The Wisdom Wall

“Yes. Get rid of them. Build a, build a professional service organization. Hire more SEs who can do it. Customer success. Look, people think that's blasphemy. I get it. I don't believe in it. I inherited our customer success when Frank came in and he gave it to me. I got rid of it. It was an expense that I didn't see…”

“There is this idea, somehow, the desire to, and the ability to dominate, is linked with intelligence. A statement that a lot of people are making, including Jeff Hinton recently, That somehow, as soon as a machine becomes intelligent, it becomes uncontrollable because it's being smarter than us. It can influence us in…”

“You can have dispossessed urban poor forever, and nothing happens, but if you piss off the twenty-something-year-old middle class, the overeducated elites, they tend to cause trouble.”

“If you have a gun pointed to your head today, would you have done more? If the answer is yes, that means you're not doing a good job.”

“If you haven't gotten a boost this year from AI, fire half your team right before the holidays, give them a turkey and three months of severance, but they failed. You have a, your team is not good enough. They had 18 months to ship a product that mattered in this world.”

“You're close to, you know, eight hundred billion of market cap needed to return a Forex net for those multi-stage funds. Now, for reference, twenty-twenty-one, the best exit year of all time, there was 850 billion-ish of market cap exit value from that year. Ok, you need an entire year of IPOs in M&A just for this, you…”

“The only advice I gave to this particular CEO is, um, 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 think there is a Correlation between how aggressively people predict AGI is coming and how much capital they need to raise. So you've got Emodi from Anthropic, you've got Altman, OpenAI, Musk, XAI, all of these guys are saying that it's just around the corner and this industry is moving incredibly quickly. Then in…”

“I think you can learn more by studying World of Warcraft raiding guilds than you can learn from studying companies about coordination and, and, um, And, and, and what great looks like.”

“I said, I would take everything in your portfolio that received a valuation over the last two years, over five hundred million dollars, and I'd mark it down by 50%. What do you mean? And I said, well, if I look at the average gross stock in the NASDAQ, it's down 50%.”

“And so the one thing we absolutely have to do is research sunlight reflection. And so we have no way out of this without reflecting sunlight back into the solar system to buy us some time.”

“venture capital is a business about outliers, and when somebody succeeds, their opinion, and I think their decision-making gets over-indexed on their successes, which often, as you know, are outliers, and it's hard to generalize from a single outlier, and my belief is the most successful people in venture capital…”

“But what we don't want, which I think is not commonly supported by other early stage startups is what we don't really want at this stage is diversity of thoughts, and I know that doesn't make sense. It's, it's a little counterintuitive, but the reason why we don't is the way I view it is we're playing a football game,…”

“90% of the value added of a venture capitalist is finding and choosing the right investments.”

“Nine billion doesn't clear the bar for seed investing in 2026.”

“If no, if you're not into your 20, 27 roadmap deep into it by August of 20, 26 in the agentic world, your team is not good enough to survive today.”

“my philosophy is that the Ecom playbook Is the right playbook for SAS? Because if you look at e-comm, you have every single cent needs to equal a purchase or an ad to cart. You have hundreds of UGC creators, variety of creative, and you also have a ton of channels that you're essentially balancing to showcase the…”

“my hot take was probably fire most of your marketing team that is not a systems thinker. Like, stop brute forcing people in. Hire the right people into the roles because the role has changed.”

“That doesn't mean that they're not distilling. They may still be using distillation as a sub-step in their training procedure, But it does mean that distillation is only part of the story and that there's something that those labs are doing above and beyond distillation that's bringing the performance up above what the…”

“The reality is when you're getting open weights, you're not getting, it's not the same thing because all you get is the fixed weights that allow you to run the model. What you don't know is the black box inside those weights and how they work.”

“you have to be in the big outliers to drive great returns, and you're better off being in them at a very small percent than owning a large percent of a company that exits for three to 500. Those just aren't going to move the needle.”

“so many breakthroughs rely on a little bit of pushing the boundaries. I mean, Uber did with taxi regulation. Airbnb did with regulation. You're right. Polymarket did in terms of how they're regulated. So I'm actually going to get off my high horse and say you actually won that round. Is that, I mean, the interesting…”

“if you were trying to do the same amount of work and you believe you can do it with fewer people and therefore you shrink, um, your competition can also do the same, but they chose actually not to do the same amount of work. They chose to actually, you know, elevate and build a 10 X better product or build 10 times…”

“I asked him, what are a couple of the biggest lessons? And one of them was, never pass on price. So Fred says, never pass on price.”

“If the agent can run 24 seven autonomously, take all your data and build all the analytics, build all the dashboards, run autonomously out of it, um, then your data can flow between apps and you won't even care where it lives and all the fears about headless become true because Claude is your head and you don't need,…”

“It's a moat destroyer when LLMs will lift you from one vendor to the other, and, um, I, you know, I don't even, like, I literally was doing a pitch this week, and the founder was going on and on about their moats, and I, I immediately didn't want to invest. Like, I just, enough, I don't, you don't, your moat can be LLM…”

“the idea that work from home is going to benefit highly paid employees is sort of a total fantasy. Like, work from home done correctly, you should be hiring the world's greatest geniuses. There should be a labor arbitrage here, where you're finding really, really smart people who make a lot less money because of the,…”

“There's a very common Silicon Valley fallacy, which is there's like research is like the pinnacle. And then there's engineers who implement the research, you know, they're not quite there, but you know, they're still great. And then there's sales and marketing and all that dirty stuff. Oh, if only we could build a…”

“especially there's some high schools that, like, really focus on, like, you must do the math olympic, like, you must do this, the Amy, to then go to the IMO, and, like, this is the path to success, where actually that's kind of anti-signal, because there it's, like, you're not owning your fate or choosing your agency,…”

“If we need FDEs to make the product work, we have a shit product. Like, the point of FDEs should be accelerate and get them consuming faster. If you're putting in FDEs, because that's the only way you'll get a deal done, I'm sorry, my friend, you have a shit product.”

“And if you want to win, then actually it's something that I think attracts the right type of person and absolutely repels the wrong type of person.”

“So naturally there, there's, there's roles, I think that, that creep in, you know, you get the, like a lawyer and accountant are not going to work in the same way that, um, you know, a software engineer might. Um, and that's just a fact of life. So, okay. So if they don't want to work quite as hard, then you just need…”

“And I just think this going back to seed is for suckers. Like you want to invest the hour it blows up. The minute it blows up, you want to get the DM and just wire the money in AI. That's the play.”

“every, every healthy sales organization should be attrating the bottom 10% every year. You should be getting rid of 10% of your sales force every year.”

“There's like the kingmaker firms that you should accept at any price. Um, one example would be Founders Fund or Sequoia, uh, or people like that. Um, and so if you get an offer from them at X and the offer from, um, someone else is at two X, you should take their offer because even if you're maximizing, um, amount…”

“the companies that you can build on top of just the consumer and healthcare, Oftentimes there's the kind of companies that, that paint themselves into a corner that can never be trustworthy enough to go enterprise. They're the kind of companies where the business models would require you to take multiple showers every…”

“So I'll have to see, but we won't do, we'll never do, uh, Unless I'm forced to, I mean, if, you know, I do it for Sam Altman, but otherwise I'm not gonna do, there's, the firesides are dead and speakers are dead. There's just no point when podcasts are better.”

“Yeah, and every time you cut a corner, every time you invest in a founder that's really nice and really hardworking and really good guy, you never make any, any real money.”

“any Harvard MBA can cut costs. If you're smart, you could do it. It takes a genius to grow revenue.”

“Like you should be the strongest individual contributor in your team if you're leading that team. If you need a people manager, we'll give you a people manager to manage the communication. But I want you mainly hands on keyboard coding, designing, talking to users.”

“A CMO today should be able to run their own campaigns, and this is why. I'm not saying you have to spin up, uh, Marketo or HubSpot. I'm saying you should be able to tell your agent, and our agent, our AIVP marketing started running its own campaigns the last two weeks, and it's better, and so, You don't even need to…”

“It replaces merit of organization, um, with pull of individuals. Who is attracted to these places? The people who want to do something that, uh, for which you have to use, um, You know, pull. And, um, um, you know, the, the smoothest talkers, the people who, it's not the builders who are doing it, um, they go and like…”

“And like, obviously I bias towards having college athletes because they've, they've learned how to work hard. All you gotta do is teach them how to work smart. If you teach them how to work smart, it's really tough to teach someone how to work hard.”

“outbound will never be dead. You can't reach every single company and every single buyer with whatever marketing you're doing.”

“Anybody that's like, oh, well, you know, we're just going to cut our SDR team in half, I'm like, hmm, okay. That's an interesting move, right? That's a, that's a scared play that you're making because you're saying I can get the same productivity for half versus saying I can get this productivity and now I'm going to…”

“And the reason I did that then is a belief that if the role was going to get automated, Or that AI was not being adopted fast enough in those departments. It's time to let those people go and rebuild the organization as if we were building it knowing what technologies were available to us today.”

“The only way to fix a culture like that is to go and fire 99% of people and just rebuild it from the ground up.”

