Winston Weinberg on Harvey, Legal AI, and Building a Category-Defining Company

Winston Weinberg

I can break down the whole document. At the top it has the couple of things I want to remember — kind of motivational things. The one I care about most is prioritisation. This is something I think people have a really hard time with: every three to six months you have to completely redo how you do prioritisation as a leader, and if you don't, you're really going to start messing things up.

Then it has the top three documents that I care about tracking. If I'm concerned about a certain part of the org, it'll have, say, a revenue tracker, or if I'm worried about post-sales and customer service, a document with a bunch of stats on that. Under that it has: what are the three goals for the quarter? Almost always that's one product feature — we're getting to the point of shipping four new products every quarter, which is awesome — and one major area of the company I need to fix.

After that it has my daily list. The company dashboard and motivation stuff, everyone has a version of that. The thing that's actually good is that every day I rank everything I need to do. It's daily; I refresh it, and I cross things out. The re-ranking is really important, because what I've found is that the more times I click into that doc — it's called 'the list' — and re-rank something, the more I think about what I'm doing. Meta-thought about my thoughts. That's when I'm prioritising the best, by far. That's when my schedule looks best and I'm performing best — it comes down to how many times I click into that doc during the day, because it makes me re-org something, put something in first place in bold, and ignore everything else.

Winston Weinberg

Most things. And an increasing amount of things as the company goes on. I used to say no to almost nothing.

Winston Weinberg

When I get really bad at it, I ask my chief of staff to force me to write a paragraph about why I'm going to take a meeting. A full paragraph about why I should take it. It's so easy if you do it that way, because for 99% of meetings or events you start writing the first sentence and you think, I don't want to do this. And if you don't want to do it and it feels like a waste of time, the meeting probably is a waste of time. For the things that are really important, when I have to write that paragraph, I could write 20 pages.

This goes back to: how much of your week and your day are you actually thinking about what you're doing? What is the goal of the company right now? What is the main bottleneck? The best founders I've seen are really good at two things. One, they built a machine. Because they've built a machine, they have time to focus only on the main bottleneck within it. Those are two different skill sets and you need both. If all you're doing is bottlenecks before you've built the machine, you're never going to hire the right staff or build the right product. So you're constantly building out the machine, and once it's somewhat built, the number one goal is improving it constantly.

That's hard, because it means you're in pain 24/7. If something's going well at the company, you're not working on it. If a part of the company is running well with no bottlenecks, I ignore it entirely — absolutely entirely — and I try to focus only on the things that are burning, and on the number one thing that's burning.

Winston Weinberg

The reason people have a hard time saying no is they say yes to a lot of things that make them look good in the short term, instead of taking the pain of ignoring something and then doing so well because they ignored it that people back off.

Let me give an example. An investor says it's really important for you to hire a certain person right now. What you might end up doing is take a bunch of meetings with that C-suite candidate, because the investor says you're having revenue problems and the reason must be that you don't have that executive. But deep down you know the reason you have a revenue problem is a problem with product. It has nothing to do with not having hired a chief revenue officer. The problem is the product isn't good enough — but fixing that has a delay. So people start making improvements the third party can see immediately, because every time you do that meeting you get a pat on the back from your VC: 'Good job, you're progressing.'

The alternative is you ignore everyone, everyone thinks it's getting worse and worse, and you go fix the issue that's actually the issue. Then in two quarters or six months, suddenly the company's doing really well. That's just so hard to do. You face so much pressure as a founder that it's really hard until you've proven yourself. A lot of the best founders I look up to have had tons of moments where the entire outside world says 'go do this thing, you need to improve something,' and they put blinders on, completely ignore everyone, and go do the hard thing they know will actually fix the problem long-term. Six months later, a year later — hell, sometimes ten years later — they're right. You get instant gratification from making progress the way people think progress is made. You don't get instant gratification from saying 'I think you're wrong and I know the business better than you do' — but that takes six months to prove. That takes a lot of conviction and discipline.

