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 serve real people faster.
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-leadership reach. They hit on building a company while raising a family, the team behind the keynote, and why approachable leadership on social matters. Plus, the long-running ClioCon morning run tradition. A candid look at vision, execution and the human side of a transformational year for Clio.
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 combination and shares what makes ClioCon different plus Jack Newton’s role as a visionary leader. A candid conversation about expertise, relationships and publishing with purpose.
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 and why young lawyers should use publishing to carve out niches even in the age of AI.
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 mentors, balancing personal challenges with professional growth, and why niche focus and authentic storytelling still matter in an AI-driven era.
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 strategy—that free teams to do higher-value work, drawing on a career that spans Microsoft and Oracle to leading BD in major firms. If you run marketing or BD and need a clear starting point, this conversation gives you the playbook.
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 hospital systems, how sports and universities followed, and what being visible to AI now means for lawyers. Practical takeaways: pick a specific niche, write relentlessly, think beyond SEO so ChatGPT can find you.
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 quick wins and why blogging remains a powerful tool for young lawyers to break into competitive markets.
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 publishing builds a healthier bond with readers than ad-driven media, and what value-add commentary lawyers need to stay ahead of AI-generated summaries of the news.
Whether you want to monetize a niche newsletter, revive your blog or just hear insider courthouse stories, this candid conversation delivers fresh insight on legal gossip, media entrepreneurship and independent publishing.
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 conversation explores balancing a human workplace with ambitious growth targets, spotting early signs of team dysfunction and creating confidential spaces where people can experiment and improve. Listeners will leave with practical strategies they can apply to any size firm to strengthen collaboration, resilience and results.
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 explains why generative AI has reignited her passion for practice, showcases her “AI teach‑in” model and shares practical ideas for solos to leverage deep‑research tools to win work faster. The conversation also touches on personal resilience, community building and Carolyn’s vision for a nationwide network of solo publishers.
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. They discuss taking initiative, thinking globally and how young lawyers can build influence early.
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 keywords will drive search in the LLM era.
00:48 – How Guy got started
03:25 – Early lessons in bootstrapping a legal marketing agency
08:42 – Why niche focus gives firms a competitive edge
12:30 – The role of AI in legal marketing today
18:55 – Jasper, Gemini, and other AI tools Guy uses
23:10 – Challenges firms face adopting AI
27:45 – Client-centric content vs. firm-centric content
32:15 – Law firm culture and marketing innovation
36:00 – Advice for younger lawyers and marketers
39:40 – The future of AI and trust in legal services
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 publishing. The conversation underscores how legal marketing is changing and why strong communication strategies matter more than ever.
