Neil Patel

I hope you enjoy reading this blog post.

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Reuven Moskowitz is the founder and CEO of Litify which provides technology solutions for law firms by providing a trusted, intelligent, user-friendly platform for practice management. The company has raised over $50 million from top tier investors like Tiger Global or Fortress Investment Group. Prior to this, he cofounded OneReceipt (acquired by Performance Marketing Brands) and Penguin Digital (acquired by Shutterfly).

In this episode you will learn:

  • The future of legal tech
  • The key parts of innovation that law firms need most
  • How to balance optimism and realism as an entrepreneur
  • The importance of saying no
  • Mastering long sales cycles as a startup
  • How to contact Reuven


For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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The Ultimate Guide To Pitch Decks

Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Reuven Moskowitz:

Reuven Moskowitz passion is building and growing innovative businesses.

In addition to founding Litify, Reuven Moskowitz serves as COO of Morgan & Morgan, a law firm with 30 offices and over 300 attorneys.

At Morgan, Reuven Moskowitz saw the need for a new software solution built on Salesforce to provide insights and operating efficiency to the firm.

Litify was born out of John Morgan’s and Reuven Moskowitz vision to revolutionize the business of law. Reuven Moskowitz was previously Senior Director of Mobile for Shutterfly after selling his startup (Penguin Digital) to the company.

Reuven Moskowitz is a Harlan Fiske Stone graduate of Columbia Law School.


Connect with Reuven Moskowitz:

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Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today we have a very interesting founder. A founder that has been scaling companies for quite a bit has done it multiple times, and I think that we’re going to be learning a lot about law firms, too. Legal Tech hasn’t really experienced a lot of disruption in the past years, but I think we’re going to learn a lot about this today. So without further ado, I’d like to welcome our guest today. Reuven Moskowitz, welcome to the show.

Reuven Moskowitz: Thank you for having me, Alejandro. Excited to be here today.

Alejandro: So originally born in South Carolina, and then moved to Brooklyn, Tell us about a little bit about those years.

Reuven Moskowitz: So the South Carolina years, I don’t have that much recollection about. Sometimes, when I go through security, and they look at your passport, “Why, you’re not really from there, are you?” Those first years, my family. My parents both were immigrants. They came to America when they were pretty young and found their way. My dad was doing a residency in Jacksonville. He ended up selling in South Carolina. When I was a little kid, we moved to Brooklyn. That’s where we had a lot of family. Yeah, basically, all I remember is Brooklyn. We heard a lot of the stories from the south growing up but pretty much raised and grew up in Brooklyn.

Alejandro: Very interesting story, as well, from your parents — both immigrants. I understand that they met here in the U.S. Your father also went through a lot with the Holocaust and all of that. Could you tell us, as well, what you learned? Because having parents that came here and did it for themselves, I’m sure that really made a lot of who you are today and the way you see things.

Reuven Moskowitz: It’s true. It’s hard to think about that kind of scenario, where you have to start with nothing. I think about that a lot, and I’ve, obviously, been so fortunate to have a lot of a head start where people like my dad, who came here. He came over when he was two years old. He used to talk about the boat, the Queen Mary.

His family was very much affected by the Holocaust. My grandma grew up in Auschwitz. So, that was the environment we were brought up in. We used to go to my grandma all the time. She would talk about her parents were killed; her siblings were killed, uncles, aunts. This is that survivor mentality, but actually being able to do it. I always think about my dad being able to pull himself and go to college. Being the oldest in the family, he was the first one in his entire family going to college, going to medical school, and building a family. My mom’s similar kind of background, too. She was from Algeria, a small place in North Africa. They had to leave there due to persecution. It just wasn’t a place where they were welcome. They ended up in France. She also went to medical school, came to America, met my dad, and settled down in South Carolina. It’s been this idea of persevering and self-starting and being able to make something with nothing. That has always been an inspiration, and it has always set the foundation of how anything is possible. That’s the mentality of if you want to get something done, just do it.

