The Wisdom Wall

“I, I actually have a lot of coaches, but I've chosen all them, and I'm not coachable by a VC who's never held this job, who never sat in this seat, and so I, I guess it's not exactly advice, but it was implied advice of, you know, I should pretend that I'm going to learn something from, uh, the person with money or the…”

“There are some benefits to having flexibility and hybrid, but creating culture and creating, um, collaboration and learning, that's not one of the benefits. You know, you really have to get people together to be able to do that”

“But for 99% of CEOs, my suggestion would be just avoid it at all costs and say, We're going to try and create economic security for you and your family, such that on weekends, whatever you want to do politically, recreational, if you want to be a DJ or you want to go to a, uh, you know, save the whales rally, that's…”

“It is extraordinarily difficult to maintain a monopoly. That's not coercive. So like, you know, the only real monopolies that exists can be granted by the government and can be coercively maintained.”

“And my personal view is that we have to tell people you can't, right? We're a fifty-fifty country. You think you know what the person in the next cubicle thinks or the next Zoom box, but you might be wrong, right? And so how do we evolve to a place where we can respect That people want to be community activists or…”

“your moral compass should exist at a higher level than, how can I make the most money? And so you may have to, you know, you may have to take stands. And to take an extreme example, um, if Apple and Tim Cook cannot take a stand, who can? Who can? You're the most freaking valuable company in the world, and you cannot…”

“One of the things that Heather Champ, who is a community manager, the first community manager on Flickr, one thing that she says repeatedly is that what you tolerate is what you are. So if you tolerate white supremacists on your platform, you are a platform for white supremacists, and you just have to accept that. And…”

“I now think that the correct organizational structure for building an AI organization is actually to eliminate the concept of having a separate safety team. Because by creating a safety team, you're now defining this is the unsafe team, this is the safe team. We'll have the safe team keep the unsafe team in check.”

“So now what has happened is there's been this view that you should bring your whole self to work. And now we're being forced to crawl that back because your whole self is maybe not what we want in work.”

“Frequently, you have to scale first and figure out your unit economics later. In fact, putting off this question is the prudent route for anyone playing in a winner-takes-all market.”

“This is why I tell people in many ways, it is easier to start a hard company than an easy company.”

“For scale companies, the rule is provide whatever service you can as long as it doesn't slow us down. And that may mean no service.”

“It's 49 parts performance and 51 parts hospitality, and that's what you are going to be judged on, that's how you're gonna get paid, that's how you're gonna get your bonus, and guess what, guys? In this business, the customer is going to come second. And by the way, the customer is not always right, because no one's…”

“I have been known to tell founders to consider shutting their business down rather than take money from this kind of investor. Better to fail now than to do so in three years in a cloud of acrimonious smoke.”

“And then we use the data to inf to impose uniformity on the stores. And that really is the death knell for us. It works in almost every other branch of retail. It doesn't work in books.”

“What I found with older people is, like, there's really no ego. They're not, he's not trying to build his career. He's just, like, trying to do something meaningful and fun. And so to pair him with somebody with no experience and a lot of grit was like magical. I called it the barbell strategy. So there's like, you…”

“the best product makers, the best masters of the craft, Are the best at copying. And, and they have the least ego around it. And the most junior amateur people feel the need to change everything, and they're the worst at copying, and they fail for the wrong reasons.”

“So, so I do think that everyone kind of becomes full stack when you, when the stack's automated and it's, and it's just promptable. And so I, and then it gets down to taste.”

“do not build it right. Build a culture of building it wrong. Do not, build it right, presume some level of success. I love Eric Ries. We've had great debates. I, I'm in the same spirit, but, but that word viable is actually hurtful because viable also means hope of viability. And what you want is not viable, you want…”

“As opposed to creating building blocks, we wanted to create solutions in verticals. That I think is a mistake as technology shows in the beginning.”

“I think curiosity, uh, willingness to adapt is more important. I think we're getting hung up on, I need to know AI, like a PhD in computer science. I think that's the wrong thing, because that's for the inventors of AI. That's not needed for the deployers of AI.”

“We will completely acknowledge that Mythos is way easier to use than the past. So what it did do was it opens up the attack surface to where I don't need one of those hundred experts to go do it. I can now do it with somebody with average skills.”

“And then yes, there's the option to go IPO, but then you don't have a distribution partner. So it's just a really tough situation to be in, in beverage.”

“the loneliest people I ever meet are CEOs, the loneliest people I meet. And the reason is because it's all deal, no real. Because real friends take time and you don't, you're not compensated for it.”

“I think now the way we see our product being used by product managers, for example, product managers are some of the best vibe coders because they're really good at taking problems and breaking them down into their constituent parts, uh, and communicating them very well to the machine. And then like the machine can,…”

“And if you're going up against blitzscalers, it's very hard to succeed without also blitzscaling because the blitzscaling will set the market. It may blow up, but we'll set the market. If it blows up, it'll probably blow you up with the market.”

“Google search doesn't have network effects from its search engine. It has scale effects. But it's AdWords is where the network of it.”

“No, and that's part of the reason why it's an absolute mistake. I literally correct people that I talk to them and say, oh yeah, I, you know, Claude's my best friend. And I'm like, no, friendship is a bi-directional relationship. Like part of what is actually essential in friendship is like, I show up going, oh, I've…”

“if you get a serious, you know, kind of medical concern, if you're not using one or more frontier agents as a second opinion, you're making a desperately bad mistake, right?”

“And there's this fallacy in that, you know, economies of scale will lead to an improved gross margin and it just doesn't happen.”

“And the thing that has changed is that they are now forming opinions or arguments based on how they feel in that moment. It's not to do with what's being said or who's being said. It's based on how it makes them feel.”

“for such a long period of history, we've trusted the technology to do something. And now we're testing, trusting technology to decide something and to create something. And the reason why this is so important for entrepreneurs and designers and business leaders to understand is that you've got two sides to trust.…”

“So the fact that it can't absorb emotions, that it doesn't get flooded, allows it to be empathetic in a way that humans can't, like whether you're a therapist or whether you're a doctor. And the interesting question is whether, where it stops. So it's really good at cognitive empathy, but it can't do what we call…”

“Judgment might just be part of our experience, and I'm not saying that that's not a good thing for you to take as a first step, but it's like saying that the be all and end all of sex is masturbation. Yes, it's very freeing. There's no judgment. You don't feel about how you look or how the other person might feel or…”

“Nowhere on the grading sheet does it say if they made it to the other side or not. He goes, we measure the characteristics of good leaders. And he said, we understand that sometimes good leaders suffer a mission failure and sometimes bad leaders enjoy mission success. So the success or failure that they have in the…”

“The third space, the library, the neighborhood, the community center is the space where people used to come together around a shared mission with people that are different from them, which work has done as well. And once you lose that, you lose the space where you cultivate tolerance. And once you lose the space where…”

“there is something called too big to buy. And so I really, cause you know, we were growing really fast and, and so the worry is once you, you know, get to like 202 50 in terms of, um, revenue, then you're gonna be, you know, people might want a billion dollars for valuation. And there just aren't that many people who…”

“They're so good at making money, they shouldn't be trusted to do anything else. And unfortunately, they've done a great job of personifying themselves, and we believe them, and we believe that they're actually trying to connect the world, you know, make the world a better place. No, they're not. They're trying to…”

“My litmus test for evaluating the disruptable, how disruptable an industry is, is I look at its price increases relative to inflation, and whether there's been the underlying innovation to support that increase. And the, the two sectors I think, I see are most disruptable by those metrics are healthcare and education.”

“You can never get all these things in these complicated systems to zero, so the better thing is, make sure that you've got baseline good, and then be improving constantly on those, so you, you, you launch anyway.”

“Hire the smartest people you possibly can and put up with them, right? Um, and we all understand what that means, right? But you really need them for competitive advantage.”

“if the smartest person in the organization isn't aligned with you culturally, that can actually be pretty dangerous. And so as an organization grows, you make allowances certainly for your most talented people. But if from a cultural standpoint, they're not aligned with you, that can be quite destructive.”

“one of the big learnings is we are not a country. Um, you know, we are a community platform, and we're also a business. This is a place that people have to want to be. You don't, you know, by and large, you don't choose where you live on Earth, um, but you can choose whether to be on Reddit or not, um, versus something…”

“founders don't care about moats. They don't have anything to protect. They have the ability to disrupt by bending the arc of the present to a different future.”

“the first thing I've noticed is the AI startups that pitch me much more often have inflections than insights.”

“there are fields where the people in that field are very smart, but if they could be completely digitally specified, uh, those people are more at risk than people who, Do things that can't be completely digitally specified because then AI cannot be a substitute as easily for, for the human activity.”

