Ep 64 of the Legal Tech StartUp Focus Podcast -- Time, Money, and AI – Ajax’s Mission to Modernize Legal Timekeeping
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Hello and welcome to the Legal Tech Startup Focus podcast. I'm your podcast host, Charlie Uniman. On this podcast, I'll be interviewing the people who build, invest in, comment on, and use the apps made by legal tech startups.

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Hello, everyone. This is Charlie Uniman, your host of the Legal Tech Startup Focus podcast. And I am, as I have been with many of my guests, especially pleased to bring to the podcast a startup founder, co-founder, in fact, of a company called Ajax.

a timekeeping solution for law firms. We'll get into much more detail about Ajax. So I want to welcome that co-founder to the pod, Jack Weinberg. Hello, Jack, and welcome. Hey, Charlie. It is really good to be talking to you again. Yeah, we have had a chance to talk before, Jack and I, to tee a few things up.

and learn a little bit about each other Jack's co-founder I will point out is his brother if I have that correct and I don't want to steal Jack's thunder because there is an interesting founding story but neither Jack nor his brother is a lawyer good for them but they have built quite a nice little product here that has big ambitions as it's doing well tell us Jack about

about the founding story. I loved hearing it first when we'd spoken. I'm sure the listeners will like hearing it too for the first time. Sure thing. So as you mentioned, my co-founder is my brother, Alex, and he asked neither of us as a lawyer. The main reason for that is because both our parents are lawyers and I'll be totally honest with you, Charlie, they told us that we should probably go find another line of work.

So I went into finance, my brother went into tech. I was in banking and private equity. He went to Amazon to do distributed systems. Then he quit that to be the founding engineer at a startup here in New York.

And over that time, we both just caught the startup bug. We were constantly going back and forth about ideas. We tried a couple sort of toy ideas. We both quit our jobs at the same time in October 2022 in order to pursue an idea that was frankly not this idea. I thought that I had this brilliant, brilliant conception for a piece of software for construction equipment mechanics.

And we spent about three, four months just diving in, building software for construction equipment dealerships, people who sell tractors and backhoes and excavators and such to better manage their inventory and help their people get what they needed. Turns out, you can't see me right now, but I do not look like a guy who belongs in a construction equipment dealership. And my brother, bless his heart, looks even less like that.

So that did not work so well for us. That world somewhat chewed us up and spat us out. So, you know, we were kind of wondering, all right, where do we go from here? We have self-funded this kind of nascent and not super well-fitted startup for a couple months. And while we were kind of casting about wondering, should we go back to our former careers? Should we try another idea? My brother,

was sitting there watching his girlfriend do her hours on, I believe it was a Tuesday night, and they were supposed to be going out to dinner, but she got this snippy email from her boss, whom I won't name. And he said, hey, your hours are late for last week. Your billing deadline has already come and gone. You need to get these in now. And so instead of going to dinner, they sat there and Alex read or browsed his phone or what have you. And his girlfriend, Alana, was

Look through her app box and then she looked through her call logs and then she looked at her calendar events and then she wrote up all her narratives and then she released them and made sure that they were compliant with the guidelines.

All of the stuff that you know how to do, that's what doing your hours looks like. And it took her over an hour on that Tuesday night. So not only were they horribly late to dinner, she was unhappy. My brother was watching her saying, are you kidding me? Is every lawyer in America doing this every week or else they don't get paid? And we asked our parents and the answer is, yeah, absolutely. That's the case.

And we said, okay, here we go. This is a real idea. People we know have this problem. Let's go build this. So that was the idea. Do you want to hear about where we went from there? Well, yeah. Why don't you continue? It makes me remember, painfully remember, how difficult it was to deal with the billing requirements of being a practicing lawyer. But yeah, do continue. And I'll interject a few things as you proceed. Go ahead. Okay.

