Winston Weinberg: Speed, Stress, and Better Decisions  🔗 **Source:** [Winston Weinberg: Speed, Stress, and Better Decisions](https://share.snipd.com/episode/7fcc3970-82ff-4905-80c1-96770c46f270) ## Highlights - **Daily Re-Rank Your One Prioritization Doc** - Use a single living Google Doc called The List to force daily re-ranking and ruthless prioritization. - Winston ranks tasks every day, bolds the top item, and clicks in the doc multiple times to trigger meta-thought and focus on the P0. Transcript: Winston Weinberg 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. 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. 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. 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 post sales or we need to do much better, like customer service on the back of 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 where shipping like four new products every quarter, 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 thing that's good about it, like all of 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. 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. ([Time 0:00:20](https://share.snipd.com/snip/00c1b020-66c6-4ce2-886d-225f193f04fc)) - **Require A Written Justification Before Meetings** - Force yourself to write a full paragraph explaining why you'll take a meeting before accepting it. - Winston says 99% of meetings evaporate on the first sentence and the important ones expand into many pages when truly necessary. Transcript: Winston Weinberg At it, I ask my chief of staff to force me to write a paragraph about why I'm gonna 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? ([Time 0:02:39](https://share.snipd.com/snip/cfed2e56-5bd9-4079-8717-bf8314fb72da)) - **Two Way Door Mentality To Speed Decisions** - Treat decisions as one-way or two-way doors and assume most are two-way doors to move fast. - If a choice is irrelevant to your P0, do something and iterate; if it distracts from P0, say no immediately. Transcript: Winston Weinberg Determine if something's a one way or two way door immediately. Like that's the first thing right um with the idea that baseline 99.9 of things is a two-way door the second thing is what is go back to what is your number one priority right now like what Is your p0 right um and based off of what your p0 is does this help the p0 does this hurt the P0? Or is this irrelevant to the P0? Why that's important is if it's irrelevant to the P0, it doesn't matter that much what decision you make. And so just do something and go. If it's negative to the P0, as in it like takes distraction away from the P0, the decision is no. Full stop. And then three is be realistic about who is going to be doing it. ([Time 0:07:31](https://share.snipd.com/snip/dc4c5cb6-4b9f-4b52-86f1-a172c22a4521)) - **Reddit Experiment That Triggered Harvey** - Winston tested GPT-3 on 100 landlord-tenant Reddit questions and had three attorneys vet outputs. - On 86 of 100 questions all three lawyers said they'd send the answer with zero edits, which sparked Harvey's founding. Transcript: Winston Weinberg And the end is almost always like, can I sue somebody? And we grabbed a bunch of landlord tenant questions in California, and we ran this chain of thought prompt over them. And we basically gave it to three landlord tenant lawyers. And we said, somebody asked this question. We said nothing about AI, just somebody asked this question and here's the answer from a lawyer, right? Would you send this? Like if you were the lawyer here, would you send this with zero edits? On 86 out of 100 of those questions, three out of three attorneys said yes. ([Time 0:10:59](https://share.snipd.com/snip/95b1ce2c-fdf6-41e3-b861-b47981a44e60)) - **Cold Email To Sam Altman That Raised Funding** - Winston cold-emailed Sam Altman and OpenAI's general counsel with results and chain-of-thought prompts. - They met the leadership on July 4th and raised funding directly from OpenAI-linked investors. Transcript: Winston Weinberg I think he's the chief strategy officer now. And we emailed them the results. And we basically said, I mean, the body of the email was basically, did you know that the models were this good at legal? And we emailed them that. They got back to us pretty fast. We met with Jason first and just kind of went through what we did in the process with Reddit. We showed them our chain of thought prompts and things like that. And then we met with the rest of the leadership team on actually the 4th of July. And we pitched them our idea for the company. And we raised money after that. Shane Parrish And they were your original investor? Winston Weinberg Yeah. We didn't go to any other VCs or anything like that. ([Time 0:12:05](https://share.snipd.com/snip/359b4cf0-97cc-413f-af0e-ea2b87151d0c)) - **Demo With The Lawyer's Own Brief** - Personalize demos to lawyers using their own recent briefs to get attention and show value. - Winston analyzed filed briefs, had