The Wisdom Wall

“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.”

“Every successful outcome is led by a founder who is deeply impatient, really impatient.”

“The cure to politics is not to lecture people about being apolitical. It's to make sure the team has too much to do.”

“I'm friends with many CEOs who I've, you know, met over the years of having been one and then doing this job, and the folks who are really into the coaching and really into the touchy-feely stuff for themselves on the balance just have not performed as well as, as executives.”

“If you ask someone for relevant experience, then if they have some first advantage is that like you get to integrate their experience into your context, as opposed to trying to give them a bunch of context so that they can chew the cud for you and give you the advice far more effective to just get their relevant…”

“All alpha, all outperformance relative to the index comes from anti-patterns. Patterns are the things people do over and over again... none of it is predictive of success. It's the anti-pattern.”

“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.”

“everybody who starts a company is almost definitionally narcissistic and sort of believes that they are not subject to the statistics.”

“The third time you start the company, you're like, fuck that. Like that doesn't matter. What matters is I got to get the right product into the hands of the customer immediately. And I've got to test it in market and I've got to focus on sales and win rates. And I've got to drive the team super hard. And some people…”

“What if I look like an asshole is a fundamentally egomaniacal question. It's a terrible question to ask. The right question to ask is what's it going to take to win?”

“I find that executives need to deliberately oversteer in the direction they want, even to the point of it being a little crazy, but it's because they are the sole tension on the line of tighter constraints, higher bars, harder, you know, harder standards versus the army of folks who are inadvertently, not in any…”

“Like, the vast majority of executive decisions are coin tosses.”

“Hiring managers should not ask someone else who they should hire. They should simply ask for objective inputs to the decision, and then they can make the decision themselves.”

“I think they're fucking filled with happiness and enjoyment and energy and also tortured by the fear of failure and by whatever demons drive them or whatever passion drives them. Like there's this awesome Jekyll and Hyde yin yang You know, dynamic to what it's like.”

“Clear thinkers don't have to be that smart. They just have to be experienced, or they have to have lots of at-bats on a given topic until they've rounded out their understanding of a system. They might not understand why something is the way it is, but they darn well know what it is.”

“Oh my God, yes, you can have too many first principles thinkers because they have a tendency to over-engineer things. Not so much about having too many first principles thinkers as it is having too many people doing first principles thought. There's only so many times you have to solve a problem. There's only so many…”

“the difference between a really effective executive and an executive that's more ho-hum, I think, is that the more effective executive Fights the entropy, like, holds the bar high. Tries to make things happen more quickly, even though it's exhausting.”

“like the hallmark of good executive collaboration is sort of seeing lots of blind passes, where you just toss the ball generally in the direction of the executive who you didn't even look over to see was there, but you kind of know they're there, and they take it, and they run with it, and they execute on it.”

“The interview is the metadata. I don't care what topic we're talking about. I'm studying the way you think. I'm studying how you communicate. I'm studying how you respond to challenges and pressure.”

“As an executive, you're constantly thinking about inputs as a means by which to achieve desired outputs. Where I think a lot of people mess up is that they over rotate on talking about the outputs. Just operationally speaking, no soccer coach ever gets up in front of the team and screams about the specific score. But…”

“one of our nine leadership principles at Rippling is that Rippling leaders go and see. And what go and see means is that you don't live in the dashboard. And in particular, like when the anecdotes disagree with the data, you got a problem. You go and see, which might take the form of reading support tickets. It might…”

“The roving bottleneck is the thing that's holding you up from achieving the next unlock from two to 20,000 employees. You're currently working on the thing you think is most holding you back from achieving what you want to achieve. And the minute you solve it, it uncovers the next thing that's holding you back.”