The Wisdom Wall

“the whole work life balancing is BS. Like if you're building something, there's no work life balance. And the reason why that is, is I think you have to go through a lot of cycles. And so the more like, if you work more, you go through more cycles, fail more, you fix more. And so if you, if you, you can work seven days…”

“I'm a very firm believer, and I actually took that from back then, and it's still true today, that you will only understand the problems that you could solve and the potential solutions if you're there. Everyone in product says that you have to speak to your customers, and I say that's bullshit. Speaking to your…”

“I think you should not collect revenue and not onboard customers until you know that you are going to get a million of revenue as quickly as possible.”

“So why not give away product and not try to focus on product market fit and give it away for free and get them to pay for something that is more valuable. Or something which has a bigger, forget valuable, something that has a bigger market. You now have all these leads of businesses that are using payroll software, a…”

“I think it's easier to build an average product, give it away for free, collect a lot of leads and sell them into something else where people in that space also pay for. And then now you got a cheaper flywheel than spending money on Google ads or trying to do SEO or social media marketing or anything like that.”

“Like, I think one of the biggest benefits of going so viral is now you don't really have to talk to users as much because you can sort of see user data and the quicker you get to see user data, like I'd rather see 70,000 user data points rather than talk to seven users. Um, and I think this is, it allows you to iterate…”

“to be in the mind of the audience, you must be in the eyes of the audience. And that means necessarily go viral and go viral necessarily means be controversial.”

“It's almost like, you know, they tell you, they tell you shouldn't be working in the business. You should be working on the business. And I'm like, no, you should be working in the business as long as humanly possible. You should do whatever's the hardest thing to do that you're best at. That's probably the thing you…”

“to run a tech company, like really coding is a very small part of what you're doing. And it is in some ways a commodity.”

“what we found is like again and again, you want to talk to roughly 30 people to like validate an idea or invalidate an idea. 10 is not enough, because you can always find 10 friendlies or 10 unfriendlies. 50 or a hundred is too difficult, too many, right? But you can easily have 30 conversations in a couple of weeks.…”

“you truly find the, like, core of the product market fit once you sell hundred customers. It doesn't mean, you know, that it's, like, everybody's super happy and everybody's, like, at a, at a huge, you know, deal size. But, like, again, like, around hundred, like, you actually have hundred goes at it. And then the…”

“I think the qualitative stage of product market fit happens only very, very early. Right. Like that, like you launch it in an event and everybody wants to talk about it. It gives you conviction to take the next steps. But once you become a little bit bigger, once you launch more product and so on, then it becomes like…”

“healthcare is highly consolidated. CVS, Cigna, and United Healthcare. Three publicly traded companies, all of which are I'm gonna say Fortune eight, Fortune 10, Fortune 14, respectively, in that range. And so when you're battling with titans, yeah, ten million ARR is okay, but it's nowhere near the scale to, one,…”

“Can't ask. You just avoid it. They have to bring it up. And if they bring it up, and the other and to this logic string is, and they shared something personal. Like, I have witnessed how bad healthcare is. Let me tell you why. Odds are, this is personal. They want to fix it. They don't want anyone to experience what…”

“If you're not getting response rates, I think it's probably a good indication that like there's a product market fit Issue at some level, but like, you gotta be able to describe what you're doing also.”

“I think that's the part where a lot of people are kind of confusing between product market fit of a product you currently have. Or that you have a great team that can execute very fast and be agile, and you build something else that that might fit whatever the PLC wants.”

“So I think we build the product from an architectural standpoint a lot different, where when complexity increases, it's not that we increase the prompt size. We increase the number of components of AI components of LLMs. That we use. So essentially when complexity increases, we increase compute and we build things…”

“Winning an enterprise contract is the easiest part of working with an enterprise.”

“You want to build something where there's a budget for it right now, or you're very confident that there's going to be a budget for it in next six to 12 months. The thing is, you know, those kind of tech waves, if they haven't started yet, they might start tomorrow or in five years.”

“I don't think competition is what kills startups at our stages, right? It's competition makes you do stupid things like copy other players or go toward the second, a different direction.”

“When people, when enterprise tells you, Hey, you need, you need more logos. The reason is probably different. Okay. Now the more logos you have, the easier it is because you have credibility. Uh, so they'll start by thinking that you probably have something to offer them, but if you don't, it's just about really…”

“Ideas are trivially easy. We have a thousand ideas a year that many of them just don't even get code names. Ideas are not the hard part. Our alpha comes from how efficiently we can discover which ideas are valuable.”

“In this extreme situation, we can see that if you built the pedestal, you're half done, but you're really zero percent done at burning down the risk. [1649] Pablo Srugo: That's right. [1650] Astro Teller: The point of a testable hypothesis, especially at X, everyone at X will just say as shorthand to each other,…”

“finding some little thing that people will buy, which in some sense is a product market fit actually doesn't have a very good chance of changing the system. If our real goal is to fix the system, then we have to figure out a much more complex set of things.”

“And I worry that there's a bunch of product market fit that is so siloed. It's just building a ladder to the moon. You might build a pretty tall ladder, but you're not going to get to the moon.”

“You can make a billion dollars a year selling to incumbents, but you're probably not going to change some huge industry if the incumbents who are your main customers don't want the industry to change.”

“I've heard of pilots where you get something and they have AI, but then they have humans that go and correct things that AI got wrong, and then they give you the final thing. And it's like, well, that's not really the AI part. You should be upfront about that if you're doing that. I've seen others that will go through…”

“Also, like, one thing that I deeply believe in is that a seven, like a seven out of 10, is actually one of the most dangerous hires you can make because this person will have enough redeeming qualities to shine And we will be very slow about letting them go. Maybe we won't. And over time, they will shift the, like,…”

“As soon as you see that end state being 10 to fifteen million of revenue, not five hundred million or a billion of run rate, then now it's opportunity cost. Now we're wasting everybody's time. We're wasting our time. We're selling a story to the world. We're sharing a story to the world that we no longer believe in.”

“getting to a billion dollars, you're investing in this kind of Series A, it doesn't even come close to returning the fund. You know, unicorns are not the vibe anymore. It's Decacorns Plus.”

“If I, as a VC, make an intro to another VC, the first question they're going to ask me is, are you investing? And if I say no, I've just deflated that balloon completely. So the last person that you want to intro you to other VCs Is a VC.”

“We kind of go against the grain, I guess, as it relates to running a playbook and doing just discovery and making sure that you're deeply embedded on that first call. What we find often is that we have to demo on that first call, and really just so that it conceptualizes what we do in AI and the impact to the customer.…”

“These business owners don't have pain. They have hope. Uh, and I know that sounds weird, right? Like you want to be with hopeful people. Yes. But where you build a great business is by figuring out where, when you press, does it hurt?”

“I think that time or that phase of products probably is gone right now because now you have to find your relevancy every day. You know, you're like one deployment of open AI or like one anthropic release away from dying. So you cannot sit back at the laurels of, hey, I achieved product, market fit, I'm going to scale.”

“I think hard problems are what, especially in today's world where anybody can build anything that we've got to solve the hard stuff first and then come down.”

“Similar to, like, the shift from SaaS to AI, you know, that is one of the key fundamental things that's going to challenge any incumbent SaaS company today. Systems of record moved to systems of engagement, like Sixth Sense, and now are moving to systems of agents and autonomy and, and doing the thing for me and taking…”

“the way that this VCs would open up to Amanda AI versus open up to me. They would be much more transparent. I could tell right away from a few turns of interactions whether they're going to invest or whether they'd be interested.”

“And realistically, no investment banker or auditor will sign your books and take you public if you cannot close your books in five to six days.”

“usually you can swipe credit card inside companies for two to 3000 dollars, but above that you need a purchase order. If a purchase order has to go through, you need permission from IT, you need permission from legal, you need permission from the bosses, the CFOs, and whoever. And for me, while that was friction, but…”

“the biggest problem, in my view, of startups is not a product that fails, because most startups can fix a product. It's the irrelevance. You have sold someone, that product is sort of, it's sitting in the side, no one gives a shit.”

“all the conventional wisdom of, like, build an MVP, start really small. Like, none of that makes sense anymore when we can all build so quickly now with Gen AI. It's more of a race. Who can actually build something useful the fastest as opposed to like starting really small, right?”

“I do not believe that you can start as a point solution and eventually take it all over. You need to be the full source of truth for day one.”

“the value of open source isn't just in the fact that it is free and that you have a community, et cetera. It's just that it gives you full control over your, one of your most precious assets.”

“moving these barriers was, I think, a very smart decision, and retrospectively, I would do it even before. That every pivot that I'm doing, everything in order to find and to optimize the time To find the mistakes, and to realize that you are in the wrong direction also, to move all the barriers, price, process,…”

“if you've got a design partner that you're speaking to once a week, you're almost certainly gonna fail, right? If you've got a design partner that you are working from their office, and ideally sat next to them, you're almost certainly going to succeed.”

“our risk is, as I mentioned just then, is like, we may not have product market fit tomorrow morning. And that's not based on, like, OpenAI or Anthropical. It's just based on the speed that Verticalize application is shipping great products. So really, our only risk now is the speed at which we can ship products. That…”

“Top of funnel discovery is not for trade shows. It should be mid funnel.”

