The Wisdom Wall

“A lot of times when you go to a team that's six or seven or 10 people, more than the manager, I think it's actually better to ask everybody else that works with in that team who should be fired.”

“if you're spending your time thinking about the person instead of the problem, the person is the problem.”

“Very common thing people say in software, uh, in, in, in venture. Oh, the only execution, the only mode is execution, which is not, which is definitely not a mode.”

“They say, okay, well, you know, quality, price, and speed, you have to pick two. And I think that that is like the most losing mindset in business and engineering and design and whatever the thing is. And that the The, the trade-offs between those three are usually an illusion that usually the thing that can be…”

“what I learned was that for something that has a commitment to end user experience, you cannot do it with open source.”

“the other uncomfortable truths are like the rule is the mostly the highly educated, connected founders do better than the not highly educated, connected founders. Like the top, like people, I think we want to have this feeling that it's egalitarian and or it's a pyramid meritocracy that somehow brands and schools and…”

“great companies hire great people. The best companies can hire anyone. And when I read that, I was like, that is such a You know, such a banger. It's so interesting. Cause you know, again, that's another like Silicon Valley line, which is you just have to hire the best people. Right. But if you look at like the biggest…”

“So from the beginning, we took this very contrarian stance that customizability is stupid. What we actually want is this proven system that has all of the best practices out of the box in a way that the small business owner can't screw up, and we're not going to do customizability.”

“you can think of them as free research and development factories, where they're constantly running a bunch of experiments on the same group of customers, and when some of those experiments Work well. It makes a ton of sense to just shamelessly copy that approach to that specific product in order to bring that benefit…”

“hey, it turns out that the employees who would constantly complain about things not related to the company are actually not a good fit and not the type of people that we need to be really successful.”

“I would say on this point of like micromanagement, I maybe have a contrarian point of view in that I don't think good brands are made without micromanagement.”

“that's probably the cruelest, but most effective training ground to make, um, high functioning entrepreneurs and probably ill functioning human beings.”

“what they really need is a good therapist. Unfortunately, it makes them, if they get good therapy, it makes them an ineffective founder for their next one because you beat that. That intensity out of them.”

“I don't think PM is a craft at all, which is probably evident from my previous answers about, you know, the process. Like, I think a PM is literally the intersection of caring a lot and then having some domain expertise.”

“writing code is not the long pole in the tent anymore, and code is an output now. It's not an input, and the half-life of the, as I will talk about, the typical software development life cycle or the product Development life cycle. The half-life of that is dramatically shorter if you are kind of an AI first…”

“I think it is hard these days to take a bet that is multi-year at this point. Maybe not on the, I would say, Adams-level infrastructure, because those do still take a while, but if it's in, you know, in, in product, in software, because I don't know that it needs to take that long anymore, right, because of the power…”

“if I can do both and learn faster, versus do one, fail at it, and then do something else after that, and that takes me four months to figure that out, versus doing two in parallel, and I learn in two months what I would have done in four, that is like a trade I'll make all day long.”

“The classic, uh, design mindset is make a quick prototype and throw it away. The classic engineering mindset is build durable systems that can last for 10 years. We find ourselves in this in-between, where we have to build systems that last for six to 12 months. At a scale of a hundred million people plus using them,…”

“The first discovery was actually a great one, which is AI products are easier to monetize than traditional SaaS products. The willingness to pay is just much higher, and there's a natural customer understanding that these things cost money to run, and there's this natural equation people have of their own hours saved…”

“You have to take your one value prop and show it in the 1:02 minutes of when someone signs up. If you can't do that, you're toast. And probably like the single biggest lesson that you could take from Gamma was focusing on onboarding actually unlocked the real product's value prop.”

“creative products that are oriented around creating that special experience that are often about restraint and doing less, I don't think are very well served by this mindset. They're well served by creating space for exploring multiple different paths in parallel, dogfooding them yourself, coming to your own conviction…”

“product market fit often is just like a product positioning fit. Sometimes you can just change some things and that's all that matters. And there are some people in the world that want whatever you're building, even if it's a niche product, you just kind of need to find them and, and tell them in the right way.”

“And then you get this hero culture internally where they're the only ones that can, that can solve it. But that's very hard to solve because the only people that can solve a hero culture is the heroes themselves. They have to hire those people and train them up and offload a bunch of stuff.”

“if every one of the big decisions you take turns out correct, you're doing something very wrong. Like, you're not taking enough risk. Something's very wrong. So the batting average, again, like, I say this, like, on big decisions is, like, if your batting average is two-thirds, you're probably doing a good job.”

“and my theory there is if you can't be empathetic about yourself and knowing you and how you use that thing, you say this is your most frequently used AI product and you can't make a feature for that. Like, you know, come on. Right? You're, there's no chance you're going to be empathetic for a brand new customer.”

“And so, you know, if you're trying to sell a product which is purely open source, you know, effectively The price of that product should collapse to the cost of providing it, which is basically kind of a scale of zero, right? So, so there's no business in selling a, you know, pure open source software.”

“What I learned there is true for any startup is that you, you have to recruit great people. You have to develop those people and then ultimately drive revenue as your third thing. If you recruit those great people and they know how to sell the product, then they'll drive revenue.”

“CRM is Salesforce is water to the sales team. That's not selling. You don't know how to sell. You know how to do a deal. It's order taking. And so that's what the LLMs are doing right now. They're order taking. At some point, if you build a world-class organization at one of those companies, they'll win in the long…”

“Why do I want pessimistic? Because I don't want someone with happy ears. If you're happy ears and you're nice and everyone's nice and you like everyone, well, guess what? There are gonna be a bunch of deals that you're not gonna get because people are gonna lie to you. Buyers lie to you all the time. Procurement people…”

“Frank has this thing where it says, when there's doubt, there's no doubt.”

“If you have a money printing machine, you should have that kind of stuff, but for everybody else, it's different.”

“What we understood what happened with all the companies in the last 2030 years that tried to compete with Cisco was that they then ended up selling that. Then the best companies actually start having success. Then they never go out and build the rest of the thing. Then they always just end up being a point solution.…”

“But if you do start a great, you know, point solution or something where you own horizontally one part of the stack, I think the chances of making it to a certain level are higher, but the chances of building a very large business, I think are very slim chances. So if people are interested, I think in doing that, maybe…”

“in a market where incumbents like that don't exist, the initial ramp is easy to get in, but so many people get in, then it becomes really difficult. But with markets like this, with large incumbents, the initial ramp is really hard, but once you pass that chasm, there's almost nobody else there along with you, then it…”

“Normally what happens is like the, the number one company Is number one, not just because they have great product, but because they also have a very strong sales culture and DNA. No, most of the time you do want someone who is like spent. So they know what good sales culture and good sales discipline means. I'm not…”

“But we create a model that we don't bundle things. So each of these modules are sold on their own to create accountability. They will, will never be best of breed in them. If we don't have accountability to the customer, the minute we bundle it, then you can have like three great modules or best of breed and two very…”

“when it came down to it and you probed these questions of what they were looking for is basically they had, they disliked the business that they ended up building. And to me, like, that's a kind of a crazy situation to get yourself into. Cause it's your fault. Like you've built this business. You made all the decisions…”

“In the beginning, you look for people who have a lot of experience. And then you realize you hire someone with 20 years of experience, and they don't have 20 years of experience, they have one year of experience repeated 20 times. By contrast, you hire somebody who's two years out of college, who doesn't know anything…”

“automation doesn't actually work for this IT use case unless it's faster to automate something forever than to do it manually once.”

“I think so much of this legacy enterprise software, it's powerful and it's sticky because of its configurability. And if you're going to disrupt them, you have to disrupt them in a way that actually attacks that configurability head on.”

“And I think what large enterprises want to do is not adapt their process to your software, but adapt your software to their business process. And these large enterprise software platforms like Workday and Salesforce and ServiceNow, they're very good at that. They can be adapted to whatever the internal business process…”

“shockingly, I think there's, there's higher order returns to being technical and being able to code than there were. I think there was this moment where maybe we thought everything would be no code. And I think this era of these models being very good at code generation has actually made it much more valuable to have…”

“AI gives them a chance to compete both on simplicity and user experience and also configurability because you're using AI to set these configurations or maybe achieve value propositions that these other platforms just can't touch.”

“in the whole AI market, it looks like it's very hard to differentiate with models. If you have a good model, you maybe have a three month lead, maybe four months, uh, people catch up.”

“there's a lot of people who say, You need to say no to as many things as possible and focus. Not saying you should never focus, but also you should say, well, for a customer, how could I say, say yes to as much as possible? And sometimes that feels unnatural, right? You're kind of exposing yourself to risk. You might…”

“There were some customers who would buy something because they thought it was neat, and the IT department had discretionary budgets. They're technologists. They thought that something was cool, and it's actually really dangerous because as a startup, you think, oh, I'm building something that is getting traction, but…”

“it could be that what everyone is pointing to is like a lack of a market is actually just a product and packaging problem.”

“People need everything with AI. So that's almost obvious. And now all you really have to zoom into what works and what can work. And where is it going? And you have to look sort of a step ahead and build towards that. And it's a very different art. Like, everything is now stochastic. Like, you build deterministic…”

“One of the big shifts I went through taking on the CEO was I decided that the most productive way to operate would be to shape the company around me, take on the founder role for the company, because I think there is no other way. If you try to fit yourself to an organization, a company, a plan that exists, I don't…”

“Turns out ground truth is never ground truth, right? So one of the things we, we sort of totally changed in our worldview was ground truth is never ground truth. And that we actually have to do comparative analysis of quality and really reframe every customer conversation we have. Around, let's compare two…”

“The second thing that's really important, if you embrace this sort of bet, take risk on hiring, is you have to be somewhat like, the system only works if you also embrace being decent at firing.”

