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

I think the value of B2B SaaS is about to become astronomical. Do you think we're seeing a plateauing in performance across the different model providers?

I think that we're seeing a plateau in performance for consumer use cases. Probably what's going to happen is the economy is going to explode, and these companies are going to have crazy expectations for what they can do.

I think a lot of people in deals think that movement is action. No. The second piece is knowing when not to 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 want to hire somebody, hire them for 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.

Were you nervous pitching to Malcolm Bender? You knew them coming in?

Yeah, definitely.

What existential threat today concerns you most? 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.

Yeah, I know. If Pat's listening, he definitely needs to give some credit to Sarah here. Our first investor was OpenAI, and our first 2 angel investors were Sarah Guo and Elad Gil.

Dude, one, I love the way that under 30 seconds we've already done a sucker punch to Pat.

But two, I just want to start on something that shows a little bit about your character. 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 the story?

I played sports when I was in high school and then didn't as much when I was in college. When you start a startup, things get pretty stressful. I had a mentor who gave me advice: “Hey, stop lifting so many weights and start trying to run a mile.” I remember when I started running a mile, I think I was at 8 minutes or something. It was really, really bad; I was pretty out of shape.

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I basically had a goal to get up every single morning and just reduce my mile time as fast as possible. The way that I did it was, I'm going to run a 1-mile no matter what, and then just see if I can reduce the back end of the mile until I can get as fast as I possibly can. The outcome of that, which I think really helped—and something I'm actually trying to do more and more in my life—is that every morning when I wake up, I get up pretty early and just try to destroy myself and run as fast as I possibly can.

It reduces my stress for the rest of the day. I've found that, over time, a lot of company building is just making very good decisions. If you start your day off with something that is very challenging in a physical way, you have stress relief through the rest of your day. Your body has absorbed that stress.

I very much believe that in everything else, too. I try to do a stressful thing every week because I think a lot of it is stress tolerance over time.

Can I ask what decision you've made in your daily routine or life that has had the biggest positive impact? One for me is that I drink a liter of water when I wake up. It just makes me feel like I've accomplished something very quickly, and I'm hydrated fast.

Yeah.

Yeah, yeah. What would yours be?

I think it's getting up early. It's helped a lot. I think also we're in 60 countries now, and so no matter what, I try to keep basically East Coast time. When I'm in San Francisco, I'll get up at 4:00 a.m. or 4:30 a.m.

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What that allows you to do is focus before the stream of Slacks and the stream of emails come in. I think those couple of hours in the morning, especially when I can go to the gym and think about product and those things, have changed the trajectory of how I operate the company more than anything else. I do it when I travel, too.

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

One of the ones I have that I think was a good habit in the beginning of the company, but is now starting to get bad, is that I zero out Slack about every 15 minutes. I'm in almost every single Slack channel, and I read every single thing.

It was really good in the beginning of the company because if you do that constantly, every day all you have to do is catch up compared with what happened yesterday. It's really easy to make decisions. The problem with that is I've probably done it for too long.

As you scale, you actually have to focus more and more on what is the P0, right? I think I've done a little bit too much of still being in every single Slack channel and checking every little thing.

There was a time I was talking to someone from Sequoia, and they had been living with other founders during COVID. These are 2 very famous founders; I'm not going to say who they are. A lot of their routine was that they would just jump into random meetings at the company.

What they were doing was basically checking to see: How does this department do the sales call? How does this part of product create their PRDs and analyze their PRDs? How does this part of the company come up with OKRs or metrics?

I remember I left that dinner, and my co-founder and I were like, “Wow, those guys aren't working. That's so lazy,” and all this stuff. Now, when I think about those guys, I say, “Wow, they are incredible. 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 who are doing a really good job that they spend the majority of their time actually moving the machine.

You go back to being able to say, “I can focus entirely on product. I can focus entirely on what the most important things at the company are.” That's really what I'm trying to do this year: transition from all those heroics to building a really well-run machine.

I think the really interesting part, actually, is that [likely Andrew Bialecki at Klaviyo] made the decision to go back to product as a public company CEO and bring someone else in. Is that just a testament to the times that we're in—the importance of speed and product centricity, do you think?

100%. I think it's also a testament to something else, which is that these companies are growing so much faster than they used to. You have to get through a couple of stages, basically. I see Stage 1 as product-market fit. Stage 2 is company-market fit. In other words, have you created the structures of your company that are the same as traditional B2B SaaS or whatever consumer SaaS you're doing? And what's different?

There are differences. Any VC who says that there are no differences at this point hopefully has changed their mind. There are differences, and it's different based on what vertical and which company you're trying to build, right? 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? It feels like there's a cycle of doing that.

For us, and me personally, our first couple of years were product-market fit. Last year was company-market fit. I'm back to product-market fit again. What I spend a lot of my time on is the direction of our company and our product specifically for the next 6 months, year, et cetera.

You're at $190 million of ARR, you posted yesterday, and you raised at $8 billion. 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 analyze that?

We—it was funny. I think it was our offsite in 2024. I remember we kicked off 2025, and the first thing I did was go up and say, “Hey, we had a good year, but I'm pretty sure Anthropic's at about $3 billion in revenue right now, right?”

My point is the entire market is massive right now. I don't mean just the legal AI market. The AI market is exploding, right? 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?

The reality is that the market pull is massive. Sometimes your success isn't just your execution; it's the market pull. You have to benchmark yourself against other folks in the market—not just legal AI companies, but actually just AI adoption.

I also think that we're on an insanely compressed timeline. The winners and losers are going to be decided in the next couple of years in a lot of these spaces. 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—“we're done,” right? You have to instill this—

Yeah, well, Anthropic, you know, 10x, and they started at XYZ billions of revenue this year. $7 to $55, and then $55 to $190, say. And then you're going from $190 to—I'm a VC, so I can guess—but $400, $420, like 2, 2.5 times from there.

Our goal is much, much higher than that. I think we can do better than that this year.

Okay. So let’s say $500 million. And then I’m looking at that and I’m like, “Okay, then the $8 billion doesn’t feel too much.” Because the way that we think about it internally is: what’s end-of-year revenue, and then what’s the multiple on that end-of-year revenue? If it’s 20 to 25, it feels more reasonable. If it’s 100, it feels iffy.

Yeah, welcome to a Series A round. That’s what happens at Series A. That’s why it’s a bad place to be investing.

