The Renegade Lawyer Podcast

Ben Glass

I am more convinced than ever that nothing that traditional bar organizations are doing is going to move the needle on the sad stats on lawyer happiness ...The root cause of all lawyers' problems is financial stress. Financial stress holds you back from getting the right people on the bus, running the right systems, and being able to only do work for clients you want to work with. Financial stress keeps you in the office on nights and weekends, often doing work you hate for people you don't like, and doing that work alone.(Yes, you have permission to do only work you like doing and doing it with people you like working with.)The money stress is not because the lawyers are bad lawyers or bad people. In fact, most lawyers are good at the lawyering part and they are good people.The money stress is caused by the general lack of both business skills and an entrepreneurial mindset.Thus, good lawyers who are good people get caught up and slowed down in bringing their gifts to the world. Their families, teams, clients, and communities are not well-served because you can't serve others at your top level when you are constantly worrying about money.We can blame the law schools and the elites of the profession who are running bar organizations, but to blame anyone else for your own woes is a loser's game. It is, in itself, a restrictive, narrow, mindset that will keep you from ever seeing, let alone experiencing, a better future.Lawyers need to be in rooms with other entrepreneurs. They need to hang with people who won't tell you that your dreams are too big or that "they" or "the system "won't allow you to achieve them. They need to be in rooms where people will be in their ear telling them that their dreams are too small.Get in better rooms. That would be the first step.Second step, ignore every piece of advice any general organized bar is giving about how to make your firm or your life better.

  1. Ep. 207 – Renegade Lawyer Marketing (Audio Book) – Chapter 20: Get Better at Marketing Because It’s Your Duty

    4D AGO

    Ep. 207 – Renegade Lawyer Marketing (Audio Book) – Chapter 20: Get Better at Marketing Because It’s Your Duty

    In Chapter 20 of Renegade Lawyer Marketing, Ben makes a bold claim: Getting better at marketing isn’t optional. It’s your duty. If you are a good lawyer…  If you deliver quality service…  If you genuinely care about your clients… Then you owe it to the marketplace to make sure the right clients can find you. In this episode, Ben challenges the myth that “good lawyers shouldn’t have to market.” He explains why average marketing produces average results—and why doing what most lawyers do guarantees you’ll get what most lawyers get. Inside this chapter: Why solo and small firms can outmaneuver the 800-pound gorillasThe danger of copying “safe” and generic lawyer marketingWhy blind luck is not a business strategyHow ethical marketing actually serves clients betterThe uncomfortable truth about average resultsIf you believe you are the right lawyer for someone out there right now… this episode will challenge you to act like it. 🎧 Listen now on Apple Podcasts or Spotify 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.com What 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 mixing the 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.

    6 min
  2. Ep. 206 – Renegade Lawyer Marketing (Audio Book) – Chapter 19: What You Can Learn from My Mastermind Groups

    FEB 13

    Ep. 206 – Renegade Lawyer Marketing (Audio Book) – Chapter 19: What You Can Learn from My Mastermind Groups

    In this chapter of Renegade Lawyer Marketing, Ben pulls back the curtain on what actually happens inside Great Legal Marketing’s confidential mastermind groups. Spoiler alert: it’s not magic funnels, viral TikToks, or shiny new marketing hacks. It’s fundamentals. Executed relentlessly. Inside these closed-door sessions, successful solo and small firm lawyers from across the U.S. and Canada share what’s working—and what isn’t. And despite all the changes in media (Google, AI, YouTube, Instagram, TikTok, X…), the same truth keeps surfacing: The basics still win. In this episode, Ben breaks down the recurring principles behind thriving firms: Why most income still comes from referral systems—not adsThe surprising power of monthly print newsletters (yes, snail mail)Why refining what works beats chasing new shiny objectsThe real leak in the bucket (hint: it’s not your marketing budget)How mastermind members build marketing equity in-houseWhy “likes” don’t deposit at the bankIf you’re spending money on marketing but not obsessing over relationships, referrals, and conversion, this chapter may sting a little—in the best way. 🎧 Listen now on Apple Podcasts or Spotify 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.com What 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 mixing the 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.

