Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady

Winston Weinberg 0:00 I think the value of B2B SaaS is about to become astronomical.

Harry Stebbings 0:04 Do you think we're seeing a plateauing in performance across the different model providers?

Winston Weinberg 0:09 I think that we're seeing a plateau in performance for consumer use cases. Probably what's gonna happen is the economy's gonna explode, these companies are gonna have crazy expectations for what they can do. I think a lot of people in deals, they think that movement is action. Not true. The second piece is know when to not negotiate. This, I think, is actually really, really important. There are certain deals where you want one thing from the deal and nothing else matters. If you wanna hire somebody, hire them, whatever they want, and put them in the position that they want. If you can't tell if they're best in class, that's a separate problem, but don't go back and forth.

Harry Stebbings 0:44 Were you nervous pitching to Mark and Ben?

Winston Weinberg 0:46 Um-

Harry Stebbings 0:47 You knew them coming in.

Winston Weinberg 0:48 Yeah, definitely.

Harry Stebbings 0:48 What existential threat today concerns you most? [upbeat music] Ready to go? Winston, dude, it is so good to finally meet in person. It's so great to have you in the studio. I've heard many great things for a while, because it was Sarah Guo that found you first, before Pat, I heard.

Winston Weinberg 1:18 Yeah, I know. If, if Pat's listening, uh, he definitely needs to give some credit to Sarah here. Yeah, Sarah actually was... So our f- our first investor was OpenAI, um, and then our first two angel investors were Sarah Guo and Elad Gil.

Harry Stebbings 1:31 Uh, dude, I, [chuckles] one, I love the way that under 30 seconds we've already done a sucker punch to Pat. [laughing]

Winston Weinberg 1:37 [laughing]

Harry Stebbings 1:38 But, but two, I, I just wanna start actually on something that shows a little bit about your character, and it was a story that Pat told me. He said, "Ask him about running a mile, the time that he did it first, and how that progressed, 'cause it's very revealing of his character." Can you tell me this story?

Winston Weinberg 1:55 Yeah, so I, I, I played sports when I was in high school, and then didn't as much when I was in college. And, you know, when you start a startup, things get pretty stressful. Uh, and I had a mentor who gave me advice of basically like, "Hey, stop lifting so many weights and, like, 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. [chuckles] It was really, really bad. I was, like, pretty out of shape. Um, 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 gonna 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. Um, and it... The, the outcome of that, which I think really helped, was, and, 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. It just reduces my stress for the rest of the day. And I've found that, like, 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 kind of, I don't know, very challenging in a physical way, you kind of, like, have this stress relief through the rest of your day. Your body has, like, absorbed that stress. And I very much believe that in everything else, too. Like, I try to do a stressful thing every, every week, because I think a lot of it is, like, stress tolerance over time.

Harry Stebbings 3:26 Can I ask, what decision have you made to your daily routine life that has had the biggest positive impact? So, like, one for me is, like, I drink a liter of water when I wake up-

Winston Weinberg 3:34 Yeah

Harry Stebbings 3:35 ... and it just makes me feel [chuckles] like I've accomplished something very quickly, and I'm hydrated fast.

Winston Weinberg 3:39 Yeah, yeah.

Harry Stebbings 3:39 What would yours be?

Winston Weinberg 3:40 I think it's getting up early. Um, it, it's helped a lot. I think, also, like, 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, 4:00 AM or 4:30 AM. 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, 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, like, changed the trajectory of how I operate the company more than anything else. And I do it when I travel,

Winston Weinberg 4:16 too.

Harry Stebbings 4:16 What bad habit do you have or do that you continue to do?

Winston Weinberg 4:21 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. And it was really good in the beginning of the company, because what you... 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, right? And I think I've done a little bit too much of, like, still being in every single Slack channel and checking every little thing. There was, um, there was a time I was talking to someone from Sequoia, and they had been living with other founders, uh, during COVID. And they said that what they... And these are very, two very famous founders. I'm not gonna say who they are. But, um, they were saying that- he, he was basically saying that a lot of their routine was, they would just jump into random meetings at the company. And what they were doing is they were basically checking, just to see, like, how does this department do this sales call? How does this, you know, part of product create their PRDs and, like, analyze their PRDs? How does this part of the company come up with OKRs or, like, metrics, right? And I remember I left that dinner, and my co-founder and I were like: "Wow, those guys, like, aren't working. Like, that's, like, so lazy," and all this stuff, right? And now, when I think about those guys, I say, "Wow, they are incredible. Like, they're... I get why they're some of the best founders on Earth," because they've created a machine where they have so many folks at the company that are doing a really good job, that they spend the majority of their time actually moving the machine. And you go back to being, "I can focus entirely on product. I can focus entirely on what the most important things are at the company are." And, like, that's really what I'm trying to do this year, is transition from kind of all those heroics to, can you build a really well-run machine?

Harry Stebbings 6:17 I think the really interesting part, actually, is that Andrew Bilecki at Klaviyo-

Winston Weinberg 6:20 Yeah, yeah

Harry Stebbings 6:21 ... uh, he, he made the decision to kinda go back to product-

Winston Weinberg 6:24 Yeah

Harry Stebbings 6:24 ... as a public company CEO and bring someone else in.... Is that just testament of the times that we're in, the importance of speed and product centricity, do you think?

Winston Weinberg 6:34 A hundred percent, and I think, I think it's also a testament to something else, which is these companies are growing so much faster than they used to, and so you have to get the me- Like, it's very important to go through a couple stages, basically. Like, I see, like, stage one as product-market fit, right? 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, you know, B2B SaaS or, 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, uh, 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, right? And so you have your product-market fit, then you have company-market fit, and then do you know what you wanna go right back to? Reinventing product-market fit again, right? And so it feels like there's a cycle of doing that. Um, and I think for us, and, like, me personally, like, some of our first, like, couple years was product-market fit. Then it was comp-- last year was company-market fit. I'm back to product-market fit again, where it's like, what I spend a lot of my time on is, like, what is the direction of our company and our product, specifically for the next six months, year, et cetera, and now you can start thinking like that.

Harry Stebbings 7:46 You're at a hundred and ninety of ARR you posted yesterday-

Winston Weinberg 7:49 Yeah

Harry Stebbings 7:49 ... and you raised it eight billion. Do you ever, um-- Do you and Gabe sit and think, "Gosh, that's quite a lot. I'm worried about scaling into that"? Do you sit and think, "Gosh, we're undervalued?" How did you analyse that?

Winston Weinberg 8:02 Yeah. Yeah, yeah. Um, so we... It was, it was funny. This is, um, I think it was our offsite in twenty twenty-four, and I remember we kicked off twenty twenty-five, and the first thing I did is go up and I said, "Hey, we had a good year, but I'm pretty sure Anthropic's at, like, three billion in revenue right now," right? Um, my, my point is, the entire market is massive right now, and I don't mean just, like, legal AI market. Like, the AI market is exploding, right? 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, right? Because the reality is the market pull is massive, and so sometimes your success isn't just your execution, it's the market pull, right? 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? Um, I also think that we're just on an insanely compressed timeline, right? Like, I think the winners and losers are gonna be decided in the next couple of years, right, um, 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 instil this: "Yeah, well, Anthropic, you know, ten X, and they started at X, Y, Z billions of revenue this year."

Harry Stebbings 9:25 Seven to fifty-five, and then fifty-five to one ninety, say, and then you're going one ninety to, uh... I'm a VC, so I can gasp, but, like, four hundred, four twenty, you're, like, two, two and a half X from that.

Winston Weinberg 9:38 Our goal is much, much higher than that, um, and I think we can do better than that this year.

Harry Stebbings 9:42 Okay, so let's say five hundred, and then I'm looking at that and I'm like: Okay, then the eight billion doesn't feel too much.

Winston Weinberg 9:49 Mm.

Harry Stebbings 9:49 'Cause I... The way that we think about it internally is, like, what's end-of-year revenue?

Winston Weinberg 9:52 Yeah.

Harry Stebbings 9:52 And then what's the multiple on that end-of-year revenue? And if it's, like, twenty to twenty-five, feels fine.

