After practicing law for 17 years at top-tier firms, most recently as a Partner at Orrick, Herrington & Sutcliffe, Catherine Krow founded Digitory Legal, a cloud-based legal budgeting solution for lawyers and clients.
What we chat about in this episode:
At some point, as you move forward in your career, somebody's going to ask you how much it is going to cost, and you can't say it depends. You have to actually get the work, in order to get the work, you're going to have to be able to give a better answer than that.
Podcast Transcript:
Nicole Abboud
I am Nicole Abboud and this is The Gen Y Lawyer podcast.
What originally started as an experiment to find young lawyers shaking things up in the profession led to much bigger conversations about law, life, and the big picture. Join me for a peek into the lives of courageous lawyers who are taking a chance on themselves.
Welcome Gen Y’ers! I hope you're doing well and getting through the month of February just fine. Speaking of February, I actually have my annual listener survey going on right now, and I would love to invite you to participate. If you're a listener of this podcast and feel like you would love to contribute your thoughts and suggestions, then I of course want to hear them. I mean, you're already taking the time to listen to this episode, so why not just take a few more moments and share your opinions about how we can make this podcast an even better listening experience for you? I would really appreciate your input. You can find the survey at www.bit.ly/2017gwlsurvey. It's only going to be available for another week or so, so if you're listening to this after February 2017, then the link won't be available, but of course, you can always share your thoughts and opinions through e-mail at [email protected].
My guest today is Catherine Krow. When I wrapped up this interview with Catherine, I was reminded of why I just love having attorneys on this show who have been practicing for a while. As in non-millennial attorneys, because there really is so much wisdom and insight that we young lawyers can gain from listening to more experienced attorneys. Catherine is an amazing woman, lawyer, legal tech company founder, and just an altogether inspiring person. After practicing law for 17 years at top-tier firms, most recently as a partner at Orrick, Herrington & Sutcliffe, she founded a tech company called Digitory Legal, which is a cloud-based legal budgeting solution for lawyers and clients.
In this episode, Catherine explains how she made that decision to transition from being a partner at a big law firm, leaving behind many of the perks that come along with being a partner, but also many of the restraints that come along with it too, to follow her heart and start a business in a new industry. Catherine walks us through the exact steps she took, starting right from that courageous moment when she resigned as a partner. To explaining the nitty gritty decision she had to make when hiring people to help her develop the software for her business and bring her vision to fruition. You'll notice that Catherine is fairly soft-spoken, which is not something I noticed actually right away until she pointed it out, but we talked about this and talked about how for that reason, Catherine was greatly underestimated throughout her legal career and again in her new position as a tech startup founder and how she turned that underestimation by others into fuel to defy expectations.
What I love the most about Catherine is that she was courageous enough to completely change the course of her life and career after 17 years of practicing law, I mean, that's not easy. This should give hope to anyone who's thinking of taking such a big step in a new direction after a prolonged period of time of practicing. This should serve as a reminder that it's never too late to make a change.
Without further ado, here's Catherine.
Catherine Krow
Yea, I was practicing law and trying cases, taking names for a long time, and somewhere around 2014 or 15, I realized that it was now or never if I was going to try something new. So, I resigned as a partner at Orrick and started Digitory Legal.
Nicole Abboud
That is not an easy thing to do. Did you always feel like you were going to do something new because you said it was now or never? I guess that implies that it was on your mind, huh?
Catherine Krow
Yes, it was for about the last year, it was not easy to do. It was a very, very big decision, particularly because from all outward perspectives I was really doing everything you should do and had become, I think what people would outwardly define as, absolutely successful in big law. But I had been doing it for a long time, and practicing law is like a pie-eating contest where the reward for good work is more pie. And I like pie. I love some pie.
Nicole Abboud
But it makes you fat. I like that analogy. I see where you're going with this.
