Hey there, I’m Zach Abramowitz and I am Legally Disrupted, and I’m back on the road.

Before I left my studio, I recorded several podcasts, the first of which was with Will Chen. Attention is All You Need is the foundational paper about LLM architecture. But, it has also been descriptive of a major challenge in a noisy space that’s moving fast: there’s a premium put on standing out and the ability to capture attention. Will has done exactly that.

There are two things about Will’s recent notoriety that are deeply interesting to me:

1. Building and releasing a product is a new way to gain attention in legal. That’s super new. While most critics stop at tweeting or posting cringy safeposts on LinkedIn, Will actually used “vibe coding” tools to build a functioning application layer in just two weeks.

2. Taking aim at Harvey and Legora specifically. Right now, lawyer attention has been on Harvey vs. Legora with lawyers questioning both “which tool should we buy” as well as “should we build our own.” By building an open source version, Will was able to tap into the two questions lawyers are paying attention to the most and demystify both by showing, not telling.

In this episode, we talk about his goal in building the product, the news that Kirkland & Ellis is setting aside $500 million to invest in their own AI as well as Will’s advice for lawyers and law firms who want to start building AI.

My take: I don’t find myself agreeing with Will’s level of critique for Harvey and Legora. I have much more conviction that these two businesses have massive upside beyond their current valuations and have been executing at very high levels. I also reject the idea that Harvey and Legora have plans to pull the rug out from under their customers and turn into an AI first law firm.

But, I’m still impressed and intrigued by folks like Will or Jamie Tso and Raymond Sun from Legal Quants as well as the wave of other lawyer builders that aren’t content to buy off the shelf products.

Whether you’re building or buying or just trying to keep up, the podcast with Will is a great way to get further AI-pilled. If you’re into the audio only experience, you can get listen to our conversation on Apple Podcasts or on Spotify. Another way to stay ahead would be subscribing to this newsletter. Episode 52 should be out in the next day or so.

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X is an amazing place to stay ahead on AI, so consider following me there.

If you’re more of a LinkedIn type, follow Killer Whale Strategies on LinkedIn.

“Thanks,” I said, “here’s the thing though — and I don’t mean to sound like an arrogant prick — but sales are not really my challenge.”

My inviter was taken aback. “So then, what is your biggest challenge?” they asked.

I replied, “Staying 6 months ahead of everyone else.”

Hey there, I’m Zach Abramowitz and I am Legally Disrupted! If you want to know what that little tête-à-tête has to do with Winston Weinberg and Harvey, keep scrolling. If you just want 🎙️Episode 50 of Zach Abramowitz is Legally Disrupted injected straight into your veins, I feel you, so go ahead and click play.

One of the things that we talked about in this wide ranging conversation was the importance as well the challenge of looking six months ahead. No one understands that better than the team at Harvey. Gabe’s proximity to transformer models from his time at Google, Winston’s proximity to the law from his stint at O’Melveny and their proximity to each other gave Harvey a six month head start. So when I was playing around with ChatGPT in December of 2022 and having my mind blown, the guys at Harvey had already seen GPT 4.0. And it’s not just about what tools they had. It’s that access to the models allowed them to start wrapping their heads around AI and all of its implications. Early adoption compounds, so does being first. As Winston said in the podcast, they have had plenty of time to make mistakes and learn from failure.

And, as a result, sales at Harvey are not their biggest challenge at the moment.

The biggest challenge at Harvey is planning for what’s coming six months down the line: model breakthroughs, changing user behavior (e.g. can’t we just build this in Claude?), new market entrants, token pricing and scaling compute, just to name a few.

Staying ahead is the challenge for anyone in this market, whether you’re an $11B company like Harvey or whether you’re someone like me who is advising companies on AI strategy. No one is going to pay the Killer Whale Strategies team for strategic advice if we don’t stay at least six months ahead.

If you are interested in staying ahead, the podcast with Winston is a great place to start. If you’re into the audio only experience, you can get listen to our conversation on Apple Podcasts or on Spotify. Another way to stay ahead would be subscribing to this newsletter.

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Why should you be only the one to stay ahead? Do the right thing and share this post with someone who is in deep need of some good old fashioned legal disruption.

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This wasn’t my most viewed tweet of the week, but it was certainly my favorite.

You can also stay in touch by connecting with me or following Killer Whale Strategies on LinkedIn.

Hey there, I’m Zach Abramowitz and I’m Legally Disrupted, and the podcasts are coming in hot just in time for summer.

Frequent readers of this newsletter know that, in addition to Zach Abramowitz is Legally Disrupted, I also co-host the AAAi Podcast with Bridget McCormack, President and CEO of the American Arbitration Association and former Chief Justice of the Michigan Supreme Court. The goal of the podcast is to introduce the AAA’s audience to some of the most interesting builders, thinkers, and operators shaping the future of legal AI.

Over the last two and a half years, we’ve hosted guests including Richard Susskind, David Lat, Darth Vaughn, Whitney Stefko Dover, and many others. Just as importantly, the podcast also gives listeners a window into the AAA’s own transformation as it positions itself at the center of the future of dispute resolution.

Our conversation with Ariel Deshe from TrialKit.ai stood out because it highlighted something that still isn’t discussed enough in legal AI: there’s a big difference between building AI for a lawyer and building AI for a law firm.

Ariel explains in the podcast how a particular criminal case exposed a core problem in modern litigation: the sheer volume of digital evidence had become impossible for small defense teams to process effectively. Months later, he left public defense and started TrialKit to solve that problem.

That’s what makes the company interesting.

For years, prosecutors had access to increasingly sophisticated investigative and forensic technology while many defense attorneys lacked the resources to keep up. Since the rise of tools like Cellebrite, the imbalance has only grown more pronounced. TrialKit represents something different: for the first time in years, many criminal defense lawyers are finally gaining access to tools powerful enough to help level the playing field at a price point they can actually afford.

The broader point here matters.

One of the persistent myths about AI is that it only works for large enterprises with giant budgets. TrialKit is evidence that AI can also expand access to high-quality legal work for smaller firms and solo practitioners. In that sense, access to justice no longer has to mean “doing more with less.” It can mean giving lawyers better tools in the first place.

AI will not reshape the legal system all at once. It will happen lawyer by lawyer, workflow by workflow, and case by case — especially among practitioners who historically had the fewest resources. That’s part of what makes this moment in legal tech so fascinating. Subscribe to the AAAi podcast if you haven’t already — you can also subscribe on Apple Podcasts and Spotify.

Another very good idea (if I may say so myself) is to subscribe to this newsletter. I’ll be writing about Episode 50 of Zach Abramowitz is Legally Disrupted later this week plus there is more legally disruptive content is on the way.

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You can also connect with me on LinkedIn if that’s your thing.

Hey there, I’m Zach Abramowitz and I am Legally Disrupted. And, I am still dragging a bit from a long road trip and, like Willie Nelson, I’m about to be on the road again.

Lately, I’ve noticed a pattern. Law firms are incredibly obsessed with how they should be using AI. They are focused on buying the right tools, tracking adoption rates, and training associates on platforms like Harvey or Legora. But they aren’t spending nearly enough time asking what their business needs to actually become now that AI exists.

For example, what happens when your top-tier lawyers master these AI tools, connect the dots, and realize they don’t actually need the massive Big Law infrastructure to build a highly lucrative practice?

Well, we don’t have to guess. On episode 49 of the podcast, I sat down with Logan Brown, who followed that exact journey.

Logan was an associate at Cooley using Harvey when she realized there was an entirely new business model waiting to be built to service an untapped market of early-stage startups. She left to found Soxton.ai, an AI-first law firm that acts as an outside, AI-powered GC.

Instead of the traditional billable hour, they charge flat fees like $100 for a contract review or $50 to ask a lawyer a quick question via chat. She’s already got over 40 attorneys on the platform. And in a departure from the traditional partnership track, she actually chose to raise venture capital so she could scale the firm like a tech company and tackle the access-to-justice gap.

Naturally, not everyone is thrilled about this disruption. Since coming out of stealth, Logan has been receiving a surge of hate mail from existing lawyers, including a Biglaw partner who emails her once a month just to tell her how horrible she is. Despite the blowback, Logan is making a massive bet on the AI-first model, predicting that in five years, traditional Big Law firms will be looked at like the Yellow Pages.

I’m not sure I agree. And I think you’re more likely to come to that conclusion if you’ve been an associate but not a partner — especially a rainmaker. But I do think the AI first firms have a compelling proposition. I’m also biased. Many of the AmLaw 200 firms are clients of mine, and I specifically am working with them on staying current and not turning into the Yellow Pages. But, Logan was a great guest and a lot of lawyers who are thinking about stating or converting a practice into “AI first” will find this conversation really useful.

Make sure you subscribe to the podcast on YouTube, Apple, Spotify, or wherever you get your podcasts. Subscribing to this newsletter is also a really good idea.