Yeah, so we spent quite a while prototyping a piece of software that would sit on the lawyer's computer, figure out what they were working on based on the actual contents of their screen. So reading the text that they were working through in their documents or in their emails, their calendar, whatever, and then match it to whatever clients, matters, contacts, et cetera, sat in their practice management software and basically create a timesheet for them.

That is a particularly hard problem because as any lawyer will tell you, billing is more art than science. So this wasn't a one size fits all problem. We were also two non-lawyers who were trying to launch untested software that had access to every single thing about a lawyer's day, which is incredibly secure data for the lawyer and for their clients and convince a law firm to use us.

So for about eight months from there, we just tried to figure out what the software should look like, tried to get it right, and tried to convince literally just one law firm to adopt us. And we talked to, I think, 200 plus law firms in that time.

I was biking around Manhattan. It was summertime at the time. I was wearing a suit so that I looked presentable, and I was probably taking four or five coffee meetings a day with anybody who had graduated Yale, which is my alma mater, or Bowdoin, which is my brother's, or gone to our high school, or had any degree of connection, just begging, borrowing, or stealing time, advice, and trying to get our way into our first customer. And throughout this whole time, we were not funded.

So we were basically down to our last couple thousand dollars in our company bank accounts. We were in a horrible mood. We were about to give up and basically go call the entire last year a loss and say, all right, we're going to start over, but just with a lot fewer savings between the two of us and be extremely unhappy about the fate of this. I remember literally having this knockdown drag out argument with my brother.

where we were thinking about going to ClioCon 2023, buying tickets for it, buying hotels, et cetera. My brother pointed out that that price would be about three quarters of the money left in our company bank accounts. And I said, it's always worth going to conferences where the majority of your customers are going to be and people are telling you that they are tech forward, they're interested in technology. Like this is probably the place where we can go find ourselves our first customer. And my brother said, you're an idiot. We need to be saving money right now. Why do I, why am I even in business with you?

And for about a week, we went back and forth on this. We were furious. We screamed. We barely talked. I eventually spent the money, basically just pulled it out of my own bank account because I didn't even want to have the fight. Went to ClioCon.

Long story short, we got our first customer. We got a very, very small piece of revenue from that. We used that to raise money from a series of angels who had been lawyers at various points or sold legal tech companies. And then from Bloomberg Data, Bloomberg's VC arm, and used that to basically hire a team, go get ourselves a whole lot more customers and professionalize this whole thing. But we came very, very close to dying. Yeah, well, that's not uncommon in the startup world, but...

And likewise, and I'm sure our listeners who are startup leaders know this, the fact that 200 contacts over a period of time to figure out what it is you want to do and get feedback sounds like a big number. Believe me, it's the right number.

Because if you're not out there pounding the pavement literally or figuratively over Zoom and getting as much iterative feedback that you can, you're really not making the best use of your time. And hearing you say that you were in a position where after you got your first customer, you could pull in some angel money

from lawyers who are willing to give you a flyer, take a flyer on you I should say, and also eventually get an institutional investor such as Bloomberg Beta to come in. Pretty well establishes the fact that your 200 coffee meetings, sweating around the city in a suit during the summertime, that was time excellently spent.

So take heed everyone, that's the way to go and I wish I could say you could avoid it, but from my own startup experience many years ago and from Jack's, it's almost unavoidable unless you're really, really lucky.

So let's talk a little bit more about Ajax. I've looked at it online. We had you demo it a little bit for me. This is an audio-only podcast. Someday I'll perhaps have a video version, and we'll be able to show a little bit of what's going on. The fact that it connects to the practice management system

The fact that is, I think you told me when we spoke previously, the AI used, and yes, you do use machine learning, has been trained to understand some of lawyer speak. That's got to be a very important aspect of what lawyers found attractive. No?

I'd say I've learned to, you know, the hard way, because I love talking about cool technology, that people don't really care about what we built or what the features are. They just care about their problems. Good point. The problems that they have are...

