Winston Weinberg: Speed, Stress, and Better Decisions

Summary

The Knowledge Project with Shane Parrish

Episode: Winston Weinberg: Speed, Stress, and Better Decisions

Date: May 12, 2026

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Overview

In this wide-ranging interview, Winston Weinberg, co-founder and CEO of Harvey, dives deep into the art of high-stakes decision making, living with stress, building resilient businesses, and the rapidly compounding leverage of slight skill differentials in the age of AI. Winston’s candid reflections on failures, hiring, and the nitty-gritty of operating a scaling startup are punctuated with lessons learned—many of them the hard way. Both founders and professionals in high-change environments will find tactical advice, psychological insights, and predictions for the future of knowledge work.

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Key Discussion Points & Insights

Decision-Making Systems and Prioritization

• Personal Dashboard & Prioritization

  • Winston maintains a living Google Doc, with motivational reminders, quarterly goals, critical metrics, and daily to-do lists.
  • The process of “re-ranking” tasks throughout the day is key to clarity and performance.
  • Quote:

    “The more times I click into that doc… the more I think about what I’m doing… that’s when I’m prioritizing the best by far.” (Jason, 01:18–01:59)

  • He focuses almost exclusively on bottlenecks and ignores parts of the business running smoothly.

• Thoughtful Meeting Selection

  • Uses a rule: must write a paragraph on why a meeting is worth taking.

    “For 99% of meetings… you start writing the first sentence and you’re like, I don’t want to do this.” (Jason, 02:38–03:11)

• Principles for Decision Making

  • Categorize decisions as one-way or two-way doors (most are two-way).
  • Always evaluate whether a decision impacts the #1 company priority (P0).
  • Be realistic about who will execute; don’t distract from the main goal.

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Saying No & Founder Psychology

• Short-term optics versus long-term results

  • Many say ‘yes’ to please others or grab a “pat on the back” from investors, even at the expense of the true underlying problem.
  • The pain of refusing others’ advice is offset later by demonstrable success.
  • Quote:

    “You face so much pressure as a founder… but the best ones put blinders on and do the hard thing.” (Jason, 05:07–06:32)

• The Role of Conviction

  • Founders must endure temporary disapproval for real progress.
  • Learning to say no is about tolerating short-term discomfort for long-term gain.

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Harvey’s Origin and Selling AI to Skeptical Lawyers

• Early Experiments & The "Oh My God" Moment

  • Used GPT-3 for legal analysis and found it matched expert lawyers in many cases.
  • Viral demo:

    “With zero edits on 86 out of a hundred... three out of three attorneys said yes.” (Jason, 10:00–11:30)

• Getting Lawyers’ Attention

  • Personalization is key: showing AI analysis on the lawyers’ own past filings broke through skepticism.
  • Risked live demos that could backfire if AI hallucinated.

• Adoption Stumbling Blocks

  • First impressions linger: lawyers dismissing AI for early hallucinations remain on the sidelines even after major advances.
  • Rate of technological change is disorienting.

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Stress, Urgency, and Resilience

• Stress as a Tool

  • Winston embraces “stress-maxing”—deliberately doing high-stress (and often high-learning) tasks early and often, to build resilience.
  • Quote:

    “You want to maximize it before it does too much damage…” (Jason, 24:18–24:42)

  • Firing, hiring, and product pivots become less stressful with repetition.

• Fast Decision-Making and Avoiding Thrash

  • Regret is usually about slowness, not wrong choices.

    “Everything that I regret… is not making a decision fast enough.” (Jason, 25:12–26:30)

  • Over-stressing the organization can create chaos (“thrash”), especially as the team scales.
  • Clear principles, and diffusing appropriate context, are essential as the company grows.

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Hiring, Culture, and Scaling

• What to Look For

  • High resilience, fast learning, and a tolerance for mistakes eclipses traditional markers of prestige.
  • Critical in a world where “slight skill differences are leveraged to degrees never seen before.”
  • Quote:

    “No one at the company ever has been let go because they made too many mistakes…they always broke.” (Jason, 30:26–32:14)

• Testing for Resilience

  • Tactics include live document collaboration to catch hedging, slow decision making, and discomfort with ambiguity.

• Instilling Urgency

  • Only sustainable if embedded via hiring and culture, not just founder energy.
  • Quote:

    “If it’s just you poking, you’re just going to cause so much thrash...” (Jason, 29:40–30:23)

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Compounding Power of Slight Skill Differences

• AI and Knowledge Work

  • Slightly better/faster performers will now vastly outpace their peers (“100x instead of 10x”).
  • Tools and AI models are leveling communication barriers—raw talent can shine more directly.
  • Analogous to sports: small speed differences determine outsize outcomes over time.

• Implications for Legal and Professional Services

  • Hierarchies based on tenure (lockstep promotion) will be disrupted in favor of merit.
  • Decision-making, judgment, and human skills (e.g., understanding clients, negotiation nuance) become more valuable, not less, as routine work is automated.

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State of Legal Tech & Future Outlook

• Agentic AI and Workflow Automation

  • Near-future: AI agents will run much of the basic legal work; humans will specialize as reviewers and final decision-makers.
  • Law firms will need fewer people per project, but possibly handle more projects overall.