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This wasn’t my most popular post on X this week, but it was my personal favorite. I’m still giggling over it. And yes, I frequently laugh at my own jokes.

Hey there, I’m Zach Abramowitz and I am Legally Disrupted. I’m finally back home from an 11-day road trip with stops in Colorado for ILTA EVOLVE, followed by Arizona, Napa, Reno, San Francisco, Los Angeles, and everywhere in between. It was great to be on the road and get the opportunity to meet so many of you, and I should have an update soon on my next “in-personing.”

Now, back to investing in Legal AI startups.

After hitting pause on legal AI investments right after ChatGPT launched, I’ve been jumping back in. Earlier this year, I invested in Sandstone (which is already showing hockey stick growth), I’m actively evaluating several other deals, and frankly, I have some serious FOMO. When I spoke to Jonathan Levy from Y Combinator last year, he told me YC doesn’t invest in verticals, they invest in the best talent. And right now, the absolute top startup talent is flocking to legal.

But it is a dangerous game out there. Yes, the products are incredible, but they’ve also never been easier to replicate, as I showed on stage at ILTA EVOLVE this week:

Just look at Cursor. Even before its acquisition by SpaceX, people were already declaring it dead despite billions in revenue because of the rapid improvement of base models like Claude Code. So what does that mean for application-layer legal companies like Harvey and Legora, especially when we’re seeing litigators at firms like Quinn Emanuel bypassing them entirely to build proprietary tools directly on top of Claude?

To figure out where the smart money is actually going, I sat down with Keith Rabois on 🎙️ episode 48 of Zach Abramowitz is Legally Disrupted. Keith who is a Managing Director at Khosla Ventures, is one of the most successful investors of the last 25 years, and, fun fact, a former litigator at Sullivan & Cromwell who clerked on the Fifth Circuit.

Keith does not pull his punches. We dug into why he is emphatically not an investor in Harvey or Legora. His contrarian take? Trying to improve the productivity of the AmLaw 100 runs completely counter to their bill-by-the-hour business model, which will just lead to fee compression rather than a massive new market. You’ll have to listen to the podcast to see which previously hot startup reminds him of Harvey.

To be fair, Keith does have a horse in this race as an investor in Spellbook. But he distinguishes Spellbook from Harvey because he doesn’t see Spellbook as #legaltech; he sees Spellbook as contract tech.

And because it’s Keith, we didn’t just stick to legal tech. We got into his prediction that the Iran conflict would be over in just three days, the massive economic boom happening in Latin America, and why he strongly disagrees with Nvidia CEO Jensen Huang about chip export controls. In fact, Keith points to the recent crash of DeepSeek as a prime example that American export controls are working exactly as intended.

It’s a fascinating, unfiltered conversation that you do not want to miss. Podcast 49 with Soxton founder and CEO Logan Brown drops this week as will podcast #50 with a very special mystery guest. So make sure to subscribe on YouTube, Apple, Spotify, or wherever you get your podcasts. Another very good option is subscribing to this newsletter.

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Tweet of the week:

Hey there, I’m Zach Abramowitz and I am Legally Disrupted. It was lovely getting to meet so many folks in person at ILTA EVOLVE and elsewhere who subscribe (or now subscribe) to the newsletter.

Speaking of lovely, right before I hit the road this week, I sat down with my pal Richard Tromans from Artificial Lawyer for another Excellent Legal AI adventure. And right now, lawyers want to know about Claude for legal.

We went deep on whether Claude is going to steal Harvey and Legora’s lunch. We are already seeing top-tier litigators bypass off-the-shelf products to build directly on base models. For example, Quinn Emanuel built their own proprietary system (the “Kerch Bench”) entirely on top of Claude. Instead of relying on an application-layer company, they are structuring their own case data, distilling depositions, and building custom Claude “skills” to draft briefs and conduct early case assessments. If litigators can achieve an order-of-magnitude productivity gain just by directly prompting Claude as a thought partner, what does that mean for companies like Harvey and Legora?

We also unpacked Freshfields’ announcement that they’re partnering with Google, followed by their announcement that they’re partnering with Anthropic. We talked about why someone would use Claude for legal workflows, both if they’re in a law firm or an in-house legal department.

We also got into the recent buzz about suspicious ARR numbers and bookkeeping by some startups. And finally, we discussed why lawyers are blowing AI hallucinations out of proportion. As we’ve discussed before on this show, human lawyers and judges hallucinate all the time. In fact, the entire appellate court system is predicated on the fact that humans make errors and hallucinate facts or law, which is exactly why we need a system to correct them.

Since I’m on the road, I’m a bit behind with updates on the podcast, but if you can keep a secret, episode 48 with legendary startup investor, founder, operator and currently Khosla Ventures MD Keith Rabois is out as well. Episode 49 with AI First firm Soxton.ai founder Logan Brown will be out this week as well (and that one was super fun). So make sure you subscribe to the podcast on YouTube, Apple, Spotify or wherever you get your podcasts. Subscribing to this newsletter is also a really good idea.

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Hey there, I’m Zach Abramowitz and I am Legally Disrupted.

In 2025, one of the biggest trends we tracked was the widespread adoption of AI by lawyers. According to a spat of surveys from Wharton, Law360, Thomson Reuters, and the ACC, AI usage in the legal profession officially flipped from a minority to a clear majority.

But in the courts, AI has been something of a blooper reel. Just this week, a prestigious litigation partner at Sullivan & Cromwell had to grovel before the court about an emergency motion the firm submitted that was filled, nay riddled, with AI hallucinations.

This brings us to an admitted, glaring double standard between lawyers and judges. Lawyers are totally fine with lawyers using AI, but those same lawyers become apoplectic at the thought of judges or arbitrators using AI. It is very much “AI for me, but not for thee.” A survey last year from White & Case and Queen Mary University of London School of Law showed that nearly 90% of lawyers were deeply supportive of AI for their own research and analytics, but that support drops to just 23% when it comes to a judge or arbitrator using it to make a decision.

It’s not just vibes, there is also a regulatory double standard. Under Annex 3 of the EU AI Act, AI used in the administration of justice or alternative dispute resolution is explicitly classified as “high-risk,” and requires different disclosures than ordinary AI use cases.

So, what is really going on here? This isn’t just about the law; it is about public sentiment towards AI. For the last few years, we’ve been taught that AI is just a “copilot” or a helper. But now, in 2026, we’re talking about AI acting as an agent that takes actions and makes decisions. Giving a machine that kind of power is anxiety producing, and most people want products that are anxiety reducing.

Yet, despite that hullabaloo, there is a massive need for alternative forms of intelligence in our courts. Right now, the system is drowning. We have state court trial judges disposing of 2,500 cases a year, meaning they have barely half an hour to spend on a single case. We are simply not going to lawyer our way out of this 50-year backlog. If we just use humans, we have a massive demand for intelligence but a severely limited supply. AI could step in to give these judges the capacity they desperately need for the courts to actually function.

Now, skeptics will say, “But what we must preserve the human element.” Do we, though? I thought Lady Justice is blind. Think about that. We explicitly acknowledge that judges can’t be too human because the “too human” part gets in the way of making a fair, unbiased decision. Plus, human judges make plenty of mistakes, which is exactly why our entire system requires appellate courts to correct them.

The two people who understand this better than anyone else are my guests on Episode 🎙️ 46 of Legally Disrupted: Shlomo Klapper and Bridget McCormack. Shlomo is the founder of Learned Hand, which is building an AI decision-support tool specifically designed to give judges that desperately needed capacity. Bridget is the former Chief Justice of the Michigan State Supreme Court, who is now the CEO and President of the American Arbitration Association. (And by the way, Bridget and I cohost the AAAi Podcast, so make sure to check that out!). You can watch the full episode right here in the embedded link.

If you prefer your podcasts in audio find Zach Abramowitz is Legally Disrupted on Apple and Spotify. Subscribe to this newsletter is also highly recommended, especially by me!

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Want to be disrupted in person? Come see me in Colorado next week, I’ll be the opening keynote at ILTA EVOLVE. A number of readers have already reached out to let me know they will be there. If you have plans to attend, please make sure to find me.

PS AI for legal talk on X has new life. You may be missing out. Here’s the X post of the week to entice you. Click it and come join the conversation.

Hey there I’m Zach Abramowitz and I’m Legally Disrupted! Happy Easter 🐇 for those celebrating.

Today I want AI to give you a better job. That’s why I invited Kyle Poe, the VP of Legal Innovation and Strategy at Legora, to be a guest on the podcast last week. He is uniquely credible on this topic.

Kyle is a Harvard Law grad who spent over a decade at Morgan Lewis, where he eventually made partner. But that’s not why Legora hired him. Early in his career (and long before it was a popular career track) he was partnering with his firm’s IT department to build a custom matter management platform.