Okay, but you never got to a stage where you were like, “This valuation feels like we’re going to live into it. We’ve got to grow too much into it.” Which round felt the most uncomfortably high?

Uncomfortably high. Yeah, I think maybe the Series C felt very high.

And what was that?

I think it was $1.5 billion that we were valued at, and our revenue was definitely lower.

Lower.

I think maybe that was one of the ones that felt super high. The other ones haven’t.

Another thing, too, is that I’m very picky with investors, so I don’t spend tons of time fundraising. What I actually do is, there are a couple of 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 time to fundraise.” I reach out to literally 1 or 2 people.

And so, I plan my fundraises pretty far in advance. I’ll basically be like, “I know who I want to lead the next fundraise.” My point here is that, almost every single time, we probably could have gotten much higher valuations than we took. Instead, we chose the best investors—the ones that I trusted and personally wanted to work with.

What do you know now about fundraising that you think all founders should know?

Yeah, I think the main thing about fundraising is you should always think of it as: start it 6 months ahead of time, and you will do much less work than if you actually go out and do the process. What I mean by this—and I learned this from some other founders who are really good at this—is that they try to basically get folks to come in for a couple million dollars, just $1 or $2 million. You give them information rights, so you say, “Here, we’re going to tell you how we’re doing,” right? What you do with that is now they can check on the business, right?

The most important thing, at least that I have found—I think VCs care about this the most, and hopefully they do, because it would be a good thing if they do—is trusting that when founders say something’s going to happen, it’s going to happen.

I’ll tell you.

If you do that over enough time, hopefully VCs really trust you. Going back to that strategy, if you let them invest a little bit in the beginning and then you say, “Hey, in 3 months we’re going to do XYZ,” and then you say, “In 6 months we’re going to do XYZ,” and then in 9 months we’re going to do this, and at the end of the year this is what’s going to happen, if those things come true, they start to really trust you and believe you.

Then, when you go out to do that fundraising process, it can happen in 12 hours. You don’t need to make tons of materials. You don’t need to go out and do this massive process.

The problem with this is that you’re then not optimizing for price. That is assuming that you’re not trying to optimize price. What you’re trying to optimize is the partner. It’s much more targeted. You’re basically targeting a group of people and saying, “These are the people I want to work with, and I want to gain their trust, and then they’ll invest in me,” versus, “I’m going into the market, I’m doing this massive competitive process, and I want to maximize price.”

Totally get that. Rory O’Driscoll at Scale Venture Partners, who’s phenomenal—I love Rory, a dear friend of mine—says, “Harry, I’m not going to [__] it. I might do it again. Harry, when someone continuously hits plan, give them more money.”

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That’s good. And then that’s it. It’s very simple. When people do what they said they would do, generally they will continue to do what they said they would do. I don’t know if you’re an angel in that many companies, but I’m an investor in 170. Very few do what they said they would do. Very few hit plan. So, I totally get that.

Do you actually believe that venture investors really move the needle?

I think it really depends on who you get. But 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 and wrong in others—and that’s hiring.

The area where I’ve been wrong the most is when to hire a more senior exec. The VCs have been right. My partners have been right. 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. I think sometimes the problem that VCs have is they’re managed up, right? They don’t actually see inside a lot of these businesses. They see the board meetings, right? Sometimes the person who presents really well at all the board meetings or something like that, they think of as a really good executive, right? Then that person gets a reputation for being a really good executive.

I’m not from the tech world. I don’t know any of these backgrounds, right? I’ll sometimes get introduced to someone from a VC, and they’ll have an incredible background. I’ll be like, “That person didn’t seem very good.” It’s just my gut, right? I think I’ve been right in some of those instances, and I’ve bet on people who they sometimes said I shouldn’t have bet on, and they’ve turned out right.

When to hire execs, I’ve probably been wrong the majority of the time. Who to hire, I think I’ve actually been right a decent amount of times.

I think it’s actually a really smart distinction. I’m generally always wrong on who I suggest to my founders. Fair, in the benefit of hindsight. It’s like, “Nah, that wasn’t a good one.” Often, we just bring people who are actually too senior for the position.

That happens, too. Yeah, which is dangerous.

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Totally get that. Dude, we kind of bonded over kingmaking, where I said some things about kingmaking and you said that’s not true. Why do you disagree with kingmaking as a theory?

Yeah, I’ll give you 1 example in our vertical. The vast majority of our customers don’t know who Sequoia, a16z, or any of these people even are, right? I think there are maybe a couple of ways that people think about kingmaking.

First, they think of kingmaking as providing you with more capital. More capital does not mean you run a better business. You could have as much capital in the world as you want. If you make the wrong product decisions, you’re just going to invest in all the wrong places, and it doesn’t matter. It’s the same as VC. You have $100 billion, and if you put it all into the wrong things, that still goes to zero, right? I don’t think capital makes folks win.

The area where kingmaking—or where people think kingmaking matters—is customers, where they basically say, “Hey, this has branded trust, and so that is good.” I think there is a little bit of legitimacy there, but it’s not like only the top 3 VCs give you that brand. The vast majority of VCs give you that brand. What’s actually interesting for us is someone like EQT actually gives you that more than Silicon Valley because they’re private equity, and a lot more lawyers know who that is, et cetera, right? So, I don’t really believe in those 2.

The third one might be the 1 area where 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. We’re really bad at it. I can tell you a very clear reason why we’re bad at it: we still pay so much attention to someone’s résumé. We care so much about where they went to school, and this happens so much in technology. It happens a lot in tech.

The only other area where I know it happens an incredible amount is legal. Legal and tech are probably 2 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 the sense that 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, because the people who think about or go to a company because of the investors usually don’t care that much about the mission of the company.

My point with all of these things is there might be some short-term gains from 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.

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, but if I’m a GTM leader and I’m head of sales and I’m a machine and I’m here to get the number from 5 to 35 in the year and I’ve done the playbook 3 times, I’m going to [__] do it and I’m going to get my equity ramped. Do you care?

So, I’ll give you a good example of this. How many times a day do you think something goes wrong at Harvey? Quite a few. Constantly. 24/7. How many times a day do you think we feel like there’s an existential threat, right? Or, like, the big model providers are going to release something and maybe we haven’t released something.

All the time. Startups are very difficult places to work. You think from the outside, “Oh, wow, they’re 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.