Harvey argue against them live, and sometimes risked hallucinations but captured lawyers' attention when it worked. Transcript: Winston Weinberg Product. The hardest thing to do in the beginning was actually get lawyers attention. And so what I would do is I started, I was a litigator, so I'd started with litigation examples. And there was a nice advantage where a lot of what you file, if you're in federal court, it has to be published online, right? And so I could go and I could find the last thing, like argument that they made, and I could actually find the document where they made that argument. What I would do is I'd grab that and I'd say, what's good about this argument? Could you argue against it? Like, how would you, how would you poke holes in this, you know, this contention, things like that. And you'd go from the lawyer, like I used to have demos in the beginning where lawyers would literally be on their phone. I would show them. I mean, at the time I thought it was AGI itself. Um, and I'd show them this and they would just like look at their phone and not pay any attention. And when I started saying, Hey, you filed a brief last week and, you know, Apple V, whatever case, and you want to see how Harvey would analyze that brief and argue against you. I mean, they were completely, you know, it's like that meme where the guys with his video games like this, and then all of a sudden, yeah, it's like that. And they would just watch the screen and read every single word that came out of harvey uh super risky because you know a decent amount of time it would hallucinate and get something wrong And if it hallucinated the lawyer was like okay this is useless like get me off this demo but when it worked it worked super well the riskiest version of this is we did it during our series A pitch to Sequoia, where Sequoia grabbed a bunch of lawyers that they knew and they had us demo to them. And I just remember Pat Grady emailed me afterwards and was like, is that what you normally do? Because it got them really riled up. And, you know, it ended up working where we picked a use case, it worked, but we found like a argument that they had done. And I showed basically like analyzing that brief, and it was a good analysis. ([Time 0:13:02](https://share.snipd.com/snip/4213cd19-40c1-424e-8195-8f3285c7bd32)) - **Deal That Almost Collapsed The Company** - Winston signed a deal to buy a company before securing full funding and later pulled out to avoid risky PI K debt. - The collapse forced Harvey to actually build product, hire properly, and made the team more resilient. Transcript: Winston Weinberg And so we got the term sheet. We like locked them up for a certain amount of time, And then we went to go get the money. And of the money, we were short. We got like a lot of it. We were trying to raise like around like 700 million or something like that. And we got, I think like 500 in clean equity. And then the deadline was there. And we had an option. We could have taken like a loan basically with like PIC. The problem with those is if you take that debt, if you don't fulfill the debt obligation, somebody else can own the company. So it's not in dollars, it's actually in percentage points of the company. It's called payment in kind. And we decided not to do that. And when that happened, and I remember just pulling it off and telling the other side we weren't going to do it and everything like that, I thought the company was over. ([Time 0:20:34](https://share.snipd.com/snip/3b2b17ae-9126-42a2-9d8f-7d9b3f999159)) - **Stress Maxing To Build Resilience** - Maximize stress exposures early to build tolerance and reduce future damage. - Winston recommends doing painful tasks (like firings) at small scale early so you learn the process and lower future risk when the company grows. Transcript: Shane Parrish Because when I listened to you talk about stress before this, I almost think of like stress maxing in your head, like you're actually intentionally seeking out stress. Winston Weinberg Well, I mean, you want to maximize it before it does too much damage to you, right? So if there are 10 things that you're really stressed about, right, you should probably try to do those early on in the company. Because if you get really good at them, and you, every time you do one of those things, it should reduce your stress, even if you do a bad job. And it's the same for any sort of decision. So like firing people, right? Like that's a stressful thing to do in the beginning. But the impact of firing someone when you're a 10 person company, right? It's probably not going to destroy your company. If you avoid firing an executive or something like that, that's a huge problem when you're a massive company. It could kind of implode your company, right? And so my point of the stress maxing is you want to keep stress maxing because you'll reduce your stress for that thing long term. I like that. Shane Parrish Do you think stress focuses