When ChatGPT launched, Kyle realized the ultimate paradigm shift had arrived: computers had finally learned to speak language. He knew he had to go all-in on AI, which eventually led him to Legora.

In 🎙️Episode 45 of Zach Abramowitz is Legally Disrupted, Kyle and dive into why building tech workflows and writing AI prompts should absolutely be considered billable work. We also explore why AI commoditizing the legal “grinders” and “minders” means old-school social skills are about to become your single biggest competitive advantage. Finally, Kyle goes into great detail about how exactly how he landed a top role at Legora and how others can do the same (hint: merely dropping your resume into a web portal is not enough).

If you prefer your podcasts in audio find Zach Abramowitz is Legally Disrupted on Apple and Spotify. I also approve of those who choose to subscribe to this newsletter.

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If you’ve been pod-binging Legally Disrupted to help you get a job in legal AI or for any other reason then I’d like to hear from you. Get in touch by replying to this email. And, finally, please enjoy the tweet of the week:

Hey there, I’m Zach Abramowitz and I am Legally Disrupted here with your boiling hot cup of Sunday disruption.

Josh is a personal injury attorney who started his own firm with a partner right out of law school. Over the years, his firm became massively successful, even cementing a unique niche as the go-to dog bite lawyers in the state of Maryland. But as the firm grew, they hit a major bottleneck: reading and analyzing unstructured medical records was slowing down their ability to take on more cases.

When ChatGPT launched, Josh and his brother Jeremy realized large language models could completely change the game. They built LawPro.ai, which has now been serving personal injury firms for about two and a half years. It’s also had a profound impact on his firm Zirkin & Schmerling Naturally, I had to bring him on for 🎙️Episode 44 of Zach Abramowitz is Legally Disrupted.

The results speak for themselves: prepping for an expert deposition used to take Josh hours, but with his own product, it now takes him just 15 to 20 minutes. Because AI handles the drudgery of document review, paralegals and case managers have more time to actually speak with clients, resulting in happier clients, more repeat business, and increased referrals. We also discussed the results of a massive new study LawPro.ai conducted with Morgan & Morgan, which found that 92% of personal injury law firms are now using some form of AI.

Finally, we got into a major trend that many law firm owners are trying to ignore: Private Equity is coming to the legal space. Josh shares his mental model for why firms need to implement AI now to improve their EBITDA, making them capable of either competing against PE-backed behemoths or becoming highly attractive buyout targets themselves.

So grab a hot beverage, and treat yourself to a dose of Sunday disruption by watching the embedded YouTube link or find Zach Abramowitz is Legally Disrupted on Apple and Spotify.

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Would you like to be legally disrupted in person? I will be keynoting the upcoming ILTA EVOLVE conference in Colorado April 30-May 2, and you can learn about the agenda and register here. I always try to prioritize newsletter subscribers, so let me know if you’re planning to attend and we can meet up.

Also, make sure to follow me on X for zingers like this one

Hey there, I’m Zach Abramowitz and I am Legally Disrupted!

If you remember back to Episode 37, I talked about how I had invested in Sandstone. Investing in AI startups now is risky as hell, but if there’s a team that’s going to figure it out, it’s the Sandstone crew. They recently picked up a big check from Sequoia Capital and SV Angel and have been adding top talent to their team. Right before I recorded this conversation, Sandstone co-founder Jarryd Strydom had just gotten back from a cross-country road trip hitting up California, Seattle, and Texas just to sit down with in-house counsels and get a real pulse on the market.

Naturally, I had to bring him on to debrief for 🎙️Episode 43 of Zach Abramowitz is Legally Disrupted. We covered a lot of ground in this episode, diving into why legacy CLMs are drifting away because they require lawyers to work for the tool, rather than the tool working for them. We also talked about how AI is finally giving in-house teams the infrastructure they need to shift from reactive risk mitigation to proactive commercial strategists.

We also got into a massive vibe shift: Jarryd’s impression is that over 50% of the in-house market is now actively paying attention to AI and many are even “vibe coding.” Jarryd and I discussed the C-suite mandates pushing legal to keep up with the speed of sales and engineering, and how AI might actually revive the “Renaissance man” model for junior lawyers by allowing them to act as true legal generalists.

So, grab a hot beverage, curl up on the furniture piece of your liking and treat yourself to a dose of Sunday disruption by watching the embedded YouTube link or find Zach Abramowitz is Legally Disrupted on Apple and Spotify.

Episode 44 with Josh Schmerling from LawPro.ai has already been recorded and will drop soon as has Episode 45 with Learned Hand founder Shlomo Klapper and AAA President and CEO Bridget McCormack on AI as a judicial decision maker. So, make sure to subscribe to the podcast or follow the Legally Disrupted YouTube channel. Subscribing to this newsletter is also a good idea.

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Would you like to be legally disrupted in person? I will be keynoting the upcoming ILTA EVOLVE conference in Colorado April 30-May 2, and you can learn about the agenda and register here. I always try to prioritize newsletter subscribers, so let me know if you’re planning to attend and we can meet up.

Hey there, I’m Zach Abramowitz and I am Legally Disrupted! And my head is still spinning from an action-packed Legalweek. Before Legalweek, I recorded a conversation with one of my absolute favorite people in the industry.

In addition to this newsletter, our team regularly briefs clients about AI and the state of the market. But, ultimately, our content is only as good as our sources. One of my trusted insider sources is Cosmonauts founder Timo Karakashev. Timo runs conferences all over the world, giving him a front-row seat to exactly what both buyers and sellers are thinking and what they are actually adopting.

A big part of my podcast push over the last six months has been to open source our research process. So, naturally, I had to bring Timo on for 🎙️Episode 42 of Zach Abramowitz is Legally Disrupted. We covered massive ground in this episode, trying to figure out if the AI space will continue this same crazy growth trajectory. We also dove into why the intellectual property market feels about three years behind the rest of the industry, and why so many legal teams are complaining about Microsoft Copilot (Timo’s blunt take: “because it’s shit”) while praising alternative tools like Gemini. We also discussed the massive, untapped opportunity in building AI tools for the business and operations of law firms, rather than just focusing exclusively on the practice of law. I’ve been aiming to release newsletters every Sunday morning Eastern Time, so you can schedule your disruption like clockwork. This week, however, with travel and work getting particularly hectic, I had to push to Tuesday evening. So, if your week has felt off balance since Sunday, please accept my apologies and this fresh, new episode to set things right.

Episodes 43 (Jarryd from Sandstone) and 44 (Josh from LawPro.ai) have already been recorded and will drop soon, so make sure to follow the podcast on Apple/Spotify and/or the Legally Disrupted YouTube channel. Subscribing to this newsletter is also a good idea.

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Would you like to meet and hear me in person? I will be keynoting the upcoming ILTA EVOLVE conference in Colorado April 30-May 2, and you can learn about the agenda and register here. I always try to prioritize newsletter subscribers, so let me know if you’re planning to attend and we can meet up.

The final stanza reads:

Then sitting there in the cold dark air, he started to nibble his feet,
Then his legs, then his hips then his neck, then his lips
Till he sat there just gnashin' his teeth
'Cause nothin' was nothin' was nothin' was nothin' was nothin' was left to eat.

Hey there, I’m Zach Abramowitz and I am Legally Disrupted! And I’m starting to think that AI has an overeating problem. Prediction-flex alert: all the way back in March of 2023 and long before SaaSpocalypse, I wrote about AI replacing incumbent #legaltech software.

But it’s really getting out of hand these days as AI begins, like Hungry Mungry, to eat itself. The AI application layer has always been threatened by the foundation model. But the vibe is beginning to shift.

Maybe the out of the box model cannot do what the fancier legal application does, but what if a lawyer could simply code those features themselves? What if they could make it look and feel exactly like they wanted it to.

The new poster child of “Code it yourself counsel!” is Jamie Tso, the Hong Kong based lawyer and founder of the Legal Quants community who began replicating features of some of well known legal AI tools and open sourcing them. Other lawyers began taking inspiration from Jamie, something we began immediately flagging to KWS clients.

I reached out to Jamie on LinkedIn late last year to learn more about what he was doing. Crickets.

But the joke is on him because that just made me more interested.

Since then, this series of LinkedIn posts has blossomed into a highly exclusive community of over a hundred lawyer coders called Legal Quants. Finally, after some mild begging polite nudging, I was able to connect with Jamie and get him on the podcast with Legal Quants founder Raymond Sun. I learned during this conversation about the secret WhatsApp group that is home to this grassroots community (my request for admission was of course denied). Several listeners reached out to tell me that I sound giddy in this podcast. They’re right, I am giddy. That’s why we went close to an hour and a half in this episode. Jamie and Ray have real conviction about where the AI train is headed, namely that “The cost of developing software applications is going to zero.” They also have an open and creative mind about what that will mean for the profession. This is serious AI 2.0 second order effects thinking, and I’m here for it all. So grab a hot beverage, and before anyone else wakes up, treat yourself to a dose of Sunday disruption by watching the embedded YouTube link or find Zach Abramowitz is Legally Disrupted on Apple and Spotify.