It goes up and morale goes up and down, right? You face really difficult things, and then you have to figure out how to get through them. Being a missionary really does matter because the reality is, once you’re on the inside, the brand of the company and the success of the company matter less than when you’re on the outside.

It matters a lot on the outside because people looking in are like, “Oh my God, that’s the most successful. It’s super well-run.” All these things. 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.

You said something about existential threats.

What existential threat today concerns you most?

Yeah, I think just moving fast enough on product. That is always, I think, the biggest existential threat for all the application-layer companies.

It’s not necessarily that Anthropic or OpenAI are going to put 50% of their resources into the legal vertical or tax vertical or anything like that tomorrow. But they’re just improving their products and models, and the value of your product is going to go down unless there’s a massive delta between what your product does and what you could get from an enterprise GPT license, right?

It’s just a constant existential threat: How do you make sure you get to escape velocity on product, so you have enough of a product moat for them not to run you over? I think about that daily.

When I’m thinking about competitors, the main thing I think about is that I’m more bullish on these model labs than most people, I think. A lot of people are. I’m very bullish. They have incredible talent, and I think more about what the frontier problems are that our customers have that they’re going to solve later.

Opus 4.5 changed the game for Anthropic and changed the game for the landscape. Did you see usage shift entirely to Anthropic with that?

Not entirely, but there definitely was a shift. We route based on the use case to the best combination of models, and our traffic to Opus 4.5 definitely went up significantly.

Yeah. Is there a conflict with OpenAI when they’re an investor in your company and you’re suddenly routing the majority to Anthropic?

We aren’t routing the majority yet, but even if we were, there’s no conflict. Basically, they want us to win, and they want us to use the best model, right?

There’s nothing in our agreement or our relationship or anything like that that says you have to use OpenAI models. If anything, getting feedback from application-layer companies on where their models aren’t doing as well, where their models perform super well, and where they need to improve is super valuable to them.

Do you think we’re seeing a plateau in performance across the different model providers?

I think that we’re seeing a plateau in performance for consumer use cases. The reason why I think this is a misnomer, or something that people actually shouldn’t pay attention to, is that we don’t need them to be better for consumer use cases. A lot of the consumer use cases—four was good, we’re done. You don’t need better reasoning to solve these problems.

What you need is different context. You need it to connect to your calendar. You need it to connect to all of the different apps that you use and things like that. That’s what an increase in performance is for them, right?

So, I think there might be a plateau on some of the consumer-facing side of things. On the enterprise side, I think things are going to keep going, and especially code generation. I don’t think we’re going to see a plateau in code generation. I think that’s going to get much better really, really fast.

What do you expect to see in code generation in the next 12 months?

I think the slope will only increase. I think that it will get better and better and better, and I think that will unlock a lot of productivity across the entire world.

When you look within Harvey, is everyone using Claude Code, not Cursor?

It’s a combination. In the UK, we have a game called “Shag, Marry, Kill.”

Yeah.

I’m not going to do that here because it’s wildly inappropriate. But if we were to do “buy and sell,” and you had Anthropic at $350 billion and OpenAI at $800 billion, which one would you buy and which one would you sell?

Yeah, I know. I know we talked about this. I’d buy them both at double.

You’d buy OpenAI at $1.6 trillion?

Maybe not quite $1.6 trillion. There are a couple of things I need to see from them before I would do $1.6 trillion.

What do you need to see from them before then?

I think the main thing with OpenAI is that they have so much consumer brand. It is so powerful, and especially outside of X and outside of our worlds, it is so unbelievably powerful.

I don’t come from the tech world, and all of my friends and all of my relationships before this were outside of tech, right? That brand power is incredibly powerful, and I think more focus on consumer and just tripling down on that is where I’d be the most bullish.

I think that on the enterprise side, there will be multiple winners. Enterprises don’t allow there to be 1 winner, right? So, no matter what, OpenAI is going to get some of the enterprise market, and Anthropic is going to get some of the enterprise market. But in the consumer market, I do think OpenAI has an opportunity to take a lot of this. Obviously, the main competitor there is going to be Google, right? But I think they both can be astronomically huge companies.

The other thing that I feel like folks don’t realize is that everything could pause. 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.

We’re so far from the ability of the models right now being integrated into daily life. People do not know how to use these systems. Consumers don’t, and businesses definitely don’t, right?

The capability overhang is so high. I think it’s higher than anyone is even talking about. It’s astronomical. If both companies literally just stopped shipping things, their revenues would still explode because there are going to be so many companies building on top of their models. There are going to be so many different parts of the economy that adopt these things that I think we’re still in the early days.

What do you think that timeline is? I know it’s a horrible question to ask, but is it a 2- to 3-year timeline? Is it a 10-year timeline? You work with some of these enterprises. They don’t speak the language that X and we generally do. What does that timeline actually look like?

I think 3 to 5 years until we see massive, massive productivity gains in enterprise. The capabilities are there already. The capabilities were there 2 years ago, right?

A lot of this is, if you think about just the average enterprise workflow, there are 17 different systems they’re pulling data from to get that workflow done. Literally, 17 might be on the low end. Sometimes it’s 50, right? Then you have 100 tabs open, and you’re opening all these different apps. They kind of connect to each other; they don’t really connect to each other, right?

The long tail on actually getting these systems and agents to do a task from start to finish is so difficult. The problem that you’re going to end up having is that 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.

One thing that’s happening that’s interesting for us is that a lot of our revenue is starting to come from Global 2000 or Fortune 500 companies. We actually haven’t built many features for tax compliance and procurement, right?

What’s starting to happen is those departments are adopting Harvey even though we haven’t built features specifically for those departments. The reason why is that the legal department actually interacts with all of these different parts of the business. Legal documents are such a core part of a business that they interact with all of these different parts of the business, right?

We released a feature that’s multiplayer. It’s called Shared Spaces. At first, a lot of the impetus for doing it was that you want a large corporation, like Walmart or whatever, to work with their law firms in the same platform. That’s happening.

But actually, what’s starting to happen is that the legal team is working with the compliance department, is working with HR, is working with everything else, all in Harvey at the same time.

I heard from Legora that Shared Spaces was ripped from them. Is that fair?

No. We were working on multiplayer a long time ago.

One of the things that’s interesting about our company is that we started with the hardest customers. We did the same thing on the in-house side, too. We had bank customers a while ago, right?

The security and permissioning systems that you need to build for a bank are so much more in-depth, and the enterprise-readiness requirements are so much greater than for a lot of the other folks.

