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

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“100% that, and I think we've done a good job of creating all the features. But now I want to combine all of them together so we can get to that 75% DAU over MAU. That is how you really show that you've created something that's integral to the industry.”
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 mean, we obviously have revenue targets and things like that, but what I want to switch from is a productivity software that is like a nice to have closer to an operating system that is pretty much crucial to the industry. And so it's more how do we, we built a lot of different features across the board, right? We very much, like in Parker Conrad's voice, like built a compound startup, like very much, we haven't tied it all together yet. We've done a really good job of creating all the pieces, hasn't tied together. Maybe an interesting stat on this is our DAU over MAU for people that use four plus product lines is 74%. That's like slack level, right? Slack was like 80 or something like that. It's incredibly high. The percentage of people that have used 4 plus products is very low. And it's doubling every quarter. But what I really want to care about next year is can we make this 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
“I'm always respected Founders Fund. Like, I've always really, really respected them. I've respected the hell out of their companies too and a lot of their founders. I just, I respect them a lot. And we haven't ever worked with 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
“Yeah, yeah, yeah. No, I think that's right. It should feel painful. It really should. And I didn't do that in the beginning. I was like, oh, we'll just do everything, whatever. And I think having said that, I do think you can do more. And I think you can be very ambitious, but you do have to strike a balance between the two.”
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 have Brian Halligan's on there, and his is no. It's just the word no. And one of the things he's been incredibly influential and helpful to me. And one of the things I had a problem with is just like saying no to things. And it's a huge, huge problem as you scale as a founder of figuring out an ability to actually block off time for yourself and to say, no, this is my priority. I'm saying no to everything else, right? And it's the same with, this is also probably one of the main things that hopefully I've improved on product is I used to every quarter just be like, and there's a P0. And then also, there's a P00. And then there's this and this and this, right? And I've started to be a lot more disciplined and try to be disciplined with my team.”
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 didn't even see that. I mean, but it's interesting. I think Pat also has this too, and all of my VCs do, and in particular, he really thinks of just constant, like a relentless application of force is what he says. And that's actually what I have next to his name. That's incredibly important. And I think that if you lose that as a company, the company is pretty much over. I think that you as a founder need to constantly, constantly be applying force. And it starts with applying force to yourself. And if you aren't applying force to yourself, you don't have that ownership mentality and you'll start to get weak. And I think that will trickle down through the rest of the company.”
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
“Stressed. It's compounding, like massively compounding for you as an individual to just put yourself through that stress.”
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
“You knew them coming in. Yeah, definitely. Yeah, definitely. I mean, I'm always nervous. And I think one thing, too, I think I said this earlier, but I think Keith Raboy says this, who I've actually never met in person. There's a couple people, I have a list actually at the top of my doc. I have like an operating doc. And I have a list of people and they all have like two words next to them. And it's like the thing that I've learned from them or something like that. One of the things I think he was talking about at some point is like how important it is that you should be constantly stressed, like constantly stressed and do things that make you stressed every day. I strongly agree with that, like really agree with that. Like, I think the times that I've staggered or the company has stagnated is every day I don't have something that's like really stressful. The weeks that I do the best work or feel like I did the best work is every single like night before I go to bed, I'm like, oh shit. Like I have like tomorrow is going to be there's so many things. Everything needs to go right. I'm really.”
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 think that there's obviously a difference in scale, right? Like A16Z is just a lot bigger. I would say that A16Z is also louder. And so they're a little bit more in these other regions and other areas and things like that. Whereas Sequoia is, you know, it's just a different style, right? It's closer to, there aren't as many partners and things 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
“Half of the company basically is how much of a lot of the company building is actually the same. And I probably should have listened to people a little bit more about 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
“No, I think the pretexting affected. That was the worst one. So, I said earlier that a lot of company building has changed. I actually think a lot of it remains the same. And so there's a lot of kind of just like core first principles of scaling a company that I am much more focused on, that I wasn't focused on in the beginning. I'll give you the dumbest example ever. For the first like two years of the company, when I was doing like revenue projections, I never, and this is embarrassing, really embarrassing, I never was like, huh, if I want to hit this amount of net new ARR, you need to hire this many AEs at this quota, and this is how long it takes to ramp them. So you need to hire them at this point before you do that. I'm dead serious. Like, I never even thought about that, right? And it's these really core laws of physics about companies that remains the same. Like, there's no difference in AI. And I think in the past maybe, what have I learned in the past 12 months? Maybe it's more, what have I learned in the past, like 18?”