“how many times do you realize that like all the people that work on stuff, there's maybe one evil genius that's doing kind of everything and everybody else sort of takes the credit. Then you put them on their own. And it's like, cause I remember the first presentation they gave to me, I was like, oh no. Like it didn't…”

“you don't want to let your rivals define the nature of the race you're in. Like, we beat China to social media, which means we beat China to sort of a misinformed, polarized society, uh, with mental health issues. We, instead, what we want to do is figure out how do we race to the most strengthened version of our…”

“Grit is not enough. You must have your situation as your ally.”

“the building of a sports team is a lot easier than the building of a technology team, and the people that are willing to help you do it are vastly larger than those that I experienced when I was building something in tech, because when most businesses are built on the internet and everybody can be your competitor,…”

“If you said, well, I could have a CEO, With maybe who's a little less proven, but has the refounding mindset, you know, um, or I can have a CEO who's proven, but doesn't have the refounding mindset. Personally, I would always opt for the refounding mindset, right?”

“Yes, you know, this algorithm's a little better. Yes, this algorithm's a little worse. Yes, this data set's a little better. Yes, this data set's a little worse, but it's the scale that is primarily driving. And so it drove it in the large language models, hence large out of language models. And it's what's driving it…”

“we will not sacrifice, ah, the entrepreneurial spirit in the name of synergy. So we are going, another way of saying that is, we are going to tolerate inefficiency in the name of supporting Entrepreneurship. And that I think is the, um, the secret sauce.”

“What I can tell you is that Star Trek is a waterfall that keeps rolling downstream for 30 years in terms of licensing. So it's not just a matter of saying, okay, you have to decide in this quarter whether you're successful financially. My argument is you have to think big picture. You have to assume, based on the…”

“if you talk to someone like Mike Moritz of Sequoia, Mike Moritz of Sequoia will tell you that the richest vein for Sequoia's investments, and there's no company, no VC that has, you know, created such value as Sequoia. It's two people creating the product that they want to use. They are an unproven team in an unproven…”

“many times when, if you face, like, rigid recommendations for, I need your internal rate of return, I need your return on capital, I need this kind of projection. In a sense, the investor is telling you no, and is trying to put these fences up in front of you, hoping that you will go away quietly.”

“if an investor is truly interested in your business, they're not going to throw these fences up in front of you. What they're going to be thinking is they do not have a world-class team, but I at Kleiner Perkins or Sequoia, I can tap the greatest talent in the world. I can fix their team. And if the investor concludes,…”

“What you want is some people going, you guys are out of your minds, and some people going, I see it. You want a polarized reaction.”

“There's a standard way of thinking about this in Silicon Valley, which argues that large online platforms are inherently objective and do not have values of their own. I think this is incorrect. All platforms are, in fact, value-laden.”

“For example, on the Facebook side, they say, well, what people click en masse demonstrates their actual preferences, what they actually like, and so we have a democratic platform that promotes what people click on. It's a reflection of actual behavior and preferences. You might reply, well, if you let that run wild,…”

“what I learned from my time at Tinder was the minute you encourage someone to use a piece of technology, You are inherently responsible.”

“The principal issue of any system like StackRank has is it doesn't leave room for judgment, which is who said that a team cannot have all about average performers? We all know that performance is in some sense relative. The world measures us that way. But at the same time, you can have periods of people performing in…”

“Because asking for a six month pause, the people who deeply care about humanity, they all slow down and the other people don't. Your letter has a net negative impact.”

“The minute when you actually make painful changes is when the organization in a turnaround knows you're dead serious.”

“The other thing I learned, and this is from Lou Gerstner, Who said, who had written a whole book on this, and his IBM turnaround, he said, you only have six to nine months to change the culture of a company before you're stuck with it.”

“if you're not embarrassed by your first release, you released it too late.”

“I believe it's more important to have a hundred people who love your product than a million people who just sort of like it.”

“That's really important because startups, once they get big enough, can only grow by word of mouth. All the growth hacking eventually stops working.”

“The hard kind of blitzscaling is where you try to start scaling up before the product is really great, and then most of your effort in scaling is to generate demand. So I think the number one most important insight about how to blitzscale is that the good kind of blitzscaling is when you are not having to generate…”

“Everyone's like, well, I'm just going to get a lot of people to like me, and then I'll figure out how to make them love it later. In practice that's really rare. I would challenge you to think of an example.”

“In fact, if you're not embarrassed by your first product release, you've released it too late.”

“Even if not every single release is perfect, I think you're going to end up doing better over a year or two than you would be if you just waited to get feedback for a year of all your ideas.”

“on a day-to-day basis, a lot of the decisions that I'm making are like, okay, is this going to destroy the company? Because if not, then like, let them test it, right? I mean, it's, if the cost of the test isn't going to be Super high, then in general we're going to learn a lot more by experimenting and by letting the…”

“And glue people are very nice people who sit between functions and help either side, but don't themselves add a lot of value. And I thought, these are nice people, but we don't really need them. We can have these groups talking directly.”

“we actually see through visual touch points that four or five people can inspire, mentor, and invest in practically the entire ecosystem.”

“Every successful founding team at Google, Facebook, wherever, spawns its own little network, and there's nothing magical about the networks in Silicon Valley. They can take root just about anywhere that you have a few successful entrepreneurs willing to pay it forward.”

“An idea is its most vulnerable in its infancy, and that's also the moment in human nature we want to immediately turn to our right or left and tell our coworker, our friend, our boyfriend, our boss, you know, I have this idea, and out of love and concern, we hear a lot of things that stops us right in our tracks.”

“Because the job of a CEO is often just to come up with a story that enough people believe that you can make something happen in the world.”

“this, by the way, I think is the greatest software development methodology that's impossible to replicate, which is, don't think about what you're doing, have no ego, there's no speculation, there's no, I can imagine a user would want to, to spend the minimum number of minutes addressing the most aggravating problems…”

“You don't just want to be the first mover into a new market. You want to be the first scaler. You have to seize every last opportunity for growth, even if it means serving customers on a delusional scale.”

“What's important about this story is that it's full of unforced errors, and I would argue that those errors are fine, so long as you're pursuing a massive growth opportunity. When you're moving fast, you can't say, oh, we're going to study this for six months, we're going to be perfectly wise and avoid a lot of basic…”

“meritocracy is an important ideal and a dangerous religion.”

“I often find that to reinvent an industry, you do not take inspiration directly from that industry, that you need to look at orthogonal industries.”

“And it's actually not unusual for industries that go through a period of crisis where you circle the wagons, and what I saw was we'd love to promote this woman or this person of color, but we can't take the risk. So everybody reverts to their comfort and uses that excuse, the fact that we're in the midst of this…”

“Recruiting is a constant drumbeat, and that goes extra when you're hiring at scale. That's why I believe you should always be recruiting. The more your business scales, the more tempting will be to delegate this task to others. Resist that urge, and never stop personally scouting for your next eleven-star employees.”

“If you're going into the airline business, make sure that the people running it are going to make sure it's a very safe airline, and you get the best technical people on board. But then, on the planes themselves, you don't need the cabin crew spent 20 or 30 years flying on other people's airlines. Go look for people…”

“for 99% of companies that start up, you're not going to get an investor and you live close to the people who are going to be your customers to help your business get started, particularly if it's a service oriented business.”

“Raising money is not an accomplishment, it's an obligation. It's more about getting someplace where you can solve a problem and do something unique and special, and once you get to that point, yeah, a little bit of investment, because the less you take, the more you own.”

“If you have a C culture, you can revise it to a B+. But a C culture will never become an A culture. The only way you get an A company culture is by creating it at the beginning and preserving it.”

“Deliberately choosing and building a team at the very outset will carry through the organization from the get-go. I mean, you can, you know, a lot of companies try to graft on these Diversity initiatives, 12 years after the founding of the company, and those tend to not be very successful. It's because the culture has…”

“What you want is some people going, you guys are out of your minds, and some people going, I see it. You want a polarized reaction.”

“There's a potential mortal risk in being conservative. You might think you're best serving your investors by being as efficient with capital as possible, but that's actually not true. You reward your investors by creating a successful company, and raising only twenty million dollars might mean losing the twenty million…”

“Tech businesses absolutely need to raise more money than they think they'll need. They'll need that capital for all of the unknown pivots, whether it's new customer needs or competitive attacks.”

“Things are always more expensive than you think they are, and they're always going to take more time to prove out, and you're going to need more optimizations and more loops to correct things than you think you will. That's why we just say, roughly speaking, it meant to act like you've got half because you've got to,…”

“I think startups raise way too much money. The less money you raise, the more control the company you keep, but more importantly, the more constraints you create. They develop a scrappy culture. The scrappy culture requires you to build more novel solutions, use fewer out-of-the-box software things, And you end up just…”

“If you ever take the CEO onto the board, you will be fired. It's just going to happen. You may win, you may lose. Whatever happens in the battle, you will be fired.”

“The lesson from Tribe that came resoundingly out for me and still stands out, that as entrepreneurs, part of the journey that we're on is learning how to separate our winning instincts from our losing ideas. I think as a rule of thumb, if you're a good entrepreneur, you can assume that your instincts are right 95% of…”

“And I generally said, if half your audience clicks on it, you pretty much know it's an idea worth pursuing.”