Alejandro: That’s amazing. That’s amazing, and I’m sure that if this was like the building blocks for you to go later and become an entrepreneur. Why don’t we talk about this because very early on, you started with some projects? The first one here was OneReceipt. Why don’t you tell us about this one?

Reuven Moskowitz: Sure. OneReceipt was a simple idea, and sometimes, that’s all you need and differentiated between the people that do things. It’s not always, “Oh, wow! That was so genius.” How many times do we say, “Hey, I thought of that idea, too”? So it was one of those kinds of stories, and maybe that helped build the confidence, later on, to say, “By the way, it doesn’t have to be that complex.” It really has to do with whether or not you could start it and get it going. A buddy of mine, someone I’m still very close with, I had this idea for a receipt-aggregated product where you’d be able to get a better sense for what you were spending on as opposed to getting, say, a 500-hour statement from Amex. What’s behind that? How much were you spending on coffee or home supplies? It was in the early days of getting those financial reports. We had this plugin that we created for email. We had the sink, and it would give you some pretty rich analytics in terms of what you were spending. We found some other founders who had the similar idea — brought these two guys together also, and we started this company called OneReceipt. Soon after, we sold the business to a company called eBates, which does a lot of the online promo codes. Those two guys stayed on board. Interestingly enough, one of those guys I’m still close with, and he’s with us today at Litify. It was the first taste of getting involved in technology and the pace of what you could accomplish in technology. So the idea of being able to execute and be accomplished. That was the first project that I started with.

Alejandro: How old were you?

Reuven Moskowitz: I was probably 22 at the time.

Alejandro: Wow! That’s really impressive. After this experience, you were still in college, and you were seeing what the future was looking like, then you started to get some exposure to law firms. Tell us about this.

Reuven Moskowitz: Yeah. A close friend in the family was a lawyer, and said, “I need some help at my firm to build it out. I have some ideas of how we could scale the business from a customer acquisition standpoint and from an operation standpoint. I could use someone to come on and help execute some of this. You said something so interesting in the opening, which is you don’t really hear a lot about legal technology, and I think we’ll talk a bit more about why that is. Why is it that legal has been slow to adopt? Everybody talks about it, but what does that really mean that they’ve been slow to adopt? They’re all using cars, emails, and phones, so why is it? I was brought on board at this firm here on Long Island. What I noticed quickly was that there was a complete fragmentation, not just within the industry where there are so many different types of lawyers doing so many different types of law with sort of no consolidation. But also, on the platform side and technology side, they didn’t have an integrated solution. That was prohibiting and holding this law firm business back from being able to grow. Marketing campaigns, you had not insights. If you wanted to launch operating processes to communicate with clients, that was another system. It was very hard to do anything. At the time, I got introduced to Salesforce. The funny thing is, I didn’t even know what they did. If you would go to their website, it would say, “Generate more leads.” It almost looked like a lead-gen company. “This is interesting. I wonder what this is?” I got on the phone with someone and started reading about the platform, and “This is unbelievable.” The power, this extensible platform, could really do a lot. If I could just get this law firm on this platform, we could scale the firm. That hypothesis proved out to be true. We hired some consultants, built out some initial tools, and it was incredible to see how the firm was able to do something and started to grow quickly and become almost a market leader in the practice areas that it was. So that generated this idea where if you use somewhat available technology out there and approach it in an open way, you could do some special things in legal. That was the first time I got a taste where enterprise, technology, plus legal could have a major impact in scaling law firms.

Alejandro: This was a really nice segue into what will become your next business. Tell us about this.

