Executive

“It gives you a level of resilience that nobody you ever hire is ever going to have.”

“There's also another layer to this, which is as you go down in seniority, you're less likely to recommend your role. So execs, VPs, maybe even directors are sort of more likely to recommend their role than people who are crises.”

“I think it's 10 X easier for the CEO to break glass than an executive. And 10 X easier for an executive than an employee.”

“Average holding time of stocks is like dramatically down. Lifespan of companies is dramatically down. Average tenure of executives is dramatically down.”

“If you're not using the technology yourself at least 10% of your time, then you're in the business of listening to other people tell you things that you don't know if it's true or not.”

“Executives love creating fake legibility for themselves because we don't like noise as humans, right? We want the signal, but there's often less signal in it than one might think.”

“I would start to think of the top of the tree and a lot of leaders and a lot of executives are bottlenecks for their entire organization. A lot of what they're doing, 70% of what they're doing should be things that Are pre-standard in industry.”

“You know, a lot of people that have climbed really high in their career are just great imitators. They just take a playbook that they saw somewhere. They don't always fully understand it. They don't always know how to change it for changing circumstances, but …”

“If you want to make sure that you have the right founder, you ask tough questions in the interview process. Right? And you sometimes, ah, ask questions where it might be irritating to them, and then you see how they react to it. Right. And then you get a sense…”

“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.”

“And what I learned through that process is that people completely misunderstand how executives make decisions. What is going on in the heads, in the calendars, in the incentive structures of executives. And instead of really understanding where that exec or st…”

“If you don't respect that person, if you don't believe they know something you don't, you need to quit. You need to go work somewhere else.”

“Execs are so good at seeming certain. They say things in an authoritative way, with confidence, with surety, because so much of their work is having to make those ultra fast decisions with little information.”

“Because the moment you go off over 60 seconds, you've lost them.”

“What I can't get again is the time for discussion with that group and the safer that they feel in that discussion and the more that they think that you've understood what is the most Sort of spicy or controversial. That's where you get to the good stuff and yo…”

“AI is going to get blamed. Even if there's an, even if like tariffs drive high unemployment, like if people lose their jobs, like AI is going to be a scapegoat and it's going to be used both by executives.”

“Executives at my companies, they don't cuss emotionally. So if you need to take a minute and stand outside until you can emotionally re-regulate, that's perfectly fine, and come back in. But we don't do angry cussing at the executive level.”

“If he's doing a bad job, like no job is better than a bad job.”

“And getting stuck in procurement is usually because you're not speaking to a senior enough person and they don't know how to navigate it, which is why, like, that executive needs to be involved. Because as soon as the executive picks up a phone and tries to ge…”

“Well, I mean, my, one thing I would say just specifically to the truism you just said, is I really just think it is, like, Bullshit. And like, basically every executive is like on one hand being like, how can I use AI in my company? On the other hand is saying…”

“I've always I think my, like, the conventional wisdom of everything is to go out and hire somebody, like, really experienced that makes you feel really good from a really good background that's at a successful company. And I found, like, that playbook is just …”

“Either you can dispute them, but first validate it. Don't start with the disputing. First validate and say, okay, yeah, of course I'm having all these negative thoughts because I got a tough job, for example. I have a big job, there's a lot of pressure, and I'…”

“Don't try and fix them. They can't be fixed. It's not going to happen.”

“Executives don't waste time on throat clearing or setting up a big runway before they get to the takeoff. By giving the headline first, you frame the conversation and make people lean in instead of tune out.”

“If I have the ideas about what your department should do next, if I, you know, am kind of pushing you to kind of move your organization forward, then that's no leverage. What's leverage is if you're telling me what you should do and how you can push the compan…”

“I'm just talking about with other executives and things like that. They're transactional. And people you're on the other side of the fence from, people that run companies, they're not real. They're usury.”

“If anyone on your executive team, or honestly, I know this is tough love, anyone on your team that by June, is not deeply curious, like is not pretending to use chat GPT once a week to get recipes... By June, if not, if July won, I would like just start taking…”

“If you're truly on a track to become like a, an executive someday or found your own company and make it successful, you will find that the compensation is so much backloaded. That you would make 90% of your compensation in the last five years of your career.”

“It is much better To frame whatever it is you want to talk to them about or your recommendation under an existing umbrella of what they already care about, of values they already have, of ways that they already think the business should be run.”

“I think that many pairings of execs and founders that work really well are when execs recognize that their founder can be spiky in different ways that might not really make sense, that they are really good at certain things and not as good as at other things. …”

“It takes a year for anybody to figure out the company, a year to actually take bets, and year three to really deliver value”

“The only reason you can be good at your job as an executive in the entertainment business is to really not look at human beings as humans. You have to look at them as objects.”