“And I've adopted this hiring rule, which is that you should never hire someone to work for you unless you would work for them in an alternate universe.”

“often when companies need to take Like two years or so to rewrite their whole app or software for a new platform. They believe that they can't slow down feature development. So they do two things at the same time. They try to design a new product while rewriting the existing product. And I think that that ends up…”

“it works much better at smaller companies than it would ever work at a large company, right?”

“One of the things you lose when you are not physically in the same city, in the same room as other people, are those chance encounters and also those planned encounters where you get together and you hatch an idea.”

“Remote work, when it does work, is, ah, when there's a very intentional effort to bring people together physically, all in one place, in the same room, breathing the same air, and having a synchronous experience, but also having some leeway, you know, that informality, the sort of spontaneous conversation”

“It's a much nicer way to work and it's much more engaging and much more empowering and all of those good things, but it's so much more difficult that often people resist it, particularly when it's difficult. We'd rather have the hierarchy. Just tell me what to do, please. But I think ultimately, if you can get to a…”

“travel, making that part of your, uh, you know, post-college experiences, It's like the world's greatest classroom. You learn a lot about empathy. You learn a lot about your country. When you come back, you know, you've had a, a better formed existence. You're probably going to be more attractive to someone who's a…”

“There's the conventional world of sports, which we play a little bit in that world, but we can't control whether your team wins or loses. Right. But what we can control is the show. And if we build the rules, we make the rules of the game, we make the rules of the show, people can leave and have a great time every…”

“So what they don't talk about is the, You know, the phone calls where, um, if you guys don't do what we say, you probably gonna be blackballed. You probably won't be able to raise money again. You know, it's a, you're dealing with these powerful venture capitalists and, um, they can get in your head.”

“Generally, either you're sick of the business, like you're like, get me out of this thing, um, or you need liquidity.”

“so if we want to be a brand, like an iconic, beloved brand, um, we need to be in retail.”

“I used to believe that thinking about your legacy would be a worthwhile use of time. I, I no longer believe that at all. I think it's far more important to think about the responsibilities you choose right in front of yourself to make, to make good on while you're here.”

“So what I always go to is, I want your 50% probability win. I don't want the 90%, because if you tell people I need to be 90% certain, that's no risk.”

“And then in the end, there's a gut feel, because if it's just research, then everyone's gonna have great packaging. Cuz you have the same research agency, you'll show them 10 designs. I think finding the right designer and going with your gut is a big part of what makes packaging cool.”

“Most people, the problem they have is that they don't have enough money. It's not, it is that, I just want to say that plainly.”

“What became really clear is that being able to scale fast meant how quickly could we talk to anyone and figure out what kind of money help they needed, and then deliver the best version of that. So we kind of broke some of the startup-y rules, where we didn't get really specific.”

“you can optimize for the short term if you want to make kind of the best kid. Uh, but that often undermines long-term development, whether it comes to learning an individual skill, picking a career, and so forth.”

“being to execute on one thing, and do it better than anybody else, Is gonna be a recipe for success, and it ended up being there.”

“when you're building a brand, if anybody else can line extend their way In, and compete against you. You're really going to struggle to compete against a big company unless you, you can create a great, you know, a huge lead.”

“And I think that's go goes back to why some of these companies can't innovate is because they have to rely on the consumer and consumer research. To be able to make decisions and drive their vision, which is always going to be a rearview mirror.”

“people have made a fortune by selling too soon. It's better too soon than too late.”

“I think that the, the founder product insight is irreplaceable. And so much of these businesses today are product led that we want to back founders who are unique and differentiated there. And we want them bought in for the journey. And, uh, and tapping out and hiring a replacement is hard. It's destabilizing and…”

“Don't try to be the operator. Um, and, and that manifests itself in a few ways, but one of them from the investing side is don't find things that are doing okay and going to fix them so that you go from, you know, good to great. Go find the teams in the business that's already great and make them excellent or help them…”

“When I see pitches, a lot of people put their bios and their experience up front. I'm not a big fan of that. I, I, I want people to tell me what the idea is, what the value is, and then let me know who you are versus who are you up front.”

“One is enjoyment, which is not pleasure. It's pleasure plus people plus memory. It's, you know, pleasure doesn't lead you to happiness, The pursuit of pleasure leads you to rehab, but, but when you actually add people and memory to it, you, you transfer the experience of the pleasure into the prefrontal cortex, which…”

“The left hemisphere of the brain solves complicated problems, which is problems that are, they're hard to solve, but with how to and what knowledge, you can solve them once and for all... The right side of the brain deals with complex problems. Complex problems are why questions that don't always have answers. They're…”

“What's happening in modern life with the hustle culture, the engineered culture that we live in, where the tip of the spear is the, the way and amount that we're using tech in our lives. Is pushing us to the left hemispheres of our brain, where we don't deal with, we can't even conceive of, right hemispheric questions.”

“Biology has become editable, writable, readable. Which means that we can design, uh, anything in the physical world in a way that we've never been able to before.”

“What people don't recognize is that the same thing exists here in Maryland, in the United States, in the West. Um, the difference is it wasn't built by a single government. Um, it's a corporate panopticon.”

“no companies wanted to standardize a single vendor. It's really not as scalable, right?”

“there's no game in the world that starts with a manual. Right? So if your program is starting with a manual, you've, you've already sort of lost.”

“And by the way, if you try to lock that in, you're essentially going to be stealing your children's future, because the other society will move ahead, and then yours will now have put them in a very disadvantaged position.”

“Elon said this a long time ago, the only moat is continued innovation, rapid progress, and I think that's true in, in AI today.”

“people are no longer sort of attracted to these, you know, bland corporate brands and the faces behind these companies. I mean, thanks to LinkedIn and things like that are becoming more important than the brands themselves.”

“The goal when you have a paywall is if someone's not going to subscribe, you want them to read the article, right? And if someone is going to subscribe, you want them to pay to read the article. And the problem is you can't know. You can't like interview every person about their subscription propensity and whether…”

“you're putting the pressure on the person who has the least amount of information. So if Julie on your team thinks she might be underpaid, she doesn't know anyone else is being paid, and it's her job to fix it, like, it's just the wrong approach. What you need is that the company that has the information needs to be…”

“what no one has figured out is how do you really signal trustworthy information?”

“So in that meeting, you'd actually want people to be defensive because they're engaged and that's a sign of trust.”

“I don't actually think That how do you get people to trust us is the problem. I think too much trust is the problem is the first thing I'd say.”

“art is by humans for humans about being human. It's not about Ideas. Because ideas are constructs, and humans are not a construct. They experience ideas, and they have emotional responses to them, and I think art is that combination of an idea that, that elicits an emotional response.”

“even if it's actually inferior to humans, the access that more people get it is better than nothing.”

“You know, the vast majority of companies shouldn't necessarily try to do good. I think what they can do good is do good by their team. Um, make sure what they're doing does no harm. Um, but creating a big business in its own right that, that serves customers, um, or serves businesses is, is a great endeavor and a…”

“you cannot have long-term sustainable success as a single product company. Period. I mean, you're either gonna be disintermediated or you're not relevant to a consumer on an everyday, ongoing basis.”

“A lot of people put a lot of money into Google search for a long time, believing that's how they were acquiring customers. But the question that they were typing into the search box in the first place got created somewhere else.”

“Why do affluence and eudaimonia have to be in conflict? I would say, I don't know. Ask God. You know, I don't know. Like, ask the universe. I am not here to solve this problem. I'm just here to report the facts that those two things are in conflict.”

“This is why the Unilevers, the Nestle's cannot do what we did, you know, cannot Started even with all of the resources in the world. Like when you get big, your, your brain changes, you know, you're really good. You become good at running big organizations, but harder at starting something in a scrappy way.”

“The chances of a competitor, whether it's a big potential acquirer or even another startup, learning something from that conversation and going and replicating it is, is very low. It's not zero, but it is quite low. And the potential upside is really significant.”

“the best boards are actually managed by the CEO and founders. Um, the board isn't managing them.”

“don't put a board together until you need one. And sometimes it's perfunctory and you feel like, well, I have to have a board. Think hard about, if you're raising a seed round, do you really need a board yet? Maybe you don't need a board member until there's the Series A.”

“even with companies now trying to bring a, elements of artificial intelligence into how they run their business, it's not plug and play, because the data isn't secure enough, or It's not a hundred percent accurate. It's 99.9% accurate, which is not enough if you're making decisions. It has to actually be a hundred…”

“And what most companies and people do is they aim all of their advertising, all of their efforts, all of their sales towards the majority, because that's where the market is. Unfortunately, it doesn't work. You have to keep throwing money at it for it to work, right?”

“The true missionaries will take less money from a less famous venture capitalist than the big money from the big venture capital so they can tell their friends, look who I got, you know, uh, Or find alternative ways, bootstrapping bank loans, credit card debt, you know, um, because they don't want anything or anyone to…”

“With the people that are your friends, if you're not every so often talking about the friendship, you're failing as a friend.”

