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

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

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

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.

Were you nervous pitching to Mark and Ben?

Um-

You knew them coming in.

Yeah, definitely.

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.

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.

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

[laughing]

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?

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.