Catherine Krow
Yea, exactly. So I did not want to do that for the next 20 years and I realized that as I got more and more up the ranks and as the cases that I was able to try got bigger and harder, I was going to have the golden handcuffs on and it would be very, very difficult for me to step away. So I made the decision to pursue what mattered to me and my own values and take a chance. And so I did, and I spent, you're right, I did spend about a year thinking about what was the right decision and what mattered most to me. So it was a very long and thoughtful process, so definitely not a rash decision.
Nicole Abboud
And what was it that you concluded? What is important to you?
Catherine Krow
So I'm not driven by things like prestige and security as much as a lot of people are, but challenging and defying expectations mean a lot to me and the ability to pursue what I think is right has always been a core value of mine. So, I wanted to do something that I felt passionate about and that I felt would advance the profession and it definitely, definitely wanted to surprise people, and that doesn't matter to me.
Nicole Abboud
And I imagine that's what you did when you started your company. So, you mentioned it's called Digitory Legal. Please tell me a little bit more about that business.
Catherine Krow
So Digitory Legal is a cloud-based legal budgeting solution for lawyers and for clients. On the client side, we give them unprecedented transparency and the ability to really understand what their legal costs are and why, and a way to compare apples to apples. And for lawyers, we give them a way to create accurate budgets quickly and then manage your team to budget, which is a very difficult thing to do, particularly when you're dealing with hours-based models.
Nicole Abboud
All right, so we heard a little bit about the lawyer side of you and now you tell us a little bit about the business. Can you make that connection for me? When you stopped to think about what you were truly passionate about, what you really want to do, and what really mattered, is this what you saw? Like, how did this come together?
Catherine Krow
Yeah, it's connecting passion and ethics and legal budgets. It's probably not the most natural correct connection, so that might give you some pause. There is a method to my madness. So I wanted to solve a real problem and when you're in the trenches, practicing law, and get asked for a budget, particularly litigation budget, which is where we're focused now and where I was always practicing. It's really hard to do and it's becoming more and more important to do it right as the legal industry evolves. And you can't say no, a budget is too hard because clients, it’s the buyer’s market, and clients expect it.
So, trying to do that right is very difficult and I saw lawyers struggle with that and I struggled with that. And then making sure that you were managing your team to those expectations once they've been set is not an easy thing to do. So I was trying to solve for me a problem that was very, very real, but most of the solutions that I've seen in the industry, or in legal tech. You pick one side or the other, it seems like a very zero-sum game and I don't believe it needs to be. I think that that connection between the lawyer and the client is very powerful and if you take one of the most contentious and difficult things to do, which is manage costs and communicate with your client about those costs. And if you build in more connection, more transparency, and more education, you can really elevate the industry. So I'm passionate about strengthening the lawyer/client relationship and building tools that advance that goal.
Nicole Abboud
And I love that this kind of software, this service is so needed right now. First, before I go any further, are there exotic birds behind you? Are you in the wilderness? Like what's happening? I was trying to focus on what you're saying, but all I hear are those birds and it's cracking me up.
Catherine Krow
Would that be one of those editing moments?
Nicole Abboud
No, I might have to keep this in that is just too good. No, I love it, I mean, hey, I'm a fan of nature, so anytime we can incorporate it into this podcast, it's a good day for sure. A few episodes back on this podcast, I actually had an entire episode about time. So, the billable hour, time management, and one of the themes that came out of that episode was that like you said, it is a buyer's market and clients are really pushing for, or they're really expecting their attorneys to give them an estimate of how much something's going to cost, like the billable hour is no longer going to fly for a lot of clients. So I love that you're situating yourself and this business, Digitory Legal, to be in a good place in the upcoming years because I think that's where it's going. Clients really want, I just don't think they want the billable hour, and they just want more of a solid estimate of how much something's going to cost.
Catherine Krow
They definitely are looking for accuracy in budgets. There have been a lot of articles coming out recently about the importance. For example, for legal OPS of accuracy and budgeting, it's one of the top metrics that they want law firms to follow, and frustration on the client side with communicating about costs. In the interviews that I've been doing, there's definitely a vibe that the day of the billable hour is coming to a close. Now, whether that means hours will not be billed and we'll go straight to AFAs, I'm not sure, but there are definitely modifications on the traditional models that are happening and very prevalent right now.
