Kevin O’Keefe: The Visionary Blending Law and Technology

By Sophie Siadatpour

Before legal blogging was mainstream, Kevin O’Keefe saw its potential — and built an empire around it. From a start as a trial lawyer to becoming a pioneer in legal tech, his journey is a testament to the power of vision and perseverance. Today, O’Keefe is best known as the founder of LexBlog, a platform that has revolutionized legal blogging and transformed how lawyers connect with their audiences. His story, however, begins long before LexBlog, rooted in his days practicing law and discovering the untapped potential of the internet.

From Trial Lawyer to Legal Innovator

O’Keefe’s legal career started traditionally, as a plaintiff’s trial lawyer. Reflecting on those early days, when his knack for ambitious networking was first put to practice, he recounted: “I literally just knocked on doors to try to get a job. I would put on my suit and my wingtops and just show up, I didn’t have an appointment. And then I got offered two jobs after around three months.” After having worked in fields of law that didn’t match his long-term career goals, he took it upon himself to get into the courtroom and the world of litigation. His determination paid off, prompting him to take one lawyer and three staff in Wisconsin to build what became a very successful practice. As his professional career progressed, he noticed a growing need for better communication and networking tools for lawyers and their clients, sparking an idea that would change his life.

One minor unassuming moment opened a door of possibility in his mind, leading him to expand his career and improve his industry at large. The turning point came during a Packers game in the mid-90s when O’Keefe first encountered the internet. “I saw a little thing at the end of the game that said ‘www.toyota.com.’ I had no idea what it was,” he recalled. This curiosity led him to AOL message boards, where he began engaging with people on legal topics. “Next thing I knew, we had 30 or 40 of our own message boards with thousands of Q&As… That’s how my first company took off.”

Building Prairie Law and Its Acquisition

In 1999, O’Keefe launched Prairielaw.com, a community-driven platform for lawyers and consumers. He invited the country’s best lawyers from the top 70 cities, who he had developed connections with from his involvement in the bar associations across the country, to join the chatrooms and answer questions. This exchange started to build an ever-growing referral network between cases coming in off the internet and a national community of expert lawyers, a system that was essentially unheard of at the time. Prairielaw.com allowed people to have easy access to reliable and helpful legal advice in a more widespread way than probably ever before.

By combining content, discussion forums, and a mastermind group of lawyers, the platform quickly gained traction. Its success attracted the attention of LexisNexis, which acquired Prairielaw.com in 2001. The acquisition, although not especially lucrative, allowed O’Keefe to further develop his ability to identify and capitalize on emerging trends in legal tech, leading him to pursue what became one of his biggest career projects.

The Birth of LexBlog: Navigating Challenges and Driving Change

After his time with LexisNexis, O’Keefe set his sights on a new venture. Motivated to create a new platform by his own terms based on his ever-growing experience in the legal tech industry, O’Keefe, who moved to Seattle to found Prairielaw.com, worked tirelessly out of his garage until he formulated a more solid business idea and expanded his team. After he had discovered the art of blogging in fast-growing platforms like TypePad, which was just starting to expand in popularity and cultural relevance, O’Keefe found two books that evolved his discovery, one of which was Rebecca Blood’s Weblog Handbook, giving him more concrete professional insight on the innovative marketing method of blogging. This book sparked an idea about how blogging could be applicable to the legal industry, as it would allow lawyers to share their expertise online, in turn growing their client base. Inspired by his findings, he founded LexBlog in 2004 to help lawyers do just that. “I knew most lawyers would be afraid to blog without a professional support system and organization around them,” he explained. “So we created a platform tailored for them.”

“If you take a niche focus blog and write in a real and authentic way, you’ll get work.”

LexBlog started modestly, selling just three blogs in its first year. But O’Keefe’s vision paid off as the platform gained traction. Over time, LexBlog evolved into a comprehensive network, aggregating thousands of legal blogs and helping lawyers establish themselves as thought leaders. “If you take a niche focus blog and write in a real and authentic way, you’ll get work,” he said. “It doesn’t have to be a how-to guide… it starts as a conversation.” LexBlog grew to be mutually beneficial for both the lawyers, whose firms were gaining more credibility and attention, and the potential clients who got answers to their burning legal questions about their case and eventually being able to find the right legal services.

Building LexBlog wasn’t without its challenges. Early skepticism from the legal community was a significant hurdle. When LexBlog emerged on the scene, citizen journalism was still a new phenomenon that lacked widespread credibility, but it grew in commonality and began to be accepted as a valuable source of information on topics ranging from political conventions to case-specific legal advice. “When it started, as goofy as it sounds, people said, ‘Our firm will never do that. It’s not professional enough… it’s unethical,’” O’Keefe recalled. But over time, as concerns about firm confidentiality were debunked as blogs were more commonly used, they began to see the value in engaging authentically online.

Another challenge was the rapid evolution of technology. From managing servers in the early days to adapting to mobile and cloud-based solutions, LexBlog had to stay ahead of the curve. O’Keefe’s decision to build LexBlog on WordPress proved pivotal. “We have a really good, stable, secure, and highly performing platform that’s ours,” he said. The portal technology they’ve developed, combining the core WordPress base with custom plugins specifically built by LexBlog developers, takes publications from diverse sources and puts them all in one place for easy access, creating profile pages for the authors and the publications and organizations that they represent, ensuring reliability and scalability across all the site’s features.

A Vision for the Future

O’Keefe’s passion for legal blogging remains undiminished. He envisions a future where lawyers continue to leverage blogs to build reputations and foster meaningful connections. “A blog is a conversation,” he emphasized. “First, you listen. Then you provide your take just like you would at a networking event over a beer.”

He’s also committed to preserving legal blogs as a historical record. LexBlog’s Open Legal Blog Archive, which screens various legal blogs spanning different sites for value and relevance to the existing LexBlog content, now syndicates and houses over 800,000 posts from over 54,000 lawyers via an RSS feed, ensuring their wealth of knowledge isn’t lost. “If it is in fact advancing the law, then this is secondary law,” he said. “This is insight and commentary advice to explore.”

Over the past 21 years, LexBlog has drawn the attention of numerous plaintiff lawyers who have inquired about its functionality, purpose, and national reach. With its RSS connections to law school blogs across the country, O’Keefe not only answered their questions but also persuaded many to contribute, further expanding LexBlog’s growing network.

Kevin O’Keefe’s journey from a trial lawyer in Wisconsin to a trailblazer in legal tech is a story of curiosity, resilience, and innovation. Through LexBlog, he has empowered countless lawyers to share their voices and build their brands. As he reflects on his career, O’Keefe’s sentiments remain clear: Blogging isn’t just good for business; it’s good for its lasting effect on the legal industry as a whole.