The Lawyer Stories Podcast

Benjamin Gold
  • 5.0 (519)
  • Society & Culture
  • Updated Weekly

First founded on Instagram in July 2017, (@lawyer_stories,) the Lawyer Stories Podcast discusses lawyers and law students journeys to the practice of law.

  1. 2d ago

    Ep 286 | Mark Milton | From Representing the IRS to Fighting for Taxpayers

    What happens when the lawyer who once represented the IRS switches sides? On Episode 286 of The Lawyer Stories Podcast with Benny Gold, we head to St. Louis, Missouri, for a conversation with Mark C. Milton, Founder and Managing Attorney of Milton Law Group - a tax attorney whose career has taken him from public accounting, to the U.S. Department of Justice Tax Division, to BigLaw, and ultimately to building his own firm. Milton Law Group Mark began his legal career as a DOJ Tax Division Trial Attorney, where he represented the United States in collection matters, refund suits, and complex federal tax litigation across the country. He later practiced at an AmLaw 100 firm in St. Louis handling tax controversies, white-collar matters, investigations, and business litigation before launching Milton Law Group in 2017. Milton Law Group We talk about what Mark learned from being on the government's side of the table, why taxpayers shouldn't automatically assume the IRS is simply out to get them, and his perspective that the government generally wants taxpayers to get back into compliance and resolve their tax problems. We also get into Mark's entrepreneurial journey and the Summer Tax Summit, the St. Louis event he chairs that brings together tax controversy attorneys, IRS and IRS Criminal Investigation officials, federal judges, and other leaders in the tax world - with some uniquely St. Louis experiences mixed in. Milton Law Group From accounting to the DOJ, BigLaw, tax controversy, white-collar work, entrepreneurship, and building a nationally focused practice from St. Louis - Mark has one heck of a Lawyer Story. 🎙️ Episode 286 is available now! Listen and follow The Lawyer Stories Podcast on Apple Podcasts and Spotify. This episode is presented by CallRail. Integrated into your case management system, CallRail helps law firms capture every call—even after hours, spot high-value leads instantly, respond faster, and get the insights needed to bring in bigger cases. Join over 3,000 law firms using CallRail to follow up faster, land bigger cases, and drive growth for your firm. Start your free trial: https://www.callrail.com/legal-services?utm_medium=influencer&utm_source=lawyer-stories

  2. Sep 25

    Ep 285 | William McCreight of BluShark Digital | SEO, AI Search & the Future of Legal Marketing

    How will clients find your law firm in the age of AI? On Episode 285 of The Lawyer Stories Podcast with Benny Gold, we sit down with William McCreight of BluShark Digital and host of the Legal Currents Podcast to discuss the rapidly changing world of legal marketing, SEO, and AI-powered search. William shares his journey into the legal marketing space, what law firms need to understand about building visibility online, and how platforms like Google and emerging AI tools are changing the way potential clients search for lawyers. We also discuss the evolution of SEO, the rise of AI-generated answers, how consumers are using AI to research legal issues, what firms should be doing now to prepare for the next generation of search, and where William sees legal marketing headed next. This episode is presented by Supio, an AI-first platform purpose-built for plaintiff law. Supio helps law firms leverage AI across the entire case lifecycle - from intake through litigation - giving attorneys more time to focus on their clients and their cases. Through its collaboration with Thomson Reuters' Westlaw, Supio is bringing trusted legal research together with AI-powered case intelligence. Learn more at supio.com/lawyerstories. 🎙️ Episode 285 is available now! Listen and subscribe to The Lawyer Stories Podcast on your favorite podcast platform. Learn more about Supio: http://supio.com/lawyerstories

  3. Sep 18

    Ep 284 | Jason DeSouza | Building a Personal Injury Law Firm & Fighting for the Underserved

    When your client is going through the worst moment of their life, being their lawyer sometimes means doing more than practicing law. On Episode 284 of The Lawyer Stories Podcast with Benny Gold, we sit down with Jason DeSouza, Founder and Lead Trial Attorney at DeSouza Injury Lawyers in San Antonio, Texas, to talk about his journey from Toronto to Texas, discovering his calling in the courtroom, and building a personal injury firm from the ground up. Jason started his firm in 2015 with just himself and a paralegal. Today, he leads a team of roughly 30 representing people in serious injury, trucking, oilfield, and catastrophic injury cases throughout Texas. But Jason's story is really about people. His blue-collar upbringing shaped the way he represents clients and his commitment to communities that larger firms can sometimes overlook. At one point, that commitment even meant lending his own car to a client who needed help. We talk about scaling a law firm without losing the personal connection, becoming a better trial lawyer, standing up to corporations and insurance companies, leadership, and why Jason believes a person's life can never simply be reduced to a number on a spreadsheet. 🎙️ Episode 284 is available now! Listen and subscribe to The Lawyer Stories Podcast on your favorite podcast platform. 🗽 Lawyer Stories is headed to REVCON 2026! Join us September 29 in New York City for Morgan & Morgan's REVCON 2026: Operational Anatomy of a Record-Breaking Year, a one-day, CLE-accredited event featuring leaders in marketing, management, technology, litigation, and AI. 🎟️ Lawyer Stories listeners save 20% with code STORIES20. Register for REVCON 2026 This episode is presented by CallRail. Integrated into your case management system, CallRail helps law firms capture every call, respond faster, spot high-value leads instantly, and drive growth. Join over 3,000 law firms using CallRail to follow up faster, land bigger cases, and grow smarter. Start your free trial: https://www.callrail.com/legal-services?utm_medium=influencer&utm_source=lawyer-stories

