In this 42nd episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the mid-year recap, selecting the proper AI tool, merger mania, and creating a competitive advantage in legal.
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Episode Transcript
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(00:00):
Welcome to charting change in legal. I am R.I.
(00:06):
Kaplan and analyst who covers the legal industry and as always I am privileged to be joined by my colleague.
Caroline Hill, hi everyone. I am the editor-in-chief of Legal Artie and so I'd be great to be here chatting with you.
R has been a little while now.
I love these conversations. I will maybe set the tone for this call by saying the world seems to be moving much more rapidly.
(00:32):
I mentioned to somebody recently. I said with all of the different changes that are taking place in legal specifically,
it feels something like sand falling through your fingers where you're trying to capture every nuance, trying to follow every development and trend.
It's just a single person, a single team isn't really capable of doing that. You just have to capture what you can and keep moving forward because we are seem to be in a very rapidly shifting environment at the moment.
(01:03):
So true, so true, because as you know I cover the news and I'm supposed to cover all the big news, but there's so much big news.
So in the case of do you just do less but go deeper or do you take this full gambit and then just you're at risk of just producing press releases, which is the thing that myself and other, you know, like the Bob Ambroughies etc.
(01:26):
We talk about a lot, which is how do you do justice to this time?
But the time does seem to be moving really quickly. I cannot believe Ringer Lines.
Yeah, no, the idea that we are at the midpoint of this year is not surprising, but still gives you pause and I will, I guess you'd have to say that legal is experiencing a vibrant moment, you know, yet another vibrant moment where there just seems to be lots of opportunity and trends that are solidifying.
(02:02):
So exciting time to be here exciting, yeah, exciting and interesting for law firm management, you know, like as to so many so many sort of opportunities for them to make big changes, but yes, it's still a challenge for them as well, right?
With so much coming down the track and all the lawyers clamoring for the latest release is not just a challenge for us, right? It's just a challenge for everybody involved in the legal sector, but also so important about you saying about opportunities, you know, sometimes I think I focus too much on the challenges, but huge opportunities for the people that are doing great stuff.
(02:41):
Well, also as you know, people are obviously enthusiastically gathering now lots of conversations, lots of interaction. I was lucky to see you recently in London and I went to relativity fest and then I hosted my own breakfast at link later and then I went to Lexpo and then hosted a breakfast at how top and the one trend that I keep finding is that
(03:10):
as opposed to going to an event to learn everyone is now sort of the speaker right everybody has something to share there's a communal interaction communal like intellectual sharing that's happening so that all of these events whether they're large conferences or small breakfasts or dinners or whatever.
(03:34):
Every each person is there to contribute and to learn as opposed to just absorb knowledge everybody has some experience that's worthy of a peer learning and I love the egalitarian nature of what's happening right now.
It's so funny that accords exactly with my experiences of hosting webinars or planning some stuff around Ilter in person events and I started to call it group therapy sessions because it's just it's it's everybody does have stuff to share but I feel like you know it comes from a place of us all needing to talk to one another you know it's that it is that sort of group support and how are you doing things and and am I on the right page and.
(04:19):
And sharing yeah I think there's a need to share right now and I did joke I had a sort of we normally get quite a lot of people in our webinar hosted one the other day that was quite a niche area and so no less people and I was right everybody is just our little group therapy session everybody ship in.
And it feels like there's a need to do that.
(04:40):
People also want to experiment they want to share ideas they want to share best practices and test it out in a safe environments like we're living all living in a sandbox at the moment just trying something seeing if it works let me try this different tactic or process I tried this I entered this in whatever system and it's not just AI right I mean there's a renaissance in a lot of things happening practice management document automation lots of different things.
(05:09):
And that it's it's almost as if this one massive trend is elevating the entire industry to be more thoughtful about how they work and how they acknowledge the work of others yeah and that's funny actually so perhaps.
Well in terms of I know it's not all about AI but in terms of the AI stuff I've written about recently there people are becoming more forensics so there's been a big steep learning curve but in terms of how they're interacting within the firm and their selection process etc but they really learn now what works and so I was at legal tech talk very recently which was great we can perhaps come back to that as a conference.
(05:58):
But I did an interview with Joe Cohen who's head of innovation at Charles Russell speech and he was sharing about they have just selected Harvey literally I just wrote about it at the beginning of the month and so beginning of July and they did this huge selection process like I think you know there's been a long period of engaging lawyers you know I think it's interesting because I've written about legal tech now for 10 years and and at the beginning it felt like it was a to an IT.
(06:27):
And lawyers weren't really involved you know like that all rarely anyway but now because obviously the change in the type of technology and how it's been used and it's been used is a very much a lawyer's decision so so they were talking about the Harvey process they went through this extremely in depth multi prong selection process where they tested all kinds of different different systems different software obviously comparable and it was interesting that he said they are.
(06:56):
He said they only went with big fenders because they got a little bit burned by they initially chose spring book AI which got bought by clearly and then obviously had to change so so anyway so they but they what was interesting was the depth of the process and the fact that they had all these they had.
(07:17):
So about nine different questions across nine different areas that they were testing and so that was interesting in itself they got lots of lawyers involved who were quite willing you know they were like they're sort of their.
