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“Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth

Run the Numbers

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Navigating the Evolving Software Industry Landscape

The chapter explores the evolving dynamics of the software industry, comparing different eras in infrastructure, market conditions, and investor sentiments. It discusses the challenges and uncertainties faced by companies amidst high valuations, loose growth strategies, and AI advancements. The conversation reflects on the shift from early SaaS days with significant capital outlays to the current low barrier to entry facilitated by cloud services.

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