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

Intro

Winston Weinberg: I think people feel like you can’t make mistakes. And that is actually the opposite of how I feel. I would much rather people just try and make a decision and then it’s wrong, and a week later they adjust and change, than they spend, like, three months not making a decision. And by the time that that decision was made, the entire market has changed, our internal org has changed. It doesn’t make sense. And so right now, I think my number one hiring criteria is literally just bias for action. Like, that’s it.

Brian Halligan: Hey everybody. This is an episode with Winston Weinberg, the co-founder and CEO of Harvey. It’s a particularly good time to interview Winston. The company’s at $190-million run rate, and that’s 4x from last year. They’re at about 500 employees, that’s about 2x from last year. So the company is absolutely ripping. He’s at the head of a real rocketship. And what I was interested in interviewing him for is I just wanted to see what it was like when you’re in a company growing that fast and scaling that fast. Like, what’s working, what’s not, how does it scale? We got into some good stuff and he’s got some real counterintuitive takes on scaling, on hiring, on building organizations, on go-to market. He is a very thoughtful fellow, and I think you’re going to enjoy the episode. At the end, I’ll come back and I’ll give you some of my personal takes on it. Hope you like it.

Main conversation

Brian Halligan: How does it feel to be the world’s newest—at least on paper—billionaire?

Winston Weinberg: Is it—is it newest? I’m actually not even sure if that’s true.

Brian Halligan: Who became a billionaire after you?

Winston Weinberg: I’m sure, like, five to six people from application layer companies. Not sure. No, I mean, I know we had a thing in the New York Times and there’s something in the New York Post about this recently. I mean, like, Gabe and I still live in the same apartment. Like, our lives, like, haven’t changed much at all. And I think, like, some of those outlets kind of tried to make it be like, “Oh my God, like, even billionaires can’t afford, like, housing in San Francisco,” et cetera, or something like that. And, you know, I mean, I think, like, there is definitely a housing crisis in San Francisco. I don’t think, like, my co-founder and I are exactly like the people that are massively struggling with it. But I will say, like, we have lived in the same apartment for, like, three years. I think it’s more just like, why move? Like, we like the apartment, we like living together. Like, I don’t know.

Brian Halligan: I think what’s interesting to other CEOs who are listening is—I mean, you’re the head of a rocketship, and it’s an interesting time in the history of the company to interview you. What’s it like? What has surprised you? Like, what is being a CEO in a company like this that people would be surprised about?

Winston Weinberg: Yeah. I mean, definitely is how chaotic it is internally, that’s for sure. I think there’s two things I probably hear the most is one, I think that we hopefully have done a lot of the very, like, hard things right. And then a lot of the machine building, it’s still not there. Like, the machinery is still not there, right? So, like, the direction, I think, of travel has been really good. We’ve made some good product decisions, et cetera. But, like, a lot of the just, like, normal business machinery is not in place on the product side and also on GTM.

And so what I find is maybe two things when people join is one, they go, “Oh, I thought this would be here. Like, you guys are at such a large scale, you know?”

Brian Halligan: By the way, that never goes away.

Winston Weinberg: Yeah, that probably never goes away, right? Like, “Oh, shit. I thought this would be here.” That happens a lot. And then I’d say the other thing too is, like, I hold ourselves—and Gabe does, too, and the rest of the leadership team does—to extremely high expectations. Like, the reality is I think we’re executing well. But also, this is just like a once in a lifetime time period for everyone. And so I think that definitely something that happens internally is you will get folks that from the outside, they’ll say, “Oh my God, like, Harvey’s doing so well,” all these things. And then internally there’ll be more, “Oh no, we’re, like, not going fast enough or we’re not doing—” right? There isn’t tons of everyone sits around every Friday and claps, et cetera.

And even at the end of the year, right? Like, my memo to start the year was, “Hey, we did a good job last year, but these are all the things that we really now need to catch up to.” And I really believe that. Like, it feels like every six months you have to, like, re-earn your position in the market. And that trickles down through the whole company where you have to re-earn your position at the company—including myself. Like, and every six months you absolutely have to change. And if you don’t, I think you just break.