High uses of spring book AI and they came out Harvey is interesting as well from a Harvey perspective because Harvey came out on top of every single category by a significant margin so that's obviously who they went with but it but it's interesting hearing those conversations.
(07:46):
You know in terms of people are this is what people do right they they've been clever at their jobs for years but it was just interesting as to how.
You feel the learning curve right that we're becoming sort of a quite different taking quite a different approach now and before they.
Start talking about tools now they're talking about tactics and processes and use cases which is also a shift I remember being at legal week and meeting with some partners at a law firm and they.
(08:21):
Ask me if I could just tell them what tool to buy and I thought.
What I couldn't even understand why they had immediately you understand why they asked that question but I couldn't understand even why they thought that was the logical question because they didn't say for what you know they just said can you just give us the tool or a list of things that we should just buy and implement and I thought oh my gosh that's not you are not approaching it the right way and we all laughed and then I realize now that more and more organizations are.
(08:57):
Are hearing that and recognizing that it's much more about you mentioned this forensic look it's much more about really opening the hood and trying to figure out how how are we working rather than how does this work then we can kind of figure out what is effective and in fact in a lot of these conversations people may not even mention the names of tools they may just mention we tried this and we learned that this group does it this way and this group is interested in.
(09:26):
This group is interested in this and that we have certain users here and that is really something that is particularly effective which is why I think at any event you go to again small large international local people want to hear specifics and they're not really.
That focus necessarily on the big flashy thing right which is why you're seeing you know time capture and time entry and things that are so standard and legal getting lots of attention because even though they're not super flashy as much as you know something else might be they're really valuable obviously and you know if you can transform something like that it can change everything in an organization.
(10:14):
It's so fascinating so I spoke with Ryan the founder of it used to be time by ping and it's obviously they are focused entirely on time capture and they're doing some super cool stuff and actually that's a fascinating area because people haven't really ever understood time you know they're now as we're moving towards they're really seriously looking towards like flat fees or moving away from the bill of the hour or they can see it on their horizon for a big chunk of work.
(10:43):
They're having to actually really understand the way that they they're way that they bill and also there's a huge amount of un-villable amount of work that you can't charge for and they're really starting to dive into what that looks like and analyze business development and there's so much more analysis behind the scenes in terms of how do we actually work and we need to understand that in order to you know move to a position where we understand our value.
(11:11):
So I'm Ryan's really super interesting on that you know and they've obviously just they've just raised a hundred million dollars which is so really happy for him and it was really nice to see and I saw him at the tech talk as well.
I'll just say that he and you know he's a dynamic entrepreneur who's been committed to this since the early days I met him when he was part of the Lexus nexus legal tech accelerator many years ago just incredible and well deserved success.
(11:38):
I have to say that I love seeing the folks who have been committed to innovation and change and upskilling and improving the profession for so long really being recognized I mean they've been recognized but you know obviously the acquisition of V Lex by Clio is is an incredible milestone in our space but I have to say that I've read the
several posts including by Kevin O'Keefe the founder of Lex blog among other organizations and he wrote something that I think is quite interesting and I think it's interesting and I think it's interesting to see how he did it.
(11:59):
I'm not sure if I'm going to write but that I really resonated with with me which is those leaders particularly Jack Ed and Phil are are really in my you know my experience is so I'm really happy with the
very interesting thing is that I was including by Kevin O'Keefe the founder of Lex blog among other organizations and he wrote something I am going to write but that I really resonated with with me which is those leaders particularly Jack Ed and Phil are are really in my you know my experience just extraordinary individuals like human beings and the fact that they've combined is very meaningful and I just I had a personal connection to that transaction.
(12:37):
When I saw it I wasn't I wasn't home at the time I was away and I saw it and I thought I just I love this these people are just fantastic human beings they've certainly been supportive of me throughout my career and it sounded like you know they have done the same for Kevin and for I'm sure many many others it wasn't as much of the business transaction that resonated there just like you know your admiration for Ryan who's been you know doing this for many many years it's just it's interesting to see the personality.
(13:06):
I just see the personalities behind these developments and just to appreciate their commitment to this change which isn't easy.
No I mean yeah that's extraordinary I'll come back to Jack one second but I have to say I kept teasing teasing Ryan about where's the Lamborghini because obviously he's like shout out.
(13:27):
I've heard from a bunch of friends that you know that it's actually different than it becomes much more accountability right the numbers the numbers really matter they they create a level of accountability that forces.
You know just like a heightened business acumen and focus so I think it's not.
(13:48):
There's no number yeah the the raise isn't the isn't the moment I think you'll have to ask Ed and Phil where the Lamborghini is but I don't think that's their style.
I'm gonna be asking Jack.
Yeah yeah so Jack's a great I mean he's a great leader he's extraordinary you know I'm no doubt talked about him before because it's quite unusual for a CEO founder CEO to get to that stage right that because when you and Jack's obviously raised a lot of money.
(14:17):
And I mean that the acquisition for a billion dollars of Vlex is just extraordinary the money that's starting to flow is just extraordinary when you think about that number right.
