Originally recorded on LexBlog's YouTube channel.

Catherine Krow, former founder of Digitory Legal, is now the Managing Director of Diversity and Impact Analytics at BigHand. Digitory Legal is now BigHand Impact Analytics. To learn more about Impact Analytics click here.

Catherine Krow, the former founder and CEO of Digitory Legal, sat down with Kevin O'Keefe from LexBlog for our Legal Tech Founders series at the Legal Geek 2018 conference.

Video Transcript:

Kevin O'Keefe
I'm here at Legal Geek and I'm talking with Catherine Krow of Digitory Legal if I understand that. What is Digitory Legal?

Catherine Krow
So Digitory Legal is a cost prediction and management platform for complex litigation. We transform and analyze billing data and use that data to create predictive pricing models and then customers can leverage our platform to manage costs over the life of the matter. 

Kevin O'Keefe
So looking at the data from history?

Catherine Krow
Historical data, yes. 

Kevin O'Keefe 
And you're sitting there as an outside company, and I'm just asking you this naively. You have to get that data from, or your licensing solution to the firms, so that they can do it on their own or you're getting a pool of data from multiple firms, right?

Catherine Krow 
We're getting them a pull of data so that we can use, from the firm, and then we will do the analytics for them and give it back to them in a way that actually tells them what happened and they can use it to cost out cases for their next engagements.

Kevin O'Keefe 
How did you get into this? I mean, you are a lawyer, how long did you practice?

Catherine Krow
17 years.

Kevin O'Keefe 
Equal 17 years, exactly 17 years. And I felt like I’m going to do it for the rest of my life, but I actually enjoy it. I was having fun! When was the moment you said, I think I got this idea?

Catherine Krow 
So like a lot of legal tech founders, I started Digitory Legal to solve my own problem.

Kevin O'Keefe 
Right.

Catherine Krow 
But when you're a partner, your problem isn't so much about the practice of law, that's kind of the easy part. It's really about the business of law. Exactly, and ironically, the moment that set me thinking about this path, was from a practice of law perspective, probably my biggest success. I tried a case that had huge potential liability or downside and not very many people thought we could win it and we completely defended, it was a great victory. And a month later, the client pushed back on the bill and I realized at that moment that the market had changed. I saw the rise of legal operations and legal procurement before they even had a name. And I realized that there are so many different ways that we could have done better with more cost transparency, better technology, better processes. So I built Digitory Legal to provide that cost transparency.

Kevin O'Keefe 
Are you saying you've built it?

Catherine Krow 
Yes

Kevin O'Keefe 
You are not a coder.

Catherine Krow 
Yes, I am not a coder.

Kevin O'Keefe 
Who actually, and I understand what you mean, you've built the concept, the company, and what it could do. As you had to get into development, where'd you get that from? Where did find those?

Catherine Krow 
So, fortunately enough I live in Silicon Valley and have been there for a very long time. So, I tapped into the network and so my CTO has a lot of startup, successful startup, experience. He was the CTO of a company called flutter.com, which was bought by Betfair, the 1st and largest online gaming system. So access to talent like that was something that I had based on time and location.

Kevin O'Keefe 
What firm were you with?

Catherine Krow 
I was a partner at Orrick for many years.

Kevin O'Keefe 
Yeah, Orrick is a reasonably progressive firm.

Catherine Krow 
Yeah, yeah.

Kevin O'Keefe 
It still is. Yes, you maybe didn't have the hurdles that other people did, like me totally naïve, with no connections, knowing nobody. I have to start finding people to meet, who know much more than I do.

Why do you though? I mean, you are going to say, OK, I'm going to go from practicing lawyer. We're doing great work, like you just described it, to have a legal technology company. You didn't go, you weren't working for 17 years to groom yourself to be a founder and to run a company.

