startup

“The data you get back generally does not change, but it's precision will. So mathematically speaking, you're going to get the same level of trends, but the precision at which you understand those trends will become more deep if you have more data. But the unde…”

“However, I think it's super important that founders see a line of sight to work on this for, I think my rule of thumb is a decade. Just do you see yourself working on this for a decade? And maybe it's not a decade that you actually work on it. It probably won'…”

“These days for early stage startups, we're almost always running the launch announcement as an exclusive, which means you give the news to a single outlet and they're the only ones who get to write about it.”

“You want to hire pie shaped marketers and not pie, like a dessert, but pie, like 3.14, where the pie symbol has two vertical lines. So like a T, but it has an extra line. And it's because you want the first marketer to be an expert in one of those three areas …”

“A lot of the best startups are just like someone's vision. It's like, here, this is what we're gonna do. And then the more it becomes a community driven thing, the less often it ends up being successful.”

“A lot of startups at this point are almost allergic to C titles or VP titles or are just more title agnostic than I've seen in the past. So you see a lot more of these head of's and that is sector leaders up until probably C plus or D stage. And then you get t…”

“Companies either grow or they die. There's no middle, right? There's no like, oh, we're gonna cut burn and just try to like survive the winter long enough so that like, that doesn't work, right? Because employees get, get demoralized. Investors lose faith. The…”

“There's more resilience built into the system than you might think.”

“And so the founder is like, Hey man, I'm going to like pour a little bit of sales on this, hire some, you know, sales leader or whatever, some sort of seller and outsource this. And you really just can't do that. Not for the first, like couple dozen customers.…”

“One is waiting too long to monetize. Another one is underpricing, and this isn't just setting the base price too low, but it's also leaving money on the table by not offering different plans to cater to different segments. And the third one is all too often wi…”

“At a startup, you can't do that. You just don't have those users to test with. And I think a lot of startups make the mistake of trying to use an experimental approach too early, where it just takes either way too long to get statistically significant results,…”

“Bigger companies can always get more done. They can always spend more. They can always move with a higher degree of velocity than smaller companies. The advantage a smaller company has really is in latency. You can have an idea one day. You can test it the nex…”

“Most of the time, PR is not going to get you leads or users. It's just not.”

“My guess is most startups are going to have nowhere near enough data to build their own model and make it something really interesting.”

“Progress on this like weekly or biweekly timescale is a really good indicator of someone who'll succeed. To me, much better indicator than I am in this market, or I'm talking to this investor or something like that.”

“When you are a small startup, strategy does not matter because there's not that much of strategy is about. Maybe later on, it might be a fault to think about strategy, but strategy kind of assumes that you can do multiple things at the same time, which small s…”

“I think the truth is that we're not, not, not very good at knowing what's going to succeed. We're not, certainly we cannot figure out who's going to be the really successful company in the batch. Like that's not possible. What we're good at is knowing what fai…”

“You can't start a startup with a growth team mindset, because that is just scalable things all the time. And really what you need to go back to is doing things that don't scale and unscale your way of thinking about customers. But it's really useful to have th…”

“Like they think they might have to talk to five, but I think you have to talk to like, 25 to 50. That means you have to reach out to a lot more to be able to get to people that are potentially early adopters. And those ones you talk to are also the ones that b…”

“The worst thing that can happen to startup is not that people hate what you're doing. It's that they're completely indifferent to what you're doing. So not that, not the worst thing, but the most common thing that happens is people just indifferent, but it doe…”

“Don't make somebody the CMO, or even the head of marketing, if your marketing team is two people, right? Like, yeah, you might make the right choice, but two years later, your marketing team's probably gonna be more than two people, say it's, like, and are you…”

“You're fighting the status quo. And if that's the case, then you can't rely on maybe the government, maybe mainstream media to support what you're doing. And so you should assume that you want to go with an approach that doesn't require a lot of money or peopl…”

“And you know, that's gonna go away over the next five years. And it sort of takes us back to what product management used to be like, which was, you know, you didn't have all these resources around. You didn't have all this time to figure it out because if you…”

“I think getting into startups as a product manager is a pretty awesome way to get into product because it's just a lot of problem solving. The problem with that is you don't have anyone to teach you the right way, but the product will teach you the right and w…”

“So think about it in terms of structure your vesting. Commensurate with the value you want, which is very much front-loaded. I'm also a big fan of three-month cliffs. Something I, I've done, I always do actually, is listen, in the first three months, you'll kn…”

“If you're in a Hail Mary situation where you're looking for a home or you need an exit for your business, it's better to be transparent and cast a wider net.”

