The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

Winston Weinberg argument clarity score 4.2/5 from 41 exchanges on raw tape · average scores: directness 4.5 · coherence 4.4 · precision 3.9 · compression 3.7 record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered raw tape D 5 · C 5 · P 5 · Cm 5 5.00

Q You mentioned, um, OpenAI and Sam as the deal maker as well with this. Very good. I liked it. Um, I heard that you cold called Sam in the summer of twenty-twenty-two. Can you just tell me about that before we do it? Yeah.

A So it wasn't a cold call. We, we cold emailed them, um, and we cold emailed Sam and Jason Kwan. Um, what we had basically done was we went on r slash legal advice, 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 a hundred 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 Kwan. Um, the idea was basically, hey, did you guys know that, you know, at this point it was GPT-III 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.

AI assessment note: “So it wasn't a cold call. We, we cold emailed them”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q 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. Yeah. And it just makes me feel like I've accomplished something very quickly and I'm hydrated fast. Yeah. What would yours be?

A 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 four 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 too.

AI assessment note: “I think it's getting up early. Um, it, it's helped a lot.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Yeah. Which is a danger. Totally get that. Dude, we, we kind of bonded over the king making where I, where I, you know, said some things about king making and you said, that's not true. Why do you disagree with king making as a theory?

A Yeah, I mean, so I'll give you one example in our vertical. Um, the vast majority of our customers don't know who Sequoia, A-sixteen, Z, or any of those people even are, right? Um, and so I think that there's, 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, 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. You have a hundred billion, and if you put it all into the wrong things, that still goes to zero, right? 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, 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? So I don't really believe in those two. The third one migh…

AI assessment note: “More capital does not mean you run a better business.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q A couple of other people on that list and what they, what do you have next to them?

A 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 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 P zero, and then also there's a P zero zero, 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. 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 deal with the rest of the company.

AI assessment note: “I have Brian Halligan's on there, uh, and his is no.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q What do you think that time lag is? I know it's a horrible question to ask, but is it like a two to three year? Is it like a 10 year? You work with some of these enterprises. They don't speak the language that X and E generally do. What does that time lag actually look like?

A I think like three to five years until we see like massive, massive productivity gains in enterprise. I think the capabilities are there already. The capabilities were there two years ago. Right? Um, a lot of this is like, if you think about just like the average enterprise workflow, right? There's like, 17 different systems they're pulling data from to get that workflow done. Like literally, 17 might be on the low end. Sometimes it's like 50, right? And you have a hundred tabs open, you're opening in all these different apps, and they kind of connect to each other, they don't really connect to each other, right? And so the long tail on actually getting these systems And agents to do a task from start to finish is so difficult. And the problem that you're going to end up happening is you have these vertical companies building vertical agents like us and Sierra, et cetera. But a lot of even the verticals connect to all of the other parts of the enterprise. So like one thing that's happening that's interesting for us is, 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 actua…

AI assessment note: “I think like three to five years until we see like massive, massive productivity gains”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q seconds we've already done a sucker punch to Pat. But, but two, I, I just want to 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, because it's very revealing of his character. Can you tell me this story?

A 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. 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 going to run one mile no matter what. And then just kind of see if I can reduce the back end of the mile again, down, down, down, down, down, down until I can get to as fast as I possibly can. Um, and the, the outcome of that, which I think really helped was, and something I'm actually trying to do more and more in my life is every morning when I wake up, I get up pretty early and I just try to destroy myself and run as fast as I possibly can. 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. …

AI assessment note: “I remember when I started running a mile, I think I was at like eight minutes”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q simple. When people do what they said they'd do, generally they will continue to do what they said they would do. And I don't know if you're an angel in that many companies, but I'm an investor in a 170. Very few do what they said they would do and very few hit plan. So I totally get that. Do you actually believe that venture investors really move the needle?