And I think he's got the March show obviously what people are trying to do so Vlex is everybody knows combines AI LLM's with data so legal database which is which is currently where the value is in terms of you know really being up to
(14:45):
to apply the LLM to that to that legal database and and Vlex obviously been doing great job is it I mean it's interesting is quite a different.
It's quite different business for clear they're now in the business and practice of law so that's quite interesting that they're combining the two be interesting to see how they do it because it's a very sort of separate area but.
(15:06):
So just kind of curious is to how that will work and know that we'll have lots more conversations in the coming weeks about that I love them as a company and I'm sure they'll make it work fabulously as you say there will brilliant people you know and that is the best start and both teams have a good track record of incorporating the tools that would make them better so.
(15:28):
From if we're going to look at past precedent I think it's a good indicator of what this might look like but regardless of the transaction I think that it's important to acknowledge all the wonderful human beings behind us who have been really committed to the space and.
But it's still the research space just as a side somebody was saying to me they think that I mean in America you've got pace and you've got all kinds of you've actually had much more sort of legal case law such a legislation available or be it for a fee but someone saying to me that they think that going forward in the not too distant future that legal databases such as Vlex such as Lexus will be will be table stakes that actually that it will be available to AI and.
(16:12):
And so it's an interesting it's an interesting acquisition I think it's not going to be the the only one I think I I forecast other requisitions.
I'm going to be say of this because you're so excellent.
But so there'll be I think there'll be others but it's interesting in terms of timing is to how long it will be before actually you know we don't.
(16:33):
But I think this is a timing plane that they're going to have the March right there quick off the off the bat and I'd be interested to see what they do with it but but it's just kind of fascinating time in terms of how what what what is valuable now and what's going to be continue to be valuable going forward I think it's kind of fast.
I think things are going to change quite quickly.
The sand going through the fingers is even moving more quickly because there's more sand than it just pile on it will be interesting to see it's fascinating to me that we are now halfway through the year and wonder what will come you know you mentioned this idea of of the database being all powerful like the center of a lot of this being table stakes I remember being at
(17:17):
the last year and they had a discussion by lawyers and the legal team the innovation team at the European Union who had developed because of the complexity of their and anybody who's ever read the data directive or anything else that's been published.
It's complicated and so they had developed using their repository of complex documents a system a large language model that they were offering to the public because they used public money for it to develop it and it was really really interesting this is tool that you can build on and fascinating to see so I I encourage people to look broadly beyond just the handful of private companies that you see developing this.
(18:06):
Because there's incredible development happening in a lot of different directions and in areas where you might be able to access some of this information in in different ways and you know maybe more broadly.
Yeah, I do hope it's interesting because the spring book example I think it's interesting you know you would hope that law firms continue to work with companies and encourage innovation encourage.
(18:35):
Encourage new companies to come in you don't want to have just a collection of of large of large sort of dominant startups I think that the I think there's two two I've two thoughts one if you look at legal tech hubs map of of companies it's probably unsustainable is the reality so they were this really challenging period for firms where you know you've got so many different companies you feel like that's not sustainable in terms of the size of the market.
(19:03):
Interestingly with private equity so people have different views on private equity I was speaking to someone who said that they would view private equity investment of a company as being a positive thing because you know it doesn't it's not a guarantee but actually private equity is pretty smart where they put their money they they have a model where obviously they expect some to fail but but still nonetheless they said actually that would be a benchmark of we we hope that this will will be a success but it but you know it's it's a real challenge for firms at the moment in terms of who.
(19:32):
They work with right I think that that you know I don't really know what the solution is to that because obviously there been now examples of law firms buying companies which that means if private equity invest that's something different right they can carry on working with them but if law firms start buying them I think that's a sort of slightly more worrying thing so just be interested to see whether that detours law firms from working with smaller companies or or how that pans out when I host my
(20:01):
legal tech mafia breakfast usually in New York I mean I've recently done one in Amsterdam one in London I did one in south Florida but I typically host them in New York City and it's amazing to me the array of companies the sizes the development stage of individuals you know we'll typically have
(20:22):
40 50 people now come to the breakfast and you'll have companies you recognize and companies you have not yet heard of and I find that most of them are on a pretty good growth trajectory obviously the smaller ones I think that that's a
(20:43):
little bit something to watch it seems like there's a lot of opportunity you know the total addressable market in a legal has grown so significantly that that's in many ways one of the things I mean that's one of the things that's attracting and leading to this development obviously I think the barrier to entry is low and the ability to develop some of these tools requires a lower level of capital at this point but there's there's a lot of factors to play but I get this
(21:12):
sense that a lot of the companies that you start to hear about are really thriving and it would be interesting to see on that list because I know that list is is long to see how many of them are sort of completely unrecognizable because I think many of the companies on that list we would we would recognize so it's
the other thing is just to say that I was telling to another founder at legal take talk and they were saying that actually law firms can really help I know this is much easier said than done but he was saying that the sales cycle for small companies is so long and actually the law firms going to get where they're going to get anyway in many cases and actually they