And the biggest problem with multiplayer, in the way that we’re doing it, is that we’re allowing the in-house side to kick it off, or the law firm side. To do that, the security and permissioning that you needed in place for both are astronomically high.

We were working on this for a very, very long time. We were going for six months to almost a year. We did all the permissioning and all of that stuff first before we did the UI on top.

Why do you think they continuously say that you ripped that product idea, then?

I think that if you’re number two in the market, one of the things that can get you a lot of attention is attaching yourself to number one in any way, shape, or form, right? You get free press from doing that type of thing. It’s a good way to basically jump onto the distribution that the other firm has.

Do you respect them?

Yes.

You hate each other in a way that—no, no, really, you do. I love it because I feel we got too kind in tech. It’s like, “Oh, we’re all friends.” We should be here to win. You know, Slootman. It’s war. Love him.

You guys really—it’s wonderful to see the animosity and hatred. But do you guys respect each other?

I definitely respect them. One of the things that they did really well—I think they did a great job in Europe. This was back in 2023. We’re not that far apart; I think they’re about 6 months after us or something. It’s not that big of a gap.

One of the things that I would have done differently in the beginning is invest more in Europe in 2023. A lot of our first customers were in Europe, right? Having folks on the ground here is really, really important, as is respecting the different cultures and how to productionize that and all of those things.

Why did you not, out of interest, come to Europe earlier?

It was just bandwidth. When we signed [likely A&O Shearman], which was our first customer, we had 4 people. We did a 4,000-person, enterprise-grade rollout with 4 people.

Was this when you were—I got told this from Pat—you were in an Airbnb?

Yeah, we were in an Airbnb. The engineer who had joined, who was our first engineer, Gabe, was basically coding everything before that. He had been there for, I think, a month, and then we onboarded a 4,000-person, very large-scale enterprise where security was incredibly important to the team. So it was just bandwidth. When you’re scaling that quickly, it’s harder.

Are you shitting yourself that the platform’s going to fall over?

Not anymore.

Not now, but back then in 2023, with one person in an Airbnb.

But actually, I think this is important. This is something that’s interesting. When I look at a lot of AI application-layer companies, if you go through their LinkedIn profiles and look at the engineers they’re hiring, it’s 90% front-end engineers.

Which is interesting to me. A lot of the reason is I think vibe coding works much better with front-end than it does for infra. A lot of what’s happening to AI companies, or is going to happen to them—and it happened to us in early 2024—is you do a bunch of front-end and make really pretty UIs and really nice demos, right? You use that to land all the customers, and now you have a lot of actual, active customers, but you haven’t invested in the architecture and infrastructure for hundreds of thousands or millions of customers using your product.

We kind of made that mistake in 2023. In the beginning of 2024, something that slowed down our shipping velocity was that we had added tens of thousands of users in the Q4 before that, and we didn’t quite have the infrastructure to support them.

Now, if you look at our team, almost 40% of our entire EPD organization is made up of very senior infrastructure engineers from Databricks or somewhere like that. It’s a long-term bet that, as you get these agentic systems processing tens of millions—for us, I think last year we did almost half a billion documents or something like that—you need the infrastructure to actually support it.

It’s not just about how you win the demo and how you win the deal, but how you actually create very scalable enterprise infrastructure for your product. I see a lot of AI application-layer companies not doing this.

If you were advising those founders, would you say, “Hey, really focus on prioritizing infra hiring earlier, so you’re able to fulfill what you say you will do”?

What I would tell them, actually, is that your GRR matters. One thing that a lot of investors in the AI space have not been paying attention to is GRR. They’ve basically just been looking at net-new ARR and being like, “Churn is fine because they’re going so fast that maybe they’ll pivot or they have some customers.”

5. Cold Emailing OpenAI and It Leading to a Term Sheet

I think that’s a huge mistake. You’re going to see a lot of companies in a lot of verticals 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.

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 company customers really, really fast. I see a lot of AI companies not focusing on this, and I think that’s going to be a huge reckoning for people once they get past 100 million ARR.

This is what I worry about: when you look at GRR figures and think about Sierra, the growth is amazing and it’s the best of the best. Jesus, take my money too. But I’m not questioning you; I’m like, gosh, what you now have to fulfill from a per-customer implementation service-provider aspect to go from 100 to 400 is a lot.

Yeah.

A lot. A lot a lot. It’s not like a plug-and-play. It’s much easier to go on the consumer side from 100 to 400 with a PLG motion.

Yes, I agree, and I think what that requires then is going back to what we were saying: how do you go from product-market fit, and then how do you get company-market fit? That’s actually about how you structure your company.

Part of that is different from how it used to be in the past. If you have long implementation cycles, one thing that’s going to end up happening, I think, is that a lot of these verticals are going to land at a big Fortune 1 or Fortune 2 or whatever. Their product is going to expand massively.

This is a really interesting thing about Microsoft and Salesforce. I don’t know how much you know about them, but they started in the beginning with the vast majority of their sellers in pre-sales, right? Spear fishermen. You have tons of that, right? Old-school spear fishermen.

They eventually migrated to having a lot of what they have be post-sales. A lot of their investment is actually in post-sales. The reason why is because their customers’ NDR goes up, up, up, up, up. They keep buying more things; they buy more compute, et cetera.

I think a lot of these enterprise companies should start thinking about their company that way. There’s some kind of a land grab right now, but really what’s going to matter is, if you are bullish on AI, you should be bullish on your product—the value of your product.

We are in day 1 of product development, right? It’s going to change astronomically. What’s more important than landing new customers and getting really high ARR is whether you can retain those customers, because that customer that pays you $1 million today could pay you $100 million at some point.

I think Databricks is a company that’s done an incredible job of this. I had Alex Rampell, who’s obviously at Andreessen, one of your investors, on the show recently, and he said something I loved. It sounds a bit awful, but I loved it. He said, “I want companies who have hostages, not customers.”

Okay? Again, as bad as that sounds, I did like it. In this space, are they hostages or customers? How easy is it for them to move?

Yeah, I mean, there’s a third one that now develops, which is that these AI products are so powerful, and I think over time the ROI is so high, that your ROI can become so massive that it’s less of a hostage and 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. I think more and more companies are going to start aligning to that.

I’ll do the law firm side and the in-house side. For law firms, they bill by the hour, so a lot of people are like, “How could you ever sell to them? There’s no way that this is going to work,” right?

