CEO

“When you flip the table and you become the VC and a board member and a representative of the money you've invested, your fingers really need to stay out. Your nose is in, and you're constantly smelling for things that don't smell right, and you're letting the …”

“I think it really comes down to trusting your instincts. You know, you have instincts, and you, above everyone else in the company, kind of represent the collective wisdom of the company, and knowledge of the company, so you're the most informed overall, and i…”

“No, I would say, you know, in impact the most challenging aspect of the, being the CEO is figuring out timing of important decisions.”

“Most of these entrepreneurs, CEOs who are likely to achieve these outlier performances come with big egos, and that, that is an important ingredient, but it's one that the really successful CEOs are capable of kind of checking at the door when it's necessary, …”

“As a board member, investor representative where you have to watch the CEO and the organization make mistakes, and know that that's part of the learning process.”

“I think there's a gene that some people have and some people don't, but I think that, you know, that's the starting place, and I think that the CEOs that achieve outlier performance are the ones who have the gene and develop that gene and really build these in…”

“As a CEO, you know, you deal with all sorts of things. You're basically the chief problem solver, and that's from, you know, solving why the toilets in the bathroom are always clogging to, you know, when is the right time to sell the company and everything in …”

“Storytelling is sales, storytelling is fundraising, storytelling is recruiting. Those are the things, the key things that a great CEO does, and you really have to do that well.”

“I think on the entrepreneur side, I almost, I often tell people that one of the most common traits in successful CEOs and successful entrepreneurs is revisionist history.”

“When you're the CEO of the company, you're the guy who's making the last decision, right? Like, no one can just everyone can blame you for everything, and you can't blame anyone, right?”

“I'm fully aware that the CEO who's been working 60 plus hours a week in a specific sector for several years knows a lot more about that sector than me as a VC board member who, I mean, really can rarely spend more than five hours a week on a specific company a…”

“When you're running a company, you basically spend about five percent of your time actually focusing on the things that you would deem important, and about 95% of the time working on things like, Fundraising and HR and hiring and all the things that, you know,…”

“Making sure that you have some bandwidth as a CEO to keep your head above the water to sort of see what's going on and really understand what you could try doing and knowing that it is part of your job to go out there and think of very strategic ideas that peo…”

“Most CEOs can pull off sort of two things in their life. So, you know, maybe they have a family and they have a job, you know, you can probably pull off that, you know, certainly when I was CEO, I felt like I had a family and I had my job and didn't really hav…”

“I think where you step in is in the areas in between these, you know, when things contradict, when there are topics that are sort of owned by multiple departments at the same time, or where you just know you have a weak team.”

“As a CEO role, your kind of ultimate job is to hire yourself out of a job in many ways”

“He needs to feel confident that he can put them in front of me, and I'm going to be able to talk with a basic knowledge about what that developer's been doing in his past history. Ultimately, as CEO, I need to be able to attract talent right the way across the…”

“I think the best board member is like your outside co-founder. I mean, I think he's your consigliere. Who you feel like you can call when you have so many issues that you have as a CEO that really you almost can't talk to your team about, and you know that tha…”

“We can often think about the CEO job as the top of the ladder and the glamour job. But I think everyone just needs to understand it's a job like any other. It's very much akin to, you know, the engineer who's the best engineer on the team, but might not make t…”

“Being a CEO, the things that make you a very good leader have nothing to do with the things that make you very good at finding and choosing investments.”

“I think a great CEO is someone who, over the long period of time, is able to continue to reinvent their business. Mark Leslie wrote a tremendous article about this that he published on the first round, excuse me, the first round review on the importance of rei…”

“All, all successful CEOs I know of are both skewed or specialized in one area, but also extreme generalists.”

“The only time you take preemptive action, and this is the CEO not listening, I'll come back to the board separately, you take preemptive action when it's a fatal error. What I tell my CEOs is, are you making a mistake or a fatal error? If you're making a mista…”

“As a board member, you have four jobs, and the definition of a job is if you don't do it doesn't get done. The four jobs are you hire and fire the CEO. You finance the company, because if the insiders don't finance the company, new investors won't. You agree w…”

“My job as CEO changes every three months. And so does the way I go about the job. What used to work for me two or three years ago does not work for me now.”

