Pod Insights How I Invest with David Weisburd E339: From Zero to $100 Million in 18 Months: Inside Legora About this episode What happens when AI turns a $40B legal software market into a $1T opportunity?
In this episode, I talk with David Eckstein, CFO of Legora, about scaling one of the fastest growing enterprise AI companies in history. David explains how Legora went from zero to $100M in 18 months, why AI is expanding markets rather than just disrupting them, and how the role of CFO is evolving into a strategic operator across every part of the business. We discuss vertical vs horizontal AI, why AI companies must focus on workflows instead of prompts, and how talent density and culture become the ultimate differentiators in high growth environments.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 David Weisburd? Legora is the fastest growing enterprise company in history. What's allowed Legora to scale so fast?
0:05 Speaker 01 Legora is a truly special company. We have been able to grow from $100 million in 18 months, setting a record in terms of execution. There are 2 billion people around the world that have experimented with AI. But more importantly, there are over 600 million people on a daily basis that use AI in their workflows, in their workforce, at home. If you think about the enterprise, over $100 billion exists in the enterprise TAM. And so Legora focused right here.
0:37 David Weisburd? There's this whole argument about horizontal versus vertical AI. Who's going to win in what verticals?
0:45 David Weisburd? Why is Legora going to beat the horizontal players?
0:47 Speaker 01 The legal software space is a $40 billion opportunity, and it is incredibly siloed. You have document management systems, you have case law, you have the management of work, you have business law. And what Legora is doing is providing a centralized operating system for legal services. Great, that's act one. But that's a $40 billion TAM. If you think more broadly, though, legal services is a trillion dollar TAM. And what we're really doing is helping lawyers do their work more efficiently. Whether it's big law, so the AM200, or it's corporate law, we are helping them complete their tasks with automation, with expertise. And so we're turning that associate
1:32 Speaker 01 from the person who is drafting that documentation into the first reviewer. And that's that $1 trillion TAM that we're going after.
1:39 David Weisburd? One of the, I think, underappreciated aspects of Legora and the legal TAM is the expansion of the TAM. We saw this famously with Uber. Uber was going out with Sli Dex, talking about if they could get 20, 30% of the taxi market, that'd be a huge business. They ended up being 10 times the size of the entire taxi market. They expanded the TAM. Why? Because before, you would only take taxis to go to the airport or for very specific cases. Now, when the cost went down, you would take it to visit your friends, you would take it to a restaurant.
2:06 David Weisburd? Do you expect the legal TAM to expand if the cost of legal goes down?
2:11 Speaker 01 There is no question that if the bar to engage with a lawyer or to engage with legal services were lower, you would ask more questions. How many times have you come up with a patent idea that you wanted to explore or run a patent check or submit to the patent office? When faced with the concept that it's going to cost you $10,000, you back away and you no longer pursue that patent idea? Or unfortunately, you were wronged in some way and you know that you could probably sue someone for the injustice that you were incurred. If you lower that bar to engage with legal services, that entire pie will expand. And so I believe with Legora, the entire legal sector will expand way beyond the trillion dollars that exist today. And then on top of that, Legora, again,
2:54 Speaker 01 the first inning is legal services. But there's a much broader opportunity outside of that. Our goal is to expand to all professional services. And there's natural adjacencies in audit, tax, risk, compliance, that's there for the taking.
3:07 David Weisburd? What keeps somebody from an OpenAI or Anthropic from doing this?
3:12 Speaker 01 OpenAI and Anthropic are great partners of ours. We work extremely closely with them. We leverage both of their models. And every month or two, when they release a new model and the ground shakes beneath us, our solutions get better with those models. Now, there is the work that's actually getting done, which depends on these engines. But then there's the rest of the chassis around the car that's really necessary to get from A to B. We're really focused on the management of work. How do you draft a case? How do you research a case? It is an incredibly complicated process. And so it's not a simple ChatGPT prompt or a simple Claude request. And that was something that came up a lot during our Series D process, something that our investors at Excel, who are really close to the Anthropic team, researched quite thoroughly. And at the end of the day, we came out on top.
3:57 Speaker 01 And we're really grateful for our partnership with Anthropic. And we feel really good about the fact that we are the cutting-edge leading platform.
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5:50 David Weisburd? This is a good time. Full disclosure, I'm an investor in Anthropic. I'm an investor in Legora.
