Harvey CEO Winston Weinberg: Why You Should Reinvent Yourself Every 4 Months

15:51Brian Halligan:okay let me just ask a couple of very tactical questions that ceos ask me all the time yeah uh you just brought up heads of as a title what the hell is that why do you have them what's wrong with director or vp or manager what the hell is a heads of like a look at a linkedin profile

16:09Winston Weinberg:somebody's a head up like what is that um i like head of actually more than director um I think as simple as possible, director makes it feel like you aren't as responsible for the one thing in the box, basically. And head of, I feel like, I know it's a subtle difference, but it gives you more, this person is the responsible person. That's a good explanation.

16:33Brian Halligan:I get that. It's all ownership. I see.

16:35Winston Weinberg:I think of all titles as just ownership. Because the thing that everyone likes to do is just kind of score them out of ownership, right? And so if you can, and it seems like all of the problems are just, it's unclear who's in charge of this. And even again, like going back to the, I very much don't penalize mistakes. I penalize inaction. If there isn't a head of for a particular thing, then you're in trouble.

17:01Brian Halligan:By the way, I have an analogy for you. The DRI thing hit me square in the head because one of my employees said, you know, it's like a plant. If you're going away for a month and you ask two friends to water your plant, the plant is definitely going to die. It's either going to get no water or it's going to get just constant water. You're going to come back and it's dead. Is that the way you feel about it? Yeah, 100%.

17:25Winston Weinberg:That's how I feel about it. And then it takes a long time. And so I'll give you an example of, I think, the job of a CEO is actually figuring out who is that person. Right. And so we were doing this pilot process. There were a bunch of people. And I started with, okay, should I say, hey, someone needs to be in charge of this? That was option one. That usually doesn't go that well. Instead, it is this person should be in charge of this.

17:54Brian Halligan:Why? Why can't you get feedback on who should be in charge?

17:57Winston Weinberg:So you can do that. But sometimes that takes a really long time. Right. And what I've found is is a lot of times it's the same as a product roadmap, to be honest. Like people, when you say, what is the P0? What does almost everyone do on a product roadmap? OK, so here's a P0, but then also there's a P1 and then there's a P2. And actually, let's have three P0s. And actually recently, last quarter, someone I definitely made fun of them for doing this. They made a P00. zero. Okay. Because they didn't want the PZ. They're like, it's too hard to choose. Right. And the reason people do this and I do this too, is you don't want to be wrong.

18:38Winston Weinberg:And if you say there's three things that are PZero, you can hedge your bets. And if you built the wrong thing and you said, hey, this is a PZero. And then a quarter goes by and no one bought it or no one used it. You can be like, you know, sorry, if you have three PZeros, you can be like, oh, well, we built all three. And like some people kind of like this one and some people kind of like this. And it's very diffuse. If you said at the beginning of the quarter, this is the P0, you built that and no one used it, I mean, you built the wrong thing. And it's the same as the DRI, where I think people get uncomfortable with having the DRI because then there's shared ownership if you don't do it.

19:14Winston Weinberg:And you can say there's three people in charge of it, and then they can all go like this and point at whose fault it is, right? If you just say that person's in charge, they're in charge. And it could, you know, it might not be their fault. But like at the end of the day, like when we put up quarter numbers, when we have product numbers or anything like that, it's my fault. No matter what. Like no matter what, our performance as a company is my fault. No matter what. And if you have a DRI in each spot, there is somebody who is like that and feels not about each thing. Yeah.

19:43Brian Halligan:One of the things I noticed about being a CEO is as the company got bigger, we could get less things done. Yeah. But we get them done very well. Have you noticed that as well? And how many big things are you working on right now?

19:59Winston Weinberg:Too many big things is the answer. Okay. How many you got?

20:03Brian Halligan:We would have four. And I would try to get it down to four.

20:07Winston Weinberg:Like product-wise, we have way too many things. And I keep doing this. I mean, part of it is we're building a platform and I do think you can build a lot faster now and you can build these things in parallel. But we still I am by far the main problem here of every quarter. I end up being like, no, no, no, we can do more. We can do more. We can do more. And then as like company initiatives, we also do too many things. And like we're in 60 countries operating across. We have in-house customers and then we have law firms. They have different needs. And we are honestly still trying to do kind of it all.