“The best CEOs, even when things are going incredibly well, are constantly making upgrades and changes to their management team.”

“Whenever you try to tell a CEO, Hey, you have to do this. The natural reaction is to get defensive and Hey, you don't know my business. You're coming in here once every two or three months. How do you know it better than I do? And the answer is we don't. So th…”

“Because if I would work for the CEO, then I know we can recruit an amazing team under him, and he's already built the bones of a great team, and whatever happens, I'm with the company until the end of time, and at my gut, I feel like we can't lose.”

“And I think the other sort of unspoken benefit of CFOs is that they're really the only other function that can look across the entire company in an unbiased way and help sort of measure performance and help advise the CEO on how to invest the company's resourc…”

“But again, I think it's almost the way the CEO or the founding team communicates. It's a great predictor of success. And again, I think being a good communicator, it's obvious, but the people that are concise and size and they come to a meeting and they're lik…”

“So my rule of thumb is only schedule 50% of your calendar. Don't schedule 40 hours a week of meetings.”

“As a CEO, as your company grows and scales, your job becomes more about capital allocation and where you're placing your bets, right?”

“If you're not spending 10% of your salary every year in your company on your own personal growth and development, like you're literally suboptimizing the company.”

“I think it's dangerous if you start empathizing too much with the problems that your team is trying to solve, because that will just hijack your thinking, and it's just going to create stress.”

“One of the biggest problems with internal capital allocation inside a company is, Very rarely do CEOs have access to true opportunity cost-based prices. And the market's really good at that. The market's really good at saying, well, if you're going to use my f…”

“You can't much help them when they fail, but how do you help them scale when they succeed?”

“I think probably the most important quality and the common theme across all of them is just their dogged persistence. They're going to make a dent in the universe, no matter the hurdles they have to lead.”

“As an entrepreneur and a CEO, you have to be able to compartmentalize. Otherwise, you know, you go insane because there are always 50 fires you can be thinking about fighting and worrying about. You have to choose what you're going to focus on. Focus on those …”

“A lot of CEOs and entrepreneurs are given bad advice by investors that are based on success biases of other things they've invested in, They're given bad advice by their CEOs who are giving their advice based on the success biases of their own companies.”

“I think that, you know, great investors are helpful when you ask them to be helpful and need them to be helpful, and they dig in and roll up their sleeves with things like recruiting, particularly on areas like recruiting or another area where a CEO may need h…”

“I mean, I've changed probably 15 CEOs in my life.”

“There's no difference between the CEO's goals and the company goals, and if they really are just lagging behind dramatically, then it's just not something you can sustain.”

“The role of the CEO kind of adapts to that complexity and really shifts, and really it consolidates down to four or five different areas. The first is hiring executives and talent. The second is really resource allocation, so determining where capital should g…”

“You can't hire professional managers to really change the focus of a business. My biggest lesson was when you have an incredibly important strategic initiative, the CEO needs to clear everything off their plate and make it happen.”

“I think what I've seen fail is People who are like, okay, I want to bring in a CEO, but I don't want to give up anything. I want to still be involved with all aspects of the business. And you're like, okay, so in effect, you still want to be CEO. You just want…”

“You never really want any one person on the board to be able to block or hold up the board on a decision, and frankly, it's way better to have the CEO driving the board than the other way around.”

“The top jobs require lots of energy and time, and that doesn't mean you can't find moments and have a great family, and I want you to do that, but it's really hard. So I think people that dream about having the best jobs in the world and the best work-life bal…”

“The biggest mistake that boards and CEOs can make is waiting too long sometimes to make changes.”

“There's three core characteristics, three core elements for the CEO. I certainly think one of them is about the people and making sure that you continue to scale the team around you. Absolutely. And by the way, that gets hard because you have to do it quite of…”

“When things are sharply going wrong, it's actually the part of the job that's, in many ways, the simplest, because you know what you have to do, and then you just do it. And you have like, you have one major objective. The objective is clear. And even if it's …”

“If you're backing the CEO and he's running the company, It is your job to be behind the CEO. If at some point you make a decision to remove the CEO, make a decision to remove the CEO. What you're not allowed to do is be like a fucking carpenter ant that's like…”

“One of the things I truly found out is that, like, being a CEO is a job that adapts to you, and not that you adapt to the job.”