Just to throw three out there, tracking your time takes time. That's the one that Alex saw when he was watching Alana do her hours. It just took her over an hour to do a week's worth of time. That's four hours a week. That's 16 or 20 hours a month. That's, you know, multiplied by her hourly rate, you know, many thousands or tens of thousands of dollars just being dropped, basically an invisible write-off.

There's that one. There's the pain of actually spending that time. That's time you want to be spending with your kids or catching up on sleep or maybe just doing billable work. There's the second problem, which is you actually lose hours. Like we've done a survey of all of our customers and all of our prospects. We've got hard numbers on this. The average lawyer is dropping two to three hours per week. That's literally, you know, every single day they're leaving 30 plus minutes on the table of, of,

time that they could be billing, but because they're moving between things quickly, because the job of a lawyer is to just be fragmented and give attention to several matters at once and answer slacks or teams chats,

emails, phone calls, document drafting, et cetera. That stuff just slips because you're not going to start a timer and write a narrative for work that only takes you three minutes. It's not an efficient use of your time, but that's billable work and you're failing to get paid for it. So that's problem two. And then problem three, and Charlie, you were actually the first person to allude to this when we first talked.

It's the timing of collections. So Jack Newton of Clio brought up a really interesting point, you know, a year ago, which is the Foonberg gratitude curve.

Without getting too wonky, it's the idea that if you send out your invoice two months after the client actually had the work done and had that positive resonance with you, you're the lawyer who did the work they needed and they're happy about it. If you send it out then, you'll get paid. If you send it out two months later, they'll be thinking, who is this guy again? What have you done for me lately? Why do I need to pay this whole amount? Right? So you, this, and everyone, every lawyer that's, you know, been in charge of billing knows this.

The longer you wait, the more write downs you have to take, the less collectible that money is. And so having something sitting in the background actually tracks the time for you. And that allows you to shorten that time. No, I heard you say two to three hours a week per lawyer. And that, you know, that's significant. But then when you think about

Well, that's one lawyer. Have a firm of 10 lawyers, think about how many hours are being dropped. A firm of 50 lawyers, a firm of 100, a firm of, well, you name it. That's mucho dollars that are falling to the floor and slipping through the cracks in the floor, never to be found again. So yeah, God, that is a real pickup.

in potential revenue for a firm. And yes, the Bloomberg gratitude curve that you just mentioned, we saw that in practice when I was billing and dealing with clients. But the mantra in the firms in which I worked was if you don't bill it,

If you don't have the billings in your system, you can't send a bill. And if you don't send a bill, you're not going to get paid. So just the sooner you send a bill, the more easily or more readily or more quickly, the word is quickly I'm looking for, when compared to sending it, you're going to get paid. And cash, you know, you can't spend receivables that are uncollected. You can't pay your mortgage with it. What you want is cash in hand.

So, you know, as a lawyer who has said this before about other apps, and now we'll say it about yours, you're doing God's work. Because for a lawyer, after doing a job well done, you want to get paid. And what you're, with Ajax, doing here is mightily contributing to that effort.

Let's talk about where you're targeting this application, Ajax. What kind of law firms are you aiming for? What kind of law firms have been your customers to date? And you have been in the market, if I recall, I think about nine months or so. And are you looking to Canada, to the north? Are you looking around elsewhere outside the U.S.? Tell us a little bit about that.

All good questions. So we started with, as I mentioned, whoever we could convince to be our first users. We had a pretty tightly scoped data for the first couple of months where we just had people who were working hand in hand with them, making sure the hours were

looked great for them. And we expanded out practice area by practice area, use case by use case. So getting used to Mac, getting used to Windows, getting used to Teams, getting used to Gmail, to Outlook. There are a lot of different ways that lawyers go about the day to day of being a lawyer. And that's even within a practice area, right? Every patent attorney does not look like every other patent attorney. They certainly do not look like every criminal defense lawyer. So that was the first couple months.