20:40Winston Weinberg:and so I do think we are getting better at saying no this is the p0 and that we do really well I don't think it's we're not at the stage where we do four if we pushed it down to four things I think we do incredibly well at that we're still at the stage where I think the p0 will always be done extremely well as long as there's repetition and not changing the p0 every week which I I definitely do sometimes. Okay. For sure. For sure. As long as there's consistency about that P0, I think that we can do a P0 well and then we'll do everything else pretty well. And we'll do them well enough to eventually they'll become a P0 and then you jump onto that.

21:22Winston Weinberg:And I do think you can take more bets right now. Like you can. I do too. You can build really fast.

21:26Brian Halligan:You can get more shit done now.

21:27Winston Weinberg:You can. Yeah. Okay. I have a lot more questions. I have two on the org.

21:32Brian Halligan:There are two of the CEOs I work with that are in the process of layering a very good employee. And there's a lot of stress. That CEO is feeling a lot of stress about that layering, about the signal and sense of the company, about that individual employee losing that employee. You've done a ton of this type of thing. Advice to those CEOs who are in that process? Tell them about it.

22:00Winston Weinberg:And I've done this wrong, too. Like I have, this is, I mean, it's actually weirdly similar to the P zero problem of, I think the reason people do this wrong is because they're scared, right? Where like they're scared of making the wrong decision and they're scared of, I mean, a lot of things, right? Like it takes time to hire somebody really well, like to hire someone who's very good at this job. And do you want to bring them along for that hiring process? Right. And in some instances I have some instances I haven't. Right. and you have to basically say this is how i do i'm doing it going forward and this is my plan is i am going to bring that person along for the hiring process and this maybe goes back to what i said before which is i think there are almost everyone that is doing their part of the company

22:46Brian Halligan:can do a better job than me and if they can't i am hiring someone who can like i should not be the

22:51Winston Weinberg:best person at every single role at the company god no that's terrible you're a terrible leader if that's what you're doing. But I do know how to do all of the roles to at least the company doesn't go to zero state, right? And so number one is make sure you understand every part of your company so that if that person did leave that superstar, you could take their place while you hire the new person. You need to be able to do that. That will reduce your fear. Two, bring that person along. If you really think they're that good, it is worth the chance that they will stay. And the only way they will stay is if they trust and respect you.

23:29Winston Weinberg:And they have to trust that their career growth can be really high, even with a new person on. And so you just have to take that risk. And I've done an okay job of this. There's been instances where I've done a really bad job. And the reason I've done the bad job is because I'm scared that that person is just going to leave and we're going to have a huge gap at the company. but at the same time I don't think that person is the right for three months from now or six months from now we're going too fast and you just you have to feel a confident in your own ability to fill and b you just have to trust them and bring them along for the ride and if you do bring them along and they do want to stay they're going to even work they're going to be better at their job and they're going to learn from that person they're going to act like they're going to treat

24:11Brian Halligan:them like a mentor I got layered twice in my so I'm old I got layered twice in my career

24:20Brian Halligan:once there was a lot of heads up and a lot of feedback that I wasn't quite ready and that might bring someone over me and then they did it and I was involved in the interviewing process and I stayed and I was happy and I learned a lot from the person they brought over me yeah in another instance I kind of got happy talk and I thought I was doing pretty well maybe I didn't think I was killing it but pretty well and out of the blue they said hey we're going to bring somewhat over you i i left in that case in my sense on this stuff is just surprises are never good feedback's underrated um and overall if i look at the history through hubspot ptc on my whole career like when layering happens about 50 of the time that person gets layered a year later

25:07Winston Weinberg:is gone yeah well it could be worse gone is actually potentially better than what could happen, which is they're there, but they're not, they're dragging everything down. Yeah. Right. And, and especially if they were a star, because that like, if they were a star, then that's incredibly important part of your business. And they will really block the person from joining. Right. Like they've massively blocked that person. I don't know. I, I, we've, we're going through more of those transitions right now. And to me, if I could redo some of this stuff, it would be bring them along even more. I see.