“The other thing I found is when we go out and we drink and we start shooting the shit, really good ideas can come of that too. It's not that we're going out and with a bunch of coworkers and talking about baseball. We're going out with a bunch of coworkers and getting drunk together and talking about work…”

“the second you care about that KPI and you chase it, you're selling from your own core business to go diversify. You're not focused on your day job.”

“They don't need to learn how to code. They need to learn how to create. They need to learn how to build.”

“If he can't get Box to 20 to 30% growth I'm, I'm giving up on, on the rest of the world.”

“AI alignment, don't get me wrong, is hard, but not the hardest problem. Human alignment is really the problem right now.”

“In the world where, like, Snowflake grew up, um, like, that made sense. In the world we are in today with AI, that doesn't make any sense. Because fundamentally, like, anyone can spin up a competitor of your product in the next two days. Anyone.”

“And I think that's right because realistically, in the journey of what's going on, the only significant things we've done, I've said this before in the podcast, we put in the money and we put in more money when they need it. We decide to hire or not hire and fire the CEO. We agree the broad strategic direction, and…”

“don't ever do diamonds in the rough, only do diamonds.”

“and so I say no, you don't, because I think, like, if, if you're trying to fulfill your personal emotional needs at work, like, I think that's a very fundamental problem, and you shouldn't try to do that.”

“we always say, do not bring your whole self to work. Like, whatever you do, do not bring your whole self to work.”

“We need to be selfish, and we need to be greedy. Those are good trades for an early stage investor.”

“the venture business as a whole doesn't, doesn't work. It doesn't work. It shouldn't work. Uh, and, and returns, uh, distribution, uh, are not divided equally between players.”

“If you work in defense, and if you start a defense company, your moral compass tends to be pretty clear on this question, which is, we have a democratically elected set of governments that represent the US, the Alliance, NATO, all of the countries participating. They set the rules, uh, and we abide by those rules.”

“If you find your logic being reduced to, I've got to get rid of this much money this month, and this entrepreneur is amazing, so I'm not sure about the opportunity, and I don't like the price, but have a goal. If that's your logic, let me give you some advice. Have your fun size.”

“For any founder in the first year, investing in paid as the means of growth is a death trap.”

“Unless you've been in the business for five years plus, You do not know your LTV. Period.”

“paid marketing to me is, uh, Is a cheap way out, and it's not competitively defensible. I should say cheap. It's actually the most expensive way out, and it's not competitively defensible at all, and it's not sustainable.”

“I think if you're not putting yourself out there in losing, sometimes you're not chasing competitive enough things.”

“Like every agent will leak data if it's allowed to, like every single agent will. That's how goal seeking works.”

“I'd actually don't think any of the agent vendors are safe from disruption because we will, even us, like everyone's promiscuous with agents. We will switch it. Like, this is so much better than what we had two weeks ago. We'll switch to the next one.”

“if I meet investors today that haven't actually downloaded and tried to build something themselves, I think they don't have the skill set to make an evaluation of the company they're looking at.”

“and, uh, the single most common feature is a broken relationship with their father.”

“I just think we have to give up on TAM. We just have to let the revenue show us the path to TAM.”

“I think there are only two types of companies for private companies. They're growing at insane rates or they're unfundable.”

“By the way, from the LP perspective, diversification at the level of the GP makes no sense, because they have multiple GPs, so, so the, the, the, the, the diversification gives nothing to LPs.”

“however, if you, uh, if you are a fund that is more middle of the road and you're not sure how Is it gonna be a raise or not? You're gonna find any excuse to keep the prices up, right? To look good on paper.”

“You know, if, if, if, if the typical, if a partner in a, in a, uh, in a partnership, especially large partnership with some, with politics and all that, uh, they're much more interested in their investments succeeding than anything else because that's their career.”

“Your competitors likely have a bunch of C players, so you want to go hire C players simply because they know the space? Ok, that's a short-term solve. Basically what you're solving for is you want to reduce ramp time, you want them to be able to get enabled faster because they know the domain. Fine, problem is nine…”

“Inside sales is, your sales leader is in the office five days a week, and the inside sales reps have to be sitting there. Have to be. So inside sales is an in-office deal. And, and there could be no exceptions in my opinion.”

“You should be shooting the bottom 10% of your sales organization every year.”

“You can identify a point, a top, oh, .1% founder Without talking to them. I don't think you can do it without any interactions, but without talk, I do, I a hundred percent believe it's possible.”

“Reskill is a delusion. Reskill is something we say to, to make everybody feel better. Reskilling is like when you get, when you, they do layoffs and they bring you in the room and they give you a packet of jobs potentially. It's just to make people feel better. No one's ever reskilled anyone ever, and it's harder in…”

“you can have low cost energy, you can have, uh, more energy, and you can have lower carbon energy at the same time.”

“I actually think there are not enough ambitious founders out there, because ultimately the, the, the throughput of the company, like how many parallel work streams you can take at a given time is dictated by number of great leaders you have in the company.”

“Yeah, I'd say, like, as I said before, like, this is, This is very hard, like, this only way to do it, like, we're going against, you know, big, big, big energy companies with, like, huge balance sheets. You know, billions in revenue. The only way to win is, you know, with much more balance sheets, much less cash, much…”

“I also think marketing is not that complicated. I mean, it's not like engineering where, you know, our VP of engineering, he has so much deep, deep, deep knowledge in the domain. I just don't believe it's that way for marketing. I think people overly complex it, but at the end of the day, it's an intuitive thing.”

“this is why I tell founders to take their exits and then say no, because they can go bigger, but, but by default, take it.”

“why would I care, as an example, about somebody's win-loss reports when your sales force sucks? I'm trying to change your sales force. Why would I look at the win-loss reports when people really don't know why they won and certainly don't know why they lost?”

“I fully believe if they're like, hey, Sequoia led our seed, and I'm like, hey, are they doing your A, and they're like, Well, they're doing their pro rata. I'm like, this is not a good company. Like, objectively is not a good company.”

“I feel like because of PR goals, AGI has been hyped up as a finish line, but I don't think it's a finish line. It's just, we'll have continually improving capabilities for, you know, decades to come.”

“The companies with something to lose whose statements over time have become more moderated. So, you know, I, I find that as your established company, you just say more sensible things, but there are some companies that I think are at greater existential risk. Um, and I find those companies, some of those companies that…”

“And ultimately I believe hybrid is the worst. The worst thing is the thing where like you have half of the team in person. They have an enormous information advantage. They figure out their own rituals and ways of communicating and collaborating. The other half of the team sits somewhere else. You try to come together…”

“The most folks from the last decade or 15 years are not the right people for the next decade.”

“When you have demand like this, like you have for, um, uh, the initial GC, like the initial hyperscaler clouds. Um, and I think we're seeing an even greater cohorted demand curve for, for AI inference. Sometimes you just got to shut your mind up and, and invest with the momentum.”

“I, I definitely disagree with that. I think the moat is still fundamentally in technology, not in, in distribution.”

“To me, sometimes it just feels like a little bit of like, uh, it just feels like a different job than like the craft of venture capital where you're almost playing the lottery where you're like, okay, I have these 30 names that I own. I'm gonna try to do two of them, and then if one of them hits and is a huge success,…”

“We bring in a CRO pre-product. You need a salesperson to create the sales playbook.”

“If you're going to be in my interview process, you are either uniquely qualified to qualify, or you are uniquely qualified to sell. If you are not one of those two things, you are not getting into the interview process.”

“I don't believe in King making and that's maybe a controversial thing to say. I think one of the lessons, you know, you'd think like, oh, Sequoia should be able to King make companies and like, that's so great. And that would be, by the way, if that was true, it'd be really economically valuable for our LPs if that was…”

“No, I think pro rata should be earned.”

“Uh, but in his mind, in his mind, most chief marketing officers are not good. The truth is I actually agree with him. And for a while I was looking for a CMO with this experience, that experience, that experience, and what I've realized is, like, the best CMOs I've encountered over the last few years are the ones that…”

“I think if you're going to own double digits, my view ethically is you got to be there till the end. Otherwise, you're dead weight on the cap table.”

“I probably would not hire that Silicon Valley. Why? I think what you need to bring to the table is hunger, is lots of dignity, lots of dedication, lots of experimental mindset, and you cannot get there when you basically worked for, like, best-in-class companies, seeing how growth runs there, And you come into a small…”

“Hold is your best time to trade on, to legally trade on inside information, though. If you're on the board or close to it, it's your best time to trade on that illegal by not trading. Yeah, you can hold legally with inside information. It's a privileged position. You can sit on that board and know what's coming next…”

“Oh, we're going to make your human beings 10% more efficient because of the AI co-pilot. When reality is they're gonna want a product that is like, no, no, no, I don't need 75% of these people anymore. Give me that product.”

“They're a reflection of how much the model had been trained on those benchmarks.”

“No, no, that's not a matter of time. That's, that's fundamentally the, the way that sequence models work. Like we are training statistical models of text.”