“There was this viral thread about how Twitter or how Cursor doesn't have PMs. And I think Linear also said something similar. And people are like, yeah, we should have PMs. And That actually makes sense, but you have to really think about for whom it makes sense for. It makes sense when the builders are the users,…”

“All the models just constantly get better and a new entrant coming in today can probably out of the box, have a product that is equally as good as yours. And so your time in market mode, frankly, doesn't exist.”

“Instead of what he chose to do it is no, no, no, I'm just going to become an MSP, but I'm going to become an AI first, highly scalable MSP. I won't have the same margins as if I was purely selling AI, but the speed of go to market is going to be orders and orders of magnitude faster.”

“Literally, unless you're walking around and looking over everybody's shoulder the whole time, like, doing what I did, like, at scale, like, you don't know. You have no way of knowing. And so, these people try to drive transformation, you know, back when I was in consulting with all the digital transformation, it was…”

“Pre-gen AI, the biggest thing was as a seed stage investor, is this real value creation? Like, is this a nice to have versus a must have? That was the big question for most companies that came to pitch... These days, the reality is AI has put founders in a place where there are so many places to add insane value, no…”

“One, these organizations as a whole are staffing agencies. They are primarily driven by the revenue and cost plus model they can associate with their staff, with their human capital. So they were not going to be interested in deploying technology, and they weren't going to maintain the SLAs that we wanted to provide…”

“each video on Instagram or TikTok averages about a thousand views, everything, you know, regular, regular account. So the math is you do a thousand videos On a thousand, it has a thousand views, and you will guarantee a million.”

“in certain businesses, it's not product market fit. It's product price market fit, right? Your product could be fitting, but the way you price it may not create the fit. And so you have to deeply think about, am I pricing it to really enhance my product market fit?”

“So far, the attempts have been, hey, there's a problem, it's well recognized, logistics is highly fragmented, It runs on emails, phone calls, and text. We're going to solve it. But the way we were going to solve it is we're going to build a new system. And because it's so fragmented, you just cannot have everybody join…”

“So, okay, you might give up three orders of magnitude in write latency, but actually you don't have to give anything else up. And then you have this true two orders of magnitude decrease in the base cost of the system. That's a great compromise if you're building search.”

“When you train an AI model, you're trying to basically compress all of human knowledge into a few terabytes. That's impossible. You can't do that. At least not by any computer science or any science really known. It does not make sense that you can compress all of human knowledge into a few terabytes. What you can…”

“if you want to get developers to use a security product, you have to build a developer tooling company not a security company.”

“the kind of worst case scenario is not to get to crash and burn with your company, but to get stuck, to get to a company that it's at two million RR, three million RR, growing 30% year on year. It's kind of enough that you don't really want to just cut loose and go. But not what you signed up for.”

“If you're going to ask for something, ask for something at a size or scale that's meaningful for your potential customer. Because if they cannot do it at a scale that's of meaning where their boss has to sign off on it, they might not be that serious.”

“you only have two real advantages. One, you can really cater the initial set of value of the product to what they want because you're building it as you're talking to them, right? So you can do the things that they always wanted to get and nobody else would give them. So you really have to create this very, very close…”

“my job is to understand this industry, like the market, the future of the market, where it's going, like see around corners, do all those different things. Like that's my job. And my job is to be the best in the world at that. Their job Is to be the best in the world of taking ideas like this one and creating value…”

“It's not the developer tools market anymore. Like it's the market for automating the production of software, which is something closer to like the market for like paying software developers to develop software. It's like in between the developer tools market and that, which is more like a trillion dollar market.”

“There have been some situations where we've talked to companies where they're like, no, like our founder believes in like we build this in house and we can be uniquely good at it. And obviously I'm biased, but that is just fundamentally not true. There's no one who is that much better at like their cloud provider. Like…”

“It's a great thesis if you're in Chad, or if you're in Syria. It's a horrible thesis if you're in New York City or San Francisco.”

“if, if you never touch the code and just rely on agents at some point, you're not going to be able to go forward unless you're a professional engineer who can unblock the agents and then, then, then kind of direct them in the right way.”

“the dilution, uh, for a given venture backed company has more to do with the needs of the investors. And it has the needs of the founders. And so founders are, you know, don't get screwed by a bad deal, but realize that the numbers that you're coming to with in negotiation with your investors are driven at least as…”

“So you might bridge a company. For the express reason of having better marks to go and show your LPs when you go and fundraise. And so that might be the primary reason you did it. Even if you're like, I know this founders and probably don't get there.”

“free users are often, like, not, they're often negative signal, in my opinion. People, the people who are willing to pay for software are sometimes a totally different group than the people who are willing to use it for free.”

“attacking their core job was not that exciting for them, but getting rid of the tangential bits of their job that were irritating, that was in a bit that was kind of forgotten by the other legal tech players was an excellent wedge.”

“I was quite insistent about not doing it for free because I felt like the process of getting an order form in place and making people pay you money was part of the pain. Um, and also part of us learning how to sell. And I think it was so easy to just give stuff away for free. And then also people waste your time…”

“if you're just out trying to hire, like, some random engineer or technical person that you have zero experience with or otherwise, um, I've seen some of the statistics around this. Your probability of, like, failure is, like, not just, like, two x higher. It's, like, a hundred plus x higher. Like, you almost, your…”

“the faster that your product can get to a million, the faster your product is likely easily replicatable.”

“it's actually unlikely thinking a long time about decision will actually dramatically improve outcomes. Um, especially for like very difficult, you know, like, um, uncertain decisions, actually like making a decision and then quickly reverting or like just learning from it is way more important than like the quality of…”

“People get, are super underpaid right now for their ability to, um, make viral content, and right now this delta has not been captured by anyone. Um, so when you hit someone up and say, hey, are you interested in a paid content opportunity, and they're regularly making content, almost every single one of them will say…”

“the opportunities in short-form content are much bigger than you think. Um, I think in our generation, there are two very big opportunities, and only one of them has been fully realized, one being AI, which obviously every tech entrepreneur is on, and the other being short-form content. The ability to snap your…”

“a startup capitalist is a different type of capitalist that they don't They don't create value through persistent compounding or competitive moats. They create value by changing the subject. And, uh, they, they break the pattern of how people do things. And only by doing that, do they change the future. And only by…”

“When you're a startup, the only advantage you have is your ability to change the subject. And so you want to, you want to have something that disorients the incumbents that turns, you know, Airbnb, they didn't try to have a better hotel. They turned the strengths of hotels into their biggest weaknesses.”

“in my view, the only way to really fail as a founder is to lose your time. And it's to, you know, be three years in on an idea that you now realize wasn't good enough, wasn't worthy of your time.”

“So let's figure out what the biggest risk is and let's raise the minimum amount of money we can raise to take out that risk as soon as possible. If we can't take out that risk, we're not going to succeed, but at least we get our time back. If we take out that risk, we've done the single most important thing we could do…”

“validated learning about customers, if it's truly valid, should allow you to go from one to ten million in two years or less.”

“it's not first mover advantage. Uh, it's first to product market fit that wins regardless how much they raise. And, and if you can get to product market fit without much money, You're gonna win even if the other guy raises more.”

“So if you have product market fit, a salesperson should be able to pay for their entire burdened cost across the entire company. Because if you, if you have that, then you can hire new salespeople at will, because every incremental salesperson will be a breakeven new asset to the company.”

“A lot of, um, startups and a lot of companies within technology are looking for vitamins. Yeah, if you, like, operate within a TAM and, and a buyer base that is always looking to improve and is, like, searching for solutions to problems they have, you're gonna do well by operating with, operating within it and building…”

“one of the hardest parts is making sure you always have your kind of sponsor inside the big organization, because until you have it, I feel like things are slow, but they go on. As soon as that person leaves, moves, goes to some other job, then you're, you have nobody who's going to follow you.”

“It's still pretty rare in the security and network infrastructure space, because very rarely do you get a good PLG motion working in like security for the simple reason that like no person wants security. Voluntarily, right? Most of the time, security is something that's imposed on you that slows down your work, and so…”

“it's not that seed strapping is a bad way to build a business. It's actually a fantastic way to build a business. It's a bad way to get venture returns. And that is the fundamental mismatch between the investor expectations and the founder expectations that I think we're kind of working through right now.”

“The acquirer was looking at sort of, you know, the inventory and the store as the asset, and sometimes the owner as the liability, when it's actually completely flipped. This same owner, you know, after selling their sort of water bottle brand, would go out and start a yoga mat company, and that would also be…”

“And when you stop hiring, you have higher output because all of your time, like every employee is in the J curve, they actually take time before they start being productive.”

“There are a few great lies of entrepreneurship, and one of them is that you can't grow a big company without raising a bunch of money. And it's perpetuated by an industry that, like, you know, venture capitalists make money when they give you money.”

“We learned that not all plaque is bad. In fact, that some plaques are extremely dangerous for you and the strongest predictors of who will have a heart attack and others are actually Very stable and almost protected against, um, having a heart attack in the future.”

“I think like a 50% gross. That has enough expansion to still be positive is kind of fake. You know what I mean? Like, like, like low logo retention, but like an expansion dynamic, like that, that, that doesn't really, I mean, I think MailChimp probably had that, but also their TAM was, you know, a hundred million or…”

“if your startup is stuck at a couple million ARR, it's probably something radically different. That's going to get you to a true product market fit rather than just like incremental feature building, like trying to outdo your competitor or something like that.”

