Zach Abramowitz0:00
Money is pouring into legal AI companies, but what do the best VCs actually think of this space? Hey there, I'm Zach Abramowitz and I am the Legally Disrupted on episode 48 of Legally Disrupted. I'm talking about investing in legal startups because that's something I'm kind of back to doing. So, after initially pausing my investments in legal AI after ChatGPT launched, I've been back at it recently. So earlier this year I invested in Sandstone. That company is growing rocket speed. And I'm actively evaluating several other deals.
Now when I asked Jonathan Levy from Y Combinator last year about why YC was investing in more legal companies, I said, 'Does this have to do with the vertical?' And he said, 'No, we don't really care about verticals, right? What we care about is super top talented teams. We're like the NBA draft. We just go for the best entrepreneurs, best athlete on the board.' And he said that right now it is the case that the top entrepreneurs, the top startup founders want to build something in legal.
Now, I've certainly seen this firsthand like top talent is flocking to legal. Look no further than Harvey and Lora, right? But it's not just them. This entire space is attracting a different kind of entrepreneur. Trust me, I've been following the space for a long time, there is a significant and very noticeable upgrade. And honestly, I've got some FOMO, right? If I've been looking at this space for years and now all of a sudden it gets flooded with top teams, you think I don't want to invest? Of course not. I don't want to be the guy who's been looking at legal tech and evaluating it for years, knows all the teams, knows all the crevice, knows all the customers. Sounds like a flex. It is. But I also now have some serious FOMO.
At the same time, this is a dangerous game. Like right now, it's true like the product capability has never been better, but it's also never been easier to replicate these products. You know, before it was acquired by xAI, Cursor was already being pronounced dead in some circles and they had billions in ARR and a customer base that absolutely loved them. You can't talk to devs over the last year without them raving about Cursor. Now, what does that mean then for application layer companies like Harvey and like Lora, especially as Claude, which is the model of the month, gains serious traction and lawyer attention, right?
We've already seen litigators building incredibly powerful proprietary systems directly on top of base models like Claude. By the way, Quinn Emanuel has now been talking about their Claude product. We just saw Freshfields announce that they're rolling out Anthropic licenses to their entire team. So like on the one hand, yes, the teams have never been better, but that also means the competition is stiffer and the stakes are huge with legal AI startups raising eyewatering amounts of cash and getting valuations that we've simply never seen in this sector.
To break all this down and kind of get inside the mind of like how an elite VC is looking at this, today I'm talking with Keith Rabois, a managing director at Coastal Ventures and one of the most successful founders, angels, and VCs of the last 25 years. He's a founder of OpenDoor. He was also an early investor in YouTube, Lyft, Eventbrite, Palantir, like his angels as an angel. By the way, fun fact, Keith was also a litigator at Sullivan and Cromwell and a clerk on the Fifth Circuit Court of Appeals.
So, we discussed number one, why he invested in Spellbook, one of the fastest growing legal AI companies, why he's not an investor in Harvey and Lora, why you're seeing top VCs suddenly pouring money into this space, and because Keith doesn't shy away from politics or sharing his opinion, I asked him about his prediction that the Iran war would finish in just 4 days, where he comes out on the Dwarakish Jensen Wang podcast, and whether the Trump administration is getting good advice on AI. So without further ado, let's get disrupted.
So Keith, really excited to talk to you about this space. First of all, I noticed, you know, and doing a little bit of research on you, I actually didn't know this, that you were an attorney at a major AmLaw 100 firm. How long did that legal career last?