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

Winston Weinberg is the CEO and Co-Founder of Harvey, the leading professional services platform engineered with AI for law, tax, and finance. Winston has raised over $980M for Harvey from Sequoia, a16z, GV, Elad Gil and more with a last round price of $9.2BN post-money. Before founding Harvey in August 2022, Winston was an attorney at O'Melveny & Myers LLP, specializing in antitrust and securities litigation. ----------------------------------------------- Timestamps: 00:00 Intro 04:16 #1 Thing Every Founder Needs to Do Everyday 13:35 Why VCs Suck at Helping Companies Hire? 15:26 How to Get Sequoia and a16z Term Sheets 25:49 What No One Understands About Enterprise AI Adoption 38:21 AI's Impact on Professional Services 39:14 Future of Law Firms: Do They Die? 43:17 What Everyone Should Know That No One Tells You About Hiring in Europe 48:54 I Have Massive Trust Issues… 55:55 Biggest Lessons on Effective Deal-Making 01:01:30 Cold Emailing OpenAI and It Leading to a Term Sheet 01:05:10 Quick Fire Round ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Winston Weinberg on X: https://twitter.com/winstonweinberg Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #winstonweinberg #ceo #keithrabois #aiadoption #founderadvice #patgrady

Winston WeinbergguestHarry Stebbingshost
Jan 19, 20261h 13mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 4:16

    Intro

    1. WW

      I think the value of B2B SaaS is about to become astronomical.

    2. HS

      Do you think we're seeing a plateauing in performance across the different model providers?

    3. WW

      I think that we're seeing a plateau in performance for consumer use cases. Probably what's gonna happen is the economy's gonna explode, these companies are gonna have crazy expectations for what they can do. I think a lot of people in deals, they think that movement is action. Not true. The second piece is know when to not negotiate. This, I think, is actually really, really important. There are certain deals where you want one thing from the deal and nothing else matters. If you wanna hire somebody, hire them, whatever they want, and put them in the position that they want. If you can't tell if they're best in class, that's a separate problem, but don't go back and forth.

    4. HS

      Were you nervous pitching to Mark and Ben?

    5. WW

      Um-

    6. HS

      You knew them coming in.

    7. WW

      Yeah, definitely.

    8. HS

      What existential threat today concerns you most? [upbeat music] Ready to go? Winston, dude, it is so good to finally meet in person. It's so great to have you in the studio. I've heard many great things for a while, because it was Sarah Guo that found you first, before Pat, I heard.

    9. WW

      Yeah, I know. If, if Pat's listening, uh, he definitely needs to give some credit to Sarah here. Yeah, Sarah actually was... So our f- our first investor was OpenAI, um, and then our first two angel investors were Sarah Guo and Elad Gil.

    10. HS

      Uh, dude, I, [chuckles] one, I love the way that under 30 seconds we've already done a sucker punch to Pat. [laughing]

    11. WW

      [laughing]

    12. HS

      But, but two, I, I just wanna start actually on something that shows a little bit about your character, and it was a story that Pat told me. He said, "Ask him about running a mile, the time that he did it first, and how that progressed, 'cause it's very revealing of his character." Can you tell me this story?

    13. WW

      Yeah, so I, I, I played sports when I was in high school, and then didn't as much when I was in college. And, you know, when you start a startup, things get pretty stressful. Uh, and I had a mentor who gave me advice of basically like, "Hey, stop lifting so many weights and, like, start trying to run a mile." And I remember when I started running a mile, I think I was at, like, eight minutes or something. [chuckles] It was really, really bad. I was, like, pretty out of shape. Um, and I had basically a goal to get up every single morning and just reduce my mile time as fast as possible. And the way that I did it is, I'm gonna run one mile no matter what, and then just kind of see if I can reduce the back end of the mile again, down, down, down, down, down, until I can get to as fast as I possibly can. Um, and it... The, the outcome of that, which I think really helped, was, and, and something I'm actually trying to do more and more in my life is, every morning when I wake up, I get up pretty early, and I just try to destroy myself and run as fast as I possibly can. It just reduces my stress for the rest of the day. And I've found that, like, over time, a lot of company building is just making very good decisions. And if you start your day off with basically something that is kind of, I don't know, very challenging in a physical way, you kind of, like, have this stress relief through the rest of your day. Your body has, like, absorbed that stress. And I very much believe that in everything else, too. Like, I try to do a stressful thing every, every week, because I think a lot of it is, like, stress tolerance over time.

    14. HS

      Can I ask, what decision have you made to your daily routine life that has had the biggest positive impact? So, like, one for me is, like, I drink a liter of water when I wake up-

    15. WW

      Yeah

    16. HS

      ... and it just makes me feel [chuckles] like I've accomplished something very quickly, and I'm hydrated fast.

    17. WW

      Yeah, yeah.

    18. HS

      What would yours be?

    19. WW

      I think it's getting up early. Um, it, it's helped a lot. I think, also, like, we're in 60 countries now, and so no matter what, I try to keep basically East Coast time. So when I'm in San Francisco, I'll get up at, like, 4:00 AM or 4:30 AM. And what that allows you to do is you can kind of, like, focus before the stream of Slacks and the stream of emails come in. And I think that, like, couple hours in the morning, especially when I can go to the gym and I can kind of think about, like, product and those things, that's, like, changed the trajectory of how I operate the company more than anything else. And I do it when I travel,

  2. 4:16 – 13:35

    #1 Thing Every Founder Needs to Do Everyday

    1. WW

      too.

    2. HS

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

    3. WW

      One of the ones I have that I think was a good habit in the beginning of the company is now... and now is starting to get bad, is I zero out Slack, like, every, like, 15 minutes, and so I'm in, like, almost every single Slack channel, and I read every single thing. And it was really good in the beginning of the company, because what you... If you do that constantly, you're basically, every day, all you have to do is catch up, compared to what happened yesterday. And so it's really easy to make decisions. The problem with that is I've probably done that for too long. As you scale, you actually have to focus more and more on what is the P0, right? And I think I've done a little bit too much of, like, still being in every single Slack channel and checking every little thing. There was, um, there was a time I was talking to someone from Sequoia, and they had been living with other founders, uh, during COVID. And they said that what they... And these are very, two very famous founders. I'm not gonna say who they are. But, um, they were saying that- he, he was basically saying that a lot of their routine was, they would just jump into random meetings at the company. And what they were doing is they were basically checking, just to see, like, how does this department do this sales call? How does this, you know, part of product create their PRDs and, like, analyze their PRDs? How does this part of the company come up with OKRs or, like, metrics, right? And I remember I left that dinner, and my co-founder and I were like: "Wow, those guys, like, aren't working. Like, that's, like, so lazy," and all this stuff, right? And now, when I think about those guys, I say, "Wow, they are incredible. Like, they're... I get why they're some of the best founders on Earth," because they've created a machine where they have so many folks at the company that are doing a really good job, that they spend the majority of their time actually moving the machine. And you go back to being, "I can focus entirely on product. I can focus entirely on what the most important things are at the company are." And, like, that's really what I'm trying to do this year, is transition from kind of all those heroics to, can you build a really well-run machine?