“one of the things I saw at YC were the good companies were good pretty quickly, and then were good for like 10 years. And then they went public. Like they weren't like this, this out in the woods for a long period of time. It's the exception, not the rule. The rule is the good companies are pretty good, pretty quick.”

“It's not come up with the idea and then go find a co-founder. Brett Berson: Why is that a bad idea? Qasar Younis: Because then it's my idea and then you join Brett as really a glorified employee. Because you weren't there at the birthing of the idea. And most likely then the idea has nothing to do with your skills.”

“we actually heard early on from people and allergic, no reaction to that. They were like, Hey, we were using open source stuff and it's super brittle and it breaks all the time. And we just evals suck and observability sucks and we just don't want to deal with this. So We don't want to use an open source thing. We just…”

“I think there's only one right answer, which is it's much better to be overhyped and then fail. I mean, obviously within the realms of morality and integrity, but I was, I sort of learned like, I don't want to be an obscure product that no one cares about.”

“A classic example of this is when companies hire salespeople from extremely successful product-led companies, and they expect the salesperson to be good for their product-led company that does not have product market fit. Um, that is not the right You actually want someone who maybe worked at a company without product…”

“product market fit for me is that when you talk with 10 customers, two people are loving this and want this. That's great product market fit. Now, you need to figure out who's the two, who, what makes them special, who are the segments, and then you can pick 10 of those, and then it's going to be 10 out of 10 or nine…”

“If we don't make money, nobody will make money in this industry because we will gut the whole thing. And that was the entire strategy of like, you know what? It's okay that Uber doesn't pass because Uber's not gonna pay anybody. And we've just removed that. And that's what open source does. It commoditizes the market.”

“enterprise companies cannot compete with us when we undercut them on price, when we undercut them on market share, when we are the developer's first choice.”

“You can't apply their successes. It just doesn't work. Like, great. Century has product market fit. There's nothing you can learn from how we achieved it that you can apply to your business. Cause it was like, Just fortunate. Coincidence, right?”

“And if you are a founder and you're not out there just like representing yourself and your company every day, you're, or as much as possible, you're doing it wrong. And so you still need to charge money. But I think the best founders I know, even if they're not charging money yet, they have cemented so much brand…”

“companies don't really do it that much because I don't, I find they often think about the, the resources as number of people, not, not necessarily like the output of those people. So it's easy to say, like, we need to hire like a hundred more engineers, but maybe you only need to hire 10 more engineers if you just…”

“in the end, the productivity of any company comes from the ICs, like what the actual, what is actually the work output and the ICs engineers or designers or someone are building that output. So I think if the tool should be optimized around anything, it should be that, like to, how do we make, help them to complete…”

“I noticed in all of the companies I worked at that actually the, the ICs and the high level leadership was, I think more philosophically aligned because I think CEOs and a lot of the high level leadership, they just want to see things happening. They want to see output. They want to have progress. I see, I think…”

“it's never been, even in the beginning or later stages, it's never that like we Listen to these users and then we build what they want or what they, they say. We went there, like, it's more like we have that model in our heads. And then if something doesn't quite fit into it, then we, we try to like ask them more…”

“You shouldn't probably emulate. You should almost do the opposite what all the other players in your domain are doing. And maybe you can take inspiration from some other companies in other domains and do something like similar there.”

“We could still be more opinionated on the lower levels where there's more of this volume and need for structure because there's more people and more things happening and the more flexibility you introduce, it multiplies a lot more. But once you get to the very highest level, you might not have that many things in there…”

“why quality doesn't happen in most companies. It's like, it's just because it's not incentivized. No one ever says you should do it. It's almost that no, we just want you to complete this task. We don't actually care how do you complete it too much. We just want to complete it now. So you incentivize the speed, but you…”

“Like I always tell whenever someone new joins, I never tell them like, oh, we have a market risk, like just identity is not a market risk company. It's fundamentally really an execution risk and it's a very high Execution risk because the idea is just so obvious.”

“You can get to a point where you're proud of things you should no longer be proud of. Maybe said a better way, the things that you're proud of can inhibit you. And so, you know, once you've been Bootstrap for 10 years, and everybody's like, wow, you've grown this great company, all bootstrap. How impressive is that?…”

“The other thing that came out in all of these, like, conversations with folks is, like, if your values aren't aligned, there's, like, literally no way it's going to work. I think it's just actually pretty hard for there to be, like, globally relevant execs. Like, there's, like, the right exec at the right time for your…”

“new leaders have in almost every single scenario a huge incentive To say that they need to change the strategy.”

“we would have these, like, reverse demo conversations where I wouldn't traditionally demo the software. Basically, they would demo, like, they would demo it themselves. Like, they would sign up Share the screen, do the flow. I would help them do the individual steps, um, through zoom annotations, and they would learn…”

“First, platform fees are inherently challenged. They are not great pricing mechanisms, and the reason for this is, first, it doesn't scale. After the first year, you want to keep raising the price because you want to, you know, you want to create more margin. It's very hard to increase a platform fee. Procurement teams…”

“when you look at other B to B software, no one invests in it. And so when you have something that no one invests in, And everything kind of looks the same. A lot of early stage software is just about standing out. Because you're trying to make news about something, you're just trying to stand out from the crowd,…”

“If, if someone on your team comes to you, you've already lost the game because they have been thinking about this. I promise you for weeks, if not months, because it takes a lot of courage and bravery to like go up to your manager or the founder and ask for more money.”

“When you sell to software engineering, sometimes you can go PLG for a lot deeper in the journey and, you know, Stripe and Twilio and others have, have done that very successfully. But data for a variety of reasons that are probably too boring to get into ends up needing to be sales led and it, and most of the dollars…”

“on the marketing side, A lot more rests on the go-to-market and having a good go-to-market story to tell and is less, a little less about the quality of the product. The quality of product obviously always matters, especially in retention and other things like that. On the security and IT side, quality of product…”

“I think it's easier to scale out selling to IT and security because there is a process that they're going to go through that's well understood. They are going to be very rigorous in testing out the capabilities and making their decision. And I think on the marketing side, it just, by and large, the rigor isn't there.…”

“Shocked how many people I interviewed that were senior directors, VPs, never fired someone before. I was like, okay, this is a pretty big red flag to me.”

“One thing that I've learned and I've learned this from, from our CEO rubric and I, it's, Just really gotten embedded into the way that I operate is that you need to just have one killer differentiating feature that you can sell on to begin with. So whatever that is, it might be a killer feature around the performance…”

“when you find you probably already have the right answer and you probably just don't like it. So the reason you're not growing is because you're missing some important piece of information about the business model, about the market, about your customers. When you find that information, you're going to grow faster. But…”

“ads, you know, let's just be specific. We're talking about Meta and Google. Those are the main ways you buy, and they're sold at auction, which means ultimately they're going to go to the people who can pay the most, which means the most well-funded companies, the companies with the best tracking and analytics, the…”

“ads are a very good way to get traffic quickly for testing. So suppose, you know, you're an early stage B to B company and you have very little traffic and you've come up with three, you've interviewed all your customers and you found there's three different buckets of goals that they're trying to achieve. So you can…”

“The only people who can start and build great companies are people who hate corporate life. And the people who love corporate life can't build and start great companies.”

“it is much easier for someone to switch domains that they work in, but it's very hard to switch like the type of funnel that you've operated. Because if you're doing enterprise tops down sales, the type of channels and programs and initiatives and the type of materials that you might have to create to reach that…”

“Failing on the early side, you at least have a chance to, like, course correct, right? Because if you don't spend all your resources and burn out completely, you can keep going, and maybe the world catches up to you, or maybe you make the world catch up to you. Failing too late by being too late, somebody else got…”

“there's not really much of a prize for being pessimistic and right about these things. Ok, you get a ribbon. Who cares? The prize is for being optimistic and right.”

“you can't go short on, like, technical, technological revolution, right? You can't, like, short solar or some crazy shit like that. It tends to be wrong. We tend to figure stuff out over time. You know, at best, you're right for a little while, and eventually then the world figures it out.”

“I think there are lots of businesses out there that don't fully understand that they're predicated on the expense of creating pixels. And so similar disruption is in the works.”

“The easy way to understand this is when I say you should think with the model, but plan with code because the models are, they're stochastic and fuzzy. And so if you want something reliable, you should build kind of a scaffold around it in code, something executable. And then you just force the model to do the thinking…”

“the things that work well with LLMs have this shape almost like a cryptographic trapdoor. There are like things where it's started work for the human to create the work, but easy for the human to validate the work. Those are, those are the things that tend to have high value. That's challenging in the coding domain…”

“There aren't that many that helped you become a billion dollar company. It's basically sales, virality, what I call like content loops, which is we distribute content directly to, you know, Google or to social networks to bring more people in, and then those people create content and then you redistribute that, or…”

“And the challenge with paid is It always looks better yesterday than it does today, unless you have a network effect business where the product quality is getting better, faster than the quality of people you're bringing are getting worse, right? Cause you always target the best users first and paid. So generally it…”

“It's generally lower take rate. If you have a take rate model, it's gonna be more like five percent versus 15%. And then of course you're paying the payment processing. It's harder to build a massive scale business. So you see fewer venture wins in that category. Whereas if you own demand, which is generally the most…”

“I generally advise founders against marketplaces phase two of the company. So there are a lot, a bunch of people were like, ah, SaaS to marketplace transitions. That's the model. And I'm like, name an example in the last 10 years where that's actually worked. Because running a SaaS business is not simple.”