25:43Brian Halligan:even more bring them along and just risk it okay uh you hired katie burke hubspons chief people officer yep uh tell me about her why you hired her and then you just promoted her to coo what does the coo do inside a company like yours and companies like yours ben horowitz wrote a really good book called the hard thing about hard things and he was very negative on the idea of a COO. And I read his book about a month before I pitched him at Andreessen Horowitz. And I had just hired a COO, J.D. Sherman, great guy. And I needed a COO. I needed someone to keep my trains on time. And we went into the pitch, my co-founder Dharmesh, myself, and J.D.

26:33Brian Halligan:And we sat in the order of J.D. first, then me, and then Dharmesh. And I had forgotten that Ben didn't like the idea of COOs. And we got to intros, and the first person is just a JD who had just started the COO. And Ben just was like, why? And what are you doing? And was kind of really negative on that idea. It turned out to work for us, and Ben may have changed his mind about this. Actually, he's coming on the pod. I'm going to ask him about this, and he's obviously very wise. What does your COO actually do?

27:08Winston Weinberg:Yeah. Yeah. I mean, so a couple of things here. One, there are one nice thing about GTM is you have objective measures, right? So you can be like, okay, do they hit these quotas, et cetera, and you can kind of test, right? Harder on engineering, like sure, you can do like code shipped, et cetera, but not an insanely good metric, right? one maybe metric for Katie um last year we just did like our year in review or whatever today and I sent I think it was like 85 ,000 slacks or something like sent that that many slacks she was she was I think second and it was like 81 ,000 or something third place was in like the 60s something like that so there is maybe a little bit of an objective measure not that slack sent is like performance, but it does have some indicator of like how involved you are in the company.

27:59Winston Weinberg:Right. And she Katie basically was was the COO probably six months ago, I would say, in all but title. Right. And what that I think it's different for every company. Right. So I am definitely one of the founders who I like being knowing about every single part of the company. So like I like thinking about operating cadences. I like working on product. I also like working on GTM. I like working on partnerships. I like working on hiring. I like working on everything. So there are some COOs where what you do is basically, hey, you go run GTM, you go run every part of the business, and I'm only going to work on product, and that's what I'm doing.

28:36Winston Weinberg:And that is awesome, and it works for a bunch of folks.

28:38Brian Halligan:There's a bunch of companies doing that.

28:40Winston Weinberg:Tons. And at that point, I think the role of the COO is quite literally just like GTM. Like a lot of it is GTM. Like trains on time, sure. But I think a lot of it is they just, they kind of basically run GTM. That's not her. That's not what Katie's doing. What Katie is doing is basically every other part of the business combined. And so her role is like a lot closer to a partner, like throughout the entire process. So, you know, I have like an operating cadence personally. I have a list. It's called like The List. and it basically has all of the things, like all of my docs, all the things I'm tracking, et cetera.

29:19Winston Weinberg:And then it has like a daily. And then I copy, paste, and refresh it every single day.

29:24Brian Halligan:And you go through them. Wait, talk about a little more detail. I want to hear that.

29:27Winston Weinberg:Yeah. So I have a list that is basically like, I have focus or operating cadence of the company, which is like all of our quarterly goals, things like that. And then I have like product roadmaps, PRDs, everything like that. And then I have things that I want to remember. You're actually on there. I have basically a quote from every person. Yours is no. It's just Brian and then dash no is what it says actually. There's some other ones on there, but I'll tell you you're actually on there. And then I have basically like metrics that I'm tracking. So like renewal rates, like product usage, DAU over MAU.

30:02Winston Weinberg:And then I have like star focus, which is basically like one thing I care about a lot right now is improving the UX UI of the company. so I'll put like every single doc that is relevant to that and to tracking that and any of the ideas right and then I have my daily list right and on that daily list every morning like when I wake up I go through that list and there's multiple things on there that I send to Katie and Katie is able to go through and these aren't like small things there's a big things and they're all cross-functional

30:35Brian Halligan:Like what?

30:36Winston Weinberg:Like we need to revamp our pilot process, right? So that's a really good example where revamping pilot process is engineering, product, design, GTM, post sales. I mean, it's literally every marketing. It's every single part of all of it, right? And I will, like, originally it was I would just try to do all of that myself and wrangle all of that, right? Now it's, hey, could you help me with this? come up with a decision and then bubble up three decisions to me. And what ended up happening from that process is like a lot of people were involved. My chief business officer was involved, CTO was involved, had a product, VP of product, all of those people.