So, you see budgets are becoming not exceeded. You can no longer just say, “I think it will be about this”. Once you put that number out there, you have to live with it, and that is becoming extremely common. You're starting to see moves towards risk sharing and callers on budgets. There are all sorts of arrangements that diverge from the billable hours. So while hours may be billed and may be tracked, it's no longer, you're sort of working your way up towards your budget estimate, and you can't exceed it anymore. Does that make sense?
Nicole Abboud
It does, and you mentioned AFA, I believe that's an alternative fee arrangement. Is that what that is?
Catherine Krow
Yes
Nicole Abboud
OK, just clarifying that. So this is obviously good from a client's perspective. Do you think this is placing somewhat of a burden or a cap on lawyers?
Catherine Krow
Lawyers are struggling with this. They are absolutely struggling with this. It is making it more difficult to practice in the traditional ways, but it is giving a leg up to those lawyers who are willing to think outside the box.
Nicole Abboud
Hmm, ok. So in keeping with this discussion about budgets, how can a young lawyer, maybe a new lawyer who just went solo, someone who's a few years out, and just open their own firm. How can a young lawyer who hasn't maybe worked on an entire case from beginning to trial to the end, who might not know how much something's going to cost? How much time it's going to take and can't really give a good estimate or anticipate how long something, how long the matter will take. How can they start incorporating budgeting into their practices?
Catherine Krow
So the key at first is to start tracking your time. Don't block bill, but task bill, even if the client doesn't ask for them. And the reason to do that is so that you can find out how long things take. You can't go back to a block-block, billing situation and understand how long, how many hours you spent, preparing for the deposition. And just to elaborate what I mean by block billing. If you write down everything you did in the day and make it a one-time entry, that's considered block billing.
So everything is listed in one big block and you say 8.2 hours and everything you did is just in one entry. If you break it down to say, prepared for deposition, including your review and analysis transcripts of review and analyze hot documents, you make that one entry and then you make a separate entry for research. And so you may add up to that 8.2 hours, but you've got discrete tasks underneath. You can start tracking how long things take and going back to your data or pass bills so that you have some sense of how much time you spend on things.
And that's important to understand. It's important to understand as a young lawyer that you have to have a sense of how long things take in order to manage other people appropriately and in order to provide clients with estimates. And that starts with writing it down in a way that you can go back and look at.
Nicole Abboud
Yeah, I guess that makes sense before you can give any kind of estimate, you really should understand how long something takes. That means that young lawyers do need to, at some point or at the very least, in the beginning, they need to keep track of their hours in that way before they can start moving towards budgeting and giving estimates.
Catherine Krow
Yeah. At some point, as you move forward in your career, somebody's going to ask you how much it is going to cost, and you can't say it depends. You have to actually get the work, in order to get the work, you're going to have to be able to give a better answer than that. And my biggest advice to young lawyers or small firms is just to never lose sight of the business aspects of this practice, now more than ever.
Ironically, that was probably one of my weakest spots as a practicing lawyer because large firms, and back in my day were less focused on that, than they certainly are now in, in terms of training young lawyers and promoting efficiency. But that is definitely changing and if you're going to succeed in this new changing market, you have to remember the business aspects. Business aspects, meaning your clients need to know how much things are going to cost and predict their expenses and you need to help them with that.
Nicole Abboud
And I actually was taking a look at your website a little bit earlier and I noticed that you have the subscription prices listed right there, which I think is great. That's transparency, which is good. And it's actually, no this is a good thing because not a lot of businesses will just put their prices on their website, so that's good. But here's what I noticed, I noticed that it's actually very affordable. So it's not, because when you hear of a business like yours, a software like yours, you assume it's really just big law that's using it, but who is it that you're hoping uses Digitory Legal?