you? Yeah, massively. Winston Weinberg I think it's less stress. It's going through stress. And then that reduces it for the next thing. ([Time 0:24:08](https://share.snipd.com/snip/d3f46e3b-a81e-4daf-81fa-15c62e9b80cc)) - **Fast Decisions Trump Perfect Ones** - Winston values making decisions extremely fast and regrets delays more than wrong choices. - He prefers stepping up a stair, iterating, and fixing errors rather than sitting at the bottom of the stairs indecisively. Transcript: Winston Weinberg I make decisions really fast, like really, really fast. And I do that for two reasons. One is I really care about knowing what's going on in the company the entire time. And part of that is just because I've never taken any time off really. And so you just, all you have to do is update my contacts window from like the one day to the next, that's it. Like that's all I have to do. And the other part of that is I've also done every part of the company. Like I've played every single role at the company at one point. Like I've run everything at some point and then hired somebody to take that. And so that gives me a lot of confidence and I know what's going on and have a good pulse on the company. And then the second reason is everything that I regret at the company or whenever I regret something, it's not making a decision fast enough. It's not I made the wrong decision. What I've always regretted is sitting at the bottom of the stairs for too long instead of jump up a stair and then I'll figure it out and then jump up a stair and I'll figure it out and then Jump up a stair, I figured it out. ([Time 0:25:31](https://share.snipd.com/snip/72135d25-4a94-4c78-9106-c2008f99a650)) - **Instill Urgency By Hiring Leaders Who Drive It** - Maintain urgency by hiring and embedding leaders who share your tempo and can cascade urgency through teams. - Winston says culture plus hiring scales urgency; if only the CEO pushes, the company thrashes. Transcript: Winston Weinberg Here. Yeah. The best way to do this is hiring. There's no other way to do it. It is hiring and culture. And so what you need to do is hire a very good team that all feels the same way you do. And what your job then is, is how do you instill a sense of urgency into the rest of that team? And then those leaders will instill it into their team, and then those leaders will instill it into their team, right? So it's more, how do you create a culture and a hiring process that hires and promotes people that have a sense of urgency and can instill that into the rest of folks? Because that will scale. ([Time 0:29:40](https://share.snipd.com/snip/30e9095c-7724-4115-a74c-6983458f22d0)) - **Hire For Resilience And Short Term Intensity** - Hire people who believe the next 1–2 years define the next decade and who tolerate mistakes and learn fast. - Winston avoids candidates who treat many choices as one-way doors and those who break under repeated failures. Transcript: Winston Weinberg The thing I look for the most is they have to believe the same thing that I believe, which is the next year or two years are basically going to define the companies that are successful for The next decade probably, right? If not more. You have to be able to think about kind of all of your decisions is that way, right? So one of the main things that I've found that's hard with hiring people is people think too many things are one-way doors. Oh my, way too many things are one-way doors. They just aren't. And I think, again, this goes back to the stress or making mistakes. You have to just make tons of mistakes with things that you think are one-way doors to realize that not everything is a fricking one-way door. Right? I moved multiple high schools, right? I guess technically one I got kicked out of. But i moved multiple high schools it was not the end of the world each time that happened i was like yeah probably like we're done right and i remember you know i got like really bad grades In high school and my life wasn't over and i think that there are just so many folks that have these such prestigious backgrounds and they've never gotten a b in their entire lives like Ever probably right and so they think everything is the end of the world, right? And you can't hire people like that because they will break. They will massively break because the reality is these companies are moving too fast. The world is too tumultuous right now. You're going to lose, like you're going to lose so many times and you're going to lose a bunch and you're going to win a bunch and you have to have a tolerance for doing that or you're just Going to break. No one at the company ever has been let go because they made too many mistakes. It's never happened. I have personally never done it. I've never ever fired someone or anything like that because they made too many mistakes. They always broke. And the thing that broke was they started to get decision paralysis. They started not be able to scale. They didn't