Jason Boehmig, CEO of Ironclad Inc., shares his experience raising $183 million for his contract management software company.
Jason Boehmig, CEO of Ironclad Inc., shares his experience raising $183 million for his contract management software company. He discusses securing approvals, managing tasks, and capturing contract data in a searchable database using Ironclad.
Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today, we definitely have an exciting guest, a guest that is a recovering lawyer, just like myself, and I think we’re going to be learning quite a bit on his journey. It’s definitely not the journey that he thought he would embark on because no one in the family was an entrepreneur, but we’re going to get into that. It is remarkable what he has been able to accomplish. I don’t want to make you wait any longer, so without further ado, let’s welcome our guest today. Jason Boehmig, welcome to the show. Jason Boehmig: Thanks for having me here. It’s an honor. Alejandro: So, originally born in Pittsburgh. How was life growing up there? Jason Boehmig: Life in Pittsburgh was actually really interesting from a historical perspective actually. One of the things I talk about is growing up in the shadow of some of these
industrial titans that existed in Pittsburgh: the Carnegie Museum and the Frick Conservatory. But actually, it was like a depressed economic environment to grow up in the ‘80s in Pittsburgh, and the population was going through a lot of decline and economic hardship. It was interesting to have lived in a place that was once the center of industry but was going through a tough economic environment when I was growing up. Alejandro: Afterward, you went to University in North Carolina. Then you decided to go into investment banking, Lehman Brothers. At that point, investment banking was the time where dollars were flashing, everyone making it rain, but you had to face the not-so-fun part of it. Tell us about this. Jason Boehmig: Yeah. It was a great way to start the career, actually. I learned a ton, and the reason I decided to do it coming out of school was this was a chance to learn a lot
about finance. I studied economics in school, but it’s one thing to study a topic and the other to actually learn it as a profession. I looked at it as I’m going to come in. I’m going to do a two-year stint at one of the great investment banks. I loved working at Lehman and learned a lot, and then figured out what I wanted to do with my career. As the next step, I had always thought about law school but wasn’t sure. I looked at it as this two-year stint to learn a lot, and from that perspective, I was really successful and ended up sticking around for four years and doing an internal transfer over from the IB side to the Sales and Training side of things. Alejandro: So, once everything crashed, everything was imploding, you decided on law school, and maybe that was the thing that pushed you to go for the next chapter in your career, which you felt law was the way to go. You were in New
York City. Here, we’re talking about the city where you have most of the big law firms. I actually used to work in Midtown, too, at a law firm called King and Spalding. Why did you decide to go to San Francisco to practice law when you have some of the biggest firms in the city where you were living for so long? Jason Boehmig: Yeah. Part of the journey was this understanding that I wanted technology to be a big part of my career. At Lehman Brothers, I had the fortune of sitting next to some quant traders. It was the first time I realized there is a revolution in the way that we work happening right underneath our noses. These quant traders were able to tell you things about bonds or securitized products that no one, even if they sat on a trading desk for 30 years, was capable of processing in their mind. You had to process it through computer code. Sitting on the desk there and seeing
that planted the seed of technology seems like one of the great historical transitions of our lifetimes, and it’s exciting to play a small role in that. The center of that universe, particularly back in 2008 when I was leaving Lehman Brothers and in 2012 when I was graduating from law school, was definitely San Francisco and to some extent remained that. That was really why I definitely had the snobbish New York viewpoint of San Francisco of its backwater, and no city is as great as New York. So it was begrudgingly that I moved to San Francisco to practice law after cutting my teeth in New York. Alejandro: It’s interesting here what you got in terms of experience because, on one end, you had access to the investment side of it, so you were able to see how deals were done, what maybe made good companies versus bad companies. And now, you were going into law where you were able to get a
good understanding as to how contracts are written, how to prevent making mistakes when it comes to putting pen to paper, and you did that for a few years. What were some of the things that you learned, maybe some no-noes that you saw with your own eyes that you knew that if you ever were to start a business, you would never have to? Jason Boehmig: Yeah. I think one of the things that I was able to internalize working on Wall Street and making the transition to law is it really is important to have a motivational connection to the work. I enjoyed finance, but it wasn’t the job that I felt I could be happy with for the next 20 years, just in terms of natural interest in the subject. It did influence how I thought about my career in the legal profession and being willing to take that pretty big step back in my career. Working on the street for four years, it’s not a ton of time, but it’s
enough to get pretty senior, and a lot of my colleagues were doing interesting things. All of a sudden, I had just taken three years off of my career to go back to law school, and I was a first-year associate. Eight years deep, almost nine years deep into my career, was like starting over again. But the perspective that I gained was it’s okay to start over if you’re closer to the center of that passion and place that you feel you can get curious about for the next 20 to 30 years. I do think that one single lesson is attributable to a lot of the success of Ironclad. We have just gotten more curious in our space than anyone else. There have been 30+ companies doing what we’re doing, but the level of questions and the depth of curiosity is much higher at Ironclad than our competitors and historical competitors, as well. Alejandro: Let’s talk about that transition from Fenwick and West,
where you were an attorney, all the way to bringing Ironclad to life. At Fenwick and West, you were exploring with technology like building your own site things or your weekend projects, so to speak. What kind of lawyer – I mean, a lawyer of coding is kind of strange, or perhaps building stuff in that nature. Tell us what triggered you building stuff or what kind of stuff were you building that pushed you over the edge to think, “Maybe there’s something I can do here more as a business.” Jason Boehmig: Yeah. I would say my inspiration for doing this was the quant trader, and that’s how I wanted my practice to work. If you think about what the quant traders are doing, they’re using computers in a new and computer language in a way that helps them do their core job, which is trading. They’re still functionally trading. They’re not just pure coders. The objective is to trade better and
gather new insights that help you make better trades. That was how I conceptualized my technology involvement at the law firm. I’m still going to be a lawyer; I’m just going to be a tack-enabled lawyer. It turns out that I’m going to have to build a lot of that tooling myself because it’s just not in the market. My intent was never to build the technology. My intent was to go find it in the market. It was only when I couldn’t find it in the market that I realized I’m going to have to make this if I want it to exist. So, I went out and hired a coding tutor. I taught myself to code over a multi-year time span and started making very simple applications, as simple as writing a Visual Basic script that would automatically compare a set of documents in one folder with the set of documents in another folder and generate a bunch of PDF redlines. You, as a lawyer, know the amount of time you
spent clicking buttons to make a red line for a deal packet is actually insane. What I was really trying to do is not the really high-end work, but just the low-level administrative work. That just proved to be a lot more fruitful than I would say I thought it would be going in. I thought I would discover ways to do this that existed in the market, and I thought that I wouldn’t be able to get as far as I did just hacking together on my own time nights and weekends. Once I started to go down that rabbit hole, I realized there’s really a market opportunity here, especially around this common problem that every business has, which is making and keeping track of its business contracts. Alejandro: Yeah. So then tell us about the moment where all of a sudden, you said, “This is something that I have to do.” Obviously, for you, it was not a good time. You had $300,000 in student loans, which is
outrageous. It’s just…