(21:59):
said they really don't have to invest that much you know into in terms of sort of starting to do proof proof of concept and he's saying that they have a big perhaps response to
literally he's not the right word but they can they can make such a huge difference that they don't understand that these super lengthy sales cycles can be actually really damaging for small companies so it's a
(22:25):
little bit chicken and egg but and obviously law firms aren't just going to bundling and you know they've got a lot of decisions to make but it's just something for them to bear in mind I think I don't know if that is really something that a law firm is
responsible for changing I mean you know obviously the law firm has to protect its data its clients it has ethical obligations there's just a
(22:48):
ray of reasons why some of these things take time there are a lot of stakeholders it's an overhead expense I just think that it's an interesting discussion because this has come up the
sales cycle is long it's very hard to break through the noise that you see posts like this I've had conversations with folks like this it's come up in various ways at events that I've
(23:10):
been at and yet I don't know that that's the the challenge that you can work around it's often great product persuasive pitch you know there are different factors but the idea of a law firm reducing
it's cautionary protocols I think is a is probably an area that is less likely to change than than some of these others it's so problematic though you know and it sounds like it's
(23:41):
if you were selling to a bank or to an insurance company you'd be facing lots of the same issues I think yeah that mean but then so I mean I agree they're probably not going to change but but you know it's
chatting to the fact I found out the super successful company that's doing really well you know they're not struggling and we were talking about the private equity thing and I was saying you know about I was sharing the same observation that I just shared with you about you know this this guy who's saying you know
(24:10):
I suppose senior person at law firm the private equity is a good sort of benchmark and you know everyone's private is it's very polarizing right and the founder was who hasn't taken any investment was just so hard of
I do say my goodness you know law firms just need to move faster you know they need to find a way to innovate quicker whether it be small proofs of concept he said they don't
(24:35):
need to spend nearly as much as they think you know just to start testing in a you know like you mentioned the sandbox testing in a sandbox movie there are ways of speeding this stuff up right like actually if you want to be an agile organization then it shouldn't really take I get what you're saying right that
in order to roll out something on an enterprise basis of course you know there are lots of different hoops etcetera but actually just to do sort of small sandbox you know and and
(25:03):
and tests and behaving as an agile organization, which is law firms really need to move towards,
right? And also we move past the idea of IT just being an enterprise saying, right?
It might be that corporate need this and litigation need this and we're going to have lots of
different, and that presents a different conversation and a challenge in itself. But that's not
(25:24):
what we're talking about, it's more like the speed. I think I do feel like they need to find a
way to move faster, not just, I agree, it shouldn't be, the well-being of the startup isn't
their responsibility, but just for their own well-being and ability to act fast for their own
interests, I think, probably needs to do, they need to do better personally.
This has become a passionate topic.
(25:47):
Right, no, it's a really interesting topic. It's come up many, many times and there's a sort of
frustration. I assure you, and I know that you're as deeply connected to this particular community
as anyone, but the people who are responsible for making these decisions or participating in
these decisions would love to make them faster. I deeply believe that. I think that if they had
(26:09):
a bigger team, people who are directly responsible for one thing, driving innovation, even the firms that
have an incredible innovation team are still insufficiently staffed to manage every single possible
idea that could come across. It's on the founders and on those teams to be smarter about how they're
(26:36):
reaching out and to really recognize what value the people that they're trying to reach are most
interested in. You and I both do this. We both try to provide a forum in a lot of different ways to
give a voice to a lot of these organizations. I have a podcast and I have my virtual lunch and
(26:57):
I host a breakfast and I really want those companies to be heard and to tell their story.
I love to hear their story. I learned something every single time I've done, I don't know,
something like a thousand podcast episodes. Every single time I hear a story from a founder
I love to repeat a few years later to see if that founder brought her vision to fruition. I'm always
(27:21):
trying to figure that one out. I host a CEO round table, which I just hosted and I will say that
one of the benefits of convening these conversations is also to connect leaders, but to
have them again, coming full circle to the initial thing that we talked about, which is probably
a good closing point is that people who are doing the same kinds of work and who are challenged
(27:48):
with some of these issues that we're talking about need to connect with each other in a way that
allows them to be candid and to be vulnerable in some respects, which is a word that isn't commonly
associated with the legal profession, but a vulnerability that allows them to maybe see their
(28:11):
blind spots, help someone help them see the blind spot of this is an issue, not of our product
and not of our service and not of our approach. It's because law firms take too long to buy stuff.
It's like wait a second, let's have a conversation about this. How have you penetrated that?
What have you done? Oh, we have this incredible product. Everybody wants it. We're bringing it down
(28:32):
our door. Oh, maybe, you know, so I just think that there's an interesting solution here and that
solution in many ways comes from candid conversation that's honest and sincere.
Well, I always appreciate our candidates and to conversation. It's always a pleasure.
It's my pleasure to privilege, Caroline.
(28:54):
Niche, and we come as much. I know who even knows. We bounce it around. It's going to be hard to
listen to this, but I'm confident that Tom will make it and do his best. Anyway, well,
Caroline Hill, it has really been my honor. I've always enjoyed these conversations and excited
(29:14):
to continue on our schedule here and to just see what the next half of 2025 holds.
And Ari, I look forward to catching up next time when we'll be close to Ilta.
And so we can start to think about what's going to happen there and also we'll be able to get together.
Maybe without microphone. We'll have to bring our flashy microphones.
