Real Lawyers with Kevin O'Keefe

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.

Cyndy McCollough, founder of McCollough Consulting and expert in AI roadmaps for law firms, shares her insights on integrating technology into legal marketing. She emphasizes the importance of starting small with AI pilots to build comfort and measure success. Cyndy advocates for a middle-out approach to foster collaboration, contrasting it with traditional models. She provides practical tips on tools like prompt libraries and email triage, enabling teams to focus on high-value work, drawing on her rich experience from the tech giants Microsoft and Oracle.

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.