“As you add more operational people, it just creates more systems, and so, like, unless you're a massive company where you need that type of scale, I think, like, most startups, like, should avoid that decentralized model.”

“Usually around, I would call it, like, a hundred to a 150 people is the critical mass where you can't just have a village approach to systems and tools.”

“I think sometimes startups do, Try to like emulate successful large companies too much. And you kind of like do this, like fancy announcements where it's like, Hey, now we're like doing this fancy thing. And then it's like, sounds very like corporate or someth…”

“If you're a startup, you need to invest a lot more in differentiation. And then over the years, I think you start to balance the books a bit.”

“One of my main takeaways of that entire process is that it's always too early until it's too late.”

“In the research I've done, why now ends up not being that important for startups being successful or not, so I think there's a two sides of that coin.”

“And so the most common two paths that I've seen are people who switch laterally within a company, again, challenging, but can be done, or people who join startups.”

“In a competitive environment, being right is good, but being quick is necessary because if there are 10 startups working on an idea, some of them will gamble and they'll make bad gambles and they'll go out of business. But some of them will gamble and make an …”

“The only reason you need venture capital is if the, well, two things. Either, A, the technology is too expensive and you cannot self-fund it. GPUs, a bunch of that, training large language modules, those kind of things. Or This thing is going to get catch fire…”

“Here's what you need. You need a major account who's gone all in with you on the new technology and who is willing in some way to talk about it.”

“What we find is that the more there's a, there's kind of a big behavioral risk, the better this stuff works. So, so if you're just trying to make like a slightly better version of something that already exists, and maybe it's going to be a little cheaper or a …”

“So for 95 out of a hundred of us, our first head of sales should be a stretch VP of sales. And what that means is usually they were a director before that or a senior director or sort of a VP. Okay. But you should be cautious about hiring your first VP of sale…”

“The public companies are actually less, they have the higher CACs than startups, believe it or not because they have so much market penetration.”

“One mistake that you do see sometimes startups make is they get an early cohort of users Whose needs actually take them kind of orthogonal to a larger market. And so they become kind of held hostage by their earliest customers.”

“A lot of startups are dominated by the founder and the early people. And it almost doesn't matter what techniques they use. If they're good, it's amazing what they do.”

“Every company wants to do these percentage, like, growth stats when they just launched, and I've never seen reporters include that in their stories, and so there are ways to give signals of how fast you're growing without being that, kind of, like, disingenuou…”

“At a certain stage in your growth, like public companies, they do press releases for earnings. Makes a hundred percent sense. There are certain rules around when companies do need to issue press releases, so there's still a use case for them. I just think your…”

“I just think back to like when mobile happened, if you're a PM that jumped on mobile, you had the pick of the litter when it came to jobs in very interesting startups. And so I think we're in the same moment here where if you can ratchet down and specialize an…”

“In most, at least in the stage I operate in and startups and growth stage companies and, you know, late stage startups, organizations are very fluid. And I like to organize around talented, motivated individuals. And so just because we're organized in a partic…”

“Product market fit is the single most important thing that your startup does in the first three years.”

“I do think if you've been going at it for four to five years and you haven't started to find anything that you're really feeling pull from the market on, I don't know. You've done it for four to five years. It's like, what are the chances that you're going to …”

“The majority of companies, so greater than 50%, probably closer to 60 or 70% are gonna get stuck at L one or L two. And so that leaves, you know, roughly, let's say, 30%, make it to L three or L four, just in our experience looking broadly.”

“The way to extrapolate that is know what your comps are of what companies you, your archetype is, and then look at what they did on the zero to one and ignore what they do today. Right? Don't pay attention to what Facebook does today if you're a brand new star…”

“It's that you only get so many shots as an investor. And so anything that doesn't seem like this is the one I want to do is a no. And that that's actually why they're saying no versus this, you did, you know, oh, you had a bad zoom setup or something, you know…”

“It's pretty rare. I would argue that the cause of death is that they had lots of firepower and they were feeling really positive and they just ran out of money. That's actually like more rare than founders think. It's much more common that they still have some…”

“Usually a successful pivot gets warmer instead of colder from what you're an expert at and somehow builds on what you learned on the prior idea.”