Podcast 42 (Timo from Cosmonauts), 43 (Jarryd from Sandstone) and 44 (Josh from LawPro.ai have already been recorded and will drop soon, so subscribe to the podcast or follow the Legally Disrupted YouTube channel. Our audience on YouTube alone has grown by over 200% since September and more than doubled since November. Subscribing to this newsletter is another good way to keep up with the content.

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Hey there, I’m Zach Abramowitz and I’m Legally Disrupted.

Whenever I bump into Damien at a conference (or on redeye flight), he always has a unique take on the market to share. I always leave the interaction thinking “Man, I wish I had been recording that.” That’s why I decided to bring him on for 🎙️Episode 40 of Zach Abramowitz is Legally Disrupted. We got right down to it, discussing why we haven’t actually hit the peak of profitability for lawyers just yet. He argues that the law firms and lawyers who decouple time from value and shift from hourly billing to flat fees are going to make significantly more money. I think we could be headed for a $10,000 billable hour before we see the elimination of the billable hour.

In the course of our discussion, we also dove into why in-house counsel is currently ahead of law firms when it comes to AI adoption, and how the combination of AI-first law firms, Arizona Alternative Business Structures (ABS), and the removal of ABA accreditation moats in Texas and Florida are setting the stage for massive disruption. We also explored the wild future of plaintiff bots battling defense bots, and why the “humanity” of rainmaking will remain the ultimate competitive advantage for lawyers.

Episode 41 with Jamie Tso and Raymond Sun from Legal Quants drops early this week so make sure to subscribe on YouTube, Apple Podcasts and/or Spotify. Subscribing to the newsletter will also work.

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The folks leading AI rollouts are going to start getting questions about impact and ROI. Just falling back on adoption metrics isn’t going to be enough in the current AI zeitgeist (the “zAItgAIst”). Which is why I would encourage folks to listen 🎙️episode 39 of Zach Abramowitz is Legally Disrupted with Ivo founder Min-Kyu Jung. Ivo has seen exponential growth and counts brand names like Uber, Pinterest and Reddit amongst its customer base. In the course of our discussion, he outlined an interesting framework for measuring different dimensions of ROI that, while intended for in-house legal, serves as a good starting point for just about any business. We also talked about how he had to pivot hard when LLMs emerged and how he’s thinking about current threats to AI startups and legacy companies.

Episodes 40 and 41 are in the queue so make sure to subscribe on YouTube, Apple Podcasts and/or Spotify. Subscribing to the newsletter will also work.

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Hey there I’m Zach Abramowitz and I’m Legally Disrupted. And it’s been a minute.

In the coming weeks, I will share how I’ve been investing more energy into video podcasts, why I’m doubling and tripling down on this format and how that will show up in this newsletter and everything else I do. What I will say now is that we are starting to feel really good about the content and we are already seeing it in the data. Audience and subscribers have started to grow organically and more importantly, people really like it. Some are reaching out to me and telling me how much they enjoy the podcasts (especially on YouTube) and how it has helped them separate signal from noise. Others frequently tell me they are preparing for interviews for law firm/in-house AI roles as well as startups by binging my podcast, and it’s working. Others (from C-suite down to the front line) are using it to learn about which products they should be demoing or trying to replicate in Google AI Studio. Some people (cough, cough CLM companies) get in touch to challenge one of my takes. And I appreciate all of it.

But, the thing we are hearing the most is that people laugh when they listen, including unconfirmed reports of beverages going through the nose (our most important KPI).

If AI-first soda-snorting laughter sounds like something you need in your life, then I encourage you to subscribe on YouTube or find us on Apple Podcasts and Spotify. Search “Zach Abramowitz” and/or “Legally Disrupted” on your app and we’ll come up.

Scott and I went deep for nearly an hour, and it was one of my favorite episodes to date. In addition to challenging the Harvey/Legora narrative, we talked Claude for Legal, SaaSpocalypse, the advantage of selling direct to lawyer, the risk of AI to software startups, the reason evals are BS, the real metric to measure and the number of talented teams (all human) entering the AI for legal market. Shout outs in the episode to Jonathan Levy from YC plus the folks at Sandstone, TrialKit and Learned Hand.

One of the ways you can keep up with select content from YouTube and my podcasts is by subscribing to this newsletter. You won’t get everything you would get by also subscribing on YouTube, Apple and Spotify, but you will get some of the key highlights.

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**Note to Readers: critical rant incoming. If you want to skip down to where I talk about the Reddit thread, I won’t be deeply insulted. But, just know you’re missing out.**

</START RANT>

I feel like I need to make this clear because a number of people have asked me directly whether I’m getting paid by Harvey or if I have some relationship with them. When I’ve mentioned it to others in my network, their reaction is usually “Yeah, I thought that too, but I didn’t want to say anything.” My guess is that some of you have come to that conclusion as well.

So, let me be quite plain: I don’t get paid by Harvey. I have never been paid by Harvey. I own zero stock in Harvey or any SPVs that have invested in Harvey.

The fact that I’m not on the dole from Harvey is important, in particular, for today’s dose of legal disruption because I’m going to get into the now vaunted Reddit thread in which someone purporting to be a recently fired Harvey employee decided to go nuclear (the post has since been deleted). In the course of discussing the content of that thread, I might end up defending or, Heaven forefend, even saying something nice about Harvey. But, I need to go on this rant not just over the Reddit thread but because it is fundamental to the Killer Whale Strategies business model.

I’m an aligned incentives extremist. I never want clients wondering if I’m recommending a tool because I get a kickback. Early in my career I tried referrals, and it felt queasy and totally off-brand for what we do now at KWS. Our value is often in saying the hard-to-hear stuff, and that only works if clients know we’re focused solely on their long-term success.

That said, to be in the dealmaking business, you need some skin in the game. That’s why I invest my own personal money in legal startups. It signals confidence, shows clients I understand what’s coming, and gives me insight you can’t get from the outside.

Sometimes I recommend portfolio companies to clients — but only when the ROI is undeniable. Other times I don’t. And the value I provide to clients has actually increased because I see both sides of the table: the Davids and the Goliaths. That dual empathy makes me a better advisor.

Furthermore, the value we provide to clients has increased dramatically from my experience as an operator-investor. Investing in and helping startup founders is like the gym work that gives me an edge on the field of client services. By sitting on all sides of the table and getting into the weeds with a handful of top teams, I’m able to get unique insights about the ecosystem. It’s given me a kind of two-sided empathy, and that’s made me a better dealmaker and strategic advisor. I understand the mindset of the Davids and Goliaths because I work with both.

The only startups I have ever worked with on retainer are the ones with whom I’ve invested, and that’s only after a cool off period following my initial investment. Every startup CEO I invest with will tell you that as part of my investment with them, I give them strategic counsel and coaching, not just after I invest but while I’m evaluating them.

And I don’t charge them anything for it.

During the evaluation process, I open doors for them with clients for whom there could be a fit. KWS clients see this is a major value add, because it often means they’re seeing hot companies before the rest of the market. In some cases, these intros have led to huge deals for both sides. I introduced Baker McKenzie to SparkBeyond before they launched an exclusive partnership; I helped TermScout secure investments from James Currier at NFX and David Stark at Ground Up Ventures; I introduced LegalMation to one of their first major automotive OEMs (they have since secured deals with more than half of the big automakers). I could go on.

In some instances, portfolio companies will ask me to dedicate more time and attention to helping them win. When the opportunity makes sense, we will do that, often in exchange for more equity, but sometimes cash. We will NEVER do it on commission. There are tech and companies outside my portfolio (but almost always mature companies) that engage us to brief them periodically throughout the year on the key trends we are seeing in the market. Harvey has done neither.

In previous newsletters, I have said unequivocally that I had never spoken with anyone from Harvey, and I even admitted to being “butt-hurt” re: the non-reach-out. In the last year, I have spoken with people from Harvey, but we’re just friends. But, listen, I am not shy. Trust me, if I had invested in Harvey, you’d know about it from my nonstop flexing. Not only do I not work for Harvey, but on at least one occasion I introduced the Legora team to a Harvey customer, hosted Legora’s head of community Chris Williams on my podcast and have plans to do the same with Max Junestrand (although we’ll have to see after this newsletter ). Plus, I’ve specifically looked at investing in companies I believe can compete with both Harvey and Legora. There are more than a few.