“I always recognized, particularly as a leader, particularly as the CEO, that I had to be A little bit of a shock absorber for the company, and when everybody was talking about how great they were, remind them that super competitive market, and remind them that…”

“Because my job as a founder, and I think my job as a CEO over time, is to make sure that for as close to a hundred percent of the team as possible, their career goals, their professional development objectives over the next six months, 12 months, 24 months, fi…”

“Are the founders genuinely asking for the help and the partnership and the change has been initiated by them? Usually that is a very healthy sign that you can add a lot of value and that it's going to be a really positive integration.”

“I think it's incumbent on board members to really recognize when there are just little bits of conflict on the board or little bits of Differences in opinion. I won't even say conflict, and we should be proactively trying to help the CEO resolve those and get …”

“When I said we're there as a board to serve the CEO, I call that sort of one in the same as serving the company because the CEO is the ultimate leader of the company. Yes, you could say hierarchically, I guess the CEO works for the board, but the CEO is guidin…”

“Every M&A deal at Google needs to be approved ultimately by our CEO, and it needs an executive sponsor, and an executive sponsor is one of the CEO's direct reports that runs a product area at Google.”

“Anytime I have an idea that pops into my head during a boardroom, I'll write it down. And then I'll ask myself, does this need to be discussed right now? Is there a benefit of this being discussed with the other board members right now? Or is that something I …”

“Because what I realized is for a CEO, if you can help them build stronger relationships, and if you can help the executives be better at what they do, that helps the CEOs, and that helps the company. So I make it a priority to give the CEO leverage by helping …”

“I and my partners at Foundry like to carry around Sort of one decision we have to make at a board level. And we talk about it as the only decision we want to make is whether or not we support the CEO. And if we support her, our job is to work for her.”

“I honestly think it's honesty and that there is no way that any founder who has not done this three or four times before can be a competent CEO scaling from seed to C and D and eventually IPO. And I think step one is just admitting that you need to hire and wo…”

“Well, look, I think in order to accomplish that, you really have to be the board member that controls the board. So if you're like a board member and you're the third strongest person on the board and you have a trust relationship with the CEO, that's not goin…”

“Just because you've been a CEO doesn't mean you know how to teach somebody how to be a CEO.”

“The early days, like the sort of one to 30 or 40 years Employees and the, you know, zero to one to two million as a CEO, you're a player coach. So you're doing a lot of jobs as an IC, but you're also managing maybe some frontline folks and you have CEO stuff t…”

“As a CEO, if you're really going to recruit, you've got to get on a plane. You've got to be willing to get on a plane for almost everything.”

“And usually it's not strategic thinking because you have very little information about the company. They're at the company, 30 days a month, 12 hours a day. They have so much more information than you do. But what you have that they don't is you have a network…”

“As a first-time founder, especially as you're transitioning from this hunting for product market fit stage to really starting to scale and nurture letting go of product and finding somebody who you feel confident can fill those shoes is incredibly scary as a C…”

“As a CEO, your first chapter is all about steering the company to find product market fit. The second chapter is about your product is no longer the product of the company. It's really the product becomes the organization and the executive team and really maki…”

“As the CEO, you set the pace for the organization and every six max, 12 months, you have to fully reinvent yourself because the organization is evolving so quickly, right? As you grow headcount, as your challenges evolve, as your executive team evolves, you ha…”

“So I tell CEOs, curate your investors, but curate your board.”

“If the CEO doesn't believe in their product enough to sell it, then nobody else is either.”

“So if I looked at the CEO or founder's time, 99% of their time is spent on operational issues.”

“One of the things I've also learned is that on a board, even when you own the entire company, you can't dictate what they need to do. You can only guide and you can set guide rails. And so at the end of the day, you're ultimately deciding, is this the right pe…”

“Well, I think the biggest thing to remember is that you're not the CEO's friend, that you're not there to be a buddy. You're there to actually ask probing questions. And to rub their nose in the consequences of what could go wrong.”

“In the businesses that we own, I'm never going to let a CEO make a sink the boat decision, right? But if it's a two-way door, if it's something where, look, I think this business model idea is hokey, but they've got it in their head as the greatest idea ever. …”

“The board's role, I think, is, besides hiring and firing the CEO, is validating strategic direction for the company And providing some insights to the CEO that they might be missing.”