Reuven Moskowitz: At the time, I had this idea of doing something — I had an uncle, actually, who is in the photo business. He was making plaques and awards. So I had some exposure to photos and photo businesses. It was right around when the iPhone had a camera coming out, and I said, “It’s interesting. This is where people are going to want to print, create, and interact with their photos. So I started a business called Penguin that essentially would be the photo business for mobile-only business. Part of it was called MoPho. So the app on iTunes and Android was MoPho for mobile photos. I started out that business with a couple of friends and built that out quickly to the market leader in mobile photo processing. A couple of months into that, we sold that business to Shutterfly with the idea to help accelerate their mobile roadmap and transform that business from a web-first company to a mobile-first company. We sold the business to them in 2014 and joined them as the Director of Mobile. That project was an incredible experience.

Alejandro: Just out of curiosity, how did you capitalize this business?

Reuven Moskowitz: We raised some family and friends; we had some small institutional investors, as well. We didn’t raise that much. We were pretty much a small shop. We had about 15 people at the time.

Alejandro: Very nice. Why did you guys decide to sell the business? Was it an inbound type of lead that you guys got from Shutterfly? Was it like a proper M&A process that you ran, or how did the transaction come about?

Reuven Moskowitz: We decided to sell it. It was a great opportunity both from an exit perspective, but also to work with what we believed could be something special, to do something really meaningful and to transform not just this one business, but the industry. And today, the Shutterfly app is still out there, and it’s still generating a ton of revenue, hundreds of millions of dollars of revenue under mobile business. It was an exciting opportunity to learn, to have an exit, and to do something special. In terms of how that deal came about, we were starting to have licensing conversations with HP, Snapfish, and Walgreens intimately. We had a friend; actually, one of our investors knew somebody who knew the CEO of Shutterfly, Jeffrey Housenbold. He mentioned something about what we were up to, and Jeff said, “This is the place for Reuven, so do it.” I connected with Jeff, and since then from our first conversation was just completely bought into his vision and how what we were doing together could be something special. 

Alejandro: Very cool. Obviously, the terms were not disclosed, but I understand that it was a 5x return for investors. Not bad at all. So Shutterfly, obviously, a rocket ship. Right now, it has over 7,000 employees. But I think that you joined at a time where the company was also experiencing a very good amount of growth. What were some of the learnings that you got from this experience?

Reuven Moskowitz: I would say it’s one of the most — maybe sometimes, founders don’t necessarily see that. I certainly didn’t early on. I thought it would be great. “You made some money. We’re going to be at Shutterfly, and it will be fun.” But actually, the learning of having incredible leaders around you and people like Jeff had a boss [0:12:13], Erik Weitzman. These were really experienced people who were able to teach me more than anything that I was able to make, whether it was around product strategy or patience or building specific proofs around data to prove out your theses — and not only trusting your gut and certain things like that. That was even more valuable than just selling the business.

Alejandro: Got it. Jumping here to the next question, you then decide to leave Shutterfly. You were heading up their mobile initiative, but you made the decision to go into Columbia to study and become a lawyer. Tell us about this.

Reuven Moskowitz: Part of the deal when I joined Shutterfly was that I’d be able to start and continue my education at Columbia. I always knew after that first experience at the law firm that I wanted to do something in legal and something to do with legal tech or legal operations. I thought that would be a great time to do that. I took [0:13:39] into Columbia and sold the company to Shutterfly. I figured, “I’m going to get my degree at Columbia.” I was there for basically the same period of time that I was after I sold the business to Shutterfly, which I had a three-year commitment to Shutterfly, and at the same time had a three-year commitment at Columbia, which was a great experience. 

Alejandro: Then, after Columbia, you started to think, “How could I implement technology to legal? This time around, you meet someone that changes everything, the course for you. So what happened next?