“The only thing you should be doing until you are getting referrals that you are not asking for many every week is talking to prospects or customers or writing code. If anyone is doing anything else, you are wasting your fucking time and money.”

“You need to be on the phones, learning, pitching, well past the first million.”

“If a VC doesn't allow you to take out secondaries in your company, run for the hills. That's a predatory VC.”

“product market fit is the thing that's going to give you the venture type growth, right? The truly exponential, hard to control growth that puts you on a path to like a hundred million plus in revenue. If you want to build like a five to ten million dollar business, you don't need like that level of true product market…”

“if we need to do this at what, what, if we need to do this at the, you know, hundred X scale of where we are today, we're going to have to build something very, very, very different. Separate, separates writes and reads, that multi, that has multi-tenancy sort of built in, that the, the storage is all Blob. You cannot…”

“in case of, of most companies, um, retention is pretty much a function of, uh, user case rather than product. It means that you may create like a perfect product with all like, uh, vessels and all engagement features and all gamifications better than Duolingo. But if you apply this product to user case without natural…”

“in most of cases, in 99% of cases, if you can't find product market speed, uh, let's say in two years, Then it's quite low chance that, uh, you would find it.”

“As soon as we put it behind the paywall and people had to pay 15 bucks a month, we saw usage like skyrocket, right? Like obviously conversion rate was lower, sign up rate was lower, but when people got it, they really valued it and they started to use it more.”

“people become a super plus member Typically for one reason and one reason only, and then we'll try and cross sell them to other products within the business, right? Uh, and this is a bit unintuitive. Like a lot of people think that, um, when I have a membership program, let me add more and more value to the membership,…”

“A lot of people rely solely on cross-sell, right? They say, hey, I have this product, uh, and I think that we're going to be able to cross-sell whatever, at 10% or 20% into this new product. And what I can tell you is that cross-sell is very, very, very hard to do. Uh, and it requires the two products to be very…”

“If you're good accustomed, take a choice. It's, and it's extreme either say no and don't do it and stick to your product. Or say yes, but charge masses, like multi-million, five million for the customization.”

“I actually tell founders today, implementation revenue is not money. It's not zero. It's worse than zero.”

“If you're the captain of a ship and it sails home victorious, it was the crew. If you sink it, see, It's you, the captain, but it's never the wind. It's never the wind. The wind is the wind, right? There's nothing you can do about the wind.”

“I think now Jason would kind of say is like, okay, you got six months left. What can you get done in the next four months that makes your company stronger that gives you highest probability of success to close in six months and focus a 150% of your energy on getting those, you know, five things done so that your…”

“We don't talk about the food waste angle anymore because it's to the market that we're serving, both grocers, both consumers, like, it doesn't dictate purchasing power, and it, from consumers, it doesn't drive sales and purchases, and it doesn't, from all, a lot of retailers have, like, sustainability goals and food…”

“as you're starting a company, especially in the early phases, there is an immense desire to benchmark yourself versus everyone else. And there's always going to be someone who's growing faster. He's in a hotter space. Who's like more popular than you are or what have you. But the most important thing that we found for…”

“the moment they introduced that, it's really hard to sell an AI bot on top, um, unless you're, like, very enterprise upmarket, where, like, the scale of support tickets you have is so massive that, like, like, they're optimizing for, like, a percentage point, right?”

“The, the one way that anyone can make money on sports betting is through the promotions, like the signup offers and the ongoing, like, you know, boosted odds, boosted prices or deposit matches. So if you're, if you're very disciplined and you're willing to grind it out for really not that large amount of the money over…”

“It was really good to have only raised one round because if we had raised at a higher valuation later on, there might be investors who say, Hey, we can't take that. You haven't returned enough.”

“work-life balance, at least in a startup, is a myth, and anyone that tells you that is just lying to you or hasn't achieved anything, and I, I like to think of it as work-life seasons or, and harmony”

“Like we don't need, you know, unicorn or bus. Like we just, we just don't need that. And if we own 10% of a business, 20% of a business that exits for two hundred million dollars, like we're doing really, really well.”

“I think everyone, it's very easy to sort of rationalize why you're going to fix a churn problem a year from now, um, and not do anything about it. You know, as much as like, as much as you'd like to think, like you could look at the data, you could look at the metrics and kind of understand, you know, where is there a…”

“The reality is if you don't have product market fit, the most important metrics are not Bookings and revenue. The most important metrics are, are you delighting your customer and all are your customers? Do they look the same? And do you have a high level of word of mouth and cross-referencing and case studies that…”

“listen, I, I've seen more companies, you know, choked by indigestion than starvation, right? They've just, you know, they try to define their business by their technology versus the markets they want to serve.”

“getting a single strategic investor is, is a risk. Hey, if they don't like you anymore, what does it say about what you're doing, having to maybe not solve it, but we have dozens. So basically if you can convince the whole industry, the whole very smart investors that work, uh, for like what we would be calling…”

“even though like the mantra in 2015, when we started the company, it was like, hackers only have to be right once. Defenders have to be right always. And I thought about that inverse and I was like, wait, hackers only have to be wrong once for a defender to succeed.”

“If you wake up in the morning in a panic, that's not normal. It's not standard. And you do not have to live like that. If it's like, and you've already berated, like one to five people out of fear of all those crazy ass things that, that happened during your organization or in the business. That is not normal, and if…”

“when I think about Koshier's value, like it's not, it's not in, you know, the, the weights of any particular model. In fact, we we've released our model weights for researchers as well. So if researchers want to use our model, like they can download the weights from hugging face. And I encourage people to do that to…”

“Over time, I started to hone in that it's probably around 40% saying they'd be very disappointed that, uh, would, would, um, make Yeah. We would essentially set that company up for success.”

“I think NPS is a, is a great, uh, survey as well, but I think it's more of an operational, it's like kind of an operations feedback. Like let's say I have a product that's a must have, but their customer service is terrible. Like the person yelled at me in customer service. I'm probably not going to recommend that…”

“that's a really typical mistake. I see a lot of companies make is that they, they AB test their messaging for maximum response, where ultimately if people are, are converting on something, the product's actually not good at doing or something that's not that important, you're, you're not converting the right people.”

“Best practices of having a double-sided referral incentive can be effective, but I don't think it will, would improve referral rate on a product that has almost no referrals.”

“Like, you know, you can write a piece of software, and you can pretty much write a comprehensive set of tests for that software to verify that it does everything the way it should. Not so with robotics. As a matter of fact, not only can you not really do that, it's actually physically completely impossible to do that,…”

“when you give the robot the ability to know it needs help, you give it the ability to ask for help, you create a situation where a human can help it, then we keep the robots moving and they don't have to be perfect because they never will be.”

“I don't think an MVP makes a ton of sense if you are replacing an existing system one to one.”

“you have to get into the mindset when you're in fundraising that investors are trying to sell you an investor. Cause like they, they're selling the most commoditized product in the world, the us dollar.”

“at that stage, a million dollar check to a, Multi-billion dollar fund as a call option. And so, and even if you really like the partner there, like it, it just creates all kinds of signaling risk for, for the future as a founder.”

“even though we are sort of pseudo anonymous, the incentives are such that Authenticity is what comes out of that because there's no, there's no reason to try to be like an influencer.”

“And a lot of VCs, you not included, but a lot of investors are like, but the TAM is too small. You're just focused on blogs or you're just focused on selling surfboards. Like, you know, it's not, uh, that tends to not actually be an effective long-term strategy. Cause once you build something that works for a customer,…”

“Now the threshold is you have to be an epic salt, particularly in small business. You can't walk into small business and be like, I'm going to save you three percent on your business. I don't care. I don't have time. Wait, what the hell are you doing? Right? If you're a chain and stuff, that's obviously different, but…”

“So that desperation often turns into it not working, but you're just making it work. You're just charismaing the shit out of it. You're convincing one customer, like you're like force of nature. Um, but when something really works, it actually just works.”

“I think that matters more than what your ARR is in the aggregate, or if you're a first-timer, a second-timer, a third-time founder, can you articulate the business you have And the industry you're building it for, um, can you articulate a plan where you can be 50%, you know, 40% of that market? That's what investors…”

“Is that people weren't really using it to send photos that disappeared. They didn't care that much about that part. What they were really focused on was talking with pictures, uh, because it became a much more expressive way to show your friends what you were doing or how you feel.”

“one of the early indicators for that is that it's primarily used by young women, because I think young women are culture carriers.”

“their incentive structure is such that you're going to by your very nature, right? By, by your, even your existence harm a lot of, Small and startup companies in exchange for a very small number of winners.”

“we had very high conviction that like product market fit should feel having an almost physiological response from your customers where when they see the product, their pupils are dilating, you know, There's like a neurochemical reaction happening. Um, and I remember reading a quote. I can't remember exactly where it…”

“And we learned that like the form of the feature, whether it's in word or not actually matters more than almost the product itself. Cause if you're building a web app for lawyers, sorry, you already lost the game.”