31:13Winston Weinberg:Right. And then I still just made a decision at the end of the day. Right. And if you can scale that, like if you can get a COO who can start doing that, you're basically just duplicating all of the cross functional initiatives that you can handle. Like earlier on you said, Hey, how do you pick your priorities? how do you make sure you're doing all these things? This is how you increase leverage. Like this is how you have someone that can help with this. The other thing that she's incredible at because she did come from being a chief people officer is the number one thing at our company is hiring.

31:45Winston Weinberg:And I don't mean hiring new people necessarily. I mean hiring, retention, making sure that there's one person in charge of each role and making sure that the people are really good are not being pushed down by people above them that are not as good, right? The number one most important thing at the company, nothing else is even close, right? She's really good at that. And so she's very, very helpful at thinking about what is the org chart? What should this look like? And who is that person? Who should be in charge of that? Who should be working across from XYZ? And she's very good at also hiring, which is, again, like the number one thing that I'm trying to do.

32:21Brian Halligan:Okay, let me answer just a super tactical question. Do you also have some kind of admin assistant? And what does that admin do?

32:29Winston Weinberg:Yeah. So I have a chief of staff and the biggest difference.

32:33Brian Halligan:So not an assistant, a chief of staff.

32:34Winston Weinberg:Yeah. Chief of staff. And she's also incredible. And the biggest difference is she manages everything that I need to do. Like my entire life is personal, but everything that I need to individually do myself. And Katie manages everything that is cross-functional that I need to do. Right. So fix the pilots. Right. That is not something that my chief of staff would do. That is something that Katie would do. Right. But if it is, hey, I need to figure out how to change my schedule and how to basically monitor all of these different things. I want to get these data feeds from all of these different sources of the company to put into my dashboard.

33:11Winston Weinberg:And I want to track all those things. That is something chief of staff would do.

33:15Brian Halligan:okay what about like admin stuff like somebody who books your travel somebody who does you know does all your shit like all your personal stuff like there's so much yeah i have that as well

33:27Winston Weinberg:i have that as well um i i took way too long to do that i was still i was you did so you have someone that does yeah i have someone now yeah but for a while i was booking my flights until like two and a half years in or something it's like something like that it was so stupid i mean it It was the dumbest thing ever. Like, I remember I spent there was the day that I broke, actually, and I decided I needed to hire someone for this was I spent six hours trying to book a British Airways flight or something like that. And it was literally six hours. And it was just all day. And it was something about, like, my card.

34:04Winston Weinberg:They thought it was fraud because I had never, you know, it was like a six thousand dollar flight or something crazy like that from SF to to UK. and I had never paid for anything like that on my flight or like personally. And JP Morgan was just like complete fraud. It was like six hours. And I thought back to that the day and I went to Gabe and he was just like, what the fuck have you been doing all day? Yeah.

34:27Brian Halligan:What is that? Very interesting. Let's talk a bit about, let's go back in time and your go-to-market. you have some interesting ideas about go to market in some theses on it. Can you talk about like how does a random company that almost no one's heard of a CEO who's doing it for the first time that doesn't have some amazing long history and legal. How do you go about nailing your first five customers?

35:02Winston Weinberg:Yeah. I mean, it is just insane repetition and trying things until they work. The thing that AI allows you to do is personalize everything to an insane degree. And now there's incredible tools like clay and et cetera for like actually doing this at scale, but you could do it by yourself. Right. So the thing that I would use to do for all lawyers is you can if you're a litigator, everything needs to be filed to the federal court. If you're if you're in federal court. Right. And most big law attorneys, you have to file everything, right? So it's online. It's on this document repository called PACER.

35:35Winston Weinberg:And I would basically download the last thing that they submitted to court. And then I would try to come up with prompts that were like, this is bad. And because they're a litigator and I'm basically attacking something that they just wrote, they would instantly read the screen. It was risky because sometimes, like basically the system, you know, Harvey would hallucinate. and then it would just be over. But the times that it got it right, it was over. And if you think about doing a Zoom with a lawyer, it's like, I don't know how you got on the Zoom. I don't really pay attention to this. Half of them were doing this, like literally like this on the Zoom, right?

