YouSaid · the spoken record

Winston Weinberg

lines on the record: 91
first: 2026-01-19
most recent: 2026-01-19
sittings or episodes: 1
sources: podcast

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“Of users in the Q4 before that, right? And we didn't quite have the infrastructure to support that. And now if you look at our team, it's almost like 40% of our entire EPD org is very senior from like a databricks or something like that, infrastructure engineers. And it's a long-term bet that as you get these a genix systems that are processing tens of millions for us, I think last year we almost did like half a billion documents or something like that, that you need the infrastructure to actually support that. So it's not just about how do you win the demo and how do you win the deal, but how do you actually create an enterprise very scalable infrastructure on your product? And I see a lot of AI application layer companies not doing this.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“But actually, I think this is important. This is something that's interesting. When I look at a lot of AI application layer companies, if you go through their LinkedIns and you look at the engineers that they're hiring, it's like 90% front-end engineers, which is interesting to me. And a lot of that reason is I think Vive Coding works much better with front-end than it does for Infra. And a lot of, I think, what's happening to AI companies or is going to happen to them, and it happened to us in early 2024, is you do a bunch of front end and you make really pretty UIs and really nice demos, right? And then you use that to land all the customers. And now you have a lot of actual active customers. And you haven't invested in the architecture and the infrastructure of hundreds of thousands, millions of customers using your product. And we kind of made that mistake in 2023. And in the beginning of 2024, something that kind of slowed down our shipping velocity is we added just tens of thousands.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, we were in Airbnb. The engineer he had joined, who was our first engineer, Gabe, was basically coding everything before that. He had been there for, I think, a month. And then we onboarded a 4,000-person very large-scale enterprise security was incredibly important team. And so it was just bandwidth. Like when you're scaling that quickly, it's harder.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Just bandwidth. Like when we signed Eno Sherman, which was our first customer, we had four people. So we did a 4,000 person enterprise grade rollout with four people.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Love him I mean, I definitely respect them. And I think one of the things that they did really well is I think they did a great job in Europe. And this is back in 2023. We're not that, I think they're like six months after us or something. It's not that big of a gap. And I think like one of the things that I would have done differently in the beginning is just invest more in Europe in 2023. And actually, a lot of our first customers were in Europe. But having folks on the ground here is just really, really important. And we're respecting kind of like the different cultures and how to productionize that and all of those things.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“I think that if you're number two in the market, one of the things that can get you a lot of attention is just attaching yourself to number one in any way, shape or form, right? You kind of get free press from doing that type of thing. It's a good way to basically jump onto the distribution that the other front has. Do you?”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“No. We were working on multiplayer a long time ago. I think one of the things that's interesting about our company is we started with the hardest customers and we did the same thing actually on the in-house side too. So like we had bank customers a while ago and the security and permissioning systems that you need to build for a bank are so much more in-depth and like the enterprise readiness than for a lot of the other folks. And the biggest problem with multiplayer and the way that we're doing it is we're allowing the in-house side to kick it off or the law firm side. And to do that, the security and permissioning that you needed in place for both is astronomically high. So we were working on this like a very, very long time. We were on it for like six months to almost a year. We just did all the permissioning and all of that stuff first before you do kind of the UI on top.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“And we actually haven't built many features for tax compliance and procurement, right? Starting to happen is those departments are adopting Harvey. Even though we haven't built features specifically for those departments, the reason why is the legal department actually interacts and just like legal documents are such a core part of a business that they interact with all of these different parts of the business, right? And so we've released basically a feature that's multiplayer. It's called shared spaces. At first, like a lot of the impetus for doing it was you want a large corporate, like a Walmart or whatever, to work with our law firms in the same platform. And that's happening. But actually what's starting to happen is these corporates are using the legal team is working with the compliance department is working with HR, is working with everything else, all in Harvey at the same time.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Think like three to five years until we see massive, massive productivity gangs and enterprise. I think the capabilities are there already. The capabilities were there two years ago. A lot of this is like if you think about just like the average enterprise workflow, there's like 17 different systems they're pulling data from to get that workflow done. Like literally 17 might be on the low end. Sometimes it's like 50 and you have 100 tabs opening. You're opening in all these different apps and they kind of connect to each other. They don't really connect to each other, right? And so the long tail on actually getting these systems and agents to do a task from start to finish is so difficult. And the problem that you're going to end up happening is you have these vertical companies building vertical agents like us and Sierra, et cetera. But a lot of even the verticals connect to all of the other parts of the enterprise. So like one thing that's happening that's interesting for us is a lot of our revenue is starting to come from Global 2000 or Fortune 500 companies.