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 there was one where the person was quite literally on their phone. It was a Zoom and they were on the phone the entire time during the pitch. Did not even make eye contact. Literally, zero.”
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 don't remember what the post actually was, but the pre investment was like $4 million or something like that. And anyway, what happened at the series A was we went and met with basically like, I think it was like 10 VCs or something like that in like 48 hours, right? And I quite literally did not know who the VCs were. Like I didn't know. Like my co-founder was from tech and he knew and he basically gave me advice and things like that. So I actually think I had a weirdly unique view of the VCs because my entire judgment of them was just how that first meeting went. Like I didn't know that like Sequoia was in this tier and this one was in this tier and whatever. I didn't know any of that. I didn't even know who they were.”
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 everything about every one of them. Now I do, but back then, I didn't know anything. I didn't even have friends in tech. And so when we did, we did our seed and we didn't go to anybody else. It was just OpenAI. And then for our series A,”
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
“Pitch is a partnership. Yes, I had a weird thing where I didn't know who any of these guys were. And so when we were doing our series.”
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 went well. We had a call with Jason first and just kind of talked about what is our strategy as a company and what would we build. And then we had a final pitch to kind of the rest of the OpenAI C suite actually the morning of July 4th, 2022. Yeah, it was like 11 a.m. on July 4th and we did a pitch to the rest of the company.”
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 it wasn't a cold call. We cold emailed them. And we cobbled all that together, and we just sent a cold email to Sam Altman and Jason Kwan. The idea was basically, hey, did you guys know that at this point it was GPT-3 and just the API was public, I think the end of 2021 or beginning of 2022, they had an API. Did you know it was this good at legal? That was it. That was basically the subject line of the email was like, did you know it was this good illegal? And we met them like pretty recently after 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
“It won't be. It's possible. I think one of the things that I've done wrong in the past is I think that I have thought that someone couldn't scale because they have bad communication skills. And I've misread that. And then I didn't realize how easy it would be for them to learn how to do it. I think that sometimes because I feel like I do a lot of in-person interviews and a lot of those things, that sometimes I also end up making them stake of reading too much on the surface and not going deep enough. I think I've gotten better at it, but that's one of the things that I've done with hiring is I've fallen for the resume trap too. Like I've definitely fallen for it. And I think that's a huge mistake.”
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
“They With hiring, this is a huge mistake that people make, massive mistake. If you want to hire somebody, hire them whatever they want to be hired, and put them in the position that they want. If they're best in class, if you can't tell if they're best in class is a separate problem, but don't go back and forth. It doesn't matter.”
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
“Those ropes allow you to pull more ropes. And that's a lot of how I think about deal making. I think another company that has done an incredible job of this is Microsoft. Incredible job. They've created this partnership ecosystem, right? A lot of people have given them a lot of flack of like, why do you let people do XYZ partnership? Why do you let people build on this? They're just going to take it. And it's very clear that Microsoft has actually won in a lot of areas because they've decided to partner with kind of everyone instead of saying, ah, no, brass tacks, we're going to be very tough on 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
“There's just certain deals that we've struck where I wanted one thing in the deal, and maybe the financial part of the deal or something else about the deal, like my CFO or my VCs were like, oh my God, don't agree to that. Like do X, Y, Z. And I knew that if we signed it and we got the particular thing that I wanted from that deal, it would help our company to such a degree that it would help close another deal or it helped do something else. Like a lot of what you're doing, I think like the very good deal makers, and I think Sam Altman is incredible at this, is you're holding multiple ropes and you can kind of think of it as like you have like 17 ropes in this hand, you have 17 ropes in this hand, you're grabbing all these ropes. And at some point, you're going to get like pulled apart because it's just too much pressure and you're going to lose, right? And what you do is you get good at tying off one of the ropes. And then that pressure's gone and you have one tide. And then you tie another one and then you tie another one and you tie another one.”
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
“This, I think, is actually really, really important. And the best deal makers I know are very good at this, which is there are certain deals where you want one thing from the deal and nothing else matters. This only works when you understand the value of something more than everyone else does. And if you understand the value of something more than everyone else does, throw all of your principal deal making and you're supposed to negotiate X and then Y, and then it'll be 50% in between and all of that. That's all bullshit. Throw that aside and get the thing that you know is more valuable than anybody else does, done. The best dealmakers I know, like the best, they know that very well.”