As a broader cultural point, we’ve become suspicious of anyone who takes a spicy position online. And, to be fair, I’ve definitely not been vanilla in my Harvey takes. I’ve written newsletters indicating that Harvey was, well, kind of awesome (something I still believe). But, in my defense how can you not be in awe of a three year old startup generating over $100M in ARR and $5B valuation based on investments from some of Sandhill road’s finest, all while making inroads with customers that were previously impenetrable for startups? That would have been impressive in its own right, but it’s even more impressive that the founders were a couple of guys in their 20s who had never launched a startup, and the one who was supposed to be the “domain expert” had only worked for six months in Biglaw.

So what do I think about Harvey?

I admire Harvey as a company and, yes, even have a bit of FOMO: I didn’t come up with the idea myself and that I didn’t invest in their seed round. For someone who’s as active in the space as I am, it was a real miss on my part. I think Harvey is a force with which to be reckoned. They have real vulnerabilities, but I think there is a strategy in place to address those vulnerabilities. Even the Death Star had that one spot.

This is one of those “Two things can be true at the same time” scenario. I can be both in awe of Harvey, as well as deeply on the lookout for the next Harvey, including investing with credible competitors, of which I believe there are a few.

I can even write these opinions publicly without Harvey being the Qatar to my Tucker Carlson.

</END RANT>

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Breaking down the Reddit thread.

Now, as far as the r/legaltech thread goes, there’s the actual content of the post, which I think is less interesting, and the reaction to the post, which I think is the real story here. So, that’s what I want to address first.

Harvey sparks some strong emotions.

Harvey gets people talking. That’s what a powerful brand does. You saw that in this instance for sure. Everyone on LinkedIn felt compelled to weigh in on this all-important AMA, as if they hadn’t just learned ten minutes ago that r/legaltech is even a thing.

Our team read the thread, but that’s because my partner Nina reads every single r/legaltech thread, despite her complaint recently that it’s become way too salesy. I honestly didn’t make much of it at first. This isn’t the first time that r/legaltech commenters dunked on Harvey (as well as other vendors).

So, now, let’s do the following mental experiment. Imagine for a moment that the r/legaltech thread had been about Legora, instead of Harvey.

Do you think every Legal Innovation Linkedfluencer would be hot-taking all over themselves to explain why they felt obligated to share their perspective on this all important thread?

Methinks not.

The Reddit thread is a byproduct of a strong brand, with some real kick.

Here’s the real story: Harvey has become the Dallas Cowboys of AI for Legal. The Cowboys are the iconic team so many love, and even more love to hate. All that energy gives the Dallas Cowboys their $13B value, $2.5B more than the next team that you don’t care about because they’re not the Dallas Cowboys.1 It doesn’t matter that they haven’t won the most Super Bowls or that they don’t have the newest stadium, their brand makes them the most valuable franchise in American sports. Given Harvey’s Dallas Cowboys vibe, it’s no surprise that they are valued more than 5x their closest competitors.

For years, ESPN’s Skip Bayless (another polarizing brand) built his audience on this dynamic. I worked at ESPN during Law School, and, amongst the other talking heads, Skip was easily the most polarizing on-air personality. But his audience made him one of the highest paid pundits both at ESPN and later at Fox. His genius was realizing two simple truths:

1. Fans either love the Cowboys or hate them.

2. What fans loved, and what haters couldn’t stand, was how much extra attention the Cowboys got.

So Skip gave them both exactly what they wanted: more Cowboys talk. He didn’t mind being hated, as long as there was love in the mix.

The reason I write about Harvey so much, is because that’s what you want to hear about, whether or not you love them or hate them (yikes! does that make me Skip Bayless of legaltech?). When I speak to lawyers and VCs, they both ask me about Harvey. When I write about Harvey, everyone shares it (as some of you surely will share this insanely long newsletter). I noticed this for the first time when my podcast with Edward Bukstel about whether Harvey was overhyped, quickly became my most downloaded episode. At this year’s ILTACON, the session on Harvey was quite literally standing room only and had the palpable buzz of a real media event. I’ve never seen anything like that at legaltech events. Legaltech has never had a brand that drove this much engagement. We’re bigtime now.

And, like the Cowboys, iconic brands can be divisive. They can even platform competitors. Almost every firm I know that has chosen Legora has mentioned to me that they were getting pressure to buy Harvey, but couldn’t stand the thought of working with “those guys.” By the way, that’s totally reasonable. But, it indicates that one of the most important reasons to buy Legora is (1) Harvey exists and (2) Legora isn’t Harvey. I think they understand this too, and it would explain why they would change the company name from Leya to Legora. Rather than have a name that puts you in the same box as Harvey, be as different from Harvey as possible.

I am willing to bet that every firm decision maker that went with Legora has been sharing the Reddit thread internally. Because, what validates their decision is not that Legora is awesome (which I’ve heard it is btw), but evidence that Harvey is now tainted.

Take Goodwin for example. Earlier this year they announced they were going with Legora, with Mary O’Carroll as the spokesperson on the release. Fast forward to her more recent LinkedIn post where, instead of talking up Legora, she pointed at Harvey and the Reddit thread.

That’s the dynamic I’m talking about and Mary, who is quite clever, knows what she is doing. Firms don’t validate their decisions by saying, “look how great Legora is.” They validate them by saying, “Look at Harvey’s shortcomings, aren’t we smart for holding out for a better option?” That’s not because there’s something wrong with Legora, it’s because Harvey is in everyone’s heads just that much.

Okay, but what about the actual claims made in the Reddit post?

The Reddit post itself didn’t tell us anything new. It was catnip for Harvey-haters: Harvey = ChatGPT, buyers regretting it, juniors are the only users (this is straight bull$%it btw), toxic culture. Here’s the reality: usage varies by firm, sure, and working at Harvey is no one’s model of work-life balance — but that’s true of every successful hyper-scaler. The real point is: the haters just heard what they wanted to hear. That’s why I was skeptical that this person actually worked at Harvey.

The lesson from Harvey is that to win in the age of AI, you need to develop a core insight about your market — what Peter Thiel calls the contrarian take — plus an iconic brand that lands with your customers. Harvey has that in spades, and not just because they have a great name or a pretty logo. Harvey understood that, at least at first, AmLaw 200 firms and their biggest clients were not going to want the standard consumer ChatGPT, they were going to want a special-made-for-lawyer model. That doesn’t necessarily make firms rational. As an example, I was advising firms at the time to just sign up for an enterprise plan with OpenAI. Today, everyone has realized was probably the right direction to go two years ago. But, at the time, they wanted something professionally customized and that’s become table stakes for most big firms. Harvey’s team understood how to message and design for that. And they’re reaping the rewards.

The power of harmonizing core insight, product design and brand.

Harvey hasn’t necessarily been winning deals on their tech. Harvey has been winning deals on their execution on brand and product design, which are really two sides of the same coin. To the r/legaltech shitposter’s point, how much difference is there really between Harvey and ChatGPT? But I think that misses the point. Drink Coca-Cola from an off label bottle, and tell me if it makes you feel the same.

By onboarding top firms, raising a war chest from the likes of Sequoia and Kleiner Perkins and making the decision makers at Harvey-adopting firms look like pioneering innovators, Harvey created a permission structure for sophisticated lawyers to use AI, and the Harvey team embedded that in every part of their brand.

Did they really need all that money just to build an application layer product? Probably not. But they’re selling more than their product. They are selling the idea that AI is fast moving, things are going to change and you’re going to need a partner to power you through that transformation. They are telling customers, we’re going to have to pivot, budget for compute and acquire other players along the way. But customers can rest assured because Harvey has the resources to do all of that and more, as do their backers who are the most trusted names in Silicon Valley. They are telling firms, ride with us.

Here’s another place where extra capital will come in handy: some firms are going to cut ties with Harvey. They’re going to look at their modest usage stats and decide to replace it with ChatGPT or they’re going to prioritize other products whose ROI shows up more clearly on a P&L. This will likely create a herd mentality where other firms cut bait with Harvey. This will happen to other products as well. Does that mean the company will go bust? No. I would still bet on them to be the clear leaders in Biglaw and Fortune 500 legal departments one year from now.

What can startups and incumbent firms learn from Harvey and “r/legaltech-gate?”

If your takeaway, then, is that Harvey is vaporware or Legal AI Theranos, you’re going to be disappointed. And you’re going to miss out on the more important takeaway that is deeply pressing to both incumbent law firms and startups.

So many of the companies we are working with right now, whether it is firms, service providers and tech companies, have been moved by the AI revolution to reevaluate their organizational structure, their services and, yes, their brand. There is a major shift taking place right now which is going to impact just about every professional services business. Disruption will create new opportunities for firms to capture business from their competitors as well as capitalize on new opportunities in an economy that is changing rapidly. That realization has them breaking and redesigning, in some cases from scratch. The challenge is that everyone has access to the same underlying models. So, therefore, the winners will be those who move first, develop key insights about their clients and execute on a brand and design that lands with their target users. Even if it means getting a healthy dose of hate along the way.