“When you're the CEO, there's not a ton of time for on the job training. You really need to understand what you have in front of you and what you're working with. And that includes having some wherewithal and understanding of what each function is meant to deli…”

“COO is one of those roles where there's not like a single COO. It's very much a custom mold to what the CEO is and what the founder is and finding someone whose strengths are the founder's weaknesses and vice versa, more so than it is just Hire a COO off the s…”

“I was always struck with how much detail he has around the functionings of a business. Like he could explain in detail how the planning group of The finance team versus the accounting group thinks, and the challenges of having someone who's doing one role doin…”

“There's really only two control points you can do, which is hire and fire the CEO. Everything else you have influence over, but that's the only real control points that you have.”

“Leverage is helping a founder or CEO get something done faster than they would have without you. And overhead is making them get it done slower than without you.”

“A lot of people like to make introductions to CEOs and CEOs oftentimes will have to take them because they feel obliged to do that, but the introductions don't lead anywhere.”

“And Jeff is completely right. It is not a democracy and it's really up to the CEO. And then ultimately the board who controls who the CEO is.”

“As CEO, you always have the most context, more context than your board has.”

“I think if you're very conflict averse, if that's a personality trait of yours, you're just too nice. That's a really important characteristic of a CEO is that they should be able to deliver that. If you can't do that, how are you going to make all the difficu…”

“I think there's table stakes and there's your spikes or strengths, right? So whatever your job is, there's table stakes good enough. I'm not a project manager by nature. It's not What I'm great at. But to be an effective CEO, there's a table stakes level of pr…”

“I think the real issue is in those cases, they've often siloized it or given it as a responsibility to somebody else. When I think this is something that is about talent and about culture and something that the CEO really needs to own and drive.”

“To me, it has to be about like the product and making stuff. And most CEOs aren't involved with that anymore. They're involved with other things. They're involved with complicated things. They're involved with conflict. They're putting out fires all the time. …”

“As a CEO in general, you have to be the equalizer in chief, you know, so when things look great, you have to temper people's enthusiasm a little bit and say, hey, This looks great, but, you know, all these other things are still broken, we need to fix them. Wh…”

“If I look at all the board members I've seen in action, the number that are really adding value, really trusted partners of the CEO are in a small percentage. I think probably the, maybe the bulk are mostly harmless, or sometimes helpful, and they write checks…”

“I think a lot of CEOs feel that much more fear of failure than aspiration for success.”

“I always say to the CEO when they're bringing in board people, don't picture them today. Picture them on the worst day. Picture them, you've missed a quarter, an activist shows up, the technology doesn't work, your best person left. Picture how your board's go…”

“You want a board that is able to transfer their credibility, whether there is an investor or as an operator, to the leader, to the CEO, in the very worst day. And that's what a good board member should be able to do.”

“To lean in with curiosity, and then to not let it repeat, though. I think it's kind of like a stuck state, back to that other part, is if you just let them, like, keep asking every meaning, and you just don't hit it on the head, you're gonna be frustrated, the…”

“Brand mission, you know, kind of purpose of the company, the people of the company. And then really the third thing would really be, you know, kind of how we interface with our board. How are we Driving forward that conversation. You know, I can't put my, you …”

“The other critical thing is understanding which decisions only you can make as the CEO. Many other decisions can be delegated. Many other decisions can move down the ranks. There's certain decisions that Only you can make. And one of the reasons why this is im…”

“I see a mistake a lot of executives make, and this is outside of growth too, where they're like, they'll expect their manager or the CEO to like take care of their problems for them. And it's like, no, that's not what happens. Like you got to go solve those pr…”

“And for CEO, that one skill alone Can propel a company. If you can assess people infallibly, that is, you know, the propellant for many, many, many companies.”

“If you are a CEO, diversification should not be at all what you do. You should be a hundred percent concentrated on one thing”

“Most CEOs are far more, you know, timid than they should be based on what their role really is. And the reality is the CEO has enormous power, but most CEOs don't realize they have it and they don't exercise the full measure of the power that they've been hand…”

“No, we feel insecure and high anxiety all the time. I mean, I often tell CEOs, if you're feeling anxious, congratulations, because you passed the intelligence test. You should be anxious. People are trying to kill you. You know, you'll be insane if you weren't…”

“I'd say it's almost a red flag if the person you've just hired is not asking you for help as founder or CEO.”