Where we're at right now is we're selling to midsize and large law firms that use cloud native practice management software. The reason for that is because Ajax deploys really smoothly. So the install, the setup, learning how to use it, getting ROI out of it, all of that takes a couple of days at the latest, right? Like we've had people log in and find themselves $1,500 of extra billable time within the first two days of using Ajax.

And we can't do that if you're using on-prem servers. So for better or for worse, we're working with people who are tech forward, who are using cloud native practice management software. And right now that is Clio primarily. So they're our best integration. They're the people we're looking to work with the most. Well, you're skating to where the puck is going because...

As I mentioned to you, I think I did when I started out and our listeners have heard this, 10 years ago with a startup, we were cloud only. And it was much too early, even a mere 10 years ago, to be talking to larger law firms about the cloud. I'm on my hobby horse. Yeah, I think the cloud is secure enough, reliable enough.

and better managed than most law firms can manage their on-premises service. So you should be good to go with that, especially as time goes by. Have you looked abroad to Canada, to the north?

neighbors up there we're actually piloting with a canadian firm there in alberta in two weeks so yes canada us like those legal systems are there are of course some differences but our products can handle both i would say the english language is the core commonality that you're looking for yeah australia although your support hours may be a little bit wonky we can sell to you if you're in the uk in canada in the us if you're in mexico maybe come talk to us in a year or two

Right. Yeah, I think that should be on your development punch list because a lot of lawyers around the world are facing this problem and could use every bit of help they can get. How did you come to learn the importance of something that I've been, again, on a hobby horse about? And that is the importance of keeping it simple for the lawyers who

certainly spend a large amount of time very attentively focused on their work, but when it comes to learning software, didn't go to law school to do that. How did you get that

mantra, keeping it simple, making the onboarding easy, you know, planted in your head since you, you know, you had parents who were lawyers, but you didn't see their work day to day. How did that come about? Because I've looked at the app and it is straightforward and it is intuitive and that is so important. We are really fortunate to have a suite of advisors that has done this for a lot longer and at a much higher level than we have. So we're able to lean on the best.

From a legal perspective, that's Karen Silverman, who ran the San Francisco office for Latham Watkins and has been doing this for 20 years. She now has her own private thing where she advises Fortune 50s and governments on AI posture. We also work with, and most saliently to this question, Josh Abrams. So he was the head of product at DoorDash. He was the head of design at WeWork, at Ironclad, the contract software, at Trader Joe's.

I'm missing an important one. PayPal, you know, he has done this at an extremely high level for an extremely long time, designing products that users love, that they can understand intuitively, that have absolutely no friction to getting on board. I'm not sure if you've used PayPal, but it's used by people in 200 plus countries to wire each other money because it is very simple and you can understand it no matter whether you are used to ever using a computer in your life before.

Similarly, DoorDash is made for people who barely speak English, but they can make incredible food and they can get onboarded in a day.

And, you know, the drivers, the people who will order, who are, you know, doing it in the 15 seconds they have between answering emails. Like these are products that are not enterprise grade, like, you know, 15 day installation, you know, several calls, a bunch of fees. These are products that are made for someone to just download from the app store and boom, you're ready. So Josh advised us to do a couple of things tactically.

One was just reframe the way we approach the product. He said, nobody owes you anything. Nobody cares about your products. Nobody cares about your name. Nobody will give you a speck of attention until you engage them, tell them what's in it for them and hold their hand through what is hopefully a very short process until they are up to speed and give them rewards the whole way. So what that looks like for us is right off the bat, before we even get anybody to actually set up the app, I just convinced them that this is worthwhile for them. And

And sometimes it's not. I'm very happy to let people say, this is not for me. But what that looks like is walking them through a bit of an ROI calculator survey where we do a deep dive into their firm. And I find for them, here's how many hours are actually being written off without your knowledge of it per attorney per week. And that number, just once you realize how big it is, it's like a leaking hole in the bottom of your floor. It's like you're dripping money like a sieve.