Brian Halligan: Okay, I got a bunch of questions on that. When I was CEO, I was always criticized that I was very good at finding the problems, very good at the worries and, like, obsessing over what was going wrong, and was not very good at celebrating the successes. I got that at every one of my reviews every year and I tried to get better. I just wasn’t good at it. Are you the same?

Winston Weinberg: Yes. And I think, like, part of it is good, I think, and part of it is bad. And I’ll give maybe a couple examples of it being good and bad. I think on the good side, if something’s going super well, I just don’t think about it, right? And I’m going to go spend time on something else.

Brian Halligan: Yeah.

Winston Weinberg: The bad side is sometimes that thing that’s going super well would be doing 10 times better if you spent more time on it, right? And so there have been instances in the past where someone at the company is doing incredibly well running an org, right? And I spend a lot of time with them, but I don’t spend tons of time, like, hands on running that part of the org, right? And then I realize after, like, a month or so, wait, this org could just be 10 times higher if we were spending more resources on it, if we promoted this person, if we gave them more under them, et cetera, right?

And so I think the positive of it is it really is you should spend the most amount of your time unplugging or fixing the biggest problem at the company, right? And as we scale, a lot of what I’m doing is just figuring out how do I get bandwidth to actually do more and more of those, right?

The bad side of that is sometimes there is something that it could be accelerating way more, and you’re overlooking it because it’s going really well, right? That, I think, is the thing I’ve gotten wrong is when I’m only paying attention to the negative. So it’s not about celebration. It’s more like, wait, this is working, or this person is incredible at their job, they should go and try something even harder.

Brian Halligan: I’ve been on the journey with you for the last 18 months or so. A lot has changed. In very fast scaling like you’re doing, what has broken? Like, what breaks along the way?

Winston Weinberg: Everything?

Brian Halligan: [laughs] At HubSpot it felt like everything broke. Like, what are the things that founders can learn from your journey over the last couple years?

Winston Weinberg: So one of the first ones is because you’re—and it ties back to what you were saying, because you’re only paying attention to what is going, like, wrong right at the time at the company, every four months, I’d say, I get this mental block that is there’s too many things going wrong at the company and I can’t tend to all of them. That happens every—it’s about every four months. And what that means—so far, we’ve survived them every time. But what that means is I need to—there’s a different leadership hire I need. There’s a different structure in the company that I need, or there’s something I need to cut from the company, right?

And so it almost is like you have to just reinvent yourself as a founder every, like, four months or so, otherwise you are not going to be able to fix all of the things that are going wrong at the company. And I feel that pressure. Like, it’s weird. Like, I’m fine, and then once I do it, I feel very good for, like, the first month. And the second month I start feeling worse, and then the third, and then the fourth, and all of a sudden it is like this pressure system. And you have to figure out some way to, like, relieve that pressure system and then it unlocks the next thing of scale.

Brian Halligan: Okay, for me, it was—it often—I don’t know if this is—I’m just kind of testing if it feels the same. For me, it was kind of cranking along. Problems would start, dissension would start, things would get stuck. And, like, the thing that would unstuck it for me is a lot of the slowness or a lot of the things that were stuck was because decisions hadn’t been made, trade-offs hadn’t been made. And a lot of that was my being unsure and delaying that decision. So every once in a while, I don’t know if that was four months, to be like, I just need to make some decisions. I might be wrong, but I need to make decisions so the damn work can move forward. Is that how you kind of feel about it?

Winston Weinberg: Yes. The only thing I would say is for better or for worse, I make decisions insanely fast, which definitely can be a pretty big problem. What ends up happening is I haven’t decided who is the decision maker, right? And then that doesn’t scale. That’s a huge problem. Like, almost every problem that I run into, we have like six DRIs on. And it’s impossible. Like, no one was going to make a decision about this in the first place.

Brian Halligan: Yeah.

