Chapter 1: What is 'The List' that powers Winston's $11B business?
the next, you know, year or two years are basically going to define the companies that are successful for the next decade, probably, right? If not more.
Chapter 2: How can CEOs effectively say 'no' to distractions?
I want to double click on this massive 200 page, 400 page Google document that you have. How would you describe that to somebody and how do you use it?
So basically, I mean, I can break down the whole document. So at the top, it basically has like the couple things that I want to remember, right? You know, kind of like motivational things.
Chapter 3: What are the three principles for strong decision-making?
some of the ones that i care about the most are prioritization like this is something i think people have a really hard time with is every you know like three to six months you have to completely redo how you do prioritization as a leader i think um and if you don't you're really going to start messing things up and then it has the top three documents that i care about tracking
Chapter 4: How is Harvey changing the legal world with AI?
um and so you know if i'm concerned about a certain part of the org then it will have you know like a revenue tracker if i'm super concerned about like uh post sales or we need to do much better like customer service on the back things like that it'll have a document there that has like a bunch of stats on that right and then under that it'll have what are the three goals for the quarter and almost always it's usually like one higher
uh like one product feature i mean we ship now we're getting to the point we're shipping like four new products every quarter um which is awesome but you know the one i care about the most or i need to focus on the most and then like one major area of the company i need to fix and then after that it will have my daily list and i think the the thing that's good about it like all the company dashboard stuff and motivation like i think everyone has their version of that
The thing that I think is actually good is every day I rank everything I need to do.
Chapter 5: What lesson did Winston learn from a cold email to Sam Altman?
And so it's daily and then I refresh it and then I cross them out. And the re-ranking is I think really important because what I've found is the more times I click into that doc that's called the list and I re-rank something, the more I think about what I'm doing, like meta thought about my thoughts. And that is really good. That's when I'm prioritizing the best by far.
That's when my schedule looks the best. That's when I'm performing the best is how many times do I click in that doc during the day? Because it will make me reorg something, put something in first place in bold and ignore everything else. So it's more of a prioritization like document. What do you say no to? Most things.
Chapter 6: How can leaders build resilience to failure?
And I think an increasing amount of things as the company goes on. I used to say no to almost nothing.
What's your inner monologue when you're sort of looking at something and you're trying to decide, does this make my list? Yeah. Or do you capture it or do you just let it go? Like, what is that?
When I get really bad at it, I ask my chief of staff to force me to write a paragraph about why I'm going to take a meeting. Full paragraph about why I should take a meeting. And it's so easy if you do it that way, because for 99% of meetings or events or whatever, you start writing the first sentence and you're like, I don't want to do this.
And if you don't want to do this and you're like, this is a waste of time, probably the meeting or the event is also a waste of time. For the things that I think are really important, when I'm like, I got to write that paragraph, I could write 20 pages, right? And it's easy. It's really easy. Yeah.
And so, again, I think this goes back to like, how much of your week and your day are you thinking about what you're doing? Seriously, like, what is the goal of the company right now? Like, what is the main bottleneck? What is the main problem?
And I think like a good founder, and I'm not saying I am anywhere close to one yet, but the ones that I've seen, it seems like what they're really good at is two things. One is they've built a machine.
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Chapter 7: What advice does Winston have for law students?
And so because they've built a machine, they have time to only focus on what is the main bottleneck with the machine, right? And so those are two different skill sets, I think. And you have to have both, right? Because if all you're doing is like bottlenecks before you've built a machine, it's like,
Chapter 8: How will AI impact the future of law firms?
You're never going to hire the right staff. You're never going to get the processes right. You're never going to build the right product. And so you have to be constantly, how am I building out the machine? And then once that machine is somewhat built out, I think the number one goal is just how do you improve that machine constantly? And you kind of have to think about your company that way.
And I think that that's hard because that means you are going to be in pain 24-7. Because if something's going well at the company, you are not going to be working on it.
like if there is a part of the company that is running super well and there are no bottlenecks i ignore it entirely like absolutely entirely and i try to only focus on the things that are like burning um and i try to focus on like the number one thing that's burning i want to come back to meetings for a second i want to tie this to psychology maybe and maybe not you can tell me i'm wrong
But when you're saying no to somebody, why is it we have a problem saying no to people? You don't want to take this meeting. This paragraph, you're stressing. You're like, oh, this doesn't make sense. Is that because we want to be liked?
The reason I think people have a really hard time saying no is... They say yes to a lot of things that make them look good in the short term, instead of being able to take the pain of ignoring it and then doing so well because you ignored it, the people back off. So let me give you an example of this.
If a third party or like an investor or someone like that says, it's really important for you to hire a certain person right now, right? what you might end up doing is you take a bunch of meetings with that C-suite, right? And you take tons of those meetings because the investor says, you know, you're having revenue problems, right?
And the reason you're having revenue problems, it must be because you don't have a certain C-suite, right? But deep down, you're like, the reason we have a revenue problem is because there's a problem with product. It has nothing to do with like anything that's going on here, right? It's not because we haven't hired a chief revenue officer yet. It's because the product isn't good enough.
But that has a delay. And so what people want to do is they want to start making improvements so that third party can see it immediately. So they'll start doing the meetings because every time you do that meeting, you get a pat on the back from your VC or someone that says, good job, you did that meeting, you're progressing.
the alternative is you ignore everyone and everyone thinks it's getting worse and worse and worse and worse and worse and you go fix the issue that's actually an issue and then in two quarters or six months all of a sudden the company's doing really well and that's just so hard to do like that is you face so much pressure as a founder that it's really hard to do until you've kind of proven yourself and
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