36:14Winston Weinberg:And then you bring up, hey, I saw that you filed XYZ motion to dismiss. And in this case, do you want to see Harvey analyze it and say why it's a bad argument? And they would jump at that and they would go through everything. You can do it on the transactional side, too. You just do a merger agreement or something like that on Edgar. And so a lot of it was personalized. I think the other thing that we did on GTM is we wanted to do the hardest ones first. Yeah, tell me about that.

36:41Brian Halligan:Yeah, so... Kind of counterintuitive.

36:43Winston Weinberg:The thesis was kind of twofold. One is I'm still crazy bullish on the models improving and just basically all of the underlying systems improving. I know it sounds like, duh, now. In 2022, it was not at all. Right. It really wasn't. And so there are two theses here. One is the lower end work. It's just like, why not use ChatGPT? Right. For like way, way like lower end legal work. It's like I was concerned that the models are just going to get so good that it's like, yeah, I can review your lease. Like that's just going to happen. Right. Right. And so building a bunch of a solution for that, at the end of the day, I don't know how much value you would add.

37:26Winston Weinberg:Right. So that's one. Two is if you can figure out all of the massive use cases that one of these giant firms has, you kind of have like a perfect design partner for the entire legal industry. Right. Like the reason these firms exist is because when you're doing a massive M &A that involves like 60 businesses that operate in 60 countries, the work is insanely complex. You need like an antitrust lawyer in every single jurisdiction. Right. That's why big law firms exist. That's why you have these crazy amount of specialists in every area is because they can basically jump onto these massive, massive transactions or litigations.

38:06Winston Weinberg:And so they're really good design partners.

38:08Brian Halligan:Their requirements are brutal. it's why compliance requirements why not go after a mid-tier firm that doesn't have to go through a long decision cycle the partner can decide herself and there's not all this compliance and deal just happens and then move up that's the conventionalism why you're tortured well i mean so a couple of

38:28Winston Weinberg:things here weirdly revenue growth like revenue growth like how fast can you gain revenue was like not something we were thinking about like another thing to think about here is like i didn't know what ARR was. I didn't even know what that was. I didn't even know of like, oh, company health, like net new ARR, quarter of a quarter growth, things like that. And to me, I was just thinking about how do you build the best product and not just the best product, but how do you actually show that this is going to transform the industry? And the reality is if you can get one of these top firms that have just never, ever talked about adopting technology before or doing anything cutting edge to do it, that would be a wake up call, like a, wow, this is actually going to be a change.

39:10Winston Weinberg:Right. And it's the same on corporates. So now like last quarter, I think it was like 42 % of our revenue actually came from large corporates, not law firms. Right. And of those large corporates, the majority of them are fortune 100, not even fortune 500, fortune 100. Right. And the reason why is because if you can figure out how to sell to a large bank and if you can get past security review on a large bank and do all the implementation on a large bank you can sell everybody else right um and so some of it is just do the hard thing back to the first ones like so many of the ceos

39:44Brian Halligan:i'm working we get their first accounts because they work for that company before their vc knew somebody at that company it doesn't sound like that was the game you play like usually it's you're networked into your first 10 pilots. It sounds like you kind of cold-bulled your way into your early deals.

40:03Winston Weinberg:100 % that. I mean, the firm that I worked at, no shade towards them, but they were definitely like customer, I think like 200 or something like that. So it was definitely later down the line. And I also, I've been practicing law for like eight months. So I didn't have any connections. It really was just, could you get people that would respond to your LinkedIn message? I mean, just LinkedIn, like you message a thousand people. Like you can just keep doing that. Like tens of thousands at this point, right? And I still get a lot of lawyers that will, I mean, now it's like hard to even go through my LinkedIn, but like I still get all the time, like I messaged them in 2022.

40:44Winston Weinberg:They messaged me back and be like, oh, love Harvey, right? Or something like that. Happens all the time. Yeah, it happens all the time. And so a lot of it was just reach out to as many people as you possibly can. if somebody gets on the phone, you know, to get them to stop doing this while they're on the call with you, show them something personal.