Winston Weinberg 9:58 Feels more reasonable-

Harry Stebbings 9:58 Feels fine

Winston Weinberg 9:59 ... or closer, probably.

Harry Stebbings 9:59 If it's a hundred, [laughing]

Winston Weinberg 10:01 [laughing]

Harry Stebbings 10:01 it feels iffy. Then welcome to Series A land.

Winston Weinberg 10:04 Yeah.

Harry Stebbings 10:04 That's what happens in Series A.

Winston Weinberg 10:05 Yeah.

Harry Stebbings 10:05 It's why it's a bad place to be investing. Okay, but you never got to a stage where you're like, "Oof, this valuation feels like we're gonna live into it, or we've got to grow too much into it." Which round felt the most uncomfortably high? [chuckles]

Winston Weinberg 10:15 Felt the most uncomfortable high? Yeah, I, I think maybe the, like, Series C felt very high. Uh-

Harry Stebbings 10:20 At-- What was that?

Winston Weinberg 10:21 I think, uh, we were... It was one point five, is what we were valued at, and our, our revenue was definitely lower. [laughing]

Harry Stebbings 10:29 [laughing]

Winston Weinberg 10:29 Um, lower. I think maybe that was one of the ones that, that felt super high. The other ones haven't... Uh, another thing, too, that I've-- I'm very picky with investors, so I don't spend tonnes of time fundraising. What 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," um, and I reach out to literally, like, one or two people.

Harry Stebbings 10:53 Yeah.

Winston Weinberg 10:54 Uh, and so I plan my fundraises pretty far in advance. So I'll basically be like... Like, I know who I want to lead the next fundraise. My point here is, we, almost every single time, you know, we probably could have gotten much higher valuations than we took. Um, and instead, we chose the best investors and the ones that I trusted and personally wanted to work with.

Harry Stebbings 11:14 What do you know now about fundraising that you think all founders should know?

Winston Weinberg 11:18 Yeah. Um, 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, right? So what I mean by this is, uh... 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 gonna tell you how we're doing," right? Um, 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, 'cause it would be a good thing if they do-

Harry Stebbings 12:02 I'll tell you

Winston Weinberg 12:02 ... is, is trusting that when the 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, uh, in three months, we're gonna do X, Y, Z"-... and then you say, "In six months, we're gonna do X, Y, Z, and then in nine months, we're gonna do this, and at the end of the year, this is what's gonna 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. It- 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're then not optimizing price, right? So that is assuming that you are not trying to optimize price. What you are trying to optimize is partner, right? It's much more targeted. You're basically targeting a f- group of people, and you're saying, "These are the people I wanna work with, and I wanna gain their trust, and then they'll invest in me," versus, "I'm going into the market, I'm doing this massive competitive process, and I wanna maximize price."

Harry Stebbings 13:06 Totally get that. Rory O'Driscoll at Scale, who's a phenomenal ultimate-

Winston Weinberg 13:10 Yeah.

Harry Stebbings 13:10 I love Rory, a dear friend of mine. He's like, "Har..." I'm not gonna... Fuck it, I might do the accent. "Harry, when someone- [chuckles] ... continuously hits plan, uh, give them more money, okay?" [laughing]

Winston Weinberg 13:20 That's good.

Harry Stebbings 13:21 And then that-

Winston Weinberg 13:21 No, that's a good one.

Harry Stebbings 13:22 That's it. It's, it's very simple.

Winston Weinberg 13:23 Yeah.

Harry Stebbings 13:23 Like, when people do what they said they'd do, generally, they will continue to do what they said-

Winston Weinberg 13:27 Yeah

Harry Stebbings 13:27 ... they would do. And, uh, I don't know if you're an angel in that many companies, but I, I'm an investor in 170. [chuckles] Very few do what they said

Harry Stebbings 13:35 they would do, and very few hit plan. Uh, so I totally get that. Do you actually believe that venture investors really move the needle?

Winston Weinberg 13:43 I think it really depends on who you get. I'll give you an e- an example of something that I haven't trusted VCs as much with-

Harry Stebbings 13:48 Right

Winston Weinberg 13:49 ... and I think I've been right in some instances, wrong in others, is hiring.

Harry Stebbings 13:52 Mm.

Winston Weinberg 13:53 So, um, the, 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're- 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, right? 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, right? Like, they don't actually see inside a lot of these businesses. They see the board meetings, right? And so sometimes the person who, like, presents really well at all the board meetings or something like that, they think of as, "That's a really good executive," right? And then that person gets a reputation for being a really good rep, rep... yeah, executive. I'm not from the tech world. I don't know any of these backgrounds, right? And so I'll sometimes get introed to someone from a VC, and they have, like, an incredible background. And I'll be like, "That person didn't seem very good," and it's just, like, my gut, right? Um, and I think I've been right in some of those instances, and I've bet on people that sometimes they said that I shouldn't have bet on, and they've turned out right. So when to hire execs, com- 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.

Harry Stebbings 15:10 I think, actually, it's a really smart distinction. I'm generally always wrong on who I suggest to my founders. [laughing]

Winston Weinberg 15:16 [laughing] Fair.

Harry Stebbings 15:16 And the benefit of hindsight, it's like-

Winston Weinberg 15:18 Yeah

Harry Stebbings 15:18 ... "Nah, that wasn't a good one." Often, we just bring in people that are actually too senior for the p- position, actually.

Winston Weinberg 15:22 That, that happens, too. Yeah.

Harry Stebbings 15:24 Which is a danger. [chuckles] Totally get

Harry Stebbings 15:26 that. Dude, we, we kind of bonded over the king-making, where I-

Winston Weinberg 15:29 Oh, yeah, sure

Harry Stebbings 15:30 ... where I, you know, said, uh, some things about king-making, and you said, "That's not true." Why do you disagree with king-making as a theory?

Winston Weinberg 15:37 Yeah, I mean, and so I'll give you one example in our vertical. Um, the vast majority of our customers don't know who Sequoia, a16z, or any of those [chuckles] people even are, right? Um, and so [chuckles] I think that there's a l- you know, maybe there's a couple ways that people think about king-making. One, they think of king-making as it provides you with, like, more capital. More capital does not mean you run a better business. Like, if you, i- you could have as much capital in the world as you want, if you make the wrong product decisions, you're just gonna invest in all the wrong places, and it doesn't matter. It's the same as VC.

Harry Stebbings 16:08 Mm-hmm.

Winston Weinberg 16:08 You have 100 billion, and if you put it all into the wrong things, that still goes to zero, right?

Harry Stebbings 16:13 Mm-hmm.

Winston Weinberg 16:13 Um, so I don't think capital makes folks win. Um, the, the area where king-making or, like, people think king-making matters is customers, where they basically say, "Hey, this has, like, branded trust, and so that, that is good." I think there is, like, a little bit of legitimacy there, but it's not like only the top three VCs give you that brand.

Harry Stebbings 16:33 Sure.

Winston Weinberg 16:34 Right? A vast majority of VCs give you that brand, and what's actually interesting for us is, like, someone like EQT actually gives you that more than Silicon Valley because they're private equity, and, you know, a lot more lawyers know who that is, et cetera, right? Um, 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 c- I can tell you a, 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 other... The only other area where I know it happens an incredible amount is legal. Legal and 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? I think 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 first place [chuckles] 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 gains of, 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, though.

Harry Stebbings 17:59 To what extent does caring about the mission of the company really matter? I know that sounds a little bit cold and mercenary of me.

Winston Weinberg 18:05 Yeah.

Harry Stebbings 18:05 But if I'm a GTM leader and I'm a head of sales, and I'm a machine, and I'm here to get the number from five to 35 in the year-

Winston Weinberg 18:12 Yeah

Harry Stebbings 18:12 ... and I've done the playbook three times, I'm gonna fucking do it, and I'm gonna get my equity ramped.

Winston Weinberg 18:16 Yeah.

Harry Stebbings 18:17 Do you care?

Winston Weinberg 18:18 So I'll, I'll give you a, a good example of this. How many times a day do you think something goes wrong at Harvey?

Harry Stebbings 18:25 ... quite a few?

Winston Weinberg 18:27 Constantly, like twenty-four seven. How many times a day do you think we feel like there's, like, an existential threat, right? Or like, the big model providers are gonna release something, and maybe we haven't released something? All the time.

