Kevin O’Keefe: Who am I talking with?
Ryan Alshak: Ryan Alshak
Kevin O’Keefe: And Ryan, what do you do?
Ryan Alshak: I founded a company with my best friend, Kourosh (Zamanizadeh), and we started a company that’s automating time and billing by leveraging machine learning.
Kevin O’Keefe: How long ago did you start it?
Ryan Alshak: 2016
Kevin O’Keefe: Two years. How’d you get the idea to do it? Like, what made you crazy enough to say, “okay, we’re going to start a company that does that.”
Ryan Alshak: It was a scratch your own itch situation. I was a corporate litigator for three years. I hated timekeeping. It was awful, and I couldn’t believe that was the way that it was done. Kourosh and I went to Berkeley and graduated in 2009, and a had front row seat to a lot of our best friends, starting and ultimately selling very successful companies and so we’ve always had that seed in the back of our minds and wanting to do something ourselves. I went to Berkeley for undergrad, and USC for law school. Kourosh is from Washington, and I’m from Los Angeles.
Kevin O’Keefe: Okay, so you were getting the exposure to startups, or seeing what’s going on around that area.
Ryan Alshak: We were on the front lines. We were in the Bay Area, and in 2009 the economy tanked, and a lot of people weren’t getting jobs, and so they just had to go create their own jobs. And then that became kind of the first wave of the new Silicon Valley. As a litigator it’s a zero sum environment. Best case scenario, I take from your pocket and put it into mine. When you’re doing your startup or you’re creating a company, you’re creating value out of nothing, and that was always something that really spoke to us.
Kevin O’Keefe: Yeah, when somebody says, well what is a startup? Or what does that mean? Because somebody will say, “well, I took this from this company to do this.” No, no, no. You create something that didn’t exist.
Ryan Alshak: Not only didn’t it exist, but fundamentally everyone else has failed at it previously and you are crazy enough to think that you can be the only person to push through and ultimately solve this problem that everyone else is still trying to solve.
Kevin O’Keefe: Right. So how long had you practiced law before you did this?
Ryan Alshak: Three years. Three years.
Kevin O’Keefe: Did you start to work on the idea while you were still practicing law? Did you say, “okay, I’m burning the boats, I’m done with that, we’re going over here?” How did it all come about?
Ryan Alshak: We had the idea and then we teamed up with two engineers and a UX designer, and kind of identified whether it was possible. It’s a really complicated problem, both technically and user workflow-wise. And then when we decided that it was possible, it just took a lot of work. I quit cold turkey because I think it’s very important for the rest of the team is to see that I believed in this. And then we had another co-founder that was actually in law school and decided not to take the bar. No safety net, let’s go.
Kevin O’Keefe: How’d you support yourself? How’d you guys get by?
Ryan Alshak: You don’t want to know. We consolidated everything. We started all living together. I was sleeping on my brother’s Futon. I was taking Greyhounds up and down. I went from flying in first class seat seats to the Greyhound. We bootstrapped it and then were finally able to raise some outside capital about nine months into building and now have since wrapped up a pretty significant venture round.
Kevin O’Keefe: From when you started to build it to the time that you had your first customer, how long did that take?
Ryan Alshak: So there were stages. We got paid but we were still building, so there was a moment where a lawyer saw the software working and you could have sworn that we were Elon Musk sending a missile. I think the shock on his face when he picked up his phone, hung up and it was a perfect timing tree, in realtime, populating, was the most incredible moment. So that happened January 21st of this year.
Kevin O’Keefe: That was a question I was going to ask you, what was the day you knew this was going to work?
Ryan Alshak: That was the day. I saw the legitimate shock on his face. How excited he was, for a lawyer, it was like I just gave him Christmas morning. To turn the worst part of your job into something that made you smile, that order of magnitude difference, I knew we had something special.
Kevin O’Keefe: What was the low point? Is there a point where you knew when that was?
Ryan Alshak: We never had that point. I’ve always believed that it was just a matter of working hard enough accomplish it, because we had the team. When you surround yourself with the right people and the right attitude and that ambition, and started knowing that if it’s possible, why not us? Even the lows didn’t feel like lows because we knew we were gonna make it through. One of our core values is “dance in the rain.” Don’t wait for the storm to pass. Enjoy the lows. Those are the fun parts, and that philosophy has been really important.
Kevin O’Keefe: What’d you learn? I mean, it’s a short period of time, and you have many years to go and grow and be successful. What have you learned so far? What was most surprising?
Ryan Alshak: It’s not even business related. It is that you are one person, and the way that you are at home is the way that you are at work and that’s something that we fundamentally believe. We want to give you back time and what you do with that time whether it’s spend time with your family, deliver high value work to a client, that’s your prerogative, and you should own that. I see it in my life – when I’m happy, I’m happy at home and seeing that play together, the notion of work life balance.