“Those of us are one and a half hours open session, and then about 45 minutes closed session. So you, it's not five minutes you should do a closed session. You should do it for 45 minutes and then about 30 should be with the CEO and then 15 without the CEO to e…”

“We decided to run a test in Hyderabad, India, where we said, let's let riders request their first ride without putting a credit card number in. In fact, we were told by our CEO not to run that test because he felt so strongly against it, but we had so much con…”

“When I see both as an A plus and any traction at all, like any traction at all, I feel like I literally cannot lose money on that combination.”

“I think this is true, but I blame the CEOs for lowering the bar on hiring for VPs.”

“Going into the enterprise is a commitment for the entire company that starts with the CEO and that needs to take the entire, not just the go-to-market teams and sales teams, but the entire like marketing and engineering and product and the entire culture of th…”

“So I completely agree that the highest leverage activities you can do as a founder is hiring the best bench and C-suite and VPs you can. Setting the vision. That's only something you can do, you know, finding the values and the purpose of the company or missio…”

“If I were designing from first principles, I would say the head of growth reports to the CEO meets weekly and is flagging issues and also discussing potential, you know, strategy changes and approaches at a very high level.”

“Not all the time, but usually, you know, it's best for a CEO of an internet company to have been out of product, you know, or being a founder is almost the same thing.”

“I ask this of a lot of CEOs, male and female CEOs, and all of the male CEOs go straight to strength. This is what I'm amazing. I'm world class at this. Two minutes later, a minute over the one minute, they stop, and I go, and your weakness? Oh yeah, I forgot a…”

“If ever you're going to the votes and using your role as a board member to oust the CEO, something else is broken down along the way in the journey and the relationship you built with the founder and the rest of the board.”

“The mistakes that I see happen is that the CEO founder goes to hire for a skill set that is either at odds with what they really need, or they're not actually honest with themselves around the role that they want to continue to play within product. And so if y…”

“Honestly, I don't think that a lot of our jobs, including my job are like that hard.”

“I explicitly, I have a doc that says, like, working with me, and what, how do I see my job? And in it says, I try to make as few decisions as possible.”

“And your job as the CEO is actually to make sure that you go and practically ask them, ask all of your team members, how do they feel about the new hire? What is the value that the new hire is delivering already? How is the new hire helping them up level and d…”

“I'd say it's almost a red flag if the person you've just hired is not asking you for help as founder or CEO.”

“The methodology of the founder or the, like the, all powerful CEO, it's almost like creating this picture of someone that, you know, like, you know, hires everyone up until a thousand employees, which to me tells that, oh, you don't trust your people to hire p…”

“In my experience in sitting on boards, and I'm sad on many, no matter how hard you tried, you never really know what's going, my experience has been, you never really know what's going on inside of a company, so board members are entirely dependent on On the m…”

“Generally, that is a very dangerous place to be where the founders or the CEO of the company is not working on the most important problem for the company's success.”

“The mistakes that I see happen is that the CEO founder goes to hire for a skill set that Is either at odds with what they really need, or they're not actually honest with themselves around the role that they want to continue to play within product. And so if y…”

“Balancing capital and resources against short and long term is, is the hardest, the most important part of the job.”

“I think I think it's a heuristic by which. People can explain to themselves why certain people are great CEOs, but it's not the reason. It's not causal. It's correlated. I think the causal, causality runs by, I think the best CEOs are people who have a more co…”

“The biggest red flag for me would be on title where, you know, you're pretty clear on what you want. And they're like, well, I need to report to the CEO. And it's like, well, that's not available. Like you're not reporting to me. I'm sorry. Like I I'm interest…”

“The best companies have very, very simple explanations that, you know, it trickles down on the company. The CEO can articulate in one sentence, but the manager four rungs down also can articulate it. And that means that that manager knows how to go left when t…”

“A board member's job is not to come up with the strategy of the company. A board member's job is to ask the right questions that might, you know, engage the CEO and the executive team in, you know, slightly different conversations.”

“That, that, you know, a 10 or a hundred billion dollar company CEO will actually respond thoughtfully. More than many VCs, frankly, who's just saying, good job.”