“I see PM as, think of it as like a hire of last resort. And so I don't think a company should be allergic to hiring them, but it shouldn't be the default.”

“I honestly think you don't need a CPO until maybe like as a founder, you're starting to think about transitioning into the chairman role.”

“I think it's incredible marketing. It's a way of differentiating against sort of the market. Everybody's going to be intense, but we're super intense. And so like, we're going to be like Olympians and, you know, in terms of work ethic, it's like a coded way of saying, Hey, we're self-selecting to like 20 to 26 year…”

“the only thing that matters for culture is growth, like, business growth, because for a business that's growing at, like, an amazing clip, it's always gonna have Cultural sort of issues that, you know, make it kind of suck to like work there, but everybody's okay with that and leaned in because they see a path for…”

“You don't need half your company, and Palantir and Shopify are proving it. You don't need half your company. You literally don't need half the people working at your company. You don't need them today.”

“If you look at, uh, the most incredible companies in the past, you know, you look at Revolut, you look at Deliveroo, all of these companies, the amount of work that these founders and these early teams put in was, was tremendous. I mean, it was seven days a week, you know, it was nights and weekends. I mean, that's…”

“Ironically, as a brand person, I would say products more important than brand right now. Products all that matters actually brand secondary.”

“my mental model on the dinner is the bankers have just screwed you over for a buck a share, and in return, they buy you a very expensive dinner, and they liquor you up so you forget.”

“I work with many, and when they actively manage, they do not get the right decisions. They push managers to do things they shouldn't do. They push them to go enterprise before they should, push them to do more products, push them to scale faster, take more cash on because they want markups. I think you want passive.”

“Some people are simply two to three times better, like two to three times faster than anybody else, right? They just code faster. There are some people who simply have two to three times more better ideas. There are people who simply work two to three times as hard. There are people who have two to three times fewer…”

“nobody gives a shit about on chain issuance. Like the only place where people are even thinking about on chain issuance is like in your head. What people want is capital as a service.”

“My rule is if you haven't grown because of AI, you've failed.”

“Cause I'm realistic enough to say that even if I, you know, if you have a venture board member who is an amazing board member, but can no longer speak to the money. Because there's no longer at the vent, at that venture firm, then to a rounding error, they're useless.”

“specs, like, you know, companies write product specs that like go from someone's idea that turns into a product spec, and then that goes into design, that goes into engineering. This process is like dead. Like, why would you write specs if you can go from your idea To an exact prototype. So this whole middle assembly…”

“In 90 plus cases of modern professions, you can study on your own, and you can do it in a fraction of the time.”

“I call it the AI slow roll, and I think it's the number one thing killing B to B companies is the AI slow roll.”

“the greatest founders that I know are motivated by the internal fire and being in London. I push myself every day to be better. Yeah, everyone around me is relatively mediocre in terms of London, generally speaking, generally group population wise. I didn't need them to feel for failure. I will push myself and the best…”

“I recommend founders take, um, enough secondary so that they can, they can live an account for life, right? They don't need to worry about how do they feed the family? How do they support the kids? How do they, you know, buy a house? You know, I think they should, you know, like I would say, uh, in Melbourne, I don't,…”

“if a young founder, European founder came to me, it's like, Hey, I have this brilliant idea of how to use AI or like a new model or something like that. What should I do? Uh, it's like a hundred percent. Go to Silicon Valley. A hundred percent. Uh, you, you absolutely maximize your chances.”

“smaller companies shouldn't have PMs because the founder is playing that role.”

“All the non-technical CEOs that I've seen, especially take over my investments as outside CEOs, they never understand the product.”

“I think the, the, the mistake is to not raise enough money. Like every now and then someone gets like a, you know, like a million dollar valuation, they raised like fifty million. I think that's a mistake. Like you want to raise enough money at that high valuation. And then number two, don't spend the money.”

“A lot of people say it's harder than you think, where I think it's actually easier than you think. Because I said it's hard, yes, but it's easier than in Europe. People buy faster.”

“If you have a hot hand in venture and you're not running the place, I would leave the next day.”

“The other wonderful thing about starting a new firm right now that no one will ever say, not only do you ditch your colleagues track record, you also ditch your own, right? You literally go there and go, I was at mega firm from 2016 to 2024. I did some deals. Some are great. Some are shit. It's not obvious yet, but…”

“If you have access to capital that's large and forgiving, which is what these mega funds have, then you should play the big balls game. Cause you're exactly right. You don't do it. You have to do less work. If it works great, you make out the same as Jason who did the seed for suckers and Rory who did the A. And if it…”

“But the reality is, like, if you write a small check, and, like, you're one of many, then, like, you don't make any difference. It doesn't matter how smart you are.”

“And my fiduciary duty comes in at the moment where I write the check. It's like, I'm underwriting that person. It's like, hey, do I think this guy will be a good CEO? And once you're there, it's like, I'm just, I'm here to enable this guy. And like, even when I disagree with him, I'm just gonna, like, help him do what…”

“find the customers who are really good at what they do, and then, you know, chase them, even over a fit to them, um, as long as you have conviction that, you know, everyone else will follow.”

“the causality is that if we put capital in place here, great companies will rise to the occasion and, and, and supply of companies will come.”

“I don't buy into that. I think price it as high as you can price it.”

“If the customer is not separating with some sort of cash, there's just not enough skin in the game for them to put in the time to work with you for a few weeks, for a few months, for a few quarters to build a product. So I'm very anti unpaid design partners because the cost for them to just say yes is a lot lower than…”

“increasingly if you are absolutely, if you are a 10 to twenty billion company, don't go to the U.S. because you'll get lost.”

“And there have been places where over-regulating these things has actually produced perverse outcomes, where investors are incentivized to invest in big extractive industries, for example, rather than medium-sized, scaling, green economy companies, because one can produce the data and the other can't.”

“And you realize if the company calls you back, the company sucks.”

“Uh, I believe, uh, I believe that, like, DPI is the most important thing, and marks are completely for suckers.”

“GPUs are, you know, are a good trick for AI, but they're not built for AI.”

“it was very risky, because it took time to monetize and get to something that I could sell and everything, but now that I am looking back, it's probably what Medo do today. It's because I thought about the big picture, everything's smooth together, and it's not a patch of different software.”

“There is no way you can Make a team of developers become a better developer if you are not the best developer of the team yourself.”

“If you give budget to people, they will just spend the budget. They, they won't have any responsibility or whatever. If you don't give them budget, they will have to spend responsibly.”

“One thing I noticed is that, um, we also do an IQ test, and it's the second best predictive KPI, uh, on the performance of the person.”

“if you want to commoditize the market and have every company own your software, you have to have a very small price.”

“A principal is not actually waiting for an exit. They just want a promotion, man.”

“I don't think you should evaluate any company by the models that are underneath it. Even model companies.”

“Open always wins. Always.”

“when I see companies sometimes unwilling to raise a round because it's going to be lower than this, like, fictitious number they have in their own head. I see this with, like, IPOs now, where, like, companies are like, oh, well, I can't go public unless I hit the valuation I had in 2020, and that valuation is fake. And…”

“You can bucket great founders into three backgrounds. The most common is that you have kind of a messed up childhood. The second most common would be, ah, you're gay, and the third most common would be you were adopted. Look at like a list of, of, of all-time greats. Elon Musk kind of messed up childhood, Jeff Bezos,…”

“We as a venture industry have to think about how to create monopolies. Like, the regulator doesn't want monopolies, but we want monopolies. We want companies with increasing returns to scale, with deep defensible moats. You build this thing, it has this huge moat, and every extra revenue, customer, whatever it gets,…”

“They did every AI company a huge disservice because everybody thinks that just like empty text box is now the right interface, and it is for ChatGPT, and it is incorrect for basically everything else.”

“For music, It's very different from text, and I think people will very sloppily look at the world of OpenAI and Anthropic and the hyperscalers and say, um, audio is just a couple years behind, which it is, but that scale is gonna solve all these things. But unlike those domains where you're trying to just get more and…”

“If, if the LPs knew, like if they, if they tracked, what's the return on follow-on checks versus first checks, there'd be pitchforks and like, Revolts in the street. It's so bad.”

“The importance of freedom of speech, there's a, there's a really interesting distinction between freedom of speech and freedom of reach, right? So, if you're standing at the local corner, and standing on a soapbox, and saying, the moon is made out of blue cheese, and the earth is flat, and so forth, it's fine, go…”

“Look, if I could, through a democratic process, because I believe in democracies, I believe in collective governance, get, um, our society to agree to say, hey, what we should do is identify some topics that panels of experts can, can yield To a truth determination on. I would prefer we do with all media, and by the…”

“if you want competition with those large companies from startups, Investors, say for example, I'm an investor who's gonna put a billion dollars into a company that might compete with one of the large tech companies. I'm only gonna put the billion dollars in if I have a chance of an acquisition exit, because I'm gonna…”

“I actually think, um, none of this stuff really matters that much. I think what really matters is founder quality and founder ambition. So I think for a, for a country to be successful, they should attract the most aggressive founders. And, and everything else is a lot less important.”