• Impact on Firms & Clients

  • Workflow savings are not yet translating directly to cost savings for clients—tools automate tasks, not entire workflows yet.
  • As in-house counsels catch up with AI adoption, expectations and fee structures will change rapidly.

• Regulatory Barriers

  • Full AI law firms are legally impossible in most US states—regulations require a human lawyer for legal advice and set investment limits.

• Changing Legal Education

  • Recommends massive overhaul of 2nd/3rd year law curricula; emphasizes hands-on, client- and industry-knowledge over rote skill-building.
  • The core skill: critical thinking and understanding client needs—AI amplifies, not replaces, these differentiators.
  • Quote:

    “[Teaching] you are learning how to do create the critical skills that make you a good lawyer… you’re building that muscle rather than you’re learning anything about the actual law.” (Jason, 41:52–43:12)

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Hard Lessons from Leadership

• Biggest Leadership Lessons

  1. Once some distribution is reached, founders should prioritize product above all else.

     “Product is the only thing that scales. It’s the only thing.” (Jason, 56:55–57:10)

  2. Right people in the right positions—ongoing mentoring, clear roles, rigorous evaluation.
  3. Flexible vision setting—over- or under-communicating vision can sink timelines and company alignment.

• Mistakes and Regrets

  • Winston admits waiting too long on some executive hires, mismanaging the messaging on vision setting, and learning to invest for long-term retention rather than short-term wins.

• Darkest Moments

  • Nearly derailed the company in a failed “shortcut” acquisition attempt; the real resilience came afterward during the hard grind.
  • Learned to normalize cycles of failure and rebound—“it happens once a week, probably.”

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Notable Quotes & Memorable Moments

• “Building a company is a thousand failures and then a couple successes... you have to make a million bets, and then one of them pays off.”
  (Jason, 33:22–34:31)

• “Some of the best producing people on earth are terrible at communicating and terrible at working with others ... But they're geniuses. They're so good at what they do, and how do you create an environment for that?”
  (Jason, 37:42–38:19)

• On defining success:

  “I want to feel like we left everything on the table ... every six months that bar gets so much higher ... I want to get to the point where I feel like we did everything we could every six months to get over that bar.” (Jason, 60:58–61:56)

• On personal fulfillment:

  “This is the most fun I’ve ever had. Like, it’s not even close ... there was a life before this and there was a life after, and I never want to go to life before.” (Jason, 62:00–62:36)

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Timestamps for Key Segments

• Personal Prioritization System: 00:11–01:59
• On Saying No and Conviction: 02:20–07:26
• Decision-Making Principles: 07:26–08:18
• Harvey's Founding Story: 08:18–12:57
• Overcoming Lawyer Skepticism: 13:03–15:22
• Adoption Lags in Law: 15:22–16:27
• Resilience after Setbacks: 19:34–21:37
• Harnessing Stress, Speed, and Focus: 24:00–28:28
• Scaling Urgency & Avoiding Thrash: 29:36–30:23
• Hiring for Resilience Over Pedigree: 30:26–32:52
• Compounding Skill Differences: 36:03–41:29
• AI’s Legal and Economic Impact: 48:56–56:48
• Leadership Principles & Vision Setting: 56:48–59:01
• On Defining Success & Fulfillment: 60:54–62:36

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Conclusion

Winston Weinberg’s approach merges rigorous, almost ruthless prioritization and decision making with a deep respect for building resilient systems and teams. His personal experiences—often gained through painful, high-stakes missteps—offer palpable lessons on conviction, focus, and evolving leadership as organizations scale. Above all, Winston’s vision is one where the relentless pursuit of better decisions and learning from failures—amplified by AI—becomes the ultimate edge in a rapidly shifting future.

Transcript

[Jason]

The next, you know, year, two years are basically going to define the companies that are successful for the next decade probably right. If not more.

[Interviewer]

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?

[Jason]

So basically 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 I 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, 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 hire, 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, 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 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.

[Interviewer]

What do you say no to?

[Jason]

Most things. And I think an increasing amount of things as the company goes on. I used to say no to almost nothing.

[Interviewer]

What's your inner monologue when you're sort of looking at something and you're trying to decide, does this make my list?

[Jason]

Yeah.

[Interviewer]

Or do you capture it or do you just let it go? Like, what is that?

[Jason]

When I get really bad at it, I ask my chief of staff to force me to write a paragraph about while 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 wanna do this. And if you don't wanna do this and you' 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 gotta write that paragraph, I could write 20 pages. Right?

[Interviewer]

And it's easy.

[Jason]

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. 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 built a machine, it's like, you're never going to hire the right stat. 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. And I try to focus on, like, the number one thing that's burning.

[Interviewer]

I want to come back to meetings for a second because 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. You, this paragraph, you're. You're stressing, you're like, oh, this doesn't make sense. I don't want. Is that because we want to be liked?

[Jason]

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 that 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 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 what I've found is a lot of the best founders that I look up to, they've had tons of moments where the entire outside world is like, go do this thing, go do this thing. You need to improve something. And they just put blinders on and they completely ignore everyone and they go do the hard thing that they know is actually going to fix the problem long term. And then six months later or a year later, I mean, hell, sometimes it's 10 years later, they're right. And I think that that's the reason people have a really hard time saying no is because you get instant gratification from doing the, from making progress in the way that people think progress is made. You don't get instant gratification from being like, I think you're wrong and I know the business better than you do and really I need to go do this other thing. But that's going to take me six months to prove you wrong. That takes a lot of conviction and a lot of discipline to be able to do that.