“We know that the danger of an AI friend is forget about the dopamine that's in there as well, but now it's hijacking our oxytocin, which is all the warm and fuzzies. So when I have real emotion, With my bot, those emotions, they're real. The, the, the chemicals are flowing. But for the fact, the bot has no feelings for…”

“And if a, if we just simply rely on AI to make the outputs, you know, learning to be a better prompter, isn't going to make it doesn't that there's no, there's no torture and growth requires, requires struggle.”

“People should come back to work in person, maybe not five days, but that's not enough. Because the people who are coming back are socially atrophied. The people that are coming back have been de-socialized and have lost skills and the younger ones never developed them.”

“you don't necessarily need to know what people are fighting about. Because you want to find out what they're fighting for. What they're fighting for is the form. What they're fighting about is the particular subject du jour. You know, today it's this, tomorrow it's that, but if the, if the fight is that I constantly am…”

“When you are constantly fed predictability and frictionless delivery on demand of your every delight, you become incapacitated in your ability to tolerate uncertainty, unknown, unexpected, frustration, conflict, experimentation, making mistakes, Then figuring out what you can be responsible for and how to change it.”

“I think that both work and home today are carrying the burdens of a ton of needs and expectations that used to be distributed in religion. Extended family and communal structures. And all these needs have been transferred into work and into love, which are the two primary poles of our lives. So, um, we demand, you…”

“Well, I think the biggest solution I've seen to shrinking the empathy gap and look, I'm not going to say that it's perfect because I don't labor under the delusion that the social internet is good news, but, uh, is the social internet. Um, you know, people become, people become proximal to all kinds of suffering that…”

“one of the most effective ways the US has expressed its power over the last 60 years is through its generosity.”

“in hindsight, actually, the reasons why it worked out, I actually think three, if you have, um, a co-founding team of three, it's actually great, because, I remember, and I remember someone told me, like, oh, three is one too many. But I think it's great because if, there's always a tiebreaker. So if two people, you…”

“I think otherwise software alone is not going to change. What is an incredibly human experience”

“One of the things that is frequently challenging and frequently counter predictive for successful projects, in my experience, has been when you raise way too much capital initially. And that then says, well, it's because we're going to try everything and go really bold and, and, and, and, and do the whole thing from…”

“the natural thing for regulatory agencies is say, I get penalized every time an error happens, and I get no upside for things working more efficiently, or working more on target, or anything else, so I just throw in every possible thing that could be answering a negative. And that's how it works over time, whether it's…”

“you should do regulation, When bad regulation is better than no regulation, whether it's an industry, whether it's a specific kind of thing, but you shouldn't just like delude yourself that you're super smart and a technocrat and that you know how to do this regulation in a way that's so great for the industry that…”

“Um, and so even in this kind of hallucination case because of the research, it was actually still an accelerant. It just is an accelerant in a way that kind of proves the point from my earlier book, Impromptu, and also part of what I'm trying to say in Superagency, which is, Human amplification. Like, it's, like,…”

“And so board decks are very useless other than the financials, because it doesn't really tell a story. If you can't sit there and communicate what you're doing, why you're doing, what are the top three areas of focus, why those areas of focus are so important, you will never be able to move the board forward, let alone…”

“USV, I think they're good at a lot of things. They are very, very, like, market and idea driven. And, you know, like all investment theses, sometimes it works, sometimes it doesn't, but I think their, their, like, fundamental world view to me was if you pick, or if an entrepreneur finds the right market, They will win.…”

“if you are growing and you feel like your product market fit, start at 20, such that you don't You don't have to start later when, when everything is kind of even more chaotic.”

“We said, people who use AI, this is an augmentation tool and it will potentially replace people who don't use AI.”

“instead of Choosing my, my co-founder based on who I love and, and you know, who's close to me right now. Why don't I go first, try to find a great idea. And then once I have the right idea, then I should go find a co-founder that really helps me solve the problem that I'm trying to solve. And it's probably that best…”

“The science shows that that's a terrible strategy and that what we actually need to do is try and find a way to make it enjoyable, to pursue our goals.”

“And if you're, if your desire in life is to exit, then you should be doing something else because your motivation is in the wrong spot. Um, and that means, uh, you're going to be making decisions that are never in the best interests of the one, the one great thing that must be created.”

“But individually, these, these groupings of technologies, these general purpose technologies aren't important. It's the convergence we discovered that matters. And what's happening is, um, improvements in one begets improvements in the other. So there's this sort of flywheel effect.”

“This is your first challenge, and I know it feels like the hardest one, but if you can't solve this problem, You're not prepared to be an entrepreneur.”

“Invariably, 20% of the things I'm doing are things that someone else on our team could do as well or better than I do it. And every time I do that, it's an act of generosity because someone else gets to grow. Every time I don't do it, it's an act of selfishness. But I think even more importantly, every time I don't do…”

“if you can be really kind of, I hate the word authentic, but if you can be a bit raw and unfiltered, I'm profane and vulgar. It turns off people, it turns off advertising, but I think people appreciate it, and it's authentic.”

“generally the way we evaluate culture through a shareholder lens, quite frankly, is retention. And that is, you should have eight to 12% turnover a year. And if you have a lot more than that, something's wrong with the culture of the compensation.”

“boards basically are there for two things. They're there to hire and fire the guy or gal running the company. They're there also to decide if and when to sell the company. That's about it. And maybe make sure the chairman of the audit committee is smart enough to know if there's fraud.”

“And the whole like habits of highly successful people thing doesn't always correlate with people who are considered highly successful.”

“you have to have a go to market strategy and distribution strategy, you know, which is, you know, as important as your product in most cases, um, sometimes even more”

“Like in a venture thing, what you're kind of ideally looking for is that day one of the investment, everyone thinks you're a little crazy. And then at like year two, it's like, oh yeah, that's credible. And at year three to five, it's obvious.”

“listen, we don't have a PR problem. We've got an us problem. Like, first we have to fix ourselves, how we, uh, act, who we promote, etc. Then the PR can follow, because ultimately, especially in this world, the substance always comes out. You can't pretend anymore.”

“Because, you know, if you crowdsource, if you get the average of 20,000 people what their opinions are, you kind of get to the average opinion.”

“Well, first of all, very rarely. You know, my belief is that leaders should focus on running their business best they can and make that their primary accountability.”

“I wouldn't recommend it, what, the way we did it, because what we did was, like, we were basically now running two different organizations. One was, like, franchise, and one was company owned, and so the needs of those two stores were quite different, and managing the, the franchisees and those owners, our partners,…”

“getting feedback from your peers like that is way more powerful Than getting feedback from, you know, the company or the man.”

“If you, if you look at the incentives of social media, a lot of it is about, there's, there's a strong kind of, there's a strong attachment to your real world identity and status. And so people are saying things, I think not necessarily because they believe them, but because they want to be perceived as believing them…”

“Reddit has the upvote. Um, Reddit also has the downvote. And so that's where community can reject, uh, reject behaviors, um, or whatever they don't like. I think this is really powerful because if you're extreme or polarizing, chances are you'll get just as many downs as you do ups. And so it kind of cancels out. Um,…”

“because that control, that manicuring the message, that kind of pushing people into the desired outcome is what creates that sense of distrust. That sense of I am being manipulated. I am being controlled. I am being constrained.”

“And I think as a general rule of thumb, the more kind of, uh, emotional they are, The more suspect the message should be.”

“Being humble about your brand is not the way to go. You can be humble in your life, but don't be humble about in your brand. You have to brag because that's what consumers care about. That is what the press cares about.”

“one of the things I discovered coming into it is, is, is a single brand dies in this industry.”

“My intuition is that with the advent of large language models and ChatGPT being that inflection point with large language models, talking to software is perhaps the most ergonomic way we can interact with software because you don't need an instruction manual to have a conversation.”

“The amazing positive impacts of these generative models and their flaws are very intertwined. Um, what affords their ability to be creative and responsive and aligned with the person using them is also the basis for hallucination.”

“We're all competing for status in this world, and, um, no amount of productivity in the economy will change that aspect of society or human nature, and as a consequence, we'll create an economy around the technology that exists around us to enable us to, to be what we've always been, as flawed as, as humanity is.”

“the best possible thing to do to hold technology companies accountable is to encourage competition, or what, you know, I think Andreessen and others call little tech. I think that's actually, um, probably the most viable thing. I think it comes from the natural sort of creative destruction inherent in technology, and…”

“you should be focused in on increasing scope as much as you are going to, uh, think about scale. Uh, and, and I think the scope allows you to serve the same customer with more things. And scope allows you to serve lots of customers. And then driving both of those is what we call learning and learning effects. That the…”

“You know, my friend Ethan Mollick says you need 10 hours. I think you need about 40 hours.”

