Welcome to LEGAL TECHMATTERS, a Litera podcast dedicated to creating conversations about trends, technology, and innovation for modern law firms and companies - big and small.
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Hello, everyone, and welcome to our latest podcast with Litera. I'm Caroline Hill, Editor-in-Chief of Legal IT Insider. And I'm joined today by two really well-known and respected female founders to talk about building your start-up, growing your start-up, particularly within the context of the current climate, the current economic climate. My first guest is Kristen Sonday, who's co-founder of Paladin, which helps pro-bono legal services provider to do more work and better work through the use of technology.
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Hello. Thanks for having me.
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It's great to have you on. Kristen, I'll come back, introduce you more fully. Kristen joined the US Department of Justice and founded Paladin in 2015. And I'll come back to a little bit more about that. But Haley Altman also joins me. Haley is the co-founder and CEO of transaction management platform Doxly which was acquired by Litera in 2019 and is now a Strategic advisor for Litera, but until recently she was head of M&A completing ten acquisitions in 18 months.
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Ten. Yep, that's right.
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It's still very much with Litera but with not as head of M&A but as a strategic advisor. Interestingly Haley has just been appointed to the board of directors at Paladin alongside Cisco's former chief legal officer, Mark Chandler. That was a very recent development, and it follows Paladin series A of $8 million, which is a very impressive amount. So, I think Kristen and I started to talk about your background, I think we would sort of dove into this.
I should just say that through the course of this conversation, we're going to really leverage your experience in terms of talking about starting up and how you're building your company. We're going to be talking about start-up trends. We're going to be looking at fundraising patterns and particularly perhaps in your area of HJ. And also, we're obviously going to be taking a dive into the macro-economic climate, which I know will be very relevant at the moment as start-ups are thinking about their strategy, about whether they eat, whether they start a start-up, whether the how they grow it, etc. So, I'm really excited to have both of you on.
Just to go back to you, because you obviously worked for the Department of Justice, but then you had a lot more experience, didn't you, in terms of learning how to create a start-up? You tell me. Tell me a bit about that.
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Of course. So, as you alluded to, my first job out of school was with the U.S. Justice Department doing international criminal work in Mexico and Central America. So, I was working with the FBI and the marshals and our Mexican counterparts to extradite fugitives back to the US. Very, very exciting. And it's also where I got to see first-hand how complicated our judicial system is to navigate and it's hard enough if you are American and you speak English and if you don’t it just it feels nearly impossible.
So got to see the value of having an advocate by your side to navigate all these judicial processes. So that was really where the kernel of Paladin started. And then after that, I joined the founding team of a tech start-up in New York called Gruber, which we took through Y Combinator, a large, prestigious accelerator program. We scale that internationally and we raised a few million dollars. And that's really where I learned how to build a company from the ground up. And by the time I left, we were in a number of different countries. We had hundreds of thousands of users. I'd hired a team of 30 plus and I was able to leverage what I learned at Gruber to build Paladin, which for me was this perfect intersection of figuring out, Okay, how do we leverage technology to increase access to justice in an area that's traditionally been very under-resourced and underserved so that we can make impact on a meaningful scale?
00;04;16;09 - 00;04;46;29
Okay. Thank you. And I know Haley, you come from a different background, perhaps more similar to my own. Although I wasn't a partner. You were a partner. I similar. And do you leverage your own experiences? I think I've read well, we know each other. You said you did thousands of transactions and leveraged your experience, too. And perhaps again, in the way that Kristen are saying about, you know, really seeing how important it is to have an advocate.
You had an experience of transactions being slow, clunky, quite painful. And so you leverage that experience with Doxly, which you founded. So again, so I guess you both really love your own experiences when you were thinking about what you wanted to do, it was very much came from a personal capacity and perhaps wanting to do better.
00;05;13;23 - 00;05;32;18
Yeah, I think when I was looking at, you know, I'd been practicing for about ten years when I left to start Doxly and you know, I practiced on the West Coast in Silicon Valley and then in the Midwest and it didn't matter kind of what level I was at within the firm as an associate or a senior associate or partner or kind of where I was.
You still see the same complexity. We were trying to accomplish the same things. And so, when you experience the pain and you experience it from different perspectives and by the time, I was a partner, I realized the impact was having on our overall ROI. So, like you see this pain, you know, it exists. You can start to think about how you can make it different.