Winston Weinberg

Number one: determine immediately if something's a one-way or two-way door, with the baseline that 99.9% of things are a two-way door. The second thing is, what is your number one priority right now — your P0? Based on that, does this help the P0, hurt the P0, or is it irrelevant to the P0? That's important because if it's irrelevant, it doesn't matter much what you decide, so just do something and go. If it's negative to the P0 — it takes attention away from it — the decision is no, full stop. And three: be realistic about who is actually going to be doing it.

Winston Weinberg

We're building a system for lawyers to use all of these models to do their work in a much better, more streamlined way. That's an incredibly broad explanation. Another way to think about it: we're tracking the progress of all these models and applying it to an industry. In a way you're building a legal brain — the same thing other folks are doing in other verticals, like a medical brain in the medical vertical.

There's a lot to break down. Where is a model going to do a lot of the work? Where is a human going to be reviewing it? How do you change the processes and structures of legal departments and law firms, and how services are delivered? It's less 'we produce a product' and more: these products are transitioning to redefine how the profession actually operates.

Winston Weinberg

I got very lucky and met my co-founder, Gabe, who had a background in AI research — he was in the first Google Brain class, actually, and then worked at Meta. We became really good friends and lived together for a while. At the time he was trying to push LLMs at Meta pretty hard, and at some point I said, what is an LLM, can you show me one of these things? What was available then was public API access to GPT-3. This is early 2022. Everyone had access; I was very confused why more people in other industries weren't using it.

I started messing around with it. The first thing I actually did was use it to help run a Dungeons & Dragons game — it's actually really good at that. Then I was on a pro bono case for landlord-tenant law, which I don't know anything about. I started using it very basically: here's a fact pattern, here's a statute in California, apply the statute to the fact pattern. It got really good outputs. To test it more, we went on r/legaladvice, a subreddit where people ask legal questions, and grabbed a bunch of California landlord-tenant questions and ran a chain-of-thought prompt over them. We gave the outputs to three landlord-tenant lawyers and said, 'Somebody asked this question, here's the answer from a lawyer — would you send this with zero edits?' We said nothing about AI. On 86 out of 100 questions, three out of three attorneys said yes. That was the 'oh my god' moment for me and my co-founder. We said, we need to do something in this industry.

Winston Weinberg

Simultaneously, Gabe had some friends thinking about joining this company called OpenAI. We said, we're using GPT-3 to do this — let's just cold email Sam Altman and the general counsel at the time, Jason Quan, who I think is chief strategy officer now. The body of the email was basically, 'Did you know the models were this good at legal?' They got back to us pretty fast. We met Jason first, went through what we'd done with Reddit, showed them our chain-of-thought prompts. Then we met the rest of the leadership team — on the 4th of July, actually — pitched them our idea for the company, and raised money after that.

Winston Weinberg

Yeah, we didn't go to any other VCs. I don't have a tech background and I'm not from the tech industry, so this really was: hey, we experimented with this, we think it's an incredible direction, if these models get even slightly better this is going to change the entire industry. Did you know how good they are right now, and do you know anyone doing this?

Winston Weinberg

The hardest thing in the beginning was getting lawyers' attention. I was a litigator, and there's a nice advantage: a lot of what you file in federal court has to be published online. So I could find the last argument a lawyer made, find the document, grab it, and in the demo say, 'What's good about this argument? Could you argue against it? How would you poke holes in it?'

Early on I'd have demos where lawyers would literally be on their phone — at the time I thought it was AGI itself, and they'd just look at their phone and not pay any attention. When I started saying, 'You filed a brief last week in Apple v whatever, want to see how Harvey would analyse it and argue against you?' — they were completely locked in. It's like that meme where the guy's on his video games and then suddenly he's paying attention. They'd watch the screen and read every single word Harvey produced. Super risky, because a decent amount of the time it would hallucinate and get something wrong, and if it hallucinated the lawyer would say, 'This is useless, get me off this demo.' But when it worked, it worked super well.

The riskiest version was our Series A pitch to Sequoia, where they grabbed a bunch of lawyers they knew and had us demo to them. I remember Peg Grady emailed me afterwards asking, is that what you normally do, because it got them really riled up. We picked a use case, found an argument they'd done, showed the analysis of that brief, and it was a good analysis. A lot of what we had to do early was just get lawyers to pay attention, because they're super busy. The personalisation of every demo matters so much — you don't get it until you feel it on something you actually worked on.