“She says there's a first mover advantage in adoption. And I, and I truly believe that. It's not a winner-take-all business. These things are first-member advantages, because, because this rate is so fast, so the more you wait, the further behind you are”

“there's plenty of products like that that exists. They all suck because the models are nowhere close to reliable enough where you can actually depend on it to do any of those activities. And even if it has, let's say even a model has like, um, 90% reliability, which in machine learning for these models would be like…”

“You can build systems that can do that and not have your data being taken away and used to train other systems, right? You could do all of these things locally. You could do these things with you. You can keep them with you. That's not something that technology cannot enable. But today the reason it's not happening is…”

“Adding provenance to data that gets generated by these models, right, so that you know whether this is, you know, real or fake and all of these things. All of that responsibility and, and, and regulation makes a lot of sense. It's not gonna Save you from the bad actors.”

“contrarian is contrary to something, and so most people who say I'm a contrarian, I view them as a different type of conformist because, because they're still reacting relative to how other people act, right?”

“The inflection is subtle at the time. A lot of times the founder doesn't even know what the inflection was when they started their startup.”

“time and again, the product that ends up winning is not the product that you see when you're doing a seed investment. Yeah, that was true of Twitter. It was true of, of Twitch. It was true of Lyft. It was broadly true of Okta, although not quite as true. It was true of Zoom. It would have been true of Marketa. It would…”

“These companies that are just, you know, people pejoratively say rappers on LLMs. But another way to think about that would be if you're one of those, you have to have a strategy that's distribution led. You have to have an advantage in distribution. Otherwise you don't have a chance.”

“So if I look at failing institutions in the Western world, almost all of them are characterized by the fact that they were granted a monopoly And there's no option for exit.”

“Most venture capitalists will tell you never to do because you'll just never succeed at building something or working in that, in that world or field, even independently, much less together. But then once you're in and once you're able to do it, it's, it's incredibly valuable and has just a massive, massive moat around…”

“Urban environments are very, very challenging because there's so many variables, so many things you can throw at it. Highways makes a ton of sense.”

“when you kind of know you're on to something, when people sort of have a really emotional, even if negative reaction to it at first, you know that you're, you're probably in good territory. The stuff when you come up with something and people you talk to say, oh yeah, that's genius. It probably means there's a lot of…”

“the core insight is that you could build a shape that represents English, a shape that represents German, and just rotate one shape on top of the other to do translation. And even though there are words in one that don't exist in the other, the point which is dog ends up in the same spot in both. And that's sort of…”

“if we as a US are gonna spend a trillion dollars in the next couple years on AI capabilities, shouldn't we at least be spending one percent of that on upgrading governance itself? Like, the US was founded on the idea that a group of people could come together, think really hard about how do you make a form of…”

“I tend to think that, ah, of, of your scale solution to any world problem, it can be criminal justice, it can be economic justice, but also climate change, 30 to 80% of the solution is a technological solution, so you have to ask yourself what the technological strategy is”

“what history has shown us Is that open source is the safest mechanism with which to deploy technology. Uh, having multiple people scrutinize, do due diligence, harden over time is actually the surest way to build the safest and most secure systems.”

“most of the most successful people are also the most naive.”

“And I think you can win by sustaining. Some businesses, maybe there's a winner tick all, but really almost, there's a lot of opportunities outside of that. That's like saying one restaurant is where everyone eats.”

“Everyone who says they're not a micromanager, micromanagers.”

“Government sector, and in particular, the nonprofit sector is filled with well-intentioned, hardworking people, but often are trapped in, uh, Infrastructure and ecosystem that has been built and most importantly, the bureaucracy that is surrounding them and they can't look beyond that. I think the difference in the…”

“If you cheat any of your constituencies, any of your stakeholders, or try to sell them short, you can get away with it in the short term. In the long run, feedback loops are created, and your business sub-optimizes. So, I just realized to, to, to, to create the most value for shareholders too, you have to optimize the…”

“So the short answer, Jeff, in a way, is I think you should stay out of politics if you're a CEO. Uh, you can obviously have your personal opinions, but you're always going to be seen as speaking for the company, and if you do controversial things, you're going to hurt the business. And I also think you should stick to…”

“Everything was sold on discount and price. And I thought that was wrong. I think, you know, that, that's, um, well, it, it's boring for a start if it's, if you're looking at his price rather than looking at specification and how things perform. And I, I think performance and durability, uh, enjoyment of use, ease of…”

“it's, it's always usually the technology that, Decides that we should go into a certain product area. It's not a business decision.”

“if you're a new manufacturer starting up small scale, you're paying 30 to 50% more for each component than an established manufacturer. So even, even your, your specification might not be better, it's going to cost you 30 or 50% more, and you can't survive doing that.”

“You need that mixture, but you need a lot more of the naivety and very little of the experience. If you have too many experienced people, the, the sort of general, um, mood is one of doing things in the ordinary expected way.”

“Like, for example, um, I don't have any worries that if I do a GBT prompt in something I'm writing, and it gives me a couple sentences I really like, and I put those sentences in. I don't feel like I need to quote them. I don't think I need to go, you know, and here, this is, this is from a GBT prompt and so forth, as…”

“If you are using a digital twin of your image or voice, you should be signaled in some way. It doesn't necessarily have to be like glaring red lights in the background. Right. But like clearly not hidden.”

“I think we vastly overestimate talent that's natural and vastly underestimate the power of our environments.”

“And I think in both dimensions, passion and perseverance, the thing that was most striking was not the intensity, but the stamina. And I stand by that, and other labs have found that in their scientific research, that when you look at high performance, it's not like, oh, this person stayed up for three nights in a row.…”

“They don't help us sell tickets. They don't help us sell merch. Like their audience is broad, right? But they help us tell the story. And if we do our job right, we can convert the people that pay attention to our story.”

“While there are really important red lines around national security and trade that should not happen with China, there's always this green lane of just normal trade that will happen between two huge economies.”

“I think the market takes care of things that get too big. The number of companies That are in the Fortune 500 today, that were there in the eighties, is much smaller than the average citizen believes it is.”

“The scale is concerning when it distorts it because it crushes competition. If, you know, kind of company, tech company X were to gonna get to scale and then lock out other players to the detriment of society, detriment of the industries, detriment of consumers, but that's not an absolute scale number. That's a…”

“when there is that kind of, as it were, the zeitgeist, a time of layoffs, you can then kind of go, okay, I now have a permission to, to do some of the resetting in the business.”

“And I think being a strong leader is also to know when to shut up. And not say anything, because you're not supposed to have an opinion on everything, and certainly you're not supposed to have an opinion on everything publicly.”

“For the ones who are saying, no, no, that's my baby, like, when you start talking in these terms, when you can see the, the emotional attachment, I always encourage them to have a very, very direct conversation with the potential buyers, understanding that promise, promises are cheap, and that most likely, especially…”

“NPS measure, to a large extent, happiness. Return. Measure success.”

“And I believe that the only way you can build new fans is to first please the core fans. It's, it's everything.”

“So first of all, you will need an egomaniac leader because this egomaniac leader has to withstand a lot of pressure from the existing infrastructure of the company.”

“A second thing you need is you need a separate physical building. I don't think you can do intrapreneurship inside physically a company that is already existing and, you know, going forward and maybe even successful because you're going to be matrix to death.”

“Guy's golden touch is whatever is gold, guy touches. So I touch Macintosh, and I touch Canva, I would touch Liquid Death. It's because it's easy to evangelize great stuff, and it's hard to evangelize crap.”

“At the same time, the notion that we should collapse All of the entities in the nonprofit space and just have one and no duplication. You'd eliminate competition. You'd eliminate innovation. You'd actually create a less good customer experience and less advances. You want a little bit of competition because I will tell…”

“Because ultimately, the defender has the home turf advantage. They are the people that know the business and its culture and its digital identity better than anyone else. And by leveraging AI, they're able to arm those defenders with that knowledge and stay one foot ahead of the attacker.”

“a lot of this is based on the idea that The attack will be known, and it will be in some way predictable or repeatable, and the reality is the vast majority of these attacks are novel and unpredictable, and so you can never eradicate all risk by building in that Secure by Design.”

“People say chess is the king of games. Well, chess has a bunch of problems with it relative to parallels to the real world. The bad thing is it's epistemologically shared, which is we both see the same board. It has no randomness, and actually, in fact, you might say, well, the world's not random. It's like, well, the…”

“There is no competitive game that doesn't involve some deception. The same thing is broadly true in business too, because like which product am I going to launch? Which partnership am I going to use to do that? What do I think is the right way to compete with my product and your product in the next generation of…”

“my, my fundamental premise behind all game design is that games should not be entertaining. Games should make the people you're playing with entertaining.”

“The dumbest idea in Hollywood, known by all, got made and turned out to be a critical darling, and I got nominated for an Oscar, and I thought, wow, that means nobody knows anything. Whether it's movie story or a tech story or a consumer story.”

“And frequently what I say that in the venture industry is your ideal investment is something that seems crazy right now and totally obvious two to three years from now.”