    4. HS

      I think the really interesting part, actually, is that Andrew Bilecki at Klaviyo-

    5. WW

      Yeah, yeah

    6. HS

      ... uh, he, he made the decision to kinda go back to product-

    7. WW

      Yeah

    8. HS

      ... as a public company CEO and bring someone else in.... Is that just testament of the times that we're in, the importance of speed and product centricity, do you think?

    9. WW

      A hundred percent, and I think, I think it's also a testament to something else, which is these companies are growing so much faster than they used to, and so you have to get the me- Like, it's very important to go through a couple stages, basically. Like, I see, like, stage one as product-market fit, right? Stage two is, like, company-market fit. In other words, like, have you created the structures of your company that are the same as traditional, you know, B2B SaaS or, or whatever, consumer SaaS, whatever you're doing, and what's different? And there are differences, and any VC who says that there are no differences, uh, at this point, hopefully, has changed their mind. There are differences, and it's different based off of what vertical and which company you're trying to build, right? And so you have your product-market fit, then you have company-market fit, and then do you know what you wanna go right back to? Reinventing product-market fit again, right? And so it feels like there's a cycle of doing that. Um, and I think for us, and, like, me personally, like, some of our first, like, couple years was product-market fit. Then it was comp-- last year was company-market fit. I'm back to product-market fit again, where it's like, what I spend a lot of my time on is, like, what is the direction of our company and our product, specifically for the next six months, year, et cetera, and now you can start thinking like that.

    10. HS

      You're at a hundred and ninety of ARR you posted yesterday-

    11. WW

      Yeah

    12. HS

      ... and you raised it eight billion. Do you ever, um-- Do you and Gabe sit and think, "Gosh, that's quite a lot. I'm worried about scaling into that"? Do you sit and think, "Gosh, we're undervalued?" How did you analyse that?

    13. WW

      Yeah. Yeah, yeah. Um, so we... It was, it was funny. This is, um, I think it was our offsite in twenty twenty-four, and I remember we kicked off twenty twenty-five, and the first thing I did is go up and I said, "Hey, we had a good year, but I'm pretty sure Anthropic's at, like, three billion in revenue right now," right? Um, my, my point is, the entire market is massive right now, and I don't mean just, like, legal AI market. Like, the AI market is exploding, right? And so I think you have to, when you are a leader of a company like this, one of the biggest jobs that you have is to make sure that your team doesn't feel like they've already won, right? Because the reality is the market pull is massive, and so sometimes your success isn't just your execution, it's the market pull, right? And so you have to benchmark yourself against other folks in the market, and not just legal AI companies, but actually just AI adoption, right? Um, I also think that we're just on an insanely compressed timeline, right? Like, I think the winners and losers are gonna be decided in the next couple of years, right, um, in a lot of these spaces. And so you really have to, at all times, make sure that the company doesn't go, "Wow, I did a really good job," chest bump, head pat, like, "We're done," right? You have to instil this: "Yeah, well, Anthropic, you know, ten X, and they started at X, Y, Z billions of revenue this year."

    14. HS

      Seven to fifty-five, and then fifty-five to one ninety, say, and then you're going one ninety to, uh... I'm a VC, so I can gasp, but, like, four hundred, four twenty, you're, like, two, two and a half X from that.

    15. WW

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

    16. HS

      Okay, so let's say five hundred, and then I'm looking at that and I'm like: Okay, then the eight billion doesn't feel too much.

    17. WW

      Mm.

    18. HS

      'Cause I... The way that we think about it internally is, like, what's end-of-year revenue?

    19. WW

      Yeah.

    20. HS

      And then what's the multiple on that end-of-year revenue? And if it's, like, twenty to twenty-five, feels fine.

    21. WW

      Feels more reasonable-

    22. HS

      Feels fine

    23. WW

      ... or closer, probably.

    24. HS

      If it's a hundred, [laughing]

    25. WW

      [laughing]

    26. HS

      it feels iffy. Then welcome to Series A land.

    27. WW

      Yeah.

    28. HS

      That's what happens in Series A.

    29. WW

      Yeah.

    30. HS

      It's why it's a bad place to be investing. Okay, but you never got to a stage where you're like, "Oof, this valuation feels like we're gonna live into it, or we've got to grow too much into it." Which round felt the most uncomfortably high? [chuckles]

  3. 13:35 – 15:26

    Why VCs Suck at Helping Companies Hire?

    1. HS

      they would do, and very few hit plan. Uh, so I totally get that. Do you actually believe that venture investors really move the needle?

    2. WW

      I think it really depends on who you get. I'll give you an e- an example of something that I haven't trusted VCs as much with-

    3. HS

      Right

    4. WW

      ... and I think I've been right in some instances, wrong in others, is hiring.

    5. HS

      Mm.

    6. WW

      So, um, the, the areas I've been wrong the most in is when to hire a more senior exec. The VCs have been right. Like, my partners are right. They're- they've been right. I took too long to hire senior execs in some instances, and it cost us problems. It created competitors when there shouldn't have been competitors, things like that, right? The thing that I think they've been wrong about is who to hire, and I think sometimes the problem that VCs have is they're managed up, right? Like, they don't actually see inside a lot of these businesses. They see the board meetings, right? And so sometimes the person who, like, presents really well at all the board meetings or something like that, they think of as, "That's a really good executive," right? And then that person gets a reputation for being a really good rep, rep... yeah, executive. I'm not from the tech world. I don't know any of these backgrounds, right? And so I'll sometimes get introed to someone from a VC, and they have, like, an incredible background. And I'll be like, "That person didn't seem very good," and it's just, like, my gut, right? Um, and I think I've been right in some of those instances, and I've bet on people that sometimes they said that I shouldn't have bet on, and they've turned out right. So when to hire execs, com- I've probably been wrong the majority of the time. Who to hire, I think I've actually been right a decent amount of times.

    7. HS

      I think, actually, it's a really smart distinction. I'm generally always wrong on who I suggest to my founders. [laughing]

    8. WW

      [laughing] Fair.