“getting in TechCrunch Is about getting in front of your, your co-founder friends and feeling good that you've got your company covered in TechCrunch. Where, where you really want to be getting covered is in the kind of publications that your prospective customers are reading and staying on top of what's going on in…”

“we often think about building for 10 or a hundred or a thousand customers, but often if you, if you laser focus on the right single customer and just make sure your product is really singing for them, again, you can find 10, you can find a hundred, you can find a thousand”

“what we quickly learn is that actually people want to use software directly, but they also want to have lots of support because advertising is, is a complex topic. We realized that Actually, we need to mix services with software in a way that clients still use our software, but we can help them sort of maximize the use…”

“When you start hiring, you think that if you have two exit developers, two exit marketers, you move two exit fast. But if you don't even really know where you're going, or if the market isn't ready to like take that growth rate, it's not just wasted effort, wasted dollars. It's actually decreasing productivity because…”

“There's nothing more diluted for a founder than a post money safe. It's, and I love post money saves. I shouldn't be saying this. I really shouldn't be saying this because I will turn every prep around to a post money save as I can. Post money saves basically have, and I'll walk you through an example, but like, they…”

“Product matters a lot more. For example, if you're selling into a user who is also the buyer of your product, right? If the user also pays, then if your product is 10 times better, that's going to matter. If you sell to like the VP of X, but it's somebody down the chain that actually uses the product, well, the quality…”

“the only tip that I can give founders is they have to decide if they're building something where market education will help them, and they don't mind having 15 or 20, um, you know, follow-up teams that will be inspired by their idea, that's fine. You can go, you can go crazy. Um, if you think you're building in a, in a…”

“while billion dollar startups get all the hype for 99% of founders, it's just the wrong goal. You're better off focusing on building a sustainable business with consistent growth”

“Look, I think this is the biggest mistake is basically try to estimate correctly what the market size is. You just need to know that if it works, it's going to be big enough.”

“if you're Call it, I don't know, pre-ten grand or 20 grand a month. If you have like more than five people, I don't know what you're doing.”

“You know, that, that business model works, I think, only when capital is cheap, available, and rates are low.”

“Number one, and this is the thing, this, this really pissed us off when we were on the other side of this, but I'm going to say it anyways, because we recognized how true it was now that we're on this side of it, which is, you know, when you see it. And because we weren't like, we were like, well, you know, like we see…”

“the difference is if you, as a generic tool built all those specialized functions, it would become really, really difficult for everybody to use. So you actually alienate your other users. So you're, you're kind of in this circumstance where you have to cater to one market, either you're that mass market tool or you're…”

“venture tends to push a kind of short term thinking. You know, oftentimes there's a conflict. In the business between doing what the right thing for the business would be if you were to run it for the next 20 years versus doing the thing that's going to allow you to hit the next milestone. And the next milestone…”

“my threshold, if I ever do this again, would be I would not start cutting a line of code unless I can get, you know, six figure order form deposits on the basis of a PowerPoint deck. If I'm unable to do that, I either have not identified a painful enough of a problem for the customer, or I have not articulated a…”

“All of the other companies started as B to C. They focused a lot on B to C. They saw our success in B to B, and then they kind of had, um, a double strategy of doing B to C and B to B at the same time. And I think that one of the reasons why we were successful in breaking away from the pack and being leaders very…”

“my view has become, yes, you can optimize from 40% to 50% through better go to market. Let's say on a demo to close, you can do that. You're not going to get from 10 to 50. You know, that's not going to happen.”

“as long as there's a way for them to discover, there's, like, some Basic level of discoverability and you're doing something that people really want, then it takes off. Right? And then I think like, and then if you're good at sales or good at marketing and good at building product, that's like a difference between good…”

“unions are very good early adopters when it comes to cost savings and service, because one, they want to make sure their membership is, is treated on a level like family. The second part is municipalities and public sector and unions, they have fixed budgets.”

“Vertical software doesn't really work that way. The power laws are not in your favor if you, if you, if you aim to be number two or three.”

“AI needs to do new things when it answers questions, so you can't constrain it. But as it does those new things, you want to be able to make sense of them, and you want to put foundation underneath it that's solid so that metrics are consistent, so that permissions are consistent, so that people understand what's…”

“people want to both buy you for what the product's doing today, but they're buying you for the slope too. Like they can see your progress and they want to buy that progress also because like the beautiful thing about SAS is we want them to be a customer for the next 20 years. So they're not buying the product today…”

“everyone hopes that there's just some magical channel that they haven't thought of that when they turn it on, like will inflect the business. What we found that is like the least satisfying, but sort of most obvious conclusion that you could possibly imagine is you just need to do more of literally everything.”

“Like if you ask for feedback, you will get closer to a tire kicker than anything else, which can be good depending on the stage that you're at.”

“I don't think it is a startup's job to change a market or create awareness.”

“And at the end of the day, a VC that invests in you and the seed round, all they need to really think about is will there be an investor that leads the A round, right? And the A round for B and the B for C.”

“If you cannot crystallize it for your investors, You won't be able to crystallize it for customers, and VCs are not necessarily forward indicators of the market, but there's some derivative of what your customers are seeing, because if everyone wants to buy you, you're going to be number one.”

“POCs should be budgeted. You should take money for them. You should meet the business owner. You should understand the use case.”

“If people want your product and you send an offer, they're not going to move out just because you wrote a number they don't like.”

“Don't go the long route. Talk to your dream customers first. Just go to them because those are the people you're after.”

“if you can get five hundred million in revenue in six months, you'll probably lose five hundred million in revenue in six months.”

“In the long term, I'd say you probably have better, you have better margin because you have invested in that customer to a point where the technology is successful, and if that technology is like deeply embedded in the way that organization works.”

“Taking moonshots is really easy. Super easy. If you don't care about efficiency, you find really high energy people who think they're right and are pretty smart. You dump a bunch of money on them and you'll get some moonshots or anyway, some like fairly big companies anyway. It's just not an efficient process.”

“At X, we're trying to be the card counters of innovation.”

“We're paradigm shifting system engineers. We're trying to bridge that gap between basic science and something that's like venture investable, but that's like often a five or six year gap that gets filled very badly.”

“A moonshot for us is huge problem with the world. Science fiction sounding solution to that problem. And some technology or set of technologies that give us A sense that this is a testable hypothesis for making that science fiction sounding solution.”

“unless you're the founder of a company, you shouldn't be at the same place forever. I very much encourage people not to Jump ship every one to two years, not just because it looks bad, but because to actually see, especially as a software engineer, to see the impact of your work takes time. It's one thing to build…”

“So the thing that you normally hear with enterprise sales is Find the CEO. They give you buy-in and then you can make decisions. That doesn't really work well because the managing partner or the CEO at an accounting firm is not going to be close enough to the details to, to be involved in that.”

“The other thing I tell people is the value of your equity today is zero. It doesn't matter what our valuation is. Either we go to zero or we grow significantly more. What the value is today doesn't really matter. So I don't do the math in terms of what the dollar value is. I do the math and what's your ownership?”

“Good leaders often are right. I think there's something very, very, very meaningful there. Like you have to be right. And if you're not, then you probably shouldn't be a founder.”

“you don't really have product market fit until You're growing naturally, and that usually happens when your users are spreading the word.”

“Yeah, however, there are counterexamples where, uh, time to value was actually really high, uh, but word of mouth was awesome, and you know, the canonical example here is Superhuman, the mail app, where you actually had to go through an interview before you got access to it, and I, I don't think you have to do that…”

“I mean, honestly, I made a mistake and I think we should have had a free tier sooner. Everyone else had a free tier. And we decided not to have one because we thought that we really wanted a certain kind of persona where people would come to us for real production applications and they would get enough in their first…”

“Our stance was, like, at least six months to a year, like, hardcore, obsessed, like, crazy hours, sell it, code it.”

“So like there's respectfully no PMF risk. What we do, we get people paid fast. We sold like our receivables. Every business has this problem, just the customer support, and it's, it's just execution risk.”

“And then for copy, you know, plain text, no links, no images, doing things like sent from iPhone, lowercase, They cannot know that it is AI or spam, especially today. Like there's so much email. There's like 50 guys that are smarter than me that are doing outbound. So the more plain text, average copy it is, the…”

“I've tried like nine step sequences, and I've tried three step sequences. I haven't really found a huge delta between them.”

“if you come out for the A and if anyone is listening, if you come out for the A and you say like low teens or like not even below a 10, it doesn't seem like you're ambitious and it just doesn't make sense to like VC math.”

“if you are Thinking of starting an AI native services business and you're like, or any AI company, go and work in an actual entry level job in that sector. You're going to get the level of signal at the, at the deepest possible, most granular level. Nobody can tell you what to do anymore because you're going to…”

“If somebody bills by the hour and their goal is to bill for as many hours as possible, there's not that much incentive to become more efficient.”

“And the worst dollar is obviously paid marketing. Paid socials is the worst on that spectrum. So to me, like I always try to invest in assets and earned media is an incredible asset. It's highly scalable. It compounds. It doesn't have the added cost associated with it.”

“early on, none of that matters because all the, if you're crushing it and if you're real and you're growing, all those firms will want to write checks into you eventually. Anyway, the most important thing that matters is like, who are the early folks who are betting early, who are betting on the team, who'll stick with…”

“The world's best sales team is not going to respect a founder who can't do it themselves. If you're going to bring on an AE and say your, you know, your one quota or target is a million, a million and a half. If you yourself haven't done that in six months, you don't have a right to say you, this is possible. You have…”

“Validation only happens when dollars exchange hands. Period. Full stop. It does not matter. There is no other explanation or excuse other than that.”

“I think, I think honestly was, it was a really good moment for us though, because I realized that we had to move our lives to San Francisco to build a very big business.”