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
“Another one Perfect. Maybe two pieces of advice. One is listen more than you speak, and it's very, very dumb, but it's true. I think a lot of people in deals, they think that movement is action. So they think that movement is progressing the deal forward. And they think that if they talk the most, they're in control of the deal. Not true. In the same way that in conversations, just because someone isn't participating in that conversation doesn't mean that they aren't listening, it doesn't mean that they have maybe the upper hand or something like that, right? And so I think listening is really important. And I see a lot of folks think of deal making as like chest forward. And if I'm the loudest and I'm saying the most, the reality is all deal making is just people reading. That's it. And it's people reading at scale. So it's people reading a one-on-one conversation and then it's reading groups of people and then it's reading entire verticals of people, et cetera, and it's figuring out what they want. The second piece is know when to not neglect.”
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
“Of a lot of these companies haven't hired any AI talent. And a lot of what they've done is kind of the model is basically the entire product. And as these companies scale and they have to create more differentiated products, I think having AI talent is going to matter again. And we're just getting, just now getting to the size of the company where we can hire the people that we need to kind of do a lot of that frontier work.”
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, it's incredibly, very high. And one thing maybe to bring up is I think that over time, we have this interesting thing where it's like a lot of the AI companies, application layer companies, including ourselves, like in the beginning were like wrappers, right? And what's going to happen over time is these companies are going to do two things. One, a lot of just the core software that they build. It's not even going to be AI related. It's just core software building. And that's actually going to be much very differentiated. The second thing that's going to happen is none of these companies have access to proprietary data until very recently. And so a lot of the stuff that we're looking at is how do you actually create custom solutions for a large enterprise? And that is AI problems again, right? So now we're all the way back to AI actually mattering. And I think that what we're going to see is that kind of main problem.”
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 think there's a combination of things. I think the reality is what researchers care the most about is working on really hard and interesting problems. And I don't say that as like bullshit. Like I think that there are sometimes to your point of like people just want to join hot companies. A lot of tech I think is like people just want to join hot companies. Researchers really genuinely do care about pushing research forward. And I think what ends up happening sometimes is the leaders at some of 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
“I would do is you can use the researchers to pinpoint who is the best researcher. So, in other words, if you ask a bunch of the researchers, not other VCs, ask a bunch of the researchers, who do they respect the most? They have such a tight-knit community and it's all merit-based. Like I'll tell you a group of people who do not manage up, AI researchers. That is not what they do at all. For better or for worse. And because of that, if you ask that community who are the best folks, they will triangulate for you and they will help you find. And usually it's not the loudest. They aren't necessarily the most famous, et cetera. It's not 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
“I don't think you can. That, I think, is actually a pretty big disconnect. The researcher community knows. So this is a huge disconnect between VCs, I think, and the researcher community.”
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
“This is the same thing. But look at That's good. This also, I forgot who tweeted this, I don't remember who it was, but this was like end of 2022. And it was like right after the chat GPT launch. And someone, I forget which VC did this, so sorry for not giving credit to them. But they basically tweeted, my prediction is what's going to happen is a lot of VCs, because they don't understand the AI ecosystem, they're going to revert back to looking at resumes because they don't understand. And this is what people do. When there are situations of chaos and folks don't know what's going on, the safest thing is to go look at other social signals to make decisions instead of using your own gut. And so I think that that's happening a lot in AI. And hopefully as the markets mature, this stops happening. But there's a lot of, I don't really understand this. And so what I'm going to do is look at the resume or look at a logo or look at 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
“Championship. As long as they're the one that scores the most points. Those are the exact type of people that I do not want to work with. I want to work with people that do care about how many points they've scored, but they care about that because they helped win the game, right? And I think that's a huge problem in tech is we have too many people that it's me, me, me, me, me, and not company, company company.”
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 think my trust issues, I mean, I think part stuff is hard to tell whether it's like nature or nurture, right? But I think that I definitely had some problems with authority when I was younger. And I had not the normal Silicon Valley kind of background in upbringing. And because of that, I think that I had to, I really went out on my own at a pretty young age and was pretty independent. One thing that you have to learn when you're leading a company is you are a leader and you are a partner to the rest of your team. It is not just you. Like I am not Harvey. Like Harvey is not me. Like it is a group of people that are building this company. And I think that sometimes what founders can end up doing is they can start basically saying like, I want to be the number one. I think this is like a sports team. There are people I know that they don't care about winning the championship. They want to be the person who scored the most points. And they're okay with losing.”
