On this week’s episode of Lawline’s Lawyers Who Lead podcast, Sigalle discusses the concept of Leading by Putting People First with Tony Thai, Co-Founder, CEO, and Chief Engineer of HyperDraft, a software that allows lawyers to draft and analyze documents better, faster, and smarter so they can live more of their lives outside the billable hour. Tony discusses his road from software engineer to lawyer to CEO, and how his mission to provide lawyers with tech tools is grounded in a people-first and human-centered approach. Listen to the full interview or read the highlights of Tony’s interview below! Transcribed answers were edited for readability.
On What Makes a Software Engineer Become a Lawyer
Family, Stability, and Tired of Paying Legal Bills
Like a lot of people, there are multiple reasons why I went to law school. One of the ones that I say that’s public facing is I was tired of paying for legal bills. So I went and got a legal degree because like any self-respecting engineer, I always think I can do it better.
And the other part of it is I wanted to do one thing that was nice for my mom and my aunt, who basically both raised me. Just getting these extra few letters behind my name helps make them feel like they weren’t complete failures in raising me, like, I’ll go do that. So a big part of it was for family as well.
I mean, let’s be honest, right? If you’re coming from an immigrant family, the prestige and the pride around having a kid who is a professional, either a doctor or a lawyer, that carries with it a lot of weight and a lot of “Hey we did this for a reason and it’s paid off.”
And the other part of it is stability. My parents didn’t always have a bunch of cash when we were growing up, we were quite poor and so they saw that as the golden egg, if you will. It’s like, if he gets that job, he’ll have a stable, high paying gig and then all his problems are over with. And so for them it was the stability plus the prestige.
On Being an Entrepreneur While in Law School
“I Was Like a Kid in a Candy Shop Getting to Learn About What Makes a Company Successful”
I can’t help myself. I had a business when I was in college. I worked full-time running that software engineering and tech consultancy business.
I went to law school, I had zero intention of practicing law besides for myself. [I rationalized] I’ll have leverage. I’ll understand contracts. It turns out that’s not really the case. When they put you through law school, you understand the concept of consideration, but not much else.
But then I lucked into working for this boutique law firm. Picked up on corporate transactions early on in my law school career, which I don’t think a lot of law students have that opportunity because law school is mostly focused around litigation. So if you want to do litigation, that’s great. But corporate law is kind of, you know, an ephemeral concept that’s like, ah, yeah, that’s the stuff that happens before litigation.
So I got to work on M&A deals and venture financing. As an entrepreneur, as a business owner, it was really interesting to me that whole process. I was basically like a kid in a candy shop getting to learn about what makes a company successful so that they can get investors and then ultimately get sold.
I [also] got a group of the law students together and I petitioned for us to get a course at the business school, to a class called entrepreneurship. We started up another business during the semester, and then we got the top score in the entire class.
On The Evolution of HyperDraft
I Identified a Problem in Law School and Iterated on It While Practicing
The idea was planted in law school. One of my law professors, Michael Chasalow, and I would talk. I’m just like I don’t get it. As an engineer, we don’t build the same thing twice. We don’t reinvent the wheel every single time. And I’m like, I don’t understand why in the legal field, that’s a constant issue. So I started hunting for products for us at the small business clinic. I worked at USC Small Business Clinic and I was hunting for legal tech tools to help make our lives easier.
So it started there, but really the idea started to take shape when I was in my first year of practice and I was getting just pummeled with work. I’ll tell you the exact moment when I came up with the first iteration of one of the apps I worked on. I’ll never forget this. I was sitting down in this partner’s office looking at my feet because he was about to assign me one more deal. I looked up and I was begging, basically. I said, I can’t do this. I’m going to break. I remember him turning his face away from the computer and just looking at me and saying, you just got to figure it out and then turned his head back.
So I went back to my office. I’m a happy person, as you can tell, but, as depressing as it sounds, I wept. I was like I’m going to get fired. I’m done. I’m so sad. I don’t sleep enough. I’m depressed. But my whole mentality was if I’m going to go out, I’m going out with a bang, right? And so I’m like, all right, with everything you know, Tony, if you’re gonna get fired, you’ve got to give this a shot. So what are you going to do? Okay. I gotta get all these concepts from a spreadsheet into a word document, spreadsheet, word document, spreadsheet, word doc – um, you know what, I’ll write a damn program to do this.
So in 45 minutes, I was able to get a script out that converted this Excel spreadsheet into a disclosure schedule that I needed, that would’ve taken me probably 13 or 14 hours. And so it did that and I will never forget. I slept in my office. I was like, ah, this thing is working. I’m just going to sleep underneath my desk.