Caroline, thank you so much. Thank you. Bye.
(29:41):
[ Silence ]
Welcome to charting change in legal. I am R.I.
(00:06):
Kaplan and analyst who covers the legal industry and as always I am privileged to be joined by my colleague.
Caroline Hill, hi everyone. I am the editor-in-chief of Legal Artie and so I'd be great to be here chatting with you.
R has been a little while now.
I love these conversations. I will maybe set the tone for this call by saying the world seems to be moving much more rapidly.
(00:32):
I mentioned to somebody recently. I said with all of the different changes that are taking place in legal specifically,
it feels something like sand falling through your fingers where you're trying to capture every nuance, trying to follow every development and trend.
It's just a single person, a single team isn't really capable of doing that. You just have to capture what you can and keep moving forward because we are seem to be in a very rapidly shifting environment at the moment.
(01:03):
So true, so true, because as you know I cover the news and I'm supposed to cover all the big news, but there's so much big news.
So in the case of do you just do less but go deeper or do you take this full gambit and then just you're at risk of just producing press releases, which is the thing that myself and other, you know, like the Bob Ambroughies etc.
(01:26):
We talk about a lot, which is how do you do justice to this time?
But the time does seem to be moving really quickly. I cannot believe Ringer Lines.
Yeah, no, the idea that we are at the midpoint of this year is not surprising, but still gives you pause and I will, I guess you'd have to say that legal is experiencing a vibrant moment, you know, yet another vibrant moment where there just seems to be lots of opportunity and trends that are solidifying.
(02:02):
So exciting time to be here exciting, yeah, exciting and interesting for law firm management, you know, like as to so many so many sort of opportunities for them to make big changes, but yes, it's still a challenge for them as well, right?
With so much coming down the track and all the lawyers clamoring for the latest release is not just a challenge for us, right? It's just a challenge for everybody involved in the legal sector, but also so important about you saying about opportunities, you know, sometimes I think I focus too much on the challenges, but huge opportunities for the people that are doing great stuff.
(02:41):
Well, also as you know, people are obviously enthusiastically gathering now lots of conversations, lots of interaction. I was lucky to see you recently in London and I went to relativity fest and then I hosted my own breakfast at link later and then I went to Lexpo and then hosted a breakfast at how top and the one trend that I keep finding is that
(03:10):
as opposed to going to an event to learn everyone is now sort of the speaker right everybody has something to share there's a communal interaction communal like intellectual sharing that's happening so that all of these events whether they're large conferences or small breakfasts or dinners or whatever.
(03:34):
Every each person is there to contribute and to learn as opposed to just absorb knowledge everybody has some experience that's worthy of a peer learning and I love the egalitarian nature of what's happening right now.
It's so funny that accords exactly with my experiences of hosting webinars or planning some stuff around Ilter in person events and I started to call it group therapy sessions because it's just it's it's everybody does have stuff to share but I feel like you know it comes from a place of us all needing to talk to one another you know it's that it is that sort of group support and how are you doing things and and am I on the right page and.
(04:19):
And sharing yeah I think there's a need to share right now and I did joke I had a sort of we normally get quite a lot of people in our webinar hosted one the other day that was quite a niche area and so no less people and I was right everybody is just our little group therapy session everybody ship in.
And it feels like there's a need to do that.
(04:40):
People also want to experiment they want to share ideas they want to share best practices and test it out in a safe environments like we're living all living in a sandbox at the moment just trying something seeing if it works let me try this different tactic or process I tried this I entered this in whatever system and it's not just AI right I mean there's a renaissance in a lot of things happening practice management document automation lots of different things.
(05:09):
And that it's it's almost as if this one massive trend is elevating the entire industry to be more thoughtful about how they work and how they acknowledge the work of others yeah and that's funny actually so perhaps.
Well in terms of I know it's not all about AI but in terms of the AI stuff I've written about recently there people are becoming more forensics so there's been a big steep learning curve but in terms of how they're interacting within the firm and their selection process etc but they really learn now what works and so I was at legal tech talk very recently which was great we can perhaps come back to that as a conference.
(05:58):
But I did an interview with Joe Cohen who's head of innovation at Charles Russell speech and he was sharing about they have just selected Harvey literally I just wrote about it at the beginning of the month and so beginning of July and they did this huge selection process like I think you know there's been a long period of engaging lawyers you know I think it's interesting because I've written about legal tech now for 10 years and and at the beginning it felt like it was a to an IT.
(06:27):
And lawyers weren't really involved you know like that all rarely anyway but now because obviously the change in the type of technology and how it's been used and it's been used is a very much a lawyer's decision so so they were talking about the Harvey process they went through this extremely in depth multi prong selection process where they tested all kinds of different different systems different software obviously comparable and it was interesting that he said they are.
(06:56):
He said they only went with big fenders because they got a little bit burned by they initially chose spring book AI which got bought by clearly and then obviously had to change so so anyway so they but they what was interesting was the depth of the process and the fact that they had all these they had.
(07:17):
So about nine different questions across nine different areas that they were testing and so that was interesting in itself they got lots of lawyers involved who were quite willing you know they were like they're sort of their.