“There are always going to be marquee organizations that are going to require a level of attention or connectivity to a company at that level, but if I'm holding myself accountable as a CRO, we will want to have executive sponsorship with all of our marquee org…”

“Allowing a committee to dictate a hiring decision is never good. At the end of the day, the hiring manager, the CEO in this case, needs to be empowered to make the decision, even if there isn't consensus among the hiring team.”

“What I've found is hard about that is that as, you know, a successful CEO, you will say something and everyone thinks, well, that, that must be right.”

“I would say really any time a CEO is not spending on their company, it's bad for the business. But that's true. If you're dating, it's true. If you're being a spouse, if you're parenting kids, if you're working out, You're spending time with friends. If you're…”

“It is actually, they're generally not happy when someone in the fund is like also a CEO, but they should be because that fund's going to end up doing so much better. You're going to get into better deals, et cetera.”

“If the thing you're doing on your list is something someone else in the company should be doing, you probably shouldn't be doing it. Because your focus as CEO should be on only on the things only you can do.”

“I think CEOs, founders like to blame other people for failures. Sales, sales is probably the first person to get the finger pointed at.”

“And your investors aren't involved enough in the day to day to really know. So they can give strategy advice, but they don't know how you're behaving in meetings.”

“I think there's a ton of challenges, and it's even worse for CEOs, because who in your company is going to give you really crisp, blunt feedback on what you did right and wrong?”

“Almost every other CEO I know, including ones who've been incredibly successful, probably procrastinates on that conversation a little too long.”

“When we were selling in the Australia, New Zealand market they had these new laws in place in Australia around if a job site accident led to a death at a construction site and a safety violation had been seen prior to that that wasn't Document it. The CEO of t…”

“I kind of think of it as the CEO is the chief capital allocator of the company.”

“When you're the CEO, you have a one percent impact on everything, but you have Almost nothing that you can actually point to as your own work product.”

“There's a point at which, you know, you can disagree behind closed doors, but once the path is defined, which is defined by the CEO, you've got to get behind it or you've got to leave. Frankly, like if you can't get behind the idea and you can't get behind the…”

“Well, one, CEOs should never be RVPs. They should never be the ones that are actually closing deals. That, that's my job. What they, CEOs should give the customer the confidence about our vision and what we are doing as a company.”

“But for many product builders, AI is something they delegate. I mean, it's like really delegated to the AI team or the engineering team. I think AI strategy starts from the CEO and makes its way down.”

“And I think that probably happens with CEOs of, or founders of all companies as they scale.”

“I think being honest as an, as a CEO and speaking to your employees like adults and not children is the way to get past it.”

“A CEO has three jobs. Set the strategy and vision for the firm, Recruit, retain the best talent, and hold the talent accountable.”

“I don't say 90% of what I think because of the backlash that would come from the one percent woke. I think every CEO that I speak to have on the show is the same.”

“In a successful company, there was at least one board member, and typically one board member, that's he or she are the first call for the CEO, and they're in the room whenever the big decisions, important decisions are being made.”

“The only thing on the CEO's mind right now is everyone running off in different directions, and not being able to kind of understand what kind of decisions we're making.”

“As someone was telling me recently, you know, the first time a CEO feels like, you know, something hasn't worked out, they should act on it. Because, like, if they have that impulse with, like, you know, all of the sort of importance on the line there's a reas…”

“One thing I've certainly observed is if you try to professionalize management at the top level, everyone below you will try to do the same thing. And that's how you end up with nine layers, you know, or nine is nice, like, 20 layers. So if you tell, if you as …”

“We've never had a CEO resign.”

“Generally, yes, because if you can raise a lot of money, it increases your odds of doing well dramatically and allows you to make some mistakes.”

“It depends, but, you know, roughly the team and CEO are probably going to get around 40, 45% of the company, and then we will have the rest because we came up with the idea, put in the money, did all the work, ah, and everyone gets paid from day one.”

“One of the most important lessons I learned, which every CEO should do is while you can be hands off the initial period of letting the leader transition and settle in, you have to be closely involved in all the big decisions. You have to be watchful of how the…”

“The moment The moment you will stop feeling difficult to fire people, you become like a monster. You will not be a good CEO.”