“I'm a big believer in like, you're either fundraising or not fundraising. There's a lot of like, oh, I'm doing these coffee chats, and like, hopefully we'll get preempted from this coffee chat, and all these, it's like, you're fundraising, you're fundraising.”

“I don't think you should move, and I do think you should visit, is the way that I've been telling founders lately.”

“See, most enterprises are not, unlike maybe what people think in Silicon Valley, are not looking at just letting go of people. They are looking at, how do I get more efficiency? Revenue efficiency, my people are already overburdened, right?”

“Top piece of advice is, look, you have product market fit when your average salesperson can go and sell your product without you being in the room.”

“Some VCs play this game and they shouldn't, but they do, which is you might get a meeting and think you're having a genuine conversation with a VC that knows and gets your Only to later find out that that same VC invested in another company that's a competitor, was never gonna invest in your company, and all they did…”

“the difference between going out and saying, I'm going to raise two million dollars, and then you get a hundred K or 200 K, you're only five or 10% subscribed, no momentum, no FOMO versus if you're raising two 50 K and you get a hundred K or 200 K, you're 50 80% subscribed. Huge FOMO.”

“If you give a number, All you're doing is transferring power to the VC because if your number is way too high, the VC is going to maybe just pass because what you want is not market or just doesn't make any sense. And now where you would have gotten an offer, you had zero offers. And two, if it's too low, well, guess…”

“Whatever you give me is the absolute best case. That's how I have to take it. So if you're being conservative, you're Just lowering that ceiling because I can't take what you say and then go back to my partners and say, you know, this founder thinks they're going to grow to two million next year as an example, but I…”

“over and over and over again, they articulated they didn't want 10 AI vendors, so they didn't want one kind of for every single business unit, um, with all these compliance and regulatory and things that they would have to go through, and they were really looking for something that was considered more enterprise grade,…”

“I think much of the practices that worked very well in SEO continue to work, but the contrast is turned up on, on some of the sub bullets. In particular, the importance of information gain. So adding materially like net new information to the market through the content that you write.”

“And so to get the most from an AI model, it's much less so the capability of the model, it's much more so the context that you can have available for the model, right?”

“most people have the inverse problem. Which is an enterprise comes to them and waves a ton of money in their face to say, well, what if you go build all this and do our security reviews and do the rest of it? Most people should say no to that.”

“Notion of we found product market fit and let's scale, which maybe was truer in like a pre AI world. If it exists at all in a post AI world, I think is much more fleeting and you sort of have to be evolving at a historically fast rate on team.”

“Agents doesn't care about the color of the button or the size or the creatives and things like that. What truly matters is merchandising, right? Like finding the right product, the right categories, the most relevant things.”

“And I think that comfort doesn't make them less motivated. I actually think it just makes it easier to like, okay, more things are taken care of. I can take care of my family and now I can put more energy towards the company. And if you have somebody who has a good work ethic, it's not going to shift how they show up…”

“I, I had a deep belief that the Sixth Sense signals into Salesforce, we would be dead, right? We had to get people into the Sixth Sense platform using the Sixth Sense platform and using that as a system of record and a place that they go every day, which was really hard to do back then, right? Like everyone wanted to…”

“there'll be a set of deterministic rules too, that humans for a while will have to like layer on top of the LLMs, everything that we're doing, because I don't think it's going to be fully agentic forever.”

“a lot of companies right now are doing point solutions where they're making today's process better... and there's so many like better note takers are better this and it's like, that's, that's just making incremental progress.”

“you're not building a category if everybody loves what you're building. It loves what you're doing. And so whenever I would get a no, I'd be like, thank you. Because I don't, if everybody loves it, I'm building something incremental and it's too easy for people to block. And so I actually want people to reject it.”

“I know a lot of people talk about ICP, but I also think it's important to find like persona, maybe even before ICP.”

“My opinion is you get a lot of better feedback when you try to close and that feedback is less squishy versus asking somebody, what do they think, et cetera.”

“So if you have a tangible outcome and then you have a tangible product and you try to close on that, I think if the pain's big enough, people will just buy off a slide deck.”

“My opinion is it's much better to start in like the lower mid market because it's more repeatable. There's more volume, et cetera. And also have a couple of conversations with large enterprise to make sure that like it validates for them as well.”

“Like just throwing a horizontal, like AI model on it won't work.”

“And the third thing we said, which was, I think, surprising to a lot of people is that why don't we do a POC in production, right? That was the biggest thing that I would say got people to take notice because they're like, they're this sure of what they built.”

“And in my mind, an AI product which is built by accountants, and by the way, I'm a former accountant, will not scale fast. People shouldn't be using that AI product that I'm coding. They should use the AI product that I'm architecting, because I can tell you what the problems are, how to build it. But just like a…”

“And if you get too much into TNCs that, you know, we will only provide 98% accuracy, and therefore you will pay, then you're forcing them to think too much early on, and you are, um, you are forcing them to cover your ass, uh, cover their ass too much early on. And then they'll be like, you know, it's not worth it.…”

“these law firms or professional services firms who have a lot of kind of perverse incentives, right? They don't really want to cut hours because they bill by the hour”

“I think most first time founders or founders who haven't yet had a good exit deep down, they're often playing not to lose. They're not playing to win because the reality is you put so much into a startup. It's your whole life. You're making very little money compared to what you could be making. And, and like, at some…”

“AI out of the box will never be that amazing to somebody who actually knows what they're doing. It's amazing to somebody who has no idea what they're doing, but to, to SME, they're like, this is crap.”

“Paying from the beginning. I think that's really important to make sure that the customer says this thing is valuable enough for me to pay.”

“And the reality is that early stage companies that they don't want an accounting software. They just want the work to be done. They want the peace of mind. They want it off their plate.”

“I really think that is the best way to build an automated product because the engineers have to understand the domain very, very deeply.”

“I think most startups are not enough, are not being enough, are not meant to be Standardland businesses, but more like a feature in a, or a product in a bigger business, right?”

“Business conversations are deterministic, and it makes no sense to put a pure probabilistic thing to do a mostly deterministic process.”

“That actually interconnects things, not based on semantic, which is knowledge, but based on intention, which is in any conversation, in any process, there's one single unique intention at a time. And so it's a network of interconnected intentions. Anyways, we are getting far more technical than that, but that's the…”

“whenever a pattern is detected, a process that is defined, it's being repeated. We're servicing that case every time in the same way. Why keep it probabilistic and call upon a model every time? It has become deterministic.”

“Like, when you're doing security, especially, like, they're putting you through procurement and also allowing you to have access to certain data is basically a higher bar than writing, like, a hundred K check.”

“ability for like an engineer to be onsite with the user to learn something and for a 72 hours later to ship a pretty large feature that that is pretty game changing that we could not have possibly anticipated. That's where we're like generating a lot of alpha right now.”

“And that is why I think founder led sales in particular, where you're controlling sales, BD and product all at once. The only way that it really works in the beginning.”

“I think first-time founders often think that they can just, like, talk to users, users, users, and, like, find the answer to their problems, and we're just not. And it's not to say that you shouldn't talk to users, but you need to have a very clear idea that, like, no one is going to tell you how to, like, build your…”

“open source is very good when it comes to, like, the build versus buy, because In a way, it removes the build, but it also removes the buy. So as an engineer, you just take open source, you don't have to build, you don't have to buy, but you get the value out of it.”

“Initially we're very focused on Vanity metrics on GitHub. Those, especially for open source, are very important because these vanity metrics, I don't care about how many stars I have, but I know that whenever I look at a project, whenever I look at the library or anything like that, I look at these numbers, not because…”

“you don't want to invite contribution too soon in a project because that's going to disrupt like building the, the foundation of the, of the project.”

“You are a CFO of a, um, 200 employees company. You use Excel for 15 years to run your finance. You will never leave Excel. So all these web-based FP&A solution, FP&A web-based financial system, you will never Even think to move from Excel to the web.”

“But my personal opinion is that eventually you need to go to code. Eventually, if you have like 10 people that all come into a low code solution and through clicking some buttons, And getting a system prompt together, have like a viable product. Eventually those folks are all going to compete with each other. You know,…”

“The fact that you're an outsider is a really good thing because you don't look at it the same way. If I had 25 years of banking experience, I'd just be so coded in a certain way of like, well, this is deep. I can't do anything more. Let's just do one country, then add another. Because you didn't have that, because you…”

“You should start with, can you give the product for free? You should start with, can I pay you to use the product? If I can't pay you to use the product, there's no scenario that you can charge for the product.”

“It sounds obvious, but, like, I would advise, like, not to do that ever, right? In other words, like, no matter what, if you are raising, the round's pretty much already done. That's the narrative.”

“That's what people should do is whatever their first check is in the round. Just say your total round is that plus like 20%.”

“if you have no competition, and you've like never had any competition, it's like you still have no competition. You probably don't have anything that people want.”

“it's way easier to execute better than it is to find a concept that works.”

“really your only tools, the speed at which you ship product and the speed at which you iterate, you know, that's really it. That's like kind of the only competitive advantage to be honest.”

“they are competitors, but they're competitors locally, right? So if you look at it, you know, in, I don't know, Los Angeles, in one neighborhood, there might be two or three personal injury labor and employment attorneys. Representing that area. They'd be competing strongly with each other, but outside the city,…”

“And when you think about that complexity of, oh, let's just create a portal for all 21 companies to log in. That's Fugazi. Nobody, you know, nobody's logging into your Pablo's, you know, construction owner system. Nobody wants to do that. And that's not realistic.”