[Interviewer]

If you were to create a Google document of your principles for decision making, what would be in it?

[Jason]

So determine if something's a one way or two way door immediately. Like that's the first thing, right? 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? 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.

[Interviewer]

How would you explain Harvey to somebody listening to this who doesn't work in legal?

[Jason]

What we're doing is building a system for lawyers to use all of these models to do their work in a much better way and much more streamed lined way. That's an incredibly broad explanation for what the company does. Another way to think about it is we are basically tracking the progress of all of these models in the system and applying it to an industry, right? So in a way, what you're kind of doing is building like a legal brain. Right. And it's the same thing that other folks are doing in other verticals, like in the medical vertical. It's like what you're trying to build over time is a medical brain. There are a lot of things to break down there where what you have to do is, okay, where is model going to do a lot of the work? Whereas a human can actually be reviewing this. How do you change the processes and structures of legal departments and law firms? How do you change the process of delivering these services? It's less just, hey, we produce a product. It's actually these products are transitioning to how does the product redefine how the profession actually operates?

[Interviewer]

So was there a moment when you were an associate and you're like, oh my God, we need to start. Yeah, this firm. What happened?

[Jason]

So I got very lucky where I met my co founder. Yeah, Gabe. And he had a background in AI research. So he was one of the first folks at the Google Brain. He was the first Google Brain class, actually. And then he worked at Meta after that and we became really good friends. We lived together for a while. And he at the time was trying to kind of push LLMs@MEDA, like pretty, pretty hard. And at some point I was like, can you just like, what is an LLM? Can you show me one of these things? And what was available at the time was a public access point API to GPT3. This is like early 2022, right. And so everyone had access to this. This is very public. I'm very confused at why not more people use this in like other industries or just were talking about it and I started messing around with it. And the first thing I actually did with it was I used it to like help run a Dungeon and Dragons game. It was like the. I was actually really good at that. And I used it for that at first. And then I was on a pro bono case and it was for landlord tenant law. And I don't know anything about landlord tenant law or like, I learned a little bit in law school, but I didn't remember it. I started using it to do very basic, like, here's a fact pattern, here's a statute in California, you know, apply this fact pattern to the same statute or the statute to the fact pattern and it got really good outputs. Then to kind of like test it even more, we went on r legal advice, which is a subreddit where people ask a bunch of legal questions 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 a hundred of those questions, three out of three attorneys said yes. And that was the oh my God moment for me and for my co founder where we said, we need to do something in this industry.

[Interviewer]

And so what happened next, you get this, you get the response from the lawyers and you're like, holy shit. And then what we.

[Jason]

So we got all of those outputs and the thing that was happening kind of like simultaneously is Gabe had some friends that were thinking about joining this company called OpenAI. We basically said, hmm, we're using GPT3 to do this. Let's just cold email Altman and the general counsel at the time, whose name is Jason Kwan, 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 like pretty fast. We met with Jason first and just kind of like went through what we did in the process with Reddit. We showed them like our chain of thought prompts and things like that. And then we met with the rest of the leadership team on actually the 4 of July and we pitched them our idea for the company and we raised money after that.

[Interviewer]

And they were your original investor?

[Jason]

Yeah, we didn't go to any other VCs or anything like that. I mean, I don't, I don't have a tech background and I'm not from the tech industry. So I mean this really was. Hey, like we experimented with this. We think this is an incredible direction. Like if these models get even slightly better, this is going to change this entire industry. Did you know how good they are right now? And do you know anyone doing this?

[Interviewer]

Talk to me about how you used to convince lawyers that this was viable and good product.

[Jason]

Yeah, 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, started with litigation examples and there's, there was a nice advantage where a lot of what you file and 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. And so on the demos, 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'd 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, 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 in, 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 guy's with his video games like this, and then all of a sudden you logged in. Yeah, it's like that. And they would just watch the screen and read every single word that came out of Harvey super risk. 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. I 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. And so I think, like, a lot of what we had to do in the beginning was literally just get lawyers to pay attention because they're super busy. Right. And it was just figuring that out. The personalization of all these demos matters so much, because I don't think you get it until you really feel it on something that you work on.

[Interviewer]

I feel like so many people tried ChatGPT on, like, the first week.

[Jason]

Yeah.

[Interviewer]

And they were like, oh, it's hallucinated. And they kind of wrote it off.

[Jason]

I think they're still not using it because of that. Like, I think there are still Folks that have tried this like three years ago and they had a hallucination one time and they're like, yeah, we're not going to do that. I mean, we had this with Harvey where we had, you know, we've had so many folks that said, we trialed your product like three years ago, we didn't think it was good enough. And we don't, you know, we're unsure if it's improved. And then they log in and they're like, I don't even remember trying the product three years ago. Like, this is so different. And I think that also that rate of technology change people aren't really used to, and especially folks that are not in the tech industry, right? And with what's happening in AI right now, every release is a massive step change. And I think it's hard for people to wrap their mental model around that and think about, oh, how do I create? How do I become, you know, antifragile, where I'm okay with making different choices and really think about the future when everything is changing so quickly.