  4. Sep 10

    Ep 283 | Jennifer Chapkin | The Lawyer Who Saw a Gap in Estate Planning & Built Safe and Signed™

    She saw a problem in estate planning. So she built the solution. On the latest episode of The Lawyer Stories Podcast, Benny Gold sits down with Jennifer Chapkin, Esq., estate planning attorney and Co-Founder & CEO of Safe and Signed™, to talk about her Lawyer Story, entrepreneurship, and turning a problem she repeatedly encountered in her legal practice into a business. Jennifer loves being part of people's big moments - helping families and business owners make consequential decisions about their lives, property, businesses, and futures. But after years of practicing estate planning law, she kept seeing the same issue: after wills, trusts, powers of attorney, healthcare directives and other important legal documents were signed, where would the originals actually go — and would the right people be able to find them years later when they were needed? That problem inspired Safe and Signed™, a professional custody service for signed original estate planning and other important legal documents. Originals are protected in an access-controlled, fire-safe, water-safe and climate-controlled facility, while authorized parties can securely access document information and scanned copies. Jennifer shares the moment the idea took hold, what it was like building a company in a category that didn't really exist, balancing entrepreneurship with practicing law, and what she has learned about taking an idea beyond the traditional law firm model. 🎙️ Listen and subscribe to The Lawyer Stories Podcast on your favorite podcast platform. This episode is presented by CallRail. CallRail helps law firms understand which marketing efforts are driving their best leads, capture every call, improve intake, and respond faster. And now, CallRail integrates with Clio, connecting marketing and intake insights with the tools firms already use to manage their clients and cases. Start your free trial with CallRail 🗽 Lawyer Stories is headed to REVCON 2026! Join us September 29 in New York City for Morgan & Morgan's REVCON 2026: Operational Anatomy of a Record-Breaking Year, a one-day, CLE-accredited event bringing together leaders in marketing, management, technology, AI, and litigation to help build the modern plaintiff law firm. Lawyer Stories listeners save 20% with code STORIES20. Register for REVCON 2026

  5. Sep 2

    Ep 282 | Rob Martorana | AI, Litigation Intelligence & the Future of Legal Tech

    AI is changing litigation - but is the defense bar keeping pace? On Episode 282 of The Lawyer Stories Podcast, Benny Gold sits down with Rob Martorana, Head of Partnerships at Theo Ai, for a fascinating conversation about artificial intelligence, litigation intelligence, case strategy, and the future of legal technology. Rob brings a unique perspective to the conversation. His career has taken him from serving as an Assistant District Attorney and practicing law to years in litigation finance and now the rapidly evolving world of legal AI. We discuss the technology and investment gap between the plaintiff and defense bars, why defense litigation has historically been difficult to standardize, and how AI can help legal teams better understand massive amounts of litigation data. Rob also shares his perspective on case valuation, settlement benchmarking, litigation finance, risk and exposure analysis, and how technology may change the way lawyers evaluate and manage cases. 🎙️ Episode 282 is available now! Listen and subscribe to The Lawyer Stories Podcast on your favorite podcast platform. Thank you to our partner CallRail, helping law firms understand which marketing efforts drive their best leads, improve intake, and turn more opportunities into clients. CallRail is now integrated with Clio, connecting marketing and intake insights with the tools firms use to manage their clients and cases.  Contact Benny for more info or start your free trial: https://www.callrail.com/legal-services?utm_medium=influencer&utm_source=lawyer-stories 🏙️ Lawyer Stories is headed to REVCON NYC! Join us September 29 at the Perelman Performing Arts Center in New York City for Morgan & Morgan's REVCON 2026, where Lawyer Stories will be on-site podcasting and capturing conversations with leaders across the legal industry. Use code STORIES20 to save 20% on your REVCON ticket.

  6. Aug 26

    Ep. 281 | Lawyer Stories LIVE from AAJ Chicago with Supio: Trial Lawyers, AI & the Future of Plaintiff Law