“Many of the software packages they still use today and by, by the way, this isn't, they actually procure the were built before you were born. Probably Pablo, like this is like crazy software that isn't going anywhere. It's a hammer that just works for them.”

“Oh, it's always easier to sell it. I think it's because, you know, we live in tech and we understand the nuances of that putt for dough moment. If you make a mistake, it's going to cost you your company. It's a high risk business, but when they go in to justify it to a CEO or write the check, it's really easy to…”

“every digital transformation. There will be a loser. There will be, I'm sorry. And, and to pretend that there's not is foolhardy, but find out who's losing.”

“What I realized in FinTech over those, you know, 1618 months, it's a very hard, high churn product. FinTech products are extremely high churn. They're not sticky because in some ways they're experimentational.”

“So now you've got to compete with incumbents, foundational models, and new entrance. So competition becomes a primary risk. All of a sudden the ability to deliver incredible value is not nearly as hard as used to be, but The counter to that is competition is much harder than it was.”

“And so the, the 10 X better always has to be caveated with like how important is the thing that's being worked on. And if it's a really important thing, Then two X better is a huge outcome for, for the end user, let alone 10 X.”

“One of the mistakes that I, I see it like first time early stage founders make is they're like, oh, I'm gonna go hire the like person from Cisco or something. You know, I don't know, like the big leagues and I'm gonna bring them into here. I have no idea what to do and how to operate in this kind of environment. What…”

“And I think one of the very common mistakes Many of them made is they waited way too long to build out sales. And they built out sales only when they needed it because their PLG business started stalling out or whatever. And like, that is too late. Then you end up in like a very hard shift, kind of whiplash moment for…”

“Don't listen to what investors say. They're not close to the customers and the users. They don't actually know. They could maybe be a proxy at best, but they're pretty noisy proxy.”

“So actually a lot of surveillance system innovation coming from China propelled synthetic media developments across the world.”

“most of the greatest SAS companies were doing this historically too. They were selling outcomes. And they were delivering those outcomes in a lot of cases with, you know, a huge customer success or pro serve portion.”

“AI doesn't have to be perfect. It just has to be better than the humans. And when I especially take that route of, like, if you're throwing away millions of alerts a day, because you don't have the human manpower to look at them, if I can look at them with an AI that's just 80% as good as a human, that's way better…”

“And I don't buy into this idea that as long as you get 20%, it just doesn't matter what you pay. Like you just intrinsically doesn't make sense to me. You know, you're going to affect your ultimate return. And if you do it all the time, you know, it's going to have some sort of an impact.”

“The VC on the other side has a portfolio. So when they're like, yo, swing for the fences, go for it, try and grow faster. Like, frankly, their risk is not your risk. Like if you fail, it sucks for them, but they got 20 other companies. Right. And so. You doing that secondary to me is getting you closer to that, where…”

“Think about how unique it is that as a product, we don't measure ourselves by how much time you spend using our product. We measure ourselves by how much time you spend not using our product. We want you to sign up one time and never use Metropolis again in the context that is always running in the background.”

“Because more and more software is getting written, more and more software is getting deployed, but the quality and quantum of human work was getting degraded.”

“the key thing that we discovered early on, which I think is a differentiated IP that we have, is that very much like the human brain, and actually one of our founding engineers is a neuroscientist and a computer scientist, and really helped us think through this. Is the idea that it needs to be editable, like the human…”

“if you can solve that issue, if you can have millions of people knowing about what you do, it doesn't matter what project it's incubating. It could be e-commerce, it could be SaaS, even like a PDF guide.”

“true product market fit is like purely based off referrals. If people love your product to the degree they say they do, they will refer other customers to that product.”

“anytime lots and lots and lots of money moves from one category to another, client server to cloud, or, you know, TV advertising to online advertising or when pharmaceutical advertising wasn't legal and then it became legal, right? You have the chance to build a very large, very meaningful third party measurement…”

“sometimes there's a disconnect between what the operators are doing and what the CEOs think they're doing. And if you build software for what the CEOs say they're doing, they want, it won't get adopted. It just won't get adopted. You know, you might get a contract, but you won't get adopted. So next year, well, you…”

“It's very similar to what's happening right now with apps and agents. How do you bring apps and agents together as opposed to just talk about the future, which is agents, and the past, which is apps. You know, there was a time when SQL was being looked at in the past, and NoSQL was the future, which obviously happened…”

“Without SQL, you can't say you have a great knowledge graph.”

“If you want to build a generational database company, you need two and a half things. The first thing that you need is that you need a new workload, because if you want to make it as a really large billion dollar plus database company, you need a reason for more or less every company in the world to need a new…”

“you want a corporate lawyer who sees a lot of activity and ideally a corporate lawyer who never works with VCs, but only ever works with founders.”

“More commonly, there will be some of the materials that those systems find even on the open web are at a date anachronistic. The law has changed. There's been some statutory amendment or there's some new case law or, you know, some law firm wrote some guidance and it's now been left up on there. It's quite stale. And…”

“those companies still need to do product well and marketing well, but the way they win, the way they become dominant is by being the best at sales because they understand the deal mechanics the most. They understand how the buyer's gonna make a decision, and that's how those next-gen something companies end up being…”

“One is they used their fundraising as a brand tool, which is, you know, it has its pros and cons, but they kept raising Many, many different rounds kept raising their valuation, and that's a very dangerous game, by the way, but for them, they were able to pull it off very effectively, and people kept hearing about…”

“What you need to ask yourself is if the way I got from zero to one, Gave me a recipe that I can pick up an AE from the street and make them be able to do the same thing I just did. If that's the case, then you're gonna accelerate from one to 10.”

“Like don't think about marketing funnels or PLG or like hiring salespeople or any of that stuff until you as a founder have figured out how to tap out your existing networks. I think the bulk of the power that you're going to have pre series A is probably going to come from there.”

“Then I hired two salespeople, because if you're going to do that, you never hire one, you always hire two, because that way they compete with each other and G each other up.”

“I think there's, like, some sort of, like, power law distribution with, like, what social media does for businesses, where for most people having, like, a Social media feed that, like, looks nice. It's like, doesn't do anything. But if you actually have, like, a viral social feed, I think it'd really be…”

“our thesis here now is like, neither a regular terminal nor a regular IDE is like the right approach for agentic developments. Like you really want a tool that's built for this workflow.”

“Realistically, there are a lot of people, and this includes founders that can do it once and they can't do it again because it's just fucking hard.”

“If you're serving this kind of client, especially investment management, it's very difficult to convince someone to invest millions of dollars with you when you don't have millions of dollars under management, right? Like this is just a chicken egg zero one classic zero one problem. And so one of the insights we had in…”

“It's very difficult because of the information, because the people actually doing the work are subcontractors of subcontractors of subcontractors, and they're not going to report what's done, what's not done in the now. And then that means that to know what's going on, You need somebody to walk around and check…”

“And we ended up realizing that even to the level of viewer tracking, Like the minutes that they use this product every week as a metric. And that is such a wrong metric because the thing that you need is to succeed to deliver to them what they need in 10 minutes of use every week, because that's the time they have.”

“Like, anyone who is too lazy to outbound, you're just not gonna make it. Like, that's just not, you just gotta get over that. Like, you have to be embarrassed. You have to do, like, all these, like, really awkward things.”

“my co-founder and I, we still think like to get to ten million, you just have to work really hard. That's, that's really it. It really, it sucks. And it's like a lot of paid, but you can just work your way to ten million.”

“The thing that matters, you know, in his view, and I would tend to agree is not how fast you get to a million, but how fast you can get to 10. Like that one to 10 is really the thing that'll set you on this kind of different trajectory.”

“my hunch with AI space is that you can't validate problems by asking people because, like, they won't able, they won't get it.”

“For me, at least the way I used to think about it was, like, a lot of these folks are, like, independent developers who are doing personal projects because they're, like, very interested in the new tech, and, like, to charge them right now is, like, kind of a disservice to them as well as me because the value they get…”

“VCs will give money to what is a hot commodity, so then something can give them, someone will give them up round, and you can go to your LPs and say, hey, I'm up 90% on my portfolio.”

“old industry Small businesses seem to be hurting the most in today's economy. And why do I emphasize old industry? It's because like, I'm not talking about drop shipping businesses or blank street coffee in Tribeca or sweet greens, the franchise owner. Like I'm talking about Joe Schmo who started an independent…”

“one of the things that Rubrik got right was, uh, picking like an old problem which nobody was, ignored problem, right? When you ignore a problem, You get to be the only person kind of doing it. That was like one secret sauce that Rubrik had.”

“I don't know exactly what I want to build, but I know if I talk to the customers, like for a few months, and we find a common product, we can find something. It's, it's guaranteed.”

“investing in a services company is risk-free because you know that by design, a services company is always profitable. So worst case happens, you have to downsize, but you don't have any risk of, you know, sinking millions of dollars and something that nobody would want to buy.”

“If they want to take their product to the cloud for real, they have to rewrite it entirely. You cannot adapt an on-prem server to the cloud, or you can put it in a virtual machine, but it's a fake cloud. It's not, it's not real new architecture.”