“And I just don't think that you're going to be able to get enough reps to actually get good at executive communication if you are only doing it with executives. Because many of us only present to execs once a month, right? Or a couple times a quarter. And that…”

“Like the funny thing about all these things, like when you are interviewing someone, inevitably they were good for someone somewhere. Otherwise you probably wouldn't be interviewing them, but it's the hard part is finding the right fit.”

“I personally really worry about the, like, the two-year stints, sort of, like, multiple, like, two-year stints. Like, it just actually isn't enough time to show that you've done anything significant, I think, as a leader. So, like, this is a gross generalizati…”

“But a leader who's only been at one other company, I think I'd always have a few questions about because they're going to be very tempted to copy paste everything that they did.”

“How many people moved to the next company that you worked at, that you worked with before? I think it's always a really, really good sign.”

“Per your point, if the, if you just have to assume that the distribution of failures is, like, pretty much the same across the org, I think it's always a pretty good sign if people have fired a lot. It's only because, like, they're gonna have to in whatever jo…”

“I think that oftentimes the quote is hire great people and get out of their way. I think that's a terrible idea. I actually think it's much better to hire people actually in your zone of genius.”

“One, I think you need really good executives and you don't want to do the founder mode thing unless something's broken. You know, like you kind of want, cause you can't do it everywhere. Like you need people to help you run the company and like, and so you wan…”

“Actually interviewing execs and very sort of more senior experienced people is really good for getting a feel for whether I would enjoy working with them. Can we brainstorm? Can we debate? Do I enjoy, you know, being with them? But I rarely find that folks lik…”

“A common tactic that folks employ is to only talk about the really positive things. Only talk about all the reasons that this would be an exciting investment, like this outdoes all the others, and more. But chances are, if you're trying to go ahead and only ta…”

“Don't hire the jaded. The one literally four minutes in your interview, they're telling you how the CEO or the VC screwed them over... Don't hire them. They're going to think the same thing of you about three weeks in.”

“Most of these, like, very senior jobs in tech companies, you get paid a ton of money, and they're relatively easy, and after a certain level of tenure, you're never gonna get fired”

“What I've seen works, the execs that are really good have come in, found the really good key talent, but then brought in talent that they've worked with before to fill the gaps. And that's been a sign of a really good executive.”

“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…”

“Your executives, the team you have around you, like they, over time, They start to, like, filter information too much, and they can give you, like, an overly rosy or, like, false, like, positive view of what's actually happening in your company”

“You get pushed often by investors to hire executives or to scale the team, or we need, you know, We need, we re you raise all this money. You got to spend it. You know, we got to, you got to show you're serious about growth and building a world-class organizat…”

“In the highest reaches of business, it's not uncommon to find leaders who display followership akin to that of teenagers.”

“If you're considering investing in social to just do corporate channels and not think about executives, you're really leaving like a lot on the table. Like, corporate channels. It's very hard to build a, it's very hard to build a following to get someone to fo…”

“When you're hiring super senior whip smart executives to work for you, They don't want to be told what to do. They want to have a grand vision that they're excited about. They want maybe some goals to latch onto and help possibly with a strategy to get there a…”

“When companies hire executives, What are they looking for in executive? They typically go, ah, judgment and experience. They're not like they can read an Excel spreadsheet. That's not the thing that matters. Like anyone can read that, or anyone can read a char…”

“If in a senior leadership meeting, you appear defensive. When one of your executives is challenging an idea you have, you can assume that you are now incentivizing other leaders to be silent and hold back their opinions.”

“Your job as an executive is not to be loved. It's to help your people achieve more than what they believe it was possible.”

“This is a mistake a lot of executives do because they want to be loved. They want to be sometimes soft or too nice. You know, they don't want to stretch you.”

“The most valuable thing as an executive you can do is educate like the other execs on how engineering works, not kind of protecting engineering from visibility from anyone else.”

“And this is like one of the, to me, most predictive traits for whether an executive will last more than a year at a company. It's where they come in and they start with, Hey, can I, how can I change myself to fit versus how can I force my entire organization t…”

“But when you present to execs, you should start with the conclusion. And then, if they already agree with you, stop presenting. Like, there's no reason to keep presenting.”

“So like almost always when you get these like really like offhand random ideas from executives, there's a kernel of insight there that you can extract by kind of asking more, more detailed questions to them.”

“I think that the best folks presenting to executives start super zoomed out and then zoom in to their specific problem over the course of like 30 seconds.”