Winston Weinberg: And then I also think that one thing that I definitely messed up on in the beginning and I’m trying to get better at, is when you’re a really fast-growing company and everyone feels like there’s a lot of pressure on you, I think people feel like you can’t make mistakes. And that is actually the opposite of how I feel. Like, I would much rather people just try and make a decision and then it’s wrong and a week later they adjust and change, than they spend, like, three months not making a decision.

And I think something I did wrong and I am improving it is sometimes people would think that they were penalized or that I was upset about something or leadership was upset about something because they made the wrong decision and it failed. Not true. It’s because they took six months to make the decision. And by the time that that decision was made, the entire market has changed, our internal org has changed. It doesn’t make sense. And so right now, I think my number one hiring criteria is literally just bias for action. Like, that’s it. It is just, are you willing to take action and learn from those actions and then make a decision based off of that or iterate?

Brian Halligan: Yeah, let’s talk about that. You’ve hired a lot of people. The exec team has gone through a lot of change for you, which I think is typical of you growing that fast. Just kind of walk through some of those changes and what you’ve learned about hiring in that exec team. Like, what are some of the a-has that have hit you on the way on the team? Like, every founder I’m talking to, they want to talk about their team and it’s like, should I hire this person? Should I hire someone from the outside? Should I shoot this person? What should the org structure look like? What have you learned on all that?

Winston Weinberg: Okay, so I can say the number one thing that I have learned from, like, a hiring perspective, which is the main thing that I asked C Suite now to do if I’m going to hire them—or VP as well, is can you draw out what your org would look like in three months, six months and a year?

Brian Halligan: Yeah.

Winston Weinberg: It is insane how many people can’t do that. Like, it is wild to me that that is really hard for people to do. And there’s different levels of your ability to do that, right? Like, there is the ability of can you describe, like, “Oh yeah, I need a VP of this region and then a VP of that region,” and things like that. Whatever. No, it’s actually like, can you map out every single one of those hires, what they do, and can you think of who would be a good person or who would be a good fit for it, right?

That is, like, the number one thing that I see when I hire leaders and they don’t scale and is they do the same thing that I do poorly—or did poorly and I think I’m getting better at—which is what is your leverage team around you, right? Like, when you join, like what—and I think that there’s a little bit of founders are told, like, you don’t want to hire somebody who immediately wants to go hire more people, right? Like, that’s like, oh, they just want to build their org. Totally. But at the same time you want them to create leverage as quickly as humanly possible. And if they don’t create leverage for themselves, especially in the, like, glue parts of their function, they’re not going to be able to do the core competency of their function. It’s not going to happen. And I’d say that a lot of my time right now is actually spent with my leadership team figuring out who those lieutenants are for them and helping us all hire those.

Brian Halligan: I had a problem with trust building HubSpot. Like, there’s always a very small group of people who I was comfortable with. I was like, “Just go do it and figure it out, and I’m not really even going to worry about it.” And it frustrated my team that I didn’t have deeper trust. Do you have trust issues?

Winston Weinberg: Massive trust issues.

Brian Halligan: [laughs]

Winston Weinberg: Working on them. Working on them. Definitely. I mean, it is hard to let go. I also will say one thing. The hires that I’ve done a good job on are the ones where I was forced to do the role for, like, three months. I mean, I’ve never done this before. Like, I’ve never started a company before. And so if you have no idea, like, if you have spent zero time doing that role, you are going to hire the wrong person a hundred percent of the time. Like, there’s just no way, right? It’s hard for me to then get out of that.

Brian Halligan: Right.

Winston Weinberg: Like, it’s hard for me to, like, okay, that was my job and now I have to delegate part of that job. It’s hard for me. I’d say I kind of go back and forth on this of hire more leaders and give them more responsibility, and then also expand the group that I talk to daily, right? So one thing I’m trying to do a lot more of is we have like a—really simple things. Like, in Slack we have a leadership, like C suite, and then we have VPs and heads of and some other folks that are really good—ICs, et cetera, right? The leadership one is, like, seven people. The other one is almost 30, right? All of my thoughts about the market, general thoughts about the company, product direction, all of those that I’m constantly putting in there, I used to put them into only the seven people. Now I try to put 95 percent of it into the 30.