Reuven Moskowitz: Like John Morgan likes to say, “Life is luck, and sometimes, you create your own luck. But even as much as you want to do that, sometimes it really just is.” I found myself invited to events for lawyers. It was actually out in Puerto Rico. I didn’t even know why I would go there, and the people that would be there. The last night that I’m there, I meet this person whose name was John Morgan, who I had read about and had read his book and heard a lot about. We started a conversation around law and legal technology and legal operations. Actually, the first thing I told John was, “I read your book, which I loved.” We started talking a bit about what he had going on. He starts articulating this vision that he had for his firm, which was the Google Law Firm. How could he take, what at the time was the largest plaintiff firm in America and the world, and scale that even further by creating a differentiated brand? But by putting systems in place, to take what became his brand and build on top of that into a large law firm. We started talking about that and the opportunity to do that both for his firm and even more broadly, I said, “This is sort of the idea that I’ve been thinking about, building a differentiated brand, but also building out a platform to take to other law firms to help them build their business.” We agreed that this would be a great partnership together. I joined together with John a little over four years ago. Essentially what we decided to do was incubate this idea at his firm where we would take the firm, move them onto a structured platform like Salesforce, and we built out the technology and the stack to do that. To fast-forward to today, the firm has about 3,000 employees, almost tripled in size. It really has established itself as a leader within that category, and it’s almost all because of these systems and the infrastructure that we’ve put in place. About three years ago, about a year and a half after that, we took those core concepts and spread it out to start Litify, which is this legal technology operating system [0:16:48] for law firms.

Alejandro: We’ll talk about Litify in just one second, but I want to understand here because perhaps there is some lawyer, some former and recovering lawyers like myself.

Reuven Moskowitz: Like me. Please.

Alejandro: Yeah, there you go. They’re wondering like, “Hey, but what’s going on in the law firms today?” They have a dinosaur structure. What don’t you just tell us? What were some of the systems, and what were some of the themes that you saw that were perhaps completely off?

Reuven Moskowitz: Yeah, it’s so interesting and something I love talking about more than talking about that other stuff about myself. That’s not where I’m comfortable, but what I get excited about talking about is exactly your question. What do you see in law firms, and what do you see in terms of legal industry, and what do I see in terms of legal technology? You would notice because of as a recovering lawyer. What you see is that number one: even if you take the largest law firm in the world, they still don’t represent 1% of legal, which is such an interesting phenomenon. You have fragmentation just in the legal service delivery side of it, which is something so interesting. Why is it that legal, which is a product they service that really is ubiquitous, but you don’t see a lot of consolidation? I think the reason is, is two-fold. One is, it’s unique service in terms of the different clients needing the different service, so clients themselves want to have something very specialized. I think what the phenomenon is, is that if you look at legal and legal service providers, lawyers, law firms, even if you take the largest firm that’s out there, you don’t see anybody with an outsized market share. It’s completely fragmented. I think there are two reasons for that. One is that every legal matter, every issue that you want to hire a law firm for, whether it’s to create some new rules, or create contracts, or help you understand something, or help you enforce something, or help you change the rule, or whatever it is, every client and every matter is unique. But even more so, every lawyer — it’s partially an ego thing, but it’s partially that is what they’re bringing unique to the table. So there is such a nuance that goes into each lawyer and law firm that it makes sense for them to be different. It’s not like just water bottles. Each one has something they’re bringing unique to the table, and each one has something unique that their client needs to have addressed. So you have that phenomenon going on. If that hypothesis is right, you’re going to have fragmentation within law firms. You’re going to have a lot of different lawyers offering different things and offering it differently. Forget about the pricing, but even how you communicate, or what your strategy is, or how you deal with your clients. That you have on one side of it. We think about the technology to actually support that. That’s why you see a lot of fragmentation around legal technology, too, because lawyers want the technology to support what their vision for their business is. What you see on the technology side is hundreds of different fragmented use cases, almost what we call now point solutions to deal with specific needs that a lawyer wants. So one lawyer wants to do discovery this way. You’ll need a discovery tool for that. They want their practice management done this way. You may have a tool to do that. What we’ve created now is both an ecosystem of so many different types of lawyers, and also an ecosystem with so many different types of technology, which is never really able to mature or evolve in a sustainable long-term platform. That’s what you’re seeing historically in this space.

Alejandro: Very, very interesting. So let’s go back now to Litify. Obviously, Litify got incubated within this law firm, and then you finally go your own way. Tell us about this.