That was the first iteration. That’s how we started it. But I’m a skeptic, like most lawyers. And so I was building this out and I’m like, man, I got to figure out product market fit and all this other stuff. So I stuck around mostly for R&D. And my previous boss will back me up on that cause when I interviewed, I [was] very upfront and very transparent [that] I don’t want to be a lawyer forever. I just want to build tools for you guys. And they’re like, that’s fine. And they’ve become friends and investors in our company since.
On Why It Was Time to Get HyperDraft to Market
The Pressure Lawyers Were Getting at Law Firms + Lawyers Were Remote and Had a Higher Threshold and Acceptability of Technology
Last year was when it all came together. We saw the amount of pressure that lawyers were getting at law firms and just everywhere.
That’s something I focus on a lot with our team is we have to be empathetic with our users. I think that’s one of our key advantages is we’ve been there. We’ve stayed up until 4:00 AM every single night for weeks on end. We know what it feels like.
We realized, all right, now’s the time. We need to go out with this. People are working remote now so there’s this higher threshold and acceptability of technology. It’s a good time to attack. And so we left early last year, I think, February of last year. We’re about to hit up our one year mark here.
On How To Create Meaningful Relationships
Don’t Promise the World While Thinking Maybe You Can Deliver Later. Instead, Build Credibility and Walk the Walk Now.
You know, I don’t wanna make this so broad sweeping [that] it just sounds like an overgeneralization, but we hear about the transactional aspect of relationships. And so people are always looking to get something out of someone else. So this sounds very theoretical and abstract, but let me apply it to my dealings with Jace.
Jace Lynch [is] my co-founder. If you ask him, he might refer to himself as a hostage. The funny thing is he never agreed to co-founding the company with me. He just came along. He [was] my junior associate that I trained up when I was at Goodwin.
Jace is a human being, right? I treated him like a human being. I trained him up, but I also gave more than I took. And that’s always my core belief. Actually I asked him a few months ago why he joined. And he’s just like, well, Tony, you always had my back and like, you always gave, and you’re just built for this.
And I told him, you want to know a secret dude? Every time I took a bullet for you, I thought about throwing you in front of it. He was just like what? I’m like it’s so easy to throw somebody else under the bus. It’s way harder to see it, identify the desire to do it, and then choose the right thing to do for your team. And I think that people see that.
And it’s all show, not tell, right? Show, not tell. I’ve encountered good leaders [and] bad leaders and the common trend I see is the good leaders always just showed. They weren’t just talk. They didn’t just say, oh, I’ve got your back and then go to bed [as] you make another cup of coffee and pull an all-nighter.
So I think it’s building that credibility with people and walking the walk and not just talking the talk. I think too much these days, people think oh, I’ll just promise them the world and then maybe I can deliver later. Whereas at least my personal mentality is it’s our job to do right by the people we work with and to show them how to lead.
On Recruiting Top Talent and Building Successful Teams
Choose People Based on the Quality of Their Character, Not Just Their Pedigree and Background
I’ve spent time in companies and like big corporations and what I realized is the team and the person that you work with is so much more important than just their experience.
Experience we can collect. We can find advisers for and do our own personal research, but the type and the quality of the person. That’s so hard to come by and you hear this all the time. You can ask my team, my greatest fear is not being able to work with these people.
These people know that I’m gonna take care of them because it’s not our only project, right? These are the people I want to work on difficult problems for the rest of my life. And is that realistic expectation? No. Is it a little bit clingy? Yes. But I like these people. Like I choose people based on the quality of their character, not just their pedigree and background.
That’s the other thing is like seeing the potential in people seeing what my old law school professor, Michael Chasalow, calls raw materials. When you see people with such great raw materials and they’re doing something that isn’t utilizing it, man, it hurts. Right? Like it just hurts. People are creative. That’s the beautiful stuff about being alive and like working with people is like seeing how creative they can be. So how I pick people is raw potential on top of all that stuff.
A lot of what people misunderstand about leadership is it’s not just a great leader that makes a great team. It’s also having great teammates. I’ve hired poorly and actually it’s when I neglected everything that I’m looking for now. When I just went for skills and neglected to look at personality fit and quality and character of the person. [When] I just said, I don’t have time for this. I need to find somebody who has skills in Y and Z categories. Let me hire that person. Great. That person did not give 2 cents about me or the team. They just cared about getting the job done. And what I realized over time is that this is not a good formula for building a long lasting team because you need to be able to see and anticipate the needs of the team. Long-term not just short-term.