Winston Weinberg

And they're still not using it because of that. There are folks who tried this three years ago, had one hallucination, and said, 'We're not doing that.' We had it with Harvey too — people saying, 'We tried your product three years ago, didn't think it was good enough, unsure if it's improved.' Then they log in and say, 'I don't even remember trying this. This is so different.' People aren't used to that rate of technological change, especially folks not in the tech industry. Right now every release is a massive step change, and it's hard for people to wrap their mental models around that — to think, how do I become anti-fragile, okay with making different choices, and really think about the future when everything is changing so quickly?

Winston Weinberg

Yes. On hiring senior executives I've been very up and down. I was told to hire senior executives very early on, and I refused — and then I refused too long, about six months too long. But if I'd taken the advice when it was given, I think it would have been a huge mistake.

Winston Weinberg

I saw the impact when I hired them. The main advantage of being a founder is that if you're always on — which I tried to be — you have the context from day one. Your brain only has to do the delta between day one and day two. That's why founders are so valuable for understanding the business and looking both forward and back: the cognitive load of absorbing everything day over day is manageable, so you understand everything going on. Whereas a newcomer starts from zero and has ten years of context to somehow absorb. So you have a very good pulse on the company, and you can tell — if I'd made this change six months ago, this would have moved forward and this problem wouldn't exist. You just have a sense for it.

Winston Weinberg

One was super early on. We thought there'd be a way to one-shot ourselves into building the company instead of doing it the hard way. This was early 2024, about a year and a half in. The idea was we'd buy a company that ended up being ten times bigger than us in headcount, for about the same, slightly higher, valuation than we were valued at. We signed the deal before we had the money — like old private equity funds, the way KKR used to sign a leveraged buyout and then go raise the money. We got the term sheet, locked them up for a certain time, and went to get the money.

We were trying to raise around 700 million, and we got about 500 in clean equity. Then the deadline was there. We had an option to take a loan with PIK — payment in kind. The problem is if you take that debt and don't fulfil the obligation, someone else can own the company — not in dollars, in percentage points. We decided not to do it. When I pulled it off and told the other side we weren't going to do it, I thought the company was over. I thought, I don't think we can build fast enough, the model providers are just going to eat us, without this other company we're screwed. And it forced us to actually go build the company — hire the right people, put the right work into product, do the correct scaling processes, all of it.

Winston Weinberg

It's about 24 hours. Really fast. And by the way, I've had a lot of periods like this — other times we've failed massively and I had 24 hours of 'it's all over,' and then you wake up the next morning and think, we can do this again. That happens once a week, probably. You get used to it. I've had a lot of times in my life when I thought everything was over — when I basically failed out of the first high school I went to, when I took the LSAT the first time and didn't get what I wanted. My point is you have to get used to it: it's over, it's over, it's over, and then everything's fine. You build resilience for losing, for suffering.

One thing gives me more confidence in the company today than ever — which is weird, because externally we face way more threats than last year, ten times the threats, not even close. The reason I'm more confident is I now have a team of people I've failed with so many times. We've taken crazy risk, butchered product lines and recovered them, made the wrong hires, tried to buy a company early on that would have collapsed us. Because of that I feel very confident in my team's resilience and their ability to adapt and get through the next problem. I don't wish it on the company, but in a sense I kind of do — if we get all of those done now, we'll get better way faster.

Winston Weinberg

You want to maximise it before it does too much damage to you. If there are ten things you're really stressed about, do those early in the company. Every time you do one, it should reduce your stress, even if you do a bad job. It's the same for any decision. Firing people is stressful early on, but the impact of firing someone when you're a ten-person company probably won't destroy your company. Avoiding firing an executive when you're a massive company is a huge problem — it could implode the company. So you keep stress-maxing, because you'll reduce your stress for that thing long-term.

Winston Weinberg

Massively. It's less the stress and more going through stress, which reduces it for the next thing. One thing I do a lot — maybe good, maybe bad — is I make decisions really fast. Two reasons. One, I really care about knowing what's going on in the company the entire time, partly because I've never really taken time off, so all I have to do is update my context window from one day to the next. And I've done every part of the company — played every single role at some point, then hired somebody to take it — so I have a good pulse and a lot of confidence about what's going on.