5:54 Speaker 01 You get to win both ways.
5:55 David Weisburd? Thank you so much for having me. I think one of the maybe underappreciated aspects as companies get big, this is the Peter Thiel-ism. When Google was small, they wanted to pretend like they were a huge company. When they were a huge company, they were worried about being seen as monopoly. So they built all these different verticals, even though none of them actually contribute their revenue. So a lot of times when these companies turn into these trillion dollar behemoths, they want to have competition in certain verticals so that they can substantiate this case to Department of Justice and that they're not truly a monopoly. So there is the synergistic aspect there.
6:27 Speaker 01 Absolutely. And we have a number of different partnership fronts with Anthropic, whether it's codevelopment, whether it's leveraging their models, whether it's evals. There's a lot of joint opportunity that we can work on together. And it's because of that close partnership that our customers benefit.
6:44 David Weisburd? So I'm sure you get this question 100 times a day. Harvey versus Legora. Why is Legora a better company?
6:49 Speaker 01 We enjoy competition. Competition is what makes any company better. We weren't the first to the space, which drives a lot of humility. The space was established before we got there, and it forced us to make a lot of hard choices. When you start a company in Sweden, the entire Swedish market is smaller than the top line of Kirkland. And that means that you have to make a lot of calculated decisions about what you build, who you partner with, who you hire. And as a result, we have operated expeditiously and efficiently to become one of the fastest-growing software companies in history.
7:31 Speaker 01 And having competition means that we need to out-innovate the rest of the space. And the results speak for themselves. We have an incredibly high win rate. We have grown at a clip that no other software company has seen. But at the end of the day, I was a swimmer in high school, and I was a competitive swimmer. And what our coach always told us is when you're finishing a race, you don't look to the left lane, you don't look to the right lane. You just focus on the wall in front of you. Because if you look in either direction, you break your stroke. And when you break your stroke, you slow down. And that 0.1 millisecond that you end up slowing down might mean the difference between winning and losing that race. And so that's something that we teach all of our Ligorans, is just focus on finishing that race as hard as you can and hitting that wall. And that's what I say about competition.
8:15 David Weisburd? I've observed this in the very top, the top 1% of founders. They love competition. If there's no competition, they invent it. Maybe you could distill why exactly competition is so good for a company.
8:26 Speaker 01 Competition is a forcing function because you want to win your customers' trust. And without competition, you are not constantly earning the right to...
8:39 Speaker 01 Get that customer's renewal or earn that customer's initial check. And they don't have another option. But I can't think of a single industry where there's one vendor and there's no other option. Every single industry has multiple options because there's a large market out there. Now, the question that we have to ask ourselves is, is this a winner take all market? Or is this a winner take most market? And we wake up every day with this concept called bludsmack, which is a Swedish term, which is you wake up with the metallic taste of blood in your mouth. And we like to live with that concept because we believe in intensity. We want to work as if there is no second place. There's only first place. We started after the market was created and we not only want to catch up, we want to surpass the rest of the market. And that means we have to out innovate.
9:24 Speaker 01 We have to out think. We have to stay close to our customers. We have to operate with a deep sense of humility. And because of that, we have done an incredible job over the last two years.
9:34 David Weisburd? I never thought about it from the point of the customer in a industry like legal. They may not want to adopt. So if there's one CEO going around from Legora telling people about the future of legal tech, they may kind of put it to the side. Now, now there's two. Now you have to make a decision. So it kind of forces this decision to make a decision on the company. And then internally, I recently listened to an interview with an early Tesla engineer. And he was begging Elon, let's raise more money. Let's, let's put some more money on the balance sheet. And Elon had offers and he's like, no, I'm starving the company on the balance sheet because I need you to be focused. There's something so focusing about competition. And although I don't think you need competition, maybe at all levels of management in order to really have that drive. If you wanted to permeate through entire culture, I think competition could be extremely useful.