Catherine Krow 
That is true, and I did really like practicing law. But I realized that there was a moment when the entire industry was changing and I had a choice. I could take that moment and that opportunity, part of that historical change, or I could put my head back down and try cases for bigger companies and harder cases for the next 20 years. And I'm more of a risk taker, probably more than most. I've always followed my own path and I wanted to take that moment. It is now or never.

Kevin O'Keefe 
What did your partners think? 

Catherine Krow
ughhh

Kevin O'Keefe 
I assume somebody had to come in and leaned in your office door and say, what do you mean? What are you doing?

Catherine Krow 
What on earth are you thinking? So, I will remember that one person when I told him that I was leaving. He said, “Well either you're going to be calling us up and asking for a job in two years, or we're going to be working for you”. I decided right then which side of that equation I wanted to be on. It was very motivating, so I think there was somehow on earth is she going to do it. But that just drives me harder.

Kevin O'Keefe 
Every company that starts, I mean you're starting from scratch. You're creating something that didn’t exist before. There is going to be highs and lows, some are cyclical other are bigger moments. Are there moments that you remember, where you go “Oh my God, does it have to be this hard?” Am I going to make it through this?

Catherine Krow 
Yes! There have been moments when I thought, Oh my goodness, what am I doing? And part of it is I am a mother of two and I found the only thing harder than trying cases, which is starting your own company.

Kevin O'Keefe 
Yeah

Catherine Krow 
So I moved to London for a large part of this summer and was away from my family to participate in the fantastic MDR lab program and that was personally very difficult, professionally great. So there have been challenges, but we've overcome them.

Kevin O'Keefe 
What was the moment when you thought this is going to work? I mean, this is, maybe you never want to say that. The moment I remember from here, it was like when the first check came and I asked them to send checks, not wire any money or do any transfer because I wanted to touch the check from a major law firm.

Catherine Krow 
I can neither confirm nor deny that there is a picture of that somewhere on a wall, somewhere. 

Yeah, I mean signing the first enterprise customer was a huge moment. But some of it was I was fortunate enough, perhaps just the curiosity factor, to get connected with some very high-level players in the industry and having access to those folks and showing them the data and having them go, “WOW, I need that that”. That was an injection of adrenaline that no verdict can have that kind of moment.

Kevin O'Keefe 
Yeah, you're walking out, and you are going OMG, this is going to work.

Catherine Krow 
There have been moments like that.

Kevin O'Keefe 
Did you self-fund the company or did you get investors? What did you do?

Catherine Krow 
A combination of bootstrapping and angel investors.

Kevin O'Keefe 
And how long did you bootstrap it? Did you go out and get capital right away or did you do it on your own? Just curious, there are other people to hear your story.

Catherine Krow 
Yeah, it was a combination right from the get-go. I had a number for bootstrapping, who were willing to do and then we needed to know that there was flow coming in from angels. Particularly, you know, people who knew the space. So both.

Kevin O'Keefe 
There are other people here today that are like you before you started a company. They have an idea like you, what would you be telling them? If they sat down and they say, you know, they look at you as somehow an overnight success. Like you are magic for them or whatever. What would you be telling them? What feedback would you give them? If they are thinking about doing this, I'm in a law firm, what would you be suggestions to talk to them about?

Catherine Krow 
Understand that this is the hardest thing you will ever do in your life, and it is not for the faint of heart. So, you have got to want it and you know what you're getting into. You're going to work hard. You're going to have highs and lows, and there are some stats out there, the sales cycle is tough. So you really need to believe deeply in what you're doing and have a plan. And don't just look at the Silicon Valley startup stories like it's just some overnight success. There is blood, sweat, and tears in this before you break through.

Kevin O'Keefe 
But it becomes the new normal. I mean, you're when you are in it, it's what it is. Totally different than when you're practicing law.

Catherine Krow 
It is very different from practicing law, but as I said, I found the only thing harder than trying cases is starting my own company.

Kevin O'Keefe
Well, thank you very much. 

Catherine Krow 
Thank you, thank you so much.