    9. HS

      And the benefit of hindsight, it's like-

    10. WW

      Yeah

    11. HS

      ... "Nah, that wasn't a good one." Often, we just bring in people that are actually too senior for the p- position, actually.

    12. WW

      That, that happens, too. Yeah.

    13. HS

      Which is a danger. [chuckles] Totally get

  4. 15:26 – 25:49

    How to Get Sequoia and a16z Term Sheets

    1. HS

      that. Dude, we, we kind of bonded over the king-making, where I-

    2. WW

      Oh, yeah, sure

    3. HS

      ... where I, you know, said, uh, some things about king-making, and you said, "That's not true." Why do you disagree with king-making as a theory?

    4. WW

      Yeah, I mean, and so I'll give you one example in our vertical. Um, the vast majority of our customers don't know who Sequoia, a16z, or any of those [chuckles] people even are, right? Um, and so [chuckles] I think that there's a l- you know, maybe there's a couple ways that people think about king-making. One, they think of king-making as it provides you with, like, more capital. More capital does not mean you run a better business. Like, if you, i- you could have as much capital in the world as you want, if you make the wrong product decisions, you're just gonna invest in all the wrong places, and it doesn't matter. It's the same as VC.

    5. HS

      Mm-hmm.

    6. WW

      You have 100 billion, and if you put it all into the wrong things, that still goes to zero, right?

    7. HS

      Mm-hmm.

    8. WW

      Um, so I don't think capital makes folks win. Um, the, the area where king-making or, like, people think king-making matters is customers, where they basically say, "Hey, this has, like, branded trust, and so that, that is good." I think there is, like, a little bit of legitimacy there, but it's not like only the top three VCs give you that brand.

    9. HS

      Sure.

    10. WW

      Right? A vast majority of VCs give you that brand, and what's actually interesting for us is, like, someone like EQT actually gives you that more than Silicon Valley because they're private equity, and, you know, a lot more lawyers know who that is, et cetera, right? Um, so I don't really believe in those two. The third one might be the one area that it is helpful, and that's just recruiting. Humans are very bad at judging how good other humans are. We're really bad at it. Like, we're really bad at it, and I c- I can tell you a, a very clear reason for why we're bad at it. We still pay so much attention to someone's resume. We care so much where they went to school, and this happens so much in technology. It happens a lot in tech. The other... The only other area where I know it happens an incredible amount is legal. Legal and tech are probably two of the main ones where prestige matters, where you went to school matters, how your grades were, who you worked under, things like that, right? I think it does help you in a sense of if you get one of those brands, people assume that there's maybe a higher chance of the company being successful. The reality is that might be the wrong person to hire in the first place [chuckles] because the people that think or go to a company because of the investors usually don't care that much about the mission of the company. And so my point with all of these things is, there might be, like, some short-term gains of, of perception mattering. In the long run, it doesn't matter at all. Because if you make all of the wrong decisions, nothing matters. It might help you with recruiting, though.

    11. HS

      To what extent does caring about the mission of the company really matter? I know that sounds a little bit cold and mercenary of me.

    12. WW

      Yeah.

    13. HS

      But if I'm a GTM leader and I'm a head of sales, and I'm a machine, and I'm here to get the number from five to 35 in the year-

    14. WW

      Yeah

    15. HS

      ... and I've done the playbook three times, I'm gonna fucking do it, and I'm gonna get my equity ramped.

    16. WW

      Yeah.

    17. HS

      Do you care?

    18. WW

      So I'll, I'll give you a, a good example of this. How many times a day do you think something goes wrong at Harvey?

    19. HS

      ... quite a few?

    20. WW

      Constantly, like twenty-four seven. How many times a day do you think we feel like there's, like, an existential threat, right? Or like, the big model providers are gonna release something, and maybe we haven't released something? All the time.

    21. HS

      Yeah.

    22. WW

      Like, startups are very difficult places to work, and so you think of, like, from the outside, "Oh, wow, they're, like, growing revenue so much. They're the category leader. They have all these investors," et cetera, et cetera, right? GRR is high, all these things, right? But internally, at all of these companies, it's chaos, and it goes up- morale goes up and down, right? You, you face really difficult things, and then you have to figure out how to get through them. And so being a missionary really does matter because the reality is, once you're on the inside, the brand of the company and the success of the company matters less than when you're on the outside. It matters a lot on the outside because people looking in are like, "Oh, my God, that's the most successful. It's super well-run," and all these things. Once you're inside, your day-to-day could be crazy, and you could be thinking you're not doing very well, right? So I actually think it matters a lot. People just don't realize that because they aren't inside of these companies. They're on the outside.

    23. HS

      You said about kind of existential threats.

    24. WW

      Yeah.

    25. HS

      What existential threat today concerns you most?

    26. WW

      Yeah, um, I think just moving fast enough on product. Like, that is, that is always, I think, the, the biggest existential threat for all the application layer companies. Um, and it's not necessarily that, you know, Anthropic or OpenAI are, you know, tomorrow, gonna put fifty percent of their resources after going the legal- after the legal vertical or tax vertical or anything like that. But they're just improving their product and models, and the value of your product is going to go down unless there is a massive delta between what your product does and what you could get from an enterprise GPT license-

    27. HS

      Uh-huh

    28. WW

      ... right? And so it's just a constant existential threat of: How do you make sure you get to, like, escape velocity on product, so you have enough of a product moat for them to not run you over? And I think about that daily. Like, when I'm thinking about competitors, my-- the main thing I think about is just I'm more bullish on these model- these labs than most people, I think. I mean, a lot of people are. Very bullish. They have incredible talent. Um, and I think more about, what are the frontier problems that our customers have that they're gonna solve later?

    29. HS

      4.5 changed the game for Anthropic-

    30. WW

      Yeah

  5. 25:49 – 38:21

    What No One Understands About Enterprise AI Adoption

    1. WW

      early days.

    2. HS

      What do you think that timeline is? I know it's a horrible-

    3. WW

      Yeah

    4. HS

      ... question to ask, but is it, like, a, a two- to three-year? Is it, like, a ten-year? You work with some of these enterprises. They don't speak the language that X-

    5. WW

      Yeah

    6. HS

      - and we generally do. What does that timeline actually look like?