“I used to think that, that you needed to make sure that there was always a degree of process, um, when teams work together on something and including something new. I have now learned that it's possible with exceptional people to let's, let's just let them get on with the job without any stand-ups, any predictions on…”

“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, including my own. But sometimes it's very important for us to…”

“I'm not less committed now. I'm honestly able to drop back and scan the field and throw passes in a way that I wasn't before. You, it's actually a decent way to encourage the entrepreneur to play small ball. For somebody who grew up without a lot, you know, mowing lawns, to go be able to make like X, Millions or tens…”

“And the reality is I was dead wrong. We're getting back into the office. The collaboration, the productivity, like, it's not even close, and it's very painful getting back into the office, and you know what is worse than that? It's not getting back in the office.”

“It's the disaffection. It's the, I don't want to be paternalistic, but my, my colleague, Tiago, who is our, our, uh, one of our key leaders here, he said, look, people think they're happier sitting at home, and they're not. And they end up quitting like a week later. They say, no, no, I love working from home. And then…”

“Well, I, I never believed it, but I was forced to believe that, you know, in order to scale the company to hire experienced professional managers, that's a dead end.”

“If you look at, uh, statistics, so 20 to 25 is actually quite negative. Like, too early is a negative, um, then, uh, 25 to 30 is, is okay. 30 to 35 is the best age. After 35, I mean, there is a clear negative, uh, correlation, uh, with the success. So sweet spot is 25 to 35 for founders.”

“Majority of people believe that our balanced life allows you to be happy and achieve your goals. I think in the reality, a disbalanced life allows you definitely to achieve your goals, so more kind of imbalanced you are, more focused on your goals, sacrificing everything else, more likely you will succeed these goals,…”

“I'm not so keen of building portfolios. If I find cool companies that make a difference, that is where the beef is. And if you have one or two of them, every portfolio looks great.”

“I now say alignment is a four letter word. Um, like I don't want alignment. I want, I want, I want highly opinionated people making decisions and then being accountable for them, right?”

“you have to be fairly settled in yourself to allow a child to have a better life than you had. I, I know the cliches that every parent wants that. No. I don't, I mean, I, experience does not bear that out.”

“Because if you really believe in a world in which everyone who gets to the top deserves to get to the top, you have to believe in a world in which those who get to the bottom deserve to be at the bottom.”

“I don't think you should bring your full self anywhere, because if we really think about what your full self is, it includes, you know, infantile bits of you, bits of you when you were two, bits of you that are full of rage, bits of you that are full of envy and bitterness and confusion and et cetera, and things that…”

“So my view is that it's the only thing that matters. And if you ask me what's our retention, what's our activation rate, what's our CAC, I couldn't tell you really any of those things because I don't think they're real, like they're completely irrelevant. So the only thing that at the end of the day matters is what's…”

“Now the real downside to me is that it's at one billion mark, because once we become unicorn and people think, oh, we've made it. Like, like we've done, we, we, we're great now. Kind of people get less hungry. And then you get applications of people who look for a safe space to work.”

“If you're a good product manager, you don't need an A-B test. You should be able to know what is the right product.”

“There's no CAC discussion. We only talk about ROI. Because if you talk about CAC, you'll always acquire the worst cohorts.”

“I think it's when you start, um, bringing a little bit of belief. I think the less you believe in, the Better it is, you know. I have no belief in anything, you know. I have no belief in anything. Like, it's, it's true, you know, because... Well, I don't necessarily believe more in brand than in, uh, influencers, than…”

“Investing in brand in the early days is the worst decision you can make.”

“I would say generally founders who've had enormous, enormous success and exits come to the next opportunity with some degree of hubris. I, I, I speak about this personally. I sold my first business And I thought I could conquer anything. And they look at any vertical, and they, you kind of go, I'm going to disrupt…”

“I believe sales experience is overrated. I think When you are a highly tenured rep, I think some people believe that. It should be weighted the most when hiring a sales rep. I don't think that is true. I think there are other characteristics that I would weigh over sales experience.”

“Even layoffs are simpler, because layoffs is like computation. Cut, and you're just in two or three weeks, and you continue your work. But fundraising, it's like, just like, it's each day you're getting no, no, no, no, no, no, no, no, and you're starting to lose, like, a belief in yourself”

“investors, they, especially in big funds, uh, you usually start your conversation not with, like, partners or mentioned partners, but with analysts or with principles. And, uh, this, uh, people usually have profile kind of, uh, Graduated in Harvard, MBA in Stanford, or graduated in Stanford, MBA in Harvard, and they…”

“Like, there's this canonical question, I think, in our industry. Is it the market or is it the team, right? And I think many great firms would argue that it's market. In my view, it's very clearly the team.”

“There's, there's so much long tail risk in a company that I feel like the exercise around pattern recognition, um, benchmarking, um, as, as just like two examples, risk mitigation as a third are exercises in psychological safety.”

“I think every product team should be probably between six to eight people. Most of those people should be engineers. If possible, one of those people should be a data scientist. One should be a designer. And then I think a PM is optional.”

“My terminology from experience is there are VCs that are seagulls, And here's my definition. They fly into a room, or fly into a meeting, fly into a location, they basically take a shit, and they fly away. They talk a lot, they give work to do for other people to do on the management team that distracts the management…”

“There's a few in every fund that really matter, at least matter from a financial performance perspective. And when they really matter, the common is, is exactly the same as the preferred, is exactly the same as the preferred two, the series A, they're all worth the same.”

“my experience over the last 10 years, there's the legal agreements don't matter. There are always ways for an investor to quote unquote screw over a founder or for a founder to screw over an investor. It goes both ways. And the legal, the illegal agreements do not matter.”

“VCs are obviously incentivized for founders to think that or to be scared of that. Some ways it's a threat and there's all sorts of weird incentives in the middle, right? It's, um, I'm raising my fund. I need to show some markups or I'm a, I'm a trying to get a promotion at a firm. I need my companies to raise money.”

“building a startup is, um, truly awful. It's like a truly, truly bad experience. Um, and it will ruin your life basically in various different ways. And by the way, that's if it goes well or if it doesn't go well.”

“I, for a lot of my career, was thinking that model architectures really mattered, and by having clever, complex architectures and sub-modules inside architectures, you would have, that was the route to sort of better AI systems. For the most part, I don't believe this as much anymore. I think basically models don't…”

“I don't want to say it's BS. I think it's backwards. You need a salesperson to create the sales playbook.”

“So you bring the engineer in, number one, it slows the process down, ok? Number two, there's risk. I don't know what this engineer is going to say to the sales guy. We're recruiting. He could say something about the product that he shouldn't say. It scares the shit out of the rep, okay? So there's risk there. Three,…”

“A reps at Oracle right now. He's selling software, right? He's selling software. That's what he's going to say, and I'm going to say, okay, are you doing pipeline generation? Yeah. I'm selling our new X product into all these Oracle accounts that have never brought X product. I'm, I'm hunting for new logos. No, you're…”

“Any inside salesperson should recognize that by being in the office, they are going to get better faster. They're going to develop faster. They're going to be better at what they are doing faster.”

“A lot of people think if I nail PLG, then I'll nail enterprise. You can nail PLG and enterprise. I just would argue that nailing one does not necessarily make you more likely To nail the other. So if you can do both, do both, but You gotta, in my opinion, you gotta start with direct sales, and then let the product get…”

“If you're not able to actually transform the model to be better at the thing that you care about, if you're not the one building the model, if you're just a consumer of the model, um, you're structurally disadvantaged to build that product.”

“What most people end up doing Is doing this the wrong way, right? They go to SOC II saying, what can I build? And then they build the thing SOC II says you shall build. Which is why all enterprise software ends up being shit.”

“There is a definition of success in this business. You're either a slugger or you are not. If you are generating billion dollar gains, you are a slugger. Doug Leone is a slugger. Pat Grady is a slugger. And Jurita is a slugger, right? So you either are slugging or you're not. And I think one of the delusions of this…”

“I tell founders all the time, if you find someone who's going to transform your business, give them five percent of the company. Now I say that it's an extreme statement. Maybe it's four percent, maybe it's three percent. But I think we get very married to like, oh, an early engineer is worth 50 bips and a executive is…”

“I think the problems of, um, Uh, of the lean method are coming home to roost. What every VC wants to see is, you know, and especially in like app facing stuff is they want to see product market fit. There's a method we have, right? You come up with like a, you know, rough business model canvas, and then you go out and…”

“the American system, what it enables is both ends of the risk curve. We both have the downside sort of part of the risk curve where you have the homeless, the gun violence, et cetera, but we will also enable the opposite end of the risk curve, the Musks, the Vanderbilts, the Rockefellers, and in some ways you can't get…”

“people love software because, you know, sort of the marginal distribution costs are zero. Perhaps what people need to realize is also that the marginal returns are zero as well, because there is no moat, because two Stanford kids, especially with today's AI, can replicate your, you know, sort of SaaS for plumbers, you…”

“Since 2021. Every founder with a decent exit, I tell them to take it now. A hundred percent. I tell them to take it for this reason.”

