CEO

“Executive chairman means something very different at every company, just like CEO means something different at every company, and every company based on its stage of business, but I would say executive chairman is even more amorphous or non-standard.”

“Once you're at a hundred, you're never going to have more people reporting to you. It's not like the CEO of a 10,000 person company has more than five to seven people reporting to him or her.”

“CEOs tend to make is they don't invest long-term. They have one EA for a couple of years and then another one for a couple of years. These relationships compound over time. You want to invest for a decade plus.”

“Most CEOs And founders are actually pretty mediocre delegators. when it comes to working with an assistant we've worked with, you know, a thousand plus at Athena and some of the best YC Sequoia back companies, and most founders never graduate beyond the kind …”

“As the leader, sometimes it is important that maybe the team's a little bit less productive for your benefit, because you're ultimately the only person who can see everything that's happening and you're ultimately making most of the decisions. Right. And so it…”

“The warning I give to people is before you do that, let's actually start building in actual joy into your day to day, because I have had the experience of CEOs that I coach effectively turning off their fear. And then going, yeah, I don't want to run this comp…”

“Finding content market fit is priority number one when you start creating content. Everyone talks about finding product market fit as being the first job of a CEO in the startup world. And I think finding content market fit is the first job of a media company,…”

“Anytime you're doing something net new, you can assume that you're going to be mediocre at it because you have a lot of blind spots. And so, like, the first time you're a CEO, the first time you're a manager, the first time you do any job, the first time you h…”

“I have to think through this TRM thing for people, because if the main task of the business, they're lower medium on, it's never going to work. Right. Adrian was really high on recruiting people from the Philippines. Like I did not, I never, I detected it goin…”

“I think founders will be really honest with other founders. So don't be afraid to, you know, you're thinking about taking a term sheet from an investor. Look at, you know, all the other people they're on the board with and just reach out to the CEOs of those c…”

“I think that the CEO, unless they're not a product person, should think of themselves as a chief product officer, and they should be involved in the product.”

“The single author approach usually fails because the resulting words are often disconnected from the reality of how the employees as a whole experience the company.”

“Reaching the point of having a lot of unscheduled think time is perhaps the clearest sign of success for a phase two CEO. It suggests that you've hired a leadership team, delegated the day-to-day activities to them, and codified mission, strategy, and metrics …”