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Huge companies. The other thing that I feel like folks don't realize is everything could pause. Like both of those companies could stop developing things right now and the amount of saturation of AI that would just happen to the economy would still skyrocket. Like we're so far from just the ability of the models right now being integrated into daily life. People do not know how to use these systems. Like consumers don't, they don't. And business is definitely don't. And there's so much of the capability overhang is so high. Like I think it's higher than anyone who's even talking about. It's astronomical. And so I think if both companies literally just stopped shipping things, their revenues would still explode because there are going to be so many companies building on top of their models. There are going to be so many different parts of the economy that adopt these things that I think we're”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the main thing with OpenAI is they have so much consumer brand. It is so powerful, and especially outside of X and outside of kind of like our worlds. It is so unbelievably powerful. And I don't come from the tech world. And so all of my friends, all of my relationships before this were outside of tech. That brand power is incredibly powerful. And I think more focus on consumer and just tripling down on that, that I think is where I'd be the most bullish. I think that on the enterprise side, there will be multiple winners. Like enterprises don't allow there to be one winner, right? So no matter what, there's going to be OpenAI is going to get some of the enterprise market anthropics going to get some of the enterprise market, but the consumer market, I do think OpenAI has an opportunity to take a lot of this. And obviously the main competitor there is going to be Google. But I think they both can be just astronomical.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the slope will only increase. I think that it will get better and better and better. And I think that will unlock a lot of productivity just across the entire world.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“I think that we're seeing a plateau in performance for consumer use cases. And the reason why I think this is a misnomer or something that people actually shouldn't pay attention to is we don't need them to be better for consumer use cases. I feel like this is something that folks don't quite understand is like a lot of the consumer use cases like we're done. You don't need better reasoning to solve these problems. What you need is like different contexts. You need to connect to your calendar. You need to connect to all of the different apps that you use and things like that. That's what an increase in performance is for them. There might be a plateau in some of the consumer facing side of things. On the enterprise, I think things are going to keep going and especially Cogen. I think we are not going to see a plateau in Cogen. I think that is going to get much better really, really fast.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“We aren't routing the majority yet, but even if we were, there's no conflict. Basically, like they want us to win and they want us to use the best model, right? There's nothing in our agreement or our relationship or anything like that that you have to use OpenAI models. And if anything, I think that for them, like getting the feedback from application layer companies on this is where your models aren't doing as well. This is where your models perform super well. And this is where you need to improve is super valuable to them.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Not entirely, but there were definitely, so we route basically based off of the use case, we route to the best combination of models, and definitely our traffic went up to Opus 4.5 significantly.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“I think just moving fast enough on product, that is always, I think, the biggest existential threat for all the application layer companies. And it's not necessarily that Anthropic or OpenAI or tomorrow going to put 50% of their resources after the legal vertical or tax vertical or anything like that, but they're just improving their product and models. And the value of your product is going to go down unless there is a massive delta between what your product does and what you could get from an enterprise GPT license, right? And so it's just a constant existential threat of how do you make sure you get to escape velocity on product so you have enough of a product mode for them to not run you over. And I think about that daily. When I'm thinking about competitors, the main thing I think about is just I'm more bullish on these labs than most people, I think. I mean, a lot of people are. I'm very bullish. They have incredible talent. And I think more...”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Once you're inside your day to day could be crazy, and you could be thinking you're not doing very well. So I actually think it matters a lot. People just don't realize that because they aren't inside of these companies. They're on the outside.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Constantly, like 24 7. How many times a day do you think we feel like there's an existential threat? The big model providers are going to release something and maybe we haven't released something all the time. Like startups are very difficult places to work. And so you think of like from the outside, oh, wow, they're like growing revenue so much they're the category leader. They have all these investors, et cetera, et cetera, right? GRR is high, all these things, right? But internally at all of these companies, it's chaos. And it goes up and morale goes up and down. You face really difficult things. And then you have to figure out how to get through them. Being a missionary really does matter because the reality is once you're on the inside, the brand of the company and the success of the company matters less than when you're on the outside. It matters a lot on the outside because people looking in are like, oh my God, that's the most successful. It's super well run, all these things.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“First place because the people that think or go to a company because of the investors usually don't care that much about the mission of the company. And so my point with all of these things is there might be like some short-term games of perception mattering. In the long run, it doesn't matter at all because if you make all of the wrong decisions, nothing matters. It might help you with recruiting them.