The second reason is that everything I regret at the company is not making a decision fast enough. It's never that I made the wrong decision. What I regret is sitting at the bottom of the stairs too long, instead of jumping up a stair and figuring it out, then jumping up another. The problem is that can be really thrashy. So a lot of what I'm trying to do is set out the principles for how I make decisions, so as a team we can align on them and all make faster decisions. That's the next scaling challenge. Right now the operating system is basically: what is my anxiety, and I push on parts of the company based on that anxiety. The way I want to transform it is: here are the general concerns, and as a company, based on these principles, this is how we approach them.

Winston Weinberg

You have to be to some degree, but you don't want to over-rotate. One thing I did wrong last year was overreacting to multiple threats. As a CEO, the amount of pressure you can exert increases massively. When you're a 50-person company and the CEO's stressed, everyone knows each other and can absorb it and move on. When you're an 800-person company and the CEO gets too stressed, the whole company moves based on that stress. That's how you create thrash — you get overly stressed about everything, and it's the boy who cried wolf: people don't know what actually matters. So a lot of what you have to do as a founder is manage your own stress and then diffuse it throughout the company in a healthy way.

Winston Weinberg

It's a work in progress. Getting enough sleep and working out are the main things — it's not even close. If you wake up right and go on a run, everything else through the day feels calmer; you get a shock in the morning and stay calm for everything else. The other thing is prioritisation. A lot of the reason people get stressed is they're doing too many things and everything feels like chaos. If you prioritise correctly you can have a very good handle on all the company's problems, because you take the stuff that isn't a huge problem and put it somewhere else. All you're paying attention to are the actual problems. Over time you're way less stressed — you might be stressed about one thing, but it's not as thrashy. You don't feel a thousand things going wrong; you feel there's one thing that's terminal, and you focus on incrementally improving that.

Winston Weinberg

The best way is hiring — there's no other way to do it. Hiring and culture. You hire a very good team that feels the same way you do, and your job is to instil a sense of urgency into that team; then those leaders instil it into their teams, and so on. It's about creating a culture and a hiring process that hires and promotes people who have a sense of urgency and can instil it into others, because that scales. If it's just you poking, you cause so much thrash the company won't move in a good direction.

Winston Weinberg

When I'm hiring executives, the thing I look for most is that they believe the same thing I believe: the next year or two are basically going to define the companies that are successful for the next decade, probably more. You have to think about all your decisions that way. One of the hard things with hiring is that people think too many things are one-way doors — way too many. They just aren't. This goes back to making mistakes: you have to make tons of mistakes with things you think are one-way doors to realise not everything is a one-way door.

I moved multiple high schools — technically I got kicked out of one — and it was not the end of the world. Each time I thought, probably we're done. I got really bad grades in high school and my life wasn't over. There are so many folks with prestigious backgrounds who've never gotten a B in their lives, so they think everything is the end of the world. You can't hire people like that, because they will break. These companies move too fast; the world is too tumultuous. You're going to lose a bunch and win a bunch, and you have to have a tolerance for it or you'll break.

No one at the company has ever been let go because they made too many mistakes — never happened, I've personally never done it. They always broke. What broke was they got decision paralysis, they couldn't scale, they didn't hire a good team, they were afraid to hire people better than them. So what I'm looking for is: what's your rate of learning? Are you going to be okay making mistakes? Can you have failures and learn from them? What's your resilience — and your company's resilience? That's something a lot of companies are going to face pretty soon.

Winston Weinberg

It's less scary. And there's another problem. To use your analogy, people plan out exactly which stairs they'll walk on all the way to the top before they start walking — which is bad in itself. What's even worse is that they start walking, and each step lets you see more — more of your surroundings, more of the path ahead — and they're stubborn and say, 'No, I won't change.' They're three steps in and can see they only need one more, but they keep doing it the way they said because they don't want to be wrong, don't want to adapt, don't want to have failed.