“I think growth and growth hacking and doing all this analytics, AB testing stuff is a total waste of time for very early startups.”

“There are some that only are really available in the, when you reach a stability phase of a business pretty far out there. And so if you're starting a company, take those off the table. So those two are branding and process power.”

“Almost every startup that you want to deal with starts with, ah, counter positioning, because remember what mark product market fit is primarily is a substitution. It's you are coming up with a way to satisfy a more or less existing need in a novel way that cr…”

“Concentration is what builds wealth. Diversification is what preserves wealth. And you're a startup. You're not trying to preserve anything. You're trying to build something. It requires concentrated bets, not hedging.”

“If you're a startup founder, you've got to be okay with, I'm just going to go for this. And I know I probably won't get it, but it's so meaningful to me. I'm going to go for it anyway. And so to me, that's not just about The big picture of running a startup. I…”

“If you start your story with Our company is, or our system is, and in the recent years, everything is, our AI system is, or our AI company is, right? But generally speaking if you start your story with that, you focus on your solution. If you start with the st…”

“In a small place like a startup, The hard decisions will always go to the top. Now, if the CEO does not make that hard decisions, the result is always the same. The top performing people would leave. They would leave because they don't want to be in a place th…”

“The only chance for a startup to win is to win on a playing field where better doesn't matter. Where execution isn't as important as gotta have that thing. I'll take any version of it you give me because I am desperate for it.”

“If a customer has the ability to do something other than what you do to solve their problem, they won't be crazy enough to do business with a startup.”

“Startups almost always spend their money in 18 months regardless of the amount? And I said, yeah, I call it Mike's Law. It almost always happens. I said, because once you have the money, all the pressure is on you to spend it.”

“Better doesn't matter when you're a startup. Because better is an extension of the present. Better is when you think the future will resemble the present, but only be slightly different. The way startups win is by being radically different. A startup wins by a…”

“A corporate capitalist makes money by persistently compounding, makes money by extending their advantage, makes money by having a moat, makes money by you know, doing things well. Over and over again in a compounding way. Startup has none of those things. Ther…”

“A startup is a fundamentally disagreeable act in the first place, and there's going to be times you need to be disagreeable.”

“The great startups, they create movements, not so much by criticizing the incumbent, but by showing the weakness in the strength of the income. And then just saying to the customer, Hey, look, you decide.”

“I think some of the best companies actually do have a practice around this. Where, you know, they had a six, 1218 month check-in on new hires. And they then compare, you know, their sort of performance against level hired at and then review against the scoreca…”

“Some of the most time-wasting frameworks have also just come out of big companies, right? Where the context of the big company that may have made that framework super useful within that context doesn't translate to startup or small company or even big company …”

“And so if you invest super heavily on like the whole brand vision from the jump, sometimes it's like throwing away money if you have to pivot.”

“If you're talking to an investor and that you don't have a zero day, go to market exploit that creates attention and turns it into sustainable, lucrative demand. You are probably going to fail.”

“It is so, so important to like understand the boundaries of what you can do if you are essentially disagreeing with the status quo in order to prove that your idea is better. So I've always talked about this idea of not being evil, but being just evil enough t…”

“And so I think that's going to be the case of software. Like as the costs go down, people will just like make a lot more software to improve their lives and to improve their work and start more startups and all of that.”

“And founder led sales is really, really, really important because in the very, very, very early days, when there is no brand equity, when there is no marketing engine running, when there is limited to no reference ability, the founder is the product, right? Be…”

“Most startups are turning non-consumers into consumers, so that's why this kind of fits well.”

“I find it's impossible to get anyone to care if they're already good, if things are good enough with what they got today. Like, I'm happy not using the best possible product if my life is okay, and I have so many other things I got to do, and I'll just deal wi…”

“We like to joke that more companies die from suicide than homicide. And it's grim, but also if the two or three people in charge of the business can't get along, nothing else matters. It's all gonna break apart.”

“If you're a startup, maybe the fact that you don't have that many existing users means it doesn't matter that much if they churn because you're putting a lot more eggs into acquiring the next set of users.”

