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

Summary

Long Strange Trip: CEO to CEO with Brian Halligan

Episode: Harvey CEO Winston Weinberg: Why You Should Reinvent Yourself Every 4 Months
Host: Sequoia Capital
Date: January 15, 2026

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Episode Overview

In this episode, Brian Halligan sits down with Winston Weinberg, co-founder and CEO of Harvey, a rapidly scaling AI legal startup. The conversation dives into the turbulent path of hypergrowth, company building, hiring, and reinvention, as Winston reveals the emotional, organizational, and operational realities behind running one of the industry’s fastest-growing companies. Listeners get candid, counterintuitive insights into scaling, executive hiring, organizational structure, decision-making, and dealing with personal intensity as a founder.

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Key Discussion Points & Insights

1. The Reality of Hypergrowth at Harvey

• Growth Stats: Harvey’s at a $190M run rate (4x from last year), 500 employees (2x from last year).
• Surprise Factor: Internally, the company feels chaotic with a lot of machinery still missing—even at scale.
  • "I think my number one hiring criteria is literally just bias for action. Like that's it." (Winston, 00:00 & 10:37)
• Constant Reinvention: Winston believes every four months, founders must reinvent themselves to keep pace with problems and organizational scale.
  • "Every six months you have to re-earn your position in the market… including myself." (Winston, 04:43)

2. The Tension Between Success and Self-Critique

• Internal vs. External Perception: External praise rarely matches Winston's internal expectations; high achievement doesn't prevent constant self-critique.
  • "You have to re-earn your position at the company… every six months, you absolutely have to change." (Winston, 04:43)
• Celebrating Wins vs. Obsessing Over Problems: Winston—like the host—focuses on problems over celebrating successes, sometimes missing opportunities to accelerate what’s working.
  • "If something's going super well, I just don't think about it… 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." (Winston, 05:39)

3. Coping with the Speed of Change

• Every Four Months: Crisis & Redesign: Winston describes a predictable cycle of overwhelm and reinvention.
  • "Every four months, I'd say I get this mental block that is there's too many things going wrong… you have to reinvent yourself as a founder." (Winston, 07:32)
• Decision-Making and Bias for Action: Fast decision-making is central. The main hiring filter is action over inaction.
  • "If I would much rather people just try and make a decision and then it's wrong. And a week later they adjust and change." (Winston, 09:26 & again verbatim from the intro at 00:00)

4. Hiring, Layering, and Building an Executive Team

• Scaling the Org: Drawing the Map: When hiring execs, Winston asks candidates to map their own org for 3, 6, and 12 months, focusing on their ability to create leverage.
  • "Can you draw out what your org would look like in three months, six months and a year? …It is insane how many people can't do that." (Winston, 11:35)
• Massive Trust Issues—but Working On Them: Delegating is tricky, but necessary. The best hires are after Winston does the job himself.
  • "Massive trust issues. Working on them." (Winston, 13:34)
• Communicating More Broadly: Expanding communication beyond the C-suite unlocks more scale but selectively; not every experimental idea should go company-wide.
  • "All of my thoughts about the market... now I try to put 95% of it into the 30." (Winston, 14:10)
• Titles and Ownership: Prefers "Head of" over "Director" for accountability; clarity is crucial.
  • "I think of all titles as just ownership because the thing that everyone likes to do is just kind of squirm out of ownership." (Winston, 16:34)
• DRI (Directly Responsible Individual) Philosophy:
  • "If you're going away for a month and you ask two friends to water your plant, the plant's definitely going to die." (Host quoting analogy, 17:01)
  • "If you say that person's in charge, they're in charge." (Winston, 17:57)

5. Focus, Priorities, and Platform Building

• Too Many Big Projects: Winston admits to running too many big initiatives but is working on improving discipline.
  • "We have way too many things… The P0 will always be done extremely well." (Winston, 20:07)

6. Layering Talent and the Stress Around It

• The Pain of Layering: Winston has layered high performers and learned to bring them along for the process, even at the risk of losing them.
  • "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." (Winston, 22:01)
• Feedback & Transparency: Surprises are never good—bring people into the process early and frequently when layering or changing org structures.
  • "When layering happens, about 50% of the time, that person who gets layered a year later is gone." (Host, 24:12)

