The Renegade Lawyer Podcast

What happens when a seasoned entrepreneur with multiple 7-figure exits brings his playbook to the legal world?In this episode, Ben Glass sits down with Tim Sawyer, Executive VP of Sales at FasterOutcomes.com, to talk about how AI is transforming legal work—and what lawyers need to know right now.They cover:Why so many lawyers haven’t even opened the AI box—and what it’s costing themHow AI tools are already helping small firms reduce desk time, generate better demands, and serve more clientsWhat law firms can learn from elective medicine, insurance, and entrepreneurshipThe rise of AI-powered knowledge bases and playbooks to empower even junior associatesHow Faster Outcomes is partnering with elite lawyers like Rob Levine to systematize excellence in case outcomesThe “client-first” philosophy driving tech that’s accessible to solos, small firms, and enterprise teams alikeWhether you're curious about legal AI, looking to compete smarter, or just wondering what tools are worth your time, this is a must-listen conversation for forward-thinking lawyers.👉 Listen now on Apple Podcasts, Spotify, or wherever you tune in.Ben Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.

What if your most meaningful life lesson came from the bedside of the dying?In this powerful episode of the Renegade Lawyer Podcast, Ben Glass is joined by Dr. Jordan Grumet—hospice physician, author of The Purpose Code, and one of the most thoughtful voices at the intersection of medicine, meaning, and money.Together, they dive deep into:What Dr. Grumet learned about money and happiness from patients at the end of lifeWhy “finding purpose” might be the wrong goal—and what to do insteadThe art of subtraction—a practical framework for redesigning your life around what actually lights you upRetirement redefined: why it’s not about stopping work, but about building a life you don’t need to escape fromHis journey from burnout to a second career that includes hospice work, writing, podcasting, and financial educationWhether you’re a lawyer, doctor, or other professional wondering what’s next, this conversation is your reminder that you don’t have to wait for a crisis to start living intentionally.Dr. Grumet and Ben will both be speaking at the White Coat Investor Conference in March 2026—this episode is a preview worth sharing.Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.Ben Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.

In this episode of the Renegade Lawyer Podcast, host Ben Glass sits down with Dr. Andrew Roberts—retired internist, AI hobbyist, and public servant. From running for coroner in Indiana to mentoring small business owners with SCORE, Andrew’s “retirement” is anything but quiet.Ben and Andrew discuss:What it’s really like to run for coroner in a mid-sized county—and why it's a partisan electionThe practical (and surprising) ways AI is transforming medicine, from patient notes to billingThe crossover opportunities in AI for lawyers and doctors alikeWhy are both professions in an “AI arms race” with insurance companiesHow physicians and attorneys can reclaim time by building a “second brain”Tools for AI-driven vacation planning, product comparison, email triage, and moreAdditionally, Ben and Andrew discuss what it means to retire into something meaningful and how AI is creating space for more service, not just efficiency.Both Ben and Andrew will be speaking at the 2026 White Coat Investor Conference in Las Vegas.Ben Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.

In this episode, Ben Glass sits down with mindset and performance coach Kayleigh Kennedy, fresh off her visit to our in-person Hero Mastermind event.Kayleigh helps business owners—including lawyers—break free from burnout, reconnect with their purpose, and finally build a life that truly serves them. Together, she and Ben explore:Why most high-achieving professionals have no idea who they areThe power of giving yourself permission to rest, reset, and rethink the gameHow burnout creeps in—and what intentional recovery looks likeThe journaling techniques, nervous system rewiring, and small daily wins that create transformational changeWhy insights don’t happen at your desk—and what to do about itWhether you’re a lawyer chasing the next million-dollar case, or just someone who feels “off” and doesn’t know why—this conversation is your invitation to pause and realign.🧠 Learn more about Kayleigh at kayleighkennedy.com or find her on LinkedIn.Ben Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.

In Chapter 14 of Renegade Lawyer Marketing, Ben Glass flips the narrative on what it means to serve others as a lawyer. You’ll learn why “serving the client” isn’t about self-sacrifice—and why owning your power (and profit) is the first step to building a thriving practice and life.This chapter is a must-listen for any lawyer struggling with guilt around making money, turning away bad clients, or rejecting toxic industry norms. Ben shares:Why cash flow is your first obligation—not bar committees or bad clientsThe mindset shift that transformed his stress into strategic controlHow BB&T’s John Allison taught his team to think like ownersWhy lawyers must stop using “service” as an excuse to undercharge or overgiveThe moment Ben walked away from a salaried job—and faced the real stress of going soloA personal story of cash flow pressure, 9 kids, and bold decisionsIf you’ve ever felt conflicted about charging what you’re worth or saying no, this one’s for you.🗓️ Join Ben and hundreds of entrepreneurial lawyers at the next Great Legal Marketing Summit 📘 Grab the book or listen from the beginningBen Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.