“I don't like commission plan salespeople in the journey to product market fit. Like I just want pure equity people.”

“none of these people had to go out and find product market fit. They came into companies where there was already product market fit, and they just had to operate their little part of that company, or big part of that company, where they were kind of keeping its status quo.”

“You don't get enough advice, and then you start getting capital, and you have stakeholders, and you get too much advice, and the problem is a lot of this advice is either bad advice, 99% of the advice is bad advice, and then the rest of the advice is contradictory to each other.”

“even if you don't have product market fit, you can sell a business for four hundred million, you know, because if you're just good enough to generate constantly more traffic and it's cheaper to, to generate or buy traffic than the money you're making, the business is still growing.”

“If I'm in Europe and I'm starting a company, I would get out.”

“One of our tenants is definitely that market size TAM is noise.”

“I would argue we're in an era now where they, they shouldn't, um, and they should think about, uh, they should think about what is a, what is an interesting point of view they can have, and what are the, what is the most pure way to get that point of view across?”

“no, I do think you should take your LP's money less seriously than I do. I genuinely think it's a bad thing.”

“So I, I really believe very strongly that your first head of growth is your founder, and their first hires, I wouldn't start by hiring somebody senior.”

“If the churn is anything more than three or four percent a month, it's not even software anymore.”

“my advice to everyone out there that, like, emails me, hey, can I invest in Sastra Fund? Don't put money into any of them, is my advice to individuals. To individuals because I don't even think everyone's full of shit. I think even making three, if you do a seed X, a seed funding, you make three X net after 16 years as…”

“The one thing that really kills me is when I see a founder playing the victim here and say, well, my investors didn't help me enough. Like, That's not their job. Their job is to give you money and hopefully do no harm.”

“I think one of the frustrations with Gen AI, as the technology is commoditizing so quickly, is it's a sustaining innovation. It's actually going to get sprinkled across all businesses to lower costs in call centers or to improve the product in personalization. But it's actually not going to create the sort of, it's not…”

“If you are doing PLG and you're doing paid acquisition, sub a hundred million in revenue, I'm not sure you're really PLG.”

“I'm of two minds on this. I think a lot of AI value will accrue to existing large distribution players. AI is not, um, naturally disruptive in the way that the shift from on-prem to cloud was, right, which obviously I had a front row seat to.”

“this idea that higher Higher slow, fire fast. In a way it's, well, it's good, it reads good on paper, but it's not applicable in, in real life.”

“Yeah, part of me would say, don't fucking start a company, man. Get a nice job. And have fun. And, uh, because I don't believe in, uh, In work-life balance. And, uh, because in a way, building a company is gonna suck you into building the company. I don't think you can really put barriers.”

“I did not know. I still don't know how to build culture when nobody's coming into the office.”

“I don't think it matters if your product is better anymore. Boom. Whoa, hot take, Harry. Distribution trumps all.”

“I've seen the people who make the real amounts of money, the people who become the moguls, they have an incredibly strong sense of what they are owed by society and by the system or by other people that I don't have. And I think it's almost a brain defect. If you become a billionaire, you don't just become it randomly.…”

“The worst deals are the most competitive deals. They're the ones that are super consensus.”

“this is by the way, the biggest risk of taking seed money from an institutional fund is that like doing your prorata is super lazy, doing more than your prorata is actually a signal in If you're not going to have real signal, if you don't have high conviction, you probably shouldn't be doing anything at all because the…”

“Having like pushing your team to do things like deal memos, for example, forces them to like put down a number that they're later going to be judged by. So the investment team is going to go back and they're going to look at that investment memo and they're going to say, wow, you outperformed expectation on this deal.…”

“I think like the writing has been on the wall for a while that globalization didn't really work and that traditional strategic deterrence with nuclear weapons was not going to be the, the only thing that drove, uh, reduction in conflict globally.”

“There's a reason why I would never hire them or invest in them. Those guys are the ones that break the minute something breaks. They never ever have experienced being bullied, being the fat kid in the corner with no friends.”

“if death is not inevitable, Then you have to reconsider all of your existential scaffolding.”

“The meaning of life to me is, is like, is this, that when intelligence reaches a certain level of capability, which is right now, like after 4.5 billion years on this earth, In the past few years, we have reached a critical point after 4.5 billion years for the first time. Where intelligence can say the only thing…”

“hiring great people and get out of their way is like, is basically an, it is assuming that everyone is magically going to have the same understanding of the world, is magically going to have the same quality bar, is magically going to be aligned on how they do things, like is impossible to happen, right?”

“in the early days I was looking at markets and total addressable market time and technology and differentiators. And I, I, I simply realized that all of that is bullshit. You know, it's not important at all.”

“So I'm looking for the individual who, whose parents went through ugly divorces. I'm looking for the individual who lived in a closet for a while. I'm looking for the individual who was a socially isolated child. I'm looking for people who went through real difficulty in life and became successful.”

“Like you should, discovery is five minutes. That's what discovery should be. And if you need more than five minutes to do discovery, then you really, you're not putting the work in to understand who your customers are.”

“when somebody fails at something. You do not give them shits. It's more about how you learned anything. If they haven't learned anything, you can fire them. But if they learned something, that means that at least they can iterate.”

“On the people that report to me, I always try to get at least one person that I don't like, because if I don't like them, but they are smart and they can get shit done, I will hate everything they say, but I will put my thoughts into believing them, trying to think about them, trying to think why they're coming with…”

“So, but that then saying that that is a causal rule that drives to create big companies, that's absolute bullshit. Because I can have a company that is actually declining while I'm milking out a lot of cash and I will get to a rule of 40, but obviously that is not a good company.”

“If you fund a generational company and the outcome is insanely enormous, you should say yes to whatever that number is at the, at the seed stage.”

“on balance, I don't think reserves and follow ons, I think it actually hurts seed investing and it hurts seed investing in two ways. One is, um, it depresses DPI.”

“The company's either going to work or not work. And you are not the reason for either of those two things. If anything, you're the reason it's not going to work.”

“if you are a seller today and you engage a potential buyer and you're wasting your time asking about what fucking CRM that they use or where they're located or who they do business with or how they make money, you're fucked. You just, just don't even call.”

“Discovery as we know it is fucked, right? And what, when discovery, I took out the word discovery from the sales process and I inserted the word teaching. And words matter turns out. And what I would prefer my organization, what they do when they engage with a potential buyer is they teach them, teach them about their…”

“I would argue that that sheet music get created by a professional that has the pattern recognition that has seen it before. So I do not believe a founder should build that sheet music or playbook for how we're going to go to market.”

“I don't think that the way you build a big company or the way you get a big exit is by investing in the most ambitious companies, growing the fastest. Those are also the companies that crash into it.”

“I think if you're, from the get-go, if you're talking about creating a category, you're making a mistake. I think a lot of times when we talk about category creation, it's in retrospect that we see that a category was created. It wasn't started that way.”

“there's no question that, at the end of the day, you, most of your returns are gonna come from very few deals. It's not gonna be spread evenly. That's, that's a fact. The question is, can you recognize it early on, or can you recognize it really at any point? And I don't think you can. I think we delude ourselves into…”

“I'm going to get, I, I believe that most companies, you know, and I have a chapter in Eli Gill's high growth handbook on the topic in a, in a fairly lengthy core answer as well on, I believe most companies are better Off going public early period.”

“Like, I mean, I think it's definitely not a billion dollars. Like, I think it's, you have to be maybe worth ten billion. At least five.”

“yes, you can have balance and you can still build an extremely efficient and great business that's doing great work. You don't have to put in a 120 hours a week, a hundred hours a week and not have any balance. And torch, you know, family relationships and everything else just to, to go build a business.”

“The price at which you go public is completely irrelevant. Almost nobody sells at the price of the IPO. Everybody's locked up. And in the end, it just matters at the point sort of like when lockups are over, when somebody wants to sell, et cetera. So the price at which you go, at which you go public doesn't matter.…”

“Have you tried not sending a welcome email? Not sending, you know, the first three, four, five emails to get people to use the products. And of course they haven't. And I tell them, try it. Take 2030, whatever it takes to be statistically significant and don't send emails. And let's see what the true deviation and…”

“If you have a monopoly, for example, Google has this 20%, you know, side project bullshit where they used to. If you have a monopoly business with 99% gross margins or 90% margins, maybe letting your employees waste time once in a while maybe isn't catastrophic. Most of us do not run pure monopoly businesses with 90%…”

“If you're rocking it as a product manager, everybody thinks you suck. If sales loves you, engineering hates you. Because you're chasing deals and you're not thinking about the long-term future. If engineering loves you, sales hates you, because you're just doing long-term stuff, and you're never helping them close the…”

“I mean, as a venture, Uh, manager, you get paid, uh, two and 20, maybe more, maybe a little more, maybe a little less, but those are, um, meaningful fees. The reason that you get those fees is because, um, you can outperform, um, you know, an index and, um, you know, every private equity Firm, um, you know, uses a…”

“where it runs a risk is if you start, start to say, you know, we've got to do X. First of all, you'll attract people that think X is, even though you say the journey is much longer that they'll think that that's the, that's the end state. Um, and then secondly, it might be that you start to optimize for that end state…”

“The best actually strategically lent out of their best positions, and so I think we'll see a movement away from the momentum, portfolio management, liquidity management doesn't matter, to actually the best returning managers being incredibly disciplined around core tenants of portfolio management, especially liquidity…”

“So I, I think that they, I think that there's, unfortunately, there's a lot of founders who, after they leave their companies, um, end up either miserable or, or dead.”