“We also believe that the best talent around the world doesn't all exist within a 90 minute commute of an office, and we have people all over the world working for us, so we got a talent advantage there.”

“We believe that you do need to get together to build social bonds. Our belief though, is that you don't need to get together every single day to sit next to each other on a zoom call in an office and commute back and forth to get that benefit. We believe that you can get together for what we call intentional…”

“Some people who are forcing a back to office mandate, in many cases that's like telling people they need to use a blue pen instead of a black pen. Does it matter which pen you use if the output's the same? Does it matter where you are doing the work if the output's the same?”

“presence in an office is not any proxy for productivity.”

“Some companies operate a two-tier system where they say you can work remotely, but that is a second-class career path, and we're reluctantly doing that. That's remote or distributed in name only, and you're not going to get the best people.”

“Most of the challenges we have come from the lack of money and the lack of information or what to do with money.”

“I feel like those kind of constraints can be incredibly exciting, and they can also be awful. And I've been in both situations, and I keep promising myself I'll never do that again. It doesn't usually end happily, that story.”

“In today's age, if you are in any kind of leadership position, your customers, your audience, those that you are trying to sell to, want to know who you are. Gone are the days of us being behind facades. Or behind a door in the corner office.”

“And I believe you must strategically ease control of your product and let people who show genuine enthusiasm become your co-creator.”

“What I've learned is pad your deadlines, um, lie to them, and outlining the cost of what it's going to be if we don't execute by this date.”

“Traditionally, the way that game testing works is you hire a group. They do these blind tests. Everyone sits in a room. There's the one-way mirror. You watch people play the games. It's horrible. And I looked at that trying to figure out like, why are these tests so bad? Why are we pouring all this money into it and…”

“Many times being open is much better than being closed, because what gives you your competitive advantage is not your hidden secret thing. It's the fact that you're in motion with a great team.”

“A lot of founders, especially the tech entrepreneurs, tend to think of the tool they want to build, as opposed to the community. The primary paradigm tends to be, here's a tool. It's a hammer. It's a screwdriver. I give it to users to do a specific thing. And the secondary thing tends to be, here is the interface. How…”

“If you're not grappling with it, you're living with a false sense of neutrality. You're actually allowing your most extreme users to make the decision for you, because in these cases, a non-decision is also a decision.”

“Going down rabbit holes became data points and context to other moments of going down rabbit holes that allowed me to either bail early, pattern recognition, or triple down on an opportunity, and so, you know, I'm a, I really, I really don't know how a CEO or entrepreneur, um, sees the world in any other way. I feel…”

“I think that I know, because I live in it every day, you can waste an ungodly amount of money on influencers, on Facebook, on Instagram, on TikTok, on Spotify, Um, just as easily as you can in a newspaper or billboard or radio.”

“every time big business has gotten in trouble, the Fed has stepped in by lowering interest rates, and big business then can access, even failing big businesses, can access the capital markets on incredibly good terms. That's a luxury that isn't available to smaller business, and yet we don't really think about that…”

“If you had argued we should take the plan for influenza and applied it to COVID, you would have been wrong. Influenza is spread in schools. Schools are super spreaders, and kids did die during the 1918 flu. It's different. So you can't say that because we prepared for that pandemic, we should take those lessons and use…”

“if who makes money is being dictated by government policy, But then you're saying that hospital closure should be dictated by a hospital's failure to make money. Well, wait, that's not the market. That's government incentives.”

“Having an advertiser be the financial party responsible for paying for these services means that ultimately these AI services are beholden to that advertiser and not to the end user.”

“By spending too much time debating the existential risk of AI, we actually increase the likelihood that AI will help bring about a dystopian future. The long-term conversation is doing a disservice to the immediate issues that we face.”

“We have to really reshape behavior because women are taught not to make the first move. Women are taught not to speak first. They're taught never to send that first message, never to initiate. And men are taught to be very aggressive and really beat down that wall until she says yes.”

“You have different types of organizations. Some are advocacy organizations whose job is to be vocal and to bring a very strong point of view. I'm working for an operational organization, one that is driven by an imperative to deliver. So we have to discipline ourselves to preserve this ability to deliver.”

“Everyone needs to speak up, especially business leaders. Your team is looking at you. You have Jewish team members. You have Palestinian team members probably too. You have to speak up. You have to show humanity. You have to show empathy. If you ignore it, you might not understand the level of damage you're creating.”

“And if you don't know yet, in my world, I think it's okay to wait another month, another quarter, not saying 10 years, but just a little bit, and then revisit on a regular basis whether or not there's new application of AI, new development that would make sense into your business.”

“personal productivity is not the only measure of business success, right? How many emails you answer in a day or how many Zoom calls you do is not really what business is about. Business is about how you solve client problems and how you help Clients succeed, and I think you can do that better more often if you're…”

“if you staff your offices to be busy three days a week, and it seems everyone wants to come in Tuesday, Wednesday, Thursday, actually is massively inefficient. You know, we have these buildings empty four days a week”

“It's really good at coming up with ideas, but it doesn't really know what's a good idea and what's a bad idea, right?”

“No one wants to let these computers totally go off on their own. And so, The computers tend to cut problems down into finer and finer things that need more and more people to manage.”

“when you go into a new, and especially a turnaround, you have to have a, such a clear, bold vision. Yeah, and you can't have, I, I called it cancer. You cannot have cancer eating away at different parts of the organization. You need everybody. You need that body just, you know, every part of it functioning if you want…”

“This notion of empathy is at the core of learning. We are in the business of meeting unmet, unarticulated needs of customers, right? That's where is the source of all innovation, all design thinking.”

“So I've looked at M&A as, at the meta level, it needs to do two things. One is it needs to be something that we can clearly quote, unquote, say it fits our mission. It fits our identity. Oh, we can be a better owner, which is sort of a very narrow way to talk about it. But can we say, oh, as part of Microsoft, will a…”

“This alternate perspective doesn't hurt the second type of founder. In fact, it can be an asset if they can harness their risk aversion instead of being ruled by it.”

“In fact, I'd say when you're assessing your risks, you actually want to take on the ones that are most central to killing you as early as possible. If you're worrying about peripheral risks without addressing the essential ones, it's like worrying about what meal to cook before you even know what ingredients you have.”

“What you realize is small businesses lend more than they ever borrow, because that invoice that they sent that says net 30, that's essentially a free loan.”

“So, adding complexity is okay as long as you don't add orthogonal use cases that feel totally unrelated.”

“The dumbest idea in Hollywood known by all got made and turned out to be a critical darling, and I got nominated for an Oscar, and I thought, wow, that means nobody knows anything. Whether it's movie story, or a tech story, or a consumer story.”

“frequently what I say that in the venture industry is, your ideal investment is something that seems crazy right now, and totally obvious two to three years from now.”

“It turns out that even in spite of the growth that we had in success that we had, there's still this validation that sort of comes with institutional capital. There are still a lot of very smart people, which the primary way in which they judge the quality of the business or the prospects of the business is whether…”

“anytime that large tech companies talk to each other, you know, it's like, ah, antitrust, and you're like, well, actually, in fact, you want them talking to each other about safety considerations with computation generally, whether it's cybersecurity or whether it's, you know, artificial intelligence, and you need to…”

“Because, you know, if you crowdsource, if you get the average of 20,000 people what their opinions are, you kind of get to the average opinion. You're not getting, you know, the really juicy stuff what makes you different.”

“The answer is simple. Hire the smartest people you possibly can and put up with them. Right. Um, and we all understand what that means. Right. But you really need them for competitive advantage.”

“And I think on the cultural side, that can turn if the smartest person in the organization isn't aligned with you culturally, that can actually be pretty dangerous. And so, As an organization grows, you make allowances, certainly for your most talented people, but if from a cultural standpoint, they're not aligned with…”

“If you have a toxic culture, you could be working four hours a day and be miserable because you feel you're not treated with respect. You feel you can't speak up, you can't express yourself, and that's when we burn out. It's not because we are working hard and we are happy, we are contributing, we are building…”

“I actually think that the data insights team that we have, it almost in a way has benefited from not talking to customers all day because they are actually looking at just the data and then looping that together with folks who are talking to customers all day and reaching out to customers and really creating that, that…”

“And if you're part of an underrepresented community, I think people give feedback to you even less.”

“And in your company's early days, I'd argue it's more important to get users in the door, even when you're taking a very steep loss. But when you ultimately need to change the price, They'll grumble for sure. A few might storm out, but if you brought enough of them in, and you've created something really compelling,…”

“that still is part of the core of what made ClassPass everything it is, is that people loved variety, and no one realized that. There was this market out there for dabblers when everyone was trying to push everyone to be, like, complete loyalists”

“You cannot answer these questions by running limited time only experiments with your pricing. You have to go all in to really understand how users will respond.”

“You have to know what is it about your service that your customers find invaluable. Protect that, and that's the only promise that really matters. Pricing riots die down, and if you have a service that customers really love, they are eventually going to let you out of the doghouse.”