    🎙️ Eight conversations. One special episode. Lawyer Stories LIVE from AAJ in Chicago. For our first trip to the American Association for Justice (AAJ) Annual Convention, Lawyer Stories sat down with trial lawyers, legal leaders and innovators for conversations about the journeys that shaped them, advocacy, trial practice, building modern law firms, technology, AI and where the profession is headed. We love taking Lawyer Stories on the road. There's something special about sitting down face-to-face, meeting people where they are, and capturing these conversations in the middle of the energy of a major legal event. Featuring: ⚖️ Chad Mance — The Mance Law Firm ⚖️ Jamie Beck — Founder & CEO, Justice with Humanity ⚖️ Mo Hamoudi & Karen Koehler — Stritmatter Law ⚖️ Rilee Harrison — Maples Harrison Zeaman PLLC ⚖️ Niki Hall — Chief Market Officer, Supio ⚖️ Paul Miller — Howie, Sacks & Henry LLP ⚖️ Al Foeckler — Cannon & Dunphy, S.C. ⚖️ Bryan Pope — The Cochran Firm A huge thank you to Supio for partnering with Lawyer Stories to make our AAJ coverage possible. Supio is building agentic AI purpose-built for plaintiff law, supporting firms across the case lifecycle. Its collaboration with Thomson Reuters connects Supio's case intelligence with Westlaw Advantage, helping attorneys move from case facts to authoritative legal research and validation in a more connected workflow. Lawyer Stories LIVE from Chicago. 🎙️ 🎧 Episode 281 of The Lawyer Stories Podcast is out now. Listen on your favorite podcast platform.

  7. Aug 19

    Ep 280 | Steven Gursten | Trial Advocacy, Trucking Litigation & Record-Setting Auto Accident Results

    What separates a good trial lawyer from a great one? The Lawyer Stories Podcast Episode 280 features Steven Gursten of Michigan Auto Law, nationally recognized trial attorney, author, speaker, and leader in auto accident, trucking, traumatic brain injury, and No-Fault insurance litigation. Steve has recovered some of the largest reported auto and truck accident settlements and verdicts in Michigan and has been recognized as a Lawyer of the Year and consistently among the state's top attorneys. In this episode, we discuss Steve's journey as a trial lawyer, what it takes to successfully litigate serious injury and trucking cases, trial preparation and advocacy, and the responsibility plaintiff lawyers have to their clients. We also talk about his work helping make the trucking industry and our roads safer, his leadership within AAJ, the growing role of AI in the legal profession and what it could mean for lawyers and their practices, and what Steve has learned teaching trial lawyers across the country. Steve also recently received the Gary Pillersdorf Courage Award from the Belli Society, adding another chapter to an incredible career advocating for injured people. 🎙️ Watch or listen to Episode 280 of The Lawyer Stories Podcast with Benny Gold on your favorite podcast platform. This episode is presented by Supio. As an AI-first company purpose-built for plaintiff law, Supio is helping firms leverage AI across the entire case lifecycle—from intake through litigation—so attorneys can spend more time advocating for their clients. Their collaboration with Thomson Reuters' Westlaw is another exciting step toward bringing trusted legal research together with AI-powered case intelligence. Learn more about Supio: http://supio.com/lawyerstories

  8. Aug 13

    Ep 279 | Sydney Segal | From CBS Survivor to the Courtroom: Life as a Public Defender

    What do the courtroom and Survivor have in common? More than you might think. The Lawyer Stories Podcast Episode 279 features Sydney Segal, public defender, former Division I athlete, and competitor on CBS Survivor 41 and MTV's The Challenge. Sydney's Lawyer Story is anything but conventional. From competing as a Division I runner at Columbia University to law school, reality television, and ultimately becoming a public defender, Sydney has built a life around competition, advocacy, and standing up for what she believes in. At the center of her legal career is a strong belief in due process, the presumption of innocence, and the fundamental goodness of people. We discuss why she chose public defense and what it means to advocate for people during some of the most difficult moments of their lives. We also talk about an innovative initiative Sydney helped create while working in Los Angeles after recognizing that some criminal defendants were missing court simply because they lacked reliable transportation. Sydney worked to establish a program with Uber providing ride vouchers to help defendants get to court—a creative solution designed to prevent a transportation problem from becoming another reason for someone to end up back in jail. Sydney also shares how growing up with a lawyer for a father influenced her path, and how the competitiveness and resilience she developed as an athlete—and later tested on Survivor and The Challenge—show up in her work as a lawyer today. Survivor. The Challenge. The courtroom. One incredible Lawyer Story. 🎙️ Watch or listen to Episode 279 of The Lawyer Stories Podcast with Benny Gold on your favorite podcast platform. This episode is presented by CallRail. Integrated into your case management system, CallRail helps law firms capture every call—even after hours, spot high-value leads instantly, respond faster, and get the insights needed to bring in bigger cases. Join over 3,000 law firms using CallRail to follow up faster, land bigger cases, and drive growth for your firm. Start your free trial: https://www.callrail.com/legal-services?utm_medium=influencer&utm_source=lawyer-stories Join us at REVCON 2026. If you've heard of RevCon before, this is the next revolution. Hosted by Dan Morgan, Operational Anatomy of a Record-Breaking Year is a one-day, CLE-accredited event bringing together experts in marketing, management, technology, AI, and litigation to help build the modern plaintiff law firm. 📍 September 29, 2026 📍 New York City Walk away with practical, AI-first and cross-functional strategies you can implement immediately at your firm. Lawyer Stories listeners save 20% with code STORIES20. Register here: https://events.themorganconnection.com/revcon2026/lawyerstories

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5
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519 Ratings

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First founded on Instagram in July 2017, (@lawyer_stories,) the Lawyer Stories Podcast discusses lawyers and law students journeys to the practice of law.

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