Harry Stebbings 18:38 Yeah.

Winston Weinberg 18:39 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- morale goes up and down, right? You, you face really difficult things, and then you have to figure out how to get through them. And so 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," and all these things. Once you're inside, your day-to-day could be crazy, and you could be thinking you're not doing very well, right? 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.

Harry Stebbings 19:37 You said about kind of existential threats.

Winston Weinberg 19:39 Yeah.

Harry Stebbings 19:40 What existential threat today concerns you most?

Winston Weinberg 19:44 Yeah, um, I think just moving fast enough on product. Like, that is, that is always, I think, the, the biggest existential threat for all the application layer companies. Um, and it's not necessarily that, you know, Anthropic or OpenAI are, you know, tomorrow, gonna put fifty percent of their resources after going the legal- 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-

Harry Stebbings 20:18 Uh-huh

Winston Weinberg 20:18 ... right? And so it's just a constant existential threat of: How do you make sure you get to, like, escape velocity on product, so you have enough of a product moat for them to not run you over? And I think about that daily. Like, when I'm thinking about competitors, my-- the main thing I think about is just I'm more bullish on these model- these labs than most people, I think. I mean, a lot of people are. Very bullish. They have incredible talent. Um, and I think more about, what are the frontier problems that our customers have that they're gonna solve later?

Harry Stebbings 20:51 4.5 changed the game for Anthropic-

Winston Weinberg 20:53 Yeah

Harry Stebbings 20:53 ... and changed the game for the landscape. Did you see usage shift entirely to Anthropic with that?

Winston Weinberg 20:58 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, uh, Opus 4.5 significantly, yeah.

Harry Stebbings 21:11 Is there a [chuckles] conflict with OpenAI when they're an investor in your company, and you're routing the majority suddenly to Anthropic?

Winston Weinberg 21:19 Well, we aren't routing the majority yet, but even if we were, there's no conflict. I mean, basically, like, they think, uh... They want us to win, and they want, you know, us to use the best model, right? Um, there's nothing in, like, our agreement or our relationship or anything like that, that you have to use OpenAI models. Um, and if anything, like, 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.

Harry Stebbings 21:51 Do you think we're seeing a plateauing in performance across the different model providers?

Winston Weinberg 21:55 Um, so I think that we're seeing a plateau in performance for consumer use cases, and the, the reason why I think this is, like, a misnomer or something that people actually shouldn't pay attention to is we don't need [chuckles] them to be better for consumer use cases. Like, I, I feel like this is something that folks don't quite understand, is like, a lot of the consumer use cases, like, four was g- like, we're done. Like, you don't need better reasoning to solve these problems. What you need is, like, different contexts. You need it to connect to your calendar. You need to connect to, you know, all of the different apps that you use and things like that. That's what an increase in performance is for them, right? Um, so I think, like, there might be a plateau in some of the consumer-facing side of things. On the enterprise, I think things are gonna keep going, and especially codegen. I think we are not going to see a plateau in codegen. I think that is gonna get much better really, really fast.

Harry Stebbings 22:48 What do you expect to see in codegen in the next twelve months?

Winston Weinberg 22:52 I think the slope will j- only increase. I think that it will get better and better and better, um, and I think that will unlock a lot of productivity just across the entire world.

Harry Stebbings 23:02 When you look within Harvey, is everyone not using Claude Code, not Cursor?

Winston Weinberg 23:06 Um, it's a combination.

Harry Stebbings 23:08 In the UK, we have a game called Shag Marry Kill. [laughing]

Winston Weinberg 23:13 [laughing]

Harry Stebbings 23:13 I'm not gonna do that here 'cause it's wildly inappropriate. Um, but if we were to do a, like, buy and sell-

Winston Weinberg 23:21 Yeah

Harry Stebbings 23:22 ... and you had Anthropic at three fifty and OpenAI at eight hundred-

Winston Weinberg 23:27 Mm-hmm

Harry Stebbings 23:28 ... which one would you buy, and which one would you sell?

Winston Weinberg 23:30 Yeah, I know, and, and we, we talked about this. I'd buy them both at double. Um, I, I think that-

Harry Stebbings 23:36 You'd buy OpenAI at one point six?

Winston Weinberg 23:40 Maybe not quite one point six. I need a... There's a couple of things I need to see from them before I would do one point six. Um-

Harry Stebbings 23:46 What do you need to see from them before?

Winston Weinberg 23:49 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, like, before this, were outside of tech, right? Um, and it-- that brand power is incredibly powerful. Um, and I think, like, 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 [chuckles] one winner, right? So no matter what, there's gonna be, you know, OpenAI's gonna get some of the enterprise market, Anthropic's gonna 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 gonna be Google, right? Um, but I think they both can be just astronomically huge companies. The other thing that I, 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. Like, people do not know how to use these systems. Like, consumers don't have- they don't, and businesses definitely don't, right? Um, and there's so much of, like, the capability-- ca- capability overhang is so high. Like, I think it's higher than anyone is 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 gonna be so many different parts of the economy that adopt these things, that I think we're still in

Winston Weinberg 25:49 early days.

Harry Stebbings 25:50 What do you think that timeline is? I know it's a horrible-

Winston Weinberg 25:52 Yeah

Harry Stebbings 25:52 ... question to ask, but is it, like, a, a two- to three-year? Is it, like, a ten-year? You work with some of these enterprises. They don't speak the language that X-

Winston Weinberg 26:01 Yeah

Harry Stebbings 26:01 - and we generally do. What does that timeline actually look like?

Winston Weinberg 26:04 I think, like, three to five years, um, until we see, like, massive, massive productivity gains in enterprise. Um, I think the capabilities are there already. The capabilities were there two years ago, right? Um, a lot of this is like... i- if you think about just, like, the average enterprise workflow, right? There's, like, seventeen different systems they're pulling data from to get that workflow done. Like, literally, seventeen might be on the low end. Sometimes it's, like, fifty, right? And a tab-- you have a hundred tabs open, and you're opening in all these different apps, and they kinda 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 gonna 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, [lips smack] you know, a lot of our revenue is starting to come from Global 2000 or Fortune 500 companies, and we actually haven't built many features for, like, 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 re- released basically a feature that's multiplayer. It's called Shared Spaces. And at first, like, a lot of the impetus for doing it was, you want a co- large corporate, like a Walmart or whatever, to work with their law firms in the same platform, and that's happening. But actually, what's starting to happen is these corporates are using the... Like, legal team is working with the compliance department, is working with HR, is working with everything else, all in Harvey at the same time.

Harry Stebbings 27:53 I heard from Lagora that the Shared Spaces was ripped from them. [chuckles] Is that fair?

Winston Weinberg 27:59 No. [chuckles] We were working on multiplayer a long time ago. I think one of the, one of the things that's interesting about our company is we started with, like, 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, right? 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 working 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 and on top.

Harry Stebbings 28:55 Why do you think they continuously say that you ripped their product ideas, then?

Winston Weinberg 28:59 Um, I think that if you are number two in the market, one of the things that's-- 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, the distribution that the other firm has.

Harry Stebbings 29:18 Do you respect them?

Winston Weinberg 29:19 Yeah.

Harry Stebbings 29:19 'Cause you guys hate each other in a way that, like... No, no, really, you do, and I, I, I love it because it's like, I feel we got too kind in tech.

Winston Weinberg 29:26 Mm.

Harry Stebbings 29:26 Like, "Oh, we're all friends." I was like: You know, we should be here to win. You know, Slootman?

Winston Weinberg 29:30 Yeah, yeah, it's very Slootman.

Harry Stebbings 29:31 Like, it's war?

Winston Weinberg 29:31 Yeah.

Harry Stebbings 29:31 We love him!

Winston Weinberg 29:32 Yeah.

Harry Stebbings 29:32 Uh, and you guys, really, you-- it's wonderful to see the animosity and hatred. [chuckles] But do you guys respect each other?

Winston Weinberg 29:39 Um, I, I think... I, I mean, I, I definitely respect them, and I think, like, one of the things that they did really well is, I think they did a great job in Europe. Um-

Harry Stebbings 29:47 Mm.