hire a good team. They were afraid to hire people that were better than them. All of these things that I think, again, were just, it was scary and they didn't scale throughout, right? And that's like what I'm looking for a lot is, are you able, like, what is your rate of learning? What is your, are you going to be okay with making mistakes? Can you have failures? Can you learn from them? What is your resilience? That I think is really important too. And what is your company's resilience? ([Time 0:30:28](https://share.snipd.com/snip/d5296642-bae2-4c86-867b-ea3f81075fc4)) - **Use Live Async Work To Screen Resilience** - Assess resilience in interviews by asking life stories, mistakes, and running live async Google Doc exercises. - Watch for hedging long multi-paragraph answers to simple option questions as a sign of decision paralysis. Transcript: Winston Weinberg Can ask them. Like, I try to spend a lot of time on, like, tell me about your life. Like, what do you want to do? What do you like doing? Like, tell me mistakes you've made, things like that. Like you can do it in the hiring process, right? What I like to do a lot is I go through like a Google Doc and I do like a live editing process. So I'll like come up with a Google Doc that has like a bunch of questions or like a project to do and we'll do it live async. Part of that is because I really like to work async and so I need to be able to work with someone async. And it's a good like litmus test to tell that. The other thing that it does is you can tell when some people like take too long, like they'll write like a 20 paragraph response to something. And you're like, you're just hedging constantly. Like this was basically a like option A or option B question, right? And you can tell that if they're massively hedging like that, what are they going to be like in high stakes decisions? ([Time 0:35:12](https://share.snipd.com/snip/12576fc1-a920-4801-b216-0a0caa793cd9)) - **AI Amplifies Small Skill Gaps Into Huge Advantages** - Small skill differences are amplified by models so top performers become hyper-leveraged. - Winston notes engineers and lawyers who seemed 10x are now 100x because models remove communication and execution bottlenecks. Transcript: Winston Weinberg That's what I'm seeing across our company just massively, where like the people who were, I already thought were like 10x are now 100x. And so I do think you're seeing like the power law of ability just increased by a lot, right? And there's a couple reasons for this. One is the communication, like getting rid of communication gaps, because sometimes it was hard to tell if someone was good, because really what was happening is they had a lot of good Ideas, but they couldn't communicate them, right? I know so many people that are like geniuses, but they have such a hard time communicating to other people. And the coding models are incredible at this. I'll give you a really simple example. Something I do a lot now is the models have gotten so good that i can use a really complex like something that's really complex and legal right uh like multi-jurisdictional fun formation And you have to do like the how you do tax exemptions and all these things i can just say can you give me an example in engineering that's similar to this and the models are so good that they'll Come up with like a one pager that is like a perfect comparison. That's, I know, like kind of a silly example, but there's so many ways to do translation now. And because there's so many ways to do translation, you can really see like who's coming up with good ideas. And that's maybe one reason. ([Time 0:36:13](https://share.snipd.com/snip/22704df0-67b4-4233-b29a-29100948f46a)) - **AI Commoditizes Work But Raises Value Of Judgment** - In professional services AI will commoditize execution tasks but increase the value of human judgment at decision points. - Winston predicts review and advice remain scarce because they require experience, relationships, and contextual knowledge models struggle to replicate. Transcript: Winston Weinberg There is, I want work done, which is like I deliver a work process. Product, right? And that is going to get fully commoditized. So if it is, you know, I need this contract, I need a thousand contracts reviewed. And then after I've reviewed all those contracts, I'm going to make a decision. The reviewing of those contracts is going to get automated, for sure. That decision at the top is not. And so you have one side, which is basically, you know, here is the work product, right? Or I need work to be done. And then the decision or advice. The decision or advice is not going to go anywhere. In fact, my guess is it's actually going to be more valuable over time. Why? Because you only really get that from a bunch of experience, right? And the experience is usually something that will be very difficult to distill into the models, right? ([Time 0:45:47](https://share.snipd.com/snip/8dcb9fb1-5a2a-45c3-aedf-2d9d13012d69)) - **Compete