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, like, I would actually, if I had interviewed myself and I saw that as the way that I answered, the way that I would push on this is I would say, why do you do that? Like, why do you do that? And my genuine answer to that would be I have trust issues. Like, I have trust issues. Like, it is hard for me to trust that somebody else is going to handle that problem. And now all of a sudden, it actually is ownership. That is like an actual problem of being a leader. Like, you cannot scale a really good company and get to tens of billions of revenue if you have constant trust issues and you can't trust other leadership.”
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, and it's just all over the place. Yeah, exactly, right? It was Johnny here last. Here's Johnny, and I don't know. And I have found that there are a lot of people in tech that have done a really good job managing up. They have written a wave of their team success without being successful themselves. So the thing that I look for a lot is can people admit their mistakes? It is so obvious when someone is actually admitting mistakes versus they're saying that one of the biggest things they've done wrong is actually like something that's really great. We'll go back to something you said earlier. Like when you said some of the things are bad habits that you're trying to, well, I mean, yeah.”
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
“Mm-hmm. That's a good one. You definitely need to be obsessed. So, obsession is definitely very important. But the one that I look for right now a lot is ownership. And there's a bunch of different ways that you can assess this, but you do over time, you start to be able to just read if someone actually can take ownership over something or not. And the reason this becomes really important is as you scale as a company, it becomes really hard to figure out where a problem is stemming from. It becomes hard. This is how this ends up going, is it used to be I knew every single thing that was going on at a company and I can just be like, hey, that's where the problem is. I'm going to unblock that, right? Now we're getting to the point where I know most of what's going on at the company, but sometimes something is like so low down that I don't know what the problem is. And if I ask five people, they'll all do this. It's like the Spider-Man.”
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
“UK lawyers work insanely hard. And so it might be that I don't notice it as much because the domain that we're in, they work the same across the globe. Like lawyers are just incredibly disciplined hardworking 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
“Yeah, it's just really hard to hire people. And so that was just kind of interesting to me or something that I wasn't used to. Whereas in the States, you can hire someone and they start quite literally like the next day sometimes like literally. Or if they have to give two weeks notice, they start exactly two weeks later. That allows you to be a little bit more just, I quickly need to hire this retroactively, I can fix a problem. In Europe, you have to plan out more. And so we've done a lot of really big office openings. Like we just announced Paris and Dublin and a bunch of other ones. But you have to just think about this stuff at like a longer time horizon. You can't do it instantaneously.”
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's not a difference in talent. It just takes a long time to hire people. And so you have to just think about it with a way, way longer time horizon.”
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
“Oh, I think it's similar in Europe to where it is in a lot of places, which is you don't want to go into a country or a domain or anything like that and act like you know how to do something, right? Like you really need to partner with an industry or you need to partner with a geography, right? And when I say we should have invested more in that, it's more like we didn't invest in it that much in 2023 and 2024. We invested tons last year and we're investing even more this year. And the difference is pretty massive. The difference in kind of the quality of our team last year and the partnerships and things like that and how our product is localized for each geo is just a huge difference. But you can't do this from sitting in San Francisco and like kind of thinking about how to do it. You got to travel.”
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
“Viewers ask, but maybe I'm just a shit interviewer at this stage, to be honest. Of the X fear I don't think it'll be this year. I think there will be bumps. I definitely think we will have more moments like the deep seek moment where everyone freaks out, right? And I think we're close enough to an edge of, you know, if enough people say that there's going to be a bust, it's pretty easy for one thing to happen and for everyone to freak out and there to be a bust and it's a self-fulfilling prophecy. Those are usually like pretty short. I think that we will have a bunch of short ones, but I think long-term AI is going to completely reshape every part of the economy. Like I very strongly believe 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
“The same as GDP. One way to think about this is most professional services is cyclical. So if you have a really good year, professional services have a really good year. That's almost always how it works. Other than bankruptcy and litigation is somewhat counter-cyclical. It depends on the area. And so I think people think about this and they're like, oh, wow, like AI is going to impact legal and it's going to just destroy all these jobs. The thing they aren't thinking about is all of their customers are using AI to create more products. What happens when you create more products? You need more product legal advice. What happens when you're expanding into other countries faster? What do you need? Regulatory advice, right? And so I think people are thinking about AI in all of these industries as like a vacuum. And the reality is you should think about AI as like the entire economy what's going to happen. And probably what's going to happen is the economy is going to explode. These companies are going to have crazy expectations for what they can do. And the professional service”
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 had a conversation with a pretty large private equity shop recently, and they were talking about their year is going to be incredible. They think it's going to be like a big M&A year. It's going to be great. And they were talking about how they think about legal fees. And the way that they thought about legal fees is the reality is it's going to be a big year. And whenever we have a big year, we pay more in legal fees. That's just like how it happens, right? But there are certain things I don't want to pay for anymore. Like there are certain parts of the deal, et cetera, that I just marking up NDA is whatever it is. I don't want to pay for that anymore. But there's all these new things that I'm paying law firms for. AI risk. Like, should you buy this company? Is there a problem in XYZ country with an act or something like that that's going to change it? There's so many new pieces of work for professional services that my gut is that's not what's going to happen. In fact, I think what's going to happen is the professional services market is going to actually keep growing.”