Two things might happen. One, they might switch to fixed fees. 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’s actually happening is that 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 a product that I’m paying maybe $1 million for a year that just earned me a deal worth $20 million. What is the ROI on that? Incredible.

On the in-house side, it’s even clearer. If you save time, you’re saving tons of money.

So 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. If you can figure out how to align your product to that ROI, it's not a hostage; you're just completely aligned with your customer.

How do you align your product to ROI when your customer base doesn't want to pay for a consumption model, and they just want to pay for a seat model that they know and can rely on?

6. AI's Impact on Professional Services

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

There's this Irish guy whom I quote so often. He's brilliant. He should basically just replace me at this point. He's much smarter than me. But he always says that AI will be magnificent for us all if we see spend shift from human labor budgets to technology budgets. Will we see that shift here?

Already seeing it happen.

How does that happen?

Yeah, so there are a couple of companies that have basically said that the Harvey budget comes out of their spend on professional services, not out of their tech budget. The budget for professional services is in the billions a year, versus the tech budget for that G&A group, which is astronomically smaller. Sorry, the professional services budget is not the G&A talent that they have in their organization.

7. Future of Law Firms: Do They Die?

And I think that's what's really interesting about our business: a lot of the work that we're doing for a corporate is not the work that our law firm customers are doing. It's alternative legal service providers. It's this lower-end work.

What percentage of revenue is law firm versus external?

Right now—oh, you mean corporate versus law firm? I think it's around 40% of our revenue in in-house corporate and 60% is law firm, something like that.

Wow, 60% law firm, 40% Fortune 500 companies. Is that what you thought it would be?

I think something like that. If you just look at the breakdown of how many lawyers exist on Earth and how many of them are at law firms versus in-house, that's pretty much the same.

And in 5 years' time, what will that be?

I think it'll be similar. I think it'll be the same.

Got you. How will we see law firms change? Will we have a kind of cannibalization of juniors?

I don't think so. I think we'll just get more work.

Are you going to make my girlfriend unemployed?

No. I had a conversation with a pretty large private equity shop recently, and they were talking about how their year is going to be incredible. They think it's going to be a big M&A year. It's going to be great.

They were talking about how they think about legal fees. The way that they thought about legal fees is, the reality is, it's going to be a big year, and whenever we have a big year, we pay more in legal fees. That's just how it happens, right?

But there are certain things I don't want to pay for anymore. There are certain parts of the deal, et cetera, like marking up NDAs, whatever it is. I don't want to pay for that anymore. But there are all these new things that I'm paying law firms for, like AI risk: should you buy this company? Is there a problem in XYZ country with an act or something like that that's going to change it?

There are 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 keep growing at the same rate as GDP.

One way to think about this is that most professional services are cyclical. If you have a really good year, professional services have a really good year. That's almost always how it works. Other than bankruptcy, and litigation is somewhat countercyclical. It depends on the area.

I think people think about this and they're like, "Oh, wow, AI is going to impact legal and it's going to just destroy all these jobs." The thing they aren't thinking about is that all of their customers are using AI to create more products. What happens when you create more products? You need more product legal advice. What happens when you're expanding into other countries faster? What do you need? Regulatory advice, right?

I think people are thinking about AI in all of these industries as a vacuum. The reality is, you should think about AI as the entire economy. What's going to happen? Probably what's going to happen is the economy is going to explode. These companies are going to have crazy expectations for what they can do, and the professional services providers are going to have to respond to that.

Do you think the economy is going to continue to explode? I can't believe I'm asking this question because it feels like the most basic question that [__] interviewers ask, but maybe I'm just a [__] interviewer at this stage, to be honest.

We have so much external concern outside of the AI sphere, which says, "The circular deals are [__] nuts. US borrowings have never been higher. Europe is a [__] museum that is completely unproductive." Beautiful. We are going to have a serious and material slowdown. Do you think that's wrong?

I don't think it'll be this year. I think there will be bumps. I definitely think we'll have more moments like the DeepSeek moment, where everyone freaks out.

I think we're close enough to an edge where, if enough people say that there's going to be a bust, it's pretty easy for one thing to happen, for everyone to freak out, and for there to be a bust. It's a self-fulfilling prophecy. Those are usually pretty short.

I think that we will have a bunch of short ones, but long term, AI is going to completely reshape every part of the economy. I very strongly believe that.

8. What Everyone Should Know That No One Tells You About Hiring in Europe

As you mentioned Europe, and we spoke a little bit about Europe's productivity there, you said you wish you'd 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?

I think it's similar in Europe to where it is in a lot of places, which is that 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. You really need to partner with an industry, or you need to partner with a geography.

When I say we should have invested more in that, it's more like we didn't invest in it that much in 2023 and 2024. We invested tons last year, and we're investing even more this year, and the difference is pretty massive.

The difference in the quality of our team last year, 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 thinking about how to do it. You've got to travel.

What's the biggest difference in talent between the US and Europe?

I think the biggest difference isn't a difference in talent. It just takes a long time to hire people, and so you have to think about it with a way longer time horizon.

Because of gardening leave?

Yeah, it's just really hard to hire people. That was interesting to me, or something that I wasn't used to, whereas in the States, you can hire someone and they start quite literally the next day sometimes. Or if they have to give 2 weeks' notice, they start exactly 2 weeks later.

That allows you to be a little bit more like, "I quickly need to hire this." Retroactively, I can fix a problem. In Europe, you have to plan out more.

We've done a lot of really big office openings. We just announced Paris and Dublin and a bunch of other ones. But you have to think about this stuff at a longer time horizon. You can't do it instantaneously.

Is the US trope of Europeans not working as hard fair?

That's not what I found, but I will say we interact—I interact mostly with lawyers. Lawyers have billable-hour targets, 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. There are so many incredible, hard-working lawyers.

UK lawyers work pretty hard.

UK lawyers work insanely hard. It might be that I don't notice it as much because of the domain that we're in. They work the same across the globe. Lawyers are just incredibly disciplined, hard-working people.

In terms of people assessment, Pat told me that you're well-versed at understanding people. If I were to ask you for a trait that you look for in someone joining Harvey that's less obvious than the foundational integrity or high ambition or [__] that you normally get at—like, I look for obsessed psychopaths—

That's a good one. You definitely need to be obsessed.

What would yours be?

Obsession is definitely very important, but the one that I look for right now a lot is ownership. It's really, really important.