“I don't think cross-site network effects really kick in until you're like past 50% of the demand, probably even more than that.”

“I just don't think there's a way that a public company that raised like a hundred million in IPO is going to outcompete. Companies that have raised four billion dollars each, I think, in Uber and DoorDash like to crush you.”

“I think one thing marketplace founders need to be Careful about is if you are aggregating supply and demand in the market and someone else is aggregating the same supply and offering it at lower cost or with a higher frequency type of transaction, you need to copy them immediately or you are going to get disrupted.”

“TAM is kind of a misleading metric for marketplaces, because in all the biggest marketplaces like Uber and Airbnb, it looked like there was no TAM.”

“So what needs to happen is that the product needs to get better faster than the users you acquire get worse. And network effects are really the only scalable solution that can make that happen.”

“One is discounting to product market fit does not get you to product market fit. So in a marketplace, you are selling people on the value of the selection, on the value of, you know, the service. And if you then give a five dollar discount, then you start changing the value prop to saving money on service instead of…”

“A bunch of people tried to copy Uber's launcher strategy, and then a bunch of people like almost went bankrupt doing it because it's really expensive and they weren't raising billions. You didn't really understand what your playbook required. You were just kind of carbon copying a very different, you know, marketplace…”

“the art of saying no is the best thing a product manager can do to actually eventually win in a product, right? Because you, typically have like one company. You're basically jamming their features. Oh, I'm paying you ten million dollars. You've got to do this. If it doesn't align to where you want to be long-term, you…”

“Means if you take a VMware or any other enterprise company, they package it up. It's all good enough. We'll be number two, number three. Distribution, ELAs, life is good whether it gets used or not. Can't afford to do that. If you are in the developer land, I can't afford to be a mediocre offering, right? Like, ah,…”

“The CEO job, the most successful CEOs act with impunity in the work environment in a way that number one, a good CEO doesn't really think about it. And number two, a good second in command does think about that and enable it.”

“Every successful outcome is led by a founder who is deeply impatient, really impatient.”

“The cure to politics is not to lecture people about being apolitical. It's to make sure the team has too much to do.”

“I'm friends with many CEOs who I've, you know, met over the years of having been one and then doing this job, and the folks who are really into the coaching and really into the touchy-feely stuff for themselves on the balance just have not performed as well as, as executives.”

“If you ask someone for relevant experience, then if they have some first advantage is that like you get to integrate their experience into your context, as opposed to trying to give them a bunch of context so that they can chew the cud for you and give you the advice far more effective to just get their relevant…”

“All alpha, all outperformance relative to the index comes from anti-patterns. Patterns are the things people do over and over again... none of it is predictive of success. It's the anti-pattern.”

“The contrarian play behind Wealthfront was that people assumed that delegators wanted to work with people, and that do-it-yourselfers would do stuff online, do it themselves. And Wealthfront, no, no, actually, there's a new generation of people. They are very comfortable delegating to software, and they'll be…”

“In this case, I don't think you're looking for product market fit because in the end of the day, product market fit is for a category, right? Do you need forecasting software? Well, I do. I already have one. So it's more about call it like maybe product completeness questions.”

“And so our team is really good at politely declining to engage, right? Not just because the use case doesn't fit or it's not ICP, but we qualify the champion out, even if it's a CIO.”

“You know, our kind of tests on inference on quality for agent use at work. It's just transformers. Just, it was current capabilities, really not able to, to do what, what we wanted them to do. And so new architectures that we're working on are super, super promising.”

“Like, it's fine when I am, I've indexed 50 pages, but when it goes to 50,000, you know, I can't get this needle in a haystack out of my kind of VectorDB approach.”

“in the early innings of a platform shift, you can be narrow and you can, you can find a lot of product market fit, but towards when, when the thing mature, say, you know, web or cloud, what have you, you actually have to be a lot more ambitious.”

“And here's a, here's a controversial one. There's times we spent a year. I'm like, you don't need to be here anymore. You have learned everything that you're going to learn here at Slack. It's time to go somewhere else. And I wouldn't say it like that, but there's truly a healthy part of the job is when you're like,…”

“Winning the enterprise is really, and winning a more traditional PLG motion, it's almost like two separate companies. I think it's a very different way you think about building product, different way you interact with customers, and certainly a very different way to go to market. And as a result, I think even the…”

“I think the big mistakes companies make over and over again when I see is when they try to blend, they think they can, they think they can just seamlessly evolve. And as they scale and Into an enterprise company. I think it's, I think it's a lot more complicated than that.”

“as you build the security stuff, it does unlock major expansion in, within your customer base, right? The companies where you have good organic usage, many of those companies will start paying you 25, 50, a 102 hundred K. And so you're taking in this data and you're like, wow, it's working until You don't have enough…”

“as an executive, all I care about is driving enterprise value. And then really the only things that drive enterprise value are driving more revenue, lowering costs, risk mitigating, right, on that level. And so your pitch at that point is like, well, look, uh, look, so many teams are being more productive. You see,…”

“And so Dropbox and Slack, if you ask me what's the company value, well, the company value was securitizing, in a way, the bottoms-up problem that we created for them, which is all this rogue usage.”

“all categories have to go through the enterprise. All winners have to win through the enterprise. There's very few, I really can't think of many of any companies that have become the category leader without winning the enterprise.”

“Phase three starts the same time phase two starts, because it takes that much time to identify the problem, identify the path, and then start building the right team to execute that, that play. It takes a long, long time.”

“This is something that I see a lot of PLG companies get wrong, which is they, they They confuse segments and motions. If you take a step back, traditionally enterprise companies are set up and they are split by segments, SMB, mid-market enterprise, right? And of course you have like big enterprise strategic accounts,…”

“when the company finds product market fit and you need to build repeatability and scalability in the company, these same founders throw organizational hand grenades into their own organization and culture, trying to keep that chaos going on inside their company. Because without that, they feel incredibly uncomfortable…”

“the mistake that people used to make was only replace the founder in the 20th century to take a company public. We forgot that that innovation cycle might be every, you know, two to three years and you could get liquidity for the investors, but then the company was dead because the innovation died because you just were…”

“I invented customer discovery for me, which was to inform my vision, not to create a goddamn focus group.”

“They were world-class number twos and almost never are world-class number ones.”

“So I sure hope OpenAI, Google and Facebook, and even Apple continue to slug it out at some point. Because if they don't, innovation will die in the browser or like the browser did, it will die in generative AI.”

“Kafka, you know, that was one of the reasons why we couldn't or we didn't sort of narrowly focus on an ICP like traditional companies do for good reason. It was because, you know, the Kafka adoption base was so broad and for Confluent to quickly convert those users into commercial users was so important that we Used…”

“for the success of an open source company, all the creators should be part of it. And when that doesn't happen, you have two companies and they're competing on things they shouldn't be competing on, which mostly comes down to pricing and, and it's just a race to the bottom.”

“And so finding the way of harnessing that as a feature rather than a bug, I think is going to be challenging, especially when one of the perceived shortcomings of your product is actually going to be, is like the core of what makes it function. I don't know that there's been technology in the past where that's the…”

“one challenge of the last decade, right, is that resource allocation was largely dodged by many companies because they just Decided to spend more and hire more folks. And so oftentimes, um, the real constraint was, like, hiring velocity on a given team and your ability to kind of, like, get recruiting aligned with your…”

“I think one of the lessons in management over the last decade has been that You know, managers are people leaders in that it is micromanagement that it is bad to get into the details. I think this is like an anti pattern because it creates disengaged and like sort of like context free leadership”

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

“what we realized as we kept building those products was starting from like research that just, uh, like Became possible and identifying some coming, having, uh, some hypothesis of the ways in which it could really, we could build like really strong and valuable tools around was a development process that actually, uh,…”

“Um, I, I just, I really think it's hard to come up with a great, like scoring framework for how to pick out the next 10 features, because I found that every single time that we tried to apply some sort of rigorous, like scoring framework to difficulty and reach and You know, like customer tears. It was just like a…”

“A good business makes a lot of this stuff a lot easier. Like, if you're making good money, if you're growing, if there's plenty of opportunity to go around, there's plenty of money to go around, salaries and bonuses and things like that, everything gets way easier. So, you know, if you're having people issues, you…”

“we had, we had this rule, don't hire till it hurts... One, it meant we did every single job. So we understood every piece of our business. So when we hired somebody in that meant we knew exactly how they were going to be effective, what was going to help them win. And it also helped us Performance management. We knew…”

“I see a lot of companies today that are ex Apple people who've built amazing things and they go off and they spend years and years toiling away and never really ship anything. And, you know, I think they have this sense of like, it needs to be As good as the last thing they did. And, uh, when you start from zero, it's…”

“as we, I think, trend towards artificial general intelligence, the definition of correct or the definition of whether something is, you know, valid or not, It's becoming increasingly subjective”

“When I'm going and having these conversations with leaders, and this is, I think the standard conversation most people have is it starts with leadership. If we're moving too slow, it always does. We've always believed that we've been more clear. We've created more clarity. We have aligned people better than we have.…”

“Dropbox hit a home run basically out of the gate. And there was kind of an expectation that that's how you built products. And like people came from different places and very different experiences, but pretty deep in the culture was this idea that you build it. And then, you know, Coin a phrase, they come and, and that…”

“I think the canonical example of this is Google, by the way. I mean, I think that Sort of in industry. Now we've kind of learned you hire people out of Google and they show up and they don't know how to operate because they've been such a determined high functioning thing where all of the tools were in place and they…”

“one of the things that people ask me is you look like you've worked with a bunch of great people. Like, do you just like bring them with you to every organization? And, and the answer is, of course not. Like every organization is different and partially I need the people who grew up in this organization to translate it…”

“Actually, one of the, the early stereotypes about engineering managers in our industry is as the shit umbrella, you know, just gonna keep people from being distracted by all the crazy. And what that is, is those teams end up just drifting off. You know, you talk about like coordination and alignment and shared values…”

“It is really hard to just go out and create a brand new category and Lattice did a tiny bit later, which we get into, but we really redefine categories. And that's, I think a much easier way to get your traction in the market because we could go to companies and they already had a line item in their budget for…”

“If you don't invest in marketing in the early days, you're going to stall out and it might not be at a million ARR. It might not be at two, but it's definitely going to happen as you get past 10 and 50 and so on and so forth.”