And so, I think that, you know, I think you hear from a lot of start-up founders, like when you've had the experience, when you've been you've actually you're kind of sitting there in the middle of it and you're seeing the problem from all different angles. You're like, okay, like maybe I can take some time to figure out how to do it.
I did research to see if there was tech out there. I honestly wanted or like, I still wanted to just buy something because I love being a lawyer and I wanted to continue doing it. And I couldn't find anything out there. I could find things that I kind of skirted around the problem, but nothing. And so finally, at one point, I was like, I get I guess like I could do it.
Like, I guess, you know, it's like if I keep seeing the problem and I keep wanting to solve it, I guess it's just now I guess I should do it.
00;06;35;17 - 00;06;36;18
So that sort of started.
00;06;37;09 - 00;07;01;21
You know, is so interesting you say that. So, I've been to quite a few of innovation labs and I've heard presentations from start-ups. And one of the things I think is really interesting was the number of number of start-ups that hadn't done that research without meaning to be critical. But they had just had this idea. They weren't always from the legal background.
Some of them did or mixture of backgrounds. They just thought, hey, we've got this really good idea. And but when I listen to listening to their presentation, and I say, actually, there are things out there already that do that, and that's not necessarily a bad thing. Right? So, I don't think competition is a bad thing. Actually, it can be a very good thing.
But you need to know what you need to do. I just thought the first step is to do really good market research so that you know what's out there. You know whether there's a need for a start. Is that would you say that's a fair point? You really need to do your homework first. Maybe Kristen Go ahead, Kristen, you.
00;07;40;03 - 00;08;03;20
Yeah, absolutely. So it's interesting you see that because you need to have the problem in mind that you want to solve is the first step. But I think there's even a level beyond that where you have to identify what part of the problem you want to solve. So for us, Phyllis and I identify this pinpoint that I didn't even know about, which is that every lawyer in the US has this professional responsibility to do 50 hours of pro-bono work per year.
There's incredible interest in doing pro-bono work. There's so much need. 92% of low-income individuals, civilian needs, are not met or inadequately met. And there was no tool to facilitate the connection between lawyers and people in need. So, we knew that that was a macro issue that we wanted to address because the interest was there on both sides, but we had to go a little deeper and understand what part of that problem we can actually tackle using technology.
So one of the first things that we did was sit down with a number of firms and knock out literally each step of their pro-bono process from beginning to end. On average, the AmLaws were spending 56, they were taking 56 steps from beginning to end to end take a pro-bono case to closing in on and reporting it. And they were spending millions of dollars on these manual programs to help facilitate this work.
And we knew that there are opportunities within those 56 steps for us to jump in with tech and make the process more streamlined. And so really coding that out and identifying where we might be able to leverage technology where there had to be human engagement was an important part of the process to know where to start and continue building out from there.
I don't know, Haley, if you had a similar experience?
00;09;17;06 - 00;09;36;26
Well, yeah, so actually when we did this for eight weeks, so I joined. So I've been building out the idea and then I got introduced to a venture studio that had wanted to do something in legal. And so I actually like literally on giant paper, mapped out the entire process so people could see all the different steps we took and then see like how and they were just like, Wait, what?
And then like here's every part that's like printed, here's every part that involves a scanner and like you saw all these different steps. And so, people could see it. But, you know, I wasn't it's to your point on, you know, if they're, you know, when you do the research and like for people that are like they don't do the research or one like competition is good.
There's also there's also a benefit like if there's something out there in the market that's already starting to be developed also gives you a sense that the product is something that people want to solve and that their people are willing to pay to solve. Sometimes, like I see some ideas and they're like, yeah, that is a problem, but it's not painful enough that people will pay to solve it.
And so I think some of the research needs to be research on the market as a whole. Is there something out there? Is there something that's dominant in the market? Because then it's going to be harder to break in? Or is there any interest in solving this problem if it's a kind of a white space for no one's really kind of jumped in to try to solve it, the research then needs to be, does this need to be solved?
Like does this part of the problem, the part that I think to Kristen's point, this part that we're going to solve, that we can actually solve in the first iteration of our product. Do people care? Will people pay for it? So, then the research needs to be like, okay, talking to people, we did talk to people before I even brought the idea to like the partnership at ICE Miller and told them I wanted to do this on the side.