“In my experience, two co-founders are almost always better than one, and three co-founders are frequently better than two.”

“The problem is that you have this app that's a network, but no one's on the network, and it only becomes useful once people are on the network. So you have to have what we called single player mode feel awesome. And it turns out single player mode as a app where you could take a photo, filter it, and share it to many…”

“I think this is one where measured and consistent approach is going to be better off. The reality is that with the number of resources out there, there'll be the opportunity to be fast followers.”

“They have, most of them have engineering societies. It's very, very important, but it can't ultimately drive creative. It can't, and it shouldn't.”

“High-achieving people have a tendency to be perfectionists, and the same instincts that make us good students can make us lousy entrepreneurs.”

“what it really served as Was a check and balance on the power of the engineering management over the subject. So if an employee is under pressure, the manager says, you've got to work harder. You've got to give me everything you have. That employee can legitimately look that boss in the eye and say, I'll give you 100%…”

“And the further you move away from Silicon Valley, the harder it is to find someone who will take a crazy idea seriously.”

“I believe there's only one way to find your big idea. Look for it. Look for it. Look for it. And then act.”

“I tend to think that the best ideas are produced by networks, not individuals, and that feedback is a huge part of scaling an idea successfully.”

“I believe you can pivot from failure to success, but only if you slash and burn the rest of your business.”

“I believe that, as CEO, you always have to bring the core team along during a pivot. You have to make them feel like it was a joint decision. It doesn't have to be completely democratic. In fact, it shouldn't be democratic. But it has to feel democratic.”

“I tell people to this day, I think the best first job, I don't care what you want to do in life, it's a sales job. Best job. Because you learn how to ask for what you need. You ask for the order, and you learn how to be resilient, and that a no is not the end of the world. You learn how to negotiate. You learn how to…”

“I tell people all the time, women, minorities, go do an international assignment. You will actually have a edge above people who have not been minorities and experienced being minorities in a new culture.”

“And the reason I picked that strategy is I said, alright, if it doesn't work, nobody thought it was going to work anyway. But, at least I've had a top tier VC behind me, they've had a chance to see what I can do and who I am, and therefore hopefully get another opportunity. So that was my worst case. Can you live with…”

“Most often, the shift from the executive job to the CEO job is, you now own the job. Right. Doesn't matter what your board member says. Board member is right, wrong, indifferent, doesn't matter. You own the job. Right.”

“Charities use shame and guilt to market their wares. They, they made people feel terrible about what they had, hoping that they would respond. You remember those Sally Struthers commercials from the eighties, and the kids, and slow motion looking sadly at the camera, and the fly lands on the forehead, and the 800…”

“The worst thing is you launch a product and no one cares or notices. And if you had sales reps complain or customers file bugs against it, then two things. One, you're releasing while you're so embarrassed, a la your role, and B, people only complain when they care, right? And so I always, uh, say as a metric, you…”

“We give you a free product, and the better that free product is, the more you use it, the more you're going to convert.”

“They're saying, like, what if we frustrate the free users as much as possible? Surely we're going to push them over. What happens is they push them out.”

“Daniel is a disruptor, but most disruptors don't actually work with the industries they're disrupting. Most of these disruptors just reinvent, push things aside, and create their own closed loop. Uber Doesn't work with taxi companies. Airbnb doesn't work with hotels. They just kind of go, we're doing our own thing, and…”

“I believe that to survive your entrepreneurial journey, you have to learn how to recharge yourself. Call it balance. Call it wellness. Call it yin yang. Your business and your life depends on it.”

“Right now we still talk about work-life balance, which I, I think is just not the right way to address this problem, because it's not like work and life are at opposing ends, that in fact they rise or fall in tandem.”

“A founder cannot succeed unless they're obsessed with their company. And so part of being obsessed with a company means that it's what they think about on Saturday morning. It's what they think about when they end up with, you know, a 15 minutes spare, you know, kind of waiting for the DMV or for their friend to show…”

“Your subjective assessment of how well you're doing with insufficient sleep is a miserable predictor of objectively how well you're doing”

“I think the problem of our whole system and our educational system is that it teaches you to be right, and you have a possessiveness to be right, and oh, now it's embarrassing when you're wrong, it's embarrassing when you have a weakness.”

“And if you're only doing A-B tests, like you're never designing with empathy.”

“If I say, what can I do to make this better, they'll say something small. If I were to say, Reed, what would it take for me to design something that you would literally tell every single person you've ever encountered? So you start to ask these questions, and it really helps you think through this problem.”

“The point of the process is that maybe nine, 10, 11 are not feasible, but if you go through the crazy exercise of keep going, there's some sweet spot between they showed up and they opened the door and I went to space. That's a sweet spot. And you have to almost design the extreme to come backwards.”

“You cannot change people's behaviors if you don't change the boundaries that drive people's behavior. Lots of CEOs are good people. They don't want more unemployment or more people going to bed hungry or more climate change. But yet they're behaving as if, and it's because of the boundaries around them, the…”

“Executive coaching is valuable, but there's too much emphasis on coaching the leader as an individual rather than as part of a team.”

“I've always said that people follow confidence, but they're loyal to vulnerability, and so if you're vulnerable with your team about the things you're terrible at, Someone will lean in and take that over for you.”

“But if you're good at recruiting, it's really all that matters.”

“I don't believe in theoretical questions because if you ask a theoretical question, you get bullshit answers.”

“I believe reference checks can actually tell you more about a candidate than a one-on-one interview.”

“As a strategic entrepreneur, you're not trying to get in at the peak of a trend. You're trying to be one to three years early so you can have time to build toward it. So when the moment arrives, you already have momentum while everyone else scrambles to get up to speed.”

“sometimes you don't choose the time, the time chooses you. That doesn't mean you have to seize that moment, but it does mean you have to be comfortable with the possibility that the moment won't come again.”

“When you're scaling, if you don't have the horizontal culture, your culture will not scale, and then that will become a competitive disadvantage because it's very hard and takes a lot of energy to refactor culture, and that's part of the reason why everyone tends to be get culture right from the beginning, and scaling…”

“One of the advantages of being dyslexic is I became a great delegator, and when I talk to various people who are starting up in business, the most important thing I can tell them Is delegate. Find somebody better than yourself to do the day-to-day running. Make sure that you can find time to think about the bigger…”

“There's a mystique surrounding the process of winning investment, the financials, the term sheets, the equity you're prepared to give up. And of course, there's the dreaded pitch, something many first-time founders obsess over. But all these things should be low down your list of concerns, even if you have your first…”

“I don't think people realize that sometimes the best time to start a business is when you're broke. Right? You got nothing to lose, and if you're looking to be an entrepreneur, you don't want to take on a lot of debt and, you know, the car and the house or the, the expense of this or that, that living like a student…”

“That being said, the investment criteria that I apply is, would I give this person the money and walk away and say, Five years from now, how did it go? Because it's about the entrepreneur's journey, not yours, not I, as an entrepreneur, can make this successful. It's, can this person make this successful? And I'll try…”

“If you're not willing to do even that, you're not an entrepreneur because there's always a measure of sacrifice involved no matter where you are.”

“Most big social programs in America, like Social Security, Medicare and Medicaid, as is true in other countries, typically start off smaller than they probably should in terms of overall need. That's why I call this starter house, and then you build from it, but you've established the principle of that everybody should…”

“I believe that the first 150 hires will make or break your business. They are your cultural co-founders, and it's up to you, the founder, to get everyone right.”

“I tend to think, if you want an adaptive and creative culture as the top priority, you have to hire adaptive and creative people, and adaptive creative people aren't necessarily going to stay in one job for 10 years.”

“Nothing drives innovation more than continually to expand your product portfolio. Not, not getting crazy about it, but that's growth. That becomes also a way to become more strategic to your customers.”

“In enterprise, products that are 10 or 15% better might have a short run of success, but usually the large incumbents can catch them.”

“So different than consumer enterprise founders typically come from an enterprise background. They don't come out of left field. You know, they don't come right out of college.”

“The creation of good and fulfilling middle-class jobs is one of the most important goals we can collectively focus on. Because when people feel more safe and secure in their economics, they feel there's a good future in front of them. And they tend to be more open-hearted. They tend to be more permissive. They tend to…”

“Sometimes you, you can get a focus group of one that's more powerful than the rest of your data, and that one was probably it.”

“What really matters to your customer is that they have an amazing experience. They don't give a how it got there. You're at, uh, your favorite hamburger joint. You want a great fresh burger. And if you find out that the owner of the company was there back there making it, you're stoked. You don't care if he figured out…”

“You have to start swapping out what I call generalists, those jacks of all trades, with specialists. Experienced executives who know how to lead massive teams.”

“I think one of them is a bad hire in the first 15 is fatal to the company, so really watch out for those bad eggs.”