“one of the things that's unique about founder CEOs relative to like a professional CEO is you do, You do have this extra chip of moral authority that lets you shake things up and keep the startup feeling like a startup even when you are at scale, and one of the ways you exercise that is by staying deep in an area.”

“if our part worked, and the product piece didn't work, then, like, we still failed. So, those teams had to be fused together, and it was sort of a shared fate. I had no tolerance for this, like, hey, just because you're in infra, you don't need to care about, you know, the customer.”

“if you want to be able to really, like, accelerate through one of those steep technology inflections, The people who generally know the best about the technology are actually the ICs. So you have to, like, elevate them, you have to, like, protect them, you have to, like, expect more of them, and not have this, like,…”

“when you take some layer of your kind of core stack, and it's like outsourced to this vendor, and vendor, you know, could be great, but when I was at these companies that were, you know, Kind of N of one in terms of what they were doing scale wise. They weren't making a product for us. They were making a product for…”

“Now what we're finding, actually, is that all those guardrails we put in place are holding these much more intelligent AIs back. And so we're now in a mode not of even adding functionality, but trying to throw things out, loosen the requirements, and let AI do more overall.”

“This also, I think, came from perhaps trying to build for durability and moat before building for adoption. And I think you actually have to go in the opposite order. You have to first win adoption, which is a kind of a grueling fight with someone who is changing their workflow and only then build some of that…”

“particularly in this world of rapidly advancing AI models, it's actually a really healthy instinct, because the less you build as product surface area, the more that the AI can actually fill in, in actually the white space.”

“I think probably the biggest difference between the Excel workflow and the PowerPoint workflow is creativity and taste. Um, uh, there's less objective definition of what good looks like, um, and there's much more room for the user and also the brand to express themselves. Um, that's what makes it a really fun problem…”

“err on the side of building fewer knobs and controls, because all of those become things that you need to maintain and honor over time, and they may end up becoming irrelevant as AI capabilities advance.”

“presentations are a naturally episodic use case, which means we can't expect on our prosumer base to have more than a hundred percent net revenue retention.”

“Craft can no longer look like going into your little studio and tinkering for several weeks before coming out with something to show for it. And craft also doesn't mean that all of us can feel the same ownership of the product through consensus. We actually have to take these blind leaps in the dark often, put…”

“Once you say that to people, the vast majority of people I've ever worked with, Their reaction to this is, hey, Eric, thank you. I really appreciate you caring about me enough to give me that feedback. And then they do their best to course correct. And it might not be instantaneous, but over a period of time, you know,…”

“I, I don't think it's fair to say that, Hey, no matter what the decision is or what, what, what you're talking about in the context of the business, that faster is always better. I think that's nonsense, right? And there's plenty of examples where you don't want to do that.”

“And in some ways, to me, that's like the ultimate asset test of, did you do a good job or not? And you know, my own lived experience is like, every time I've thought I've made myself useless and obsolete, like there's always been some new opportunity, right? That even at the company that I'm at that came up, boy, we're…”

“But I think if that's the main reason you hire someone. I think that oftentimes doesn't work out because you end up overlooking like all these other things that are far more important in terms of like what that person's ceiling is. You know, I was a consultant myself, so I don't mean this as a diss, but it's, I think…”

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

“there's kind of two outcomes that are great. If you start a company, right? One is you retain control of it and it becomes huge. The second is it fails quickly.”

“It's very clear to me. No, you don't half-ass it. You just go all in if you're going to do remote. We went completely async, and now, actually, I think it's a, a superpower for us.”

“You could have any iteration of a message across a bunch of different platforms that you could automate and test and, you know, quantify, whatever. But, like, a single breakthrough idea even then was far more effective, right?”

“Dropbox was a tool for everyone. So that made it harder to be specific about what needs you were serving even as you moved into enterprise. Whereas like, Figma was way more focused on the core audience, and even for prosumers, even for SMBs, it is a professional use case, and so that has allowed us to be really clear…”

“SEO is now like, how do you have, how do you grab attention within LLM search results? The consideration phase of helping people, you know, feel comfortable with your product is now mostly third party conversations, right? Through social or, or other places. They don't only want to hear it from you. They want to hear…”

“I think in the enterprise, it's very similar and it moves faster, but like change management dictates success in the enterprise more than technology.”

“You need one person. Who is responsible for owning the strategy of go to market? And like, for me, that is like basically anything revenue generating or customer related ideally is under a single person. Now that person's obviously accountable to the founders and to the board and all these other things, but like there…”

“The difference is you have to be willing to give up some level of autonomy when thinking about the product. In a founder-like company. Um, and you have to be willing to, you have to know how to influence really well, and you have to be able to understand what influences the other person.”

“I am a firm believer that if you add value to the customer, you will find a way to capture the value eventually. And yes, I almost think of it as if you cannot capture value, then you are fooling yourself that you added value to the customer, right? Or enough value to the customer.”

“If all you're doing is what customers are asking for right now, I think you'll get left behind.”

“Here's why you're flying at a lower altitude, because you're trying to change the way people work. You're trying to change people, because you as one of, as you as the senior product and engineering leader are the catalyst for change right now, right? Because otherwise people will just keep doing what they do. So I…”

“right now, if you are not spending 50% of your time thinking about what Your product will look like, what a value it will deliver. It's just gonna be hard to compete.”

“even one person can push, pull a performance of a team down by 20, 20, 30%, right? Because other people are carrying the weight.”

“We found that to be extremely indicative. That really, really, we've, everybody, I, I think we can plot out on an almost, almost perfect correlation between the strength of references and the strength of which, uh, somebody actually delivers.”

“I think that the, where somebody stands in terms of their prior experience at this point right now, given how long of a time that these tools have been around is, is not necessarily a great predictor of how much they'll lean into it and really adopt it.”

“as an executive that starts these new S curves, one of the things I've learned is that it's my job to protect those S curves, because what's gonna happen is even in a, uh, a small organization like DoorDash and really in a large organization, Everybody tries to kill the new thing. They just try to kill it because it's…”

“It's very noisy. It's a batting average thing. I think people spend too much time thinking that they can engineer that process to be perfect. I, I much rather, yes, we're gonna interview, yes, we're gonna look for skills, but then we're gonna bring them in and we're gonna see whether they succeed or not. And I think…”

“One of the things that I do is I tend to be very initially tops down in goal setting. A lot of companies are in teams are bottoms up in goal setting. And I found that that is not a great way to have ambition.”

“I think CEOs need to know, you know, about 80% of what their executives know about their function, I think, over time. So really kind of learn that discipline. Not enough to be good Add it, but enough to be, to know what good is and know if it's going well.”

“I think inherently that a second product is always. Kind of irrelevant to people's main goals, you know, and the, all the pressure of a business is to satisfy the customers that you have, the big prospects coming in the door, that, that kind of main flow of business becomes this like magnetic force.”

“So I found that to be very true in hiring where, you know, people who just, you know, act like they have, they, you know, they just have to fight for their life to go hire this team by themselves as if there was no recruiting support and they're just really devoting a ton of energy to it. Like that, those people are…”

“the more disconnected you get from those, like when you start to become more of like a professional manager, I'm just guiding the team, giving strategy and things. I think you lose a lot in making sure you're building the right thing for customers. Cause if you're not in those meetings, if you're not like selling the…”

“Hey, I care a lot about product quality and building an experience that's like well-crafted and beautiful and usable and customers love it. And you don't necessarily have to do that to build a great company.”

“Can we just get some bullet points and, like, make a decision here versus, you know, it's some eighty-page PRD, which I just feel like is kind of, like, pretty outdated at this point. Um, and at that point, I'd much rather just get, like, a V-zero or Figma make prototype or just show me pictures, you know, um, to see…”

“I think when it gets, when it feels like someone's just becoming devil's advocate, that becomes negative from my perspective, because it's just like, I'm just trying to find issues in everything and any plan you can find issues in, you know what I mean? So I think trying to cap that to like, what are the impactful…”

“I think what you gain is a faster decision-making process. Um, so when you want to go through and decide, hey, do we need to do this big technical re-architecture, and that's gonna trade off against some product features, you need to go through and, like, make those. You have, like, one person that's just gonna go make…”

“I think when you're still in the thousands, though, like, you should still be doing it, and I think that's part of our philosophy. Like, at Vanta, I think we really expect people to be in the details, and that's something that I believe a lot. Like, It's just hard for me to think about how I can coach an engineer, a…”

“There's definitely product managers who I think they're, they don't know enough about the technical side, which can be fine, but like can't really appreciate the pain engineering is going through and like what on call is like because like they've never really done it and why we need to make this more sustainable and…”

“We ask people to write dates and commit to them. We expect us to be able to hitting, like, 90% of the dates, which I think is, like, reasonable. If it drops down to 85, I'm not worried. If it drops down to, like, 80 or 75, I start to get worried. Like, I want people to take risk, too, and I don't want to build a…”

“And, and I think if you have second line leaders in your organization who don't know how to sell the product and, and say, Are they hiring great salespeople? How do you know they're hiring great salespeople? How do they know what a good sales call looks like? Because if they can't sell the product, then I, how can I…”

“And I'm going to pick the, the athlete, you know, over the, the industry expertise every single time.”