7. Role of COO, Chief of Staff, and Support Structure

• COO Responsibilities: Katie Burke, former HubSpot Chief People Officer, promoted to COO—doesn't just "run the trains," but acts as a partner across cross-functional projects.
  • "Her role is like a lot closer to a partner, like throughout the entire process… the number one thing at our company is hiring." (Winston, 28:53)
• Chief of Staff vs. Admin vs. COO: Chief of staff manages Winston’s personal and direct tasks, COO manages cross-functional company-wide efforts, and an admin handles logistics.
  • "Chief of staff… everything that I need to individually do myself. And Katie manages everything that is cross functional." (Winston, 32:34)

8. Go-To-Market Strategy—Personalized, Pain-driven, and Counterintuitive

• Winning Early Customers: Extreme personalization and “pain factory” tactics—showing top tier lawyers flaws in their filings to get their attention.
  • "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." (Winston, 35:02)
• Do the Hardest Use Cases First: Rather than starting easy, Winston targeted the most demanding big clients to force the product to mature quickly.
  • "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." (Winston, 36:43)
• No Warm Intros—All Cold Outreach: Winston didn't leverage a network; his approach was pure hustle and personalization.
  • "It really was just. Could you get people that would respond to your LinkedIn message?" (Winston, 40:03)
• Product and Selling Go Hand in Hand: He’s best at building product when closely selling to customers.
  • "The times that I'm best at product is when I'm selling the most. It's not even close." (Winston, 45:01)
• Reading People and Objections: Most valuable insights come from turning around skeptical, even antagonistic, buyers.
  • "Number one thing to do is to meet with that person one on one." (Winston, 45:01)

9. Building Engineering Teams for “Unsexy” Legal Tech

• Frontier Problems Are a Lure: Harvey faces “frontier” technical challenges (like document-based memory and multi-company collaboration) that attract talent.
  • "There are a lot of actually like frontier things that we need to solve… we have to solve sooner because of just the nature of our customer base." (Winston, 47:10)

10. The Source and Cost of Intensity

• Motivation: Intensity comes from a “chip on the shoulder” and a longing for challenge after years of feeling aimless.
  • "When I started this company, I had no idea that this would happen. But I've never felt this in my life." (Winston, 49:58)
• Fear of Losing the Feeling: Winston actively seeks discomfort and challenge, fearing a return to feeling disengaged in life.
  • "Terrifying to me to lose that… every week to have at least like two to three things that make me super uncomfortable." (Winston, 51:24)
• Self-Critique of Intensity: He acknowledges the downside—sometimes pushing people too hard—and is working on delegating more effectively.
  • "Sometimes I think I take it too far. And I think it becomes a problem." (Winston, 53:39)

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Notable Quotes & Memorable Moments

• On Fast Decision-Making:
  • "Right now I think my number one hiring criteria is literally just bias for action. Like, that's it." – Winston Weinberg (00:00)
• On Reinventing as a Founder:
  • "It almost is like you have to just reinvent yourself as a founder and 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." – (07:32)
• On Delegation and Trust:
  • "If you have spent zero time doing that role, you are going to hire the wrong person 100% of the time." – (14:10)
• On Ownership and Accountability:
  • "I think of all titles as just ownership because the thing that everyone likes to do is just kind of squirm out of ownership." – (16:34)
• On Go-To-Market Tactics:
  • "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." – (35:02)
• On Motivation:
  • "I just want to see how far I can go and like, keep going until I'm like, this is a… Scale or this is a type of project or something that I am not good enough to do." – (51:45)
• On Intensity’s Downside:
  • "Sometimes I think I take it too far. And I think it becomes a problem." – (53:39)

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Timestamps for Major Segments