People are so afraid of failure, and they think of the wrong thing as failing. Building a company is a thousand failures and then a couple of successes. You have to fail constantly to succeed at bigger things — you make a million bets and one pays off. People are unwilling to do that because they think each bet is a failure and then you're done. Elon has tweeted about this: the first 50 times you fail it really sucks, and then you just don't care. You want to build that tolerance really fast, because if you don't build it for the small things — the baby steps — you won't have it for the big things.

Winston Weinberg

I try to spend a lot of time on 'tell me about your life' — what do you want to do, what do you like doing, tell me about mistakes you've made. What I like to do a lot is go through a Google Doc and do a live editing process — a doc with a bunch of questions or a project, done live and async. Part of that is I really like to work async, so I need to work with someone async, and it's a good litmus test. The other thing it does is you can tell when people take too long — they'll write a 20-paragraph response to what was basically an option A or option B question. If they're massively hedging like that, what are they going to be like in high-stakes decisions?

Winston Weinberg

That's what I'm seeing across our company. The people I already thought were 10x are now 100x. You're seeing the power law of ability increase by a lot, for a couple of reasons. One is getting rid of communication gaps. Sometimes it was hard to tell if someone was good, because they had a lot of good ideas but couldn't communicate them. I know so many people who are geniuses but have a hard time communicating, and the coding models are incredible at closing that gap.

A simple example: something I do a lot now is take something really complex in legal — multi-jurisdictional fund formation, tax exemptions, all these things — and ask, can you give me an example in engineering that's similar? The models are so good they'll produce a one-pager that's a perfect comparison. It sounds silly, but there are so many ways to do translation now, and because there are, you can really see who's coming up with good ideas. The second reason is you just don't need to communicate as much. On a Sunday a really good engineer can go build something and shoot it into the general Slack, and people can see what it is — you don't even need those communication barriers. Some of the best-producing people on Earth are terrible at communicating and working with others, and a lot of what you have to do as a company is create a situation for those folks to succeed. The coding models will let them do better than ever before.

Winston Weinberg

It's the same thing that happens in sports. Being a little bit faster compounds. If you're slightly faster than your opponent in basketball, you'll get the ball in front of them every time, get your hand up slightly higher to get the shot off, put your hand in front of theirs before they pass and block it. You take those small competitive advantages and suddenly you're winning most of the time. That's what's going to happen in knowledge work: if an attorney is slightly better or faster, they're going to get all the work. It already happens — at law firms you have rainmaker partners. How much better are they at every task than everyone else? Probably not that much. But they're slightly better at a couple of things, those compound, and the vast majority of the work goes to them.

Winston Weinberg

This is a really good point. Right now law firms are basically lockstep. If you're better than everyone else in your class, you get promoted at the same rate until year eight or nine, when they decide whether you'll be partner. Law firms are going to have to change this and say, this associate is better at XYZ, we're going to promote them faster, because time-to-partner is going to matter. There are a lot of industries that are locked up, where you get rewarded by how senior you are, not how good you are. I'm not saying seniority and wisdom aren't important — they can make you better — but in some instances they don't.

That's something we've tried to balance at Harvey. We hire a lot of execs who've been there and done that, but we also promote a lot internally, because sometimes folks are better than more senior executives I could have hired, just because they have higher raw talent. It's better to invest in the junior, because the slope keeps going, and in two or three years they'll be way higher than the senior exec you were thinking about hiring.

Winston Weinberg

The weird thing is I'd tell them the same as always. The first year of law school is perfect — really good. You take contracts, con law, all these things, and most of the cases and law you read aren't good law anymore; it's from 50 years ago. But why it's helpful is it teaches you how to critically think, how to make arguments, how to do research. That's super relevant and it's not going away. You're building the critical skills that make you a good lawyer, rather than learning about the actual law. The second and third years need to be massively changed — you take specialty courses, and I don't think that's as relevant anymore. You need hands-on experience starting then.

So what I'd tell law students is pretty much the same: if you understand your clients really well and understand an industry really well, you're going to do great — AI isn't going to massively impact you. If you think your competitive advantage is being the best at writing briefs or the fastest at research, that was never your competitive advantage — I don't think it ever was. The top lawyers who succeed are the ones who've mastered what you master in the first year, plus understand a business and their clients really well. That's only going to have a premium. This will happen across every single industry: whatever the top skills are just get compounded, and the other skills really don't matter.