Brian Halligan: Why not the whole company?

Winston Weinberg: So for the whole company—I’ve thought about this, too. I’ve thought about just constantly posting in general chat. The problem with that is it just gets too distracting.

Brian Halligan: Fine.

Winston Weinberg: Like, we did that in the beginning of the company, and it just creates too many silos. And the reality is, like, some of the stuff I post in there is, like, crazy talk. Like, it’s like, “Hey, in, like, two years we should do XYZ.” Or, like, “This is a crazy idea.” And you don’t want too many—like, you want people that understand that that doesn’t mean, okay, let’s go build that from scratch, right? You want to make sure that it’s like a little bit tighter of a group than that. But I am trying to expand that group as much as I possibly can, because I don’t want that. I don’t believe in the whole idea of you can never talk to a skip level and you should never do that. Like, I think that’s bullshit. Like, I don’t believe in that at all.

Brian Halligan: Okay, let me just ask a couple very tactical questions that CEOs ask me all the time.

Winston Weinberg: Yeah.

Brian Halligan: 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, I look at a LinkedIn profile. Somebody’s a “Head of.” Like, what is that?

Winston Weinberg: I like “Head of” actually more than “Director.” 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 …

[CROSSTALK]

Brian Halligan: Okay. I get that, actually. That’s a good explanation. I get that.

Winston Weinberg: It’s all ownership.

Brian Halligan: I see.

Winston Weinberg: I think of all titles as just ownership, because the thing that everyone likes to do is just kind of squirm 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, right? 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.

Brian 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’s definitely going to die. It’s either going to get no water or it’s going to get too much water.”

[CROSSTALK]

Brian Halligan: And it’s dead. Is that the way you feel about it?

Winston Weinberg: Yeah, a hundred percent 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?” Right? That was option one. That usually doesn’t go that well. Instead, it is, this person should be in charge of this, right?

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

Winston Weinberg: So you can do that, but sometimes that takes a really long time, right? And what I’ve found 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? “Okay, 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.

Brian Halligan: [laughs] Okay.

Winston Weinberg: Because they didn’t want the—they were 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. And if you say there’s three things that are P0, you can hedge your bets. And if you built the wrong thing and you said, “Hey, this is a P0,” 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 P0s, 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. 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, 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 that about each thing.

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

Winston Weinberg: Too many big things is the answer.

Brian Halligan: Okay. How many you got? We would have four, and I would try to get it down to four.

Winston 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 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, and they have different needs. And we are honestly still trying to do kind of it all. And so I do think we are getting better at saying, “No, this is the P0, and that we do really well.” We’re not at the stage where we do four—if we pushed it down to four things, I think we’d 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 definitely do sometimes.

Brian Halligan: Okay.

Winston Weinberg: 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. Then you jump onto that. And I do think you can take more bets right now. Like, you can.

Brian Halligan: I do, too.

Winston Weinberg: Like, you can build really fast.

Brian Halligan: You can get more shit done now.

Winston Weinberg: You can. Yeah.

Brian Halligan: Okay. I have a lot more questions. I have two on the org. 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 it sends to 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?

Winston Weinberg: Tell them about it. And I’ve done this wrong, too. Like, I have—I mean, it’s actually weirdly similar to the P0 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 am 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 almost everyone that is doing their part of the company can do a better job than me. And if they can’t, I am hiring someone who can. Like, I should not be the 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, 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 growing too fast. And you just 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 them like a mentor.

Brian Halligan: I got layered twice in my career—so I’m old. I got layered twice in my career. Once, there’s a lot of heads up and a lot of feedback that I wasn’t quite ready and that we 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.

Winston Weinberg: Yeah.

Brian Halligan: In another instance, I kind of got happy talk, and I thought it was doing pretty well. Maybe didn’t think I was killing it, but pretty well. And out of the blue they said, “Hey, we’re going to bring someone over you.” I left in that case. And my sense on this stuff is just surprises are never good, feedback’s underrated. And overall, if I look at the history through HubSpot or, [inaudible] on my whole career, like, when layering happens, about 50 percent of the time, that person who gets layered a year later is gone.