• 00:00–00:48 — Winston on mistakes, bias for action as #1 hiring filter
• 01:55–03:12 — Becoming a billionaire, life unchanged
• 03:12–05:39 — Harvey’s internal chaos, constant reinvention
• 05:39–07:09 — Focusing on problems, missing celebration opportunities
• 07:32–09:26 — Reinventing every 4 months, dealing with overwhelm
• 09:26–11:02 — Fast decisions, empowering action, not penalizing mistakes
• 11:02–14:10 — Hiring execs, drawing the org, trust issues, broadening communication
• 15:53–17:57 — "Head of" titles, DRI, the plant analogy
• 19:43–21:27 — Number of big company initiatives, P0 discipline
• 22:01–25:47 — Layering people, dealing with the risk, feedback, retention
• 25:52–32:20 — Role of COO, operational cadence, leverage scaling
• 32:29–34:21 — Chief of staff vs. admin, delegation evolution
• 35:02–41:02 — Go-to-market: targeting tough customers, cold reach
• 41:44–45:01 — Using pain to sell, product-building linked to selling
• 47:10–49:10 — Attracting engineers with hard problems
• 49:44–54:30 — The roots and double-edged sword of Winston’s intensity

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Final Thoughts

This episode provides an unusually raw and practical playbook for hypergrowth CEOs. Winston Weinberg’s approach is relentless, self-critical, and highly tactical—with a clear theme: continuous, uncomfortable reinvention is the requirement for scaling through chaos. For founders on a similar “long strange trip,” the value lies in embracing bias for action, building leverage at every level, and not only tolerating, but actively seeking, the discomfort that comes with hypergrowth leadership.

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If You Only Take Away a Few Things

• Reinvent yourself—and your org—every few months, or risk breaking.
• Relentless bias for action > avoidance of mistakes.
• Hire (and retain) execs who can map—and grow—their own leverage.
• Deep transparency, direct ownership, and feedback loops are essential.
• Great product insight comes from being in the customer’s pain cycle.
• Intensity is a tool—use it wisely, and know its costs.

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(End of summary.)

Transcript

[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. Then 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.

[Interviewer]

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 Companies at Harvey, 190 million run rate and that's 4x from last year. They're at about 500 employees. There's about 2x from last year. So the company is absolutely ripping. He's at the head of a real rocket ship. 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. How does it feel to be the world's newest, at least on paper, billionaire?

[Winston Weinberg]

Is it? Is it newest? I actually not even sure if that's true.

[Interviewer]

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 know like, 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. And I think it's more just like why Move. Like, we like the apartment, we like living together. Like, I don't know.

[Interviewer]

I think what's interesting to other CEOs who are listening is, I mean, you're the head of a rocket ship, 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 that's like. I think there's. 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, we. 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, etc. 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, by the way,

[Interviewer]

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, 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, you. Including myself. Like, and every six months, you absolutely have to change. And if you don't, I think you just break Okay, I got a bunch

[Interviewer]

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 in like obsessing over what was going wrong and was not very good at celebrating the successes. I got 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. And I'm going to go spend time on something else.

[Interviewer]

Right.

[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.

[Interviewer]

Right.

[Winston Weinberg]

And so there have been instances in the past where I've said, you know, I've kind of 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.

[Interviewer]

Right.

[Winston Weinberg]

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 you're. It's going really well. Right. That, I think, is the, 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 to and try something even harder.

[Interviewer]

I've been on the journey with you for the last 18 months or so. A lot has changed in, in very fast scaling. Like, you're doing what has broken. Like, what breaks along the way. Like, it helps. Like, as we feel 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. At the time. At the company. They're. 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 and 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, it. I'm like, 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.

[Interviewer]

So, 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 that 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 I 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 is 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 just. It's impossible. Like, no one was gonna make a decision about this in the first place. 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 if I would much rather people just try and make a decision and then it's wrong. And a week later they adjust and change. Then 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?

[Interviewer]

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 ahas 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 layer this person? Should I hurt 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]

The. 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?

[Interviewer]

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?

[Interviewer]

Right.

[Winston Weinberg]

That is like the number one thing that I see when I hire leaders and they don't scale and is they're. 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?

[Interviewer]

Right.

[Winston Weinberg]

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 human, humanly possible. And if they don't create leverage for themselves, especially in the like, glue parts of their function. Right. 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.