Catherine Krow
So Digitory Legal is really for everyone. The beauty of cloud-based solutions is that you can kind of build your own and use what you need. So what you see on the website right now is our single-user platform and that is really good for very small companies and solo practitioners. Who just needs to construct a budget and then share it with clients or with their small teams. And we've priced it so that we can give access to these tools to everyone who needs it. We are doing larger enterprise releases are coming out. Starting in March, we will have our RFP release and more bells and whistles and enterprise features and templates, which we are currently making accessible for a limited time for anybody who tries the system because we're loving the feedback. Those will be subscription based at some point as well.
But the goal here is to give access to what you need to everybody. And the problem with systems right now, is they really are designed, most of them are designed, for big law and large companies and require six-figure investments and that's part of what I wanted to change. I wanted systems that would work for everybody.
Nicole Abboud
So I heard you mentioned earlier that one of the reasons why you wanted to leave your position and start this business is because you wanted to challenge, but also you wanted to defy expectations, which brings me to this next question. It ties in beautifully. I actually want to hear about your experiences as a woman in tech, because you've now been, so you're a woman in law and a woman in tech and it's no secret that both of these areas, both of these industries, are underrepresented when it comes to women. Right?
Catherine Krow
Yea.
Nicole Abboud
So I want to hear about your experience since you are in both.
Catherine Krow
Well, I would say that, as you can probably tell, I'm a soft-spoken woman, and being underestimated has actually been part of my professional identity or career since I got into law. It was especially as I started trying cases against very, very experienced practitioners. I was underestimated at the outset all the time and I find that very motivating. It’s, and I defeated it by just being more focused, working harder, and being more prepared than everybody else, and suddenly the underestimation changed and people started listening a lot harder to what I'd have to say because I knew what I was talking about.
It is no different in tech. There is underestimation, it’s part of the reality. But I am focused. I am working hard and I intend to defy those expectations and that lights a fire in me.
Nicole Abboud
Yeah, I know. I was going to say, you are! I love that you're using that as fuel. Right? That is what keeps you going. Do you know what I love about that? I didn't hear you say that you tried to change how you are. And you, I mean, I didn't hear that you are soft-spoken. I can tell you, your voice is very pleasant, I will say that, but you're right, I guess you are softer spoken. And you didn't say you tried to change that to fit the mold of what you thought a lawyer should sound like. Instead, you just, what you said is they had to listen up.
Catherine Krow
Yep!
Nicole Abboud
I mean, they had to because you were so soft-spoken, right?
Catherine Krow
Now I did spend a little time trying to project a little more, especially in the courtroom, but yes, I tried very hard not to change who I am. There are a million different ways to try a case. There are a million different ways to run a company. And if you try to fit yourself into somebody else's mold or expectation, it is an excellent way to fail. You've got to be true to yourself and I do not fit a traditional tech startup founder mold and that's fine. I will do it my way and I will do it well.
Nicole Abboud
So I don't know if you had any business background when you decided to start the business, but walk me through the day you left your law firm to, I guess when you got the business up and running and started to get the word out. How did you, I mean it's software, so did you have a background in coding or anything like that? Or who did you have to reach out to to help?
Catherine Krow
So, I do not have a background in coding and I did have to reach out to. I did a lot of learning. It took me about six months to really roll up my sleeves and learn agile development and make sure that what I was doing made sense. I had 20 years of industry experience essentially, but I still wanted to do my homework and reach out to dozens of lawyers and in-house counsel, to make sure that the product idea that I had in my head made sense. So, step one was resigning.
Nicole Abboud
That is an important part, right?
Catherine Krow
That was not easy. And I remember very vividly the moment that I resigned. I told someone who had run on the big client, who I had worked with closely with, a lot of trials, and who was fairly high up in the management of my firm, that I was leaving and he said well in a few years we'll either be working for you or you'll be asking me for job. And so, I made the decision at that point, which side of that equation I wanted to be on.
So step one resigned. Step two decide on the idea. And that was a multi-month process of interviewing people and talking through what my problems were and what kinds of things would solve their problems and what would get them to change their ways. And so I did a lot of user interviews and I talked to coders about the feasibility of what I wanted to create. So, step 2 was research.