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
“Something like that. I mean, if you just look at the breakdown of how many lawyers exist on Earth and how many of them are at companies versus in-house, that's pretty much the same. In five years' time, what will happen?”
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
“Right now, so you mean corporate versus law firm? Yeah. I think it's around 40% of our revenue is in house, corporate and 60% is law firm, something 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
“No, no. And I think that's what's really interesting about our business that we're doing for like a corporate is not the work that our law firm customers are doing. It's like alternative legal service providers. It's this lower end work. What position?”
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 there are a couple companies that have basically said that the Harvey budget comes out of their spend on professional services, not out of their tech budget. The budget for professional services is in the billions a year versus the tech budget for that GNA group is astronomically smaller.”
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 think that's not at least an arm vertical what I've seen. I think there are a lot of areas where we are going to start moving to consumption-based pricing. At least for us, for our customer base, that would be completely fine with 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
“Yeah, I mean, there's a third one that now develops, which is these AI products are so powerful, and I think over time, the ROI is so high that your ROI can become so massive that it's less of a hostage and it's maybe closer to how Palantir thinks about things. In other words, the more value that you create for the customer, the higher you get paid. And I think that more and more companies are going to start aligning to that. And the reason why is I'll do the law firm side and I'll do the in-house side. For law firms, they bill by the hour. And so a lot of people are like, how could you ever sell to them? There's no way that this is going to work, right? Two things might happen. One, they might switch to fixed fees. Well, now we're good to go and efficiency is really good. I don't think it's going to happen that fast. The second thing that actually is happening, and we have so many law firm customers that have gained new business by building something custom in Harvey and saying, we'll do 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
“And I think a lot of these enterprise companies should start thinking about their company that way, in the sense of like, sure, there's some of a land grab right now, but really what's going to matter is if you are bullish on AI, you should be bullish on your product, the value of your product. Like we are in day one of product development. Like it's going to change astronomically. And so it's more important than landing new customers and getting really higher is can you retain those customers? Because that customer that pays you a million today, there's a real world in which they pay you 100 million at some point. I think Databricks is a company that's done an incredible job of 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
“Agree. And I think that what that requires then is going back to what we were saying, which is you go product market fit and then how do you get company market fit? And that's actually like how you structure your company. And I think part of that is different than how it used to be in the past, where if you have long implementation cycles or one thing that is going to end up happening, I think, is a lot of these verticals are going to land at a big fortune one or Fortune 2 or whatever, right? And their product is going to expand massively. This is a really interesting thing about Microsoft. I don't know how much you know about Microsoft Salesforce, but they started in the beginning and the vast majority of their sellers, it was pre-sales, right? So spear fishermen. Like you have tons of that, right? Old school spear fishermen. And they actually eventually migrated to a lot of what they have as post sales, like a lot of their investment is actually in post sales. And the reason why is because their customers just, their NDR goes up, up, up, up, up, up. They keep buying more things. They buy more compute.”
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 I would tell them actually is your GRR matters. And I think one thing that a lot of investors in the AI space have been not paying attention to is GRR. They've been basically just looking at net new ARR and kind of being like, ah, churn is fine because they're going so fast that maybe they'll pivot or they have some customers. I think that's a huge mistake. You're going to see a lot of companies in a lot of verticals that go really, really fast to signing a bunch of customers because maybe there was only one in the vertical and now there's a second player, et cetera. But then they have to actually support all of those customers. And if you don't have the infrastructure in place and you make a bunch of promises up front, and then all of that falls down, you'll start losing customers really, really fast. And I see a lot of AI companies not focusing on this. And I think that's going to be like a huge reckoning for folks once they get past 100 millionaire arms.”
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