Reuven Moskowitz: When we started the business about three and a half years ago, we always knew it would be something special. If we could get it to work, if we could prove out the platform as being strong enough and solid enough to get that one firm on, it would be something that we could change a broader industry by. So we take that thesis and brought it to market and say, “Are there other firms who would want this type of technology — would want this kind of approach to helping them run their firm?” Right out of the gate, we got a couple of early adopters saying, “This is not only something I’ll be interested in trying, but this is actually what I’ve been waiting for. We’ve been looking for something to break the chains of these other products that have never been able to evolve or never been able to integrate, and certainly don’t set them up for long-term success and long-term scale.” The first year we go out to market, find a couple of firms who are bold enough and maybe even wanting to say, “We’ll put our ego aside.” Maybe they’ve built their own systems, some homegrown applications, and things like that. They bought into that vision, and we got them on the platform. They start seeing objective demonstrable improvements and operations to their brand, to their scale, to customer satisfaction, and things like that. So our first year of selling, we sold about 3 million dollars’ worth of licenses to firms. Last year, we were able to double again; this year, we’ll probably grow about another 120%. So the thesis around the platform, which I’d love to get into and why we think it’s differentiated and why we think firms are excited about it and started proving at itself right out of the gates. 

Alejandro: What ended up being the business model? How do you guys make money here?

Reuven Moskowitz: We’re a SaaS business model. We’re built on top of Salesforce, so we leverage a lot of the value that comes out of the platform from a security, from an architecture standpoint. We build our own products on top of them, so we sell per license per user per month.

Alejandro: Got it. Who was the founding team of Litify?

Reuven Moskowitz: Founding team was John Morgan, who is from the firm, myself, Terry Dohrmann is our CRO now. He runs revenue and comes from Salesforce. Steve Mandel runs our product. Our CTO is the same CTO that we had at Penguin, Jeff Argast. We were at Penguin when we sold Shutterfly after I left comes Litify. He went to Adobe, and about six months ago, he came back to be our CTO.

Alejandro: Very cool. Let’s talk about the early days of the business. Obviously, the selling to law firms probably is a beast because it’s a long-sell cycle. How did you guys go about that?

Reuven Moskowitz: Selling co-op firms is hard. I think what makes our approach a bit more unique is that we sell to managing partner firms. Maybe take a step back. The hard thing about legal is that it’s super fragmented, but in the same respect, there are these pockets of lawyers who are very much looking to see what the industry is doing. If you get into a group of lawyers who trust each other, respect each other, and are going to look to each other for advice, you can actually build some nice momentum within these pockets. Obviously, with John Morgan, initially, we were able to get a couple of firms on board and break out into some other groups, prove success to their firms, and you can build nice momentum on top of that. That’s the first piece. The second one is, we’re coming at this from both inefficiency and an operational level. So, obviously, you have to buy-in from the technology team, from the marketing team, from an operational team, and the lawyers using the product, of course. The other thing that we’re able to do is sell directly to the managing partners of these firms. Our approach is 1) automation and 2) transparency. Those were the two key drivers early on. If you’re able to have that conversation, both with the end-user saying, “We’re going to make your life better,” but also to managing partners or executive committee of these firms, “We’re able to make your business better.” Being able to do both of those puts us in a unique position. 

Alejandro: Absolutely, and for this, you guys have raised quite a bit of money. How much have you raised to date?

Reuven Moskowitz: We raised around 55 million between our seed rounds and the Series A.

Alejandro: And what a Series A. Tell us about his Series A.