    7. WW

      I think, like, three to five years, um, until we see, like, massive, massive productivity gains in enterprise. Um, I think the capabilities are there already. The capabilities were there two years ago, right? Um, a lot of this is like... i- if you think about just, like, the average enterprise workflow, right? There's, like, seventeen different systems they're pulling data from to get that workflow done. Like, literally, seventeen might be on the low end. Sometimes it's, like, fifty, right? And a tab-- you have a hundred tabs open, and you're opening in all these different apps, and they kinda connect to each other. They don't really connect to each other, right? And so the long tail on actually getting these systems and agents to do a task from start to finish is so difficult, and the problem that you're gonna end up happening is, you have these vertical companies building vertical agents, like us and Sierra, et cetera, but a lot of even the verticals connect to all of the other parts of the enterprise. So, like, one thing that's happening that's interesting for us is, [lips smack] you know, a lot of our revenue is starting to come from Global 2000 or Fortune 500 companies, and we actually haven't built many features for, like, tax compliance and procurement, right? Starting to happen is those departments are adopting Harvey, even though we haven't built features specifically for those departments. The reason why is the legal department actually interacts, and just, like, legal documents are such a core part of a business that they interact with all of these different parts of the business, right? And so we've re- released basically a feature that's multiplayer. It's called Shared Spaces. And at first, like, a lot of the impetus for doing it was, you want a co- large corporate, like a Walmart or whatever, to work with their law firms in the same platform, and that's happening. But actually, what's starting to happen is these corporates are using the... Like, legal team is working with the compliance department, is working with HR, is working with everything else, all in Harvey at the same time.

    8. HS

      I heard from Lagora that the Shared Spaces was ripped from them. [chuckles] Is that fair?

    9. WW

      No. [chuckles] We were working on multiplayer a long time ago. I think one of the, one of the things that's interesting about our company is we started with, like, the hardest customers, and we did the same thing actually on the in-house side, too. So, like, we had bank customers a while ago, right? And the security and permissioning systems that you need to build for a bank are so much more in-depth and, like, the enterprise readiness, than for a lot of the other folks. And the biggest problem with multiplayer and the way that we're doing it is, we're allowing the in-house side to kick it off or the law firm side. And to do that, the security and permissioning that you needed in place for both is astronomically high. So we were working on this, like, a very, very long time. We were working on it for, like, six months to almost a year. We just did all the permissioning and all of that stuff first before you do kind of the UI and on top.

    10. HS

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

    11. WW

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

    12. HS

      Do you respect them?

    13. WW

      Yeah.

    14. HS

      'Cause you guys hate each other in a way that, like... No, no, really, you do, and I, I, I love it because it's like, I feel we got too kind in tech.

    15. WW

      Mm.

    16. HS

      Like, "Oh, we're all friends." I was like: You know, we should be here to win. You know, Slootman?

    17. WW

      Yeah, yeah, it's very Slootman.

    18. HS

      Like, it's war?

    19. WW

      Yeah.

    20. HS

      We love him!

    21. WW

      Yeah.

    22. HS

      Uh, and you guys, really, you-- it's wonderful to see the animosity and hatred. [chuckles] But do you guys respect each other?

    23. WW

      Um, I, I think... I, I mean, I, I definitely respect them, and I think, like, one of the things that they did really well is, I think they did a great job in Europe. Um-

    24. HS

      Mm.

    25. WW

      - and, you know, this is back in 2023. We're, we're not that-- I think they're, like, six months after us or something. It, it's not that big of a gap. Um, and I think, like, one of the things that I would have done differently in the beginning is just invest, like, more in Europe in, like, 2023, right?

    26. HS

      Mm.

    27. WW

      And actually, we-- a lot of our first customers were in Europe, right? But having folks on the ground here is just really, really important, and respecting kind of, like, the different cultures and how to productionize that and all of those things, so...

    28. HS

      Why, why did you not out of interest in terms of coming to Europe earlier?

    29. WW

      It was just bandwidth. Um, I mean, we were... Like, when we signed Ano Sherman, which was our first customer, we had four people. So we did a four thousand-person enterprise-grade rollout with four people.

    30. HS

      Was this when you were-- I got told this from Pat, you were, like, in an Airbnb?

  6. 38:21 – 39:14

    AI's Impact on Professional Services

    1. WW

      them.

    2. HS

      Rory O'Driscoll, the Irish guy, uh, who I quote so often, he's brilliant, and should basically just replace me at this point- [laughing]

    3. WW

      [laughing]

    4. HS

      ... uh, he's much smarter than me. Uh, but he always says, like, "AI will be magnificent for us all if we see spend shift from technology budgets or fr- sorry, from human labor budgets to technology budgets."

    5. WW

      Correct.

    6. HS

      Will we see that shift here?

    7. WW

      Already seeing it happen.

    8. HS

      How does that happen?

    9. WW

      Yeah, so there are a couple companies that have basically said that the Harvey budget comes out of their spend on professional services, not out of their tech budget, and the, the budget for professional services is in the billions a year, versus the tech budget for that GNA group is astronomically smaller.

    10. HS

      Sorry, the professional services budget is not the junior talent that they have in their organization?

    11. WW

      No. No, and I think that's what's really interesting about our business, is

  7. 39:14 – 43:17

    Future of Law Firms: Do They Die?

    1. WW

      a lot of the work that we're doing for, like, a corporate is not the work that our law firm customers are doing. It's like alternative legal service providers. It's this, like, lower-end work.

    2. HS

      What percent of revenue is law firm versus external?

    3. WW

      Uh, right now... So, oh, so you mean corporate versus law firm?

    4. HS

      Yeah.

    5. WW

      Uh, I think it's around forty percent of our revenue is in-house, corporate, and sixty percent is law firm. Something like that.

    6. HS

      Wow! Sixty percent is law firm, forty percent's, like-

    7. WW

      In-house

    8. HS

      ... Fortune five hundred.

    9. WW

      Corporate. Yeah, yeah.

    10. HS

      Wow. Is that what you thought it would be?

    11. WW

      Um, I think, like, something like that. I mean, if you just look at the breakdown of, like, how many lawyers exist on Earth and how many of them are at companies versus-

    12. HS

      Yeah

    13. WW

      ... in-house, that's pretty much the same. So I don't see that changing.

    14. HS

      In five years' time, what will that be?

    15. WW

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

    16. HS

      Got you. How will we see law firms change?

    17. WW

      Yeah.

    18. HS

      Will we have a kind of cannibalisation of juniors?

    19. WW

      I, I don't think so. I think we'll just get more work. So i- th- interesting, I had a conversation with, um-

    20. HS

      Are you gonna make my girlfriend unemployed?

