Real Lawyers with Kevin O'Keefe

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 started03:25 – Early lessons in bootstrapping a legal marketing agency08:42 – Why niche focus gives firms a competitive edge12:30 – The role of AI in legal marketing today18:55 – Jasper, Gemini, and other AI tools Guy uses23:10 – Challenges firms face adopting AI27:45 – Client-centric content vs. firm-centric content32:15 – Law firm culture and marketing innovation36:00 – Advice for younger lawyers and marketers39:40 – 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.