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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Michelle Zatlyn, co-founder and President of Cloudflare, returns to Grit to discuss how her company has evolved into an $80 billion enterprise while maintaining its mission to help build a better internet. (01:00) The conversation explores Cloudflare's 15-year journey, with Michelle emphasizing that despite the company's massive scale and success, "we're just getting started." (03:03) The discussion covers the challenges of scaling leadership, managing first-generation wealth, and navigating the intersection of AI and internet infrastructure. Michelle shares insights on maintaining authenticity while building a generational company, the importance of customer relationships in guiding strategic decisions, and how Cloudflare is addressing the evolving business model of the web in an AI-driven world. (40:54)
Michelle Zatlyn is the co-founder and President of Cloudflare, an $80 billion enterprise software company that secures and accelerates internet infrastructure for millions of customers worldwide. She met her co-founder Matthew Prince at Harvard Business School and has been with Cloudflare for its entire 15-year journey, helping build it from a startup to one of the most important internet infrastructure companies of our generation.
Joubin Mirzadegan is a partner at Kleiner Perkins and host of the Grit podcast. He focuses on exploring the personal and professional challenges of building history-making companies through in-depth conversations with successful entrepreneurs and leaders.
Michelle reveals a fundamental reality of company building: "You end up being at your companies longer than anyone you hire, and you outlive a lot of them." (08:34) This creates a unique dynamic where founders must live with decisions longer than the executives who make them. When talented leaders leave for CEO opportunities elsewhere, founders face the challenge of rebuilding teams while maintaining continuity. The lesson here is that founders need to develop resilience around turnover and not take departures personally, while also building systems that can survive leadership changes.
Michelle emphasizes that "spending time with your customers solves all problems because they tell you exactly what you need to be focused on." (15:05) In a world where leaders have countless competing priorities and demands, customer conversations provide crystal clear direction on what actually matters. This isn't just about gathering feedback—it's about using customer insights as a North Star for making better prioritization decisions across the entire organization, from engineering to marketing to product development.
Michelle advocates for nine hours of sleep as a business strategy, noting "sleep is the greatest drug of all" and comparing herself to United Airlines CEO who gets 8.5 hours nightly and Roger Federer who gets 12 hours. (16:03) She challenges the Silicon Valley culture that views sleep as weakness, instead framing it as a superpower that enables better decision-making and performance. This approach requires saying no to more evening events and creating space in your calendar, but results in significantly improved cognitive function and leadership effectiveness.
Michelle reflects on Cloudflare's early days when they "used to poo poo sales" and were enamored with their technology patents and global network. (53:56) She learned that "cool technology is absolutely cool, but you know what's even cooler? A great business model." The realization that companies get measured on revenue growth and gross margins, not technical superiority, fundamentally shifted their approach. This insight is crucial for technical founders who often prioritize engineering excellence over commercial viability.
Drawing from Harvard Business School lessons about not losing touch with reality as success compounds, Michelle discusses the challenge of avoiding the trappings that come with building an $80 billion company. (33:22) She emphasizes the importance of maintaining perspective and making conscious choices about lifestyle inflation, from personal assistants to private jets. The key is regularly evaluating what truly adds value versus what might disconnect you from the reality of your customers and team members.