    21. WW

      [laughing] No. Um, I had a conversation, uh, with, like, a pretty large, like, private equity shop recently, and they were talking about, like, their year is gonna be incredible. Like, they think it's gonna be, like, a big M&A year, it's gonna be great. And they were talking about, like, how they think about legal fees, right? And the way that they thought about legal fees is, "The reality is, like, it's gonna be a big year, and whenever we have a big year, we pay more in legal fees. That's just, like, how it happens, right? But there are certain things I don't wanna pay for anymore, right? Like, there are certain parts of the deal, et cetera, that I just... marking up NDAs, whatever it is, I don't wanna pay for that anymore, right? But there's all these new things [chuckles] that I'm paying law firms for, like AI risk. [chuckles] Like, should you buy this company? Is there a, you know, a problem in XYZ country with, you know, an act or something like that that's gonna change it?" There are so many new pieces of work for professional services that my gut is, that's not what's gonna happen. In fact, I think what's gonna happen is the professional services market is going to actually keep growing at the same as GDP. Like, one way to think about this is, most professional services is cyclical. So if you have a really good year, professional services have a really good year. That's almost always how it works. Other than bankruptcy and, like, litigation is somewhat countercyclical, it, it depends on the, on the area. And so I think people think about this, and they're like, "Oh, wow! Like, AI is gonna impact legal, and it's gonna just destroy all these jobs." The thing they aren't thinking about is all of their customers are using AI to create more products. What happens when you create more products? You need more product [chuckles] to legal advice. What happens when, you know, you're expanding into other countries faster? What do you need? Regulatory advice, right? And so I think people are thinking about AI in all of these industries as, like, a vacuum, and the reality is, you should think about AI as, like, the entire economy, what's gonna happen, right? And probably what's gonna happen is the economy's gonna explode, these companies are gonna have crazy expectations for what they can do, and the professional service providers are gonna have to respond to that.

    22. HS

      Do you think the economy is gonna... So I can't believe I'm asking this question, 'cause it feels like the most base question that shit interviewers ask-

    23. WW

      [laughing]

    24. HS

      ... but maybe I'm just a shit interviewer at this stage, to be honest. Um, do you think the economy is gonna continue to explode? We have so much external concern outside-

    25. WW

      Yeah

    26. HS

      ... of the atmosphere-

    27. WW

      Yeah

    28. HS

      ... which says, like, "Hey, the circular deals are fucking nuts," you know? Um, "US borrowing has never been higher."

    29. WW

      Yeah, yeah.

    30. HS

      "Europe is a fucking museum that is completely unproductive." [chuckles]

  8. 43:17 – 48:54

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

    1. WW

      that.

    2. HS

      I do have to ask, you mentioned Europe, and we spoke a little bit about kind of Europe's productivity there. You said you wish you'd kind of-... been more proactive earlier on in Europe, but there's only so much you can do, but blah. What do you know now about building teams in Europe-

    3. WW

      Yeah

    4. HS

      - that you wish you'd known when you started?

    5. WW

      Oh, I, I think that it's similar in Europe to where it is in a lot of places, which is you don't wanna go into a country or a domain or anything like that and act like you know how to do something, right? Like, you really need to partner with an industry, or you need to partner with a geography, right? And so-- And when I say, you know, we should have invested more in that, it's more like we didn't invest in, in it that much in twenty twenty-three and twenty twenty-four. We invested tons last year, and we're investing even more this year, and the difference is pretty massive. Like, the, the difference in kind of the quality of our team of last year and the partnerships and things like that, and how our product is localized for each geo, is just a huge difference. But you can't do this from sitting in San Francisco and, like, kinda thinking about how to do it. You've gotta travel.

    6. HS

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

    7. WW

      I think that the, the biggest difference in... It's not a difference in talent, it just takes a long time to hire people, right? Uh, and so you have to just think about it for, like, with a way, way longer time horizon.

    8. HS

      Because of gardening leave.

    9. WW

      Yeah.

    10. HS

      Yeah.

    11. WW

      It's just, like, really hard to hire people. Um, and so that was just kind of, like, interesting to me or something that I wasn't used to. Whereas in the States, you can hire someone, and they, they start quite literally, like, the next day sometimes, right? Like, literally, or if they have to give two weeks' notice, they start exactly two weeks later, right? Um, and so that allows you to be a little bit more f- like, just I quickly need to hire this. Retroactively, I can fix a problem. In Europe, you have to plan out more, right? Um, and so we've done a, a lot of really big office openings, like we just, uh, announced Paris and Dublin and a bunch of other ones. Um, but you have to just think about this stuff at, like, a longer time horizon. You can't do it instantaneous.

    12. HS

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

    13. WW

      That's not what I've found, but I will say we interact-- I interact mostly with lawyers, and, like, lawyers have billable hour targets, right? Um, and at the end of the day, too, they are either at international firms or they're competing against international firms. So I have not found that at all, right? I mean, there are so many incredible, hardworking lawyers in Europe.

    14. HS

      UK lawyers work pretty hard.

    15. WW

      UK lawyers work insanely hard.

    16. HS

      Yeah, yeah.

    17. WW

      Um, and so it might be that I don't notice it as much because the domain that we're in, they work the same across the globe. Like, lawyers are just incredibly disciplined, hardworking people.

    18. HS

      In terms of the people assessment, Pat told me that you're world-class at understanding people. If I were to ask you for a trait that you look for in someone joining Harvey that is less obvious than the foundational integrity or, like, ambition-

    19. WW

      Yeah

    20. HS

      ... or bullshit that you normally get. Like, I look for obsessed psychopaths. [chuckles]

    21. WW

      Mm-hmm. [chuckles] That's a good one. You definitely need to be obsessed.

    22. HS

      Yeah. What would yours be?

    23. WW

      So I... So obsession is definitely very important, but the one that I look for right now a lot is ownership. It's really, really important. Um, and there's a bunch of different ways that you can assess this, but you do, over time, you start to be able to just read if someone actually can take ownership over something or not. Um, and the, the reason this becomes really important is, as you scale as a problem or as a, as a company, it becomes really hard to figure out where a problem is stemming from. It becomes hard because what... Th- this is how this ends up going, is it used to be I knew every single thing that was going on at a company, and I can just be like: "Hey, that's where the problem is. I'm gonna unblock that," right? Now, we're getting to the point where I know most of what's going on at the company, but sometimes something is, like, so low down that I don't know what the problem is. And if I ask five people, they'll all do this. [chuckles] It's like the Spider-Man meme, right?

    24. HS

      [chuckles] Yeah, I love it.

    25. WW

      Um, and what I have found is-

    26. HS

      That's like, that's like bad deals in venture firms. "Who did the deal?"

    27. WW

      Yeah, and it's just, "Uh..."