I went and talked to lawyers, and I think as lawyers, sometimes we get a little sceptical of whether or not we should share ideas with other people. Because what if someone sees that we're all like risk averse and stuff like that? But like, in all honesty, like that is like that. The idea that someone's going to, like jump in and like take over your idea.
I think that's a little bit we get a little too cautious on that. I think there's some things you want to kind of keep closer to the vest, but like it's I think this like not getting advice and not talking to people and not doing the research, both marketwise, but also, you know, kind of firm wise, ah, in-house counsel wise.
I think that's where people start to, like, build things before they know what's needed or what is viable.
00;11;43;04 - 00;12;05;14
So interesting. So yes. So, there's I mean, three things in there that really interest me. One is the fact that you did so much unpacking and really so this is one thing that I see across the board within the legal sector, whether it be, you know, the all firms that are trying to apply technology and that they don't unpack their processes and therefore they don't know how to automate it.
And so that's a really interesting observation. So and I guess, you know, the other thing, it seems very sensible to Kristen. You obviously did a lot of work going to law firms and getting their input, which is essential. But is that is that difficult to get them to give you that time? And I suppose that would bring me onto the third observation and perhaps you could unpack it altogether.
How do you know whether they'll pay for it?
00;12;34;17 - 00;13;09;19
All are really good points and questions? So on our end, I mean, the short answer is yes, it can be difficult to find that initial partner. But there is you know, we're lucky in legal that there is a group of really innovative law firms who are prioritizing innovation and development. And so we were lucky to partner with Dentons as our initial we called it a co-development partner where we essentially deep dove with them for six months on exactly what you were saying, unpacking their entire process and figuring out where we can jump in and leverage technology to streamline different efficiencies.
And we worked not just with their pro-bono counsel who would be, in our mind, kind of the main user of Kellerman's platform, but also other folks who would touch the system. So understanding the council's experience also the attorney's individual experience, how people at different levels within the firm might engage with the platform to really understand what the pain points were across the board.
And then once we had a number of data points around what those pain points were, we could start building solutions in partnership with them to create something that we know would add value at the end of the day. And because they were developing it with us, you know, they were much more inclined to pay for it and so on the pro-bono counsel partner side of centralizing all the pro-bono intake across organizations was a pain point kept coming up because they were spending so much manual time copying and pasting, curating lists for attorneys. They just wanted a one stop shop where they can go like they do to order food through Seamless or GrubHub, or they wanted to call an Uber Lyft.
They wanted on demand pro-bono somewhere online so we could create that repository for them. And in law firm leadership was really interested in the metrics around the pro-bono engagement and what was the business ROI of this work being done since they hadn't had that before? And so I think by taking into account all these different perspectives and working very closely with at least one initial partner, you can more quickly get to what the end solution should be that is validated by the market that they'll then pay for.
And I'm sure Haley you had a similar experience, right?
00;14;38;05 - 00;14;57;21
Yeah, and I obviously like when you know, when you're lawyers and you work at firms like so ICE Miller was amazing at offering a lot of time. And when we did this firm, we get a high alpha when we are competing against their other companies and all these other verticals. And Christian Andersen, who is the high alpha lead on my team, was like, Hey, this is already a business like you already know.
It's like just go sell it while we help build out the deck and put some of the materials together, go get some LOIs. And so, I went and talked. I got four different lawyers and I said, if this thing existed, and I walked them through, this existed. And I were to give you a discount on like unlimited usage for the first year and like, here's the price, would you sign up?
And so we got people to actually sign up when there wasn't a product, when there wasn't something in it to validate the idea that if this existed, they would pay for it. And so we got people to agree to that, and that's what our first customers were. And then they gave us they got a great price for a couple of years and they were able and they gave us really good feedback, but in that instance it taps into like the network of what you build.
And I think I've talked to that a lot. Like creating authentic networks is like I had to do it to bring business and you know, my, you know, to make partner you have to have a book of business and things like that. And so I had to figure out how to do it there. And so building networks, I learned, was so important so I was able to tap into those and say, Hey, can we walk through this?