“I think it's very rare to find someone who said, I started out just trying to build, you know, the, the platform for, you know, People to sell snowboards, and I, and, you know, and I ended up building, building Shopify, or I started out, you know, building that small thing. I think it's a, that's a very, very, very…”

“Harry, don't hire anybody from Google. Okay. Um, don't hire anybody that says on their LinkedIn, ex Google, ex Amazon, ex Facebook. Okay. When they put that on their LinkedIn, they're associating themselves with the success of the business. And it is almost impossible to tell what contributions they actually made to…”

“What you're looking for when hiring that sales executive is something very different. The first sales executive. And here's my point of view. You want to hire. An ex banker, an ex-consultant, an ex-lawyer. You don't even necessarily want to hire an ex-sales leader, right, or a sales leader. You want to hire someone…”

“Then the fee and carry model doesn't work because those services show up as a cost center on the statement, the cash flow statement of the VC firm itself.”

“And so when I hear people say that, I think you have a product problem. And if you can't convince a founder that partnering with you is what's best for their business in the face of your competition, You need to do something different.”

“Like, risk is just all the investors and, you know, especially when they want to, Extract a bit better terms or, you know, bully you in a down market or whatever, right? They will tell you, like, oh, we would lose you. We'd hate to see you lose everything, right? But the reality is, my everything is my mind, right?…”

“So I just think there's another problem outside of, it's a different form of risk, which is the likelihood of success, in my opinion, goes way down for those companies, which is super counterintuitive because you're like, well, but they have more money at a higher price. Doesn't that make them more, more likely to be…”

“I believe that the outliers usually start out at a low price, because they're outliers. Because they're non-consensus and right. People tend to believe that the world is divided between low price deals with low upside and high price deals with high upside. I don't agree with that, right? I disagree with that. And so I…”

“we do not focus on ownership. We actually think that's a very problematic mindset. There's a whole bunch of downstream issues, including, first of all, our missions about alignment with the founder, and the whole ownership mentality. You can twist yourself in pretzels trying to explain some notion of how that's aligned…”

“I think models are not a mode. Models eventually don't matter. What matters most is the people building those models. And how fast can you change and learn from those models?”

“And also is that everybody who gives advice is a successful person because, you know, you got to have a resume to make your advice weighted, so all the people who have the most, you know, Clout and, you know, status on Twitter, they're all successful people, and getting advice from successful people is very risky,…”

“Maybe it's, maybe it's not even until after five or ten million where if you don't have capital, you can't all be Atlassian or Qualtrics. Or, and they fall behind competitively. And I think that's the trap of the fallacy of the lifestyle-esque business, right? Where media businesses are different. The information can…”

“if you get, if you're able to invest in a million and the founders are great, you'll never lose money. If the founders are graded a million in revenue”

“My advice to all of them is they should offer to give the money back, a hundred percent. Offer. And I said offer. I didn't say give it. I said offer. A hundred percent should offer to give the money back.”

“And why it's because the diligence is always confirmatory. VCs decide they want to do the deal and they don't want to hear reasons to not do it.”

“BCs want to mark up the company. Often that's the goal, especially if you're at the early stage, right? You want the A to be lower than the B by some margin, and then you want to raise a new fund on the back of the B or C. That's a very different goal from the founder's goal, which is to build a lasting company.”

“And I think what's actually interesting is there's some operators that are very good at their operating job that I think would be worse founders than some bad operators. Right. Uh, and I've, I've like found this. So let me explain that a little bit further. There are people That I would never want to hire again, but…”

“The biggest red flag to me is when I hear a heavy bias towards experimentation. So maybe requiring every change made in the product to be an experiment or over focusing on optimizing, adding friction, removing friction, uh, raising prices, reducing prices, um, versus making substantial changes to the core product…”

“my portfolio company that is working is raising a series A or series B. They don't want to talk to that investor because that investor invested a million dollars in their competitor. That competitor is almost dead anyway, but they're like, fuck them. I'm not going to talk to that guy. They invested a million dollars in…”

“I think it's a very Western centric view of the world To think that you have to be, you know, passionate about the domain that you're in. And I think that ends up actually in quite dangerous territory because a lot of people who are passionate for winning, who are just, you know, hard learners, hard workers and…”

“Because I don't think a VC can truly add operational value to a truly exceptional founder.”

“You know, there, there was a time when folks used to say that, like, endowments and foundations are the most robust long-term partners that exist on the planet. It is just not true. I've heard so many cases where markets turn, things change, and the first ones to leave are the endowments.”

“And so I believe that those companies benefit from growth drivers that are much more meaningful than any execution.”

“the value is not in any proprietary models or data.”

“Autoregressive LLMs basically don't do planning, or a very simple form of it.”

“In the simplistic terms, the model or like, uh, AI is, uh, like a code base, right? It's, it's a bit different, but at the end of the day, it's, it's a code base, right? And so it's kind of silly to say, oh, this code base is better than this code base, or there's going to be one code base that is going to roll all…”

“The analogy that I sometimes like is that on the early days of the web, you could use kind of like something that would Create a website for you, right? You, you could use the equivalent of a Squarespace or for weeks, and that would make you feel good, right? Because really quickly would have like a nice website up,…”

“investors are first and foremost investors, right? Um, meaning that their main value add is to deal around To help you on financial matters. So for example, when, when SVB go down, right? And then to help you to always capitalize the company the right way. So they're, if they're doing their seed, their main job is to…”

“if everything that a company is doing and building can really be accurately described in a single sentence, it's probably too one dimensional. Um, it's probably not Ambitious enough.”

“This is, like, probably contentious, um, but one of my frameworks is, I think that the, like, virtuousness of a company is inversely related to its enterprise value.”

“Yeah, it doesn't exist, right? Like quite literally you're starting with nothing. And so I think that it is a, um, like I think investors are wrong to look for it. What you are investing in is, um, trajectory, right? And the ability for founders to navigate a market and a thesis, right?”

“But in no circumstances do you really want to bring in a VP of sales before you have a seller, because they're gonna come in with the preconceived notions That ultimately might not mesh with, with your particular business model.”

“companies tend to optimize for the power user. And I think that's the thing that you don't have to do. That's like the exact opposite of what you should be doing. And it's very hard to do that well. So if you're just a developer leading a company like that, then it's really very important that you get someone on board…”

“if, you can do it super easy and say, look, I just poach from other funds. I hire people who have been three years in VC. They have the networks. They know how to look at deals. You just get An average index of all the other funds.”

“hybrid is worse than or remote, because hybrid creates concentration, like, there's more power to the team that's close, and it treats the people who are not, um, as appendages, um, and, and, and creates a lesser experience.”

“the problem with power to the edges and bottoms up decision making Is that the value of a product like Shopify, or the value of, not even a product, like a product suite, like, because Shopify has many products, right? And look at Apple, right? Like Apple is like the Mac, the iPhone, the iPad, the watch, the…”

“The minute that person says this other person is the head of product, they've done one of two things. They've either quit their job, or they have given that other person a title that everyone knows is bullshit, and they've basically given that person a death sentence.”

“The valuation to me is the investor's problem. And I just don't like, I don't believe that my sympathy sits for all the VCs that overpaid on things that they did. Like, everybody could, again, back to this, like, you could have said no. If you thought something was too expensive, you could have said no.”

“telling founders, like, put your head down, build a product. Don't worry about fundraising. It's like distracting and annoying. The CEO specifically, their job is to become great at fundraising, and they need to be, like, view that as a core competency that they should take responsibility for, getting better at,…”

“everyone in the ecosystem is incentivized and able to maintain sort of pretend valuations. Meaning the, the investors want to keep their marks where they are. Their LPs actually want them to keep their marks where they are because they don't want to look bad. The companies want to keep the marks where they are because…”

“Look, we believe every company in the world, Is worth its future cash flows. We, we just come from that world. We don't believe in multiples of revenue. We don't believe in, ah, a technology may be worth a trillion dollars or a billion dollars because it might do this. We believe that a business in this capitalist…”

“If you have an investor, private equity or venture firm, that claims that they make a big difference in their companies, that they're there with those companies operationally, that they, they change them in a positive way. And you have 40 or 50, there is no way you have the time to do that. It is, it is operationally…”

“some of the most important things that, um, we should be allocating attention to, um, don't have prices associated with them, and cannot have prices associated with them, and so as a result, we cannot be relying on the market mechanism to guide our attention. We have to come up with other mechanisms.”

“because it puts the burden on others to talk you out of it instead of, like, trying to get smarter yourself.”