Winston Weinberg 29:47 - and, you know, this is back in 2023. We're, we're not that-- I think they're, like, six months after us or something. It, it's not that big of a gap. Um, and I think, like, one of the things that I would have done differently in the beginning is just invest, like, more in Europe in, like, 2023, right?

Harry Stebbings 30:04 Mm.

Winston Weinberg 30:04 And actually, we-- a lot of our first customers were in Europe, right? But having folks on the ground here is just really, really important, and respecting kind of, like, the different cultures and how to productionize that and all of those things, so...

Harry Stebbings 30:17 Why, why did you not out of interest in terms of coming to Europe earlier?

Winston Weinberg 30:20 It was just bandwidth. Um, I mean, we were... Like, when we signed Ano Sherman, which was our first customer, we had four people. So we did a four thousand-person enterprise-grade rollout with four people.

Harry Stebbings 30:32 Was this when you were-- I got told this from Pat, you were, like, in an Airbnb?

Winston Weinberg 30:36 Yeah, we were in an Airbnb. Uh, the o- the engineer who had joined, who was our first engineer, um, Gabe, was basically coding everything before that. Uh, he had been there for, I think, a month, and then we onboarded a four thousand-person, very large-scale enterprise, security was incredibly important, team. And so it was just bandwidth. Like, when you're scaling that quickly, it, it's harder.

Harry Stebbings 30:58 Are you shitting yourself that the platform's gonna fall over?

Winston Weinberg 31:01 [chuckles] Um, not anymore. So-

Harry Stebbings 31:04 No, no, not now-

Winston Weinberg 31:05 Yeah, yeah

Harry Stebbings 31:05 ... but I mean then, in 2023, with, like, one person-

Winston Weinberg 31:08 Oh, oh, a hundred, a hundred percent

Harry Stebbings 31:08 ... in an Airbnb. [chuckles]

Winston Weinberg 31:09 But, but, but actually, I think this is important. This is, this is something that's interesting. So 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 ninety percent front-end engineers, which is interesting to me. Um, and a lot of that reason is, I think, like, vibe coding works much better with front end than it does for infra, right? 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 build-- 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 a hundred-- hundreds of thousands, millions of customers using your product. And we kind of made that mistake in 2023. Um, and in the beginning of 2024, something that kind of slowed down our shipping velocity is we added just s- tens of thousands of users in, like, the Q4 before that, right? And we didn't quite have the infrastructure, like, to support that. And now if you look at our team, it's almost like forty percent 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 agentic systems that are processing tens of millions... You know, 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.

Harry Stebbings 32:49 So if you were advising those founders today, would you say: "Hey, really focus on prioritizing infra hiring earlier, so you're able to fulfill what you say you will do to them?"

Winston Weinberg 32:58 What I would tell them, actually, is: your GRR matters. And I think, like, 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, right? And kind of being like, "Ah, churn is fine," 'cause they're growing so fast that maybe they'll pivot or they have some customers. I think that's a huge mistake. I think that you're gonna see a lot of companies, uh, in a lot of verticals that go really, really fast to signing a bunch of customers because maybe there's 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 comp-- customers really, really fast. And I see a lot of AI companies not focusing on this, and I think that's gonna be, like, a huge reckoning for folks once they get past a hundred million ARR.

Harry Stebbings 33:50 This is what I worry about, though, when I look at kind of-- when you look at GRR figures, and you think about-

Winston Weinberg 33:54 Yeah

Harry Stebbings 33:54 ... like a, a Sierra, and it's like the growth rate. And Brat's amazing, and, like, the best of the best. Jesus, like, take my money too, Brat.

Winston Weinberg 34:01 [chuckles]

Harry Stebbings 34:01 I'm not, I'm not questioning you, but I'm like: Gosh, what you have to now fulfill from a per-customer implementation-

Winston Weinberg 34:09 Yeah

Harry Stebbings 34:09 ... service provider aspect to go from a hundred to four hundred is a lot.

Winston Weinberg 34:15 A lot.

Harry Stebbings 34:16 Like a lot, a lot. It's not like a plug-and-play. Like, it's much easier to go on the consumer side from a hundred to four hundred-

Winston Weinberg 34:21 Yep

Harry Stebbings 34:21 ... with a PLG motion.

Winston Weinberg 34:23 Yes. Agree, and I, I think that what that requires then is going back to what we were saying, which is how 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 gonna end up happening, I think, is a lot of these verticals are gonna land at a big Fortune One or Fortune Two or whatever, right? And their product is gonna expand massively. This is a really interesting thing about Microsoft. I don't, 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, right? 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, et cetera. 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 gonna 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, right? Like, it's gonna change astronomically. And so what's more important than landing new customers and getting really high ARR, 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 a hundred million at some point. I think Databricks is a company that's done an incredible job of this.

Harry Stebbings 35:57 [chuckles] I had Alex Rampell-

Winston Weinberg 35:59 Yeah

Harry Stebbings 35:59 ... who's obviously at Andreessen, one of your, uh, investors, on the show recently, and he said something that I loved, and it sounds a bit awful, but I loved it. [chuckles] Um, he said: "I want companies who have hostages, not customers." [chuckles]

Winston Weinberg 36:09 [chuckles]

Harry Stebbings 36:09 Okay? And as, again, as kind of bad as that sounds, I did like it. In this space, are they hostages or customers? How easy is it for them to move?

Winston Weinberg 36:18 Yeah, I mean, there's, 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 I think 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 gonna start aligning to that. And the, the reason why is... Let me-- like, 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 would-- could you ever sell to them? There's no way that this is gonna 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 gonna 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 M&A with this custom solution that we did in Harvey," and they win that deal over another law firm.... That's not a hostage. That's this product that I'm paying maybe, like, a million dollars for a year just earned me a deal that's twenty million. What is the ROI on that? Incredible. And then on the insi- in-house side, it's even clearer. It's just if you ti- save time, you're saving tons of money. So I, I think that hostage thing can actually change to more like how Palantir thinks about it, which is, I think the value of B2B SaaS is about to become astronomical, and if you can figure out how to align your product to that ROI, it's not a hostage, it's-- you're just completely aligned with your customer.

Harry Stebbings 37:58 How do you align product to ROI when your customer base doesn't wanna pay for a consumption model-

Winston Weinberg 38:03 Yeah

Harry Stebbings 38:03 ... and they just wanna pay for a seat model that they know and can rely on?

Winston Weinberg 38:06 Yeah. I, I think that that's not, at least in our vertical, what I've seen. Um, I think, like, there, there are a lot of areas where we are gonna start moving to consumption-based pricing, and I think for, at least for us, for our customer base, that would be completely fine with

Winston Weinberg 38:21 them.

Harry Stebbings 38:21 Rory O'Driscoll, the Irish guy, uh, who I quote so often, he's brilliant, and should basically just replace me at this point- [laughing]

Winston Weinberg 38:27 [laughing]

Harry Stebbings 38:27 ... uh, he's much smarter than me. Uh, but he always says, like, "AI will be magnificent for us all if we see spend shift from technology budgets or fr- sorry, from human labor budgets to technology budgets."

Winston Weinberg 38:39 Correct.

Harry Stebbings 38:39 Will we see that shift here?

Winston Weinberg 38:41 Already seeing it happen.

Harry Stebbings 38:42 How does that happen?

Winston Weinberg 38:43 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, and the, the budget for professional services is in the billions a year, versus the tech budget for that GNA group is astronomically smaller.

Harry Stebbings 39:05 Sorry, the professional services budget is not the junior talent that they have in their organization?

Winston Weinberg 39:10 No. No, and I think that's what's really interesting about our business, is

Winston Weinberg 39:15 a lot of the work 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, like, lower-end work.

Harry Stebbings 39:26 What percent of revenue is law firm versus external?

Winston Weinberg 39:29 Uh, right now... So, oh, so you mean corporate versus law firm?

Harry Stebbings 39:32 Yeah.

Winston Weinberg 39:32 Uh, I think it's around forty percent of our revenue is in-house, corporate, and sixty percent is law firm. Something like that.