10:19 Speaker 01 So I'm the CFO. You know, I, I get to make the capital decisions for the business and
10:25 Speaker 01 you can raise money and you can spend that money. Or you can raise money and have intentionality. We just raised our six $550 million Series D round. It 1.2 billion dollars of interest and that $550 million could easily have been more. But that doesn't mean we're going to spend it. We have metrics that we follow that means that we're going to continue investing in things that yield the highest ROI. We have marketing ROI metrics that we have to hit. We have payback periods that we have to hit. We have cash burn ratios that we have to hit. And we don't lower those standards just because we have more money in the bank. For us, it actually raises the bar in terms of expectations because we now have more options that we can play. We can invest in the US market. We can invest in the UK, the European market, the Australian market, the Singaporean market,
11:09 Speaker 01 and we can just play on more fronts now. And so as we scale this year from 300 headcount to 900 headcount, those are the most important investments to make. We have to invest in our talent density. The greatest asset we have are our Legorans. We don't have hardware. We don't have physical locations. We have IP that is created by our employees. And so when I think about investing, I think about hiring the greatest people on the planet, the people who have seen success before, and they can bring those best practices to our organization. So as we chart the next two years, which I think are the most critical for the legal AI sector, we can run fast, no U-turns, and execute near flawlessly.
11:52 David Weisburd? Much has been said about the Legora special culture, so much so Benchmark called it one of the most special cultures. And this was an early investor in some of the greatest companies in the last couple of generations. What makes Legora's culture so special? And how did that start?
12:05 Speaker 01 This came up a lot during the series D Round, that someone had done a reference check, said that Max is intense. And it's good intense. Well, we are intense because we have a deep sense of humility. We started out as outsiders. We're not lawyers. Max isn't a lawyer. Max is our CEO. He wasn't a lawyer. He started out as an outsider with a deep passion to solve a problem in an industry that hasn't had a lot of change in decades or hundreds of years. And so we work hard, and we're clear about that during the interview process. We go to the office five days a week. We show up every single day, and we stay late. And we don't stay late because the senior person's in the office.
12:49 Speaker 01 And then as soon as that senior person leaves, everyone else trickles out. We stay in the office, whether the senior person is or is not in the office, because there's a sense of camaraderie and community to what we do. We share ideas, whether in sales, legal engineering, engineering. We like working together. And the culture is super positive. The vibes are super high. We have very low attrition rates amongst. The company, I've worked at five companies now that have scaled to over 100 million ARR. And I will say I'm having the time of my life at Legora.
13:24 David Weisburd? Tell me about the story about how you moved out to Silicon Valley.
13:27 Speaker 01 So I've always been very entrepreneurial. I tried to start a number of companies when I was in college at Washington University in St. Louis. I ended up graduating in three years, getting my master's in finance, going down a path towards investment banking. And I ended up graduating, going to Barclays in New York. I did that for a number of years, but I felt despite being a great technical butt kicking, I'm somewhat monotonous. And it wasn't as fulfilling as I wanted it to be. And I had a desire to combine my love of entrepreneurism with investment banking. And the perfect blend of the two, to me at the time, was venture capital. And so I thought, great, I want to be a venture capitalist. And so I first tried to find a way into venture capital, but back then it was super hard. It was, who do you know?
14:12 Speaker 01 And one position would open up every three or four years at a firm. And basically the door would open up for a second and then it would close just as fast. Being an analyst in New York City, very far away from Silicon Valley, my chances of finding a job there were very slim.
14:27 Speaker 01 But what happened was I developed a thesis. One of the companies that I tried to create when I was at Washington St. Louis was a cloud storage company where you could upload your music to the cloud and then downstream it to any web-enabled device. And so I developed a thesis about the cloud in general. And there were three companies that caught my eye, Box, Dropbox, and Atlassian. I applied to all three. And I was very fortunate that I ended up getting a job at Box and
14:52 Speaker 01 made it to the final rounds, got the job. Coincidentally, the same week as my girlfriend, now wife, got a job at Twitter. And we both went back into work and we quit and we moved to Silicon Valley a few weeks later.
15:02 David Weisburd? A lot has been written about this 996 culture. I did three months at Jefferies in investment banking. Banking has a crazy culture. How would you compare these two cultures?
15:10 Speaker 01 It's really interesting that you say that. I don't notice the 996. I don't think about the 996. But if I were to add up the hours, but the hours are my hours. I choose when those hours occur and they're on my terms. And a lot of those hours are on my couch or in my bed or on my own terms. And it's very different than when I was a banker at Barclays, wearing a suit and tie, sitting at an office till 8, 9, 10 p.m. at night, typing away on a keyboard. And so I actually find it incredibly fulfilling because I dictate when those hours occur and the timeline of when the work gets done. So it's a very enjoyable 996 to me.