[Interviewer]

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[Jason]

Yes, I think, like hiring senior executives. I've been very up and down about it. I think I was told to, I was told to hire senior executives very, very early on and I refused. And then I refused too long. I refused like, I'd say about six months too long. But if I would have taken the advice when it was given, I think it would have been a huge mistake.

[Interviewer]

How did you know that you were late?

[Jason]

I saw the impact of what happened when I hired them. The main advantage of being a founder of a company is if you are always on, which I tried to be. What you have is you have the context from day one, right. And if you're always on your brain, all your brain has to do is do the delta between day one and day two. Right. And so the reason founders are so valuable, I think, to understanding their business and looking forward, and both looking forward and looking back is actually just because the cognitive load of taking everything about the business day over day makes it so you can kind of understand everything that's going on and it's not incredibly difficult to do that. Whereas if you're a newcomer and you just come into a company, you don't have that. And so you're starting from zero and you have 10 years of context that you have to somehow absorb. Right. And so my, my point in answering that way is you just have a very good pulse on the company and you can tell, oh, if I would have made this change about six months ago, this would have moved these things forward and this problem about hiring the senior exec wouldn't have existed. And I waited a little bit too long to do that. Right. You just have a sense for it.

[Interviewer]

What was the darkest moment as you were building this when everything felt like it was just caving in and you were about to give up or quit?

[Jason]

One of them was super early on we thought, we basically thought that there was going to be a way to like one shot ourselves into like building the company instead of doing it the hard way. And the way we. This was like early 2024, so about, like a year and a half into the company a little bit less. The idea was basically we're going to buy this company that ended up, it was 10 times bigger than us people wise and about the same. Like we were going to trying to buy the company for the same, a little bit higher valuation than we are valued at. We tried to buy it. We kind of like Signed actually the deal before we had the money. So, like, what old private equity funds used to do, right, Like KKR used to do this all the time, where they basically like, sign the deal for the leverage buyout and then they go raise the money. It was a very common thing they used to do. And that's kind of what we did. 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, pick. The problem with those is if you take that debt, if you don't fulfill the debt obligation, somebody else can own the company, right? So it's not in, in dollars. It's actually in percentage points of the company. It's called payment in, kind of. 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. I was just like, I don't think. I don't think, like, we can build fast enough. I think the model providers are just going to eat us. I think that, like, without this other company, we're screwed. And it forced us to basically go and, like, build the company. Like, actually build the company. Like, go hire the right people, put the right work into product, do the correct scaling processes, do all of these things.

[Interviewer]

What was the process from that not working out. And the moment you knew this wasn't going to happen, you see that as failure to getting to that point where you, what was your inner monologue?

[Jason]

It was like 24 hours. Um, it was really fast. And I think, like, the reason it was so fast. And by the way, I've had a lot of periods like this. Like, I've had other times when we've, like, failed massively. And I have like 24 hours of like, it's all over. And then you, like, wake up the next morning, you're like, we can do this again. I mean, hell, that happens once a week probably. You get used to it. And like, I think I've had a lot of times in my life when I thought everything was over. Like, when I, like, basically failed out of my first, like, high school I went to, I was like, this is over. This is done. I remember when, like, I took the LSAT for the first time, and I didn't quite get what I got. I was like, okay, well, that's over. But my point is, you just have to get used to this. Of, like, it's over, it's over, it's over, it's over. And then everything's fine. And now, you know, you take those moments, and then you just get, like, a. You build resilience. Like, you build resilience for. For losing, for, you know, suffering, things like that. And I think you get the same thing in the company. And one thing that gives me. I'm more confident in the company today than I've ever been confident about the company. Which is weird, because externally, we face way more threats than we did last year. It's not even close. Like, it's 10 times the amount of threats as we did last year. But the reason I'm so much more confident in it is I now have a team of people that I have failed with so many times. Like, we have taken crazy risk. We have massively butchered product lines and then recovered them and made them much better. We have made the wrong hires. We've tried to buy a company super early on that would have collapsed us. We've done all of these things. You know, we've had tons of folks be like, it's over. And because of that, I just feel very confident in my team's, like, resilience and their ability to adapt and strive and get through the next problem. And, you know, I don't, like, wish this upon the company. Like, I don't wish, like, that tomorrow. There's also, like, a crazy chasm, and we're in a huge amount of trouble. But I kind of do in the sense of if we get all of those done now, then we'll get better way faster.

[Interviewer]

Not everyone sort of buys into, like, Zen being the best way to unlock yourself. How do we make stress work for us? Because when I listen 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.

[Jason]

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.

[Interviewer]

I like that. Do you think stress focuses you?

[Jason]

Yeah, massively. Um, I think it's less, it's less stress, it's going through stress and then that reduces it for the next thing. Like, I think like one of, one of the things that I've, I'm good at for this is maybe not even good at. It's just I do it a lot and it's could be good or bad. 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 I 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 and I think like the, the problem with that is that can be really thrashy. And so a lot of what I'm trying to do is like, here are the principles for how I make decisions and as a team, can we come together on those principles so we all make faster decisions? And I think that's like the next scaling challenge that I need to do to Be honest. Where like, I think in a way the operating system kind of right now is like, okay, what is my anxiety? And then I push on different parts of the company based off of that anxiety. And the way I want to transform the company, and I think we're starting to do it, is here like the general concerns. And this is how as a company based off of these principles, we approach them. And I'm just starting to do that, but I think that's like the next step.