“people in Silicon Valley Think because they've made a lot of money that they're exceptional. And that's not true. There's so much luck that's involved in, in, in what we do.”

“if you are selling a product that is worth anything, there's some competition that's trying to eat your lunch. You have to be hyper paranoid about that competitor. Like the worst thing is like, if you do a forecast review with a sales team and like, who's the competition? No one. Bullshit. You're a bad salesperson.…”

“A lot of founders, Guillermo's a good example, John and Patrick were examples of this well, are like excellent brand marketers, but that does not a predictable revenue engine make on its own.”

“I think if you help people understand that anytime a customer is having an actual issue, you should be at least CC'd on it for every single customer. You can actually drive a lot down.”

“So what that enables us to do is because the hardware is for us to manage and us to make sure it's great, we maybe might choose components that are 20%, 30%, 40% more expensive than a traditional vendor might, but that is only marginal for us compared to the entire margin for them.”

“The job there is just get it working first, then make it fast, then make it secure. You don't need design partnership there. Can you actually process packets? Is it actually working? Is it fast and is it secure? Because no customer actually, um, understands that part.”

“If you look at businesses in the modern sense in the last 50 years, The three times businesses are usually rewarded is when they innovate on product and technology, or they innovate on how they deliver that. You know, somebody figured out SaaS, before that somebody figured out CDs, somebody figured out USB, whatever.…”

“if they had decided at the beginning that the scope was a little bit larger, generally my rough intuition is it's only 20% more. But it actually ends up enabling you to capture a lot more.”

“When we go build chips, for example, I actually think the right thing there is to go as slow as possible because taping out a new chip, then building it is incredibly hard on ramifications on the mistakes you make.”

“I think with smart people, if you ask this question, you say, how is it that every problem that could be a sales problem, that could be an engineering problem or an operations problem, that could be a design problem. They can be exactly solved in 90 days, but it can't be that everything is solved in this exact thing.…”

“For most enterprise software products over time, the rule of thumb that I've learned is that if you have delivered value to 25 customers, you have a very strong product market fit.”

“if you don't have experience managing salespeople, try not to learn as on the job for the first time there. If you can, you know, you have the money and, uh, ability to recruit a senior person, do that because you're de-risking your learning and a lot of things that, that, that will come in.”

“Would you rather own, you know, a hundred percent of a ten million dollar business or 10% of a billion dollar business? Like, of course, I think unless you, you really have some obsession with ownership, but I think most of these things are confusion about ownership versus control.”

“of B to B deals that seem 99% likely to close, 50% of them fall through.”

“I think there's just almost pure downside in listing these things out to investors.”

“And I think that you gain more of an appreciation for how the other EDI businesses ended up where they are, because they got to one of those paths and they said, all right, like this is gonna, this gets us kind of part of the way there and we'll fix it later. And they, they, they stayed there and ended up on this kind…”

“what you generally see is that companies are able to ship for some short period of time, two years, three years, and then the system ossifies and then they go and they're kind of stuck with that system. Going forward, and that's basically what they're gonna sell. The question is, have you built enough in that cement…”

“there's a myth that the best entrepreneurs are, are risk takers. When in reality, the best entrepreneurs are, are risk killers and they're trimming away failure paths. And Thing is when you trim away a failure path, your odds of success go up.”

“It's when people are, are, are buying the product despite all the things that it doesn't do. And the deals are closing anyways. The deals are closing anyways, and everybody's so happy.”

“The reality is that most people don't care about the product only being 80% as good. For most people that doesn't matter. They're not willing to pay a lot more for that incremental, incremental piece.”

“I think that there's more to learn from the category of discount retailing than there is, you know, in software than there is to almost any other category.”

“Always focus, focus on improving quality because the quality gains usually materialize. If you say like, okay, we're going to reduce the defect rate or we're going to, it's just like a very measurable thing. And, but what you find is that by improving the quality, the costs usually go down.”

“you find that most of the things that people warn you about don't come to pass. And like most of these edge cases don't come to pass. I think it's a little bit different in consumer with fraud and stuff like that, but it'd be to be generally don't need to worry about those things.”

“And Verkata owned the entire platform, and so it was really cool to be able to sell a better camera to people that were going to buy cameras. And then you could also, by nature of selling cameras, also sell them these really cool AI capabilities, this really cool video management software platform. But you did that by…”

“these enterprises, which historically are very late to the party, they're feeling a little bit more momentum around inter internally, uh, and pressure from, uh, the board and the C-suite to start implementing or at least exploring AI solutions that those kind of two factors met. We had a product that was ready for the…”

“There has to be top-down alignment. That's what we found, is that there has to be alignment from senior leaders that this has to be done. Because as you get into larger organizations, the actual folks doing the implementation, it can be a very large team. And the chances that all of them are going to be completely…”

“I think in many ways, what the forward deployed engineer role has actually replaced are the implementation consultants for large organizations, large companies like Workday and ServiceNow and Salesforce that are customizing that software to meet these organizations needs. Now the forward deployed engineer is coming in…”

“And it's also a mistake that actually the really good product leaders do is because they're so focused on prioritization, they never touch the P twos. P two stack up and you can get a lot of them that just completely erode the product experience. And if you're never having anybody that looks at the P twos, you're going…”

“Everyone wants to do the same thing over and over again. And therefore we thought there is value in actually optimizing the most common workflow.”

“Instead of one-on-ones, we try to do like smaller groups of discussions, like one-on-three or whatever, one-on-four. And we try to bring like people from within the team, but maybe someone who joined recently, someone who's been there for a while, someone who's remote, someone who's in office, like different types of…”

“if you hyper optimize there, there's a risk that actually you build something that is, is so narrow that it ends up not really providing leverage in other, other industries. Whereas if you take the other approach and say, I want to actually engage with a broad market, you start end up finding these, these…”

“oh, you know, what we did was we started by first putting it in the, the VP of safety's own car so they can see that we're doing it ourselves. And then we start by putting it on the five safest drivers cars, the absolute best ones. And invariably there is an accident or a near miss where that camera shows that they did…”

“If you're building Airbnb and you want to transform hospitality, you don't start by selling software to hotels that might make hotels a little bit better, a little bit more efficient, whatever. Um, but it doesn't massively transform the experience for the end user, for hosts and for guests.”

“one of the pernicious things that companies get into is they start to tolerate errors of inaction. They're like, well, I didn't do anything, so I can't be wrong. And, um, and they start to punish errors of initiative and boldness.”

“I think at the time, and still you get a lot of onboarding that is coach marks. It like points over here and says, Hey, you might want to do this thing. And you click through the steps at the end of it. You've totally forgotten every single step. And you're just left with a blank page again.”

“building community is all about getting individual users to love it and talk about it to, to other people. And that kind of growth doesn't quite work in an enterprise setting because you end up with a very disorganized and chaotic network graph inside an organization. And pulling that together, finding this one…”

“if you start in an idea with like, You know, if there isn't like a societal level trend that's pushing your kind of space forward, which, you know, I think was true in FinTech in 2017, or it's true in AI now, like it's very hard to iterate around it.”

“So I think it's like, especially at the start, like to spend all your time doing the thing that like you're the least capable of doing and the least capable of proving to the world that you can do.”

“I think it's very hard when you abstractly talk to someone and you're like, would you use this thing? It's, it's very hard to like reliably believe their feedback. At least that's what I've found. And maybe there's like ideas where it's like, you know, some people are like, yeah, I talked to 10 people and that's how…”

“if in my opinion, at least, and I think this actually bared out that if any of these things were missing, people would not adopt it. And I didn't think there was any point in launching with one of these things missing because the only thing we'd learned is we need to go build this thing.”

“You just work 10 extra hours, that, you know, that compounds, per week, that compounds in significant ways. In an annual basis, it compounds with three extra months. And, you know, Brett versus Brett plus three months, Brett plus three months, even if you waste two-thirds of the three months, because you just hang…”

“I think if you only like, if you let you come out of college and you go straight into like being an associate and then you become like a partner, I, I think you don't realize that the, what investors see and what actually happens on the ground is like actually quite different.”

“Just like a craftsman, if you spend a long time on it, you will just get better at it. Now the question is, there's some craftsmen who are already at the LeBron James level, and they're going to get to the next level, and there's some people who are like me, and they're never going to get to LeBron James level, no…”

“After a good co-founder, market timing is everything. It's the beginning, middle, and end.”

“I really believe the co-founder thing is, is, is first and foremost, and that there's really no way to, I think there's, It's very difficult to compress that into like a two month or one month thing. You need that over many years where you see this person evolve, they get married, you see them, you know, I've seen…”

“when you verticalize all this stuff, it's so expensive that literally the costs will crush you.”

“Like if your product isn't selling for some reason, then it's almost always pipeline.”

“And then I did something which I honestly don't think any founder should do. Um, we're talking about product market fit. This is almost a surefire way to prevent yourself from finding product market fit. But I sat down and I said, okay, I want to start a company. I understand this type of technology really well. Let me…”

“I think in the world of early product building, you actually need to be like ultra paranoid about repeatability. And you need to assume that, you know, give yourself a little bit of credit and assume that you're somewhat charismatic or Entertaining or whatever it is and say that, hey, this person seems interested in my…”

“I think personally, my perspective is even if you're trying to hire like a, a pretty good, well-rounded and, you know, skilled group of people that's even, you know, 40 or 50 people, it's very challenging to get everyone to work on weekends. And so we don't, that's not been a part of our culture, um, even since the…”

“I think if you have to convince people, it's super unlikely that you have product market fit. Whereas if without convincing people, they just find their way to the product and then they've, they're already convinced or they've convinced themselves very quickly. I think it's a, it's a pretty clear sign.”