Harry Stebbings 39:38 Wow! Sixty percent is law firm, forty percent's, like-

Winston Weinberg 39:41 In-house

Harry Stebbings 39:41 ... Fortune five hundred.

Winston Weinberg 39:42 Corporate. Yeah, yeah.

Harry Stebbings 39:42 Wow. Is that what you thought it would be?

Winston Weinberg 39:45 Um, I think, like, something like that. I mean, if you just look at the breakdown of, like, how many lawyers exist on Earth and how many of them are at companies versus-

Harry Stebbings 39:54 Yeah

Winston Weinberg 39:54 ... in-house, that's pretty much the same. So I don't see that changing.

Harry Stebbings 39:56 In five years' time, what will that be?

Winston Weinberg 39:58 I think it'll be similar. I think it'll be the same.

Harry Stebbings 40:00 Got you. How will we see law firms change?

Winston Weinberg 40:03 Yeah.

Harry Stebbings 40:03 Will we have a kind of cannibalisation of juniors?

Winston Weinberg 40:08 I, I don't think so. I think we'll just get more work. So i- th- interesting, I had a conversation with, um-

Harry Stebbings 40:14 Are you gonna make my girlfriend unemployed?

Winston Weinberg 40:15 [laughing] No. Um, I had a conversation, uh, with, like, a pretty large, like, private equity shop recently, and they were talking about, like, their year is gonna be incredible. Like, they think it's gonna be, like, a big M&A year, it's gonna be great. And they were talking about, like, how they think about legal fees, right? And the way that they thought about legal fees is, "The reality is, like, it's gonna 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 wanna pay for anymore, right? Like, there are certain parts of the deal, et cetera, that I just... marking up NDAs, whatever it is, I don't wanna pay for that anymore, right? But there's all these new things [chuckles] that I'm paying law firms for, like AI risk. [chuckles] Like, should you buy this company? Is there a, you know, a problem in XYZ country with, you know, an act or something like that that's gonna change it?" There are so many new pieces of work for professional services that my gut is, that's not what's gonna happen. In fact, I think what's gonna happen is the professional services market is going to actually keep growing at the same as GDP. Like, 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, like, litigation is somewhat countercyclical, it, it depends on the, on the area. And so I think people think about this, and they're like, "Oh, wow! Like, AI is gonna impact legal, and it's gonna 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 [chuckles] to legal advice. What happens when, you know, 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 gonna happen, right? And probably what's gonna happen is the economy's gonna explode, these companies are gonna have crazy expectations for what they can do, and the professional service providers are gonna have to respond to that.

Harry Stebbings 42:13 Do you think the economy is gonna... So I can't believe I'm asking this question, 'cause it feels like the most base question that shit interviewers ask-

Winston Weinberg 42:18 [laughing]

Harry Stebbings 42:18 ... but maybe I'm just a shit interviewer at this stage, to be honest. Um, do you think the economy is gonna continue to explode? We have so much external concern outside-

Winston Weinberg 42:26 Yeah

Harry Stebbings 42:27 ... of the atmosphere-

Winston Weinberg 42:27 Yeah

Harry Stebbings 42:27 ... which says, like, "Hey, the circular deals are fucking nuts," you know? Um, "US borrowing has never been higher."

Winston Weinberg 42:33 Yeah, yeah.

Harry Stebbings 42:33 "Europe is a fucking museum that is completely unproductive." [chuckles]

Winston Weinberg 42:37 [chuckles]

Harry Stebbings 42:37 Um, beautiful. Um, uh, we are gonna have a serious and material slowdown. Do you think that's wrong?

Winston Weinberg 42:43 I don't think it'll be this year. Um, I think there will be bumps. Like, I definitely think we will have, like, more moments like the DeepSeek moment, where, like, everyone freaks out, right? And I think we're, we're close enough to, like, an, an edge of... You know, i- if enough people say that there's gonna be a bust, it's pretty easy for, like, one thing to happen, and for everyone to freak out, and there to be a bust, and it's a self-fulfilling pros- prophecy. Those are usually, like, pretty short. Um, 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

Winston Weinberg 43:17 that.

Harry Stebbings 43:17 I do have to ask, you mentioned Europe, and we spoke a little bit about kind of Europe's productivity there. You said you wish you'd kind of-... been more proactive earlier on in Europe, but there's only so much you can do, but blah. What do you know now about building teams in Europe-

Winston Weinberg 43:30 Yeah

Harry Stebbings 43:30 - that you wish you'd known when you started?

Winston Weinberg 43:33 Oh, I, I think that it's similar in Europe to where it is in a lot of places, which is you don't wanna 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 so-- And when I say, you know, we should have invested more in that, it's more like we didn't invest in, in it that much in twenty twenty-three and twenty twenty-four. We invested tons last year, and we're investing even more this year, and the difference is pretty massive. Like, the, the difference in kind of the quality of our team of 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, kinda thinking about how to do it. You've gotta travel.

Harry Stebbings 44:23 What's the biggest difference in talent between the US and Europe?

Winston Weinberg 44:27 I think that the, the biggest difference in... It's not a difference in talent, it just takes a long time to hire people, right? Uh, and so you have to just think about it for, like, with a way, way longer time horizon.

Harry Stebbings 44:39 Because of gardening leave.

Winston Weinberg 44:40 Yeah.

Harry Stebbings 44:40 Yeah.

Winston Weinberg 44:40 It's just, like, really hard to hire people. Um, and so that was just kind of, like, interesting to me or something that I wasn't used to. Whereas in the States, you can hire someone, and they, they start quite literally, like, the next day sometimes, right? Like, literally, or if they have to give two weeks' notice, they start exactly two weeks later, right? Um, and so that allows you to be a little bit more f- like, just I quickly need to hire this. Retroactively, I can fix a problem. In Europe, you have to plan out more, right? Um, and so we've done a, a lot of really big office openings, like we just, uh, announced Paris and Dublin and a bunch of other ones. Um, but you have to just think about this stuff at, like, a longer time horizon. You can't do it instantaneous.

Harry Stebbings 45:21 Is the US trope of Europeans not working as hard fair?

Winston Weinberg 45:27 That's not what I've found, but I will say we interact-- I interact mostly with lawyers, and, like, lawyers have billable hour targets, right? Um, and at the end of the day, too, they are either at international firms or they're competing against international firms. So I have not found that at all, right? I mean, there are so many incredible, hardworking lawyers in Europe.

Harry Stebbings 45:47 UK lawyers work pretty hard.

Winston Weinberg 45:48 UK lawyers work insanely hard.

Harry Stebbings 45:50 Yeah, yeah.

Winston Weinberg 45:51 Um, 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.

Harry Stebbings 46:02 In terms of the people assessment, Pat told me that you're world-class at understanding people. If I were to ask you for a trait that you look for in someone joining Harvey that is less obvious than the foundational integrity or, like, ambition-

Winston Weinberg 46:16 Yeah

Harry Stebbings 46:16 ... or bullshit that you normally get. Like, I look for obsessed psychopaths. [chuckles]

Winston Weinberg 46:20 Mm-hmm. [chuckles] That's a good one. You definitely need to be obsessed.

Harry Stebbings 46:24 Yeah. What would yours be?

Winston Weinberg 46:25 So I... So obsession is definitely very important, but the one that I look for right now a lot is ownership. It's really, really important. Um, 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. Um, and the, the reason this becomes really important is, as you scale as a problem or as a, as a company, it becomes really hard to figure out where a problem is stemming from. It becomes hard because what... Th- 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 gonna 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. [chuckles] It's like the Spider-Man meme, right?

Harry Stebbings 47:17 [chuckles] Yeah, I love it.

Winston Weinberg 47:17 Um, and what I have found is-

Harry Stebbings 47:20 That's like, that's like bad deals in venture firms. "Who did the deal?"

Winston Weinberg 47:23 Yeah, and it's just, "Uh..."

Harry Stebbings 47:24 [laughing]

Winston Weinberg 47:24 It's like all over the place. Yeah, exactly, right?

Harry Stebbings 47:26 It was Johnny who left.

Winston Weinberg 47:27 It was Johnny, and I don't know.