41:01Brian Halligan:I think a lot of CEOs miss this. The way I describe HubSpot's go-to-market was I called it the pain factory. And the way it worked was we built a little application called Website Grader, where you put your URL in and it gave you a score of one to 100 on how much mojo you had on the internet how many links you had your seo power your blog your social and um if i wanted to get into xyz company i put xyz.com in there i get the report i would email it right to the ceo and the ceo would be like whoa i got a 64 out of 100 what the hell do i do to get to 100 yeah yeah like talk to this guy so i I immediately got to the pain and I immediately got some credibility through it.

41:53Brian Halligan:And then the sales rep would show up and like explain the report and show a demo. It's like you have your tooth really hurts. Got a lot of pain in there. Would you like me to fix it? Would you like me to like put a filling in there and put the numit? Yeah, that's HubSpot. And so it's sort of the pain factory. And I think what you did is exactly what we did.

42:11Winston Weinberg:It's exactly the same thing. And it's interesting because one thing I think about a lot is like as we're selling to in-house teams versus law firms, I think about and I think about other AI application layer companies and which vertical they're in as like, are you trying to build something that automates the core competency? Right.

42:31Brian Halligan:And that is going to cause friction.

42:33Winston Weinberg:And what's interesting is we had less friction actually in the beginning because we weren't pitching to firms. we were pitching to lawyers, individual lawyers. Yeah. And so their pain was, I don't want to do this particular piece of my job. Right. I don't want to go through tens of thousands of documents and, you know, do this massive like sign off thing, right? Like closing checklists. I don't want to do that, right? That's not a fun part about being a lawyer. Now you have to kind of change your pitch because you're not just pitching to the lawyers, like the users. You're pitching to the law firms too.

43:08Winston Weinberg:too. And law firms have different pain points, especially as AI develops, than just the lawyers themselves do, right? So you have to kind of like change your pitch. And that also impacts kind of what you're building. Whereas on the in-house side, you're still actually just pitching to the lawyers. Like that's it. Like you're just pitching to them, right? And it's because, you know, you get like a big customer like Bridgewater or something like that. Like Bridgewater's core competency. Like they're not trying, like they don't provide legal services, right? That's not like what they are doing. And that helps the business, right?

43:43Winston Weinberg:And because of that, it is seen as less threatening because it is not the core competency of what Bridgewater does, right? And I just find that interesting because you kind of have to balance the pitch of like, this is good for your users and the pain point for your users versus what is actually the broader ecosystem pain point for the law firm or for the corporation or whatever it is. And as AI, I think it's better and better. You got to think about not just the individual user, but what is the pain point of that industry?

44:12Brian Halligan:Yeah. You didn't know anybody in these big law firms. You also had never sold anything or built a go to market engine. And so many of the CEOs I'm working with are the same. And like, by the way, you're quite different than most of the CEOs I work with because most of them are software developers. Yeah. And deeply technical and product people. And then they built something amazing. Like, I have to sell this thing. Just talk a little bit about that. And how did you learn your craft? And how did you? Because my sense is one of your superpowers is you can sell.

44:51Winston Weinberg:So I think there's a couple of ways to do it. One thing I want to say in the beginning too, the times that I'm best at product is when I'm selling the most.

45:00Brian Halligan:Yes.

45:01Winston Weinberg:It's not even close. I've all decided. It's like actually not even close. Yeah. Like the times I did this in, I think it was like Q3 or Q2 of last year, I spent too much time not talking to customers. And like sitting down in San Francisco and being like, this is the roadmap for the next like year. I missed, like I missed so many product things by doing that. Like I made wrong product decisions. There were so many things that were wrong. I do best by far when I'm talking to customers 24-7 and working on product simultaneously. Makes sense. If you do one or the other, it actually like doesn't work at all.

45:38Winston Weinberg:So I wouldn't start by that. But the learning to sell thing, I think the most important thing is you have to adjust to who your buyer is personally. Like it is people reading. And there's like some instances when, you know, you'll get on a call with a big group, right? A big group of folks. And it's very obvious that one of the people on those calls is like trying on purpose to make you sound bad for a particular reason. Like you don't know why, but it's just like very clear. The number one thing to do is to meet with that person one-on-one. And no one wants to do that because everyone's like, ah, that was uncomfortable.