    28. HS

      [laughing]

    29. WW

      It's like all over the place. Yeah, exactly, right?

    30. HS

      It was Johnny who left.

  9. 48:54 – 55:55

    I Have Massive Trust Issues…

    1. WW

      And-

    2. HS

      Where, where, where do you think that comes from? I, I, I have trust issues 'cause I've found that, generally, when relationships break down, it always comes down to them extorting me for money.

    3. WW

      [chuckles] Great.

    4. HS

      It's true.

    5. WW

      Yeah. I think my trust issues... I mean, I think part, you know, part stuff is it's hard to tell whether it's, like, nature or nurture, right? Um, but I, I think that I definitely had some problems with authority when I was younger. Uh, and I had a, um, not the normal Silicon Valley kind of background and upbringing. Um, and because of that, I think that I had to-- I really went out on my own at, like, a pretty young age and was pretty independent. Um, and I think that one thing that you have to learn when you're leading a company, um, is you are a leader, and you are a partner to the rest of your team. It is not just you. Like, I am not Harvey.... like Harvey is not me. Like, it is a group of people that are building this company, right? And I think that sometimes what founders can end up doing is they can start basically saying, like, "I want to be the number one-" I think of this as like a sports team. There are people I know that they don't care about winning the championship, they wanna be the person who scored the most points. And they're okay with losing the championship, as long as they're the one that scores the most points. Those are the exact type of people that I do not wanna work with. I wanna work with people that do care about how many points they've scored, but they care about that because they w- they helped win the game, right? And I think that's a huge problem in tech, is we- you have too many people that it's me, me, me, me, me, and not company, company, company. So-

    6. HS

      God, I think, I think the US is just full of logo chasers. [chuckles]

    7. WW

      There's a lot of that, yeah.

    8. HS

      You guys just love to, like, work at a hot company. It's the hot company bouncer, I call it, where it's like they just go two year, two year, two year, two year, and it's like they're doing venture portfolios with, like, company equity.

    9. WW

      Yeah.

    10. HS

      And, and it's just like, God!

    11. WW

      I was about to say VCs do the same thing.

    12. HS

      And I sit in these operator groups, and they're like, "Ooh, I hear Clay's really hot," or, "Ooh, I hear, like, Notion's really hot."

    13. WW

      Yeah, yeah.

    14. HS

      And they just jump.

    15. WW

      Yeah. I mean, I think the VC-

    16. HS

      The promiscuity of American operators is incredible.

    17. WW

      Is, is the same thing. But, but, but, like, look at-

    18. HS

      Brits are too negative. We're like, "That's crap." [laughing]

    19. WW

      That's... [laughing]

    20. HS

      "Don't be a dick."

    21. WW

      Yeah. I mean, I, I think, like... This also- I, I forgot who tweeted this. I don't re- I don't remember w- who it was, but this was, like, early 2022, um, and, like, it was... Or, sorry, end of 2022, and it was, like, right after the ChatGPT launch. And someone, I forget which VC did this, so sorry for not giving credit to them, but they basically tweeted, "My prediction is what's gonna happen is a lot of VCs, because they don't understand the AI ecosystem, they're gonna revert back to looking at resumes, because they don't understand." And this is what people do. When there's situations of chaos and folks don't know what's going on, the safest thing is to go look at other social signals to make decisions, instead of using your own gut. And so I think that that's happening a lot in AI, and hopefully, you know, as the markets, you know, mature, this stops happening. But there's a lot of, "I don't really understand this, and so what I'm gonna do is look at the resume or look at a logo or look at that, because that seems like a safe bet."

    22. HS

      How many truly great researchers do you think there are?

    23. WW

      Hundreds, and that's it.

    24. HS

      How do you know a good researcher from a resume?

    25. WW

      I, I don't think you can. That, that I think is actually a, a pretty big disconnect. The researcher community knows. So, like, this is a huge disconnect between VCs, I think, and the researcher community.

    26. HS

      So what would you [chuckles] advise me investing?

    27. WW

      What I would do is you can use the researchers to pinpoint who is the best researcher. So in other words, if you ask a bunch of the researchers, not other VCs, ask a bunch of the researchers, who do they respect the most? They have such a tight-knit community, and it's all merit-based. Like, I'll tell you a group of people who do not manage up: AI researchers. That is not what they do at all, for better or for worse. [chuckles] Um, and because of that, if you, if you ask that community, "Who are the best folks?" They will triangulate for you, and they will help you find. And usually it's not the loudest. They aren't necessarily the most famous, et cetera. Like, it, it, it's not like that.

    28. HS

      How do you assess the promiscuity of AI researchers?

    29. WW

      Yeah.

    30. HS

      I mean, like, you know, poor old thinking machines, you know, uh, home alone as M- Mira Murati now. Um, how do you assess that? Is that just a sign of the very brilliant times?

  10. 55:55 – 1:01:30

    Biggest Lessons on Effective Deal-Making

    1. WW

      work.

    2. HS

      We, we said about the skill of people assessment in terms of the talent there. We said about your lack of trust and trust issues, which was another one-

    3. WW

      [laughing]

    4. HS

      - that I think it was Pat told me. I put one of your investors, but I'm gonna throw him under the bus. I think it was Pat.

    5. WW

      Perfect. Great.

    6. HS

      Yeah, yeah. Sorry, Pat.

    7. WW

      [chuckles]

    8. HS

      Um, Pat did also say that you're an excellent deal guy.

    9. WW

      Mm.

    10. HS

      And I wanted to unpack that. What was your biggest advice on how to get the best deal-

    11. WW

      Yeah

    12. HS

      ... in deal-making?

    13. WW

      Um, maybe two pieces of advice. One is listen more than you speak, and it's very, very dumb, but it's true. Um, I think a lot of people in deals they think that movement is action. So they think that, like, movement is progressing the deal forward, and they think that if they talk the most, they're in control of the deal. Not true, right? In the same way that in conversations, just because someone isn't participating in that conversation doesn't mean that they aren't listening. It doesn't mean that they have maybe the upper hand or something like that, right? And so I think listening is really important, and I see a lot of folks think of deal-making as like chest forward, and if I'm the loudest and I'm saying the most... The reality is, like, all deal-making is just people reading. That's it. And it's people reading at scale. So it's people reading, like, a one-on-one conversation, and then it's reading groups of people, and then it's reading, you know, entire verticals of people, et cetera, and it's figuring out what they want. The second piece is know when to not negotiate. This, I think, is actually really, really important, and the best deal-makers I know are very good at this, which is there are certain deals where you want one thing from the deal, and nothing else matters. This only works when you understand the value of something more than everyone else does, right? And if you understand the value of something more than everyone else does, throw all your-- all of your principle deal-making, and you're supposed to negotiate X and then Y, and then it'll be fifty percent in between and all of that, that's all bullshit. Throw that aside, and get the thing that you know is more valuable than anybody else does done. And I know a lot of people that... The best deal-makers I know, like, the best, they do-- they know that very well.