Kevin O’Keefe: That’s what Clio talks about. If you’re at the Clio Con conference, they’re talking totally about productivity and we’re giving that back to you in your lives. Here’s what you should be doing in your life by the time that you saved. And it’s tremendously moving when you’re sitting in the audience, listening to that. What would you tell other legal tech entrepreneurs who maybe aren’t started yet? They’re thinking about it, and I’m hearing great stories because you’re practicing in a relatively short period of time. You’re saying, okay, we did it based on savings, but you don’t have a huge amount of savings when you’ve only been working a short time. What do you tell people that are thinking about quitting their job or maybe even going to do it right out of law school or, we talked to one earlier, never went to law school – found the law interesting as a computer scientist – what would you tell somebody?
Ryan Alshak: It’s a drug. Once you have a taste of working for yourself and building something that you’re passionate about, you will never look back. I have never looked back one day. Even when my bank account was nothing, even when I was riding on that Greyhound, or sleeping on that futon, I was smiling the whole time. That’s what it’s about at the end of the day. Am I happy doing what I’m doing? I love what I do, and I’m passionate about what I do. And I took what was the biggest pain in my working life, which was timekeeping, and that is now my passion, to help other people to make sure that no one has to go through that.
Kevin O’Keefe: How do the products sell? Just out of curiosity, do you sell to the firm as an enterprise solution?
Ryan Alshak: From the top down, yeah.
Kevin O’Keefe: And you looked at the drudgery of the time. I mean, that’s how I became a personal injury lawyer. We did it on paper, man, so there were no keyboards, computers. Everything you wrote down was carbon, and you turned in rubber banded things, and you had carbon sheets that went into books to back it up. I mean, it was bizarre. So if I’m on that phone call, or I’m working on some memorandum or whatever it is, what does it do so I don’t have to be doing what I used to do, whether it’s keying in time, putting in the client, that type of stuff. What did you figure out that could be done that could save so much time for people?
Ryan Alshak: It is plugging into the systems that you’re using to create mobile work, and it’s layering machine learning on top of it, to get context. To understand what is it you’re spending your time doing it, who is it for, for what is it about, what legal code applies? That machine learning is our secret sauce, and it’s something very sophisticated, and is just now starting to get fleshed out. I don’t use AI – really it’s about machine learning, and about understanding your time, not just giving you a full ledger of everything you did in a given day, which is very useless.
Kevin O’Keefe: So what you are going to recognize is that you were talking to particular client, on a particular type of matter, and it knows the terms years you use, and it can create the bill for you.
Ryan Alshak: Exactly.
Kevin O’Keefe: So when you’re looking at it, somebody could glance over the thing, but it’s already saved all that time.
Ryan Alshak: We like to say right now, lawyers are given a blank canvas, and they say “paint,” and we paint 95% of it and they add the brush strokes.
Kevin O’Keefe: So how many people work in the company today?
Ryan Alshak: We’re up to 11 full time, and we’re hiring aggressively. We just wrapped up this round really focused on finding the best of the best.
Kevin O’Keefe: Who are you hiring then? What areas?
Ryan Alshak: Engineering. It’s all about builders. We just hired a full time machine learning engineer, PhD from Brown for particle physics. We’re talking about world class talent that we’re throwing at law. Recruiting engineers from Google, Amazon, Apple, you name it.
Kevin O’Keefe: And you have no background on technology. You’re not a coder?
Ryan Alshak: I am not a coder at all. I can play one on tv.
Kevin O’Keefe: And that’s about me. I can say yeah, there’s code on the machine right now, I can see it on screen. People asked me about that. Do you ever get asked a question? Like friends that go, “wait a second. What do you mean you have a legal technology company. You don’t know anything about technology.” What do you tell them?
Ryan Alshak: You learn. I was pitching in Silicon Valley, and we were pitching an AI-focused company. I’m talking deep tech. And they only invest in very heavy AI companies, and we were going back and forth for about an hour, really asking deep technical questions and they left that meeting giving us a terms sheet and I walked out of that meeting and it hit me, that a lawyer created an AI company. What the hell was I doing? It happened, because when you are passionate about a problem, it’s all about solutions. It doesn’t matter what the solution is, you’ll go figure it out. For us, we realized that it was machine learning, but once you are committed to solving their problem, you figure out a way to do it.
Kevin O’Keefe: Let me ask you another question: When you start to employ people and they have lives, they have rent, they have mortgages, you know, if they haven’t already, they’re going to have kids, some of them get married, and you realize “we created this thing and we’re all supporting each other.” Has that ever hit you? To me, it’s a very moving experience, when I sit back and think about it.
Ryan Alshak: It is so humbling, and I am forever indebted to everyone on this team because they took, ultimately, a risk on me and a crazy idea, and I owe them everything back tenfold. It’s something that motivates me every day to write my ass off, because I know if I do wrong by then, I’d been doing wrong by the people that took the biggest risk on me.
Kevin O’Keefe: Yeah, you’ll feel the worst. You might even feel worse about it than anybody.
Ryan Alshak: Of course, because I would be responsible, ultimately, for their risk blowing up in their face and that’s on me to make sure that never happens. That’s something that’s very personal to me.
Kevin O’Keefe: Well, thank you much, sir.