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Cloud computing was once highly controversial
“They refused to accept that the cloud business model deserved to exist. This idea of forward cost and back loading revenue made no sense to most folks, and it was highly controversial for many years. We did believe that the answer was there, that fundamentally it was better for customers and that the business model would follow.”
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Seek out the hardest customers first
“It’s somewhat counterintuitive, but you actually wanna seek out the hardest, smartest customers and have them beat the crap out of you. Because others will follow. Their peers in the industry know how good they are and learn from them. So take on the hard first and work with them as design partners go through it.”
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Maintain capital buffers for macro cycles
“Fortunately, having been in venture before, I knew enough to raise early and have buffer, so we never had a true extinction level event. I think entrepreneurs need to expect to go through several cycles in your journey, and you need to reserve enough flexibility, capital, etcetera, so that the macro can't sync your ship.”
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Founders should design their own roles
“As a founding CEO, you’ve got the luxury of designing your exec team. Do it however you want. What things do you enjoy doing? What are you best at? What’s gonna give you energy and what’s gonna give you most impact? And then we’ll hire everyone around you.”
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Balance intense conviction with coachability
“I think the best leaders are the ones who are brilliant, who are convicted, and yet they’re reaching outbound when intensity mounts. They need more input, and they seek it out, and then they make a more informed decision. And I think that's the mark of a mature, confident leader who's going to work through problems and wrong answers to get to the best answers.”