CEO

“I still think no matter who you are as a CEO, the goal is to build a healthy organization that could function without you, and I think that's always the goal, and then it becomes a matter of where do you spend your incremental time.”

“I've found that there are CEOs who are particularly good at something that become, like, a go-to default on, like, a topic where I think I've got, like, a lot to learn from them on. So there might be somebody who's, like, incredibly good at, like, managing exe…”

“The more senior you are in the company, the more you should be working on the machine rather than in the machine. Obviously, we're all going to be part of the machine as well, but generally speaking, you know, your company gets past a certain size, and as the …”

“Typically when a CEO of a 500 person company feels their CTO is, is struggling, they're probably running into like one of two different things. Either the individual CTO is like causing friction with other people on the team. For some reason, like their peers,…”

“Anything else is going to get like a kind of consensus view, but like you don't need a consensus view on executive performance. You as a CEO need to have like a conviction view on like whether it's actually good or not.”

“If they were enforced in a board meeting of like, not only do we want to see your Engineering status and whatever, but we want to hear about your customer discovery journey or your validation journey and tell us about the MVPs you're building and show it to us…”

“They were world-class number twos and almost never are world-class number ones.”

“I am a big fan of, say, the CS organization reporting right into the CEO, because in those cases, the CEO is really close to the customer experience, no matter what phase the business is in, super early or operating at scale.”

“The CEO job, the most successful CEOs act with impunity in the work environment in a way that number one, a good CEO doesn't really think about it. And number two, a good second in command does think about that and enable it.”

“One thing that's really clear about successful CEOs is that they don't ever really worry about the downside of their strengths. Like they just go almost blindly, just like at the business, applying their instincts.”

“I noticed in all of the companies I worked at that actually the ICs and the high level leadership was, I think more philosophically aligned because I think CEOs and a lot of the high level leadership, they just want to see things happening. They want to see ou…”

“I think the most important thing as a CEO, especially, is to be, like, a leveling function. Actually, like, there's various parts to this, right? As an entrepreneur in general, like, yeah, either shit is amazing or shit is, like, awful, right? Like, it's, like…”

“I think CEOs need to know, you know, about 80% of what their executives know about their function, I think, over time. So really kind of learn that discipline. Not enough to be good Add it, but enough to be, to know what good is and know if it's going well.”