“There's two things that you can't have at the same time. You can have a fast decision time, or you can have very high stickiness. You can't have both, because enterprises are very aware of the risk of the vendor looking, and so the more critical you are to an enterprise, the more prudent they will be in adopting a…”

“When you double every year, Nothing is stable in the company, right? Every morning, the organization changes every day. It's very traumatizing for, for the employees. You can do this over a few years, but if you do this on long, long time, it's like everybody's lost. Doubling every two years. Okay. It's cheap fast, but…”

“And what it did for me, like, I didn't have to think about product roadmap. I didn't have to even write my product roadmap anywhere, uh, cause customers would tell me every single day about the things that matter, uh, versus, you know, if they told me like once in the blue moon, then through very Darwinistic natural…”

“LLMs are just, like, much more farther along, and they have, like, a very well-defined, like, path, and it's really just about scaling them at this point, and, like, You know, working on reasoning, improving general intelligence. I think for, like, media generation, it's still too early for that. Um, and, like, we're…”

“a lot of the clever approaches were, that we were doing in academia were ultimately, like, nothing in the face of scale, and that, like, if I wanted to build something impactful, I felt like I needed to do it in, like, an industry setting at that time.”

“there's certain technology that will get subsumed by models, so I think a lot about, like, agentic orchestration is, like, a good example.”

“People should consider bringing on a talent person if you're venture-backed really early on.”

“which to me was the most important thing with co-founders is like, if you assume conflict is a healthy and necessary and evergreen thing, check that you can do it good in many different situations.”

“Well, look, founding a business is not economically rational because the risk profile on the return, it makes zero sense really. Like if you're making any normal bet, it's like playing roulette with 350, um, you know, options rather than 36. Like it's an idiot's game to go in there and just start betting seven years of…”

“the idea of being the salesman or not is rubbish. Like it's actually even better if it's a product person or an engineering person that learns that talent, because that's where you get everything early on”

“if you're the, the contract dude in company X and somebody comes to you and says, I'm going to literally do your job. Cause you're the buyer. And you're going to send me your job. It's going to take you three days to onboard me. And then I'm going to do your job each time in an hour. Then you send it out. And I'm a,…”

“for all the science that you might think exists in this space, people will tell you that they're the smartest operator in the world and they came up with a plan when the reality is that 90% of this stuff, 99, is people driving off their gut, chasing the things that they have that are slightly more advantageous to them,…”

“a kid gives you an incredible ability to get stuff done. Like what I do with an hour now is order of magnitude more impactful than what I did with an hour five years ago. And I used to think not having kids was a competitive advantage as an exec, because I just worked like crazy. But honestly, having some degree of…”

“And I actually think refactoring fundamentally is a product-driven question, not just a, like, tech debt-type question, right? I think, like, this quote-unquote, like, tech debt thing sometimes is overly, um, how do I put it? It's, uh, I think, like, overly abstract of a concept. Really, like, you need to refactor when…”

“I think a lot of founders have a tendency to self delude into believing like, oh, as long as they just like keep on, you know, um, doing it, it'll work out. But while they think that they also aren't actively trying to prove that it's going to fail, like, you know, they're not really trying to seek out truth.”

“my thesis is by creating a better top of funnel, even if you're a visitor to conversion, a visitor to paid ratio is much lower, a bigger top of funnel makes up for it.”

“product market fit doesn't guarantee net negative churn in which your, your contraction or your, your downsells or even your cancellations are made up from upsells plus, you know, and you want the upsells to ideally be more.”

“If you run the survey when the product is free, even if it's not as good as the competition, people are very satisfied because it's free. I'm just telling you the reality. You can go run a survey on a free product versus a paid product, and if the free product versus the paid product, they have the same features, but…”

“You're not going to go through referrals and word of mouth at the beginning. Most people don't know this, but branding really kicks in after your attempt. Like most startups don't think in tenure horizons, but if you actually look at your brand name and this recognition within its category, if you're doing a good job…”

“Most companies die because I think they get the culture wrong because, uh, it's not fucking fun to work at your startup where you're grinding 13 hours a day with people you don't even like.”

“if you actually do an actual sales call on, like, like, a genuine demo of the product, then nobody's gonna fucking watch your thing, as, um, A, it's not interesting, um, and, and, like, like, like, like, B, it's, well, Unless it's super informational and you just have, like, the most crazy fucking product experience…”

“The, um, benefit of a launch is that it gives you the right to try again. And try to go viral again. And if you can go viral enough times, then like, bro, you will, you will like, end up like Cluey.”

“you have the fucking distribution potential goldmine that you get out of just making something very reactionary, and then reacting to all the reactions over and over again, cyclically, it will literally, like, spiral you up into something that you never even knew existed.”

“if you're a good company with a good founder, you're probably gonna raise money from someone else, if not me, uh, and you'll probably be successful regardless of any investor input.”

“I've also found that if you don't build a thing up front, it's often actually hard to build it after you launch. This is, like, pretty contrarian, but just when you have users and, like, Yeah. You have to worry about things breaking and like fixing bugs and et cetera. It's just like, it's, it becomes hard to do new…”

“I found that a lot of the companies that I worked with that had massive success didn't do the stuff you're supposed to do. They didn't do the business model canvas. They didn't do the kind of experiments you're supposed to run. They didn't hire the people the way you're supposed to hire them. And then I would find…”

“Iterate and execute perfectly in lean startup mode, but if you're pursuing a small idea, you'll iterate to a local maximum.”

“most startup ideas I find come from not having a formal assessment process, but rather by living in the correct future and tinkering with what's happening in the future. And by tinkering with the future, you learn what's new about it, but you also learn what's limited about it. And so what I like to say is you want to…”

“a great startup Forces a choice and not a comparison, right? Like a great startup. If, if, if a customer says after seeing your startup idea, how does that compare to X? You either explained it wrong or you don't have a big enough idea by definition.”

“And so the, the best startup ideas tend to be the polarizing ideas, you know, ideas that probably most people don't like because they're not ready to live in the future, but a tiny subset of people say, oh my gosh, where have you been all my life? I can't unsee this.”

“I think for the most part, raising a lot of money early is, um, it, it's, it, it makes the company worse rather than better for the most part.”

“fish, typically, the majority of it isn't farmed, right? Um, so wild caught, there's, Unpredictability when it comes to how much is caught, the timing of when something is caught, the pricing of the catch when it lands at the dock. So there's a lot of variability there that in retrospect is smoothed, smooths out…”

“I think market always trumps founders when there's like a bad market and a good founder market wins.”

“the reality is that I believe now more than ever, having been a part of helping to build this company, I believe that At the end of the day, the one thing that's out of your control controls more of your destiny than anything in your control, which is the market adoption and where the market is in adopting.”

“the difference between being very, very, very, very early in something and being too early in something T O O of course, it's really only one word. And the word is actually not time. It's bankruptcy.”

“Over raise. Cash is literally the single most important insurance policy that every single startup has years before they're profitable and capable of standing on their own two feet. There's no amount of optimizing for dilution that will ever convince me that raising a lot more, not a little more money is the right…”

“you have to make things that people aesthetically like, and they feel like, you know, it looks polished enough that they, that they don't focus on that. They focus on the actual product feedback”

“I think for me, the first, like, sort of sign of Product Market Fit was, we were signing customers that were paying us, you know, as, as much or more than all these ones that I had personally, like, spent all these, you know, hours on hand-holding, And I'd never even heard of this deal or that, you know, this, it just,…”

“when things get hard, you need one decision maker. I believe this really strongly. So I still believe the fifty-fifty rules that a lot of VCs try to push is Uh, not the best because I really do think that no matter what the decision is, there has to be somebody deciding.”

“We raised, we raised really well on crowdfunding and it's also great marketing because you're always online. You're like, people are talking about yours, like great marketing tool, but it also creates a lot of problems in the longterm.”

“it kind of worked, you know, half million revenue is something, but it's not, Enough to build like something generational or, or a grander vision than, than notes. I think we can't realize. Yeah. People don't like notes.”

“And hard to actually physically impossible to shortcut. Like every single parameter in our API is from like us, like hearing from a developer, figuring out like the core pain that they have and shipping it and like seeing how they did and then tuning it again and, and trying again with a bunch of other developers.”

“I think product market fit can be achieved with, like, one person and one user. I, I, I think it's as easy as that. You can have product market fit immediately with an extremely, extremely, extremely small market. End of one. And then you just need to achieve product market fit with two, and then four, and then five,…”

“It's so hard to build an app that now you have to amortize the cost over, like, a million users in order to make it worthwhile to build something.”

“some things are features, not, not products or companies. And I, and I think that what we, and also some things I think can only, uh, they can't really exist as, as standalone companies. They only really, they're only really like internal tools that they can't really break out from that because They, they don't, you…”

“the problem with a ten-page deck is you could go in and Change your whole strategy by changing two slides, you know, like that's not focusing, you know, it's, uh, and I feel like that's, that's so easy to just throw a couple of ideas on and, and, uh, and, and not have to really go through the clarifying experience of…”

“people might be the exact perfect, right? A player for a particular moment and a, and a particular period. And then they may be able to do that. Somewhere at some other company and they may not be an A player for when you're, when you're, um, at the next level of scale. Right. Uh, and so I think that that is like,…”

“I think it's a mistake to go all in on, on, on equity too early. And I think you have to be cognizant that, that you might need to move the pieces around.”

