In this episode from February 2017, a16z co-founder Ben Horowitz and Jason Rosenthal, former Lytro CEO (now Vice President, Subscription Services, at Google) share stories and lessons learned from doing whatever they could to help their companies survive in hard times, including making and living through major pivots, selling new products before they were ready, figuring out financing with market and industry headwinds against them, and more. From their days together at LoudCloud to Jason’s experience at Lytro, and beyond, a common theme emerges: a CEO’s job is lonely in these moments and the hardest thing about a big pivot or change might be in finding the courage to make the decision in the first place.

Gross margins–which are essentially a company’s revenue from products and services minus the costs to deliver those products and services to customers–are one of the most important financial metrics for any startup and growing business. And yet, figuring out what goes into the “cost” for delivering products and services is not as simple as it may sound, particularly for high-growth software businesses that might use emerging business models or be leveraging new technology.  In this episode from June 2020, a16z general partners Martin Casado, David George, and Sarah Wang talk all things gross margins, from early to late stage. Why do gross margins matter? When do they matter during a company’s growth? And how do you use them to plan for the future? The conversation ranges from the nuances of and strategy for calculating margins with things like cloud costs, freemium users, or implementation costs, to the impact margins can have on valuations.