[Interviewer]

Would you say you're hypersensitive to threats?

[Jason]

You have to be to some degree. Right. But you don't want to over rotate either. So one thing I think I did wrong last year was there were like a multiple threats to the company that I overreacted to. Right. And one thing that happens to you as a CEO is the diameter or the amount of pressure that you can exert increases massively. What do I mean by this? When you're like a 50 person company and the CEOs stressed about something, right. Everyone kind of knows each other and so they all kind of like know how to react to that stress and they can kind of absorb it and we all move on. When you're an 800 person company, if the CEO gets too stressed about something, the whole company will move based off of that stress. And that is such a big problem. That's how you create thrash. You create thrash by. You get overly stressed about everything and then people don't know. I mean, it's like the boy who cried wolf. They don't know what actually matters, what doesn't matter. And so a lot of what you have to do, I think as a founder, is figure out how do I manage my own stress and then how do I explain and diffuse this stress throughout the company in a healthy way.

[Interviewer]

How do you take care of yourself?

[Jason]

It's a good question. And it's a work in progress. Like getting enough sleep and working out are the main things. For me, it's not even close. If you wake up right in the morning and you go on a run, I found that that's like incredible because everything else through the rest of the day you get a shock basically, and then the rest of the day you calmer for everything else. So I think that works super well. The other thing too is prioritization. So a lot of the reason people get stressed is because they're doing too many things and they can't. Everything feels like chaos, right? But if you prioritize things correctly, I think that you can actually know and have like A very good handle on all of the problems at the company. Right. Because what you do is you take the stuff that isn't really a huge problem and you just put that somewhere else. Right. And so all you're paying attention to are the problems. And if you do that over time, you're way less stressed. Because you might be stressed about one thing, but it's again, not as thrashy. You aren't poking as much because you're trying to fix the same thing. And you don't feel like there's a thousand things that are going wrong. You feel like there's one thing that is terminal. Right. But you can just focus on how do you incrementally improve that terminal issue.

[Interviewer]

How do you maintain urgency? You're sort of in a sprint here.

[Jason]

Yeah. The best way to do this is hiring. There's no other way to do it at his 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 SC scale. If it's just you poking, you're just going to cause so much thrash that the company's not going to move in a good direction.

[Interviewer]

What's the one thing you look for when hiring people?

[Jason]

Like the most critical thing right now when I'm hiring executives, the thing I look for the most is they have to believe the same thing that I believe, which is the next, you know, year. 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 like moved multiple high schools. Right. I guess technically when I, when 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? 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 gonna lose, like, you're gonna lose so many times, and you're gonna lose a bunch, and you're gonna win a bunch, and you have to have a tolerance for doing that or you're just gonna break. No one at the company ever has been let go because they made too many mistakes. It's never happened. I've. 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 to 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 I. 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? Like that, I think, is something that a lot of companies are going to face pretty soon.

[Interviewer]

I think people often, they don't step their decisions. It's like, I'm going to walk to the top of this flight of stairs. And they don't think about, well, to get to the top, you're actually going to take one step and then another step and then another step. Why do you think that people look at decisions that way?

[Jason]

It's less scary. So I think there's actually another problem with that. Like, to use your analogy of you're walking to the top of the stairs, right? And they will basically plan out. These are the stairs that I'm going to walk on each way to the top.

[Interviewer]

In this spot.

[Jason]

In this spot on the. Yeah. Yeah, Maybe there's like 10 options of stairs. And it's like, I'm going to do this one, then this one, this one, this one gets to the top before they start walking. What's even worse that I've seen is A, people do that, which is bad in itself, B, is they start walking. And you can imagine that each step in the stairs, you can see more, right? You can see, like, more about your surroundings. You'd see more about the path ahead of you. And they're stubborn and they go, no, I won't change. And I'm step three in. And I've. I can see being step three in that, like, I only need to take one more step, but I'm gonna keep doing it the way I said I was gonna do it, because I don't wanna be wrong. I don't want to have to adapt. I don't want to have failed. People are just so afraid of failure. Like, they're so incredibly afraid of failure, and they think of the wrong thing as failing. Like, building a company is a thousand failures and then a couple successes. And I think what people don't realize is that you have to fail constantly in order to succeed at bigger things, right? Like, you have to make a million bets and then one of them pays off.

[Interviewer]

And.

[Jason]

And people are really unwilling to do that because they think each one of those bets is a failure and then you're done. I think Elon has tweeted something about this too, where it's like, the first 50 times you fail, it, like, really sucks. It's awful. And then you just, like, don't care. And there are some people, again, maybe this is going back to, like, the optimizing stress, optimizing failure, optimizing these things. You want to build that tolerance really fast. Because if you don't build it fast for the smaller things, like the baby steps, then you're not going to have it for the big things. And if you can't do that on the grander scale, right, and the grander stage, I guess, then you're going to fully collapse.

[Interviewer]

How do you assess resilience when you're hiring somebody?

[Jason]

You 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 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, you know, 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?

[Interviewer]

It seems like we now live in a world where a very slight difference in skill is leveraged to a degree it's never been leveraged before. Talk to me about that.