On HyperDraft’s Hiring Process
We See How Candidates Interact and Solve Problems Individually and as a Team
We had an unusual interview process with Ashley [our CMO]. I had her meet other teammates and I had her meet my friends and I had her meet my clients and I watched the interactions. We would whiteboard problems. I’d bring up a problem and then see her participation in it.
And that’s how we interview, seeing how people not only solve problems by themselves, but how they solve problems as a team.
On HyperDraft’s Core Values
Fail Fast, Fail Openly, Over-Communicate, and Have Fun
I send out an email to every new person that starts and the bullet points we use are: 1) fail fast, fail openly, 2) over-communicate, and 3) good luck, have fun (which is a StarCraft reference cause I’m a nerd).
What “fail fast, fail openly” addresses is – I think lawyers…feel like we can’t fail. It’s like this thing, that’s absolutely fatal if we fail. But that’s not how the world works. Like we fail all the time. We make little mistakes, that’s just how life works. So it’s dropping the ego around failure so that we can fail together and learn together.
That kind of leads into the next point of over-communication. Making sure that people know to over-communicate their thoughts cause I don’t want someone like sitting in the corner and being like, well, I had this idea, but I never said anything about it. That’s as good as not having any idea. I need you to say something. I can’t read your mind. If you feel like it’s an important suggestion just suggest it. There’s no shame here. No one will make fun of you. If it’s wrong, it’s wrong. If it’s right, it’s right. And all of us will row in that direction.
The last part is just like learning to have fun. Life’s too short for us to be dreading what we do with so much of our lives. Like if you take a step back and do the math, don’t, don’t do it because I have, it’s not good, but you realize how much time you spend working. You’re just like, oh crap. Yeah, I should probably enjoy this. I don’t have to enjoy every part of it, but I should enjoy a good chunk of it.
On The Importance of Creating Legal Tech with a Larger Purpose
We Create a Product That Gives Lawyers Extra Time with Friends, Family, and To Give Back to the Community
For me, it’s the love of law, but it’s also the love of the people that are doing it. I keep apologizing for being cheesy, but these are friends and family, right? Like these are the people that used to have more time to spend with their community and help move the community forward. And it bugs me greatly that these people don’t have the time to not only spend time with their friends and family, but to give back to the community, right? These are the people that used to be on their school boards and help with pro bono projects and community building projects.
How can you honestly say that these are the same people that are doing those kinds of projects when you’re forcing people to bill above 1900 or 2000 or 2,500 hours a year? Your best legal minds are doing that and it bugs me. So that’s a big part of the mission is like getting people their lives back. And remember what I said before, my recommendation is always if you’re going to do something don’t expect direct repayment, my only ask is that people pay it forward. Spend that time giving back to the community, giving back to your friends and family. That’s what life’s about and we’re here to help.
On How to Keep Teams Aligned with the Company’s Mission
Help Employees See Clients as People and Name Projects After the People You are Helping
I’ll give you a good example. Our CFO is not a lawyer and I’ve shared stories with him, spent time with him, taken him to events and introduced him to other attorneys and just gotten other people to share their stories. It helps give them a lens around [the fact that] these are people too and these people have passions outside of being a lawyer.
We name our products and projects after people. So we can call this project Diana, right. Or project Bobby. And it comes from a user story, right? Usually we get fan mail, sometimes we get emails from people saying I stayed up all night, I had to do this stupid thing and I missed my kid’s recital. Stuff like that. So we named the project after them and that rallies the troops to that mission because yeah, project, I don’t know, Exodus, sounds cool and techie, but project Sean, you know, getting Sean to be able to attend more recitals for his daughters, that hits home in a way that’s way more human than I could ever do by like coming up with a cool brand. They then realize that this stuff that they’re working on impacts people’s lives on a day-to-day basis. That’s how we do it here.
I learned this from a CEO of a biotech company that builds technology to save people’s lives. Think about that. Like the impact that their project names have on the products that they’re making, they’re saving lives. And we’re not doing anything near that. I’m not a doctor. I can’t save lives, but I can save people time. And if that’s all people want these days, it’s a good mission for us who aren’t healthcare providers.
On How Engineering Concepts Can Be Carried Into Legal Practice
Don’t Just Ask “What If”, Also Ask “So What?”
The same concepts and constructs for drafting a contract or a brief, or any of these other procedural items, you realize that being a software engineer and a lawyer is not that much different. So I carried over a lot of concepts I learned as an engineer over to my legal practice.