A I think it really depends on who you get. I'll give you an example of something that I haven't trusted VCs as much with, and I think I've been right in some instances, wrong in others, is hiring. 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 caused 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, you know, executive. I'm not from the tech world. I don't know any of these backgrounds, right? And so I'll sometimes get intro to someone from a VC, and they have like 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 say …

AI assessment note: “I think it really depends on who you get.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I think a really interesting part actually is that Andrew Bielecki at Klaviyo, he made the decision to kind of go back to product 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?

A 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, 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, B to B SaaS or whatever, consumer SaaS, whatever you're doing, and what's different? And there are differences. And any VC who says that there are no differences, 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 want to 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 of years was product market fit. Then it was, 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…

AI assessment note: “A hundred percent. And I think, I think it's also a testament to something else”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Do you think we're seeing a plateauing in performance across the different model providers?

A 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 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 good. Like we're done. Like you don't need better reasoning to solve these problems. What you need is, like, different contexts. You need to connect to your calendar. You need to connect to, 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 going to keep going, and especially Cogen. I think we are not going to see a plateau in Cogen. I think that is going to get much better really, really fast.

AI assessment note: “we're seeing a plateau in performance for consumer use cases. On the enterprise, I think things are going to keep going”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Yeah. Which is a danger. Totally get that. Dude, we, we kind of bonded over the king making where I, where I, you know, said some things about king making and you said, that's not true. Why do you disagree with king making as a theory?

A Yeah, I mean, so I'll give you one example in our vertical. Um, the vast majority of our customers don't know who Sequoia, A-sixteen, Z, or any of those people even are, right? Um, and so I think that there's, 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, 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. You have a hundred billion, and if you put it all into the wrong things, that still goes to zero, right? 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, 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? So I don't really believe in those two. The third one migh…

AI assessment note: “I don't think capital makes folks win.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I had a conversation with, um, Are you going to make my girlfriend unemployed?

A 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 going to 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 want to 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 want to pay for that anymore, right? But there's all these new things that I'm paying law firms for, like, AI risk. 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 going to change it. There's so many new pieces of work for professional services that my gut is that's not what's going to happen. In fact, I think what's going to happen is the professional services market is going to actually keep growing 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 wor…

AI assessment note: “No. Um, I had a conversation, uh, with, like, a pretty large”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q lack of trust and trust issues, which was another one that I think it was Pat told me. I put one of your investors, but I'm going to throw him under the bus. I think it was Pat. Sorry, Pat. Pat did also say that you're an excellent deal guy, and I wanted to unpack that. What's your biggest advice on how to get the best deal and deal making?

A 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 y…

AI assessment note: “Maybe two pieces of advice. One is listen more than you speak”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q What bad habit do you have or do that you continue to do?

A One of the ones I have that I think was a good habit in the beginning of the company is now, and now it's 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 P zero, 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's 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 going to say who they are, but, um, They were saying that 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…

AI assessment note: “I zero out Slack, like, every, like, 15 minutes”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I think a really interesting part actually is that Andrew Bielecki at Klaviyo, he made the decision to kind of go back to product 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?

A 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, 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, B to B SaaS or whatever, consumer SaaS, whatever you're doing, and what's different? And there are differences. And any VC who says that there are no differences, 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 want to 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 of years was product market fit. Then it was, 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…

AI assessment note: “A hundred percent. And I think, I think it's also a testament to something else”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q simple. When people do what they said they'd do, generally they will continue to do what they said they would do. And I don't know if you're an angel in that many companies, but I'm an investor in a 170. Very few do what they said they would do and very few hit plan. So I totally get that. Do you actually believe that venture investors really move the needle?

A I think it really depends on who you get. I'll give you an example of something that I haven't trusted VCs as much with, and I think I've been right in some instances, wrong in others, is hiring. 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 caused 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, you know, executive. I'm not from the tech world. I don't know any of these backgrounds, right? And so I'll sometimes get intro to someone from a VC, and they have like 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 say …

AI assessment note: “I think it really depends on who you get.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q You said about kind of existential threats. Yeah. What existential threat today concerns you most?

