On the Whiteness and Bro-ness in Legal Tech/Innovation

No, this piece isn’t depressing. Promise.

We know there’s a diversity problem in tech. We know there’s a diversity problem in legal. Put them together and you get diversity problem squared. But I think there’s reason to feel good about the road ahead.

Last week, I was in Chicago for Bill Henderson’s event, the Forum on Legal Evolution. Bill is a great and very smart guy and the event was lovely. The highlight for me was being able to roast the amazing Mark Chandler, who received a much-deserved lifetime achievement award at the event along with his co-conspirator Paul Lippe.

Those of you who know me are probably alarmed that someone gave me a microphone to do a roast. It remains to be seen if Mark will ever speak to me again, but I got a few solid laughs and even more wtf looks … so, success?

I digress. I started out my roast by joking about out how white and male the room was, captured nicely by Jordan Couch on twitter:

This portion of my roast is what people commented most about afterwards, in a “so true” kind of way. (To be very clear, this is not a knock on Bill, who I know values diversity immensely, or the event, which featured some primo female speakers). But all of this made me realize something, and I think it’s a good thing.

The Legal Tech/Innovation Waves

The event was to honor Mark and Paul. Without making any more old jokes beyond what was in my roast, Mark and Paul really represent the first generation of modern legal innovators. They were trailblazers, and in the early days they were surrounded by a pretty homogenous and very small group of other trailblazers. There were certainly some women doing groundbreaking work in that wave, including women who have helped me on my way (think Susan Hackett, Betsy Munnell), but not many.

What I realized is that I fit in to the second wave of people trying to make substantial change in this industry. This second wave feels much more diverse than the first wave, which makes a whole lot of sense.

In looking back on my interactions with people in the industry, I realize that I’ve always felt slightly uncomfortable being myself around the first generation, but I have absolutely no problems letting it all hang out with the second generation. Early on in my career, I got some distinct “awww, isn’t it cute, a girl doing a thing” vibes from the first generation — not the Marks and Bills of the world for sure, but it was there. I feel none of that from my generation. Maybe it’s just an age/experience differential, or maybe it’s not. But being able to “be myself” is more significant than it seems. It’s allowed me to take more risks and make more of an impact than I would if I felt like I had to play some role that was expected of me. Multiply this effect across all the other women in the space, and the benefits to the industry are huge.

There’s now a third wave coming up, and they’re exciting to watch. There are some badass women making some great products, like my homegirls at Paladin. There are rising stars all around. Before going to Chicago last week, I spoke to David Colarusso’s “Coding the Law” class at Suffolk University Law School. The class appeared to be majority female and the women were the more active and engaged participants, which leaves me feeling very excited for the next generation.

My point in all of this: It’s easy to make fun of the white bro-ness of legal tech and innovation, especially after a couple of glasses of wine during a roast, but I think we have very good reason to feel optimistic about the state of diversity in our small corner of a massive industry. Importantly, there’s the second wave of women like me, like Jules Miller, and many others who have reached a level of success where we now can and want to reach down and help others up.

So, to the next wave: If you’re starting up a legal tech company, or are thinking about starting one, or are just generally interested in this space, send me an email. My door is open, and I’ll always take the time. So will many of my peers.

And to the first wave, thank you for all you’ve done to help support me and my peers on this journey.