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How can you not be impressed by Harvey?

Even if you were a Harvey-skeptic or even an outright Harvey-hater, admit it: you didn’t think they’d get this far this quick. So, are we ready to crown them?

Hey there, I’m Zach Abramowitz and I’m Legally Disrupted. Today, I’m finally ready to drop the sequel to my widely read post “So Much Hate For Harvey, and I Can’t Help But Love It.” Want to know why? Because Harvey means a lot of eyeballs and I’m nothing if not click-hungry. My posts about Harvey got roughly 2.5x the traffic of my next highest read post.

But, before I give you the Harvey hot take you’ve been so desperately craving, first let me tell you about an opportunity for you and to meet in person. If you don’t care and just want to get to the Harvey stuff scroll past next the picture.

I’m going to be speaking in San Francisco this Thursday, June the 12th at Legal Innovators California, brought to you Artificial Lawyer founder Richard Tromans and Cosmonauts CEO Timo Karkashev, the hardest working man in #legaltech. I’m going to be on stage recording two live podcasts: one with Gravity Stack’s Bryon Bratcher and the other on investing in legaltech with Chris Fisher from Myriad Ventures and Jonathan Levy from Y Combinator. I will also be judging the startup competition at the end of the Day with Eli Amsellem from Ridge Ventures who knows more about the legal AI startup ecosystem than just about anyone I’ve met, VC or otherwise (podcast with him dropped today). If you’re in San Francisco and like to attend the conference, you can register using this link.

Making the Case for Harvey

Ladies and gentlemen of the Legally Disrupted Jury, the case for Harvey is pretty simple: a pair of elite founders with unique experience have executed at an unprecedented speed and scale. They show no signs of slowing down and their lead is insurmountable.

Some important background — and pay close attention, because I’ll be circling back to many of these details. Harvey, originally named Counsel AI was founded by first year O’Melveny attorney Winston Weinberg and Gabriel Pereya, an AI researcher who worked had worked at Google Brain and Deep Mind. Harvey launched publicly two and half years ago in the wake of ChatGPT’s arrival, complete with a seed investment from OpenAI. Shortly after, Harvey launched its partnership with Allen & Overy in February of 2023, and at the time I said publicly that this was a big deal. (Check the comments on my X post, you’ll see that not everyone agreed)

A mere two years later, Harvey is in advanced talks to raise capital at a $5 billion valuation according to a report from Reuters. The company’s annualized revenue run rate hit $75 million in April, up from $50M earlier this year (50% growth in a matter of months).

So, I’ll repeat what I wrote two years ago when I analyzed the A&O announcement: this ain’t your grandpappy’s #legaltech. Here are just two examples:

• It took eDiscovery leader Relativity a decade plus to reach a billion dollar valuation, it took NetDocuments over twenty years. Law firms are supposed to be hard to sell to, and legal departments don’t have big tech budgets. Harvey is closing deals with both.

• VCs have mostly been burned by startups selling to legal, but that hasn’t prevented Harvey from raising capital from from Google Ventures, Kleiner Perkins, Sequoia, Sarah Guo and Elad Gil — not to mention OpenAI. Harvey is having an impact outside its own cap table by creating serious FOMO around Silicon Valley. That FOMO is fueling VC interest in other legal AI startups.

Harvey just does everything so gosh darn well.

Take their brand for example. Legora, one of Harvey’s very worthy competitors has a great product as well, but they don’t come close on brand awareness. Harvey’s not just one of the hottest companies in legal, it’s one of the hottest AI companies period. I listen to a lot of podcasts outside of legaltech and it’s crazy how many of them will mention Harvey. I’ve talked with managing partners at international firms who insisted on Harvey licenses for the firm’s attorneys. “He was very clear,” one partner at the firm told me, “we had to have Harvey.” Other firms that are ripping and replacing their custom built internal AI chatbots (shocker, I know) have told me they’re not going to get burned by any of the smaller upstarts, so they’re only looking at Copilot and Harvey. Think about that. Since when does a two and a half year old startup have such meaningful market penetration that it gets grouped with Microsoft as one of the “safe choices?” I have spoken to companies about to pilot Harvey, and they are kid in a candy store giddy over the prospect. Let’s now list all of the other legaltech solutions that have generated that kind of excitement:

Annnnd we’re done.

It’s not just brand, it’s also their product. If you were hoping that Harvey was some kind of thinly wrapped vapor ware sold by Silicon Valley bros to unsuspecting law firms — Theranos for lawyers if you will — then I’ve got some news for you: many of the attorneys and legal staff who I’m speaking to, both senior and junior, say they really like Harvey. Not just like — “like, like.” I’ve seen lawyers using the product, it’s objectively slick1.

Part of the reason Harvey is gaining real traction is that, at the moment, it reinforces the leverage model. At an AmLaw 200 firm, the job of the partner is to bring in business and then push that work down to more junior attorneys. The problem is that junior attorneys are slow when you need them to be fast and incompetent when you need them to be trained seasoned professionals. Nothing used to annoy partners in my firm more than me asking them how to do work they had delegated. Years later, I get why. They’re busy either selling new business or noodling on some strategic question that, at least in their mind, requires intense periods of brooding. Harvey solves both those problems — here’s how:

1. When a partner needs a quick gut check answer, they can use Harvey rather than delegate to the junior lawyer.

2. When an associate needs to learn how to do something they’ve never done before, they can now ask Harvey. Partner can now brood uninterrupted — or better yet, use AI to help them brood better.

Back in my day, if a partner asked you to do something you had no idea how to do, you had to hope that Practical Law Company would have relevant content (this happened exactly never) or that you could easily find precedent documents in your DMS, both of which nearly caused me to break into tears at 3am in the morning, the night before a closing. If I could have just had Harvey on standby to hold my hand, it would have had saved me some serious anxiety. Isn’t that what people actually want from their tech?

Now, some people will tell you, “Harvey is just ChatGPT for lawyers.” Um, have ya used ChatGPT? It’s kind of awesome. Calling Harvey ChatGPT for lawyers — I would say high end lawyers — is not nearly the dunking-on they think it is. Spellbook, one of Harvey’s competitors, has generated huge growth off of basic social ads in which they brand themselves ChatGPT or Claude for Law. Harvey thinks and sounds more like a lawyer and also allows lawyers to perform a variety of tasks that ChatGPT or Claude do not do out of the box.

I’ve heard some people say, “Well, they’re only doing well because of their relationship with OpenAI.” Okay, but ask yourself this: plenty of other startups could have developed a unique partnership with OpenAI, but only Harvey did. That’s an example of great execution. In this case, they made the decision to approach not Sam Altman, but the GC of OpenAI who was more accessible and more capable of assessing whether or not LLMs were useful for lawyers.

A big part of why they’ve been able to attract best in class investors, partners and customers is that the founders appear to be exceptional — especially for first-timers. Pereya was at Google Brain and DeepMind in 2016–2017, right smack during the time when the University of Toronto and Google Brain were publishing the groundbreaking paper “Attention is All You Need.” So he had a front-row seat to the transformer revolution before we had even heard of a GPT.

They’ve also got the look. I’ve told this story before, a little over a year ago an investor-dealmaker quipped to me sarcastically, “Winston Weinberg is going around pretending to be Mark Zuckerberg.” But here’s the thing: Weinberg actually does look and sound like Zuck. My guess is someone told him to lean into it, but it seems to come to him quite naturally. Looks matter, especially to our lizard brains, which struggle to separate “this guy looks like Zuck” from “this guy is building the next Facebook.” I remember at my YC interview, a few guys walked out wearing toe shoes and sporting long dreads, and my CTO turned to me and said, “They’re going to get in — they look like hackers.” I’ll say it again: looks matter, and Harvey has the look.

But it goes beyond looks — and if it sounds like I’m crushing a bit on Winston Weinberg — I am. Weinberg has done three podcast appearances, all with his investors, and three things in particular stuck out to me:

1. They really understand the intersection of brand and product, are thoughtful about both and take full ownership of brand. I mentioned before that Harvey was originally named Counsel AI. Weinberg noticed that when they changed the name to Harvey, people prompted better. That might sound simple, but it reflects a deep thoughtfulness about product — and especially understanding that what makes LLMs special is thinking about it as your personal teammate. In my post last year, I talked about the Harvey Spector angle of the brand, but one of the other things they liked about the name Harvey is that it sounds like Harvard, which is still something lawyers care about. Again, that’s a very deep understanding of consumer psychology, especially for a couple of guys in their twenties who never worked on Madison Ave.

2. There is no work life balance at Harvey; they are obsessive work-a-holics. That might not resonate with you but trust me, whether you are an investor or a customer, it feels great when the team you’re betting on for the future is all-in. Listen to his three podcast interviews and try tell me that guy has taken a single day of vacation in three years. No way. He loves it too much.