“once you take an A round, it's really hard to get off the VC train. You've raised 12 to fourteen million dollars at that point, your look, , your preference stack is pretty high. Like you are committed to growing real fast. So if you're going to make that choice to get off the train, I think seed is basically your last…”

“The synergies were much more on the revenue side. I think there were some on the cost side, right? It's like, you know, we, we, a much smaller marketing team could go across all of them and, and, you know, a smaller sort of engineering team could sort of handle all of them, reduce costs on AWS on scale, et cetera. But…”

“Most of what you will learn doing that will end up being wrong. Usually these things come, come together when like rubber hits the road, go out, build something really small, like around what you want to do and go sell it. People will say a lot of things in surveys, let them vote with their wallet.”

“If there are the millions of businesses that we are claiming, then other people see this opportunity as well. They're going to go hard. They're going to go raise millions of dollars to capture it. And they will steamroll us unless We're like going at as hard as they are.”

“When we crossed a thousand, that's probably when I actually thought like a hundred, it's like we have a business, a thousand, we have product market fit, 10,000, it's, we have a path to building something large and amazing.”

“I think one thing where we've been a bit different also from other, um, uh, scale up stories is that we've always been really, really quality driven. And that's something that a lot of people say they are, but in the end, there's also this truth of, Hey, okay, be, be scrappy and quick ship faster. And it's okay to be…”

“And, um, and I've spoken to other entrepreneurs who also really believed in this model of MBS, but they could not get it going because at some point their investors, you know, started asking, where's the revenue? Um, but if that actually happens, it's already too late because it means you've got investors on board who…”

“I think is really important for a bunch of co-founders is to like feel a lot of friction between each other to like get to the root of problems.”

“I mean, you can build a hundred million dollar business just selling t-shirts, right? Like, which is like a completely commoditized product.”

“The other one, which I recommend for first-time founders, it's just like, build a SaaS, you know, build a GPT wrapper, um, you know, have a great landing page, you know, try to do everything you can to drive traffic.”

“the best thing you can say to a VC is no. Yes. Like that's when they want you. Um, I, I like to refer to them as like high school girls. It's like, uh, they, no one wants you until, like, somebody does, and then everybody wants you, and then, but, and then if you say no, it's like, you know, everybody wants you.”

“the thing that I, I think people don't realize is the more money you raise, the less people actually look at your, your business.”

“all you're doing there is you're diluting yourself. Um, you own less of the company and you now have more people to answer to. You can't just answer to your customer and your employees anymore. You have this investor class that you have to like answer to, uh, and they want return.”

“it's like a 30% gross profit. So if you sell a box of meat for a hundred bucks, you make 30 dollars on it after you've shipped it and credit card fees and all that. Uh, so 30% gross profit, basically 10% to operate the place. So salaries, technology, rent, et cetera, et cetera. Leaving 20% left over for marketing and…”

“I think that founders generally focus too much on their business plan and not enough on their lifestyle plan.”

“It's really hard to be a meaningful, important person in the journey of a founder if I appear in front of them at series A, series B, and the only way to even have a meaningful role at that point is to write a very big check.”

“You actually want to be fuzzy, intentionally fuzzy, because you don't want to be adamant about this is exactly how I'm going to build a business, because you never know. You put the product out, And the customer looks at it, they might be using it for a totally different reason, and that might shape the company in a…”

“That's a pretty good indicator of product market fit. It's like, if someone's willing to endure a bad user experience and give it a high NPS score, uh, you're, you're sort of moving in the right direction.”

“I think that's, that's where I think a lot of these companies went wrong, because you can't control the full experience if you don't own the asset.”

“I think there's a lot of value in your first 10 or 50 customers being on shorter term contracts, because if you sign people to annual agreements, it's going to take you a year to figure out, do they actually like the product?”

“if you don't have customers that aren't coming back to you, then you haven't cast a wide enough net of who could be using your product.”

“I think as a founder, it's your responsibility to be taking the first hundred sales calls, because again, you're figuring out pricing, you're figuring out who the right customer is, et cetera.”

“in most kind of generalizations like this, I find a lot of sales like companies Are fantastic. It's solving for complexity... For a product-led company. It's like, that's actually your detriment sometimes is you create something that is so complex, does so many things. And then users are like, I, I don't need How do I…”

“when you look at the economics of a restaurant, when, when you look at the fixed costs, the variable costs, The margin on getting incremental business is very, very high because you're already paying the staff and their overhead.”

“Typically what you'll see in FinTech, and this, this actually surprises a lot of people, is that Fintech is actually more of an art or science of integration and orchestration across other people's technology than it is a real science and art of building your own tech. Cause typically what people will do because of the…”

“demo to close, if you want to be pedantic, like is less a measure of product market fit and more a message of like a more, more a signal of like message market fit.”

“That NPS score, oftentimes you think you're measuring how much people love your product, but you're equally, if not more, you're measuring how much people like customer, your customer success, your customer service, because if people are treated in a really good way, they'll have great things to say about your company,…”

“When you're a startup founder, you really have to think about what's important to you, what you're willing to tolerate, what is, what is a good outcome in your opinion. My suggestion is to not factor in financials into what a good outcome looks like.”

“Hey, in the early days, like you code or you sell, there's nothing else.”

“things are not going right if you are in control, like you really in the early stages should feel like you were kind of drowning. And that's when things are, you know, paradoxically going right, because you should have so many things that must be done as a react, as a kind of, as a fallout of fulfilling a real need.…”

“if you want to go fast, there's nothing like having a single threaded owner who can really, uh, focus on, you know, their specific kind of job to be done.”

“What's really significant is shape of curve, and I always, uh, not trying to analyze, like, absolute numbers because it's irrelevant at the Early stage. Uh, what's relevant is the shape of curve and specifically I'm trying to see is it, uh, watering is like plateau or it's like just like falling down because if it's…”

“I haven't seen like not so many people who became successful from the first attempt, but, uh, I have never seen any founder who would not become successful from five attempts.”

“if you can enter a market where there is no competition, and that doesn't mean there's no market, right? No competition doesn't mean there's no market. So, uh, I think spending a bit more time Finding that, um, you know, finding that, you know, finding, uh, that market where there's no competition or, you know, victory…”

“enterprise restaurants, you need to go through the proper channels and sell into the enterprise and not just work with individual franchisees or operator groups. Cause it really upsets headquarters, if they haven't vetted the things that.”

“We learned that customers, in fact, don't like chat, right, to book and to browse. Like, they like chat for customer service, they like chat for, like, notifications, but they do not like chat for searching and browsing, because it just became so frustrating, right?”

“Like, ultimately, no matter how good the AI is, If you're buying a hotel room, if you're buying a physical product, if you're doing anything that requires visuals like pictures or a map, you're going to need a UI. That's fundamentally required, right? It doesn't matter how good the AI.”

“98% of customers, all they care about, the only thing they care about is getting the best price, right?”

“And for most companies, and for most products, there's typically one channel that works really well. I mean, if you even want to oversimplify it, think of it as like Google versus social. And social, I'll put in Meta, Facebook, Instagram, TikTok, right? And what happens is a lot of companies are like, oh, Google's…”

“if you have, if you can make it like a qualitatively different price profile, I think, you know, that's absolutely as much of a competitive advantage as product quality or anything like that.”

“being, you know, 20, 30% cheaper, like, that's not enough to really get people to, like, think about it.”

“There are some domains, you know, marketing, fundraising, where I think you get kind of disproportionate leverage out of your ability to storytell and exaggerate in ways that like, not trying to lie, but like trying to communicate your point in a, you know, again, in a sharper and like more, uh, emotional way to people…”

“you burn out, not because you're just spending too many hours on something you burn out because like, you don't have that sort of energy sustaining environment that allows you to, to kind of go beyond what you might expect yourself to be able to do.”

“the single most important determining factor to getting to product market fit is actually who you choose as your co-founder.”

“it's not that governments are in the cutting edge of doing cybersecurity. They typically aren't. Why? They don't need to, because they're not connected to the internet. So the risks are very different than the risks of the average company.”

“That's what we did because we said, okay, we want to start engagement. We want to start selling. It will take us time to build a software. Let's in the meantime, build a UI. We'll do it manually behind the scenes. We'll learn how to do it right through the manual work and we'll automate it over time. That was the idea,…”

“I would only do something manually. If I know I can automate within three, four months, I wouldn't do something manually that I know it will take me at least a year to automate, which is something we did in insights and eventually it slowed us down.”

“And I also think there is a huge merit to being number one in your market. I prefer I don't know. I prefer eight percent in a company that is number one in its market than 15% in a company that is number three or four.”

“Don't think I need to, you know, do the exit and, and cash out and my next one will be a lot better because you might, you know, hit huge pain, huge market. You need to go full force. There are amazing companies that were built by first time founders. I don't need to give you names, you know, you all know them. I know,…”

“The single reason is that our product kept getting customized for every customer.”

“The middle road is what kills you. The middle road of taking a hundred K, 200 K for customization that takes six months. You end up losing gross margin to get this magical ARR that every VC wants.”

“if you are not clear on what you want to build, when it comes to the push and shove of who's paying for that extra feature, it ain't the institution, it's the startup. Not because the institution's big and bad, it's that their budget's been locked down for the year, and they don't have another hundred K. And if the…”

“You always call the CEO day one, right? You never call lower. You call the CEO every single time, even if you don't get through, you know, for the stars, you'll land on the moon, right? So in general, we always go C-level, head of rev, CEO, Head of revenue, head of global.”