“And when I look at my friends who are running other good companies, the single biggest difference that I see in whether the companies end up becoming really great and reaching their potential or just pretty good is whether they're comfortable and really self-confident enough. To have people who are stronger than them…”

“Mark and I didn't agree on a lot of substantive things at that point, and Dave told me, he's like, don't work any of those out, you never will. He said, what you want from Mark is process agreement on How you will work things out. Because even if you work all the questions you have out now, they're going to change.”

“the further something is away from your business, the harder it is for you to get to it over a period of time and build it. Cause usually what you wanna do is do, do hops and hops, but if you take a big leap, sometimes you leap too far and it's really hard to, to get to this hole.”

“And you can't believe how many people I've had in my office that try to convince me impulsiveness is a virtue. And, and they're confusing impulsiveness with boldness or decisiveness. Impulsiveness is actually without thought.”

“The outside game matters, too, because all of that effort pays off more and is more rational in some ecosystems, in some environments, in some cultures, in some places, with some people, and less so in others, and I, I think if you're gonna achieve your potential, you need to master both the inside game and the outside…”

“I think, I think physically working in your bedroom all day is awful for most people. In, in part because there is no transition. You know, there, there is no queue. That, you know, now work is over. Oh, wait, now work has started. It's just one blur.”

“You know, he discovered very early on, as a coach and as a mentor, that you can tell people what to do, but it doesn't work very well. Um, and you can try to keep the people who report to you, in this case, his players, accountable by, by the force of your authority, because you are higher level than they are. But…”

“The default settings of the modern world, the situation, if you don't change it proactively, is not a healthy situation. If you are not proactive about putting yourself, you know, in places and with people that are good for you, the default settings are, are not necessarily going to, um, be for your best.”

“you're, you're changing a culture at the end of the day and changing cultures is, is, is like stretching on a rubber band. You know, the minute you relax, it just pops back.”

“what I am good at is let's not look in the rear view mirror and let's quickly recognize anything that we're doing wrong quickly, quickly, and there to be no consequence to that and no reflection upon it. So I'm not one for saying, Why did we make that idiotic decision and who, who made it and why did we make it? Mine…”

“The, the, the, the key of the business is the consumer. You, you have to deal with a lot of different groups, advertisers, in our case, cable operators, artists, record companies, this and that. But if you could, if you could make a connection with the consumer, And know what's going on inside that consumer's head and…”

“If someone hires somebody who's substandard, And they don't work out. That person is likely to hire other people who are along the same lines. So you're gradually eroding your company's vibe from the inside.”

“the digital revolution began to hit and break up this ecosystem, which we survived on the fact that we had this central operation where we were like editors. We could manage because of scarcity. We didn't have to put out a lot of things.”

“One of the things that, uh, came out of that was that we found that their lives tended to work best, uh, phases of their life when they were doing something for which they were really, uh, deeply encoded, as opposed to just good at.”

“there are really three elements of being in frame, right? One is being in frame with something you really encoded for. Second is that it is something you're willing to flip the arrow of money for... and then that third part, what really feeds my inner fire.”

“it's if you ask each person in the relationship who benefits more from the relationship, they would each say, well, the other person is so marvelous in my life. I do, but they both feel that way.”

“much of what is really spectacular that people do can happen well after 50, 60, 70, even 80 or 90, even the really, really creative stuff.”

“I used to believe that giving mainly meant like philanthropy, giving, volunteering, and it does, but I think the highest form of giving is to give of your encodings.”

“in this AI era, we are just hurtling towards, um, living our lives at the speed of play. And I think that that's more and more accessible to all of us, that this idea that we don't, you don't have to quit your job to, to try out, build an idea that you've been thinking about. You don't have to go and Mortgage your…”

“new is your novel idea that will probably be the reason why people will try this product, and it will probably also fail.”

“And I think we're in this weird paradox with AI that I would have thought by now that people would be all over the place with these testing machines and they'd be Building prototypes in a day and testing and they're not, and it's not what I see because you can almost get to that minimum viable product in three months…”

“I think that what's going to be the big unlock for games is the more that we put the real world, you know, real humans, real social in our games, because basically games should be a good use of your time there. It's this big of industry and it's total waste of time. Imagine if games improved your life skills, imagine…”

“with AI being, uh, having a huge disruptive effect in, in search, we're really trying to make sure that we are Playing and meeting audiences where they're at, publishing a lot of authoritative, educational, and entertaining content, whether it's, uh, distributed through social media and, or, and, or through our own…”

“if you think about care on the consumer side, where it was for 18 years, really, it was a mostly, it's a transaction experience failed in subscription. And why do you need a subscription after you find, find your match?”

“And so I w I can assure you most of those caregivers would love to take some of those duties on because again, it, it prevents them from having to figure out the scheduling and the calendar Tetris of going to other locations and they can actually earn those wages in the home. So it's, it's actually a way for families…”

“I think that you should try to use AI in a case where you're not going to have to go undo six months of work or undo having spent hundreds of millions.”

“And so I think for any, any time an engineer is forming a business, there's, there's a tendency to be really close to the product, which I think is fantastic. It's, it's really a wonderful characteristic of, of technical founders, but you also need to recognize you can't be in every decision or in every meeting. And as…”

“Rivian was highly undercapitalized in the early years. And the reason I say it's fortunate is allowed me to learn how to run a company. So my first time starting a business, my first time running a business, one of the things that was helpful for me is we, we were able to grow slowly, but I was making mistakes. I was…”

“And I think it's important for them to feel the brand because when they do, they go above and beyond. And when we go forward and I'll talk about other brands, it makes a massive difference, especially on entrepreneurial brands.”

“First, make sure you have a good relationship with the agent, because You can't go around the agent. The agent's their go-to person. So there's no going direct to artists. So foster that direct relationship with the agent.”

“And then a core part of the final negotiation is I'd like to say with the artist. Because in the end, they're representing our brand. So all the upfront negotiation, you're never going to get there, but you have to, you know, it's almost a house. You got the final inspection before you write the check. You got to do a…”

“Corporate America, a lot of chess moves, um, they get nervous when you move very fast, and when you make stuff creative, and where you're not playing politics, well, not for to be fair, I was playing politics terribly. You, you feel more like a threat than, um, uh, a liability than an asset.”

“And now every influencer wants an equity plan the same way that artists and celebs wanted it back in the day.”

“There's actually science behind this. It's called the creative cliff illusion. We think that our best idea comes first or not at all, but actually that's not the case. It's usually the convenient idea that comes first.”

“Like it or not, and whatever their political beliefs are, if that trust between strangers degrades, I don't care what your policies are, you're jeopardizing shared prosperity.”

“I, I think it would be really hard to do it as a solo entrepreneur, right? The highs are so much higher, but the lows you actually have like support. And so like, I think that if you don't have a co-founder, find someone, your first hire is probably going to be basically your co-founder as well, but. I think, like, the…”

“Because a lot in beverage, if you think about it, are really in a lot of better for you products. They grow really big in New York and LA. And those are your hubs, and those are your big markets, and you really focus on it.”

“I think it's, it's still arguably my best tactic for developing new ideas is to be in a foreign market, ideally with a creative or a couple of creatives with you. So you can sketch as you go, cup of coffee in hand, incredibly jet lagged. Nobody can bother you because you're on a 12 hour time difference. And just when I…”

“I never steal from our competition because then you're just a hack. That's embarrassing. I try to steal from as far away from what we're working on as possible.”

“the barriers to entry was so low that if we didn't bring in industrial design graphically, it'd be much easier to knock us off, which did start happening.”

“it's somewhat counterintuitive, but you actually want to seek out the hardest, smartest customers and have them beat the crap Eddie. Because Others will follow their peers in the industry, know how good they are and learn from them. So take on the hard first and work with them as design partners, go through it.”

“Hippocratic Oath of Venture, do no harm, like stay the hell out of the way when things are working. And send them customers, send them candidates, but like get out of the road if, um, if they're executing well and going, um, don't try to give product input, you know, out of cycle or sitting in a board meeting, like,…”

“I don't think we can ever truly overcome it, as your example shows. Having anxiety tells us that what we're doing is important, gives us energy, helps us focus, but we have to manage it so it doesn't manage us.”

“I think the single best expectation setting tool for communication that we seldom use is the calendar invite.”

“Meetings are often band-aids for bigger problems.”

“leverage AI. LLMs can be really helpful, not to help you create answers. That's not what I'm looking for, but to help you get questions to practice.”

“People think I can, you know, if I can do a 30 minute presentation, I can do it in five. Not at all. It's very different. And so you have to get that experience and you have to practice it.”

“It turns out that the neuroscience and behavioral science that are my, my stock and trade follow these four idols. Everybody has one of these idols, as a matter of fact, that distracts them from the thing that's greater to themselves and will, will betray them, beguile them, distract them from, from actually pursuing…”

“when you elevate structures of capitalism to a religion per se, when it's not anchored in morality and love for other people and a responsibility to perhaps even the divine, what you're going to do is you're going to cut corners and you're not going to get the competition that's supposed to be the central operating…”