“You don't want to push them because you don't want to upset them. You don't want to give them difficult feedback. So you're just going to keep hoping it works out. Ultimately that leads to the demise of your company.”

“And it turns out that, you know, according to Noam, Noam Wasserstein, 65% of startups fail because of conflict with founders or the founding team.”

“All the startups anyone's ever heard of have people who are injecting heat, because if no one would inject heat into the business at room temperature, you cannot outperform anyone else. You can't be hotter than everyone else if no one's injecting heat into con…”

“Because if, you know, if an A player leaves I hate it, but it's not a crisis.”

“All the CEOs in the world, if you would ask them, have you nearly died already? And they will tell you yes. And then the next question would be how many times? And they will tell you multiple times. And if they are not, that means that they are simply too earl…”

“That's the only way that they die. Okay. By the way, all the companies in the world, right, they are unable to pay their bills and therefore they die.”

“I think the good advantage is if a customer use Notion, they can address those three, four use cases in one place, especially for our startup mid-market companies, their need for each of the vertical use cases is not as complex.”

“As a startup, your job is to take on technical debt, right? Because that is how you operate faster than a bigger company, right? Bigger companies don't take on technical debt. They pay it usually right away, or they're paying back technical debt. From the days…”

“These are the types of things that us as a startup can do that bigger companies can't just, you know, they can't just pull in Devon, right? They have to, you know, get 30 lawyers in the room first before that happens.”

“I think this is a really interesting piece that you've just hit on, and I expect to see a lot more startups that take advantage of that insight.”

“I think that's probably the best way to boost career is to, you know, to go and to found something, work in a startup, build things yourself with a very small team work in all different areas, because in startup you have to work in all different areas.”

“The key question for startups is totally different. You don't have the luxury to spread your chips. Like you have to go all in. You have to choose one and go all in. You have scarce resources, scarce attention from the market. And so it's a totally different b…”

“And what's going to happen is that if you don't do it, your competitors are going to certainly go to the new platform and your customer expectations change and you have to rise to those customers' expectations. Like they're going to start expecting you to be i…”

“When startups come to me and ask me for SEO help, my first response is don't do it at all. Spend your time on something else. Cause you're not going to be able to grow SEO early on as a in search because you don't have enough domain authority and it takes a wh…”

“I've, I found out very quickly building startups that if you put 20 friends on something, they're not gonna do you that many favors. Like they're not gonna use a product every single day. Cause they're your friend, like 30 days in, 60 days in, 90 days in. They…”

“In fact, I know you probably know this stat, 65% of startups fail because of co-founder conflict, and co-founders are in a moment where they're trying to build the future for their business, but also trying to build their own livelihood.”

“That's often really a sale that's going to resonate with another founder. And for everybody else you know, particularly enterprises, you're avoiding The risk of not making your revenue target next quarter the risk of having, you know, being outdone by the comp…”

“So your designer has to be one of your first hires now in startups. It's not just about the engineering, so to speak, utility, and you have to think through every single interaction of, does this communicate our brand or not?”

“I just usually think the best startup as fat for founders, not necessarily for everybody else is the one you're already working at. And if you're not happy, turn that into your a hot AI startup. It's not, here's the thing. It's not too late, Lenny.”

“It is true that if you bring manna from heaven, right, like you invent something that is literally the next Google or whatever out of pure thought, That sometimes none of this stuff matters, right? Like if you just, if you fully, that's it, you know, it's like…”

“AI is a powerful tool. It's incredibly powerful for existing businesses and existing structures. It's not a great startup opportunity.”

“I would, if I were starting a company right now, I would hire like the best generalist people I could possibly think of. Someone who I think could kind of fluidly move between that.”

“Exploring the kind of uncomfortable Parts of our social existence are things that startups are uniquely set up to do.”

“Don't build a product and a platform at the same time. You know, if you're going to be a platform company, build one. Our first company, we tried to build a sort of a social platform for mobile games and be a gaming studio.”

“I think if you define a startup by number of people or by like the funding round, like none of those things really make any sense. The core thing that defines a startup is exactly what you're describing, which is this kind of scramble energy of things are kind…”

“As companies grow, and we've had the fortune of hiring really great people from other companies that have gone through hypergrowth, things slow down, and you kind of keep telling yourself, we're still a startup, we still move quickly, but you really don't, and…”