There are a bunch of different ways that you can assess this, but over time, you start to be able to read if someone actually can take ownership over something or not. The reason this becomes really important is that as you scale as a company, it becomes really hard to figure out where a problem is stemming from.

It becomes hard because this is how it ends up going: It used to be that I knew every single thing that was going on in a company, and I could just be like, “Hey, that’s where the problem is. I’m going to unblock that,” right? Now we’re getting to the point where I know most of what’s going on at the company, but sometimes something is so low down that I don’t know what the problem is. If I ask 5 people, they’ll all do this. It’s like the Spider-Man meme, right? And what I have found is—

That’s like bad deals in venture firms. Who did the deal?

Yeah, and it’s just like—it’s all over the place.

Yeah, exactly. It was Johnny. He left.

And I don’t know. I have found that there are a lot of people in tech who have done a really good job managing up. They have ridden a wave of their team’s success without being successful themselves. So, the thing that I look for a lot is: can people admit their mistakes? To me, it is so obvious when someone is actually admitting mistakes versus saying that one of the biggest things they’ve done wrong is actually something that’s really great, right?

Let’s go back to something you said earlier, when you said some of the things are bad habits that you’re trying to improve—

Yeah, yeah.

And you said checking Slack too much.

Right, right.

That, I think, is a good example. If I’d interviewed myself and I saw that as a question, the way that I answered it, the way that I would push on this is, I would say, “Why do you do that?” Why do you do that? And my genuine answer to that would be, “I have trust issues.” It is hard for me to trust that somebody else is going to handle that problem.

And now, all of a sudden, it actually is ownership. That is an actual problem of being a leader. 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?

9. I Have Massive Trust Issues…

Why do you think that comes from? I have trust issues because I found that generally, when relationships break down, it always comes down to them extorting me for money.

[laughter]

Great. It’s true. Yeah. I think my trust issues—I think part of it is it’s hard to tell whether it’s nature or nurture, right? But I think that I definitely had some problems with authority when I was younger. I had a not-the-normal-Silicon-Valley kind of background and upbringing. Because of that, I really went out on my own at a pretty young age and was pretty independent.

I think that one thing that you have to learn when you’re leading a company is that you are a leader and a partner to the rest of your team. It’s not just you. I am not Harvey. Harvey is not me. It’s 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, “I want to be number 1.” I think of this as a sports team. There are people I know who don’t care about winning the championship. They want to be the person who scored the most points, and they’re okay with losing the championship as long as they’re the one who scores the most points.

Those are the exact type of people that I do not want to work with. I want to work with people who do care about how many points they’ve scored, but they care about that because they helped win the game, right? I think that’s a huge problem in tech: we have too many people where it’s me, me, me, me, me, and not company, company, company.

So, God, I think the US is just full of logo chasers. There’s a lot of that. You guys just love to work at a hot company. It’s the hot-company hopper, I call it. Whereas they just go 2 years, 2 years, 2 years, 2 years, and it’s like they’re doing venture portfolios with company equity.

Yeah, and it’s just like—

I was about to say VCs and things.

And I sit in these operator groups, and they’re like, “Ooh, I hear Clay’s really hot.” Or, “Ooh, I hear Notion’s really hot.” And they just jump. I think the promiscuity of American operators is incredible.

But, but, but, look at—

Brits are too negative with, “That’s crap.”

Don’t be a dick.

[laughter]

Yeah, I think this also—I forgot who tweeted this. I don’t remember who it was, but this was at the end of 2022, right after the ChatGPT launch. Someone—I forget which VC did this, so sorry for not giving credit to them—basically tweeted, “My prediction is what’s going to happen is a lot of VCs, because they don’t understand the AI ecosystem, are going to revert back to looking at resumes because they don’t understand.”

This is what people do when there are situations of chaos and folks don’t know what’s going on: the safest thing is to go look at other social signals to make decisions instead of using your own gut. I think that’s happening a lot in AI, and hopefully, as the markets mature, this stops happening. But there’s a lot of, “I don’t really understand this, and so what I’m going to do is look at the resume, or look at a logo, or look at that, because that seems like a safe bet.”

How many truly great researchers do you think there are?

Hundreds, and that’s it.

How do you know a good researcher from a resume?

I don’t think you can. That, I think, is actually a pretty big disconnect. The researcher community knows. This is a huge disconnect between VCs, I think, and the researcher community.

So what would you advise me investing?

What I would do is use the researchers to pinpoint who the best researcher is. In other words, if you ask a bunch of the researchers—not other VCs—who they respect the most, they have such a tight-knit community, and it’s all merit-based.

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. Because of that, if you ask that community who the best folks are, they will triangulate for you and help you find them. Usually, it’s not the loudest. They aren’t necessarily the most famous, et cetera. It’s not like that.

How do you assess the promiscuity of AI researchers? I mean, I hear poor old Thinking Machines—how alone is Mira Murati now? How do you assess that? Is that just a sign of the very brilliant times?

Yeah, I think there’s a combination of things. The reality is that what researchers care about the most is working on really hard and interesting problems. I don’t say that as bullshit. I think that sometimes, to your point about people just wanting to join hot companies, a lot of tech is people just wanting to join hot companies, right? Researchers really genuinely do care about pushing research forward.

What ends up happening sometimes is the leaders at some of these companies change the direction of the company, and the researchers are no longer interested in that direction. That happens a lot at these big labs. They’re making multiple bets in multiple places, and what ends up happening is 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, 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. 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. They’re in insanely high demand. They’re able to pick what projects they want to go work on.

How bad is the war for talent? You’re in the midst of it.

Yeah, it’s incredibly high. One thing to bring up is that, over time, we have this interesting thing where a lot of the AI companies—application-layer companies, including ourselves—in the beginning were like wrappers, right?

What’s going to happen over time is these companies are going to do 2 things. One, a lot of the core software that they build isn’t even going to be AI-related. It’s just core software building, and that’s actually going to be much more differentiated.

The second thing that’s going to happen is that none of these companies have access to proprietary data until very recently, right? A lot of what we’re looking at is: how do you actually create custom solutions for a large enterprise? Those are AI problems again, right? So now we’re all the way back to AI actually mattering.

10. Biggest Lessons on Effective Deal-Making

I think what we’re going to see is that the main problem—a lot of these companies haven’t hired any AI talent. A lot of what they’ve done is the model is basically the entire product. As these companies scale and have to create more differentiated products, I think having AI talent is going to matter again. We’re just now getting to the size of the company where we can hire the people that we need to do a lot of that frontier work.