Step three was the nuts and bolts of starting a company. So I spoke to some startup founders just about the mechanics of getting started. How you incorporate what you need to do, and there are, fortunately, a lot of tools out there that make it easier for you to do this. Actually, one was Clerky, which was started by Orrick lawyers, and that makes it very easy for you to incorporate as a Delaware C Corp. And you get.
Nicole Abboud
Sorry to jump in, but what is it called again?
Catherine Krow
It's called Clerky, and they help you start your company. They curate the documents for you and walk you through some decisions and you can set yourself up as a company. So, the mechanics were being done, and I had formulated the idea now getting started as a non-technical person. And that was a challenge. You know the tech remains the biggest challenge. And if you talk to a lot of founders, even technical or non-technical, the technical aspects of it are always a big challenge, especially as you try to scale and bring in people.
So, I fortunately, I've been in this town, this town being San Francisco, for a long time and have a lot of friends who are willing to refer me to people who I started with just one individual contractor helping create the framework and whiteboard out what we needed to do. And he trained me on agile development, and so I spent some time doing that. And then it became clear that I needed more power, by power I mean bodies, in order to to create what I had envisioned. So, I was connected to a group of coders offshore through a former partner of mine. So all of this was very organic. Every connection I made was through people that I knew. It was a curated group that I worked with, and they helped me get the single-user platform that you see on the website now up and running. And through having done that and proved that I could take my vision and find the resources to create it, I was able to find coding resources in San Francisco, which as I'm sure you've heard are in very high demand.
So, the process is long, it's not easy. It has taken a lot of friend connections and careful steps forward and is definitely not for the faint of heart. But I have been fortunate to step by step continue moving forward and break through that enormous challenge of not being one who can code it myself. However, I am very, very involved in the day-to-day operations. I work with my coders constantly. I am in, I don't know if you are familiar with JIRA, but the store…
Nicole Abboud
No, I am not.
Catherine Krow
So, there are a lot of applications that I am now conversant in, that I've never heard of years ago, and Trello and JIRA and Digital Ocean and.
Nicole Abboud
OK. Yes, there are many.
Catherine Krow
And I'm on Slack, of course, and I'm on all of these daily working with coders, whiteboarding, and so on. So, while I don't code, I know I spent a lot of time learning an awful lot about the process and getting to the point where I could work with people who are really, really talented and take what's in my head and turn it into functional reality.
Nicole Abboud
Yeah, I think that's smart. Not, I mean if not necessarily spending the time to actually learn how to code, but knowing enough where you're overseeing, right? Managing others who are coding and putting it together and just making sure, it's exactly what you want.
Catherine Krow
It's definitely been a learning process, but I have to say that my team is awesome and I'm very fortunate to have some really great, great coders on board now.
Nicole Abboud
That's definitely good to hear, and it's always good when you've made good connections throughout your life and your career. That you can turn to when you're starting a new business because it does take a lot of help from other people as well. I was wondering if you have any, so you're like you said, you're in Palo Alto, and you are definitely in a good location for a tech startup or for a tech company. Do you have any suggestions for maybe a listener who, and I don't know if I have any listeners out in like rural Indiana, but someone who's not near a tech hub where they can, I mean is there or do they have access to resources online? Or do you have any suggestions?
Catherine Krow
So the first thing I did was listen to the Y Combinator Startup course and that is online. It's offered through Platzi, P L A T Z I, I think is how you spell it. Platzi.com and Y Combinator are the most well-known of tech accelerators, and they do of course online. It's moderated or hosted by Sam Altman, who is one of the founding partners of Y Combinator, and it gives some really good nuts and bolts advice on how to get started.
So anyone I would say who is considering making this leap I would highly recommend listening to it. You can listen to it anywhere and I still go back, as I'm doing different things and working through different elements of the business so that it's marketing or whatever it is. I go back to that part of the Y Combinator Tutorial and I listen to it again. So the Clerky, there are a lot of resources online available to help you get started. Clerky was one of them that I mentioned before.