Can we workshop with this with you? But validating that someone will pay for it. I remember having a client once that had said that they put out a free version of their product and everyone loved it, and everyone was using it. They're like, hey, they went to customers. Like, you get so much value. They went to their highest users and said If we paid for, if we made this paid, when you pay for it, they're like, Absolutely, we couldn't lose access to this.
And so, they were like, great. So, they raise capital and they're like, Okay, we're going to hire more people. We're going to turn on the paid version, and then no one paid for it. And they were like, what everyone said they would. And it's like, no, until they put the credit card down. The idea that they say they'll pay for it isn't necessarily what it's going to be.
And so I think that's what you hear a lot in the software space about Agile development. I need to get something in front of people that they can see that they can touch, and then they can say, Will you sign an LOI for this? And I will give you something. I will give it to you free for a year if you use it.
But this is what the price is based on. So you've got to get someone to the point that they'll do a pilot with you, that they'll that they'll share it with you, and then you can start building a little bit more because it's it is hard outside of working with like a Y Combinator or some great accelerator that can help you figure out how to build some of the business components of a lot of money and a lot of work to build these things out.
00;17;19;27 - 00;17;56;00
Yeah. The freemium model is beset with challenges. I think to be completely clear, I guess calling it a pilot know that I know you have to get people on board and they have to work out that it meets their needs, etc. But I guess calling it a pilot rather than going down that very risky freemium route is probably the best and sort of getting, as you say that really paving the way, you know, making it very clear what the sort of roadmap looks like in terms of and then so when it comes to obviously, Kristen, and you've just done a fund raise, Haley, you've been involved in the M&A side of things for a long time. What should so perhaps, you know, talk about the series at first, then we'll come to you, Haley, in terms of your sort of the way that you receive things on the other side when you're looking to buy companies. So, what did you have to think about, Kristen, in terms of going out to the market and raising capital?
What were user key priorities and perhaps things to avoid as well?
00;18;24;00 - 00;18;55;16
So the number one thing that investors want to know is how big can this get. Right. And we have a sense oftentimes of how legal tech tools can use as a legal. And for us, it was important to demonstrate that we could build a really incredible impactful, scalable pro-bono management platform. And in addition to that, we could build things on top of it to help facilitate better and more frequent, pro-bono off the platform.
We might be able to leverage what we were doing for professionals outside of legal to get involved with either legal pro-bono work in other ways or other types of volunteer work. And then longer term, thinking about tools we might build not just for pro-bono lawyers, but for individuals in need to help them help themselves or all different ways that we have been exploring with investors how we can leverage our technology outside justice, pro-bono wedge And so thinking about, you know, number one, how do you make sure you're adding the most value possible within your existing market and the number to thinking about how you grow outside of that were things that were very top of mind for us. And it's both a challenge and an opportunity that Justice Tech has been so underfunded and under-resourced in the past because there are so many different ways that we can grow in so many different things that we can build. But making sure that we have that focus now so that we can grow faster later is something that's been very top of mind.
So that's what a lot of the conversations that we had were about. And I'm curious on the M&A side, how Haley thinks about it. But right now we're laser focused on legal firms and corporates and bars and legal services organizations at law schools. And then it will be thinking about kind of other adjacent markets as we continue to grow.
00;20;14;26 - 00;20;49;00
Because, hey, you know, I've met you at conferences where you've been like scouting and, you know, you've obviously applied quite, very different start-ups really, actually. But what do you think you know, in terms of, you know, you've perhaps raised capital, you're growing the company, you want to know everyone wants an exit in the short term, but you know, what were your sort of what was your third list or less in terms of when you were thinking, is this is this something that we might be interested in investing or acquiring?
You know, what were some of the things that were really positive, attractive, and some of the things which would really turn you off?
00;20;55;29 - 00;21;16;12
Yeah, well, I think a lot of it when you're a strategic acquirer, and not like a big E fund acquiring directly, you're kind of looking for different things, different things that meet your needs. Like, is this going to help us? Does this expand a workflow that we already have that we're already in and we need this feature is just like we can't build it fast enough and they've built like the best in breed technology.
So like there's or is this going to expand our footprint and get us into an adjacent market or complete a workflow in the existing market? Because like Kristen mentioned, that beginning if you're solving one part of a product problem and we have a product that solves one part and you this new company solves part two, that's another thing that's interesting to us.