3. Embedding with customers is easier said than done, but Harvey has done it. You’ll often hear Weinberg say that Harvey is partnering with legal to transform the profession. This language is carefully chosen to disarm lawyers who were concerned that they might be letting in a trojan horse and give them a sense of ownership and control in the transformation. Partnering with an industry in transformation also describes how closely Harvey’s team has worked with lawyers, especially those at A&O Shearman to really understand how they think/operate and what tools/data they use. This approach was pioneered by Palantir through its forward deployed engineer model, a title that has gained significant traction, especially in the age of AI. But, like reaching out cold to the GC of OpenAI, creating relationships in which employees feel comfortable to share how they work and allow you to observe, ask questions and build a product that automates what they do requires careful execution.

It hasn’t all been smooth sailing for Harvey. They spent too much time fine-tuning their model, they’ve had some senior level departures and their aggressively stealthy approach rubbed some people the wrong way. While they’ve managed to repair certain relationships, others I’ve spoken with want nothing do with them. But, like Weinberg himself says in the Grit podcast, having a long runway gives you cushion to fix mistakes. No one builds a Unicorn without making some mistakes along the way. The fact that Harvey has recovered so quickly is a testament to the founders, and part of the reason that they are adding even more top flight investors to their cap table.

Critics often argue that application-layer companies like Harvey don’t have a moat. But here’s the thing: every strong moat once looked like open ground, right up until it wasn’t. Today, Harvey’s moat includes, among other things, its brand, its blistering pace of innovation, its embedded network of law firms and legal departments, its growing list of strategic partnerships (including with iManage) and a nine-figure war chest that few can match. Sometimes you raise money because you have a moat, sometimes you raise money to create a moat. With this much capital and traction, Harvey is poised to outpace or acquire its would-be challengers.

With all that said, here’s why I’m not ready just yet to crown Harvey.

The Case Against Harvey

Harvey’s not the only fast growing Legal AI assistant for high end lawyers, and they’re not the only elite team in the game. They’ve outraised everyone, sure, but that may not matter as much. Harvey’s initial traction is impressive, but it may not last.

AI for legal is bigtime now, and having a rockstar team isn’t determinative, it’s table stakes. Max Junestrand from Legora, Scott Stevenson from Spellbook and Maged Helmy from NewCode are also exceptional young entrepreneurs — I’m talking real outlier talent — who are building powerful AI applications for lawyers. After spending time speaking at length with Max and Maged at this year’s legalweek, I was left feeling genuinely humbled.

Hebbia.ai’s founder George Sivulka dropped out of a PhD in computational neuroscience at Stanford to start Hebbia with the backing of Peter Thiel. Kevin Walker at Centari, Caleb Harris from &AI, Richard Robinson at Robin — I could go on. You can’t win in this market on dynamic team alone, but you better have one if you intend to compete.

The other companies in the space are also showing rapid growth, embedding with their users and building wow products. Legora, which just announced their own $80 million mega round recently may not have Harvey’s ARR numbers, brand awareness or dry powder, but they have their own impressive customer list and can absolutely catch up. Plus, they have the benefit of having seen what worked and didn’t work for Harvey. NewCode is an even more recent entrant, but I expect them to compete neck and neck against the others as well as carve out its own unique go-to-market. Also, while Harvey has been able to land early customers by making them look innovative through press releases, highly produced videos2 and case studies, the value of that marketing diminishes. Several firms I’ve spoken with specifically don’t want to do the thing that everyone is doing.

Speaking of go-to-market, I’m meeting with many of the earliest stage companies, and what I can tell you is that there a whole group of teams building wedge products that firms really need. A great example a company that’s chosen one thing to exceptionally well is Centari and their laser focus on building a best in class deal point engine. Others like Aracor.ai are hyperspecializing with specific customer segments like investment funds.

Harvey’s go to market on the other hand was to build a tool of general application for all law firm attorneys. Building such a tool can be very lucrative if you’re selling seat based licenses. At the same time, it requires you to keep the product simple enough that everyone at the firm uses it e.g. regulatory, tax, IP, transactions, disputes, can get from it what they need. An IP specific tool may perform better than Harvey does on IP workflows but, unless there is a decentralized purchasing process at the firm, Harvey’s going to be easier to procure. The bigger challenge for Harvey will be that not every firm is interested in a legal specific tool of general application. These firms instead prefer to use Microsoft Copilot, Google Gemini or build their own bespoke solutions on top of the foundation models. With the growth of vibe coding, building and maintaining your own solution has become easier than ever and will only continue to get easier over time.

Beyond the legal specific competitors, Harvey is not immune to being steamrolled by OpenAI. According to a recent survey by Law360, the tool lawyers use most for legal work is ChatGPT, and it’s not particularly close. I’m hearing from more and more attorneys that OpenAI’s Deep Research is the single best research product on the market, and it’s what most attorneys use (even when it’s not a firm approved tool). I’ve thought this for a while, but I’m hearing it more and more from people who are practicing. You might have seen a flurry of recent news stories with top firms submitting briefs filled with hallucinations. The reason I believe you’re seeing those stories is because more attorneys than ever are using Deep Research, and it usually works so well that people have unfortunately let their guard down and missed a fake case.

So could Harvey and the other legal AI assistants ultimately be defeated by OpenAI itself? A rising star litigation partner who prefers using one of the foundation models told me that Harvey offers them zero value above replacement. That’s not true for everyone I’ve spoken with, but if you asked most litigators to choose between Harvey and ChatGPT right now, my guess is they’d pick ChatGPT.

Harvey’s war chest and its unicorn valuation may also not be the flexy that they would have been five years ago. There’s an emerging group of companies that are specifically trying to scale with lean teams and raise as little money as possible, the so called single employee unicorn. The idea is that AI is increasing productivity so significantly that the traditional rules of scaling can be thrown out. Bigger isn’t necessarily better. An entrepreneur can make more money if they raise as little as possible and hire as a complete last resort. A great example of this is Base44’s CEO Maor Shlomo, who raised hundreds of millions for his last startup Explorium.ai. But Base44, a vibe coding product, is already generating $189K a month in *profit.* Shlomo is the only employee and the startup is bootstrapped.

Windsurf CEO Varun Mohan describes how he runs his company to the point of “dehydration,” intentionally avoiding traditional hiring practices that try to anticipate needs six months in advance. The best teams could ultimately see the greatest marketing opportunity in recreating Harvey-style products at a lower cost point without the baggage of a cap table?

And then, finally, there are real questions about the stickiness of Harvey’s revenue. This point was articulated recently by Paid.ai founder Manny Medina in an interview on the Training Data podcast.

I think the highest paid people will buy AI as a side thing and ditch it with the same regularity that they ditch other things in their lives. I think AI is going to stick the landing where it actually takes over our role fully that nobody else wants to do. So for instance, nobody wakes up and wants to be an insurance actuary or an insurance adjuster. So the turnover on these jobs are really high…So what I’m observing from my end is that the companies that are doing really well are addressing pools of labor that are either disappearing because of retirement or they want to do something else.

According to Menlo Ventures “2024: The State of Generative AI in the Enterprise,” 60% of all AI spend right now is coming out of innovation budgets. I would argue that general applications have the greatest risk of being cut, especially if innovation budgets tighten. This is where companies like Robin (AI legal document review) or LegalMation (high volume disputes) may not have the growth or headlines that Harvey generates, but the revenue would survive an AI innovation winter.

So Harvey, Yay or Nay?

I genuinely don’t know. On the one hand, I wish I owned Harvey stock, but at an earlier round. Would I buy the stock in their current round if I could? I don’t know. The FOMO would probably get the best of me and I’d talk myself into it. After all, I would tell myself, what do I know that Sequoia or OpenAI doesn’t? That doesn’t mean it would be the right decision. I’ll settle at this: I’m pretty sure Harvey isn’t going to be a bust, but am I ready to crown them and tell other entrepreneurs to choose something else to work on? Nope, not yet. This competition is just getting started.

A year ago at the CLOC Global Institute in Vegas, Robin.ai was the talk of the conference — the "CLOC on the walk," if you will.

This year? They didn’t show up.

And that’s not because they’re doing poorly. Quite the opposite — Robin is crushing it, working with some of the biggest and most sophisticated companies in the world.

But, as I will explain, this is really a sign of the times: AI doesn’t just have legal’s attention. It has the lawyers’ attention.

Hey there, I’m Zach Abramowitz and I’m Legally Disrupted — welcome to the missile-hit-my-airport so I couldn’t make it to Vegas edition. In today’s installment we examine AI’s disruption of CLM and legal operations through the lens of one of the fastest growing legal AI companies: Robin.ai, which has built one of the most robust AI solutions for contracts.