A Yeah, um, I think just moving fast enough on product, like that, 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 50% 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, 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 going to solve later.

AI assessment note: “I think just moving fast enough on product, like that, that is always”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q What do you think that time lag is? I know it's a horrible question to ask, but is it like a two to three year? Is it like a 10 year? You work with some of these enterprises. They don't speak the language that X and E generally do. What does that time lag actually look like?

A I think like three to five years until we see like massive, massive productivity gains in enterprise. I think the capabilities are there already. The capabilities were there two years ago. Right? Um, a lot of this is like, if you think about just like the average enterprise workflow, right? There's like, 17 different systems they're pulling data from to get that workflow done. Like literally, 17 might be on the low end. Sometimes it's like 50, right? And you have a hundred tabs open, you're opening in all these different apps, and they kind of connect to each other, they don't really connect to each other, right? And so the long tail on actually getting these systems And agents to do a task from start to finish is so difficult. And the problem that you're going to end up happening is you have these vertical companies building vertical agents like us and Sierra, et cetera. But a lot of even the verticals connect to all of the other parts of the enterprise. So like one thing that's happening that's interesting for us is, 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 actua…

AI assessment note: “I think like three to five years until we see like massive, massive productivity gains”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I had a conversation with, um, Are you going to make my girlfriend unemployed?

A 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 going to 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 want to 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 want to pay for that anymore, right? But there's all these new things that I'm paying law firms for, like, AI risk. 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 going to change it. There's so many new pieces of work for professional services that my gut is that's not what's going to happen. In fact, I think what's going to happen is the professional services market is going to actually keep growing 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 wor…

AI assessment note: “No. Um, I had a conversation, uh, with, like, a pretty large”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q How do you assess the promiscuity of AI researchers? I mean, you know, poor old thinking machines, you know, uh, Home Alone is Mira Moratti now. Um, How do you assess that? Is that just a sign of the very bullion times?

A Yeah, I think there's a combination of things. I think the reality is what researchers care the most about is working on really hard and interesting problems, and I don't say that as, like, bullshit. Like, I think that there are sometimes, like, to your point of, like, people just want to join hot companies. Like, a lot of tech, I think, is, like, people just want to join hot companies, right? 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 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 going to 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 want to go work on.

AI assessment note: “what researchers care the most about is working on really hard and interesting problems”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q lack of trust and trust issues, which was another one that I think it was Pat told me. I put one of your investors, but I'm going to throw him under the bus. I think it was Pat. Sorry, Pat. Pat did also say that you're an excellent deal guy, and I wanted to unpack that. What's your biggest advice on how to get the best deal and deal making?

A 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 y…

AI assessment note: “Maybe two pieces of advice. One is listen more than you speak”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q That is absolutely amazing. Uh, listen, I want to move into a quick fire round. Um, what have you changed your mind on in the last 12 months?

A 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. 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 want to hit this amount of net new ARR, you need to hire this many AEs at this quota, and this is how long it takes to ramp them, so you need to 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 what have I learned in the past 12 months? Maybe it's more what have I learned in the past like 18, like 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.

AI assessment note: “I said earlier that a lot of company building has changed. I actually think a lot of it remains the same.”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q I heard from Lagora that the shared spaces was ripped from them. Is that fair?

A No. 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 going in 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.

AI assessment note: “No. We were working on multiplayer a long time ago.”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q in a way that like, no, no, really you do, and I, I love it, because it's like, I feel we got too kind in tact. Like, oh, we're all friends. That's like, no, we should be here to win. You know, for Slootman. Yeah. It's war. Love him. Yeah. Uh, and you guys really, it's wonderful to see the animosity and hatred, but do you guys respect each other?

A Um, I, I think, 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, and you know, this is back in 20, 23. We're, we're not that, I think they're like six months after us or something. 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, twenty-twenty-three, right? 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.