“payroll data is very, very powerful, um, because onboarding is so complex. There's so much that you need to, we need to know about you as a company in terms of your employees and where, Where, where they work and how much they get paid and like your company address and like your onboarding process, like everything…”

“software is not that hard most days. Most of what we build is, and this is why the code gen thing is fascinating because most of what we build is like really low complexity code. Like it's a registration form or something like that. It's not a hard problem. It's been solved for decades, right? It doesn't really change.”

“Do not start a lifestyle infrastructure business. It doesn't work.”

“here's a mistake I think of all founders. Not all. Majority of founders make. And, you know, we know the SaaS majority of founders fail. Maybe this is related. And I, and I'm just purely anecdotes from the companies I've invested in, and some of them are like well-known logos. So they are what you would consider a good…”

“There are no new industries, generally speaking. You can, you can debate on the AI space, but generally speaking, there's not new industries. There's just new versions of the same industry, and Century was in that.”

“There's, there's a few outliers that are famously bootstrapped and get pretty successful. And then there's everybody else that never gets that far because they get crushed by venture companies.”

“I'm like, I know you want the thing now, And this is your like objection to it. And I'm like, I think I agree with that objection. So I'm going to go remove that objection. And that, that to me is like, definitionally how you get a product market fit. And I actually think like, if I were to try to like reverse engineer…”

“the companies are driven by the founders and sort of key executives, but generally it's, it's driven by one or two people. And so if you don't sort of intervene in all these decisions, whether people like it or not, like the micromanagement kind of thing, you actually have to steer all those decisions and you have to…”

“I am now fully convinced that sales definitely increases our ACV, but is not the most efficient thing in a business like ours, or cannot be run, at least in a traditional way.”

“They'll be like, ah, well, the reason we don't have more customers is because of marketing. I'm like, no, you just don't have more customers because it's not good. It's not useful. Not, and, and it, it could never be useful or it's just not useful yet.”

“at the very least, when it comes to hiring, it is the absolute right advice. Trust your gut on if the person knows Or is aligned or whatever. Cause every single time it seems skeptical. Like to me, it's like, it's been wrong. It's been a bad hire and you have to unwind it.”

“I kind of believe like the way you build distribution is like brand is like really, really important. And most technology companies do not invest in brand.”

“one thing I see people do is they grow over time, they grow their business, become enterprise companies, and then they forget about what got them there. They forget about the long tail customer, the SMB or the mid market or something. And so many people do this because enterprise dollars add up, like, right? That's…”

“made me realize that the advice on like starting a company and not thinking about the business model too much is, is not good. Like I think you should think about it a little bit. It's like, what is, what kind of business are you in? Like what, who is going to pay for it? And like, are they going to pay for it?”

“What I could see a lot of tools, and this generally I think goes for enterprise tools, they are optimized around the buyer, because that's how they get bought. You, you don't, the users don't go buy the tools. The, like the actual end users don't go buy the tools. Someone in the procurement, IT, the leadership, someone…”

“Like, you could build a very simple version of something, but in this category, it's, like, just doesn't work because people already have, like, pretty high standards or high needs for how this kind of tool should work.”

“I don't believe that you can build the optimal tool for anything if it's very flexible and endlessly customizable.”

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

“trade-offs like speed versus quality, you know, like people talk about that and throw that around, like, You probably have room or I had room to be faster and to produce better quality without starting to trade off on either. That in most situations, there's so much slack that until you get to the fringes, yes, there's…”

“there was so much of communication that operators and founders do on a day to day basis where public speaking is actually a terrible mental model. If you think about it with public speaking, it's one directional. You're sage on stage. You have one speech which you perfect, your TEDx talk, where like every hand gesture…”

“I actually think, uh, a very fine motivation is just a desire to build a company. I actually think some of the best companies out there is just like a desire of any company and just in relentless desire to build that.”

“and then I think sometimes if you just keep on iterating with MVPs, you just end up with this Frankenstein of a product.”

“One of my core beliefs now is that you pretty much have to do a bit of like founder engaged, like almost at all scales, you will, the founder will never be fully disconnected from sales because like understanding the, it's no longer like, here's the simple thing that solves this problem anymore. You always have to…”

“That I think is why it becomes difficult for them to become this trusted confidant, because you're never going to move fast enough to actually seize on an opportunity they have. Like, If a customer has a burning problem, they're not going to wait a quarter for you to go and, like, roadmap and plan this out for them.”

“I think for competitors, it's absolutely one of those things in which they're the ones who are the closest to your problem as well, and you should absolutely be looking at what prior art is, or, you know, the state of art on their end.”

“engineering used to be a scarce resource. I don't think that's the case anymore. Not to mention, I mean, AI is making everyone be even more capable than ever.”

“execution has become more important than ever. And it's not so much about like idea discovery or like untapped market discovery anymore. It's just a question of pick your poison on how difficult, you know, it will be. But I think every space now is really challenging.”

“Our Insight here was that these documents were made for humans like you and I to read. Every little visual cue, like a gap between two paragraphs, that's me telling you, hey, this is a new semantic piece of information, or a tab structure in a list is me telling you, hey, this is a sub idea of that parent idea. And so…”

“We had gotten this advice of you should launch early. You need to like get this out there. Don't be afraid of failing with your launch. But we knew that we were In a space that if we launched too early and the product wasn't good, it would sort of be a waste of everyone's time, right? People already had PDF processing…”

“I would upload a hard PDF into AI applications, and I would show them that their application is hallucinating. It would be a very clear, like, here's the document that I sent in, and your model is actually making up information that wasn't there. And for any product team that cares about that sort of accuracy, that's…”

“it is very valuable for us to Not deal exclusively with healthcare customers and not deal exclusively in insurance or finance or any given use case because the learnings that we have from each type really transfer across them, and they've made the product into what it is today.”

“I think over time you need to have a single leader. You can't have three leaders for a decade, since you can't. I think that'd be very difficult.”

“if you've got a great vision, a great North Star, But you don't, you don't know exactly where that trajectory is going to bring you. You need that flexibility because otherwise what you're thinking today might be useful in five years may not be useful in five years. The next five years are going to bring us tremendous…”

“There's a intent-related reason why social media never works for local businesses, which is that when people are browsing Instagram or Facebook or TikTok, they aren't browsing with an intent to buy dog-earning services or Now that we serve restaurants to buy restaurant food, they're there to be entertained ultimately.…”

“I think most people would assume that the utilitarian part of sales, sales, sales is 90 plus percent of the equation of whether they continue to retain and use the product, but I would argue that it's at least 50% emotional, if not more, and 50% sales oriented.”

“I, on the skill set dimensions, don't assess those in an interview. I assess those via references, which I do a huge amount of references on any key hire.”

“There's a reason why all product led products are close to free because they don't have the level of perceived value or trust on the front end that commands a high price point.”

“Reason number one why it's bad, but like reason number two why it's bad is because everyone looks at that bad hire or that bad fit, basically. Again, like, I don't think they're generally bad people, but like that person who isn't a good fit, and they look at the leader who hired that person, either the founder or the…”

“I, I do also think it's true that at some point, I don't know, companies get big enough that you have folks who, who maybe are just not, Up for that, and like, you just have to kind of be okay with that if you want to have that many employees in your company.”

“My main view on reference is that I actually don't think they're that useful unless you can find someone who has more incentive to tell you the truth than to, like, have the back of the person they're giving the reference on and someone who really understands you and your company.”

“No, I think it's easier to see when someone isn't good at their job.”

“And then step three is, you know, let's say they kind of get past that is, okay, now get in buy-in from the rest of the team. That shouldn't be a, like, a decision-making forum. That's more of a, hey, I want you guys to, like, meet this person and get a sense of who they are. But that's not a, like, you get to veto…”

“I don't, I don't think any important decisions like this can be made by committee. Like they should, I mean, they should use input from all the folks who, you know, were part of the interview process, but ultimately the, the founder has to decide or the hiring manager.”

“I think you're way more likely to be successful when someone is stretching up into the role because they're going to have a chip on their shoulder. And like, you really want them to prove themselves or they want to prove themselves.”

“it feels like you're doing a lot as a new leader because you're doing this big reorg and everyone's talking about it, but Like rarely is that really the answer to solving your problems.”

“Assess the talent pool pretty quickly. Like, just fire the people that aren't good. Especially if they're not a good culture fit, but also if they're just not doing well. One thing I have experienced myself, but also I've, like, seen with other leaders, like, you come in and you do your, like, I don't know, your…”

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

“Per your point, if the, if you just have to assume that the distribution of failures is, like, pretty much the same across the org, I think it's always a pretty good sign if people have fired a lot. It's only because, like, they're gonna have to in whatever job they're taking on. If they don't have that experience,…”

“we needed to make sure that our go to market was targeted at the people that appreciated our differentiators enough that they were willing to ignore the things that we were missing that were table stakes.”

“And even I would say up through maybe two million to five million ARR, I think that thinking too much about competition is generally distracting for two reasons. One is that you don't really know the identity of your company and also you don't know You are not seeing enough of the deals in the market. You're not seeing…”

“when you're not doing seat-based, you're doing a value-based sale, and you are pricing in this usage way, you can, you can price more aggressively. And that probably enables you to go way higher over time as you generate more value. In a way that most seat-based pricing models don't enable as much.”

