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Legal Geek North America Conference: Innovation in Jeans and Birkenstocks

By Kevin O'Keefe on June 2, 2025
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I’m thinking of heading back to Chicago in a couple of weeks for Legal Geek North America—a one-day conference on Tuesday, June 17. I’d make a week of it to meet with clients and partners.

Legal Geek has its roots in London, where I first attended back in 2018. Unlike legal conferences in hotels and convention centers, Recess, the site of Legal Geek North America is an indoor-outdoor space in the West Loop that is more creative agency than corporate. It’s billed as “a playground for grown-ups.”

Glib, but well described for the small plywood stands for exhibitors, low stages and beer next door, afterwards, that I experienced in London. 

The format is brief TED-style talks and roundtables. With an impressive group of over forty authorities, the vast majority of the sessions are dedicated to AI. 

Working in legal publishing, what stood out to me on the agenda was the inward focus of AI—how to streamline, cut costs, and do more with less. What’s missing is an outward look: how an understanding of AI can be used to grow a law firm’s business, not just run it more efficiently.

For law firms, the terrain of business development is profoundly changing. Authority and expertise, the foundation of growing business, is being established by open-source and closed-corpus LLMs alike. Law firm marketing strategy will never be the same.

That said, Legal Geek isn’t built for deep dives into business development through AI—that’s a different kind of conference. But if you’re in or near Chicago, it remains one of the more energizing and inspiring events in legal tech.

The people who gather there—startups, innovators, in-house teams, firm leaders are fun to meet and talk with. 

Alicia Hawley of K&L Gates may put it better, “Legal Geek allows a casual and collaborative space to connect with industry professionals and expand your knowledge base.”

Photo of Kevin O'Keefe Kevin O'Keefe

I am a trial lawyer, turned legal tech entrepreneur, now leading the largest community of legal publishers in the world at LexBlog, Inc.

I am a lawyer of 39 years. Wanting to be a lawyer since I was a kid, I have loved…

I am a trial lawyer, turned legal tech entrepreneur, now leading the largest community of legal publishers in the world at LexBlog, Inc.

I am a lawyer of 39 years. Wanting to be a lawyer since I was a kid, I have loved almost every minute of it.

I practiced as a trial lawyer in rural Wisconsin for 17 years, representing plaintiffs, whether they were injury victims and their family members or small businesses.

In the mid-nineties, I discovered the Internet in the form of AOL. I began helping people by answering questions on AOL message boards and leading AOL’s legal community.

I later started my own listservs and message boards to help people on personal injury, medical malpractice, workers compensation and plaintiff’s employment law matters. Though we were green to technology and the Internet, USA Today said if my firm “didn’t stop what we were doing, we would give lawyers a good name.”

In 1999, I closed my law firm and we moved, as a family of seven, to Seattle to start my first company. Prairielaw.com was a virtual law community of people helping people, a sort of AOL on the law, featuring message boards, articles, chats, listervs and ask-a-lawyer.

Prairielaw.com was sold to LexisNexis, where it was incorporated into Martindale-Hubbell’s lawyers.com.

After a stint as VP of Business Development at LexisNexis, I founded LexBlog out of my garage in 2004 (no affiliation with LexisNexis).

Knowing lawyers get their best work from relationships and a strong word of mouth reputation, and not promoting themselves, I saw blogging as a perfect way for lawyers to build relationships and a reputation.

When I could not find someone to help me with my own blog, I started a company to provide what I needed. Strategy, professional design, platform, coaching, SEO, marketing and free ongoing support.

As a result of the outstanding work of my team of twenty and my blogging, the LexBlog community has grown to a community of over 30,000 legal professionals, world-wide.

Publishing my blog, Real Lawyers, now in its 18th year, I share information, news, and commentary to help legal professionals looking to network online, whether it be via blogging or other social media.

Blogging also enables me to think through my ideas – out loud and in an engaging fashion.

In addition to my blog, I liberally share others’ insight on Twitter. Feel free to engage me there as well on LinkedIn and Facebook.

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