[Interviewer]

I had a problem with trust building HubSpot. Like, there's always a very small group of people who I was comfortable with, 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. Working on them. Working on them, definitely. I mean, it's. It is hard to let go. I also will say one thing.

[Interviewer]

I.

[Winston Weinberg]

The hires that I've done a good job on are the ones where I had. I was forced to do the role for, 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 100% of the time. Like, there's just no way. Right. It's hard for me to then get out of that.

[Interviewer]

Right, 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. Is this really simple things like in Slack we have a leadership like C suite. And then we have VPs and head of. And some other folks that are really good ICs, etc. Right. The leadership line 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% of it into the 30.

[Interviewer]

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. 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 X, Y, Z 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. Okay, let me just ask a couple

[Interviewer]

of very tactical questions that CEOs ask me all the time. Yeah. You just brought up Heads of as a title. What the hell is that? Why do you ask them what's wrong with Director or VP or Manager? What the hell is a heads up? Like, 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 this responsibility.

[Interviewer]

That's a good explanation. I get that.

[Winston Weinberg]

It's all ownership. I see. 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.

[Interviewer]

Right.

[Winston Weinberg]

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.

[Interviewer]

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. 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 just constantly water and it's dead. Do you feel. Is that the way you feel about it?

[Winston Weinberg]

Yeah, 100%. That's how I feel about it. And then it takes. 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?

[Interviewer]

Why. Why can't you get feedback on who should be in charge?

[Winston Weinberg]

And so you can do that, but sometimes that takes a really long time, right? And. 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? 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 P zeros. And actually, recently, last quarter, uh, someone, I definitely made fun of them for doing this. They made a P00, okay? Because they didn't want the P. 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 P zeros, 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 like, 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 who, 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.

[Interviewer]

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.

[Interviewer]

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 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. 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'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. 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.

[Interviewer]

I do too.

[Winston Weinberg]

Like, you can build really fast, get

[Interviewer]

more shit done now.

[Winston Weinberg]

You can. Yeah.

[Interviewer]

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 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.

[Winston Weinberg]

And I've done this wrong too. Like, I have. This is. 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 do 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 there are 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 a 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. 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, 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, 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 them like a mentor.

[Interviewer]

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, I, 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. Yeah, 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 PTC on my whole career, like when layering happens, about 50% 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. 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.

[Interviewer]

Right.

[Winston Weinberg]

Like they massively block 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. Like, even more. Bring them along and just risk it.

[Interviewer]

Okay. You hired Katie Burke, HubSpot's chief people officer.

[Winston Weinberg]

Yep.

[Interviewer]

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, David 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 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 is just JD who had just started the 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, there are one nice thing about GTM is you have objective measures, right? So you can be like, okay, did they hit these quotas, et cetera, Eje. 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 Slack Scent 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 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 in partnerships. I like working on hiring. I like working on everything. So it. 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.

[Interviewer]

There's a bunch of companies doing that, tons.

[Winston Weinberg]

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.

[Interviewer]

That's not her.

[Winston Weinberg]

That, that's not what Katie's doing. What Katie is doing is basically every other part of the business combined. And so she, 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. 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.

[Interviewer]

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 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.

[Interviewer]

Like what?

[Winston Weinberg]

Like we need to revamp our pilot process. Right. So That's a really good example where revamping pilot process revol 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, CTOs involved, had a product, VP of Product, all of those people, Right. And then I still just made a decision at the end of the day.

[Interviewer]

Right.

[Winston Weinberg]

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 are really good are not being pushed down by, by people above them that are not as good. Right. In 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.

[Interviewer]

Okay, let me answer 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.

[Interviewer]

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 chief of staff would do.

[Interviewer]

Okay, what about like admin stuff? Like somebody who books your travel, Somebody who, you know, does all your, like all your personal stuff. Like there's so much.

[Winston Weinberg]

Yeah, I have that as well. I have that as well. I. I took way too long to do that. I was still. I was booking.

[Interviewer]

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's like something like that. It was so stupid. I mean, 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, 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 on my flight or like personally and JP Morgan was just like complete fraud. And it was like six hours.

[Interviewer]

Yeah.