“It's heavily weighted to work trials and take homes. We like give them a chance to focus on that. It's much harder, obviously, to do a behavioral interview where you go in a methodical way through their background and, and kind of identify what they've accomplished and how that translates to the job. That's not really…”

“I think this is a thing that many people who build consulting companies, the thing that they get wrong is that they accept whatever work comes their way. I said no to anything that wasn't in those lanes. And that meant that we, not only did we get better at doing that work, but we also developed like internal IP.…”

“I think one of the things about product market fit is that people don't realize that you have to keep solving for it constantly. You, you have to solve for it at zero and at one and at 10 and at 50 and at a hundred and different parts of that journey for different companies feel hard and different parts feel easy.”

“I think that experience is just like extremely undervalued in startup culture. And I think that's a huge mistake. And one of the pieces of advice that I most frequently find myself giving to founders are people that are thinking about starting companies is like, go work at a company before starting your own. Because…”

“I think the best products come out of a little bit of, like, internal conflict around people standing up for a use case in a way that, like, is counterintuitive to the core product team. The core product team is so used to one way of thinking and, like, a set of users and has built years of intuition, and it can be…”

“I think a lot of the best zero to one product people Should be forced to get the first million dollars in revenue for the thing, not just build the widget and have the sales team bring it to market.”

“We start with people who are customers who just became customers for a couple of reasons. First of all, the purchase journey is still fresh in their heads, but also If they didn't buy, they might not actually be your good customer. They might not have bought because it's not the right product for them, and everything…”

“I don't care how much effort it is to do the experiment. I care if this works, how big can it be? Because a lot of times people will just work on a piece of the funnel or something that even if it did amazingly well, You know, it's only move the needle by three percent mathematically.”

“if you don't know how to grow the product yourself, you know, you're hiring someone else not to be your head of growth, but to like be your figure out how to grow this business person. And that's an extremely hard job. And most of the people who can actually do that are starting their own companies or, or working for…”

“You know, the instinct for some people, product people is we have some happy customers. We're not growing. Let's add the features the other customers want and hope if we add enough features that we'll grow. And that's usually, you know, not the problem. The problem at that point is probably go to market.”

“And there's one question we asked, which can very reliably weed out teams we don't want to work with. And it's the premortem question. Okay. Suppose we're two years out. And this didn't work, and you've completely failed and missed your goals. What probably went wrong? And their willingness to acknowledge that that's a…”

“So what seems like a very, you know, contrary to popular wisdom, make the boarding flow longer and ask lots and lots of questions actually really helped to build intent. And then by the time they get to the paywall, they had a surprisingly high conversion rate there.”

“Founders by definition need to develop an extremely high level of empathy and understanding for the needs of people across multiple personas. And also understand a baseline grasp on how markets evolve over time and what makes for something that's more durable and versatile. And I think being able to speak to founders,…”

“actually we fell into product market fit, not because of something we changed about our product, but because we were early to the market and we didn't die because we had figured out a way to kind of like operate the company profitably and not run out of capital.”

“Maybe you index a little higher on the extreme outcomes version. Like if your north star is wrong, your north star is wrong and you're really gonna stick yourself. But if you don't do that, you cap your upside really severely because your whole company becomes just designed by some consensus of people that don't…”

“Content marketing, buying ads, whole outbound, anything that lands a fresh new person that's never seen it before on our website to just sign up directly through our funnel would fail miserably because they'd show up, they would have no connections, and they would be in a single player mode environment with no single…”

“telling someone else how to run their very unique business, um, is incompatible with the idea that, um, their goal is to build, you know, a billion dollar enterprise by virtue of the fact that it's different from everything else. Those two ideas are incompatible.”

“Please don't take the egregious sacrifices to everything you value in your life by building an incrementally superior product in a big category. You will go All sorts of nowhere.”

“Their manifesto or principle or values around all of business, or around the core of business, and this is me, I'm not quoting them, this is just my observation, and they're right in this, is that people start businesses to serve their interests and desires. The company works for them. And somehow we forget that, and…”

“You know, you kind of take a look at The number of people who engage with a tweet or the number of people who land on a landing page, number of people who open an email. And I really think those are all bullshit metrics. And really what I've tried to do in the entirety of my career is really focus a lot more…”

“when you think like, oh, you need a different message for CFOs, a different message for IC engineers, I think that can actually kind of lead you astray when it comes to brand development. So that consistency is really key.”

“The first and foremost thing is that brand isn't owned by marketing. Like I would be lying if I said that. And I also think it's disingenuous and probably like detrimental to how you think about brand at a company if you think marketing owns it. Brand is a shared cloud between marketing, between comms and PR, between…”

“There's almost like this, this attribution that is imbued into your product by how much time and effort and initiative you place on your marketing... when you spend that extra time and craft increases the ability for you to reach audiences beyond that very core ICP that you care about. People take notice when people…”

“I think if you bring in highly specialized folks into a startup, it often doesn't work out because your diagnostic may yield a very different result three months from now than it does today.”

“what we found is that people tend to be much more Following the leader in the space. And so they would rather do something that another fintech company or another healthcare company is doing rather than thinking from first principles on, oh, we have a customer support use case. So even though we're in healthcare and,…”

“If you can get people into a room and close them well, what you need is more fire at the top of the funnel. Like you need a demand generation person who can bring in more awareness, more leads. More conversations into the funnel. If they're saying like, yeah, for the most part, like some people really get it, some…”

“don't set these dumb exercises that many founders do, which is just like, write me up a 30, 60, 90 day strategy plan. Like, Anyone with access to Google can come up with a fairly good document on that front. You want someone who can get very deep on your funnel.”

“The mistake people make the most is, you know, they'll be like, well, that's a cool idea, but it's really hard. Let's wait three years till it's easier. When it's easier, there'll be a million people doing it and there's path dependencies in there and stuff like that.”

“there's less of an emphasis on end user experience, I think in the enterprise space, because once you're kind of over the line where the CIO says, okay, that's on the checklist of things that your software does, anything above that doesn't really matter very much. The users will use it regardless.”

“Marketplaces are not really usually winning on the software itself. Only if the software helps you find more selection on the demand side or brings you more money on the supply side.”

“So then there's the example of, okay, you actually have an asset that can be leveraged for the marketplace. And generally the way those models win, whether it's, you know, Airbnb or like Hipcamp is a company that I spent a lot of time working with. You're asking that supplier to generally do very little at all to…”

“I think Toro has done better than GetAround if I've paid attention correctly. And part of the reason why is GetAround built a bunch of infrastructure to make it easy for hourly rentals. And Toro is, wait a minute, there's no money in that. We should optimize everything around daily. So at least their AOV is higher when…”

“marketplace businesses need to get sophisticated around data, usually a lot more quickly than other models. And part of the reason for that is Once you're doing more than one category or more than one city or neighborhood, the aggregate data doesn't really tell you anything anymore. The only trends that are interesting…”

“you don't sell to developers. You know what I mean? Like there's no selling to developers. You have to just show up in the right way.”

“Pricing and packaging is a art. You don't delegate that to an external agency, but you've got to have a sense of intuition of what the market bears, what the customer's thinking and doing the research. That's my one recommendation is think deeply about packaging. Forget pricing. Pricing can change. Packaging. How you…”

“one thing that's really clear about successful CEOs is that they don't ever really worry about the downside of their strengths. Like they just go almost blindly, just like at the business, applying their instincts.”

“everybody who starts a company is almost definitionally narcissistic and sort of believes that they are not subject to the statistics.”

“The third time you start the company, you're like, fuck that. Like that doesn't matter. What matters is I got to get the right product into the hands of the customer immediately. And I've got to test it in market and I've got to focus on sales and win rates. And I've got to drive the team super hard. And some people…”

“What if I look like an asshole is a fundamentally egomaniacal question. It's a terrible question to ask. The right question to ask is what's it going to take to win?”

“I find that executives need to deliberately oversteer in the direction they want, even to the point of it being a little crazy, but it's because they are the sole tension on the line of tighter constraints, higher bars, harder, you know, harder standards versus the army of folks who are inadvertently, not in any…”

“Like, the vast majority of executive decisions are coin tosses.”

“Hiring managers should not ask someone else who they should hire. They should simply ask for objective inputs to the decision, and then they can make the decision themselves.”

“I think they're fucking filled with happiness and enjoyment and energy and also tortured by the fear of failure and by whatever demons drive them or whatever passion drives them. Like there's this awesome Jekyll and Hyde yin yang You know, dynamic to what it's like.”

“Clear thinkers don't have to be that smart. They just have to be experienced, or they have to have lots of at-bats on a given topic until they've rounded out their understanding of a system. They might not understand why something is the way it is, but they darn well know what it is.”

“Oh my God, yes, you can have too many first principles thinkers because they have a tendency to over-engineer things. Not so much about having too many first principles thinkers as it is having too many people doing first principles thought. There's only so many times you have to solve a problem. There's only so many…”

“I'm just gonna call fintech one-oh kind of what happened in the last 10 years. It was very much single player games. It made it very hard for fintech companies to authentically design products that had distribution built in that would lead to other people because people don't really share their bank accounts. You don't…”

“the attributes that tend to select for founders who end up building the scale businesses tend to select against people in some ways that scale particularly well in different dimensions. And one of the ways they don't scale well is, is quite that posture on how they handle decision making or the belief of they're the…”

“And in tech, we just keep going back to like, well, you got to bring the founder back. There are a lot of incredible attributes to founders. That is not a solution that scales fundamentally.”