Harry Stebbings 47:28 [chuckles]

Winston Weinberg 47:28 And, and, and I have found that there are a lot of people in tech that have done a really good job managing up. Um, and they have ridden a wave of their team's success without being successful themselves. And so the thing that I look for a lot is: Can people admit their mistakes? And there is something... It is, to me at least, 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, right? Like, 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 get over-

Harry Stebbings 48:06 Well, I mean, yeah, yeah, and you said, like, checking Slack too much.

Winston Weinberg 48:07 And I said, "Oh, I'm too obsessed." Right, right.

Harry Stebbings 48:09 Yeah.

Winston Weinberg 48:09 And, and, like, that, I think, is a good example of, like-

Harry Stebbings 48:11 I was thinking like alcoholism, bulimia-

Winston Weinberg 48:13 Alcohol... Something like that. [chuckles]

Harry Stebbings 48:14 [chuckles]

Winston Weinberg 48:14 Yeah, totally.

Harry Stebbings 48:15 This dude is too... [chuckles]

Winston Weinberg 48:16 And, and, like, I would actually, if I'd interviewed myself, and I saw that as a, a question, the, of, like, 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 be-- 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 gonna handle that problem. And now, all of a sudden, it actually is ownership. Like, it is, like, 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, right?

Winston Weinberg 48:54 And-

Harry Stebbings 48:54 Where, where, where do you think that comes from? I, I, I have trust issues 'cause I've found that, generally, when relationships break down, it always comes down to them extorting me for money.

Winston Weinberg 49:03 [chuckles] Great.

Harry Stebbings 49:04 It's true.

Winston Weinberg 49:05 Yeah. I think my trust issues... I mean, I think part, you know, part stuff is it's hard to tell whether it's, like, nature or nurture, right? Um, but I, I think that I definitely had some problems with authority when I was younger. Uh, and I had a, um, not the normal Silicon Valley kind of background and upbringing. Um, and because of that, I think that I had to-- I really went out on my own at, like, a pretty young age and was pretty independent. Um, and I think that one thing that you have to learn when you're leading a company, um, 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, right? 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 of this as like a sports team. There are people I know that they don't care about winning the championship, they wanna be the person who scored the most points. And they're okay with losing the championship, as long as they're the one that scores the most points. Those are the exact type of people that I do not wanna work with. I wanna work with people that do care about how many points they've scored, but they care about that because they w- they helped win the game, right? And I think that's a huge problem in tech, is we- you have too many people that it's me, me, me, me, me, and not company, company, company. So-

Harry Stebbings 50:29 God, I think, I think the US is just full of logo chasers. [chuckles]

Winston Weinberg 50:33 There's a lot of that, yeah.

Harry Stebbings 50:34 You guys just love to, like, work at a hot company. It's the hot company bouncer, I call it, where it's like they just go two year, two year, two year, two year, and it's like they're doing venture portfolios with, like, company equity.

Winston Weinberg 50:44 Yeah.

Harry Stebbings 50:44 And, and it's just like, God!

Winston Weinberg 50:45 I was about to say VCs do the same thing.

Harry Stebbings 50:46 And I sit in these operator groups, and they're like, "Ooh, I hear Clay's really hot," or, "Ooh, I hear, like, Notion's really hot."

Winston Weinberg 50:52 Yeah, yeah.

Harry Stebbings 50:52 And they just jump.

Winston Weinberg 50:53 Yeah. I mean, I think the VC-

Harry Stebbings 50:54 The promiscuity of American operators is incredible.

Winston Weinberg 50:56 Is, is the same thing. But, but, but, like, look at-

Harry Stebbings 50:58 Brits are too negative. We're like, "That's crap." [laughing]

Winston Weinberg 51:01 That's... [laughing]

Harry Stebbings 51:02 "Don't be a dick."

Winston Weinberg 51:03 Yeah. I mean, I, I think, like... This also- I, I forgot who tweeted this. I don't re- I don't remember w- who it was, but this was, like, early 2022, um, and, like, it was... Or, sorry, end of 2022, and it was, like, right after the ChatGPT 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 gonna happen is a lot of VCs, because they don't understand the AI ecosystem, they're gonna revert back to looking at resumes, because they don't understand." And this is what people do. When there's 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, you know, as the markets, you know, mature, this stops happening. But there's a lot of, "I don't really understand this, and so what I'm gonna do is look at the resume or look at a logo or look at that, because that seems like a safe bet."

Harry Stebbings 52:06 How many truly great researchers do you think there are?

Winston Weinberg 52:09 Hundreds, and that's it.

Harry Stebbings 52:11 How do you know a good researcher from a resume?

Winston Weinberg 52:14 I, I don't think you can. That, that I think is actually a, a pretty big disconnect. The researcher community knows. So, like, this is a huge disconnect between VCs, I think, and the researcher community.

Harry Stebbings 52:24 So what would you [chuckles] advise me investing?

Winston Weinberg 52:27 What 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. [chuckles] Um, and because of that, if you, 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. Like, it, it, it's not like that.

Harry Stebbings 53:06 How do you assess the promiscuity of AI researchers?

Winston Weinberg 53:09 Yeah.

Harry Stebbings 53:09 I mean, like, you know, poor old thinking machines, you know, uh, home alone as M- Mira Murati now. Um, how do you assess that? Is that just a sign of the very brilliant times?

Winston Weinberg 53:21 Yeah. I, 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 sometimes, like, to your point of, like, people just wanna join hot companies... Like, a lot of tech, I think, is, like, people just wanna join hot companies, right? Um, researchers really genuinely do care about pushing research forward, and I think what ends up happening sometimes is the leaders at some of these companies kind of change the direction of the company, and the researchers are no longer interested in that direction of the company. And that happens a lot at these big labs. Like, they're making multiple bets at multiple places, and w- what ends up happening is the people say, "Ah, this isn't what I signed up for." It's kind of like a bait and switch, and they go to something else. And, and by the way, this has nothing to do with thinking machines. I'm just saying this is what's happening, I think, at all of these labs is, you know, you go to work at Meta, you go to work at OpenAI, you go to work at Anthropic, and you think you're gonna work on something, and then you end up not. And, you know, they're in insanely high demand. They're able to pick what projects they wanna go work on.

Harry Stebbings 54:30 How bad is the war for talent? You're in the midst of it.

Winston Weinberg 54:33 Yeah, it's in- and it's incredibly... It's very, very high. And, and, and one thing maybe, um, to bring up is, I think that over time... We have this interesting thing where it's like a lot of the AI companies, like application layer companies, including ourselves, like in the beginning, we're like wrappers, right? Um, and what's gonna happen over time is these companies are gonna do two things. One, a lot of just the core software that they build, it's not even gonna be AI-related. It's just core software building, and that's actually gonna be mu- very differentiated. The second thing that's gonna happen is, none of these companies have access to proprietary data until very recently, right? And so a lot of the stuff that we're looking at is, how do you actually create, like, custom solutions for, like, a large enterprise, right? And that is AI problems again, right? So now we're all the way back to, like, AI actually mattering, and I think that what we're gonna see is that kind of main problem of a lot of these companies haven't hired any i- AI talent. And a lot of what they've done is kind of just... You know, 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 gonna matter again. Um, 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

Winston Weinberg 55:55 work.

Harry Stebbings 55:56 We, we said about the skill of people assessment in terms of the talent there. We said about your lack of trust and trust issues, which was another one-

Winston Weinberg 56:02 [laughing]

Harry Stebbings 56:03 - that I think it was Pat told me. I put one of your investors, but I'm gonna throw him under the bus. I think it was Pat.

Winston Weinberg 56:07 Perfect. Great.

Harry Stebbings 56:08 Yeah, yeah. Sorry, Pat.

Winston Weinberg 56:09 [chuckles]

Harry Stebbings 56:09 Um, Pat did also say that you're an excellent deal guy.

Winston Weinberg 56:12 Mm.

Harry Stebbings 56:13 And I wanted to unpack that. What was your biggest advice on how to get the best deal-

Winston Weinberg 56:18 Yeah

Harry Stebbings 56:18 ... in deal-making?

