Rule of Law

As AI transforms the legal profession and the pressure to work faster continues to grow, are lawyers losing sight of what makes them valuable in the first place?

In this episode, we're joined by Mike Whelan, Jr. of Lawyer Forward for a thought-provoking conversation about the future of law, the importance of critical thinking, and why slowing down might be exactly what the profession needs.

We explore how the economics of practicing law, the rising cost of legal education, and the push for greater efficiency are shaping the profession, and whether those pressures are pulling lawyers further away from their responsibility to serve the public good.

Mike also shares his perspective on what AI can't easily replicate: the ability to think deeply, recognize patterns, and draw connections. We discuss why those skills matter more than ever, how lawyers can make space for bigger-picture thinking, and why the profession has the power to challenge its own status quo.

Connect with Mike on LinkedIn and Substack.

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What does it take to build a business in an industry where getting the details right really matters? In this episode, we sit down with Frank Tumminello, CEO and co-founder of FileForms, to talk about his experience building and growing a company focused on business compliance.

We discuss the importance of getting state filings and compliance right, and what it means to operate in a high-stakes, high-trust business where clients depend on accuracy and reliability. Frank shares lessons from his entrepreneurial journey, how technology can help businesses manage increasingly complex compliance demands, and the importance of continuing to evolve as AI changes the way companies operate.

Interested in learning more about FileForms? Explore the platform or book a demo: Get started | Book a demo

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What makes work meaningful, and why doesn’t career success always lead to fulfillment?

Jeff Westphal knows that tension firsthand. After leading Vertex, a multibillion-dollar tax technology company, he turned his attention to understanding what gives people a sense of meaning at work and how individuals and organizations can create more of it.

In this episode, we dive into the difference between success and fulfillment, including why reaching the milestones we’ve spent years pursuing can still leave us feeling like something is missing. We also discuss the role employers can play in fostering meaningful work, and how AI and automation could reshape our relationship with work.

Check out Jeff’s new book: A Work Life Worth Living: Your Guide to Creating a Meaningful Career. Amazon.

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What does a cannabis attorney actually do? In this episode, we're joined by Andrew Cooper to discuss his unconventional path into cannabis and psychedelics law. Andrew shares why he left a more traditional legal practice, what it takes to build a career in an emerging industry, and why finding work you're passionate about can change the way you think about success. We also explore common misconceptions about the cannabis industry, the evolving regulatory landscape, and where cannabis policy may be headed next.

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Drew Jacobs, founder of Jacobs Counsel, joins the podcast to discuss building an AI-native law firm, and representing clients in the sports, entertainment, gaming, and tech industries. We explore how AI is changing legal practice, where it adds value (and where it doesn't), the realities of serving entrepreneurs, and what the future of small law firms looks like in an increasingly technology-driven profession.

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Law firms lose massive amounts of revenue through poor billing habits, inconsistent time tracking, and mindset issues lawyers often don’t even realize they have. In this episode, Molly Kremer, “The Billing Coach,” breaks down the biggest billing mistakes attorneys make, the “time burglars” stealing billable hours, and practical ways to improve billing consistency.

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In this episode, Phoebe Morris joins us to discuss the evolution of legal services in the age of the creative economy. Phoebe shares how she’s moved beyond traditional hourly billing to offer creators, startups, and small businesses a more modern, accessible approach to legal services. We dive into what alternative legal services look like for startups and creators, how alternative fee structures can create better outcomes for both lawyers and clients, and what the future of legal services might look like.

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In this episode, we sat down with RJon Robins, founder of How to Manage a Small Law Firm, to break down what it really takes to build a successful law practice. Spoiler alert! It is NOT giving up your life. We explore how to define success beyond revenue, the difference between working in your business versus on it, and why that shift is critical for long-term growth. This episode is packed with practical insights for attorneys looking to run a more strategic, scalable firm.

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In this episode, we sit down with a leading voice in AI and legal tech - Colin Levy. We explore what lawyers should really be asking about artificial intelligence, and the mindset shift law firms need to make - from updating outdated workflows to rethinking how legal work is done. We also discuss why so many tech initiatives fail and how the next generation of lawyers is approaching AI.

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In this episode, we dig into how the business of law is changing as outside investment, alternative legal service providers, and management services organizations become a bigger part of the conversation. We unpack the recent headlines around non-lawyer ownership and look ahead at what all of this means for the future of law firm structures.

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