    8 min
  3. Ep. 205 – Building a Tax Firm with Passion and Precision (with Pietro Canestrelli)

    FEB 11

    Ep. 205 – Building a Tax Firm with Passion and Precision (with Pietro Canestrelli)

    From the IRS to Entrepreneur: How One Lawyer Built a National Tax Practice Focused on People First Ben sits down with Pietro Canestrelli, a former IRS attorney turned boutique tax firm founder, to unpack how he built a thriving national practice with one clear mission: take the fear out of taxes. With a niche focus on tax controversy and strategic tax planning, Pietro’s firm now serves clients across the U.S. and beyond—growing from two employees to 20+ in under 10 years. He’s also the author of America’s Tax Defender, a story-driven look at his years inside the IRS and why he chose to walk away. 🔍 Inside this episode: How Pietro turned his IRS insider experience into a competitive advantageThe 3 tax domains every business owner should understandWhy passion and compassion guide every client interaction in his firmHow to market a niche practice by cultivating long-term referral partnershipsWhat solo and small firm owners are getting wrong about tax planningHis firm’s 3-stage hiring process—and how it keeps culture and client service aligned📘 Bonus: Check out Pietro’s book, America’s Tax Defender, available on Amazon. 🎧 Listen now on Apple Podcasts or Spotify 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.com What 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 mixing the 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.

    39 min
  4. Ep. 204 – The On-Fire Brain and the Future of Youth Sports

    FEB 3

    Ep. 204 – The On-Fire Brain and the Future of Youth Sports

    A Special Episode on Refereeing, Emotional Regulation, and Showing Up as the Sane Adult in the Room In this special edition of the Renegade Lawyer Podcast, Ben Glass steps away from case law and legal marketing—and dives into one of his biggest passions: youth soccer refereeing. Now in his 52nd year wearing the whistle, Ben shares a presentation he recently gave to high school soccer referees in Northern Virginia. But this talk isn’t about yellow cards or offside calls—it’s about brain science, emotional regulation, and why the real job of adults in youth sports is to protect the experience for kids. Drawing from decades of personal experience as both a referee and a parent of nine (including four children adopted from China), Ben opens up about how raising kids with early trauma taught him how to better handle on-fire brains—on the sidelines, the field, and at home. 🧠 Highlights: Why descent is a cancer on the game—and what referees can do about itWhat happens to the brain in moments of emotional escalationHow lessons from parenting trauma-impacted kids can transform your leadership on the fieldWhy every youth sports adult needs to adopt the mindset of "the sane adult in the room."“You don’t calm an on-fire brain with logic or threats. You calm it by being heard.” — Ben Glass📚 Bonus: Want to learn more about Ben’s adoption journey and how it reshaped his understanding of emotional regulation? 👉 https://youtu.be/ibJHocmHH-g?si=G5kGM3x8GTGyS9ud This one’s for: Referees in any sportParents of youth athletesCoaches and volunteersTeachers, mentors, and anyone in emotionally high-stakes environments🎧 Listen now on Apple Podcasts or Spotify 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.com What 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 mixing the 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.

    32 min
  5. JAN 28

    Ep. 203 – Behind the Case: How Ben Glass Built a Niche Long-Term Disability Practice (Iowa Law Guest Lecture)

    In this special recording of a guest lecture at the University of Iowa College of Law, Ben Glass gives students a rare behind-the-scenes look at how he built a national long-term disability (LTD) insurance practice—without relying on expensive digital ads. This episode is packed with real-world insight into: What the ERISA long-term disability space actually is—and why it’s underservedHow to build a multi-state legal niche that scales with systems, not billable hoursThe #1 marketing principle most lawyers ignore (but every business gets right)Why relationships, not algorithms, are Ben’s most profitable referral sourceThe difference between transactional advertising and true “authority marketing”💡 Highlights: Ben's approach to tribal leader marketing and storytelling to referral sourcesHow a single $2,500 sponsored blog post led to a high-end national pipelineThe 144-step internal process that doubles as a marketing magnetWhy he built an entire referral stream from doctors, lawyers, and financial plannersWhat to do when you’re brand new and don’t “have value” (hint: you do)Ben closes the conversation by giving advice to future law firm owners: think like a storyteller, find a niche that needs you, and never bet your future on one marketing tactic. 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.com What 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 mixing the 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.