Winston Weinberg: 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.

Brian Halligan: Yeah.

Winston Weinberg: Right? And especially if they were a star, because, like, if they were a star, then that’s an incredibly important part of your business, and they will really block the person from joining.

Brian Halligan: Yeah.

Winston Weinberg: Like they massively block that person. I don’t know. 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. Like, even more bring them along and just risk it.

Brian Halligan: Okay, you hired Katie Burke, HubSpot’s chief people officer.

Winston Weinberg: Yep.

Brian Halligan: Tell me about her, why you hired her. And then you just promoted her to COO. What does a COO do inside a company like yours? And should 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 [inaudible]. 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 JD, and we sat in the order: JD 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 to introduce himself is JD, who had just started as COO. And Ben just was like, “Why? And what are you doing?” And, like, 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 podcast, I’m going to ask him about this. And he’s obviously very wise. What does your COO actually do?

Winston Weinberg: Yeah. I mean, so a couple things here. One, one nice thing about GTM is you have objective measures, right? So you can be like, okay, did they hit these quotas, et cetera, [inaudible]. And you can kind of test, right?

Harder on engineering. Like, sure, you can do, like, code shift, et cetera, but not an insanely good metric, right? One maybe metric for Katie: 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, 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 slacks sent is, like, performance, but it does have some indicator of, like, how involved you are in the company, right? And she, Katie, basically was the COO probably six months ago, I would say, in all but title, right? And I think it’s different for every company, right? So I am definitely one of the founders who I like 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 in 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.” And that is awesome. And it works for a bunch of folks.

Brian Halligan: There’s a bunch of companies doing that.

Winston 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 kind of basically run GTM.

Brian Halligan: That’s not her.

Winston Weinberg: 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 a lot closer to a partner, like throughout the entire process. So, you know, I have, like, an operating cadence personally. I have a—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. And then it has like a daily. And then I copy, paste and refresh it every single day. And you go through …

Brian Halligan: Wait. Talk about a little more detail. I want to hear that.

Winston 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.

Brian Halligan: [laughs]

Winston Weinberg: There’s some other ones on there, but I’ll tell you, you’re actually on there. And then I have basically metrics that I’m tracking. So, like, renewal rates, like product usage, DAU over MAU. 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, these are big things. And they’re all cross functional.

Brian Halligan: Like what?

Winston 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, 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, head of product, VP of product, all of those people, 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. Earlier on you said, “Hey, how do you pick your priorities? How do you make sure you’re doing all of 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. 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 that 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.

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

Winston Weinberg: Yeah, so I have a chief of staff and the biggest …

Brian Halligan: Not an assistant, a chief of staff.

Winston 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 and I want to track all those things. That is something the chief of staff would do.

Brian Halligan: Okay, what about, like, admin stuff? Like, somebody who books your travel, somebody who, you know, does all your shit, like, all your personal stuff. Like, there’s so much.

Winston Weinberg: Yeah, I have that as well. I have that as well. I took way too long to do that. I was still—I was booked …

Brian Halligan: So you have someone that does?

Winston Weinberg: 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 was like something like that. It was so stupid. I mean, it was the dumbest thing ever. Like, I remember 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, they thought it was fraud because I had never—you know, it was like a $6,000 flight or something crazy like that from SF to UK, and I had never paid for anything like that, like, personally. And JP Morgan was just like “Complete fraud.” And it was like six hours.

Brian Halligan: Yeah.

Winston Weinberg: And I thought back to that other day, and I went to Gabe and he was just like, “What the fuck have you been doing all day?”

Brian Halligan: Yeah.

Winston Weinberg: It was that.

Brian Halligan: 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, and 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 in legal, how do you go about nailing your first five customers?

Winston 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 used to do for all lawyers is if you’re a litigator, everything needs to be filed with a federal court 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, like, document repository called Pacer. 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.”

Brian Halligan: Yeah.