Reuven Moskowitz: Sure. We raised 50 million dollars from Tiger Global, which has been an incredible partner for us and the whole company. I met with Scott Shleifer a few months ago who saw immediately what we were building and the momentum behind us, but also someone who appreciated the opportunity. One of the reasons why we raised that is to start capitalizing on that opportunity both organically, continue down within the vertical that we were currently servicing, and broadening that out to service other types of law firms specifically. And maybe look at some other types of things within legal like inhouse counsel or government or things like that. There’s tremendous opportunity there. And also accelerate our product roadmap with specific feature functionality that we saw a big market appetite for, and also to invest extensively in customer success and getting our customers live. So together with Tiger, we both aligned on what the vision and the opportunity is, and we wanted to get there quicker. So having Tiger believe in that and bet on this was an incredible thing for us.

Alejandro: That’s amazing because, typically, for a business of this nature, what are the most typical challenges?

Reuven Moskowitz: I think with any business, it’s interesting. So product/market fit, obviously, is what you read about, and I’ve always thought about, and it’s the thing that I’ve always had the most anxiety about, which is, you’re going to build something. Is it going to work? Are people going to want it? Are people going to pay for it? That makes, obviously, a lot of sense. Then the second question is, how big is that opportunity, or are you going to serve to get all the buyers and you’ll be done. I remember always reading about these concepts. Where you have product/market fit, there will still be other challenges like customer success or scale and things like that. I remember even almost rolling my eyes at that saying, “That’s not a real challenge. Product/market fit: that’s a real challenge. Are you going to build something that people want to buy? But once you have that, it’s easy. It turns out it’s not true. There are still challenges and specifically, scale, and scale comes with a ton of challenges. It’s not just doing things at a bigger level or at a broader impact. It’s doing things differently from management to execution to how you think about your clients and about focus and priorities all changes. That’s what we’ve been going through. Last year, this time, we had about 40 employees. Now we have about 140 employees. Then with that culture, these are things that maybe I’ll admit that maybe I didn’t pay attention to. You don’t think that those are the things that matter. As you mature, those are the things that matter the most. So that’s been the evolution of how we think about going to business and focusing on the business.

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Alejandro: Also, you were just touching on this — 200% growth in the last 12 months on the employee count. How do you go about culture?

Reuven Moskowitz: The answer is: be deliberate about it. Early on, I don’t think companies that have 15 employees or 50 employees really need to think about it. Either you have it, or you don’t, meaning either your good to your employees, you bring good energy to the workplace, you treat your people well, and you’re generous with them, and you honestly look to have a good time every day. I used to think about how lucky we are, when we were a smaller group, that everybody here is going to laugh out loud at least once a day. Then as you get bigger, you have to be a lot more deliberate about that, not just because there are more people and it’s hard to touch everybody, but also, then you start thinking about remote workforce, or people that are put into different offices. We have an office now in New Orleans. It becomes a lot harder. And the second part that becomes hard about that is, you sometimes have great team players, but maybe they’re not great managers. Then that becomes the dynamic where you want to give people the opportunity to develop their career and maybe get promoted, but they’re really not great managers. How do you bridge that gap? Sometimes, you have to make hard decisions in doing that. That also affects culture. I think the answer really is, you have to be deliberate about it, and it doesn’t come naturally. Especially, maybe to some founders, but certainly, when you think about the evolution of the company, where you don’t need to be deliberate about it early on. Either you have it or you don’t. But even when you have it, you have to start being deliberate about that.

Alejandro: Talking about evolution here, Reuven, the journey’s not a straight line, as we founders know. Looking back, what would you say has been the hardest moment for you, and that moment that came with the most amount of learnings?