2024: CLM? OK Boomer

At last year’s CGI, Robin.ai made waves by outright dismissing CLM as an outdated concept. The below is a slide I put up at last week’s ILTA EVOLVE in Myrtle Beach.

Their messaging positioned traditional contract lifecycle management platforms as bloated, ineffective and in need of retirement. This isn’t limited to legal, of course. AI natives have been throwing shade at legacy providers like Salesforce and saying that the entire CRM vertical is a walking zombie. But Robin was the first to say it in legal — and they did it from the center of the exhibit floor at CLOC, the actual sacred shrine of CLM.

2025: Is Legal Ops Being Replaced By AI?

This year, I was particularly interested to see what marketing language Robin was going to drop on CLOC, but then I noticed that their name was conspicuously missing from the website. Rather than follow up that very loud statement with another splashy booth or panel, they did something arguably louder: they skipped the show entirely.

But to quote Indigo1 Montoya, skipping CLOC may not mean what you think it means.

I reached out out to Robin’s Lauren Watson (total rising star btw), who told me that the company is doubling down on a different strategy. They’re hosting smaller, owned events — 20 GCs in a room, bootcamp-style — where in-house teams actively test Robin’s AI in live scenarios. These sessions, Watson says, are producing stronger ROI than big tent events.

Now, let me explain why this is a big deal, not just because of Robin, but what I believe it signals about the profession at large: AI has earned the attention of lawyers. According to a recent survey from Law360 AI adoption jumped from 35% to 55% in just one year. The very fact that Robin can create owned events is because there are lawyers who are really focused right now on figuring out how AI can improve their department. Attention may be all you need, AI has made lawyers fall in love. Among frequent users, 94% say AI has made their work better — indicating more than just mere curiosity.

Lawyers haven’t always loved their tech. Over the last ten years, a good amount of the tech that has been foisted upon in house lawyers (especially at bigger companies) came from purchases made by the head of legal operations.

It was hard to get lawyers to care enough about the tech to do the vendor evaluation (so they hired legal ops people to own that), but that didn’t stop the lawyers from complaining or end-arounding the system.

That’s not the case with AI. And why should it be? AI is amazing? I mean, seriously have you used AI? It’s life changing. And I think a lot of lawyers — including GCs and CLOs — are thinking to themselves that all that operational efficiency and process improvement was great but, umm, have you seen AI??? Where will a GC get more value right now? Hiring a legal ops position or getting everyone in the department access to an AI assistant. AI isn’t like legacy software that was essentially built for the company and, in order for it to work, employees had to use it. AI is built for the employees who WANT to use it, but it makes them so productive that it helps the company.

Maybe I’m making too much of this, but it was interesting to note that in 2024, 40% of Chief Legal Officers identified operational efficiency as their top strategic priority, while only 6% considered technology implementation a major concern. By 2025, operational efficiency remained the leading priority, but now only for 35% of CLOs, but interest in technology implementation more than doubled, rising to 14% and becoming the second-highest priority overall.

Is it just me or is technology cutting into legal operations mindshare?

I think it is. Apparently, so does the team at Robin.ai. And you my friends have now been disrupted — legally disrupted.

Hey there, I’m Zach Abramowitz, and I’m Legally Disrupted.

You might have thought today’s post would be about my takeaways from the Legalweek conference in NYC or the much awaited sequel to my post about Harvey. It is neither, although you’re right — both the posts are in process, so stay on the lookout and subscribe if you haven’t already. But, today’s newsletter is about creating a roadmap for how to adapt personally and professionally in a world that is quickly becoming more AI native. TLDR: become a better human.

I’m in Chicago today at Evolutions, a conference put on by Podcast Movement. I’m here to promote the launch of Targeted, a brand new story-style podcast I recorded earlier this year and which is produced by Next Chapter Podcasts. It’s not about lawyers (although we interviewed a few) it’s not about AI (although AI comes up) and, at first glance, it might not be clear how this podcast fits into our other work at Killer Whale Strategies.

I’ll get into the topic of Targeted in a future installment but, today, I want to explain how this fits in with a Killer Whale strategy and why I believe that constantly going just outside of your comfort zone is going to become the new normal, especially in light of the meteoric rise of AI.

I discussed this recently in a LinkedIn post, but every year, I try to take on one project that forces me out of my comfort zone. I try to choose a project that will also improve the services we offer our clients. So how does a highly produced podcast help our clients?

KWS helps companies of all different shapes and sizes capitalize on disruptive trends impacting the legal industry. Our work sits at the intersection of intel, strategy and storytelling. We help clients make sense of emerging trends — like AI — and translate those learnings into strategy, which almost always requires some degree of change. But change doesn’t stick unless you can explain it easily and that’s where storytelling comes in. And I believe this is what truly sets us apart when it comes to advising firms and top executives on AI: informed, strategic storytelling.

Informed, strategic storytelling has been a huge part of our business. Over the past few years, we have produced 75+ webinars, nearly 50 podcast episodes, highly produced video case studies, short documentaries and one super cringey music video (not to mention speaking gigs and newsletters). This latest project — a beautifully produced, narrative-driven — pushed me in new directions, and I loved it. The truth is I always enjoy acquiring new experience, especially when it’s uncomfortable initially. I think most humans do.

We’ve gotten so used to the “stay in your lane” ethos, but perhaps we are entering — or reentering — a new phase. There was a time when humans aspired to be multifaceted and dynamic. Leonardo da Vinci famously wrote a letter to the Duke of Milan seeking patronage and employment. In his letter, he had led with military engineering, siegecraft, bridge design. Painting was almost an afterthought. Today, that kind of range feels almost alien. We live in an age that rewards specialization — or at least the appearance of it. You're a litigator. You're a corporate associate. You're an AI startup founder. You're a marketing expert.

But maybe we’re swinging back. Maybe AI is pushing us toward a new kind of Renaissance thinking. Not just mastering a narrow task, but navigating between fields, combining disciplines, pulling insights from everywhere. And maybe humans, with the help of AI can now more easily teach themselves new stuff. One of my favorite use cases I like to share is how I used ChatGPT and my phone camera to fix a boiler in an Airbnb in London.

Because in this new environment, the real advantage won’t come from staying in your lane. It’ll come from adaptability — the willingness to take risks, explore new territory, and rethink your methods entirely.

That’s part of the reason why I named our company Killer Whale Strategies. The spirit animal of the lawyer is clearly the shark, but the lawyers of the future will use killer whale strategies. Killer Whales don’t just repeat what works — they actively experiment. They are constantly iterating. Killer Whales have been seen beaching themselves to snatch seals off the sand, then wriggling back into the water. It’s dangerous. It’s uncomfortable. But it works. And once one whale figures it out, the rest of the pod learns too. Sharks hope things stay the same, Killer Whales evolve.

To be clear, the new thing you learn doesn’t need to be AI. But AI can uniquely help you lean new things. Doing both will make you a better human. And whatever you do, make sure to stay disrupted — LEGALLY DISRUPTED.

Could “AI For Lawyers” Catch on Faster with In-House Attorneys? Katya Fisher, CEO and Founder of Aracor

Happy New Year! I’m Zach Abramowitz and I’m Legally Disrupted. I’m also way behind on everything, hence the newsletter version of radio silence. There’s so much we’ve got to get to:

1. TermScout sold Screens.ai to Agiloft. Lots to talk about here, including the fact that this was the first of my startup investments to have an exit (Congrats Otto, Evan and the whole team!). Although, as I’ll explain in an upcoming installment, the term exit doesn’t entirely capture the richness, complexity and nuances of this deal.

2. I’m currently writing the sequel to my much ballyhooed post about Harvey.ai , and meanwhile reports are surfacing that Harvey is raising so many monies at so many multiples. AI is clearly moving faster than my newsletter — yikes.

3. I still haven’t gone over what I got right and wrong in my 2024 predictions. This has been a tradition of mine going back a few years now. And I’ve got quite a bit to flex on.

I haven’t forgotten about any of the above, but due to unforeseen circumstances (the good kind), our team had to work straight through the holidays and we are still behind on just about everything, so commentary on all of this is forthcoming, but sadly delayed.

What I did get a chance to do over the holidays (because I was in the office anyway) was record a couple of podcasts, including this one which I’m releasing today with Katya Fisher, CEO of Aracor.ai, a AI powered solution designed specifically for investment firms: family offices, PE, VC, real estate funds etc. I’m going to have plenty to say about this startup, but I’m going to tease the podcast by telling you the following: Katya is built different and she thinks different. It’s partly because of her upbringing, unconventional career path, and superpower level curiosity coupled with the fact that she seems to be missing anything resembling a fear-gene. We get into all of that in this podcast. Here’s a little teaser:

Listen to the full podcast on Apple Podcasts and here on Spotify.

More disruptive content will follow, but in the meantime enjoy this convo with Katya, binge on old episodes and, as always, stay disrupted — Legally Disrupted.