15:55 David Weisburd? It's flow. When you're doing something, you love it and you're doing it in a team. There's something special about working hard and long hours with a team versus siloed towards a mission. It's what people talk about working in SpaceX. They don't look at it as working 70, 80 hours a week. They're looking at it, they're on a mission and they're there to complete the mission.
16:11 Speaker 01 Sam Altman quote, like, "The days are long, but the decades are short." I don't think about the days. The weeks fly by, but yes, the days are incredibly long. There are many days that I'm at the office till 10 o'clock at night. And I have three amazing kids and an amazing, amazing wife and they're all supporting me. And they love what we do and they love the company. And Max, my amazing CEO, will often write emails to my wife and I'll say, "Thank you so much, Ellen, for lending David to me on this trip to California. We did an amazing job doing X, Y, and Z." And that's awesome. The fact that my CEO and my wife are emailing together and it's a great partnership.
16:48 David Weisburd? It's very European of him to even consider your wife in her feelings. You mentioned Sam Altman, his CFO, Sarah Fryer, is this legendary CFO. And the role of CFO has really evolved over the last, I'd say, 20 years in Silicon Valley. It used to be, literally, you would just take a CFO of a public company, put them into a startup for, quote unquote, "adult supervision." Now it's much more of an entrepreneurial role. Tell me about the role of CFO today in both Legor and also, what is the best practice for Silicon Valley CFO?
17:15 Speaker 01 We like to call it CFgo because the goal is to remove friction. The goal is to help quantify the qualitative and solve problems. It is not purely an FPNA role. It is not a finance, a budgeting role. It is a goal to remove barriers. And my day job is not predictable.
17:35 Speaker 01 And I think this is also emblematic of the fact that I'm an AI CFO. There are very few AI CFOs. So Cerify is obviously one of them at OpenAI. There are a few other companies like Runway ML, Crusoe, Abridge. But we're kind of in the first class of AI CFOs. And the problems that we're working on are problems that really haven't been worked on before. So how do you make the switch from C-based pricing to consumptive-based pricing? How do you walk up your gross margin? Because a lot of these companies depend on Anthropic or OpenAI. How do you think about token utilization? How do you think about switching models between the major LLMs? There's a whole host of problems that don't necessarily have answers. And my job and my team's job is to solve them.
18:18 Speaker 01 And I would also say that the CFO's job has enlarged to be a PM's job very recently. I get involved in all the pricing decisions for the company. I have to solve for the gross margin for every deal on a deal-by-deal basis. That used to be a PM's job, but is now a great part of the finance job. It's tying a critical part of the income statement directly to my day job. And I wouldn't have it any other way.
18:43 David Weisburd? Have you had to create new metrics, new frameworks?
18:45 Speaker 01 Oh, absolutely. Like, we look at the Dow, the Wow. We look at the gross margin on a customer basis. The level of fidelity we have on our users is unparalleled to anything I've ever seen before. When in all of my prior SaaS roles, we would just bulk look at our business. And we have to look at everything on a micro level. We look at our token utilization on an hourly basis. Because if we switch models from one model to another, it could drive up our costs $100,000. And so each decision is critical. When we decide to switch LLMs from one to another for document editing, that could be a $100,000 decision. And so the relationship between CFO and CTO has to be incredibly close.
19:28 Speaker 01 Before, one of the most important relationships was CFO and CRO. That's still super important. But I would say the CFO relationship now spans to all the different C-level executives. And I'm doing daily check-ins with all the C-levels.
19:39 David Weisburd? You're also, I think, the first CFO I've ever met that has their own fund. Tell me about your fund.
19:45 Speaker 01 Throughout my career, I've had people who have believed in me and put me forward for opportunities. And in 2015, my CEO at the time, David Ulevich, recommended me for a program called Sequoia Scouts. David Ulevich was the CEO of Open DNS. Today, he's a general partner at Andreessen Horowitz, running the American Dynamism Fund. And he is one of my best friends. But back then, he was very busy running Open DNS. That year, Open DNS ended up selling to Cisco, so he had a lot on his plate. But he was one of the original Sequoia Scouts, back when Sequoia Scouts was a secret program that there was an article written about it in the New York Times. And I was fascinated by this program.