46:20Winston Weinberg:I didn't enjoy that, right? but that's actually the person that there's something else going on whether it's like they tried to build something in-house and it didn't quite work and you're kind of threatening to them or whatever it is and then if you turn them around and they're they become champions it completely changes everything and so it's kind of what you said before where it honestly is like a lot of it is just like find the thing that hurts and like you don't want to end up doing almost entirely that's what you want to do like if you push on the the two greenfield stuff it actually

46:49Brian Halligan:doesn't work okay a lot of my ceo founders some are in really sexy businesses and it's easier to hire developers to build sexy stuff yeah don't take this in any offense but building legal software doesn't feel that sexy how are you able to attract top-tier engineering talent on building

47:09Winston Weinberg:software for lawyers yeah the biggest reason is because we have to work there are a lot of actually frontier things that we need to solve that the big labs will maybe eventually solve, but they aren't working on it right now. I'll give you a really good example of this. So we launched memory this morning, right? And this is going to become super important for us. There's a lot of ways to do memory. But the most important version for us is almost everything that lawyers do is document-based, right? Right now, the way that Chachapiti memory, anthropic memory, et cetera, there is actually no understanding of these are the documents as artifacts and things like that, right?

47:47Winston Weinberg:Super irritating. Super irritating. But that's something that they will solve eventually. Yeah. If we don't solve that, our product goes to zero. Yeah. Right. And so there's actually a tons of frontier type things that I think these

48:02Brian Halligan:application layer comes to do. Okay. So they're hard problems.

48:05Winston Weinberg:Really hard problems. That's how you tell. Everyone is going to have to solve eventually. I see. But we have to solve sooner because of just the nature of our customer base, right? Another example of this is we already have something where you can basically collaborate with AI systems in our platform and outside folks. So not just like multiple people from your own corporation working on something, but I'm a big bank and I want to collaborate with 10 law firms. Also something the big labs have not solved yet, right? And we had to do that first.

48:39Brian Halligan:They haven't. They haven't.

48:40Winston Weinberg:No, it's super irritating. And they will, to be clear. I'm just saying there's so many of these domains where I think it's really exciting to work at the company and building software there because you're working on frontier systems that for sure OpenAI and Anthropic are thinking about. But going back to our P0s, it's like it's way down that way.

48:59Brian Halligan:Yeah, yeah, yeah.

49:00Winston Weinberg:And so you get to work on that and you might be able to solve that better as a company. I mean, you should, otherwise your company's over. Better than they can faster. And that, I think, is really exciting for people.

49:09Brian Halligan:I want to talk about you a little bit something I noticed about you and I spoke to some people who work for you and I would ask when I ask people like tell me about Winston what's his superpower the word intensity is the first word that comes to everyone's mouth and I agree and probably people watching this would agree where does that come from? you're extremely motivated and extremely intense um why do you have a chip on your shoulder yeah i think your childhood

49:46Winston Weinberg:yeah um i think it's a combination of things so i always let my co-founder whenever we do intro like intros i always let my co-founder go first and he has an awesome background amazing yes incredible background and then i go i did nothing for 27 years is like well my well now I'm a little older, but that was basically my background. I think the reality is I definitely had a lot of problems when I was younger, kind of mental health problems and things like that. And I was a terrible student, got kicked out of a bunch of schools and things like that. And I didn't find something that made me want to get up every morning and apply myself.

50:25Winston Weinberg:And when I started this company, I had no idea that this would happen, but I've never felt this in my life. Like I've just never felt, I've never felt this like overwhelming obsession and excitement to get up every morning ever. And it is absolutely terrifying to me to lose that. Like it is terrifying that I will lose that. And I think the problem with it is that's not like, Oh, the company is going to go to zero. It's if we don't keep moving and we don't basically capture the opportunity that we have, I think I'll be stuck in a situation again where I don't feel that. Like I don't feel like massively challenged.