Winston Weinberg 56:19 Um, maybe two pieces of advice. One is listen more than you speak, and it's very, very dumb, but it's true. Um, I think a lot of people in deals they think that movement is action. So they think that, like, movement is progressing the deal forward, and they think that if they talk the most, they're in control of the deal. Not true, right? 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, like, all deal-making is just people reading. That's it. And it's people reading at scale. So it's people reading, like, a one-on-one conversation, and then it's reading groups of people, and then it's reading, you know, entire verticals of people, et cetera, and it's figuring out what they want. The second piece is know when to not negotiate. 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, right? And if you understand the value of something more than everyone else does, throw all your-- all of your principle deal-making, and you're supposed to negotiate X and then Y, and then it'll be fifty percent 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. And I know a lot of people that... The best deal-makers I know, like, the best, they do-- they know that very well.

Harry Stebbings 58:06 When did you understand the value more than everyone else, and how did that shape how you behaved?

Winston Weinberg 58:11 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'd help 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, seventeen ropes in this hand, you have seventeen ropes in this hand, you're grabbing all these ropes, and at some point you're gonna get, like, pulled apart 'cause it's just too much pressure, and you're gonna 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 tied. And then you tie another one, and then you tie another one, and you tie another one. And tying those ropes allows you to pull more ropes, right? And, like, that's a lot of how I think about deal-making. Um, I think another company that has done an incredible job of this is Microsoft. Incredible job. Of they've created this partnership ecosystem, right? And a lot of people have given them a lot of flack of like: "Why do you let people do X, Y, Z partnership? Why do you let people build on this? Like, they're just gonna 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 gonna, you know, be very tough on this."

Harry Stebbings 59:44 I think one actually also is, always when you hire people, and, you know, they say that they want seventy-five grand.

Winston Weinberg 59:49 Oh.

Harry Stebbings 59:49 And then so often I meet founders, and they're like: "Ha! But I got them down to seventy." And I'm like: "Give them seventy-five."

Winston Weinberg 59:54 Give them seventy-

Harry Stebbings 59:54 They won. They start, they feel valued.

Winston Weinberg 59:56 With hiring, this is a, a sup- a huge mistake that people make, massive mistake. If you wanna 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, it's a separate problem, but don't go back and forth. Doesn't matter.

Harry Stebbings 1:00:13 One of the most valuable bits of advice Josh Kushner actually gave me, I love him, is he said, "If you're..." And this was on a specific in, like, investments. "If you're willing to take less, don't do the deal."

Winston Weinberg 1:00:22 Yeah.

Harry Stebbings 1:00:22 Imagine I'm a VC, and it's like I want ten percent. You're like: "I can only give you seven." I'm like: "I'm actually fine with seven."

Winston Weinberg 1:00:27 Well, then you don't believe-

Harry Stebbings 1:00:28 Don't do the deal

Winston Weinberg 1:00:28 ... in that company.

Harry Stebbings 1:00:29 Hundred-

Winston Weinberg 1:00:29 That's not gonna be a legendary, category-defining company.

Harry Stebbings 1:00:32 A hundred percent.

Winston Weinberg 1:00:32 It won't be.

Harry Stebbings 1:00:33 Agree.

Winston Weinberg 1:00:33 It's impossible.

Harry Stebbings 1:00:34 You said about m- people and kind of reading people in a deal, when did you most misread someone, and how did that shape your mindset?

Winston Weinberg 1:00:42 I think one of the, 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-

Harry Stebbings 1:00:55 Mm

Winston Weinberg 1:00:55 ... and I've misread that, and then I real- I didn't realize how easy it would be for them to learn how to do it, right? Um, and so 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 the mistake of reading too much on the surface, um, 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, um, and I think that's a huge mistake.

Harry Stebbings 1:01:30 You mentioned, um, OpenAI and Sam as the deal-maker as well with this different-

Winston Weinberg 1:01:34 Very good

Harry Stebbings 1:01:34 ... I liked it. [chuckles] Um, I heard that you cold-called Sam-

Winston Weinberg 1:01:38 [chuckles]

Harry Stebbings 1:01:39 - uh, in the summer of twenty twenty-two. Can you just tell me about that before we do a quick fire?

Winston Weinberg 1:01:44 Yeah. So it wasn't a cold call. We, we cold emailed them, um, and we cold emailed Sam and Jason Kwon. Um, what we had basically done was we go- went on r/LegalAdvice, which is basically like a subreddit for asking legal questions, and we grabbed a bunch of those questions, ran a chain of thought-... product that we had basically built on top of it, and gave it to a bunch of landlord tenant attorneys. And then we basically said, just, like, "Look at these questions, and tell me if they're- you would send the answer," we didn't say anything about AI, "to the consumer who asked the question." And of 86 out of 100 questions, three out of three said, "This is a perfect answer. I'm done." And we cobbled all that together, and we just sent a cold email to Sam Altman and Jason Kwon. Um, the idea was basically, "Hey, did you guys know that..." You know, 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. Um, "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 at legal?" Um, and we met them, like, pretty recently after that.

Harry Stebbings 1:02:45 How did that go?

Winston Weinberg 1:02:46 Uh, it went well. Uh, we had a call with Jason first, and just kinda talked about, like, what is our strategy as a company, um, 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, uh, 2022. Yeah, it was, like, 11:00 AM on July 4th, uh, and we did a pitch to the rest of the company.

Harry Stebbings 1:03:05 Do you get nervous before these? Like, when you go into a Sequoia-

Winston Weinberg 1:03:08 Yeah

Harry Stebbings 1:03:08 ... and you pitch the partnership. Fuck, that's nerve-wracking.

Winston Weinberg 1:03:11 So, yes, I had a weird thing where, like, I didn't know who any of these guys were. Um, and so, like, when we were doing our series... So we-

Harry Stebbings 1:03:19 It's so funny, 'cause, like, you don't know, and, like, for me, as a venture nerd, I'm like, "Holy shit!"

Winston Weinberg 1:03:24 Yeah, you're like super scared.

Harry Stebbings 1:03:24 Like, I know everything about every one of them.

Winston Weinberg 1:03:25 But, like, I mean, like, now I do, but back then, I didn't know anything. Like, so... I mean, I didn't even have friends in tech. Um, 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, we did like-

Harry Stebbings 1:03:40 God, how much did they invest, and for how much?

Winston Weinberg 1:03:42 The actual terms... I don't remember what the post actually was, but the pre-investment was, like... It was, like, 4 million or something like that. Um, and anyway, what happened at this, 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, like, knew, and he basically gave me advice and things like that. So I actually think I had, like, a p- weirdly unique view of the VCs because my entire judgment of them was just how, like, how that first meeting went. Like, I didn't know that, like, this Sequoia was in this tier, and this one was in this tier, and, you know, whatever. I didn't know any of that.

Harry Stebbings 1:04:29 You did-

Winston Weinberg 1:04:29 I didn't even know who they were

Harry Stebbings 1:04:29 ... 10 VC meetings.

Winston Weinberg 1:04:31 Yeah.

Harry Stebbings 1:04:31 How many term sheets did you get?

Winston Weinberg 1:04:33 Um, for that? I, I don't remember. It was, I think, like, half or something like that, yeah.

Harry Stebbings 1:04:39 Which was the worst?

Winston Weinberg 1:04:40 The worst term sheet or the worst meeting?

Harry Stebbings 1:04:42 Worst meeting.

Winston Weinberg 1:04:42 Oh, I'm not gonna say that publicly. [chuckles]

Harry Stebbings 1:04:44 It's worth a go.

Winston Weinberg 1:04:45 There was one. Oh, there was one, um-

Harry Stebbings 1:04:46 Why was it bad? Just tell me that.

Winston Weinberg 1:04:47 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. Like, did not even make eye contact. Literally, zero.

Harry Stebbings 1:04:59 They were just taking notes. Yeah, they were taking-

Winston Weinberg 1:05:01 No!

Harry Stebbings 1:05:01 They were, they were-

Winston Weinberg 1:05:01 I think they were texting a friend. [laughing]

Harry Stebbings 1:05:04 [laughing] Can't believe this knob is still talking about legal.

Winston Weinberg 1:05:06 Yeah, yeah, I was just like, "What are we doing here?" [chuckles] Yeah, that was the worst one. That was really bad.

