Real Lawyers with Kevin O'Keefe

Kevin O’Keefe sits down with Kevin LaCroix of the D&O Diary to talk about nearly two decades of disciplined publishing in a narrow legal niche. LaCroix explains why he committed to writing four to five times a week, how consistency helped him build international credibility and why blogging sharpened his expertise more than any formal marketing effort. They also discuss authority versus visibi...

When Todd Smith launched one of Texas’ earliest appellate blogs in 2006 he wasn’t chasing traffic. He was building credibility as a young lawyer striking out on his own. In this conversation Todd joins Kevin to talk through the early days of legal blogging, how publishing shaped his reputation in a niche field and why he still sees blogs as a lawyer’s most durable online home. They get into the ch...

Kevin talks with Ohio employment lawyer Jon Hyman, author of the long-running Ohio Employer Law Blog. Jon shares how he started in 2007, how consistency shaped his reputation and why he keeps his writing conversational and authentic. They cover his “worst employer” series, his approach to daily posts and how AI now supports his workflow. A grounded look at how sharing what you know continues to op...

Kevin O’Keefe sits down with Nicole Black of 8am to trace how publishing and online connection reshaped her career. She explains how writing led to early opportunities, meaningful relationships in the legal tech community, her move into MyCase, and eventually her role at 8am. The conversation covers how lawyers can use consistent publishing to open doors, build trust and navigate toward the work t...

Kevin O’Keefe sits down with Alan Kaplinsky of Ballard Spahr, the lawyer behind the long-running Consumer Finance Monitor blog. Alan shares how the blog came together around the launch of the CFPB, how it evolved into a go-to resource in consumer financial services and how he has blended publishing with client work over the years. Kevin and Alan talk about what it takes to sustain a high-volume la...

Kevin sits down at ClioCon with A.J. Axelrod, head of Payments and Financial Services at Clio, to dig into how billing gets out of the way so lawyers can work. They cover fraud prevention inside payment operations and why faster cash flow matters for small firms. A.J. shares lessons from Visa, how recent acquisitions fit the platform and why Clio is focused on the unmet legal market. A straight sh...

Recorded at ClioCon, Kevin talks with Chris Stock, Clio’s VP of Legal Content and Migrations about his path from Australian law practice to legal tech, why Clio’s culture hooked him and how Clio Draft and AI workmates aim to speed everyday documents and expand access to counsel. Chris also shares his reentry work, thoughts on the latent legal market and how smarter automation can help lawyers serv...

Recorded live at ClioCon 2025 as part of LexBlog's coverage of the event (more to come!), Kevin talks with Clio CEO Jack Newton about seeing five years ahead and why the VLex deal makes the future of legal work feel inevitable. Jack shares how Clio grew from humble beginnings to a platform that can surface lawyer-authored insight where work happens, giving solos and small firms real thought-leader...

Kevin O’Keefe talks with Ed Walters — Fastcase co-founder and now Chief Strategy Officer at vLex — about why consistent writing still wins work in an AI era. Ed explains how blogs function as secondary law, how LexBlog content will surface inside vLex and why Vincent AI grounds answers in sources you can click and verify. He revisits his path from the White House to Fastcase, explains the vLex com...

Bob Ambrogi has been called a legend in legal journalism. He’s covered the profession for decades through print, blogging and podcasting and has been a fixture at ClioCon since its very first year. In this conversation with Kevin O’Keefe, Bob reflects on his career in legal media, why ClioCon feels different from other conferences and what to expect at ClioCon 2025 in Boston.

Stephen Rosenberg, one of the nation’s leading ERISA and insurance litigation attorneys and author of the Boston ERISA & Insurance Litigation Blog joins Kevin O’Keefe to talk about the role publishing has played in building his reputation and practice. They discuss how blogging helped him break into a closed market, why writing still matters more than metrics, how blogs can shape secondary law...

Matt DeVries, construction lawyer at Buchalter and longtime author of Best Practices Construction Law , joins Kevin O’Keefe to talk about how blogging shaped his career. Matt shares how writing helped him stand out in Nashville’s legal market, led to speaking at the AGC National Convention, and opened doors to national publications like Engineering News-Record . He also reflects on lessons from me...

Kevin talks with Cyndy McCollough, founder of McCollough Consulting, about moving legal marketing beyond AI experiments and into a shared roadmap. Cyndy explains why training first matters, how to pick one small pilot and measure it, and why a middle-out model beats top-down or bottoms-up alone. She shares practical wins—prompt libraries, email triage, event prep, competitive analysis and content...

From Mosaic and Usenet to one of the first immigration websites, Greg retraces securing his domain in 1993 and launching an email bulletin in mid-1994 that still runs today. He digs into early ABA advertising fights, daily site change logs and how that publishing drew calls from places like Cirque du Soleil. Greg explains why a Matthew Bender healthcare immigration book opened doors with Nashville...

Kevin O’Keefe sits down with Dan Harris, founder of the renowned China Law Blog, to talk about how a niche blog can transform a law practice. Dan shares the origin story of his pioneering legal blogs, why his firm requires lawyers to publish and how blogging has generated major clients in unexpected ways. They discuss lessons from launching the Cannabis Law Blog, the importance of consistency over...

Legal commentator David Lat joins host Kevin O’Keefe to chart his path from writing the irreverent, anonymous blog Underneath Their Robes to launching Above the Law in 2006 and now steering his reader-funded Substack, Original Jurisdiction . Lat explains how legal gossip and personality-driven stories grabbed attention inside a buttoned-up profession, why a subscription model for independent publi...

In this episode Kevin talks with Katie Wyka — Clio’s first in-house performance coach — about how to build resilient, high-functioning teams inside a fast-growing legal-tech company . Katie explains how her research on mental toughness informs her coaching approach and unpacks her “solo, doubles and team” framework for guiding individuals, pairs and whole groups toward peak performance. The conver...

Kevin talks with Carolyn Elefant — renewable‑energy litigator, MyShingle founder and leading voice for solo and small‑firm lawyers — about what it means to “own your talent” and build a sophisticated niche practice outside big law. Carolyn traces how her 2002 launch of MyShingle paved the way for democratized legal publishing and advocacy that challenges bar‑imposed barriers facing solos. She expl...

Kevin talks with Amy Shepherd—strategic advisor at Gladstone Growth Strategies and founder of Amy AI—about using artificial intelligence to streamline business development and modernise law-firm marketing. They cover lessons from scaling Ballard Spahr’s blog and podcast network, the role of lawyer champions, early survey data on AI adoption and why resilience still outperforms any new tool.

Davis Williams joins Kevin O’Keefe to talk about how law students can create their own opportunities through publishing, networking and exploring emerging areas of law. A rising 3L at North Carolina Central and founder of the International Legal Practice Society, Davis shares how he’s written about topics like digital personhood, AI and space law to connect with leaders and shape his career path....

Publishing in law is moving at AI speed. Kevin O’Keefe talks with Guy Alvarez—Founder & CEO of Alvarez AI Advisors and Good2BSocial before that—about using generative tools to fuel client-centric content, sharpen business development and carve profitable niches. They cover HubSpot’s early AI push, lessons from bootstrapping, a new survey on legal-industry adoption and why authority not keyword...

In this episode, Kevin talks with John Corey, co-founder of Green Target, about the evolution of legal marketing and the growing importance of thought leadership. They cover takeaways from the 2025 Marketing Report, the staying power of blogs and how AI is reshaping legal publishing. John highlights the need for actionable content and the chance for young lawyers to build authority through publish...