We talked about assessing people’s skills in terms of the talent there. We talked about your lack of trust and trust issues, which was another one that—[laughter]—I think it was Pat who told me. I put one of your investors—I’m going to throw him under the bus—I think he’s perfect. Sorry, Pat. Pat did also say that you’re an excellent deal guy.

Mhm.

I wanted to unpack that. What’s your biggest advice on how to get the best deal and deal-making?

Maybe 2 pieces of advice. One is: listen more than you speak. It’s very, very dumb, but it’s true. I think a lot of people in deals think that movement is action. They think that movement is progressing the deal forward, and they think that if they talk the most, they’re in control of the deal. That’s not true.

In the same way that, in conversations, just because someone isn’t participating in that conversation doesn’t mean that they aren’t listening. It doesn’t mean that they have the upper hand or something like that. I think listening is really important, and I see a lot of folks think of deal-making as chest forward: if I’m the loudest and I’m saying the most. The reality is that all deal-making is just people reading. That’s it.

It’s people reading at scale. It’s reading a 1-on-1 conversation, then reading groups of people, then reading entire verticals of people, et cetera, and figuring out what they want. The second piece is knowing when not to negotiate. This, I think, is actually really, really important, and the best deal-makers I know are very good at this.

There are certain deals where you want 1 thing from the deal, and nothing else matters. This only works when you understand the value of something more than everyone else does. If you understand the value of something more than everyone else does, throw all of your principled deal-making aside. You’re supposed to negotiate X and then Y, and then it’ll be 50% in between, and all of that—that’s all [expletive]. Throw that aside and get the thing that you know is more valuable than anybody else does done.

I know a lot of people who are the best deal-makers I know—the best—and they know that very well. A lot of what you’re doing, I think, and I think Sam Altman is incredible at this, is holding multiple ropes. You have 17 ropes in this hand, 17 ropes in this hand, you’re grabbing all these ropes. At some point you’re going to get pulled apart because it’s too much pressure and you’re going to lose. What you do is get good at tying off one of the ropes. Then that pressure’s gone and you have one tied. Then you tie another one and you tie another one and you tie another one. Tying those ropes allows you to pull more ropes. That’s a lot of how I think about deal-making. Another company that has done an incredible job of this is Microsoft. They’ve created this partnership ecosystem. A lot of people have given them flak: Why do you let people do XYZ partnership? Why do you let people build on this? They’re just going to take it. It’s very clear that Microsoft has actually won in a lot of areas because they’ve decided to partner with kind of everyone instead of saying, “Ah, no, brass tacks. We’re going to be very tough on this.”

I think one actually also is when you hire people and they say that they want $75,000. So often I meet founders and they’re like, “Ah, but I got them down to $70,000.” And I’m like, “Give them $75,000. Day 1 they start, they feel valued.”

With hiring, this is a huge mistake that people make. Massive mistake. If you want to hire somebody, hire them for whatever they want to be hired for, and put them in the position that they want. If they’re best in class—if you can’t tell whether they’re best in class, that’s a separate problem—but don’t go back and forth. It doesn’t matter.

One of the most valuable bits of advice Josh Kushner actually gave me—I love him—is that if you’re willing to take less, don’t do the deal. Imagine I’m a VC and it’s like, “I want 10%,” and you’re like, “I can only give you 7%.” I’m like, “I’m actually fine with 7%.” Well, then you don’t believe in that company. That’s not going to be a legendary, category-defining company.

100%. Agreed. You said something about people and reading people in a deal. When did you most misread someone, and how did that shape your mindset?

I think one of the things that I’ve done wrong in the past is that I thought someone couldn’t scale because they had bad communication skills. I misread that, and I didn’t realize how easy it would be for them to learn how to do it.

I think that sometimes, because I do a lot of in-person interviews and a lot of those things, I end up making the mistake of reading too much on the surface and not going deep enough. I think I’ve gotten better at it, but that’s one of the things that I’ve done with hiring.

I’ve fallen for the résumé trap, too. I’ve definitely fallen for it, and I think that’s a huge mistake.

You mentioned OpenAI and Sam as the deal-maker as well in this different kind of area. I heard that you cold-called Sam in the summer of 2022. Can you tell me about that before we do a quick-fire round?

Yeah, so it wasn’t a cold call. We cold-emailed them. We cold-emailed Sam Altman and Jason Kwon.

What we’d basically done was gone on r/legaladvice, which is basically a subreddit for asking real questions. We grabbed a bunch of those questions, ran a chain-of-thought prompt that we had basically built on top of it, and gave it to a bunch of landlord-tenant attorneys. Then we basically said, “Look at these questions and tell me if you would send the answer.”

We didn’t say anything about AI to the consumer who asked the question. For 86 out of 100 questions, the attorneys said they would send the answer. We cobbled all that together and sent a cold email to Sam Altman and Jason Kwon.

The idea was basically, “Hey, did you guys know that, at this point, it was GPT-3 and the API was public? I think at the end of 2021 or beginning of 2022 they had an API. Did you know it was this good at legal?” That was it.

The subject line of the email was basically, “Did you know it was this good at legal?” We met them pretty recently after that.

How did that go?

It went well. We had a call with Jason first and talked about our strategy as a company and what we would build. Then we had a final pitch to the rest of the OpenAI C-suite, actually, on the morning of July 4, 2022. It was around 11:00 a.m. on July 4, and we did a pitch to the rest of the company.

Do you get nervous before these? When you go into Sequoia and pitch the partnership, that’s nerve-racking.

Yes. I had a weird thing where I didn’t know who any of these guys were.

It’s so funny because, for me as a venture nerd, I’m like, “Holy shit, I know everything about everyone.”

Now I do, but back then I didn’t know anything. I didn’t even have friends in tech. When we did our seed, we didn’t go to anybody else; it was just OpenAI.

How much did they invest, and for how much?

The actual terms, I don’t remember what the post-money actually was, but the pre-investment was like $4 million or something like that.

VC meetings: how many term sheets did you get?

For that, I don’t remember. It was, I think, like half or something like that.

Which was the worst—the worst term sheet or the worst meeting?

Worst meeting.

Oh, I’m not going to say that publicly. The worst one?

There was one.

Why was it bad? Just tell me that.