On Faster High Quality Delivery** - Speed and responsiveness will become a competitive legal advantage as AI shortens delivery times. - Winston argues firms that can close deals in 48 hours will outcompete slower firms because CEOs value speed to avoid leaks and market risk. Transcript: Shane Parrish You're probably at that point now where, you know, an LLM can digest all case law ever written, every transcript, every argument, everything, whereas a human could never. Winston Weinberg Could never do that. Exactly. And my point is the expectations are just going to change, right? Like if you think about the largest effect that email had on the legal industry was people expected you to respond with work product faster. Right. That's it. Right. Like that's the main thing that it did. It's going to be the same here. Right. Like, again, it's a supply and demand market. And so you have a bunch of competition. And if you're a firm and you say, hey, I can get this deal closed in 48 hours. And another firm says it will take me three weeks. If I'm a CEO and I want a deal to get done, I want the one that's done in 48 hours so it doesn't get leaked to the press, so that, you know, someone doesn't get cold feet or something, my stock Price goes down, something like that, right? And so there's a huge value and a competitive pressure that will come from just being able to do these things faster and at higher quality. ([Time 0:50:52](https://share.snipd.com/snip/00311239-3951-4551-a36a-87ada20b4668)) - **Founder Time Belongs To Product After Distribution** - Founders should spend most time on product once they have distribution; product is the only thing that truly scales. - Winston's biggest exec mistakes came from stepping away from product to do sales; short-term gains don't replace product investment. Transcript: Winston Weinberg So number one is once you get to a certain level of distribution, and by that I just mean some customers know who you are, founders should spend almost all of their time on product, like As much as possible. The biggest mistakes I've ever made as an exec are I step away from product and I try to make up for it with doing sales. Terrible, terrible idea. Like it doesn't work. It helps you for a couple quarters and it feels great. And you're like, yeah, I'm like saving all this stuff, but product is the only thing that scales. It's the only thing, right? And so I think like focusing on product is number one. Number two is do you have the right people in the right positions? Like, that is just so important. And I don't think I don't think you can ever spend enough time on that. That's not, by the way, just like hiring and firing at all. That's also like, is this person the right fit for this role? Are you doing a good job of mentoring this person? Are they doing a good job of mentoring their team? All of those things, right? Are there clear swim lanes um etc and then the third thing i think is vision setting needs to have flexibility like massively and so people really and i haven't got this right this is like Of those of these three these the first two i've probably done the best job of improving at least and i'm not like excellent at them but i've done a better job of improving number three Is the, which is how do you vision set at the right level? That I still struggle with massively, where sometimes remember in like Q3 of last year, I wrote this like long doc and it was like the vision for the product for like five years or whatever, A long time. And I think it was interpreted as like, okay, we should go build that right now. It was a huge mistake. And we like missed some of our product timings and launches because I didn't do a good job communicating that. ([Time 0:56:56](https://share.snipd.com/snip/23a73189-055b-409e-a969-a58f892b52a8)) - **Success Is Repeatedly Clearing A Rising Bar** - Success means leaving nothing on the table and re-earning your position every six months as the bar rises rapidly. - Winston measures success by feeling proud that the team did everything possible to clear an ever-higher bar repeatedly. Transcript: Winston Weinberg Yeah, there's a lot of ways that I think we would define success for the company, which I mean, at this point, you kind of merge with your company to some degree when you're working on it This much. But I think that I want to feel like we left everything on the table. Like we really did in the next couple of years. We had, you know, and again, I shout out to Harley for this because I definitely did steal it from him. I really feel like you have to like re-earn your position every six months. And to me, every six months, that bar gets so much higher. And right now it, I mean, doubles or triples in height. And I want to get to the point where I feel like we did everything we could every six months to get over that bar. ([Time 1:00:58](https://share.snipd.com/snip/92d9a739-72cc-4681-8ba6-0fb604db95c3))