AI assessment note: “I definitely respect them. And I think like one of the things that they did”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q Um, do you think the economy is going to continue to explode? We have so much external concern outside of the X fear, which says like, hey, the circular deals are fucking nuts. You know, um, US borrowing has never been higher. Europe is a fucking museum that is completely unproductive. Um, beautiful. Um, uh, we are going to have a serious and material slowdown. Do you think that's wrong?

A 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 deep seek moment where like everyone freaks out, right? And I think we're, we're close enough to like an, an edge of, you know, 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 process 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 that.

AI assessment note: “I don't think it'll be this year.”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q I heard from Lagora that the shared spaces was ripped from them. Is that fair?

A No. 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 going in 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.

AI assessment note: “No. We were working on multiplayer a long time ago.”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q I do have to, as 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 Europe, but there's only so much you can do, blah, blah, blah. What do you know now about building teams in Europe that you wish you'd known when you started?

A Oh, I think that it's similar in Europe to where it is in a lot of places, which is you don't want to go into a country or a domain or anything like that and act like you know how to do something, right? Like you really need to partner with an industry or you need to partner with a geography, right? And so, and when I say, you know, we should have invested more in that, it's more like we didn't invest in it that much in 20, 23 and 24. 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 last year and the partnerships and things like that and how our product is localized for each geo is just a huge difference. But you can't do this from sitting in San Francisco and like kind of thinking about how to do it. You've got to travel.

AI assessment note: “you really need to partner with an industry or you need to partner with a geography”

Answered raw tape D 4 · C 5 · P 4 · Cm 4 4.30

Q 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. Um, he said, I want companies who have hostages, not customers. 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?

A Yeah, I mean, there's a third one that now develops, which is these AI products are so powerful, and I think over time the ROI is so high that 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 going to start aligning to that. And 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 going to work, right? Two things might happen. One, they might switch to fixed fees. Well, now we're good to go and efficiency is really good. I don't think it's going to happen that fast. The second thing that actually is happening, and we have so many law firm customers that have gained new business by building something custom in Harvey and saying, we'll do this 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 on the in-house side, it's even clearer. It's just if you save time, you'…

AI assessment note: “That's not a hostage. That's this product that I'm paying maybe like a million”

Answered raw tape D 5 · C 4 · P 4 · Cm 3 4.15

Q What bad habit do you have or do that you continue to do?

A One of the ones I have that I think was a good habit in the beginning of the company is now, and now it's 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 P zero, 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's 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 going to say who they are, but, um, They were saying that 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…

AI assessment note: “I zero out Slack, like, every, like, 15 minutes”

Answered raw tape D 5 · C 4 · P 4 · Cm 3 4.15

Q How do you assess the promiscuity of AI researchers? I mean, you know, poor old thinking machines, you know, uh, Home Alone is Mira Moratti now. Um, How do you assess that? Is that just a sign of the very bullion times?

A Yeah, I think there's a combination of things. I think the reality is what researchers care the most about is working on really hard and interesting problems, and I don't say that as, like, bullshit. Like, I think that there are sometimes, like, to your point of, like, people just want to join hot companies. Like, a lot of tech, I think, is, like, people just want to join hot companies, right? 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 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 going to 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 want to go work on.

AI assessment note: “what researchers care the most about is working on really hard and interesting problems”

Answered raw tape D 4 · C 4 · P 4 · Cm 4 4.00

Q I do have to, as 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 Europe, but there's only so much you can do, blah, blah, blah. What do you know now about building teams in Europe that you wish you'd known when you started?

A Oh, I think that it's similar in Europe to where it is in a lot of places, which is you don't want to go into a country or a domain or anything like that and act like you know how to do something, right? Like you really need to partner with an industry or you need to partner with a geography, right? And so, and when I say, you know, we should have invested more in that, it's more like we didn't invest in it that much in 20, 23 and 24. 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 last year and the partnerships and things like that and how our product is localized for each geo is just a huge difference. But you can't do this from sitting in San Francisco and like kind of thinking about how to do it. You've got to travel.

AI assessment note: “you can't do this from sitting in San Francisco... You've got to travel.”

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