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. They didn’t even make eye contact—literally zero. They were just taking notes.

Yeah, they were taking notes.

No, I think they were texting a friend: “Can’t believe this knob is still talking about legal.”

Here?

That was the worst one.

11. Quick Fire Round

That is absolutely amazing. Listen, I want to move into a quick-fire round. What have you changed your mind on in the last 12 months?

I said earlier that a lot of company-building has changed. I actually think a lot of it remains the same. There are a lot of core first principles of scaling a company that I’m much more focused on now, which I wasn’t focused on in the beginning. I’ll give you the dumbest example ever.

For the first 2 years of the company, when I was doing revenue projections, I never—and this is embarrassing, really embarrassing—I never thought, “If I want to hit this amount of net new ARR, I need to hire this many AEs at this quota, and this is how long it takes to ramp them. So I need to have hired them by this point before I do that.” I’m dead serious. I never even thought about that, right?

These are really core laws of physics about companies that remain the same. There’s no difference in AI. Maybe what I’ve learned in the past 18 months—the second half of the company, basically—is how much of the company building is actually the same. I probably should have listened to people a little bit more about that.

You have Sequoia and a16z on the cap table. How are they different to work with? I’m not asking whether one is better or worse, but how would you say they’re different to work with?

I think there’s obviously a difference in scale, right? a16z is just a lot, a lot bigger. I would say that a16z is also louder, right? They’re a little bit more in these other regions and other areas and things like that, whereas Sequoia is just a different style. It’s closer; there aren’t as many partners and things like that.

Were you nervous pitching to Marc and Ben? You knew them coming in.

Yeah, definitely. I’ve always been nervous. One thing, too—I think I said this earlier—I think Keith Rabois says this, who I’ve actually never met in person.

There are a couple of people I have a list of, actually, at the top of my operating doc. I have a list of people, and they all have 2 words next to them: the thing that I’ve learned from them or something like that. I’ve never actually met Keith Rabois in person, and I think he’s an investor in one of our slight competitors.

Spellbook. Yeah, yeah, yeah.

We don’t compete with them tons, but in some degrees we do. Anyway, one of the things I think he was talking about at some point is how important it is that you should be constantly stressed and do things that make you stressed every day. I strongly agree with that. I really agree with that.

I think the times that I’ve stagnated, or the company has stagnated, are when I don’t have something every day that’s really stressful. The weeks that I do the best work, or feel like I did the best work, are when every single night before I go to bed I’m like, “Oh, shit. Tomorrow is going to be—there are so many things. Everything needs to go right. I’m really stressed.” It’s massively compounding for you as an individual to just put yourself through that stress.

I freaking love it. I tweeted, “Hey, if you are ambitious and you want to learn about working in AI applications, there’s no better place to work than Harvey.” Keith Rabois. Hmm.

[Laughter] No. I mean, it’s interesting. I think Pat also has this, too, and all of my VCs do. In particular, he really thinks of constant, relentless application of force—that’s what he says—and that’s actually what I have next to his name.

That’s incredibly important. If you lose that as a company, the company is pretty much over, right? You as a founder need to constantly, constantly be applying force, and it starts with applying force to yourself. If you aren’t applying force to yourself, you don’t have that ownership mentality, and you’ll start to get weak. I think that will trickle down through the rest of the company.

Who are a couple of other people on that list, and what do you have in mind as to them?

[Laughter] Brian Halligan’s on there, and his is “no.” It’s just the word “no.” One of the things he’s been incredibly influential and helpful to me with is saying no to things. It’s a huge, huge problem as you scale as a founder: figuring out how to actually block off time for yourself and say, “No, this is my priority. I’m saying no to everything else,” right?

It’s the same with product. This is also probably one of the main things that I’ve hopefully improved on. I used to, every quarter, just be like, “There’s a P0, and then also there’s a P00, and then there’s this and this and this,” right?

I’ve started to be a lot more disciplined, and I try to be disciplined with my team. Every time we do product planning, something should hurt. It should feel like a breakup. There have to be a couple of really good ideas that you say no to. It’s the same across the entire company. Brian Halligan has been really helpful with teaching me how to do that for myself and how to do it with the rest of the company.

I always go to Jony Ive, who says that prioritization is saying no to even really good ideas.

Yeah, yeah, yeah. No, I think that’s right. It should feel painful. It really should. I didn’t do that in the beginning. I was like, “We’ll just do everything, whatever.”

Having said that, I do think you can do more, and I think you can be very ambitious. But you do have to strike a balance between the two.

You can only take one investor with you to your next company. Which did you take?

I’m definitely not answering that question.

There are several hundred million dollars on the line at this point. I’m not that stupid. How did you ruin the relationship?

I went on Harry’s pod and I really pissed him off.

That’s super funny. Who do you not have on your board who you’d love to have on the board?

I’ve always respected Founders Fund. I’ve always really respected them. I’ve respected the hell out of their companies, too, and a lot of their founders. I just respect them a lot, and we have never worked with them.

In a year’s time, where is Harvey then? You did this great tweet yesterday, and it was like 190 million ARR. I can’t remember the customer base, and I can’t remember the other stats. Such a VC. It’s a revenue number—great, that’s the take. What does that tweet say in 12 months?

I mean, we obviously have revenue targets and things like that. But what I want to switch from is a productivity software that is a nice-to-have to something closer to an operating system that is pretty much crucial to the industry, right?

We built a lot of different features across the board. In Parker Conrad’s voice, we very much built a compound startup. We haven’t tied it all together yet. We’ve done a really good job of creating all the pieces, but we haven’t tied them together.

Maybe an interesting stat on this is our DAU over MAU for people who use 4-plus product lines: it’s 74%. That’s Slack level, right? Slack was like 80 or something like that. It’s incredibly high. The percentage of people who have used 4-plus products is very low, and it’s doubling every quarter.

What I really care about next year is: Can we make this infrastructure? Can we make it so this is a core piece of a lawyer’s workday, and they live in it?

It’s a move from product to platform.

It’s 100% that. I think we’ve done a good job of creating all the features, but now I want to combine all of them together so we can get to that 75% DAU over MAU. That is how you really show that you’ve created something that’s integral to the industry.

Dude, it’s such a pleasure to have you on the show. Thank you so much for doing it in person. It made such a difference, and you’ve been incredibly amenable to my pressing.

[Laughter] Well, thank you so much for having me, man.