High uses of spring book AI and they came out Harvey is interesting as well from a Harvey perspective because Harvey came out on top of every single category by a significant margin so that's obviously who they went with but it but it's interesting hearing those conversations.
(07:46):
You know in terms of people are this is what people do right they they've been clever at their jobs for years but it was just interesting as to how.
You feel the learning curve right that we're becoming sort of a quite different taking quite a different approach now and before they.
Start talking about tools now they're talking about tactics and processes and use cases which is also a shift I remember being at legal week and meeting with some partners at a law firm and they.
(08:21):
Ask me if I could just tell them what tool to buy and I thought.
What I couldn't even understand why they had immediately you understand why they asked that question but I couldn't understand even why they thought that was the logical question because they didn't say for what you know they just said can you just give us the tool or a list of things that we should just buy and implement and I thought oh my gosh that's not you are not approaching it the right way and we all laughed and then I realize now that more and more organizations are.
(08:57):
Are hearing that and recognizing that it's much more about you mentioned this forensic look it's much more about really opening the hood and trying to figure out how how are we working rather than how does this work then we can kind of figure out what is effective and in fact in a lot of these conversations people may not even mention the names of tools they may just mention we tried this and we learned that this group does it this way and this group is interested in.
(09:26):
This group is interested in this and that we have certain users here and that is really something that is particularly effective which is why I think at any event you go to again small large international local people want to hear specifics and they're not really.
That focus necessarily on the big flashy thing right which is why you're seeing you know time capture and time entry and things that are so standard and legal getting lots of attention because even though they're not super flashy as much as you know something else might be they're really valuable obviously and you know if you can transform something like that it can change everything in an organization.
(10:14):
It's so fascinating so I spoke with Ryan the founder of it used to be time by ping and it's obviously they are focused entirely on time capture and they're doing some super cool stuff and actually that's a fascinating area because people haven't really ever understood time you know they're now as we're moving towards they're really seriously looking towards like flat fees or moving away from the bill of the hour or they can see it on their horizon for a big chunk of work.
(10:43):
They're having to actually really understand the way that they they're way that they bill and also there's a huge amount of un-villable amount of work that you can't charge for and they're really starting to dive into what that looks like and analyze business development and there's so much more analysis behind the scenes in terms of how do we actually work and we need to understand that in order to you know move to a position where we understand our value.
(11:11):
So I'm Ryan's really super interesting on that you know and they've obviously just they've just raised a hundred million dollars which is so really happy for him and it was really nice to see and I saw him at the tech talk as well.
I'll just say that he and you know he's a dynamic entrepreneur who's been committed to this since the early days I met him when he was part of the Lexus nexus legal tech accelerator many years ago just incredible and well deserved success.
(11:38):
I have to say that I love seeing the folks who have been committed to innovation and change and upskilling and improving the profession for so long really being recognized I mean they've been recognized but you know obviously the acquisition of V Lex by Clio is is an incredible milestone in our space but I have to say that I've read the
several posts including by Kevin O'Keefe the founder of Lex blog among other organizations and he wrote something that I think is quite interesting and I think it's interesting and I think it's interesting to see how he did it.
(11:59):
I'm not sure if I'm going to write but that I really resonated with with me which is those leaders particularly Jack Ed and Phil are are really in my you know my experience is so I'm really happy with the
very interesting thing is that I was including by Kevin O'Keefe the founder of Lex blog among other organizations and he wrote something I am going to write but that I really resonated with with me which is those leaders particularly Jack Ed and Phil are are really in my you know my experience just extraordinary individuals like human beings and the fact that they've combined is very meaningful and I just I had a personal connection to that transaction.
(12:37):
When I saw it I wasn't I wasn't home at the time I was away and I saw it and I thought I just I love this these people are just fantastic human beings they've certainly been supportive of me throughout my career and it sounded like you know they have done the same for Kevin and for I'm sure many many others it wasn't as much of the business transaction that resonated there just like you know your admiration for Ryan who's been you know doing this for many many years it's just it's interesting to see the personality.
(13:06):
I just see the personalities behind these developments and just to appreciate their commitment to this change which isn't easy.
No I mean yeah that's extraordinary I'll come back to Jack one second but I have to say I kept teasing teasing Ryan about where's the Lamborghini because obviously he's like shout out.
(13:27):
I've heard from a bunch of friends that you know that it's actually different than it becomes much more accountability right the numbers the numbers really matter they they create a level of accountability that forces.
You know just like a heightened business acumen and focus so I think it's not.
(13:48):
There's no number yeah the the raise isn't the isn't the moment I think you'll have to ask Ed and Phil where the Lamborghini is but I don't think that's their style.
I'm gonna be asking Jack.
Yeah yeah so Jack's a great I mean he's a great leader he's extraordinary you know I'm no doubt talked about him before because it's quite unusual for a CEO founder CEO to get to that stage right that because when you and Jack's obviously raised a lot of money.
(14:17):
And I mean that the acquisition for a billion dollars of Vlex is just extraordinary the money that's starting to flow is just extraordinary when you think about that number right.
And I think he's got the March show obviously what people are trying to do so Vlex is everybody knows combines AI LLM's with data so legal database which is which is currently where the value is in terms of you know really being up to
(14:45):
to apply the LLM to that to that legal database and and Vlex obviously been doing great job is it I mean it's interesting is quite a different.