And that suddenly motivates people to spend 10, 15 minutes it takes to get set up. So that's thing one.

Thing two is just from a product perspective, right? Simple is perfect, right? Like it doesn't matter if you have a hundred million bells and whistles that are customizable, people just want it to work for them. So the more things that we can put on ourselves as a team, like if there is customization or tweaking to be done for a lawyer specific use case, that looks like somebody at Ajax, basically in the first day after someone onboards the

The pulling levers in the background saying, you know, okay, it looks like this attorney frequently has a Word document called Document 1 in which they track their scratch notes. And so, you know, we should assume that that is not a specific piece of legal billable work for a client, but it's rather internal administrative work. Things like that. We don't make the lawyer do that because nobody wants to do that kind of setup in order to get value. They just want to see it work.

So the other thing we've done is work really, really hard to make it contemporaneous. So rather than, you know, like having to wait till the end of the day or the week or the month to review your hours, literally when you turn on Ajax within a minute or two, you know, you check the website and it starts like throwing time entries at you for what you were doing in the last minute or two. And once people see that, it's kind of magical, engages them and it makes them want to see more and keep logging in.

So those are some key ones. And then just stealing design patterns from common DTC, you know, popular apps, right? So we're not stealing from IntapTime. We're not stealing from even Clio, as well designed as Clio is, right? We're stealing from...

AI budgeting software that is sold to people through the Apple App Store. We're stealing from DoorDash, from PayPal, right? Because those are patterns that people know and love, right? Like the net promoter score for any consumer app is much higher than for any enterprise app because those are made with love and care.

Yeah, it's not wasted on lawyers, believe me, that love and care. And you're in the enviable position of being able to talk hours and dollars directly. So you're calculating an ROI that isn't very fuzzy when it's very sharpened and very much impactful when you talk about those dollars that are being dropped to the floor and seeping through the cracks. And I also liked...

And I want to point out to the listeners that among your advisors, you mentioned, is someone who is just experienced in app design for B2B users. And not necessarily someone who, like the first person you mentioned, is a lawyer, but is instead just an expert lawyer.

in designing applications that anyone and everyone would feel comfortable using and, dare I say it, even enjoy using. And I think that's a word to the wise among the startup listeners. If you are going to go out and get advisors to help you look for people who are outside of the law but instead bring design, the most important feature of any application,

of any application, whether used by lawyers or not. That brings design shops to the advisory role that they can play for you. So that's great. You know, when we talked previously, I said that I often ask, and will ask now, what is it about the journey to date?

that has made you most proud, that you've enjoyed the most as a young business person. And I think it involved, and I'll let you take it from here, a particular customer's reaction to the use of your software.

Yeah, so I'm going to have to wash my tongue a little bit here. I'm an extremely competitive person. This is a thing that I try to hide. My brother and I, we were both the kids that were crying at the end of every race that we didn't win and would go run wind sprints on our own at 6:00 in the morning until that never happened again. So we like to see the results and the rewards of our hard work.

And there was this one customer where they let us know very early in our pilot with them that they were also piloting another AI timekeeping software. Had a fairly similar value proposition. The actual technical specs were somewhat different. What they did was somewhat different. But they were promising a similar thing, which was finding you extra hours that you were dropping and leaving between the cracks or between the couch cushions.

and making your lawyers time keeping a little bit easier while finding you extra money. And so about half the lawyers at this firm were using us. About half the lawyers at this firm were using them. I'm not going to name names.

And over the course of two weeks, we basically just didn't sleep. I spent until 4:00 AM every single night making sure that the hours for these attorneys looked extremely good. You know, making sure that all the features that they wanted were built, that I was checking in with every person every single day. And it was risky. At various points, I was pretty confident that we were gonna lose this one, that that was gonna feel terrible, that, you know, it would be a talking points that this competitor could use against us forever.