One of the things I talk about a lot is like seeing around corners. One of the pieces of advice I got from my mentor early on is good lawyers ask what if, what if, what if. Great lawyers follow that up by saying so what, so what, so what. It’s such a core concept to like the practice of law, because I think as lawyers we want to cover every single possible risk, factor, and scenario that we don’t think about the business practicality of doing all of that. So you have the same problem when it comes to engineering, we can’t account for every single potential error. Just accounting for the stuff that might be around the corner is a really good skill set as an engineer.
So you can carry that over with the legal practice, it’s really beneficial to figure out okay, yeah, that could happen but what’s the likelihood? Pretty low. Let me account for this other situation, that’s more likely, and then put that into the draft of the agreement.
On Leadership in General
Good Leaders Find Intrinsic Value in Leading Others, They Don’t Treat Relationships As Transactional
I try to make sure that the team understands that it’s a cop out to say, I wasn’t born like this. I wasn’t born a leader. I wasn’t born to sacrifice. I wasn’t born to do all these things. And then you realize actually it’s a choice, right? It’s a choice that you can make and it gets easier and there are benefits from it. But I have to tell you, the people that seek out the benefits, it doesn’t usually turn out the way that they want it to. You have to find the intrinsic value of the action, right?
Showing someone that you can be a better person and a better leader by sacrificing. And that the only payout is that they do that for somebody else. That’s my goal. You can’t make it a transactional relationship where it’s like, oh, I do this for you and then you do this for me. It needs to be a, I do this for you, please do this for other people. And, you know, if you do it for me that’s great.
On Leadership in Law
Leadership is a Position of Service, Not a Position of Hierarchy
I think it’s something that we miss a lot, but it’s this concept of servant leadership. You have to sacrifice. Leadership is a position of service not a position of hierarchy.
There’s one phrase that I would hear from one of my mentors in law school that caught me off guard when he first started saying it. We’d hang out. He’d give me all this advice. And at the end of the meeting, every single time it was just how else can I help, Tony? It warms my heart and it kind of hit me because I’m like, how else can you help? You’ve been helping me the entire time. And what a question, right? So I think leadership in the law needs to be circling around that concept and it can be as simple as asking your people. Okay. How else can I help?
On the One Thing He Could Improve in the Legal Industry
Shifting the Workplace From a “You vs. Me” Mentality to a More Collaborative Approach
I think about this all the time. There’s too many abstract concepts. So I’ll talk about one thing, which is in the practice of law. I think it’d be nice if collaboration were emphasized more. I think as lawyers, we think about things in a “you versus me” situation so often that it’s hard to break out and [and ask] what about us? How do we work together? So that’s one thing that I would want to change about the legal field is, as a general premise, how do we think about being more collaborative and working well with others?
On What People Misunderstand About His Work
We’re Not Trying to Replace Lawyers with Tech, We Bring Them Back to a More Humane and People-Oriented Business
That I’m trying to replace lawyers? People constantly ask me, what will we do once your technology takes over? And I’m like, the practice of law is one of the most human professions. I know it sounds weird, but it is literally the establishment of rules between people, by people, about how we interact with each other. There is no technology that will ever sever that line. So, no, our job is actually quite the contrary. Our job is to try to bring lawyers back to a more humane and people oriented business.
On How He Starts His Day
15-20 Minute Meditation Every Morning
I meditate every morning. I wake up and usually just sit up in bed and then I start with a 15- or 20- minute meditation. And through that process, just think about what I wanna accomplish that day. Last five years I’ve been [doing] that.
On the Most Influential Book He’s Read
Daniel Kahneman’s Thinking, Fast and Slow
Daniel Kahneman’s Thinking, Fast and Slow. I think that might be cliche, but maybe not, maybe enough people haven’t read it. But Daniel Kahneman is an economist. In that book, he really talks about the psychology of human decision-making that’s really fascinating. And it is a good way to peel back how our brains work.
On a Piece of Practical Advice to Leaders and Future Leaders
Invest Time Understanding Your Thoughts and How You Want to Contribute
Listen to yourself a little bit more. I know that sounds a little bit abstract, but you should listen to your thoughts a little bit more. And if there’s so much noise and you’re so busy that you can’t find the time to do it, I would say invest and figure out a way to build in time so that you can think about what it is that you’re contributing.
Lawyers Who Lead is a weekly podcast that celebrates lawyers who are making powerful changes through extraordinary leadership. Each week, Lawline’s Chief Storyteller, Sigalle Barness, interviews a lawyer who is driving meaningful change in the legal industry. Guests represent a diverse and exciting range of experiences but with one common thread, the pursuit of bettering the legal profession.
Each episode explores the guest’s journey to leadership, the underlying principles that helped them make an impact, and devises ways listeners can apply these concepts in their own lives.
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