Winston Weinberg: 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 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. Like—and if you think about doing a Zoom with a lawyer, it’s like, I don’t know how you got on this Zoom. Like, I don’t really pay any attention to this. Half of them were doing this, like, literally like this on the Zoom, right? And then you bring up, “Hey, I saw that you filed XYZ, you know, 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 like 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.

Brian Halligan: Tell me about that. It’s kind of counterintuitive.

Winston Weinberg: The thesis was kind of twofold. One is I’m insane, 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 is just like, why not use ChatGPT, right? For way, way, 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, it can review your lease. That’s just going to happen, 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, 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 a perfect design partner for the entire legal industry, right? Like, the reason these firms exist is because when you’re doing, you know, a massive M&A that involves 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. And so they’re really good design partners.

Brian Halligan: Their requirements are brutal. It’s 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 the deal just happens. And then move up. That’s the conventional wisdom. Why? You tortured yourself.

Winston Weinberg: Well, I mean, so a couple of things here. Weirdly, revenue growth, like how fast can you gain revenue, was not something we were thinking about. Like, another thing to think about here is like, I didn’t know what ARR was in the beginning. I didn’t even know what that was. Like, I didn’t even know of like, oh, company health, like net new ARR, quarter over 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 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.” Right? And it’s the same on corporates. So now, like, last quarter I think it was like, 42 percent 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 to everybody else, right? And so some of it is just do the hard thing.

Brian Halligan: Back to the first ones. Like, so many of the CEOs I’m working with get their first accounts because they worked for that company before or their VC knew somebody at that company. It doesn’t sound like that was the game you played. 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.

Winston Weinberg: A hundred percent 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’d been practicing law for, like, eight months. So I didn’t have any connections.

Brian Halligan: Right.

Winston Weinberg: It really was just could you get people that would respond to your LinkedIn message? I mean, just LinkedIn. Like, you’d message a thousand people. Like, and 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, and they messaged me back and be like, “Oh, love Harvey,” right? Or something like that.

Brian Halligan: Okay.

Winston Weinberg: 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.

Brian 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 1 to 100 on how much mojo you had on the internet—how many links you had, your SEO power, your blog, your social. And 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?”

Winston Weinberg: Yeah.

[CROSSTALK]

Brian Halligan: I don’t have any marketing salesperson. Like, talk to this guy! So I immediately got to the pain, and I immediately got some credibility through it. And then the sales rep would show up and, like, explain the report and show a demo. It’s like, 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 numb it? Yeah, that’s HubSpot. And so sort of the pain factory. And I think what you did is exactly what we did.

Winston 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? And that is going to cause friction. 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.

Brian Halligan: Yeah.

Winston Weinberg: And so their pain was I don’t want to do this particular piece of my job.

Brian Halligan: Right.

Winston Weinberg: 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. And law firms have different pain points, especially as AI develops, than just the lawyers themselves do, right?

Brian Halligan: Yeah.

Winston Weinberg: So you have to kind of 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.

Brian Halligan: No.

Winston Weinberg: And that helps the business, right? 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, gets better and better, you got to think about not just the individual user, but what is the pain point of that industry?

Brian Halligan: Yeah. You didn’t know anybody in these big law firms. You also had never sold anything.

Winston Weinberg: Yeah.

Brian Halligan: Or built a go-to market engine. And so many of the CEOs I’m working with are the same. Like, by the way, you’re quite different than most of the CEOs I work with because most of them are software developers.

Winston Weinberg: Yeah.

Brian Halligan: And deeply technical and product people. And then they built something amazing and they’re like, “I have to sell this thing?” [laughs] 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.

Winston Weinberg: So I think there’s a couple 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.

Brian Halligan: Yes.

Winston Weinberg: It’s not even close. It’s like actually not even close. 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 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.

Brian Halligan: Makes sense.

Winston Weinberg: If you do one or the other, it actually, like, doesn’t work at all. So I want to 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. 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 become champions, it completely changes everything. And so it’s kind of what you said before where honestly 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 two [inaudible] stuff, it actually doesn’t work.

Brian Halligan: Okay. A lot of my CEO founders, some are in really sexy businesses, and it’s easier to hire developers to build sexy stuff.