“when you raise massive amounts of money early, how are you going to sell for 10 X what you raise? Who's going to buy you for five hundred million dollars? You're dead.”

“As I've said to our employee base here, and as we said to the employees at Netflix, we are not a family. We are a professional sports team, and you will want to work here because you, you will, you will be afforded the opportunity to work with some of the most talented people in the business. And because of their…”

“I think as we're learning and have learned that most companies that are over a thousand people, you can probably do the same damn thing with a hundred people.”

“I do generally think that this desire for speed and this desire to, like, move quickly and hire a lot is a little bit of a false lie. I think companies can be built much more slowly than people think. As you look at value creation over a five to 10 year period of time, I don't necessarily know if the math adds up.”

“You can actually accomplish, I'd say, kind of, 90, 95% of what crypto wants and what people want by actually building this from scratch, by actually looking at the protocol layer and not getting distracted by how it's been implemented.”

“I think everyone should just admit that venture is just capital allocation and private tech and, you know, It's more like being a mutual fund manager than an operator, uh, maybe present company excluded, but I think pretending otherwise is probably anything but a distraction.”

“You get like, you age out of a lot of things in venture. You really do. And if you're not honest about it, I think you're used to end up in a fee milking vehicle.”

“So VCs are legal partnerships, but I think once they're beyond two, They become dysfunctional almost. They have to be dysfunctional. You start to lose or at a minimum, you're only there because of the fun size, because it, you lose all the benefits of a partner.”

“Loss ratios don't matter. Losing, I can't, you know, you don't want to lose a five hundred million dollar check, right? Because it's going to be then ridiculously hard for you to, um, to return that, to return multiples on that fund. Whereas, like, if you lose, in a fund that size, if you lose a five million dollar…”

“So, so, or when early stage investors Get to this point where there's just a lot of paper gains. We, there should be sort of term limits on board seats, like term limit out. If I get to, you know, a 10 X return and can get you some liquidity, then you can move on because the early board members who sit on late stage…”

“In fact, just talking and debating with really smart people who are not afraid of you importantly, which I think is also sort of a Swedish societal trait that you're not so afraid of authority is way cheaper than writing code. Writing code is one of the most expensive things you can do.”

“I actually think product is a hundred percent science and zero percent art, which I know is going to upset some people.”

“Deploying a ten billion dollar fund or, God forbid, a fifty billion or a hundred billion dollar fund like Masa tried to do, right? You already know you will not generate alpha in that. You are getting the beta of the global tech industry when you're investing those dollars at best.”

“I think diversification in many ways is the greatest myth perpetrated on the investing public. The idea that risk mitigation is the equivalent of diversification.”

“I would say the vast majority of organizations, ok, and I'm talking from Facebook and Twitter, all the way down to, ah, GPs. They would be well served, right, to be much smaller, to be essentialists in the people that they have. Because it's very likely that your bottom 20 or 30 or 40% of your organization is dilutive,…”

“I think the greatest entrepreneurs in history, and this is a sort of declassé thing to say, it's not really a appropriate thing to say, but I'm going to say it anyways. I think the greatest entrepreneurs in history, it's this combination of a life's work surface area for the company, a life's work vision that they are…”

“most, um, you know, most companies there, there's sort of a conventional wisdom around startups that you ought to do like one extremely narrow thing. Um, and that focus is like the way to build companies. Um, and I think that at least for Rippling, we've sort of taken the opposite tack. Um, and it's, it's something…”

“Um, in my experience, most of the really strong PMs that have emerged, say on the Google Photos team, um, came from backgrounds with no experience in this domain really at all. Um, like you talked to some of them. Um, in fact, I would say, I would probably go so far as to say that it's, um, anti-correlated with The top…”

“I lost money recently because, um, I invested in a company And the founder was world class. Fantastic founder. But in a market that, hell or high water, you could not make money, and then the business was no longer able to exist. And I learned, actually, market wins. Whatever anyone says. It's not, it's not primary…”

“early days, I don't care at all about what price people pay. ARR doesn't matter at all. There's a hot take from a sales leader, uh, early days. I think the only thing that matters is that you're learning and that you have good customers who are good fits that are going to drive your product forward.”

“I don't think you create that playbook until you have at least 20 ramped AEs, where you have the right to say this is a playbook.”

“I believe that the, the core unit of an investment firm is the investment team. And, uh, I am of the view that if investment team is larger than 10, you are now net value destructive to the overall investment team process and culture.”

“The skill set required to invest at seed is utterly different, different and probably completely incompatible with the idea of being a good growth or public market investor. The reason why is at the end of the day, Seed companies have no financial metrics.”

“In general, I don't think one should be overly price sensitive. Obviously, you know, you have to have some discipline, but the reality is that if you're dealing with companies that are growing at over a hundred percent per year, and you believe it's sustainable, okay, even if you pay up, let's say by 50%, pay more than…”

“So that's another example where I think that You know, a partnership can drive things more towards, uh, mediocrity as opposed to, uh, exceptionalism.”

“Do you know what I think the biggest, most broken thing about LP worlds today is? It's the incentive structures for LPs. I'm speaking to a lot of them who are investing in the biggest brand names, and we don't need to name them, and they have the most egregious terms. And I'm going, what you need to return in terms of…”

“It's a hundred percent about the founders. Not 99, it's a hundred percent. Forget about markets, forget about TAM, forget about even other co-investors. Myopically focus on your relationship with founders in choosing people who are going to build the next generation great businesses.”

“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 it just slows you down, encourages incremental thinking.”

“I'm looking for mal-adjusted people. People will have a chip on their shoulder. People will have something to prove. Versus people that, you know, they are so well balanced, they have to think about a reason to get out of bed.”

“it's actually one piece of advice I give to early stage founders, which is like, don't worry about diversifying. Like, this is maybe controversial in this day and age. If Facebook is working for you, and your LTV to CAC is good, and your payback is good, crank it. Do it as much as you can.”

“only in a situation, and that's what we have figured out, and it's proven by the data that we have, only in a situation where you consistently stick to a 15 minutes delivery window, only then your ability to drive a higher rider utilization can allow you to drive a significant gross profit margin.”

“You know, everyone says SPACs are expensive, but when your stock pops 50 to 70% in the IPO, that's way more expensive than a SPAC, and so it created this window.”

“There's just been a ton of passive success in the industry. So many funds enjoyed success because they happen to live in the epicenter of the greatest boom of entrepreneurial success the world has ever seen.”

“I do think you sometimes have to screen for integrity a little bit higher and I'm Indian, so I can say that, but like, I do think, you know, like from a diligence perspective and stuff, the one thing I try and do is a little bit of local diligence because there have been times when I see deals where it's only kind of…”

“Every VC's math works if you fund great companies. And so it's not about this, like, ownership threshold.”

“I think, I mean, one of the sort of easiest things for usually investors to talk about is how the secret to startup success is focus, focus, focus. I think it's actually wrong. It might have been true at one point in the past. Today, the biggest problems that, at least in like B to B SaaS, the biggest problems that…”

“the power that investors have in companies, you can structure things so that you have board control, you can structure things so that you have voting control, none of those things actually really matter. The power that investors have over you is more than anything a moral authority that comes really from being on your…”

“Turns out for some classes of problems, such as infrastructure management, which is what we do, the wedge doesn't work. Like there's a large amount of stuff you need to do from day one if you want your product to be useful.”

“competition is tough. It motivates all of us, but it's the most destructive force in capitalism, no doubt about it.”

“when we think we're specialists, we think we know a lot about something. If you think you know a lot about something, you have really expert questions, so to speak, to ask a lot of the founders. But my guess is if you were that knowledgeable in And specialized about something you probably should do it yourself or think…”

“I've actually never, ever thought about work-life balance. I don't believe in it. I think it's a failure of modern culture to seek work-life balance.”

“the fact that a company is doubling in value the first day It means that the company was taking money as part of the IPO at the wrong price, at a price that was probably 50% what they should have been doing. And so there's a huge amount of dilution that they incurred as part of the IPO that they probably shouldn't have…”

“I think if you have a really, really good sales leader on the enterprise software side, they should be able to get you to zero to five million revenue or so, regardless almost, of your product.”

“And founders like me, who, who remain the CEO, I think have a huge advantage. We don't have to be as good as leaders as like a professional CEO would be because we're the founder, because there's like something of the soul of the company that's tied up with us. So we have this moral authority, which would otherwise be…”

“there's a thing that I think has infected Silicon Valley, the kind of corruption of data-driven decision-making. People just haven't really looked at the kind of history and philosophy of science to see how rigorous you have to be to have kind of the scientific certainty about something, and they believe that a little…”

“building a fifty billion dollar company, I don't think is substantially harder than building a one billion dollar company, quite frankly, within say some sort of similar timelines. I really think that for talented, smart people, ambition and the size of your vision is the key determining factor.”

“They pushed people to move fast, break things, and challenge all regulations, etc., but in order to be Literally a world-changing company, they had to do that, and they had to have those behaviors. They weren't going to be able to do it by being nice all the time.”