But in terms of finding good people and tech resources. I made mine through connections and I would never forget who you know and referrals because they're always the best source. So if you're looking for people and looking to build, start with who you know and who they know, because that's probably going to work out a lot better for you than anything else.
Nicole Abboud
Yes, definitely good advice, and I'm actually going to list those resources in the show notes at genylawyer.com. So listeners, if you didn't get a chance to write it down, don't worry. Just head on over to the show notes, they'll be right there.
Well, Catherine, before I let you go, I would love to hear any advice that you might have for young lawyers who are interested in tech, and maybe interested in starting their own company. But they are currently practicing.
Catherine Krow
So advice for doing both is tough. I would say that you need to keep looking at reports that are coming out on the evolution of the industry because there's a lot of great information and it's very consistent coming out right now. And if you are looking to create a tech company in the legal space, you have to have a very good understanding of where the industry is going.
A few resources, for example, Altman Weil does a survey about the legal industry every year. Georgetown did a 2017 report that has been largely republished because it has a lot of comments on where we're going with the billable hour. Stay on top of where the industry is going so that you make sure you're serving the needs of the future.
Tech is also in law. It's hard to get people to change their ways, but that is going to change and young lawyers are really positioned to take advantage of and pursue the new technology because this industry is not going to be the same in five years and you guys can be a part of remaking it.
Nicole Abboud
Yes, that is awesome advice. I love that you said that. I think so too. I really think that, well, I know firsthand that it's definitely very hard to change things in the legal industry, but they are going to change whether they like it or not.
Catherine Krow
They are going to change. There are lots of dinosaurs who, and I was among them, who did not necessarily see the writing on the wall, because you're so heads down and working so hard. But clients are pushing change and there's just no way around it. And I feel like young lawyers, who are paying attention to the industry, can do so much and especially if they're starting their own firms or their own companies. It's a whole new world.
Nicole Abboud
And you know what? I just got to ask this for my young lady listeners, lady, lawyers who are listening and they want to break into the tech industry. How can they not get discouraged by basically what we talked about a little bit earlier? How it's a little bit harder for women in law and in tech. Can we get some words of encouragement?
Catherine Krow
The reality of being a woman in hard professions like this is that you will be underestimated. Take it as fuel to your fire. Do not believe it. Do not feel. Let it fire you up. And that moment when you take that focus and you realize that you just blowing everybody else out of the water is such a great moment. So just believe in yourself. Do not, do not be swayed from believing in yourself.
Nicole Abboud
Catherine, you are just swell. Thank you so much for your amazing advice. I actually want to grab your contact information and list it in the show notes in case anyone would like to reach out to you or find out more about you, and the business.
Catherine Krow
Absolutely, so my e-mail and I love to hear from young lawyers and mentoring is a big part of who I am and what I believe in it. So if anyone wants to reach out, I really want to encourage you to do that. I'm impressed with myself for spelling.
Nicole Abboud
That was good. I was writing it down.
OK again, those will be listed in the show notes and Catherine, thank you for your time. Thank you for joining us and for sharing your journey with us. It was definitely very inspiring.
Catherine Krow
It was my pleasure. Thank you, Nicole.
Nicole Abboud
Bye.
She's just awesome. Thank you to Catherine and thank you, friends, for listening all the way. I hope you feel inspired to just go after what you want no matter how long you've been practicing, just like Catherine did. It is definitely never too late.
I want to thank you for being such a loyal listener, it really does mean the world to me. Also, if you haven't heard yet, I actually have a YouTube channel that I am trying to get the word out about, but I post new weekly videos and they're tailored to you, my fellow lawyer.
I'm sharing tips and advice on business development as a lawyer. I share behind the scenes at my speaking engagements in case you're interested in kicking off a speaking career of your own. And I just post some motivational messages for you guys, sometimes it's just needed, right? So I'd love for you to subscribe to my channel. You can find it at youtube.com/C/nicole Abboud and that's Nicole, A-B-B-O-U-D until next week, take care.
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