nathan’s journey from a designer to building a software empire fascinated me. He originally tried to solve his frustrations with MailChimp and, in doing so, founded a business that today generates $45 million annually.

In this episode, Nathan and I unpack the lessons he’s learned from building and scaling ConvertKit to rebranding it into something bigger. He offers transparent insights into the challenges of entrepreneurship, including the crucial moments when you have to either shut down or double down.

Throughout the conversation, Nathan opens up about the turning points that shaped his business. From battling churn to leveraging direct sales in the early days, he shares how a relentless focus on product quality and customer experience laid the foundation for his success. He also discusses his decision to turn down a $200 million acquisition offer and the ripple effects it had on his executive team—proving that even the right decision can bring new challenges.

Key Highlights:

• Shutting Down or Doubling Down: The pivotal question every entrepreneur faces when their business stalls.
• Fighting Churn: Strategies Nathan used to reduce churn, including shifting customers to annual plans.
• The Power of Direct Sales: Why doing things that don’t scale—like concierge migrations—helped build momentum early on.
• Rebranding and SEO Challenges: How transitioning to kit.com presented unique hurdles and opportunities.
• The Importance of Execution: Why Nathan built a habit of writing 1,000 words a day for 600 days—and how it fueled his entrepreneurial success.

This episode is literally packed with valuable insights for anyone navigating the ups and downs of scaling a business. Tune in to learn practical strategies for growing your audience, retaining customers, and staying focused on what matters most.

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