[Jason]

Yeah, 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 a hundredx. And so I do think you're, 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. There's so, 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. Like multi jurisdictional fund 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, you can really see like who's coming up with good ideas. And that's maybe one reason. The second reason is you just don't need to communicate. Like you can just go and on the weekend On a Sunday, if you're a really good engineer, you can just go build something and then just shoot it off into, you know, the general slack and people can see what it is. And so you don't even need those communication barriers. Right. Some of the, some of the best producing people on earth are terrible at communicating and terrible at working with others. And a lot of what you sometimes have to do as a company is how do you create a situation for those folks to succeed because they can't manage up, you know, they don't look as prestigious. They maybe not don't have like the resume that everyone likes. They aren't as good at communication. They can be hard to work with, but they're geniuses. They're like incredible. They're so good at what they do. And how do you create an environment for that? The coding models are going to make it so that those folks can do better, like, better than they've ever done before.

[Interviewer]

What do you think of the second and third order consequences of slight variations in skill being leverageable to a degree we've never seen before?

[Jason]

I think it's the same thing that happens in sports. Right. So like in sports being a little bit faster compounds. Right. If you're a little bit faster than your opponent in basketball, right. You will just slightly get the ball in front of them every time. You will slightly put your hand up a little bit higher to get the shot off. Right. You will slightly put your hand in front of their hand before they pass the ball and block it. Right. Like, I think it's the same thing where you can take those competitive advantages and now all of the sudden you're winning most of the time. Right. And I think that that's what's going to end up happening in knowledge work where, you know, if an attorney is, is slightly better or slightly faster, they're going to get all the work. And that, that kind of already does happen, by the way. Like, you have this thing at a lot of the law firms where, you know, you call them rainmaker partners and you know, there's an argument of like, how many, how much better are they at every single task than everyone else? Like, probably not that much better, but they're slightly better at a couple things. And then those things compound and then the vast majority of work goes there.

[Interviewer]

I was thinking, as you were saying, that one of the, I don't know, my mind just went off here. But you can identify who has good arguments and who has bad arguments.

[Jason]

Yeah.

[Interviewer]

In law firms. So you could identify like junior associates who actually have the strength of argument.

[Jason]

Yeah.

[Interviewer]

Of maybe a senior or partner level associate.

[Jason]

And this is a really good point is right now, in, in law firms, it's basically lockstep. So if you're better than everyone else in your class, you get promoted at the same rate everyone else does until like you're eight or nine and then they decide like, if you're going to be partner or not. Right. And I think law firms are going to, they're going to have to change this. Like, they're going to have to say, hey, this associate is better. Like, this associate is better at X, Y, Z, and we are going to promote them faster than the other ones because that time to partner is going to matter. And I think there are a lot of industries that are lockstep and you basically get rewarded by how senior you are, not how good you are necessarily. And I'm not saying that like wisdom and knowledge from being, you know, more senior isn't important. It can make you better, but in some instances it doesn't. Right. And I think that's something that we've tried to balance a lot at Harvey, where we hire a lot of like, execs that have been there, done that, but we also promote a lot internally. Right. Because sometimes folks are better than executives that I could have hired that were more senior who have seen that, done that because they just have higher raw talent. And so it's better to invest in the junior because the slope is just going to keep going and in two years, three years, they're going to be way higher than the senior exec that you thought about hiring.

[Interviewer]

Totally. It's almost like an equalizer or meritocracy or bringing more merit base to firms that are.

[Jason]

I think that's right. And I think like, my gut is firms are going to start thinking about that more and more. Part of it is because you know, the, how fast you can learn, how much you can adapt, how well you can interact with clients. Those things can compound. Right. Vs oh, I've just been doing this for a long time and so I understand the law better than you.

[Interviewer]

What would you tell people in law school today?

[Jason]

The weird thing is I would actually tell them the same. The first year of law school is, I think, perfect. It's like really good because the first year in law school you take like basic, like contracts, con law, all these things, and most of the cases you read about and the law that you read about is not good law anymore. Like, it's law from like 50 years ago or something like that, oh, it's not relevant. It's not super relevant. No. But why it's helpful is it teaches you how to critically think, it teaches you how to make arguments, it teaches you how to do research, all of those things that's super relevant. Right. And I don't think that's going to go away. It's, it's maybe a little bit kind of like you are learning how to do create the critical skills that make you a good lawyer. Right. And you're building that muscle rather than you're learning anything about the actual law. And then the second and third year of law school, I think those need to be massively changed because the second and third year of law school you kind of take like some specialty courses and things like that. I don't think it's as relevant anymore. You need hands on experience, I think starting then. So the thing that I would tell law students is actually pretty much the same, which is I think that if you can understand like your clients super well and you understand an industry super well, you're going to do, do great. Like AI isn't going to massively impact you if you think that your competitive advantage is you are the best at writing briefs or you are the fastest at doing research or something like that. That was never your competitive advantage. Like I don't think it ever was. Right. And if you look at like the top lawyers who succeed really well, those are the ones who I think have mastered what you master in the first year of law school, plus understand a business and understand their clients really well. And I think that that is only going to have a premium. Right. And I think this is going to happen across every industry where whatever the top things are in that industry are just going to get compounded. I don't think that those things are not like no longer going to be the top skills. I think it's just the other skills really don't matter. Does that make sense?

[Interviewer]

Yeah. So it's sort of like slight variations in your skill or your argument will be amplified massively.