“And in, in my position, You know, you get to know all the shit that happens, most of the shit that happens in the company, and all the bad rumors, and all this guy did this, and this is not good for our culture, everything. It comes, and many times you don't e…”

“Ultimately CEO is ultimately responsible for everything. There's no excuses. So you can't ever abdicate. There's no such thing as like, I let this person do X, but I'm not responsible for the results when you're CEO.”

“You know when you're editing or when you're actually writing, and you want to be editing people's work as the CEO. You don't want to be writing, and if you feel like you're using a lot of red lines consistently in the same area of a company, that's a really ba…”

“And I think if the CEO doesn't have first rate marketing instincts, you kind of never get there.”

“And strategy, to make it really concrete for people, is you should be able to articulate your strategy in a two-page document, not six pages, not, you know, like, not, like, huge thing, but, like, A two-page concise document where one person holds the pen, and…”

“You have to see two to three years out and see where the wind is blowing, because most of the stuff that you can impact is going to create great outcomes two to three years, so not in the next six to 12 months.”

“I think there's a big difference between CEOs and politicians. It's okay for us to, you know, when we make a decision, if some people are not happy, it's okay for us to make that decision, because hopefully time will prove that that was a good decision, or tim…”

“Overall, I would say, 80% of the time, the CEO is better than the CTO, especially at the seed or early seed stage”

“I don't think that if you can't raise, you're not a good CEO. I think there are, depending on the business, again, there are businesses where, you know, the primary day-to-day job is not raising money. The primary day-to-day job is building a product and closi…”

“I think founders become, like, apologetic in the way they went around the company, because the company starts scaling, right? You have something that's working, and then the business starts growing, and then you have, like, all these people from the outside th…”

“So I try to get this out of them, and the way I get that usually is by saying, talk, talk me through what really frustrates you about where you are, and then you kind of get into, why does that really frustrate you, and then it'll always come down to the same …”

“CEO's, CRO's got a decision. You either stand up for it right there, or you accept the fact you're getting fired in nine months. Because you know you're not hitting that number, and I promise you they're gonna blame you, and this happens a lot.”

“I wouldn't put too much stock into these overconfident predictions from CEOs.”

“So I think truly great leadership, you know, the greatest CEOs are the ones that. Are they're always available, killing, you know, pushing the company forward, but are building organizations that if they step away, can run without them.”

“Really depends on the founder but probably very, very late. I wouldn't do it too soon. I think that the best CEOs are very product minded and should stay involved in product for as long as possible.”

“They should be almost kind of gods, but theos are just like the same people, and they can't be so perfect as people think they should be. You should just understand your Weaknesses, your strengths. You should understand why you're useful, and you should just m…”

“It's such just kind of, maybe the single common trait between successful and between all successful CEOs I may found is decisiveness. You should make decisions. And because when you make decisions, you move forward. Even if decisions, when decisions are stupid…”

“In the long term, like, when you look at the CEOs that are, like, truly the best, like, 50 year public, I don't know, maybe not 50 year, no one's in C for quite that long, but, like, you know, 10, 20 year public CEOs are the best resource allocators.”

“I think that having him ask me, hey, AJ, here are the three problems that we're dealing with as a company right now. Can you produce something and present to me and my leadership team on how you're going to solve it? It has two benefits. Even if I don't turn o…”

“I think that the founders need to be very involved, and the CEO needs to be very involved in that, that zero to ten million On, on kind of like how you're getting those initial customers to product market fit”

“The board is for governance. They're to make sure that there's no fraud, and like, it's a real company, and primarily to hire and fire the CEO.”

“So layoff is an important tool for CEOs to be able to use, to be able to prepare for a company for the future. And nobody wants to hit the button. Nobody wants to take the action. No employee wants to hear the words. It sends chills down everybody's spine, inc…”

“I think more than anything Like you really should work for a CEO who's like, whose ambition and expectations make you deeply, deeply uncomfortable. Like that, that is, I think if you think about like, you know, some huge, like, you know, sports nerd, and it's …”

“I don't. I think that being the PM, you need to be obsessed with every aspect of the experience, and I think that you need to really intimately understand the system. And what I mean by that is that any good experience has so many inputs and so many outputs, A…”

“There's 99% of CEOs come on the show, and they either shut up, or they say they vote for Kamala, and then it ends, and they're like, by the way, I'm so Trump, I am so Trump”

“Don't hire a leader yet. Hire individual contributor. At first just hire SDRs and you be the rep so that you get, I think for an early stage company, the CEO really has to develop the plays, figure out the message, at least that initial message.”