51:05Winston Weinberg:I don't feel like what I'm getting up to do sucks. And like one example of this is I literally try. I try every week to have at least like two to three things that make me super uncomfortable that I'm doing. And I don't think i feel good unless i do those things like if i'm always like that that's pretty intense and not that fun were you always that way or like no i i think maybe i might have been but i didn't have the opportunities to do those things or i maybe let me take more ownership of it i didn't put

51:38Brian Halligan:myself in situations where i would find those what changed inside of you that all of a sudden you were

51:45Winston Weinberg:yeah um i still figuring that out to be 100 honest like the the part that i have figured out is what motivates me. And that took me like, I think I figured that out like last year. Like it's pretty recent. And the thing that is insanely motivating to me is I just want to see how far I can go and like keep going until I'm like people, this is just, I can't do this. Like I break. Like it's just, this is a scale or this is a type of project or something that I am not good enough to do. And that doesn't mean personally, by the way, like this is something that has changed massively for me is I used to think that companies were very much like heroics.

52:24Winston Weinberg:And it was like, just, you know, it's like the founder, can the founder do it? Can the founder do it? Can the founder do it? No, like not being able to do it is you can't hire people that are good enough. Like you can't, or you can't convince people or you can't lead people well enough, right? You, there's so many different ways why you can get stopped, but it's not physically you can, can't do it yourself. But that's what is massively motivating to me is I think we have an insane opportunity and I'm like terrified of missing out on it and I'm terrified of going back to how I

52:55Brian Halligan:felt before this got it do you think there's a downside of your intensity and let me just I'm interviewing HR McMaster who's very non-partisan but he was a non-partisan national security advisor in the first Trump administration he lasted like 14 months and he left slash got fired and he said Trump chewed me up he just chewed me up and got everything out of me and then kind of disposed of me and this is a non-partisan podcast I'm not casting any aspersions on anyone do you are you a little like that I think sometimes um I'm trying to get

53:42Winston Weinberg:better at it. But I think, yeah, I think, I mean, A, I think I do that sometimes. And I think that sometimes people say, hey, that actually like, I didn't think I could do that. And I could, and that made me feel amazing. That is sometimes how it happens. Sometimes I think I take it too far. And I think it becomes a problem. And I think the other thing I need to do is there are some situations and it is very humbling to feel this as a founder but it happens where the chance of success is higher if i say this is the goal and what we should do and then i stop poking and i let them do it i'm serious and it is so hard and it's so humbling but once it happens a couple times it gets easier right um but i i do feel that okay i've known you for a while now i'm really

54:33Brian Halligan:proud of you thank you so far and matured so much and you're doing such an excellent job i'm really happy to know you and happy sequoia investing you i think you're doing great thank you man thank you yeah that means a lot appreciate you coming on the pod giving the pearls of wisdom to all the ceos out there and go get them keep the rocket ship going thank you yeah thank you man thanks okay i hope you like that episode we've done six now. I think that's my favorite. For some reason, it got a little dusty in the room towards the end. You know, that can happen. As you could tell, I know Winston pretty well.

55:11Brian Halligan:And when I look at CEOs these days and evaluate them, I have a rubric that is my lock rubric. The L is for lovable. The O is for obsessed. The C is for chip on the shoulder. And the K is for knowledgeable. I remember first medium and at least to me, he's lovable. Like if I were a younger me graduating from school would want to go to work for him. Really obsessed. You saw that like he's literally a billionaire and he's got roommates. I talked to him over the holidays. He didn't have holidays. He's pretty obsessed with completely obsessed with what he's doing. You felt the chip on the shoulder. Part of it is how he grew up, but part of it also is that he's a non-software developer founder here in Silicon Valley.

56:00Brian Halligan:And he brings that up a lot. He brought it up a little in this pod, but he's got a big chip on the shoulder. And Nikkei is a very knowledgeable guy. He's also very humble. He knows he's made a lot of mistakes. He faces those mistakes and he tries to improve them. That's something I love about great CEOs. is the problem with being a CEO is everyone tells you how great you are all the time. And as it scales more, that happens, particularly if you're going very, very fast. And he's a bit immune to that. And he's very self-critical and adjusts a lot. And I think you saw that in the pod. Anyway, I thought this was pretty good.

56:39Brian Halligan:If you are enjoying the pod, I think this is our sixth episode. Give me a comment. We need some feedback on how we're doing, good, bad, or indifferent. Love to hear from you. See you on the next one.