[Jason]

Yeah. And. But your ability to read a room, your ability to understand, you know, it depends on the practice area. Right. Like if you're a trial attorney, My sense from the best trial attorneys that I've met is, you know, a lot of what they're very good at is like coming up with a story that makes sense to a jury. Right. And I don't see how these models are necessarily going to make that not relevant anymore. Right. I think that that's still, you have to understand Each jury member. And yes, there's tons of AI you can use to like get more data and things like that on what works and a B test, etc. But at the end of the day, I think that that's a very human ability to kind of like sit in a trial, in a courtroom and understand, ah, I think that, you know, this is the type of, this is the. I should argue this case that makes the most sense. And then the same, you know, if you're an M and A attorney, the folks that I've met that are the best deal attorneys, it's like they're not the best at like drafting spas or going through diligence rooms or anything like that. What they're the best at is the two principals. You know, the folk. One person's trying to buy a company and the other one's selling it. They're really good at, oh, we're arguing about something. How are we going to figure out how to mediate that argument? Or, you know, there's 10 things that they're asking for, but I think to be honest, they only want number two. Right. And the other ones I think are smokescreens. That's the type of skill set that really differentiates lawyers today. I don't see that being any different tomorrow. I think that it's just going to compound the amount that, that it gives you an advantage as an attorney. And the value is going to accrue to those decision points instead of all the work that's being done to make the decision.

[Interviewer]

Does that because a human is doing the decision point. Is that why the value is there?

[Jason]

Yeah, exactly.

[Interviewer]

But do you think a human will, I mean, in the foreseeable future always be doing that? Or does AI get to a point where it's actually better than humans at that?

[Jason]

Yeah, I think maybe a good way to think about this is in professional services. I think there's two types of work. There are. There is, I want work done, which is like I deliver a work 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, 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.

[Interviewer]

Why?

[Jason]

Because you only really get that from a bunch of experience. Right. And the experience is usually something that'll be very difficult to distill into the models. Right. So an example of this is when you're doing a large M and A. A lot of the very good, like top M and A attorneys, what they are good at is they actually know personally all the other folks, like all the players. And so what they're ending up becoming is actually like deal advisors of. I know that this is actually what they want. I know that this is what they're going to push back against, et cetera. And I think it's going to be very difficult for the models to get that data over time.

[Interviewer]

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[Jason]

look like in five years, My guess is we're going to get to a stage where agents are running a very large portion of this and humans get really good at reviewing the outputs of agents and understanding where they might have made a mistake. This is also what senior lawyers are really good at already.

[Interviewer]

So law firms, and what it sounds like is they'll be getting smaller and doing more work.

[Jason]

I don't know if law firms are necessarily going to get smaller because there's actually a world in which, because AI allows you to institutionalize your knowledge faster and work across a lot of different projects faster, you might actually be able to scale faster as a law firm than you used to be able to in the past. But you will need less people per project. Right? But the other thing, as long as you have less people per project, you might have like way more projects. So I'll give you a really good example of this or like a very simple one. We are going to have a bunch of regulations about AI use, for sure. There's no universe in which we aren't going to end up there, right. In the same way we have a lot of audit restrictions on banks, right? For like when you make a trade, you have to put XYZ down. That's going to happen for models, for sure. Right. Who's going to be in charge of that? Monitoring that? Lawyers, Right. The legal department. And so there is an area where I think like there is going to be a massive expansion of legal work. Think about like a data room, what a data room is going to have in 10 years. If you've been using AI to create all the contracts, it's going to be 20 times larger, right? 50 times larger. It might get to a point, honestly, where we have agents that are basically creating all the contracts, negotiating with each other. And a human can't absorb all this data. Like, you literally can't. Like, it has to be an agent plus a human, otherwise you wouldn't be able to do the complexity of these transactions.

[Interviewer]

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, could never do that.

[Jason]

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 gonna 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'll 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.

[Interviewer]

Faster and more accurate. Is that what you mean by quality?

[Jason]

For sure. One way to think about the professional services is they're cyclical and countercyclical, but mostly cyclical. Right. And so like legal, I'll just use legal for as an example. A lot of the revenue from the top law firms comes from M and A. Right. Or transactional work, which is mostly cyclical. Right. And so the economy goes up, the economy booms, and you have more M and A. Right. And so I think that folks think a lot about legal in a vacuum where they say, oh, these LLMs are going to get so good that they can do all legal work, et cetera. And what they're missing is it can do legal work today. What does legal work look like in 10 years? Like, what is the product review for a lawyer look like when meta can ship 50 times as many products daily? Right. That is going to change a lot of this world.

[Interviewer]

And you don't see a world in sort of the next five years where there's like almost an all AI law firm where it's, you know, I call up, I get Harvey on the line, and I give my case, I give all the facts, and then all of a sudden all the briefs come out, all the information, the documents get filed with courts.

[Jason]

So you can't do that in the U.S. right now. So you need a lawyer. Basically, there's two rules. One is state by state, which is the unauthorized practice of law. It's actually a felony, and so you actually need to be barred in order to give legal advice. And then the other one is an ethical rule, so it's by the aba, which basically says that you can't have non lawyers invest in a law firm. And so the combination of those two make it actually impossible to do what you just said, other than in Arizona and Utah, where they have changed the rules to create a sandbox. They've created like A regulatory sandbox where you can experiment with that and you don't actually both of those are gone. Yeah.

[Interviewer]

That's fascinating. Do lawyers have an obligation to disclose that they're using AI on client work?