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Someone like EQT actually gives you that more than Silicon Valley because they're private equity and a lot more lawyers know who that is, etc. So I don't really believe in those two. The third one might be the one area that it is helpful, and that's just recruiting. Humans are very bad at judging how good other humans are. We're really bad at it. Like we're really bad at it. And I can tell you a very clear reason for why we're bad at it. We still pay so much attention to someone's resume. We care so much where they went to school, and this happens so much in technology. It happens a lot in tech. The only other area where I know it happens an incredible amount is legal. Legal in tech are probably two of the main ones where prestige matters where you went to school matters, how your grades were, who you worked under, things like that, right? It does help you in a sense of if you get one of those brands, people assume that there's maybe a higher chance of the company being successful. The reality is that might be the wrong person to hire in the”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“The benefit of mindset is like, no. That happens too. Yeah. Oh, yeah, sure. Yeah, I mean, I'll give you one example in our vertical. The vast majority of our customers don't know who Sequoia A16Z or any of those people even are. And so I think that maybe there's a couple ways that people think about keymaking. One, they think of keymaking as it provides you with more capital. More capital does not mean you run a better business. You could have as much capital in the world as you want if you make the wrong product decisions. You're just going to invest in all the wrong places and it doesn't matter. It's the same as VC. You have a hundred billion and if you put it all into the wrong things, that still goes to zero, right? So I don't think capital makes folks win. The area where kingmaking, or like people think kingmaking matters, is customers, where they basically say, hey, this has branded trust. And so that is good. I think there is a little bit of legitimacy there, but it's not only the top three VCs give you that brand, right? A vast majority of VCs give you that brand. And what's actually interesting for us is like,”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“And they have an incredible background. And I'll be like, that person didn't seem very good. And it was just like my gut. And I think I've been right in some of those instances. And I've bet on people that sometimes they say that I shouldn't have bet on and they've turned out right. So when to hire execs, I've probably been wrong the majority of the time who to hire, I think I've actually been right a decent amount of times.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it really depends on who you get. I'll give you an example of something that I haven't trusted BCs as much with. And I think I've been right in some instances, wrong in others, is hiring. The areas I've been wrong the most in is when to hire a more senior exec. The VCs have been right. Like my partners are right. They've been right. I took too long to hire senior execs in some instances and it cost us problems. It created competitors when there shouldn't have been competitors, things like that. The thing that I think they've been wrong about is who to hire. And I think sometimes the problem that VCs have is they're managed up. They don't actually see inside a lot of these businesses. They see the board meetings. And so sometimes the person who presents really well at all the board meetings or something like that, they think of as that's a really good executive. And then that person gets a reputation for being a really good executive. I'm not from the tech world. I don't know any of these backgrounds. And so all sometimes get intro to someone from a view.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“In three months, we're going to do XYZ. And then you say, in six months, we're going to do XYZ. And then in nine months, we're going to do this. And at the end of the year, this is what's going to happen. And if those things come true, they start to really trust you and they start to believe you. And then when you go out to do that fundraising process, it can happen in 12 hours. You don't need to make tons of materials. You don't need to go out and do this massive, massive process. The problem with this is you are then not optimizing price. So that is assuming that you are not trying to optimize price. What you are trying to optimize is partner. It's much more targeted. You're basically targeting a group of people and you're saying, these are the people I want to work with and I want to gain their trust and then they'll invest in me versus I'm going into the market. I'm doing this massive competitive process.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the main thing about fundraising is you should always think of it as start it six months ahead of time and you will do much less work than if you actually go out and do the process. So what I mean by this is, and I learned this from some other founders who are really good at this, is what they do is they try to basically get folks to come in for a couple million dollars, like just like one or two. And you give them information rights. So you say, here, like, we're going to tell you how we're doing. And what you do with that is now they can check on the business, right? And the most important thing at least that I have found, I think VCs care about this the most, and hopefully they do, because this would be a good thing if they do. I'll tell you, is trusting that when a founder says something's going to happen, it's going to happen. And if you do that over enough times, hopefully VCs really trust you. And so going back to that strategy, if you let them invest a little bit in the beginning, and then you say, hey,”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Was 1.5 is what we were valued at, and our revenue was definitely lower. I think maybe that was one of the ones that felt super high. The other ones haven't. Another thing too that I'm very picky with investors. So I don't spend tons of time fundraising, but I actually do is there's a couple investors that I've become decently close with. And when it's time to fundraise, usually we get preempted or I say, hey, I think it's like time to fundraise and I reach out to literally like one or two people. And so I plan my fundraises pretty far in advance. So I'll basically be like, I know who I want to lead the next fundraise. My point here is we almost every single time we probably could have gotten much higher valuations than we took. And instead, we chose the best investors and the ones that I trusted and personally wanted to work with.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Feels more reasonable. Feels fine What happened at Series A. You felt the most uncomfortable high. Yeah, I think maybe the Series C felt very high. What was that?”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“In the next couple of years, in a lot of these spaces. And so you really have to at all times make sure that the company doesn't go, wow, I did a really good job, chest bump, head pat, like we're done, right? You have to instill this, yeah, well, anthropic, you know, 10x and they started at XYZ billions of revenue this year.