    36 min
  6. Ep. 202 – Permission to Retire Toward Joy with Daya Naef

    JAN 7

    Ep. 202 – Permission to Retire Toward Joy with Daya Naef

    In this first episode of 2026, Ben sits down with attorney-turned-coach Daya Naef, founder of The Success Partner, for a future-focused conversation about what solo and small firm lawyers need to thrive in today’s landscape. Daya helps boutique firms (think 1 to 30 people) go from overwhelmed to optimized. Whether it’s succession planning, vision alignment, or AI implementation, she helps lawyers turn practices into platforms—and jobs into businesses. They talk: The trap of accidental entrepreneurship in lawWhy lawyers delay vision work—and how to fix thatHow AI is impacting real law firms right now (and where the fear still lives)How Ben is using internal GPTs to extract years of IP from his LTD playbookRetirement as a creative act—not just an exitIf you’re building a law firm that serves your life—or hoping to exit one with grace—this episode is full of energy, strategy, and practical ideas to get you moving. 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.com What 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 mixing the 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.

    38 min
  7. 12/18/2025

    Ep. 201 – Behind the Brief: ERISA Oral Argument in the 4th Circuit

    In this episode, Ben Glass shares a full oral argument recording from the U.S. Court of Appeals for the Fourth Circuit. The case? An ERISA long-term disability appeal involving a battle over regulatory deadlines, the standard of review, and the real meaning of "special circumstances." Ben argued on behalf of the plaintiff (appellee), after winning in the district court. Reliance Standard appealed. 🧠 Topics covered: How to frame ERISA deadlines and regulatory violations in federal courtThe real stakes of a standard-of-review battleWhat happens when insurers blow their timelines—but want to preserve discretionWhy most long-term disability appeals aren’t just about medical recordsThis episode is a rare look behind the curtain into the actual legal battlefield that ERISA litigators operate in—and how strategy plays out when you're standing before a panel of federal judges. If you take LTD cases—or refer them—this is essential listening. 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.com What 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 mixing the 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.

    57 min
  8. Ep. 200 – Behind the Summit: The Bigger Why of GLM Summit

    12/16/2025

    Ep. 200 – Behind the Summit: The Bigger Why of GLM Summit

    What’s really behind the Great Legal Marketing Summit? In this special episode, Ben Glass shares the bigger purpose of the work we all do—not just as lawyers, but as entrepreneurs, leaders, and humans trying to build lives that matter. 🔑 Key Ideas Explored: Why “permission” is the most important word for entrepreneursHow legal marketing connects people with the help they actually needWhy your job isn’t just running a law firm—it’s building a life that worksThe role our sponsors and partners play in this deeper missionThe new definition of success: doing work you love, with people you love, for clients you loveWhether you attended the GLM Summit or not, this episode is your reminder of what it means to lead a values-driven law practice. 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.com What 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 mixing the 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.

    8 min

About

I am more convinced than ever that nothing that traditional bar organizations are doing is going to move the needle on the sad stats on lawyer happiness ...The root cause of all lawyers' problems is financial stress. Financial stress holds you back from getting the right people on the bus, running the right systems, and being able to only do work for clients you want to work with. Financial stress keeps you in the office on nights and weekends, often doing work you hate for people you don't like, and doing that work alone.(Yes, you have permission to do only work you like doing and doing it with people you like working with.)The money stress is not because the lawyers are bad lawyers or bad people. In fact, most lawyers are good at the lawyering part and they are good people.The money stress is caused by the general lack of both business skills and an entrepreneurial mindset.Thus, good lawyers who are good people get caught up and slowed down in bringing their gifts to the world. Their families, teams, clients, and communities are not well-served because you can't serve others at your top level when you are constantly worrying about money.We can blame the law schools and the elites of the profession who are running bar organizations, but to blame anyone else for your own woes is a loser's game. It is, in itself, a restrictive, narrow, mindset that will keep you from ever seeing, let alone experiencing, a better future.Lawyers need to be in rooms with other entrepreneurs. They need to hang with people who won't tell you that your dreams are too big or that "they" or "the system "won't allow you to achieve them. They need to be in rooms where people will be in their ear telling them that their dreams are too small.Get in better rooms. That would be the first step.Second step, ignore every piece of advice any general organized bar is giving about how to make your firm or your life better.