Winston Weinberg: Yeah.

Brian Halligan: Don’t take this in any offense, but building legal software doesn’t feel that sexy. [laughs] How are you able to attract top tier engineering talent on building software for lawyers?

Winston Weinberg: Yeah, the biggest reason is because we have to work—there are a lot of actually, like, 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?

Brian Halligan: I saw that.

Winston Weinberg: 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 ChatGPT memory, Anthropic memory, et cetera, there is actually no, like, understanding of these are the documents as artifacts, and things like that, right?

Brian Halligan: Super irritating!

Winston Weinberg: Super irritating. But that’s something that they will solve eventually. If we don’t solve that, our product goes to zero, right? And so there’s actually tons of frontier-type things that I think these application layer terms could do.

Brian Halligan: Okay. So they’re hard problems.

Winston Weinberg: Really hard problems that everyone is going to have to solve eventually, 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.

Brian Halligan: Yep.

Winston Weinberg: Also something the big labs have not solved yet.

Brian Halligan: Right. Irritating that they haven’t.

Winston Weinberg: But they haven’t. 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.

Brian Halligan: Yeah yeah yeah yeah yeah.

Winston 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.

Brian Halligan: I want to talk about you a little bit.

Winston Weinberg: Okay.

Brian Halligan: Something I noticed about you, and I spoke to some people who work for you. And 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. Why do you have a chip on your shoulder?

Winston Weinberg: Yeah.

Brian Halligan: Something from your childhood?

Winston Weinberg: [laughs] I think it’s a combination of things. So I always let my co-founder, whenever we do, like intros, I always let my co-founder go first. And he has an awesome background.

Brian Halligan: Amazing, yes.

Winston Weinberg: Incredible background. And then I go, “I did nothing for 27 years” is like what my—well, now I’m a little older, but that was basically my background. I think the reality is, like, 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 kind of like kicked out of a bunch of schools and things like that. And I didn’t find something that made me, like, want to get up every morning and, like, apply myself.

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’s 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. I don’t feel like what I’m getting up to do sucks. And, like, one example of this is I literally 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 …

Brian Halligan: Were you always like that? That’s pretty intense and not that fun. Were you always that way?

Winston Weinberg: No. 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 myself in situations where I would find those things.

Brian Halligan: What changed inside of you that all of a sudden you were …?

Winston Weinberg: Yeah, I’m still figuring that out, to be a hundred percent honest. Like, the part that I have figured out is what motivates me. And that took me—like, I think I figured out 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, “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, and it was 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? There’s so many different ways why you can get stopped, but it’s not physically you 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 felt before this.

Brian Halligan: Got it. Do you think there’s a downside of your intensity? And let me just—I’m interviewing H.R. McMaster, who’s very nonpartisan, but he was a nonpartisan national security advisor in the first Trump administration. He lasted, like, 14 months. And he left/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 nonpartisan podcast. I’m not casting any dispersions on anyone. Do you—are you a little like that?

Winston Weinberg: I think sometimes. I’m trying to get better at it.

Brian Halligan: Yeah.

Winston Weinberg: But I think yeah. 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.” Like, 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? But I do feel that.

Brian Halligan: Okay. I’ve known you for a while now. I’m really proud of you.

Winston Weinberg: Thank you.

Brian Halligan: You’ve come so far and matured so much, and you’re doing such an excellent job. I’m really happy to know you and happy Sequoia invested in you. I think you’re doing great.

Winston Weinberg: Thank you, man.

Brian Halligan: I’m really proud of you.

Winston Weinberg: Thank you.

Brian Halligan: Yeah.

Winston Weinberg: That means a lot.

Brian Halligan: Appreciate you coming on the pod, giving the pearls of wisdom to all the CEOs out there. And go get them. Keep the rocketship going.

Winston Weinberg: Thank you.

Brian Halligan: Yeah.

Winston Weinberg: Thank you, man. Thanks.

Takeaways

Brian Halligan: Okay. I hope you liked 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. 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 meeting him, 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, 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 the K is knowledgeable, he’s 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. 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.