The CEO of No

A lot of people might be surprised by how empty my calendar is. Many CEOs seem to believe they have to wear themselves out working 9 to 9 — they torture themselves, basically — but I think you can run a large company in two to three hours a day.

Almost any CEO can get to that point, but it’s essential to have the right executive team, and it relies ... See more

Today, we’re announcing a huge change at Tiny. Entrepreneurship is just delegation taken to the extreme. At first, you do it all. Badly and all at once. It sucks. Because you suck. Then you read a book and have a lightbulb moment: You realize that you can hire someone to do the things you’re bad at. It feels like someone has given you the che... See more

Execute based on your own plan and not in reaction to others. Agency and ownership rule the day, and this is why “Send email to X” is stronger than “Send reply to Y” — the best work does not happen in reaction to what others do. Just build your own plan based on your goals and the information you have at hand, and don’t be afraid to update it as yo... See more

Early on, when we were scaling Box at 20 or 30 employees, we came to this question. And I asked myself, “Do I look like these other CEOs that have scaled big companies?” A lot of times it didn’t feel like I was like them. I focus on a very different set of things. I don’t really like all the stuff that they like to do. But I ended up realizing that

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The trick to being effective at this is that you have to get really good at saying no and just not doing things. There are a lot of things that are urgent but not important. The hard part of being a good CEO is that you have to be willing to let some things fall apart. You don’t have enough time to do everything well. And in practice, what that mea

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If the CEO disconnects from the product, that’s usually bad. And that is something that you see happen to varying degrees as a company scales. There are a lot of CEOs that say, “Well, I want to just go think about strategy all the time. I’m really tired of managing people.” Because managing people is hard. And so a lot of CEOs have tried a structur

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