“So it's a strategy, and it's a strategy to cut out the seed ecosystem and other Series A investors down the road. So there are certain firms like A-Six, Z, et cetera, that have ownership targets. And so if you want to ruin their chances of getting the ownership targets down the road, you gobble up ownership early.”

“And I do believe that parental instability or home instability leads to a situation where the smartest and most interesting founders who are strong enough, I would add, sooner or later learn how to master chaos because they had to survive in it.”

“And I think that's probably why venture investors that are younger tend to enter and think about and go along with new innovative models. And I also think that's why venture people at a past a certain age point exit out of the business. They can't learn enough.”

“I think people overvalue perceived diversification. I think you get a diminishing return in our business once you get past five or six investments.”

“I'm always amazed at investors who mock other investors for paying up for companies, and I think there's far more shame in losing on price than winning on price, and no one really wants to say that”

“Sort of this transparency that we were all looking forward to over the last decade to make things just much more elucidated to us, and I think what we're seeing is that actually that transparency breeds a lot of mistrust. These institutions only have their power when there really isn't real transparency into what…”

“women still get promoted for results while men get promoted for potential, and that's what we need to change.”

“That operators don't make good VCs. That's what I believe. I think it's really tough to have two CEOs in the boardroom. I think CEOs, when things work well for them, they're so used to repeating that, and sometimes it can work for another founder, but it's often a different company at a End up repeating some of the…”

“your job is to have your company survive, and if taking that money will do that, then for gosh sake, take the money and have the other discussions later after you're a successful company.”

“to be a partner in a venture capital firm, it's very easy, frankly, to lack integrity because there are no points of demarcation, and you only learn about your fellow partners In very sporadic bursts over very, very long periods of time, largely when it comes to money and credit.”

“You cannot have healthy worth life balance and build a multi-billion dollar company.”

“When I quote unquote consult with people in a partnership model, I'm also in a persuasion mode or a sale mode because I need to get it approved. So I think just naturally, and I think everyone is like that, you're just less receptive. First of all, you're just a little bit less transparent because you need to persuade…”

“sometimes LPs ask me, how do you do diligence, and I tell them I don't, and I exaggerate a little bit, because sometimes I make a few phone calls, but I'm not exaggerating by much, and usually there is, like, silence. They've never heard it before, and then I explain what I explained before, that if I need to do a lot…”

“the fact that you let them Take money off the table actually brings better alignment. Even a significant amount, even if it's five or ten million, they're much more likely to try to hit for the fences and not take the first couple of hundred million dollar acquisition offer because they just cannot say no to a few tens…”

“I think school is often a waste of time, especially if you're in tech. My number one piece of feedback to people is, Get experience. If you want to be in business, start a business. Don't do an MBA.”

“I strongly disagree with that mantra, and I think it's one of the chivalests that gets startups in trouble. The whole point of technology is to find the elegant, scalable approach and And the sooner you do that, the better off you're going to be. When you start to glorify doing things that don't scale, you end up with…”

“Gamification does not really work. Game design works, but game design is not gamification.”

“And number seven, and this is the hardest one of them all, balance high perceived skill with high perceived challenge, and this may counter-intuitively mean making your product harder to use.”

“Oak Tree rejects the concept of waiting for the bottom. It's impossible, intellectually, to know when you're at the bottom. And I think that terms like, don't catch a falling knife, and wait for the bottom, are cover for inaction during crisis.”

“for a lot of these multi-stage firms, the capital that they put into a company in the early stages is just an option value. And if it's just an option value, then if things don't go well, that company is going to have an incredibly difficult time at raising capital.”

“I do truly believe that talent is evenly distributed, so what that means is that every single demographic, you're trying to hire the top five percent of white male men, or you're trying to hire the top five percent of Hispanic women, and so if you have a bunch of chads again, likely you have a bunch of mediocrity on…”

“And so the idea that a diverse portfolio is amongst the VC can deploy this value add and company building at scale. I just haven't seen that happen over my 10 years doing this.”

“My starting point is you have to have the mindset that VCs are going to provide no value. They will all go on and on about the value they'll provide, but what you're shooting for as a base starting point is zero value. And what you're trying to avoid is negative value.”

“When we hire somebody, there's a chance that your company gets better if it's a great hire. When you let somebody go, it is guaranteed your company will get better because at the minimum, you're not stressing about that person anymore.”

“So I think that that's not a great idea. I think there are, and I'll be controversial about it, I guess. I think there are three groups of people you can live near. You can live near your employees, you can live near your customers, or you can live near your capital. And my argument would be that it is far more…”

“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 work with people who are so much better than you at every…”

“if we only back founders who are unwilling to break rules, then I think we're giving away a lot of the upside of our industry.”

“as soon as you raise that first round, or you get to profitability, then put a personal trainer on the company card, put an exec coach on the company card, put a therapist on the company card. These are absolutely legitimate expenses, and you should be spending a company money on the stuff, because if you're not in…”

“When candidates ask about, oh, how long do you guys work, and what is the policy there? I think the reality is that if you look at most startups, people need to realize that it is a fight for survival, and so it kind of needs to be in the spot where you're okay, if necessary, working very hard. And I think that's kind…”

“my general, like, managing philosophy around why people don't perform is it's really the sole responsibility of their manager. You've either failed to give them the context of what you're trying to achieve, or you've hired a person with the wrong skills in the role to do it.”

“if your goal is wealth creation, I think it's much easier to make A hundred percent of the ten million dollar company than one percent of the billion dollar company.”

“any time a venture capitalist opens their mouth, they're probably sending a message to the founder they haven't met yet, and saying that it's going to be 30 years of wonderful glory, all roses, and no thorns, is certainly a better message than screaming, the skies fall.”

“Just know that if you do that, your chance of basically, like, having outsized, non-normal success is almost zero. Like, at the end of the day, if you really want to achieve more than anyone else, if you want to be not normal, you have to work not normal.”

“Why wouldn't we instead go raise some additional capital from people who adequately value it or value it at least at a higher rate and instead convert that money that we get from investors into higher salaries to make us more competitive? And so I'm surprised to see that more companies aren't doing this, um, because…”

“oftentimes when people talk about diversity, this whole notion of quote, lowering the bar, not lowering the bar comes up. But when you actually sit down and look at it, most groups that are, have not been very diverse or even set a bar in the first place.”

“I hear people tell women not to join a firm as the first female partner for fear that they will be, quote unquote, the token partner. I think that's I don't know how we're gonna change things if we shun the 74% of U.S. firms who don't yet have a female partner. I think we should really be helping those that are raising…”

“spending time with associates. I think that's Tends to be a waste of time. And I think meeting with investors to give them updates, I think that is also a waste of time.”

“VCs don't really understand insurance. So they don't understand the risking that was done behind the scene. To lower the risk and actually bring you to have a customer. They don't understand how you manage your claims, and what you've done on the reinsurance, and what is filing, and what is a policy management system,…”

“Usually, if there is a partner from a top fund, there is a tendency to give overweight to his idea and decision point, where it's not substantiated by the merit of his idea, but just rather from the fact that he came from Sequoia, he came from Benchmark, he came from Excel.”

“for a CEO, I would probably change it to something like always be building. Put your time where it matters most at that moment, and fundraising is a component of that, but on a day-to-day basis, week-to-week basis, there's a lot of other areas that I think will be more important to have a bigger return in terms of a…”

“For us, right? But I think for us, like, pedigree has sometimes led us astray. We are, because of how we've grown and how we've sort of been brought up, we like people who are hungry and ambitious and, you know, who have a bit of the chip on their shoulder. And CB Insights, you know, as nicely as the newsletter is…”

“Yeah, I think what it does is it forces venture capitalists to make decisions that aren't entirely informed. So if you actually read a white paper it's basically 30 pages of really technical information that requires diligence, which you couldn't possibly do in a couple days worth of time, and so what I'm seeing a lot…”

“And the reason they move up market is that the fees for larger funds always outweigh the performance of smaller funds. The people running these funds have incentives to raise larger funds.”

“Most tech VC firms look at D to C, direct-to-consumer, as a way to scale a business efficiently. That is completely wrong. It is not a channel to scale a business. It isn't certainly not a channel to scale a business efficiently. DTC is a great channel to test new products because you can cycle through products much…”

“I think pattern recognition is another name for intellectual laziness, right?”

“Yeah, I generally think decentralized teams won't work. I think in the very, very early days of any platform, they can work, and it's because there is not that much competition, and a lot of what you need to build out is infrastructure, and you have a small number of engineers that can communicate with each other to…”

“First off, I don't think seed stage companies should have boards, I really think that they can get misdirected when all they really should be focusing on is talent aggregation and product market fit.”

“I actually disagree with Fred. I think if CAC and LTV is a focus on a series A deck, I essentially just want to throw the deck out.”

“if you don't listen to the board, you might get fired. If you do listen to the board, you will get fired. And I think that's true.”

“And my general posture is that when you're looking at a follow-on investment in a company, you should either have the bias to do more than your parata, or you should have a bias to do less than your parata for whatever the reasons are. I think parata is a lazy posture, unless that's what's required to get around done.”