And it turned out that we won. They basically stopped using the other software. They've adopted us internally across the board. And some of them have liked it so much they've invested money. Their firm has actually invited us down to go visit with them. So spend an entire week working out of their offices and hanging out with their attorneys, just learning more and building features in tandem with their specific requests.

Like they'd become one of our core thought partners and one of our favorite customers. And that was frankly just the result of my brother and I just not giving up on it and being absolutely maniacal about making sure this customer had an amazing experience. Nothing like a bake-off, as we used to say, to help figure out where you stand in the marketplace. And I think our listeners have heard me, you know, kid on the level, you know, you've got product market fit.

When you ask a customer, how would you feel if our product just disappeared from the market? And the customer's response is awful, awful. And I'd only allow someone to pull your application away from my hands if I'm cold and dead. So if you get that kind of feedback, and I encourage you to do everything you can to continue getting that kind of feedback, that's just awful.

That's something to be very proud of. Yes, I applaud that. And as I've said so many times before, oh, if only these tools were available when I had to remember what I did during the day. And let alone, I was pretty good at timekeeping, as I may have mentioned to you, let alone some of my partners who were a little less punctual and engaged in what I called creative writing at the end of the month.

Charlie, that's a really interesting one, by the way, because it is often one of the reasons that people bring us in. A lot of the time, the person we talk to is not the person that needs Ajax the most badly.

Most people get some amount of value out of it, right? Like nobody is really tracking off 100% of their emails throughout the day. But the person who is on the ball, who is going and looking at new tools in order to help them capture time, that person's often already pretty good at capturing their own time, right? They're a type A person who thinks about their law firm like a business.

But that person is probably not blessed with all of their associates, their junior associates, their senior associates, their partners, and especially their partners. - Especially their partners. - Yes, yes. Especially their partners.

Often we get brought in basically as a please help me. You know, we've had every partner meeting for the last five years, we've gotten on this person, and it usually is a guy, we've gotten on this guy to get his hours in on time, and he hasn't and it's costing us money. We can't use the stick, the stick doesn't work, we need a carrot. That's right.

Well, and I'll pick up on a point you made earlier too. Even if you pat yourself on the back and say, I'm pretty good at keeping time punctually, it's still laborious, it's still grunt work, it's still not, well, it's hardly fun, it's awful work. And to the extent that you could be assisted by an AI and a tool to help you offload some of the non-creative knowledge

aspects of practice, the grunt work, to put it bluntly. Even if you're good at keeping up with it, that's a load off your back. You didn't go to law school to track time. But an AI that has been built to do it, that's its purpose in life, its life, and it ought to be doing as much of it as it can. And you come in, of course, as a human being in the loop and make sure that what eventually goes out to the client makes sense, but with a big lift, a big assist.

from the AR. So if people want to reach out to you, learn more from you about Ajax, how do they get you? The best way to get in touch with us is our website. So joinajax.com. That's J-O-I-N-A-J-A-X.com.

You will see a bunch of testimonials from our customers about why they love us. And that's one of the things I'm most proud of. My second answer to your question would have been, you know, the things that our customers say about us are just unbelievably nice and warm my heart. So go, if nothing else, go check those out and see what you're missing. And if you want, book a demo and I would love to show you what you're missing and hopefully get you to be happy Ajax customers.

Very, very good. Jack, pleasure talking to you once again, I say at the end of every podcast. And we have no excuse, you and I. We're only about 40 minutes apart. You're in the city, I gather, and I'm not too far outside. We should meet at one another for coffee or drinks and certainly get together at a conference in New York. And...

And until then, when we do meet face-to-face, take care. Thanks for being on the podcast and look forward to meeting you in real life. Yes, sir. Have a great day. Thanks for having me. My pleasure. Thank you for listening to the LegalTech Startup Focus podcast. If you're interested in legal tech startups and enjoyed this podcast, please consider joining the free LegalTech Startup Focus community at

by going to www.legaltechstartupfocus.com and signing up. Again, thanks.