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, yeah. So it was funny. This is, I think it was our offsite in 2024. And I remember we kicked off 2025. And the first thing I did is go up and I said, hey, we had a good year, but I'm pretty sure Anthropics at like $3 billion in revenue right now, right? My point is the entire market is massive right now. And I don't mean just like legal AI market. The AI market is exploding. And so I think you have to, when you are a leader of a company like this, one of the biggest jobs that you have is to make sure that your team doesn't feel like they've already won. Because the reality is the market pull is massive. And so sometimes your success isn't just your execution. It's the market pull. And so you have to benchmark yourself against other folks in the market and not just legal AI companies, but actually just AI adoption, right? I also think that we're just on an insanely compressed timeline. Like I think the winners and losers are going to be decided.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Again, where it's like what I spend a lot of my time on is what is the direction of our company and our product for the next six months, year, et cetera? And now you can start thinking like that.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah 100%. And I think it's also a testament to something else, which is these companies are growing so much faster than they used to. It's very important to go through a couple stages, basically. Like I see stage one as product market fit. Stage two is like company market fit. In other words, like have you created the structures of your company that are the same as traditional B2B SaaS or whatever consumer SaaS, whatever you're doing? And what's different? And there are differences. And any VC who says that there are no differences at this point hopefully has changed their mind. There are differences. And it's different based off of what vertical and which company you're trying to build. So you have your product market fit, then you have company market fit. And then do you know what? You want to go right back to reinventing product market fit again, right? And so it feels like there's a cycle of doing that. And I think for us and like me personally, some of our first couple years was product market fit. Last year was company market fit. I'm back to product market fit.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“One of the ones I have that I think was a good habit in the beginning of the company is now and now is starting to get bad, is I zero out Slack like every like 15 minutes and so I'm in like almost every single Slack channel and I read every single thing. It was really good in the beginning of the company because if you do that constantly you're basically every day all you have to do is catch up compared to what happened yesterday. And so it's really easy to make decisions. The problem with that is I've probably done that for too long. As you scale, you actually have to focus more and more on what is the P0. And I think I've done a little bit too.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“What would yours be? I think it's getting up early. We're in 60 countries now. And so no matter what, I try to keep basically East Coast time. So when I'm in San Francisco, I'll get up at like 4 a.m. or 4.30 a.m. And what that allows you to do is you can kind of like focus before the stream of slacks and the stream of emails come in. And I think that like a couple hours in the morning, especially when I can go to the gym and I can kind of think about like product and those things, that's changed the trajectory of how I operate the company more than anything else. And I do it when I travel too.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“It just reduces my stress for the rest of the day. And I've found that over time, a lot of company building is just making very good decisions. And if you start your day off with basically something that is very challenging in a physical way, you kind of have this stress relief through the rest of your day. Your body has absorbed that stress. And I very much believe that and everything else too. Like I try to do a stressful thing every week because I think a lot of it is like stress tolerance over time.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so I played sports when I was in high school and then didn't as much when I was in college. And when you start a startup, things get pretty stressful. And I had a mentor who gave me advice of basically like, hey, stop lifting so many weights and start trying to run a mile. And I remember when I started running a mile, I think I was at like eight minutes or something. It was really, really bad. I was like pretty out of shape. And I had basically a goal to get up every single morning and just reduce my mile time as fast as possible. And the way that I did it is I'm going to run one mile no matter what. And then just kind of see if I can reduce the back end of the mile again down, down, down, down, down until I can get to as fast as I possibly can. And the outcome of that, which I think really helped, was, and something I'm actually trying to do more and more in my life, is every morning when I wake up, I get up pretty early and I just try to destroy myself and run as fast as I possibly can.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I know. If Pat's listening, he definitely needs to give some credit to Sarah here. Yeah, Sarah actually was, so our first investor was OpenAI. And then our first two Angel investors were Sarah Guau and Alad Gill.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
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2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
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2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
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2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
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2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the value of B2B SaaS is about to become astronomical. I think that we're seeing a plateau in performance for consumer use cases. Probably what's going to happen is the economy's going to explode. I think a lot of people in deals, they think that movement is action, natural. The second piece is know when to not negotiate. There are certain deals where you want one thing from the deal and nothing else matters. If you want to hire somebody, hire them whatever they want to be hired and put them in the position that they want.”
2026-01-19 · The Twenty Minute VC · 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg · IDENTIFIED FROM THE TRANSCRIPT · source