20:30 Speaker 01 I thought it was amazing that Sequoia was arming their top CEOs with this war chest that they could write $25,000, $50,000 checks into promising startups. And because David was so busy, I would bring David different ideas for companies that he could invest in. I was a 25, 26-year-old person in Silicon Valley, and so some of my friends were starting companies. Plus, my wife at the time was going to HBS, and a number of her classmates were starting companies. And so I'd bring him different ideas. Actually, a company yesterday, Shield AI, announced their $12 billion valuation, their newest $2 billion fundraise. That's a company that I invested in for David Ulevich when he was a Sequoia Scout. What was the markup on that? A lot, a lot. I'm happy for everyone involved. And so he put me forward for the program.
21:15 Speaker 01 He actually wrote a very funny letter to Sequoia and said, "David has been helping me with Sequoia Scouts." I'd write up all of his memos for him, and he would submit it, and he would get approval, and he would make these investments. He's like, "David's been helping me with all of my Sequoia Scout investments for the last six months. Either you make him a Sequoia Scout, or I quit. And then you can make him a Sequoia Scout with my spot." And to me, this was my dream. Like, when I would run on the treadmill and envision whatever my goal was, it was to become a Sequoia Scout. I wanted to be a Sequoia Scout more than anything. And here he was. David Ulevich was advancing this opportunity for me. And Sequoia, I remember, wrote back and said, "No, no, no, don't do that, don't do that. Don't quit being a Sequoia Scout. We'll meet him." And so I got to meet Ruloff, who is amazing, just such an inspiration, such a leader. And I sat down with him for an hour.
22:00 Speaker 01 And besides being the smartest human I've ever met, at the end of the conversation, he said, "Okay, you're in. You're a Sequoia Scout." And then over the next Five, six years, I made about 70 investments. And so that allowed me to invest in seed and series A companies. But what I realized is a lot of my CFO peers were series B, series C, and series D CFOs, including my old CFO, Bert Podbear, who is the CFO of CrowdStrike. My old CFO or coworker, Jenny Saran, who became the CFO of Smartsheet. My friend, Adriel Lares, who is the CFO of Fastly. And I had all these opportunities to possibly invest in my friends. I believe in my friends, so I want to invest behind them. And so I decided to raise a fund on the side to invest in these great operators. I had gone to know in Silicon Valley.
22:43 Speaker 01 And so I set out during COVID because I had all this free time because I wasn't commuting down to Palo Alto every day. And I raised an $8 million series B, C, and D fund. And so that expanded my spectrum to invest in seed, series A, and now I can invest in B, C, and D. And so I had that full spectrum to invest in. And during COVID, I finished investing in that B, C, and D fund.
23:02 David Weisburd? If you think about VCs as the customer, although in this case, Legor is the customer, VCs are the salespeople in this round. But typically, you have VCs being the customer. What better way to understand the customer than to be one, to be in the VCs spot? If you could go back, you were at Barclays, decided to jump on a plane, move to San Francisco, took a big career rest. If you could give yourself one piece of timeless advice for a younger David at that time, what would that one time's piece of advice be?
23:29 Speaker 01 I'd warn myself, the risk of staying put. So there is a Japanese word that my father-in-law once taught me is "nuru mayu." Nuru mayu means stay in the bathtub too long. And it's a beautiful word. If you stay in the bathtub too long, you get very pruney. And I think in life, I've tried to push myself out of my comfort zone. Being at Barclays, quitting like a very established job, leaving New York, which has been my home since birth, traveling across the country. I pushed myself out of my comfort zone. I got my master's at the London School of Economics. I pushed myself out of my comfort zone. But there are tons of times that I stayed too long, whether it was in a job or in a
24:14 Speaker 01 partnership with a tech vendor.
24:19 Speaker 01 And I need to constantly think about, how is the market changing? What is my role in the market? And more recently, I'm very happy I'm at Legora. The world is changing around us and Legora is incredibly positioned for this new AI landscape. And when I think about Nuru Mayu and the risk of staying put, I think about how time is condensed. And what we used to accomplish in a year is now being accomplished in a quarter. And so what I want to bring to Legora is that concept of don't wait for tomorrow. Let's do it today.
24:59 David Weisburd? Well, thank you, David. Thank you, New York Stock Exchange, The Cube, NYC Wired. And looking forward to having this conversation in a year and seeing where you guys are at.
25:07 Speaker 01 Thank you for having me.
25:08 David Weisburd? If you found this conversation valuable, please click Follow How I Invest so that you don't miss the next episode with the world's top investors.
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