MEET Jason

Jason Boehmig is co-founder and CEO of Ironclad, the digital contracting platform for modern legal teams. Before law school, he took a four-month motorcycle trip from New York to Seattle, through 26 U.S. states—and learned to code during his downtime.

What is something you’ve learned that you lean on daily?

When I was in college, I got to take a poetry course from Maya Angelou, who was incredible. The entire semester was based on a line from the Roman poet Terence, “homo sum, humani nihil a me alienum puto,” which translates to “I am a human being. Nothing human can be alien to me.” She used poetry to help each of us empathize with a new experience. Everyone was assigned a poem that put them out of their comfort zone. A football player from Alabama was assigned a Robert Burns poem about a red rose in Scotland. I’d never really traveled abroad, so she gave me the Percy Bysshe Shelley poem Ozymandias, which is about an explorer.

Ironclad is built on empathy, too—it’s one of our four company values. When we were just getting started, we once took the whole team to visit a customer in Colorado so we could see what their day-to-day work was like, and that trip changed our perspective on what we should build. We realized that to truly help our customers, the platform had to be able to handle any type of contract, even though conventional wisdom was to start doing one contract type well and build from there. Because of our empathy with our users, we knew we had to take the more ambitious path.

What one piece of advice would you give someone starting a company?

The biggest advantages come from genuinely caring and being curious about your space. At Ironclad, we’re thinking not just about the tactical issues we’re currently working on, but the fact that the legal profession in general is in crisis. In most roles, the work-life balance is terrible, and attorneys have very high rates of substance abuse and suicide. We want Ironclad to be a force in changing that trend.

A good example of our curiosity: I took a trip with a few teammates to Seoul recently to support a key customer. By the third day, everyone was tired and jet-lagged, but after our final presentation we stayed out until midnight just talking about what we’d learned that day. And it was fun! It was one of those things where no one wanted to leave. I think if we can keep up that level of engagement, just simply caring more than everyone else, we’ll be tough to beat.

What small change has made a big difference in your life?

I got a record player a few months ago. I went to a bar in Tokyo that was playing records, and the sound quality was mind-blowing. It kicked off this whole journey of understanding high fidelity recordings, and I thought it would be pretty cool to have in my apartment. Plus, I’ve been trying to be more intentional about how and when I use my phone; records solve that problem because I can still listen to music but don’t have to stay glued to my phone to control it. It’s a subtle shift, but it’s had a big impact on my day-to-day.

Now when I get home from work, putting on a record is usually the first thing I do. I’m also reading a lot more, because I don’t have my phone next to me. The timing and pacing is nice, because you have a built in break after 20 minutes or so to change sides. That brief period of time helps me switch gears. There are so many little things to do as a founder, and it’s important to make time to think creatively about the long term, not just the last six emails I read.

What don't you know that you wish you knew?

I’d love to be able to play an instrument. I think music is like poetry—it can take you to another place. There’s no way I’m ever going to invest the time it would take to learn, but I’m curious about what it would be like to not just listen, but play.

Instead, I learned to DJ. A friend taught me how, and I’m kind of an introvert, so it’s the perfect way to participate in a party. I play for friends’ birthdays and things like that, and it’s been really fun. My friend gave me a great tip, which was pick two or three people in the room that are kind of party-starters and DJ just for them. They’ll get everyone else on the dance floor.

What books are on your nightstand right now?

One I read recently was Honeybee Democracy, by Thomas Seeley, which is about how bees make decisions. It’s fascinating, and there are so many parallels to running a company. When bees choose a new nest, for example, they send a bunch of scouts to different locations and then the scouts report back by dancing. For a few days, there’s all this reporting and debating going on at once as they argue for different sites. But once the hive makes a decision, everyone stops dancing and is completely on board. There are lots of great lessons like that. My team has been making fun of me because I’ve added a bunch of bee facts to my slides for all-hands meetings.

One of my all-time favorite books is The Score Takes Care of Itself, by Bill Walsh, the former 49ers coach. I reread it a couple of times every year, and it’s such a great message: Care a lot about the little things, and the big things will follow. At Ironclad, that means being polite and friendly, sending the right follow-ups. I even saw someone fixing a wheel on our dishwasher the other day. All those things build up over time.

Another favorite is Joy: 100 Poems, which I can’t recommend enough. I think stepping into other people’s experiences is the best way to cultivate joy in your own life, because to feel joy you have to be completely in the moment. If you can start to recognize the moments where joy might occur, you’ll be more ready when it happens.

When did you realize you were wrong about something?

It took me a very long time to realize I would be a startup founder. Before Ironclad, I was an associate at a law firm. I worked with companies that were just starting to hire and fundraise, and the counselor part of the job was rewarding. But there was also a lot of busywork that took away from it. So I started experimenting with ways to take some of the paperwork off my plate, and for a long time, I assumed the solution was already in the market. I spent about two years investigating all the existing vendors and meeting with every legal tech startup that went through Y Combinator.

Eventually, I just started coding my own scripts and shared them with a few friends. One day, someone shared one of them back to me not knowing I created it, and I realized the tools I was building for myself had a much broader application. That’s when I came to terms with the fact that the problem probably wasn’t going to get fixed unless we did it ourselves.

What unit of time matters the most and why?

Our team is on a weekly cadence for just about everything. We decided to do weekly product releases really early on, and I think everything else flowed from there. We have an executive team meeting every Monday at 9 a.m. and then go to our weekly all-hands right after that. I also do weekly one-on-ones with my direct reports.

The nice thing about a week is it’s long enough to make real progress. We should be getting better every week. But it’s also short enough to be very iterative. It allows you to course-correct, tweak and experiment over time. And I think starting the week with everyone on the same page allows us to break out of the cycle of constantly responding, so we have a more proactive mindset.

Hard-won advice