Harry Stebbings 1:05:09 That is absolutely

Harry Stebbings 1:05:10 amazing. Uh, listen, I wanna move into a quick fire round.

Winston Weinberg 1:05:12 Yeah.

Harry Stebbings 1:05:13 Um, what have you changed your mind on in the last 12 months?

Winston Weinberg 1:05:16 Um, yeah, how much... So I said earlier that a lot of company-building has changed. I actually think a lot of it remains the same. [chuckles] Uh, 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 wanna 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 have hired 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, like, laws of physics about companies that remains the same. Like, there's no different in AI. Um, and I think, like, in the past, maybe t- what have I learned in the past 12 months? Maybe it's more, what have I learned in the past, like, 18, like, the, the second half of the company, basically, is how much of a lot of the company building is actually the same. Uh, and I probably should have listened to people a little bit more about that.

Harry Stebbings 1:06:27 You have Sequoia and Andreessen on the cap table.

Winston Weinberg 1:06:30 Yeah.

Harry Stebbings 1:06:30 How are they different to work with? I'm not asking, like, for better or worse, but how do you... How are they different to work with?

Winston Weinberg 1:06:35 Yeah. I think that there's obviously, like, a difference in scale, right? Like, a16z is just, like, a lot, a lot bigger. I would say that a16z is l- just also, like, louder, right? Um, and so they're a little bit more in, like, these other regions and other areas and things like that. Um, whereas Sequoia is, you know... I- it's just a different style, right? It's closer to... There aren't as many partners and, and things like that.

Harry Stebbings 1:06:59 Were you nervous pitching to Marc and Ben?

Winston Weinberg 1:07:01 Um, uh-

Harry Stebbings 1:07:03 You knew them coming in.

Winston Weinberg 1:07:04 Yeah, definitely.

Harry Stebbings 1:07:04 Yeah.

Winston Weinberg 1:07:05 Yeah, definitely. I mean, I, I'm, I'm always nervous, and I, I think, like, one thing, too, I, I think I said this earlier, but, um, I think Keith Rabois says this, who I've actually never met in person.

Harry Stebbings 1:07:13 Wow.

Winston Weinberg 1:07:14 Um, there's a, there's a, a, a couple people... I have a list, actually, at the top of, like, 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, like, learned from them or something like that. Um, and, uh, I've never actually met Keith Rabois. I think he's an investor in one of our kind of, like, slight, kind of competitors.

Harry Stebbings 1:07:34 He's in Spellbook.

Winston Weinberg 1:07:35 Yeah, yeah, yeah.

Harry Stebbings 1:07:36 Yeah.

Winston Weinberg 1:07:36 We, we don't compete with them tons, but in some degrees, we do. Um, but anyway, o- one of the things I think he was talking about, uh, uh, 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. Um, I strongly agree with that, like, really agree with that. Like, I think the times that I've stagn- or the company has stagnated, is-... every day I don't have something that's, like, really stressful. Like, 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, "Ah, shit!" [chuckles] Like, I have- like, tomorrow is gonna be... Like, there's so many things. Everything needs to go right. I'm really stressed. It's compounding, like massively compounding for you as an individual, to just put yourself through that stress.

Harry Stebbings 1:08:22 I freaking love it. Uh, Pat r- like, tweeted, like, "Hey, if you are, like, ambitious and you wanna learn about working in AI applications, there's no better place to work than Harvey." Keith Rabois? Hmm. [laughing]

Winston Weinberg 1:08:35 [laughing] Oh, somebody said that. But, but, but, but Pat has this-

Harry Stebbings 1:08:38 My point is, though, dude, I love the way, like, you didn't see that, but, like, all VCs are just like-

Winston Weinberg 1:08:41 I didn't see that

Harry Stebbings 1:08:42 ... "Oh!" [chuckles]

Winston Weinberg 1:08:43 Yeah, yeah. I mean, but, but it's interesting. Like, I think Pat also has this, too, and, and all of my VCs do, and, and Pat in particular, he really thinks of, like, just constant... Like, a "relentless application of force," is what he says, and that's actually what I have next to his name. Um, and i- that's incredibly important, and I think that if you lose that as a company, the company's pretty much over, right? Um, I think that you're- you as a founder need to constantly, constantly be a- 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-

Harry Stebbings 1:09:20 I- who-

Winston Weinberg 1:09:21 ... and I think that will trickle down to the rest of the company.

Harry Stebbings 1:09:23 Who... A couple of other people on that list, and what they- what do you have next to them?

Winston Weinberg 1:09:26 [laughing] I have Brian Halligan's on there, uh, and his is "No." It's just the word, "No." And one of the things... He's been incredibly influential and, and helpful to me, and one of the things I had a problem with is just, like, saying no to things. Um, 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? Um, and it's the same with, uh... 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, um, 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 of, like, every time that we do product planning, something should hurt. It should feel like a breakup. [chuckles] Like, you are- you have to... There's has to be a couple really good ideas that you say no to, and it's the same as across the entire company. And Brian Halligan has been really helpful with kind of teaching me how to do that for myself, and how to do it with the rest of the company.

Harry Stebbings 1:10:33 I always go with the John Elie of which is, like, you know, "Prioritization is saying no to even really good ideas."

Winston Weinberg 1:10:37 Yeah, yeah, yeah. No, I think that's right. It should feel painful. It really should. Um, and I didn't do that in the beginning. I was like, "Ah, we'll just do everything, whatever." And I think... Uh, having said that, I do think you can do more, and I think you can be very ambitious. Um, but you do have to strike a balance between the two.

Harry Stebbings 1:10:52 You can only take one investor with you to your next company. Which investor do you take?

Winston Weinberg 1:10:57 I'm definitely not answering that question. [laughing]

Harry Stebbings 1:11:00 [laughing] There's, like, several hundred million dollars on the line at this point.

Winston Weinberg 1:11:04 Yeah, yeah, I'm not doing it. No, I'm not that stupid.

Harry Stebbings 1:11:05 "How did you ruin the relationship?" "I went on Harry's pod."

Winston Weinberg 1:11:08 [laughing]

Harry Stebbings 1:11:08 "Uh, I really pissed him off." That's, that's super funny. Who do you not have on your board, who you'd love to have on the board?

Winston Weinberg 1:11:15 Yeah. Um, I mean, I've always respected Founders Fund. Like, I've always really, really respected them. Um, I've re- respected the hell out of their companies, too, and, and a lot of their founders. I just... I, I respect them a lot, uh, and we've, we have never worked with them.

Harry Stebbings 1:11:28 In a year's time, where is Harvey then? You did this great tweet yesterday, and it was like 190 million in ARR, uh... I can't, I can't remember the customer base, and can't remember the other stats.

Winston Weinberg 1:11:37 It's all good.

Harry Stebbings 1:11:37 Such a VC.

Winston Weinberg 1:11:38 [chuckles]

Harry Stebbings 1:11:38 It's like, revenue number, great, that's the take. Uh, what does that tweet say in 12 months?

Winston Weinberg 1:11:43 Yeah. Um, I mean, we obviously have revenue targets and things like that, but what I wanna switch from is a productivity s- software that is, like, a nice-to-have, to s- to closer to, like, an operating system that is, like, pretty much crucial to the industry, right? Um, and so it's more how do we, how do we... We've built a lot of different, like, features across the board, right? Like, we very much, like, in, in Parker Conrad's voice, like, built a compound startup, like, very much. We haven't tied it all together yet. We haven't. Like, we've done a really good job of creating all the pieces, hasn't tied together. Um, and, uh, 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 four-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 infrastructure?

Harry Stebbings 1:12:45 Mm.

Winston Weinberg 1:12:45 Can we make it so it is, like, this is a core piece of a lawyer's work and day, and they live in it?

Harry Stebbings 1:12:50 It's a move from product to platform.

Winston Weinberg 1:12:52 It's 100% that, and I think we've done a good job of creating all the features, but now I wanna 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.

Harry Stebbings 1:13:04 Dude, it's such a pleasure to have you on the show. Thank you so much for doing it in person. It makes such a difference, and you've been incredibly amenable to my pressing. [chuckles]

Winston Weinberg 1:13:11 [chuckles] Well, thank you so much for having me, man.