[Jason]

It completely depends on the client right now. A it's jurisdiction by jurisdiction and state by state. But right now mostly it is driven like the consensus of it is driven by client by client. So and that's changed a lot, right? Like over the past three and a half years, I'd say it's changed every six months, three months maybe where some clients are like, you can use it on this, you can't use it on anything now. You can use it on everything.

[Interviewer]

Right.

[Jason]

And the transition like most generally has been 2023 was don't use it at all or you have to tell me exactly what you're using it for. Don't use it. And if you are, you have to tell me exactly how on these like very small use cases, 2024 was you can use it by certain different types of matters. So like I'm okay with you using it for IP work, but I'm not okay with for you using it for, you know, something else. And then 2025 started being, you need to use it and you need to tell me how you're using it and how are you saving me money?

[Interviewer]

I was talking to somebody in private equity a couple nights ago who spends a fortune on legal fees and they had mentioned one of the things that surprised them the most is they're not seeing those legal fees come down at all. All despite the firms that they're engaged with using tools like Harvey on the back end. Why is that?

[Jason]

I think that there's two reasons for this. One is the tools at this point do task automation, but they don't do like entire workflow automation. So it's hard to exactly say where the savings are. Right. So my point with this is like the, the tools are not at the point where they can automate entire diligence. Right. They can automate bits and pieces of the diligence. And so I think it's hard for the law firms right now to come up with exactly how much time have they saved? Exactly. You know, what are the benefits? An ROI of these tools that's going to change really, really fast. And we're starting to see that change fast now. The other thing that needs to happen, I think is the in house teams, as they adopt it more and more they understand what the law firm could be using. Right. And for a while the in house Teams weren't really adopting this. They were about a year behind. And so they didn't really have insight into like, what could you do with the tools, right. Like how much of this work could be done by AI, et cetera. And I think that there needs to be a lot more communication between the two sides and a lot of what we're doing with our product. And this is what I was talking about earlier, where it's not just a product, it's basically like, like how do you map the product onto like what are the problems in the industry and move the industry forward? A lot of what we're doing is how do we build something that's collaborative between the two. So, you know, an in house team can work with a law firm plus AI and the law firm's using AI to the best of their capabilities. They use, you know, their expert data and all of those things on top. The in house team does the work that they want to do and then they pass the rest of the law firm, all of them.

[Interviewer]

That if you had to distill the three biggest lessons you've learned about running a company into principles, what would they be?

[Jason]

Yeah, 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. All, 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, et cetera? 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, 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 at improving. Number three is the hardest, 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 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. And so like what level of vision setting are you doing is really important for building a company And I think I still need to do a much better job of that. Of like when do I do the super high level vision and when do I do the like. No, no. What do we need to do today? What do we need to do tomorrow? Still have struggles with that.

[Interviewer]

We've talked about a lot of things you've got wrong today. What do you think you've gotten right?

[Jason]

I'm really proud of my team, like insanely proud of my team. And it's hard because I like, I have very high standards and I'm harsh and actually if they listen to this, this is probably the first time I'm saying I'm part of my team. No, but like I can definitely be like pretty harsh. But I think that like we have built a very resilient group of folks and they really care like about the company and it feels like to me, if we can survive the next like kind of chaos years, I think that we are really set up for the long term and I'm really proud of that because I'd rather that be the case than we're like a flash in the pan company and we've done a lot of things that are really good for like short term growth and all that, but we haven't set ourselves up for long term. But I think that because of the choices that my co founder and I have made and a lot of the choices on who we've hired and how we've thought about structuring the team and what we've thought about building and how we've done our brand and which customers we want to work with, how we treat our customers, all of those things, we're really trying to think about the long term and we've sacrificed some ground on the short term by the way. We've sacrificed a decent amount of ground to Competitors, because we really wanted to land customers and then keep them. And so we've invested in a tremendous amount on what happens post sales. That's a small example. But it's things like that that I would rather. We don't have a ceiling as a company. I'd rather set up and feel like that than feel we're going to maximize, like, the next three years and then, like, we're screwed. But at least we maximize the next three years. I don't know. It's been hard for me to do that. It's hard to do that when you have, like, the looming, you know, everything else that's going on. But I'm proud of that.

[Interviewer]

We always end with the same question, which is, how do you define success? Success?

[Jason]

Yeah. There's a lot of ways that I think we would, like, define success for the company, which, I mean, at this point, like, 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. And that would make me feel incredibly proud of whatever we've built, honestly. And I think that would make me feel proud of the team and proud of everything else, too.

[Interviewer]

It sounds like leaving it all on the field is part of how you would personally define success, too.

[Jason]

Yeah. And I think, like, for me, you know, I didn't really find my way for, like, 27 years before doing this company. And I definitely had some periods of my life of, like, dealing with pretty bad, like, mental health problems and things like that. And this is the most fun I've ever had. Like, it's not even close. I mean, this is also, like, it's very painful, but it is by far the most I've ever enjoyed life. It's. It's. It's genuinely not close. Like, I feel like. Like there was a life before this and there was a life after, and I never want to go to life before. And so I think I'm just extremely grateful for, like, the position I'm in. And I don't want to lose that position. Like, I just don't want to lose it. And I don't want to feel like I, you know, kind of didn't put everything that I possibly could into it when I had the opportunity.