Winston Weinberg

Massively. Your ability to read a room, to understand — it depends on the practice area. If you're a trial attorney, my sense from the best ones is that a lot of what they're very good at is coming up with a story that makes sense to a jury. I don't see how these models make that not relevant — you have to understand each jury member. There's tons of AI you can use to get more data and A/B test, but at the end of the day it's a very human ability to sit in a courtroom and understand: this is the way I should argue this case.

Same with M&A. The best deal attorneys I've met aren't the best at drafting SPAs or going through diligence rooms. What they're best at is: one person's trying to buy a company and the other's selling it, they're arguing about something, and the attorney figures out how to mediate that. Or there are ten things being asked for, but to be honest they only want number two, and the others are smoke screens. That's the skill set that differentiates lawyers today, and I don't see it being different tomorrow — it's just going to compound the advantage. The value is going to accrue to those decision points, instead of all the work being done to make the decision.

Winston Weinberg

Yeah, exactly.

Winston Weinberg

A good way to think about it: in professional services there are two types of work. One is 'I have work done' — I deliver a work product — and that's going to get fully commoditised. If I need a thousand contracts reviewed and then make a decision, the reviewing of those contracts is going to get automated, for sure. The decision at the top is not. So on one side you have the work product, and on the other the decision or advice. The decision or advice isn't going anywhere. In fact, my guess is it's going to be more valuable over time.

Winston Weinberg

Because you only really get that from a lot of experience, and experience is usually very difficult to distil into the models. When you're doing a large M&A, what the very top attorneys are good at is that they personally know all the other players. They end up becoming deal advisors: I know this is actually what they want, this is what they'll push back against. I think it's going to be very difficult for the models to get that data over time.

Winston Weinberg

My guess is we get to a stage where agents run a very large portion of this, and humans get really good at reviewing the outputs of agents and understanding where they might have made a mistake. That's also what senior lawyers are already really good at.

Winston Weinberg

I don't know that law firms necessarily get smaller. Because AI lets you institutionalise your knowledge faster and work across a lot of different projects faster, you might actually be able to scale faster as a law firm than in the past — you'll need fewer people per project, but you might have way more projects.

A simple example: we're going to have a bunch of regulations about AI use, for sure — there's no universe where we don't end up there, the same way we have audit restrictions on banks. Who's going to monitor that? Lawyers. The legal department. So there's an area of massive expansion of legal work. Think about what a data room is going to have in ten years if you've been using AI to create all the contracts. It's going to be 20 times larger, 50 times larger. It might get to a point where agents are creating all the contracts and negotiating with each other, and a human can't absorb all this data — it has to be an agent plus a human, otherwise you couldn't do the complexity of these transactions.

Winston Weinberg

Exactly. And my point is the expectations are going to change. The largest effect email had on the legal industry was that people expected you to respond with work product faster. That's it. It's going to be the same here. It's a supply-and-demand market with a lot of competition. If one firm says 'I can get this deal closed in 48 hours' and another says 'it'll take me three weeks,' and I'm a CEO who wants a deal done, I want the one done in 48 hours — so it doesn't leak to the press, so someone doesn't get cold feet, so my stock price doesn't drop. There's huge value and competitive pressure in being able to do these things faster and at higher quality.

Winston Weinberg

Sure. One way to think about professional services is that they're cyclical and counter-cyclical, but mostly cyclical. A lot of the revenue from top law firms comes from M&A and transactional work, which is mostly cyclical — the economy booms and you have more M&A. Folks think about legal in a vacuum and say these LLMs will get so good they can do all legal work. What they're missing is it can do legal work today — the question is what does legal work look like in ten years? What does the product review for a lawyer look like when Meta can ship 50 times as many products daily? That's going to change a lot of this world.

Winston Weinberg

You can't do that in the US right now — you need a lawyer. There are basically two rules. One is state by state: the unauthorised practice of law, which is actually a felony. You need to be barred to give legal advice. The other is an ethical rule from the ABA, that non-lawyers can't invest in a law firm. The combination makes what you said impossible, other than in Arizona and Utah, where they've changed the rules to create a regulatory sandbox to experiment.