And then there's always that like, hey, we want to get into a new market. Like when we went Micron in the talent put us, etc. in a different market, they expanded our footprint. So we're looking at things from like kind of how they fit into a strategic plan so there is a part of it that when we're looking at a company, that company has to fit somewhere into like the strategy that we have or what we're trying to accomplish.
But when they do fit into that strategy, you know, we're looking at a couple of things like one, for us, we're always looking to see, you know, they have to have a chief product market fit. We want to buy the best in breed technology. You want to bring you want to bring really great things together. So for us, customer feedback, understanding how the customers view the products, like what is that MPS score - for PS/Ship, when we acquired them, they had an EPS of 96 and something I'd never seen before in a product ever. And like, I mean, and that was true every customer we talked to, without a doubt was like, this is an amazing company, this is an amazing product set. And we were fortunate to bring the team and then they had like really great leader, you know, they had a wonderful founder in Peter, but Nick, who had been kind of running the day to day of the business, was amazing.
And so we looked first like, you know, is this product meet the needs that we have? Do customers really love it. And then do we have people that have great expertise that can come with us on this next part of the journey. So, team is really important as well. Obviously, financial metrics, now in civil in different tasks like verticals outside of legal different numbers may be more important.
So, areas important, we want subscription-based revenue. We want that repeatability. We're not looking for kind of one-time revenue where, you know, you have kind of the one-time bounce and hits. So, we want to see recurring. We also want to see really good gross retention and net retention rates because that's really that sign that customers like it and that they truly have product market fit.
So those are two numbers that are always going to be important to us. Like can you keep the customers that you have and then can you expand them? That's like an added bonus. So, if you can land with the customer and continue to expand, it's always easier to expand revenue within a customer by selling them new products or expanding the seat count because it's like it makes more sense for the whole firm than it is easier to like bring in an entire net new customer.
So, we look for things like that. And so, it's just like these metrics that say the company is stable, they're growing customer feedback just is a huge, huge part of it. Like do customers want to continue working with them? And then we look at how this integrates into our business? Do we're selling to the same customers, we're all selling the right things.
And so, we'll build out different scorecards of what we're looking for, what we want to see in the customers that we have. But for start-ups, I mean, I think there are different points in time that it's going to make sense to exit. You'll have these inflection points, you know, before you do a Series A, before you do a series B where you're going to be in a position.
But it's making sure like you understand the numbers. Like do you do you have a good pulse on what your customers feel about you? Do you have a good sense of what your roadmap is going to be and what customers expect? Are you able to retain people and can you grow that? Can you grow the accounts? And do you have a vision of where you would take this company?
Because, you know, sometimes we're looking to buy that specific point solution, but sometimes we want to see the vision. You don't have to build it. So, to Kristian's point, you have to stay focused. If you want to build out the problem that you're trying to solve and be laser focused. But it's always good to know where you can go and how this continues to grow and how the acquirer can take the business forward and continue and to continue to expand it.
And I always ask every person I'm selling to, if I gave you an extra million or $2 million, what would you do with it? Like so understanding what the needs are, how you grow your business is always like an important thing. Like what? What would it take to get you to that next level? Because any acquirer wants to continue to grow the business.
We're looking at a strategic hire is looking to continue to increase revenue to increase value. So we want to know what is it going to take or what those hurdles that are keeping you from having that exponential growth.
00;25;46;20 - 00;26;09;08
Okay. So, one of the hurdles for people now depends on which area, you're right, but with so much global economic uncertainty right now. So I imagine it must be for people who are some somewhere down the road which creates a niche of launching a new start-up. You know, it's a daunting time, right?
So certainly in the UK where we don't even have a government and we do know sometimes we do, sometimes we don't.
00;26;18;06 - 00;26;19;23
Like the first one is broadcast.
00;26;19;23 - 00;26;22;24
Airs. Whether you will or not, we don't know is.
00;26;23;02 - 00;26;42;05
You know, it's pretty guaranteed that it will change, but they're talking about the climate, the economic climate. So, where what do you see? Where do you see clients buying or not? What are your thoughts in terms of where the investment is going or will be going?