It's quite different business for clear they're now in the business and practice of law so that's quite interesting that they're combining the two be interesting to see how they do it because it's a very sort of separate area but.
(15:06):
So just kind of curious is to how that will work and know that we'll have lots more conversations in the coming weeks about that I love them as a company and I'm sure they'll make it work fabulously as you say there will brilliant people you know and that is the best start and both teams have a good track record of incorporating the tools that would make them better so.
(15:28):
From if we're going to look at past precedent I think it's a good indicator of what this might look like but regardless of the transaction I think that it's important to acknowledge all the wonderful human beings behind us who have been really committed to the space and.
But it's still the research space just as a side somebody was saying to me they think that I mean in America you've got pace and you've got all kinds of you've actually had much more sort of legal case law such a legislation available or be it for a fee but someone saying to me that they think that going forward in the not too distant future that legal databases such as Vlex such as Lexus will be will be table stakes that actually that it will be available to AI and.
(16:12):
And so it's an interesting it's an interesting acquisition I think it's not going to be the the only one I think I I forecast other requisitions.
I'm going to be say of this because you're so excellent.
But so there'll be I think there'll be others but it's interesting in terms of timing is to how long it will be before actually you know we don't.
(16:33):
But I think this is a timing plane that they're going to have the March right there quick off the off the bat and I'd be interested to see what they do with it but but it's just kind of fascinating time in terms of how what what what is valuable now and what's going to be continue to be valuable going forward I think it's kind of fast.
I think things are going to change quite quickly.
The sand going through the fingers is even moving more quickly because there's more sand than it just pile on it will be interesting to see it's fascinating to me that we are now halfway through the year and wonder what will come you know you mentioned this idea of of the database being all powerful like the center of a lot of this being table stakes I remember being at
(17:17):
the last year and they had a discussion by lawyers and the legal team the innovation team at the European Union who had developed because of the complexity of their and anybody who's ever read the data directive or anything else that's been published.
It's complicated and so they had developed using their repository of complex documents a system a large language model that they were offering to the public because they used public money for it to develop it and it was really really interesting this is tool that you can build on and fascinating to see so I I encourage people to look broadly beyond just the handful of private companies that you see developing this.
(18:06):
Because there's incredible development happening in a lot of different directions and in areas where you might be able to access some of this information in in different ways and you know maybe more broadly.
Yeah, I do hope it's interesting because the spring book example I think it's interesting you know you would hope that law firms continue to work with companies and encourage innovation encourage.
(18:35):
Encourage new companies to come in you don't want to have just a collection of of large of large sort of dominant startups I think that the I think there's two two I've two thoughts one if you look at legal tech hubs map of of companies it's probably unsustainable is the reality so they were this really challenging period for firms where you know you've got so many different companies you feel like that's not sustainable in terms of the size of the market.
(19:03):
Interestingly with private equity so people have different views on private equity I was speaking to someone who said that they would view private equity investment of a company as being a positive thing because you know it doesn't it's not a guarantee but actually private equity is pretty smart where they put their money they they have a model where obviously they expect some to fail but but still nonetheless they said actually that would be a benchmark of we we hope that this will will be a success but it but you know it's it's a real challenge for firms at the moment in terms of who.
(19:32):
They work with right I think that that you know I don't really know what the solution is to that because obviously there been now examples of law firms buying companies which that means if private equity invest that's something different right they can carry on working with them but if law firms start buying them I think that's a sort of slightly more worrying thing so just be interested to see whether that detours law firms from working with smaller companies or or how that pans out when I host my
(20:01):
legal tech mafia breakfast usually in New York I mean I've recently done one in Amsterdam one in London I did one in south Florida but I typically host them in New York City and it's amazing to me the array of companies the sizes the development stage of individuals you know we'll typically have
(20:22):
40 50 people now come to the breakfast and you'll have companies you recognize and companies you have not yet heard of and I find that most of them are on a pretty good growth trajectory obviously the smaller ones I think that that's a
(20:43):
little bit something to watch it seems like there's a lot of opportunity you know the total addressable market in a legal has grown so significantly that that's in many ways one of the things I mean that's one of the things that's attracting and leading to this development obviously I think the barrier to entry is low and the ability to develop some of these tools requires a lower level of capital at this point but there's there's a lot of factors to play but I get this
(21:12):
sense that a lot of the companies that you start to hear about are really thriving and it would be interesting to see on that list because I know that list is is long to see how many of them are sort of completely unrecognizable because I think many of the companies on that list we would we would recognize so it's
the other thing is just to say that I was telling to another founder at legal take talk and they were saying that actually law firms can really help I know this is much easier said than done but he was saying that the sales cycle for small companies is so long and actually the law firms going to get where they're going to get anyway in many cases and actually they
(21:59):
said they really don't have to invest that much you know into in terms of sort of starting to do proof proof of concept and he's saying that they have a big perhaps response to