Reuven Moskowitz: It’s not a straight line, and sometimes, not even close. There’s one graphic I love. You could probably Google it, where people think it’s the beginning. You have the bike with the line all the way up. What it really is, there are pits, and there are ups and downs, and there are really big downs. Sometimes, when you’re down, you don’t even realize that’s the beginning of going down. You’re about to accelerate down, and you accelerate all the way up. I think a couple of things. Before I answer your question about some of those tough moments, for me, one thing I always say, at least once a day, “If it’s easy, everybody would do it.” I said it this morning because somebody on the sales team said, “If it was easy, everybody would do it.” I really believe that. It goes back to our earlier conversation from my dad and the upbringing. If you look around and see what differentiates the people who do it and the people who don’t do it, one thing is that they did it. Those obstacles will come, and again, if it was easy, everybody would do it. Specifically, to your question about some of the hard things. The hard things have been around people where you’re faced with the situation where you want to believe this person is good because 1) getting rid of somebody is hard to do. It’s the hardest thing you probably have to do. 2) You have to then focus on replacing them and recruiting, which is another really hard thing to do. Then you have to also focus on the rest of the business that’s dependent on that group. Then being honest with yourself that, “If this is something that you’re going to have to do, do it sooner rather than later.” That’s happened at least twice here at Litify. Probably both times, I should have made those decisions a bit faster, either putting somebody in a different role and again, dealing with the inevitable. Those are hard things that you hope you get better at and predicting them but also, dealing with them and addressing them.

Alejandro: Yeah, that actually reminded me. With one of the companies, when I was starting out, there was an employee that I just loved. But the employee was not delivering, so I tried to put that employee on other roles, and I just saw the employee again failing and failing. That, at the end of the day, just creates a bad environment for the culture of the business rather than getting the employee the benefit of going and getting another job where he or she is going to succeed, I just continued to delay that process. Have you also experienced that, or have you seen that, as well?

Reuven Moskowitz: You hit it right-on. That’s such a hard thing. It’s such a hard thing, and especially when you’re trying to grow a business, and you have to make quick decisions, and maybe you’re even built that you don’t have that patience, necessarily. Sometimes, it makes you feel bad. Sometimes, I feel bad. It’s like if I had more patience, or I had more time, I would coach the person. Sometimes, at a startup, especially, you don’t have that luxury. You don’t have that environment to be able to do that. So, it’s hard. You try to justify it by saying, “Well, if the person is not going to be successful here, they’re not going to be successful. So, I may as well let it happen sooner.” Those, definitely, are the hardest parts, especially of a startup. It may be even a bit easier in the situation that you talked about where it’s an employee who’s failing. I think it’s just as challenging and probably even harder where an employee is doing well, but that group or department needs to scale, and now it needs to operate entirely differently. So it’s almost like the analogy where you go and build a basketball team, so you hire a crew to build out the stadium. You’ve got all the pieces there, the lay of the wood. Everything is getting done. On the last day, there’s a painter there just putting on the finishing touches, and you’re thinking about starting five. You need people to play on the team. You can’t just point to the painter and say, “Hey, you helped build this all the way through this point, you’re going to be point guard.” Of course not. It’s just a different skill as the business evolves. So even someone who’s done a really good job, as their department needs to collaborate differently, as the role of the department, or maybe it’s a failed investment. It was a moonshot kind of project. Being disciplined to say, “Okay, this person is not going to be able to be a manager.” Now, what do you do? That’s really the hard part of scaling.

Alejandro: For sure. I would love to get your thoughts on this. How do you see the legal tech evolving?