00;26;43;04 - 00;27;00;08
Yeah, I think from a general market perspective, if we look broader, I think I was surprised. So I've done a lot of conversations with people and I've in law firms and in-house, and I'm surprised that people are still bullish that this spending on tech is going to continue I think they're I think people want to solve their problems.
Like the retention issue has been a massive issue. So like firm retention rates are still going low right now. Obviously, that becomes less of an issue in our it's go down and you don't have as much work to spread around. So like people aren't like underwater as much. But like I mean, like legal continues like work shifts usually like work continues, but it'll shift from, you know, maybe it'll shift from M&A into more litigation.
It'll shift from M&A into bankruptcy or distressed financing. So like work continues, it just shifts like where it's going. So people have to be a little bit more nimble in terms of how to do it. But I've been pleasantly surprised to hear people thinking that the tech spend will continue. I think what's going to happen is it may slow, may take longer to get contracts through size of contracts may be lower to start specifically with the new technology, as people are a little bit more hesitant to like buy in.
But I think what's going to be important for the start-ups and, you know, is to say, okay, I've got to come with a real clear understanding of the value proposition that I'm finding. So really understanding of who do you actually need to sell this technology to? You don't have time to kind of figure it out. You got to figure out who is the real buyer of this and what is important to them.
What's the ROI? We can show as to why they need to buy this. And I think that's where, you know, Paladin with the pro bonus has a really interesting angle on the fact that it can help people retain attorneys. It help people train them, especially if there's not like big litigation that's in courtroom, you can actually get your litigation experience and be in a courtroom and do these things.
So I think there's more opportunity to think about how do we train people, how do we teach people how to people learn so that we can retain attorneys and retain knowledge in the firm. But I mean, I think it's going to be I think people are going to be more picky where they're not going to be like, I'm going to try we're going to do three pilots of three competing technologies.
They're going to do one, they're going to do what they're going to like. They'll look at it and they'll be more deliberate about what programs they take forward. But you may see a U.S. U.K. split. I think U.S. has been a little bit more or less pushed decisions out. U.K. It's been a little bit more. Let's keep going and rebuild our processes.
00;29;08;07 - 00;29;17;28
To benefit. So the fact that theaters are a little bit quieter in terms of the pro-bono sector yes.
00;29;17;28 - 00;29;46;03
We actually do see pro bono rising pretty significantly when there is an economic downturn because there are fewer billable hours, which means more time freed up for pro bono. So definitely an opportunity to get involved with causes that you're excited about and, you know, develop your skills network with other colleagues, etc. So never, never a good thing to have an economic downturn, but it does mean more time available to help others, which is a good one.
So definitely look at that. And I think, you know, on the start-up side, it's important during these times to stay flexible. So, you know, if the firms are going to do one pilot versus three, you want to make sure you are that one. And so being flexible with your terms and how you partner with firms and really working closely with them to identify their pain points and solidify that
ROI, the value for them is going to be of utmost importance.
Another thing that I'm hearing is that with respect to fundraising, round sizes overall are down, valuations are down. Typically in venture, you want to move as quickly as possible and increase your burn so you can grow very quickly. And I think now entrepreneurs are tending to be a little bit more conservative and more intentional about their spending so that they can extend their runway and hopefully get to profitability.
So, they have optionality. So, we're seeing a trend towards greater profitability and more just consciousness around spend and then making sure that you are laser focused on bringing on the right clients and partners that you can continue building for the long term. Those are all important things that I've heard from folks in our space.
00;31;03;14 - 00;31;30;02
Look, we unfortunately are out of time. It's been so useful. I hope start-ups listening in, it's invaluable in terms of perhaps being thought provoking of law firms and thinking about perhaps the challenges that facing the people that are really sort of trying to push the boundaries in our market who obviously need to be continued to be supported regardless of the economic climate.
So I hope that's been valuable for a lots of people listening in. I really appreciate your time both of you. Thank you so much. Kristen, I wish you well in growing. It sounds like it's going to be a really good time in the market. And Haley I look forward to hearing more in terms of you working with Paladin and obviously other companies, in your capacity as strategic advisor.
But for now we have to leave it there. So, thank you both so much.
00;31;58;06 - 00;31;58;16
00;31;58;27 - 00;31;59;15
This is great.
00;31;59;20 - 00;32;00;22
Thank you so much.
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