“I end up in this seventy-twenty-ten kind of place where I say, look, spend most of your time on metrics movers. Carve out at least 20% of your time for customer requests. But 10%, five, 10%, you have a list of these delight features. Go do it.”

“I'll tell you about unit economics when we get to round B or C right now. I want to improve product market fit, right? So the idea was like, keep it very lean, almost no sophisticated stuff, but make sure you get those precious sales conversation in front of the right people.”

“I think early stage, I would not worry about payment as a key thing.”

“Building to call it like outcome to make sure it provides the outcome is any way easier. You work with the design partner, you build it together, you see that you get the outcome. Building to make sure you can actually compete successfully, win 50, 60, 70, 80% of deals is much harder because over time you find out what…”

“I think superhumans at 40% is a threshold of some sort. I think ours were like 80 maybe. It was nice, but I think it was, I think we over read into this because I think you asked the question of people who actually use this piece of the product. So you very early see that there is a product market fit to Um, certain…”

“I don't think you can be fully intellectually honest if you're talking to the person. How we're sitting, the tone of our voice, what we're wearing, all these things have influence. It's the only way you can be truly intellectually honest if you have absolutely no connection with that person. They pick the thing up Of…”

“I think, you know, the, the deals around POCs and innovation and, you know, sort of, I call it funny money. You don't really want that stuff, actually. I think that is a distraction, because it's easy to cut. Your team will have spent a lot of time, and it'll be for naught.”

“And I think it is just so much easier in mid-market and SMB from a functionality perspective to just switch, right, to something else, especially in generative AI where it'll be confusing for a while. It's gonna be hard to scale a big business if your buyers are constantly, right, shifting focus, shifting attention.”

“In my opinion, training models, especially smaller models, is easier than figuring out how to leverage the large language model capabilities correctly.”

“Somebody with good judgment seven times out of 10 will probably pick up on the right answer with less data.”

“In later stages, you can start to look at other metrics like NPS, CSAT, time to launch, and your implementation. Those, uh, can be great metrics. Those sometimes can be, you know, easily gamed, so they don't necessarily provide the right insight for leadership or, or even in individual CSMs on what actions they should…”

“if renewals are primarily just that, a renewal conversation, where there's a quick, you know, exchange of papers, a quick conversation, if there's a change in price, but there isn't a detailed negotiation or any complexity with that transaction, that renewal process should at minimum sit under the CS leader. It can…”

“I am a big fan of, say, the CS organization reporting right into the CEO, because in those cases, the CEO is really close to the customer experience, no matter what phase the business is in, super early or operating at scale.”

“The thing that I think companies get tripped up by is when you put a significant amount of comp against a renewals or expansion quota, that is going to drive behavior. And if you want your teams only focused on getting the renewal across the line, that is where they will focus. If instead it's really important that…”

“The problem with that is CSM Brett does an implementation and onboarding process once, maybe twice a year. Because that's how many net new customers you get in your portfolio. Versus if you have a group of implementation specialists, they do it all day, every day, and they get really efficient, and they feed…”

“I think there's literally founders who think cool, but it's going to kind of Contract out the engineering or kind of bring in some, some con, you know, an upside firm to do this. This is a hugely horrible, bad idea. If you're trying to build software as to not, and I'm super biased, obviously engineering leader type…”

“I got an engineer. He's amazing. And I got a designer and he's amazing. We don't really need product people. Like who are these folks? We know what we should do here. That's also a disaster. So like, I'm just picking one of the many sort of. Initial conditions that like lead to a successful product and just even…”

“You need those Stuart Butterfields. You need those Dr. Carps and those sorts of folks, but you also need like that set of folks that are just like turning the crank, building the crank and turning the crank. These are incredibly important. By the way, not sexy work. It's not sexy work at all. It's like process stuff,…”

“There is no accounting. Because it's, the moment we do that, then the project managers show up and they say, cool, have you done your wolf time? Great. Check. Let's do that. Thanks so much. Great. Good job, everyone. Now we're operationally sound. It's the shower time. It's that time for something to be created. And…”

“the bad ones create a scenario where engineering doesn't feel like they have a vote in what gets built. And the, this 29% time that we're talking about here is one of my countermeasures to that, in that an engineering culture where they don't feel they can invent things is a super bad engineering culture.”

“Consumery software, which means you're building a software for regular humans. I would argue you have equal parts engineering, design, and product. Products there to tell the story of the customer and to, to influence, like, to think like the customer, to think simply like the customer and not be encumbered by the how…”

“every leader that you just referred to, every single one, when I'm right, and they're wrong, and I can convince them of that in whatever scenario, they understand that. They go, yeah, well, yeah, shut up. You're right. Stop. I got it. I got it.”

“I think a lot of people want to be told what to do. Oh, I just threw up in my mouth. And I don't, I bet these people don't even think that, but I think, I think it gets you started. Right? It's not, you're actually not going to do it. I'm gonna say, hey, go do this thing right now. This is how you make coffee. You…”

“I think you can learn from background. Checks, but there are people that are, they're picking the people that they're telling to you. You gotta do like unsolicited ones are actually the ones that are actually interesting because someone who hates them tells you really interesting things, both positive and negative.”

“Accountability, if you ask most people what accountability means, they say, well, it means if I don't do what I said I was going to do, I'm going to be in trouble. It's not what accountability means at all. Accountability means to give account, to give the story of why we did this thing. Account. It's literally in the…”

“You're not, you get a new role. You're not good at it for three years.”

“30% of the people always going to hate you. It doesn't matter what you say. You're always going to be pissing off like minimum of 30%, like all the time.”

“you must stay technical as an engineer. They can tell. They know when you're no longer doing that, and your credibility, it's not gone, it's just different.”

“And by focusing it on this one task, I actually feel like we have more of an ability to innovate, uh, than if we stayed more broad. Just because, you know, like having the boundaries allows you To actually push against them in ways that I think are productive.”

“we quickly realized that everybody needs outbound and not everybody needs inbound. So actually outbound is a better and faster starting point.”

“I really think that when the need is large enough, people We'll buy your product and wait for you to build the rest of the features. And that, that is actually the main indicator that you have something worthwhile.”

“once we agree to something and it's on our sprint planning, nothing will shift it. If you're walking to work and you happen to have a new idea, throw it away. We're not like the, there's only one moment to think of things and that's during our planning. And then we commit to it and we do that. Unless the data changes,…”

“not put so much pressure on the product and strategy that I think leads you to something that's less interesting, actually. Um, because, you know, you don't have enough information. You're kind of a priori trying to make it as big as possible.”

“There are kind of like some certain natural numbers of retention. At different stages of the company, depending on who you're targeting and for different types of companies. And so don't try to kind of improve something, let's say by 50%, that's already okay. Take the thing that's doing well and push more gas on it.”

“You're coming in and the first 30 to 60 days is observing, talking to customers, talking to the people that are building this product, that are marketing this product. That are designing this product and really understanding how does this business tick? What's working and starting to make, you know, some opinions on…”

“Sales motion experience is probably more relevant than domain experience.”

“Dropbox is a really interesting case study, and it is one that I think too many people look to emulate, but they just can't. Because what happened with Dropbox, amazing product, perfect market timing.”

“And I would say maybe five percent of your enterprise customers are able to actually leverage that access to IT's interest and security to drive a bigger deployment.”

“the job is realistically is 70% CS, 30% sales.”

“we look at every single category that's been created, it's very noisy in the beginning, but there's a period of like, there's like a two to three year window, where there's a massive competition, but coming out of that, the category leader is kinged or queened, and that category leader gets like 70, 80% of the market…”

“For PLG companies moving to enterprise, what we found was one, and kudos to my team for figuring this out, I didn't coin this, my team did. First, we call them, we call them Intel agents... The next level we call them or change agents... And so those are change agents, and those are really, really important, because…”

“the edge that they had was eventually the route to the CIO, the CTO to then just, all right, let's just Deploy this across the whole organization. That path is very short. Whereas for many PLG companies like us on the distance was really long.”

“So there's another model where the founder goes into, well, I was a genius in the first one. Therefore, I don't need to do all this stuff again. It was obviously my insight when in fact, What they didn't realize it was their customer insight that they had been learning from, thought they didn't need that anymore, said…”

“You want irrational people. And if you're not going to be irrational, You ought to consider you're competing with irrational people.”

“It created essentially modern entrepreneurship where it says there are no facts inside the building. So get the hell outside. And the other version of this is there's no way you could be smarter than the collective intelligence of your potential customers as smart as you are.”

“sales was just a whole different, you know, dynamic. It was The most difficult one to solve for because in the early days, you know, if you're offering a software product, you have the traditional salespeople who are used to selling a subscription-based software product, but selling a SaaS product on a…”

“The way that you start solving math and some logic-oriented problems is under the hood implicitly ask the model to write and execute code.”

“And our approach to it is, we're not, quote unquote, solving hallucination. We're solving Unintended hallucination, which would be something like, what's the distance between point A and point B? Or what's one plus one? Like, that should always be two.”

“Chief architects and CTOs are pretty inefficient in terms of Actually getting enough context in their heads to make a good decision on any given, given point.”

“And then committees, like in almost every architecture group turns into a committee where they have to balance their, their different perspectives, or they're just like slow and kind of inelegant. It's rarely true that a committee gets the best decision.”

“Salespeople are not fungible, replaceable individuals. They're, they're like uniquely talented people.”

“You can be ideologically like pure and say we shouldn't measure something, but all it does is slow down the learning of the organization around you. Doesn't actually help you accomplish your goal.”

“in cases where there is no clear path forward or where the folks who have the context around the path forward are like violently in disagreement, it pays to get into the details and make the decision yourself.”