Reuven Moskowitz: I think it comes down to two things. I think companies that are going to be successful or have to be able to do these two things. 1) Integrations and 2) be extensible. What that means is, we believe that integration is the prerequisite for having any automation and having any transparency. So the more these tools are being generated, or the more these tools that lawyers are relying on — again because they’re all unique. They all have served their fragmented approach in their own subtle way to deliver their service to their unique clients. You have to have one place for an operating system to pull it all together. So now, the firm can have some automation, which means, when you think about automation, it doesn’t necessarily mean AI, but it does mean efficiency, which the clients can benefit from. I think, more importantly, automation means predictability. You can create the system and process. And you need integration to be able to do that. So predictability, automation, and too, transparency. The more disparate systems you have, the harder it is to have that transparency. What’s really going on at your firm? What’s really going on with your client? What’s really going on with the service you’re delivering? That’s number one. So, integration. And number two is extensibility. Firms need both the ability to embrace what makes them unique on whatever platform they’re on and drive that uniqueness through the platform. But also, they don’t want to be locked into an approach or a practice area or a specific paradigm forever. A lot of the systems that have been traditionally created, whether they’re on legacy platforms, or these point solutions, they’ve been super rigid. They said, “Okay. Lawyer, you want this? Do you want to be able to x, y, z? Here you go. Done.” That’s limiting when you think about even the needs you have today. Let’s say that evolves tomorrow. Let’s say a client comes in with something a bit different, a bit more nuanced. When I want to move into a practice area, that’s going to be significantly different, or I want to be able to scale my team. Without that extensibility, you really don’t have a product. You’re really not a technology company. It’s sort of a theme that I think about, even out of legal, which is, what differentiates any business from being a technology first or a technology-driven business from a company that’s not? It’s not if they’re using technology. It really isn’t because, again, you could have a law firm or any business where the person is using email. They’re on Slack. They’re on Twitter. They have a social — they’re doing all those things. They’re driving to work in a Tesla. That’s technology. The biggest differentiator is whether or not when a business wants to make changes to grow, to improve, the first place they turn to is their platform. If the first place you’re turning to is the tools that your employees, your staff, your team is using to implement those changes, to make sure that they’re being adopted, then you can say you’re a technology company or a technology driven business. That’s what, I think, is going to differentiate technology, legal tech companies that are going to scale and thrive. The ones that are going to be — these are just features, we don’t need that. They’re not going to be able to help our business move forward.

Alejandro: Very interesting. One of the things I typically ask the guests that we have on the show is — here you are, and you’ve done this multiple times. Now, this is one of your biggest challenges and most exciting journeys with Litify. Knowing what you know now, Reuven, if you had the opportunity to go back in time before you were to launch that first business, what would be that one piece of advice that you would give to yourself before launching the business and why?

Reuven Moskowitz: The first business?

Alejandro: Before launching a business. Let’s say before you’re even coming out of college, and launching a business is not even in the picture. It may be later, but knowing what you know now, rewinding and going back in time and being able to have a conversation with that younger Reuven and saying, “This is the absolute one piece of advice that I’m going to give you before you head on to launching a business.”

Reuven Moskowitz: I think if I had to pick one thing, it would be saying no. The power and importance of saying no. It’s maybe hard to articulate, but being a founder, you have to be completely or maybe a little bit crazy, because you have to be an unlimited optimist — completely, unlimited optimism. You have to have an unlimited amount of optimism. You have to be super hopeful. You have to believe. You have to dream and think that anything is possible. That’s, obviously, number one. You have to believe anything is possible and that you can do it. But at the same time, you also have to be disciplined and focused enough to say, “Even if it is possible, and even if it is a great opportunity, maybe that’s not the biggest opportunity, and maybe that’s not the biggest area of focus. Being able to say no while also being completely optimistic and completely, faithfully believing that anything is possible, that’s a hard balance. I still don’t think that I’m there perfectly, and maybe you never could be because I’d rather over bet on being optimistic, but being able to do that — I think your read some of these founders and definitely some of the great ones, they talk about ruthlessly prioritizing and focus. Looking back, there were certain opportunities that I saw, and they may have been great opportunities, but if I would have said no to them, I would have been able to double down on some opportunities that I felt and know were bigger opportunities. So being able to say no while being also feverously optimistic is the one thing I would go back and tell myself.

Alejandro: Got it. Well, man, I’m glad you said yes to this interview. Reuven, for the folks that are listening, what is the best way for them to reach out and say hi?

Reuven Moskowitz: [email protected] is the best way. Love speaking, love listening to other people and their perspective, so really appreciate this opportunity. Shoot any questions, any thoughts, any feedback, especially if you think I’m wrong about something, that would help me the most. Again, I appreciate you having me.

Alejandro: Amazing. Well, Reuven, thank you so much for being on the DealMakers show today.

Reuven Moskowitz: Thank you, Alejandro.


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