literally he's not the right word but they can they can make such a huge difference that they don't understand that these super lengthy sales cycles can be actually really damaging for small companies so it's a
(22:25):
little bit chicken and egg but and obviously law firms aren't just going to bundling and you know they've got a lot of decisions to make but it's just something for them to bear in mind I think I don't know if that is really something that a law firm is
responsible for changing I mean you know obviously the law firm has to protect its data its clients it has ethical obligations there's just a
(22:48):
ray of reasons why some of these things take time there are a lot of stakeholders it's an overhead expense I just think that it's an interesting discussion because this has come up the
sales cycle is long it's very hard to break through the noise that you see posts like this I've had conversations with folks like this it's come up in various ways at events that I've
(23:10):
been at and yet I don't know that that's the the challenge that you can work around it's often great product persuasive pitch you know there are different factors but the idea of a law firm reducing
it's cautionary protocols I think is a is probably an area that is less likely to change than than some of these others it's so problematic though you know and it sounds like it's
(23:41):
if you were selling to a bank or to an insurance company you'd be facing lots of the same issues I think yeah that mean but then so I mean I agree they're probably not going to change but but you know it's
chatting to the fact I found out the super successful company that's doing really well you know they're not struggling and we were talking about the private equity thing and I was saying you know about I was sharing the same observation that I just shared with you about you know this this guy who's saying you know
(24:10):
I suppose senior person at law firm the private equity is a good sort of benchmark and you know everyone's private is it's very polarizing right and the founder was who hasn't taken any investment was just so hard of
I do say my goodness you know law firms just need to move faster you know they need to find a way to innovate quicker whether it be small proofs of concept he said they don't
(24:35):
need to spend nearly as much as they think you know just to start testing in a you know like you mentioned the sandbox testing in a sandbox movie there are ways of speeding this stuff up right like actually if you want to be an agile organization then it shouldn't really take I get what you're saying right that
in order to roll out something on an enterprise basis of course you know there are lots of different hoops etcetera but actually just to do sort of small sandbox you know and and
(25:03):
and tests and behaving as an agile organization, which is law firms really need to move towards,
right? And also we move past the idea of IT just being an enterprise saying, right?
It might be that corporate need this and litigation need this and we're going to have lots of
different, and that presents a different conversation and a challenge in itself. But that's not
(25:24):
what we're talking about, it's more like the speed. I think I do feel like they need to find a
way to move faster, not just, I agree, it shouldn't be, the well-being of the startup isn't
their responsibility, but just for their own well-being and ability to act fast for their own
interests, I think, probably needs to do, they need to do better personally.
This has become a passionate topic.
(25:47):
Right, no, it's a really interesting topic. It's come up many, many times and there's a sort of
frustration. I assure you, and I know that you're as deeply connected to this particular community
as anyone, but the people who are responsible for making these decisions or participating in
these decisions would love to make them faster. I deeply believe that. I think that if they had
(26:09):
a bigger team, people who are directly responsible for one thing, driving innovation, even the firms that
have an incredible innovation team are still insufficiently staffed to manage every single possible
idea that could come across. It's on the founders and on those teams to be smarter about how they're
(26:36):
reaching out and to really recognize what value the people that they're trying to reach are most
interested in. You and I both do this. We both try to provide a forum in a lot of different ways to
give a voice to a lot of these organizations. I have a podcast and I have my virtual lunch and
(26:57):
I host a breakfast and I really want those companies to be heard and to tell their story.
I love to hear their story. I learned something every single time I've done, I don't know,
something like a thousand podcast episodes. Every single time I hear a story from a founder
I love to repeat a few years later to see if that founder brought her vision to fruition. I'm always
(27:21):
trying to figure that one out. I host a CEO round table, which I just hosted and I will say that
one of the benefits of convening these conversations is also to connect leaders, but to
have them again, coming full circle to the initial thing that we talked about, which is probably
a good closing point is that people who are doing the same kinds of work and who are challenged
(27:48):
with some of these issues that we're talking about need to connect with each other in a way that
allows them to be candid and to be vulnerable in some respects, which is a word that isn't commonly
associated with the legal profession, but a vulnerability that allows them to maybe see their
(28:11):
blind spots, help someone help them see the blind spot of this is an issue, not of our product
and not of our service and not of our approach. It's because law firms take too long to buy stuff.
It's like wait a second, let's have a conversation about this. How have you penetrated that?
What have you done? Oh, we have this incredible product. Everybody wants it. We're bringing it down
(28:32):
our door. Oh, maybe, you know, so I just think that there's an interesting solution here and that
solution in many ways comes from candid conversation that's honest and sincere.
Well, I always appreciate our candidates and to conversation. It's always a pleasure.
It's my pleasure to privilege, Caroline.
(28:54):
Niche, and we come as much. I know who even knows. We bounce it around. It's going to be hard to
listen to this, but I'm confident that Tom will make it and do his best. Anyway, well,
Caroline Hill, it has really been my honor. I've always enjoyed these conversations and excited
(29:14):
to continue on our schedule here and to just see what the next half of 2025 holds.
And Ari, I look forward to catching up next time when we'll be close to Ilta.
And so we can start to think about what's going to happen there and also we'll be able to get together.
Maybe without microphone. We'll have to bring our flashy microphones.
Caroline, thank you so much. Thank you. Bye.
(29:41):
[ Silence ]
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