    14. HS

      When did you understand the value more than everyone else, and how did that shape how you behaved?

    15. WW

      There's just certain deals that we've struck where I wanted one thing in the deal, and maybe the financial part of the deal or something else about the deal, like my CFO or my VCs, were like: "Oh, my God, don't agree to that. Like, do X, Y, Z." And I knew that if we signed it, and we got the particular thing that I wanted from that deal, it would help our company to such a degree that it would help close another deal or it'd help do something else. Like, a lot of what you're doing, I think, like the very good deal-makers, and I think Sam Altman is incredible at this, is you're holding multiple ropes. And you can kind of think of it as like you have, like, seventeen ropes in this hand, you have seventeen ropes in this hand, you're grabbing all these ropes, and at some point you're gonna get, like, pulled apart 'cause it's just too much pressure, and you're gonna lose, right? And what you do is you get good at tying off one of the ropes, and then that pressure's gone, and you have one tied. And then you tie another one, and then you tie another one, and you tie another one. And tying those ropes allows you to pull more ropes, right? And, like, that's a lot of how I think about deal-making. Um, I think another company that has done an incredible job of this is Microsoft. Incredible job. Of they've created this partnership ecosystem, right? And a lot of people have given them a lot of flack of like: "Why do you let people do X, Y, Z partnership? Why do you let people build on this? Like, they're just gonna take it." And it's very clear that Microsoft has actually won in a lot of areas because they've decided to partner with kind of everyone instead of saying, "Ah, no, brass tacks, we're gonna, you know, be very tough on this."

    16. HS

      I think one actually also is, always when you hire people, and, you know, they say that they want seventy-five grand.

    17. WW

      Oh.

    18. HS

      And then so often I meet founders, and they're like: "Ha! But I got them down to seventy." And I'm like: "Give them seventy-five."

    19. WW

      Give them seventy-

    20. HS

      They won. They start, they feel valued.

    21. WW

      With hiring, this is a, a sup- a huge mistake that people make, massive mistake. If you wanna hire somebody, hire them whatever they want to be hired, and put them in the position that they want. If they're best in class-- If you can't tell if they're best in class, it's a separate problem, but don't go back and forth. Doesn't matter.

    22. HS

      One of the most valuable bits of advice Josh Kushner actually gave me, I love him, is he said, "If you're..." And this was on a specific in, like, investments. "If you're willing to take less, don't do the deal."

    23. WW

      Yeah.

    24. HS

      Imagine I'm a VC, and it's like I want ten percent. You're like: "I can only give you seven." I'm like: "I'm actually fine with seven."

    25. WW

      Well, then you don't believe-

    26. HS

      Don't do the deal

    27. WW

      ... in that company.

    28. HS

      Hundred-

    29. WW

      That's not gonna be a legendary, category-defining company.

    30. HS

      A hundred percent.

  11. 1:01:30 – 1:05:10

    Cold Emailing OpenAI and It Leading to a Term Sheet

    1. HS

      You mentioned, um, OpenAI and Sam as the deal-maker as well with this different-

    2. WW

      Very good

    3. HS

      ... I liked it. [chuckles] Um, I heard that you cold-called Sam-

    4. WW

      [chuckles]

    5. HS

      - uh, in the summer of twenty twenty-two. Can you just tell me about that before we do a quick fire?

    6. WW

      Yeah. So it wasn't a cold call. We, we cold emailed them, um, and we cold emailed Sam and Jason Kwon. Um, what we had basically done was we go- went on r/LegalAdvice, which is basically like a subreddit for asking legal questions, and we grabbed a bunch of those questions, ran a chain of thought-... product that we had basically built on top of it, and gave it to a bunch of landlord tenant attorneys. And then we basically said, just, like, "Look at these questions, and tell me if they're- you would send the answer," we didn't say anything about AI, "to the consumer who asked the question." And of 86 out of 100 questions, three out of three said, "This is a perfect answer. I'm done." And we cobbled all that together, and we just sent a cold email to Sam Altman and Jason Kwon. Um, the idea was basically, "Hey, did you guys know that..." You know, at this point, it was GPT-3, and just the API was public. I think the end of 2021 or beginning of 2022, they had an API. Um, "Did you know it was this good at legal?" That was it. That was basically the subject line of the email, was like, "Did you know it was this good at legal?" Um, and we met them, like, pretty recently after that.

    7. HS

      How did that go?

    8. WW

      Uh, it went well. Uh, we had a call with Jason first, and just kinda talked about, like, what is our strategy as a company, um, and what would we build? And then we had a final pitch to kind of the rest of the OpenAI C-suite, actually, the morning of July 4th, uh, 2022. Yeah, it was, like, 11:00 AM on July 4th, uh, and we did a pitch to the rest of the company.

    9. HS

      Do you get nervous before these? Like, when you go into a Sequoia-

    10. WW

      Yeah

    11. HS

      ... and you pitch the partnership. Fuck, that's nerve-wracking.

    12. WW

      So, yes, I had a weird thing where, like, I didn't know who any of these guys were. Um, and so, like, when we were doing our series... So we-

    13. HS

      It's so funny, 'cause, like, you don't know, and, like, for me, as a venture nerd, I'm like, "Holy shit!"

    14. WW

      Yeah, you're like super scared.

    15. HS

      Like, I know everything about every one of them.

    16. WW

      But, like, I mean, like, now I do, but back then, I didn't know anything. Like, so... I mean, I didn't even have friends in tech. Um, and so when we did- we did our seed, and we didn't go to anybody else. It was just OpenAI. And then for our Series A, we did like-

    17. HS

      God, how much did they invest, and for how much?

    18. WW

      The actual terms... I don't remember what the post actually was, but the pre-investment was, like... It was, like, 4 million or something like that. Um, and anyway, what happened at this, the Series A, was we went and met with basically, like, I think it was, like, 10 VCs or something like that in, like, 48 hours, right? And I quite literally did not know who the VCs were. Like, I didn't know. Like, my co-founder was from tech, and he, like, knew, and he basically gave me advice and things like that. So I actually think I had, like, a p- weirdly unique view of the VCs because my entire judgment of them was just how, like, how that first meeting went. Like, I didn't know that, like, this Sequoia was in this tier, and this one was in this tier, and, you know, whatever. I didn't know any of that.