[Winston Weinberg]

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, who's that?

[Interviewer]

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 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. The thing that AI allows you to do is personalize everything to an insane degree. And now there's incredible tools like clay and etcetera, for like actually doing this at scale. But you could do it by yourself. Right. So the thing that I would used to do for all lawyers is you can. If you're a litigator, everything needs to be filed with a 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, 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.

[Interviewer]

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, 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. 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 on the transactional side too. You just know, 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. So tell me about that. Yeah.

[Interviewer]

So 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, 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. 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 like a perfect design partner for the entire legal industry, right? Like, the reason these firms exist is because when you're doing a, you know, a massive M and 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. And so they're really good design partners.

[Interviewer]

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. That 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.

[Winston Weinberg]

Why you're tortured. Well, I mean, so a couple of 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 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, like 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 like 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% 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, 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

[Interviewer]

do the hard thing 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 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 bowled your way into your early deals.

[Winston 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. Um, and I also. I've been practicing law for like, eight months. Um, so I didn't. I didn't have any connections. Right. Um, 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. They messaged me back and be like, oh, love Harvey. Right? Or something like that. Okay. 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.

[Interviewer]

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? 100?

[Winston Weinberg]

Yeah. Yeah.

[Interviewer]

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, 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 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.

[Interviewer]

Yeah.

[Winston Weinberg]

And so their pain was I don't want to do this particular piece of my job.

[Interviewer]

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 part 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. 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, you're just pitching to them. Right. And it's because, you know, you get like a big, 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. 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.

[Interviewer]

Yeah. You didn't know anybody in these big law firms. You also had never seen sold anything.

[Winston Weinberg]

Yeah.

[Interviewer]

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.

[Interviewer]

And deeply technical and product people. And then they built something amazing. You're 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.

[Winston Weinberg]

I I. So I think there's a couple ways to do it. One, 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.

[Interviewer]

Yes.

[Winston Weinberg]

It's not even close. It's. 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 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 247 and talk and working on product simultaneously. 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 greenfield stuff, it actually doesn't work. Okay.

[Interviewer]

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.

[Interviewer]

Don't take this at any offense, but building legal software doesn't feel that sexy. 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.

[Interviewer]

Right.

[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.

[Interviewer]

Right. 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.

[Interviewer]

Okay.

[Winston Weinberg]

So they're hard problems, 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. Yep. Also something the big labs have not solved yet.

[Interviewer]

Right. And we irritating 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 p zeros it's like it's way down that. 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.

[Interviewer]

I want to talk about you a little bit.

[Winston Weinberg]

Okay.

[Interviewer]

Something I noticed about you and then 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. Childhood. I think it's a combination of things. So I always let my co founder whenever we do Introduction, like intros. I always let my co founder go first. And he has an awesome background.

[Interviewer]

Amazing, yes, incredible background.

[Winston Weinberg]

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, 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, I was a terrible student. Didn't 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, 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.

[Interviewer]

You've always like, this, that's pretty intense and not that fun. Were you always that way or like.

[Winston Weinberg]

No, I, 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 myself in situations where I would find those things.

[Interviewer]

What changed inside of you that all of a sudden you were.

[Winston Weinberg]

Yeah, I still figuring that out. To be a hundred percent honest, like, the, 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, 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, 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. 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.

[Interviewer]

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, 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 nonpartisan podcast and casting any dispersions on anyone.

[Winston Weinberg]

Do you.

[Interviewer]

Are you a little like that?

[Winston Weinberg]

I think sometimes I'm trying to get better at it.

[Interviewer]

Yeah.

[Winston Weinberg]

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. Like, that is sometimes how it happens. Sometimes I think I take it too far. Um, 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.

[Interviewer]

Okay. I've known you for a while now. I'm really 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 invest in you. I think you're doing great.

[Winston Weinberg]

Thank you, man. I'm really proud. Thank you. Yeah, that means a lot.

[Interviewer]

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.

[Winston Weinberg]

Thank you. Yeah, thank you, man. Thanks.

[Interviewer]

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 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 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 Nikay's knowledgeable, 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 CC 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.