“If a company is looking for a new CEO that means that there's a problem or a set of problems that need to be solved. Do whatever diligence you need to do to gain a high conviction that you understand what those problems are, and then Honestly, map your abiliti…”

“I think for an early stage company, the CEO really has to develop the plays, figure out the message, at least that initial message.”

“Always no, but in the early stages, yes. So, you know, there are certain scales of companies where that, you know, maybe doesn't make sense anymore. But in the early days, yeah, I do think they should. I think outsourcing your, if you think that the most impor…”

“And if some CEO is telling you that they're seeing no value from AI, I'd be like, I'm not sure you know a whole lot.”

“I think a lot of CEOs are not right. If you look at the agenda, They are constantly meeting people, going to have a coffee with someone, and, or going to events, and I think the company needs them more than the external people.”

“I do agree that the best CEOs are exceptionally good capital allocators, but I don't think it's the most important part of a CEO's job. I think it is an important job, but by far not the most important. I think more important is to drive the culture. You drive…”

“If you go and talk to a CIO or a CTO of a large enterprise today, they're furiously seeking out ways to apply AI to their business. And the reason for that is because their CEO and their board told them, you're going to get fired because the entire fate of our…”

“The only advice I gave to this particular CEO is immediate, like he was hybrid. So I said to force a hundred percent of people returned to office in 30 days and let everyone go, except your S tier engineers, letting them all go. Because you don't need them.”

“I don't like the everyday of the job of a CEO and I like I able to control the destiny of the company, and I ultimately answer to the outcome of the event, like the outcome of the company, the outcome of the customer the outcome of the employee, right? I wante…”

“We making those entrepreneurs that are in there or these CEOs or these families, we make them Owners again, right? Because many of them weren't originally the founders of these companies.”

“And then the life lesson for founders, it's tough is look, Scott's gone now. Right. It's always a weird thing when you do M&A and it's not with the CEO because there's a good chance you outlast them.”

“Breakups are one of those few things in economic history that almost always work for almost everybody. The only person that loses is the CEO who wants to sit on the iron throne of all seven realms, not just Westeros.”

“It just creates sort of a risk averse behavior in the CEO. Like it's basically cash comp goes up and down a little bit, let's say, but an ISO you're swinging for the fences. Like you've got a strong incentive to swing. And so it's really had a dampening effect…”

“The only thing that matters with a CPO is whether they have the trust of the CEO.”

“I think it's DC condescending to tell the CEO how they're gonna work it out. It is beyond condescending. The great CEOs will figure it out.”

“Some CEOs are... I wouldn't say ignoring the problem, but don't understand the magnitude of what needs to change. And I think some are more kind of advanced in how they think about it and understand the magnitude of what needs to be changed.”

“And whatever, if any VPs get this far on the pod, whatever you do, do not reach out to your VCs to say there's problems with their CEO. You will, you're losing your job. And not only are you losing your job, it doesn't matter if you're right. You're your, at s…”

“On the thing where you're unique and different, you know, where you're changing the world, do it as different as you like, but all the boring stuff, just give the market what it wants.”

“Cause I think most CEOs I work with are not up for it is the truth. Cause most pre AI CEOs are not, they're not up. You guys know this too, from your portfolio, not all, but most are not actually up for the massive amount of, what's more than nine, nine, six, …”

“Also, I think the, I mean, there's a million things, like the CEO should be doing it, not like five founders speaking over each other.”

“I mean, I think the thing that you cannot have is them being like union representatives of your employees. They're not. They're there to represent the company, and therefore the CEO, and so if there's, if you don't have that as a CEO, like a trusted HR Leader …”

“When wealthy folks, especially VCs want to be a CEO, but they're not working at The insane rate of a traditional founder CEO. I just find those run out of energy.”

“Founders are lonely. I, you know, I could tell you as a former CEO, it's a lonely, punishing job.”

“The CEO being a good salesperson and being a real entrepreneur is actually more important because the CTO role can be fungible depending on how complicated it is.”