In this special behind-the-scenes episode of the Renegade Lawyer Podcast, Ben Glass shares highlights from a private Hero Mastermind meeting at Ben Glass Law HQ. Get a front-row seat as Ben walks through real marketing experiments, referral strategies, direct mail systems, book-building using AI, and how he's making an impact (and leads) with referee scholarships and ProVisors.You'll learn:Why “networking” doesn’t work—and what to do insteadHow Ben uses personalized book mailings to build authorityWhat’s working in his LTD referral pipeline (including a $45M under-management strategy)A sneak peek at “The Investor Report” mailed to LTD referral partnersWhy authoring books is still shockingly effective in 2025The mindset behind price objections and curated follow-up sequencesHow he's using ChatGPT to draft entire books and letters (real examples included!)A powerful strategy for inspiring young referees—and generating buzz for Ben Glass LawThis one is packed with real strategies you can steal.Ben Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.

In this special episode, we’re sharing Ben Glass’s recent interview on The White Coat Investor Podcast, where he unpacks what every physician and high-income professional needs to know about disability insurance—before a claim, during the process, and if it’s ever denied.Ben covers:What makes a strong claim (and what insurers are really looking for)How to avoid common mistakes that derail benefitsThe truth about own-occupation policiesHow to plan strategically if you're facing a disabling diagnosis🎧 Originally aired on The White Coat Investor Podcast 🔗 Listen to the original episode here: WCI #427 – Dealing With a Disability ClaimHuge thanks to WCI for the opportunity to bring this conversation to a broader audience.Ben Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.

This is Chapter 13 of the free audio edition of Renegade Lawyer Marketing (Second Edition)—only on the Renegade Lawyer Podcast.It’s a short chapter with a powerful punch. Ben Glass shares the mindset shift that moves you from chasing clients… to having clients feel lucky to work with you.In this episode, you’ll learn:What to say when a client name-drops other lawyersWhy you shouldn’t always be the one pitchingThe difference between “needing a client” and “choosing a client”How to know when your marketing is working (spoiler: they don’t ask, “So what makes you different?”)This is about building a law firm that commands respect before the first phone call—even before the first click.Plus: Ben explains how his long-term disability practice grew a $750K recurring revenue stream by delivering insane client service.Mentioned:$45M in future benefit claims under management$750K/year recurring revenue (and growing)Exactly what makes a potential client “thunderstruck”To build a firm clients seek out—not stumble into—you need this chapter.Listen on Apple or Spotify Get the book + bonuses at RenegadeLawyerMarketing.com Join us live this October at GLMSummit.comBen Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.

This is Chapter 12 of the free audio edition of Renegade Lawyer Marketing (Second Edition)—only on the Renegade Lawyer Podcast.In this chapter, Ben Glass breaks down the real meaning of a Unique Selling Proposition (USP)—and why most law firm taglines completely miss the point.Forget clichés like “aggressive representation” or “we fight for you.” Your USP isn’t a slogan. It’s the reason someone chooses your firm over every other option, including doing nothing at all.You’ll learn:What your real USP is (and why it’s probably not what you think)How Coors Beer can teach you a killer marketing lessonWhy “we’ll make it drop-dead simple” is more powerful than “we’ll win big”How to explain your value in a way that matters to real clientsWhy your internal culture is just as important as your marketingShout-out: Thanks to our friends at Case Status, the #1 mobile client engagement tool for law firms—and a Premier Sponsor of the Great Legal Marketing Summit. Download their free 2025 Client Experience Report at casestatus.com📘 Get the book + bonuses at RenegadeLawyerMarketing.com 🎟️ Join us live this October at GLMSummit.comBen Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.

In this episode of the Renegade Lawyer Podcast, Ben Glass sits down with Gary Miles, a veteran lawyer, recovery advocate, and coach for attorneys seeking purpose and freedom in their practices.Gary is the host of The Free Lawyer Podcast and author of Breaking Free: A Guide to Achieving Personal and Professional Freedom as a Lawyer. He shares the mindset shifts, professional pivots, and life lessons that helped him leave insurance defense, build a thriving family law practice at 54, and now coach lawyers through burnout, imposter syndrome, and business growth challenges.You’ll hear:Why so many lawyers feel stuck—and how to break freeHow your law degree can open more doors than you thinkThe single most important business skill lawyers overlookWhat great coaching looks like (and how Gary supports his clients)Why mindset isn’t fluff—it’s the foundation of building a better practice📘 Get Gary’s book: Breaking Free: A Guide to Achieving Personal and Professional Freedom as a Lawyer 🎧 Listen to The Free Lawyer Podcast 🌐 Connect with Gary: garymiles.net | LinkedInBen Glass is a nationally recognized personal injury and long-term disability insurance attorney in Fairfax, VA. Since 2005, Ben Glass and Great Legal Marketing have been helping solo and small firm lawyers make more money, get more clients and still get home in time for dinner. We call this TheGLMTribe.comWhat Makes The GLM Tribe Special?In short, we are the only organization within the "business builder for lawyers" space that is led by two practicing lawyers. One thing we're sure you've noticed is that despite the variety of options within our space, no one else is mixingthe actual practice of law with business building in the way that we are.There are no other organizations who understand the highs and lows of running a small law firm and are engaged in talking to real clients. That is what sets GLM apart from every other organization, and it is why we have had loyal members that have been with us for two-decades.