    19. HS

      You did-

    20. WW

      I didn't even know who they were

    21. HS

      ... 10 VC meetings.

    22. WW

      Yeah.

    23. HS

      How many term sheets did you get?

    24. WW

      Um, for that? I, I don't remember. It was, I think, like, half or something like that, yeah.

    25. HS

      Which was the worst?

    26. WW

      The worst term sheet or the worst meeting?

    27. HS

      Worst meeting.

    28. WW

      Oh, I'm not gonna say that publicly. [chuckles]

    29. HS

      It's worth a go.

    30. WW

      There was one. Oh, there was one, um-

  12. 1:05:10 – 1:13:13

    Quick Fire Round

    1. HS

      amazing. Uh, listen, I wanna move into a quick fire round.

    2. WW

      Yeah.

    3. HS

      Um, what have you changed your mind on in the last 12 months?

    4. WW

      Um, yeah, how much... So I said earlier that a lot of company-building has changed. I actually think a lot of it remains the same. [chuckles] Uh, and so there's a lot of kind of just, like, core first principles of scaling a company that I am much more focused on that I wasn't focused on in the beginning. I'll give you the dumbest example ever. For the first, like, two years of the company, when I was doing, like, revenue projections, I never... And this is embarrassing, really embarrassing. I never was like, "Huh, if I wanna hit this amount of net new ARR, you need to hire this many AEs at this quota, and this is how long it takes to ramp them, so you need to have hired them at this point before you do that." I'm dead serious. Like, I never even thought about that, right? And it's these really core, like, laws of physics about companies that remains the same. Like, there's no different in AI. Um, and I think, like, in the past, maybe t- what have I learned in the past 12 months? Maybe it's more, what have I learned in the past, like, 18, like, the, the second half of the company, basically, is how much of a lot of the company building is actually the same. Uh, and I probably should have listened to people a little bit more about that.

    5. HS

      You have Sequoia and Andreessen on the cap table.

    6. WW

      Yeah.

    7. HS

      How are they different to work with? I'm not asking, like, for better or worse, but how do you... How are they different to work with?

    8. WW

      Yeah. I think that there's obviously, like, a difference in scale, right? Like, a16z is just, like, a lot, a lot bigger. I would say that a16z is l- just also, like, louder, right? Um, and so they're a little bit more in, like, these other regions and other areas and things like that. Um, whereas Sequoia is, you know... I- it's just a different style, right? It's closer to... There aren't as many partners and, and things like that.

    9. HS

      Were you nervous pitching to Marc and Ben?

    10. WW

      Um, uh-

    11. HS

      You knew them coming in.

    12. WW

      Yeah, definitely.

    13. HS

      Yeah.

    14. WW

      Yeah, definitely. I mean, I, I'm, I'm always nervous, and I, I think, like, one thing, too, I, I think I said this earlier, but, um, I think Keith Rabois says this, who I've actually never met in person.

    15. HS

      Wow.

    16. WW

      Um, there's a, there's a, a, a couple people... I have a list, actually, at the top of, like, my doc. I have, like, an operating doc, and I have a list of people, and they all have, like, two words next to them, and it's, like, the thing that I've, like, learned from them or something like that. Um, and, uh, I've never actually met Keith Rabois. I think he's an investor in one of our kind of, like, slight, kind of competitors.

    17. HS

      He's in Spellbook.

    18. WW

      Yeah, yeah, yeah.

    19. HS

      Yeah.

    20. WW

      We, we don't compete with them tons, but in some degrees, we do. Um, but anyway, o- one of the things I think he was talking about, uh, uh, at some point, is, like, how important it is that you should be constantly stressed, like, constantly stressed, and do things that make you stressed every day. Um, I strongly agree with that, like, really agree with that. Like, I think the times that I've stagn- or the company has stagnated, is-... every day I don't have something that's, like, really stressful. Like, the weeks that I do the best work or feel like I did the best work, is every single, like, night before I go to bed, I'm like, "Ah, shit!" [chuckles] Like, I have- like, tomorrow is gonna be... Like, there's so many things. Everything needs to go right. I'm really stressed. It's compounding, like massively compounding for you as an individual, to just put yourself through that stress.

    21. HS

      I freaking love it. Uh, Pat r- like, tweeted, like, "Hey, if you are, like, ambitious and you wanna learn about working in AI applications, there's no better place to work than Harvey." Keith Rabois? Hmm. [laughing]

    22. WW

      [laughing] Oh, somebody said that. But, but, but, but Pat has this-

    23. HS

      My point is, though, dude, I love the way, like, you didn't see that, but, like, all VCs are just like-

    24. WW

      I didn't see that

    25. HS

      ... "Oh!" [chuckles]

    26. WW

      Yeah, yeah. I mean, but, but it's interesting. Like, I think Pat also has this, too, and, and all of my VCs do, and, and Pat in particular, he really thinks of, like, just constant... Like, a "relentless application of force," is what he says, and that's actually what I have next to his name. Um, and i- that's incredibly important, and I think that if you lose that as a company, the company's pretty much over, right? Um, I think that you're- you as a founder need to constantly, constantly be a- applying force, and it starts with applying force to yourself. And if you aren't applying force to yourself, you don't have that ownership mentality, and you'll start to get weak-

    27. HS

      I- who-

    28. WW

      ... and I think that will trickle down to the rest of the company.

    29. HS

      Who... A couple of other people on that list, and what they- what do you have next to them?

    30. WW

      [laughing] I have Brian Halligan's on there, uh, and his is "No." It's just the word, "No." And one of the things... He's been incredibly influential and, and helpful to me, and one of the things I had a problem with is just, like, saying no to things. Um, and it's a huge, huge problem as you scale as a founder, of figuring out an ability to actually block off time for yourself and to say, "No, this is my priority. I'm saying no to everything else," right? Um, and it's the same with, uh... This is also probably one of the main things that hopefully I've improved on product, is I used to every quarter just be like, "And there's a P0, and then also there's a P00, um, and then there's this, and this, and this," right? And I've started to be a lot more disciplined and try to be disciplined with my team of, like, every time that we do product planning, something should hurt. It should feel like a breakup. [chuckles] Like, you are- you have to... There's has to be a couple really good ideas that you say no to, and it's the same as across the entire company. And Brian Halligan has been really helpful with kind of teaching me how to do that for myself, and how to do it with the rest of the company.

Episode duration: 1:13:23

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