Winston Weinberg

It completely depends on the client right now — jurisdiction by jurisdiction and state by state, but mostly the consensus is driven client by client. That's changed a lot; over the past three and a half years it's changed every six months, maybe every three. Generally the transition has been: 2023 was 'don't use it at all, or tell me exactly what you're using it for.' 2024 was 'you can use it on certain types of matters' — I'm okay with IP work but not something else. And 2025 started being 'you need to use it, and you need to tell me how you're using it and how you're saving me money.'

Winston Weinberg

Two reasons. One, the tools at this point do task automation, not entire workflow automation, so it's hard to say exactly where the savings are. The tools can't automate entire diligence yet — they can automate bits and pieces — so it's hard for law firms to work out exactly how much time they've saved and the ROI. That's going to change really fast, and we're starting to see it change now. The other thing is the in-house teams. As they adopt it more, they understand what the law firm could be using. For a while in-house teams weren't really adopting this — they were about a year behind — so they didn't have insight into how much of the work could be done by AI. There needs to be a lot more communication between the two sides. A lot of what we're doing is building something collaborative: an in-house team works with a law firm plus AI, the law firm uses AI to the best of its capabilities with their expert data on top, and they pass work back and forth.

Winston Weinberg

Number one: once you get to a certain level of distribution — meaning some customers know who you are — founders should spend almost all of their time on product. The biggest mistakes I've ever made as an exec are when I step away from product and try to make up for it by doing sales. Terrible idea. It helps you for a couple of quarters and feels great, but product is the only thing that scales. It's the only thing.

Number two: do you have the right people in the right positions? You can never spend enough time on that. It's not just hiring and firing — it's whether this person is the right fit for this role, whether you're mentoring them well, whether they're mentoring their team well, whether there are clear swim lanes.

Number three is the hardest: vision-setting needs massive flexibility. Of the three, this is the one I've done the worst job of. In Q3 of last year I wrote a long doc laying out the vision for the product for five years, and it was interpreted as 'we should go build that right now.' That was a huge mistake — we missed some product timings and launches because I didn't communicate it well. So what level of vision-setting are you doing? When do I do the super high-level vision, and when do I do 'no, no — what do we need to do today, tomorrow?' I still struggle with that massively.

Winston Weinberg

I'm really proud of my team — insanely proud. It's hard, because I have very high standards and I'm harsh, and if they listen to this it's probably the first time I'm saying I'm proud of them. We've built a very resilient group of folks who really care about the company. It feels like if we can survive the next few years of chaos, we're really set up for the long term. I'm proud of that, because I'd rather that than be a flash-in-the-pan company that did a lot of things good for short-term growth but didn't set itself up for the long term.

Because of the choices my co-founder and I have made — who we've hired, how we've structured the team, what we've built, our brand, which customers we work with, how we treat them — we're really trying to think about the long term. We've sacrificed some ground to competitors in the short term, by the way. We invested a tremendous amount in what happens post-sales, because we really wanted to land customers and then keep them. I'd rather we don't have a ceiling as a company than feel we're going to maximise the next three years and then be screwed.

Winston Weinberg

There are a lot of ways I'd define success for the company — and at this point you kind of merge with your company when you work on it this much. I want to feel like we left everything on the table over the next couple of years. I shout out to Harley for this because I definitely stole it from him: I really feel you have to re-earn your position every six months. To me, every six months that bar gets so much higher — right now it doubles or triples in height. I want to get to the point where I feel we did everything we could every six months to get over that bar. That would make me feel incredibly proud of whatever we built, and proud of the team.

Winston Weinberg

Yeah. For me, I didn't really find my way for 27 years before doing this company. I had some periods of dealing with pretty bad mental health problems. And this is the most fun I've ever had — it's not even close. It's also very painful, but it's by far the most I've ever enjoyed life. It genuinely isn't close. There was a life before this and a life after, and I never want to go back to the life before. I'm extremely grateful for the position I'm in, and I don't want to lose it — and I don't want to feel like I didn't put everything I possibly could into it when I had the opportunity.