Welcome to a new season of Matters, a podcast about exploring the intersection of law, technology, and the business of running a successful firm. Hosted by Clio's CEO & Founder, Jack Newton.

In this conversation, we sit down with Bob Ambrogi, the "Walt Mossberg of legal", to unpack the moments that changed law forever—from the first web browser to the AI revolution. We reveal why solo firms are out-innovating Big Law, the truth about private equity's grip on software, and the one skill lawyers need to survive the next decade. 

In this conversation, we explore:

• The prescient early days: How Bob predicted the web would change marketing and research for lawyers back in 1995.
• The cloud shift: Why Clio’s 2008 launch served as a pivotal moment for cloud-based practice management.
• Industry consolidation: The pros and cons of private equity firms rolling up independent legaltech brands.
• The future of work: Why AI will lead to more lawyers, not fewer, by addressing the massive "Access to Justice" crisis.

Bob Simon, Founder of Justice Team, is challenging the status quo in the personal injury and legaltech space. Through a disruptive approach to firm culture and the creation of Justice HQ, a tech-forward platform designed as an incubator for innovation, he is reshaping how law firms think about competition, collaboration, and community.

A seasoned trial lawyer, Bob transitioned from a traditional “name-on-the-door” practice to building the Justice Team brand, reimagining the modern lawyer’s journey in the process. He combines high-level trial advocacy with a virtual-first operating model that values authenticity and impact over conventional prestige.

In this conversation, we explore:

• How empowerment outperforms control: Why giving lawyers a platform to shine (and even move on) creates a stronger network than hoarding talent.
• The modern tech stack: How to use AI for mailroom automation, CRM for lead tracking, and social media for "grassroots" marketing.
• Trial tactics for the future: A look at virtual trials, VR in the courtroom, and the human element of storytelling.

Jacqueline Schafer, the Founder and CEO of Clearbrief, and Damien Riehl, Solutions Champion at Clio, are reshaping the legal industry by moving AI beyond the "hype phase" into practical, daily application. Drawing on their backgrounds—Jacqueline as a career litigator and former government counsel and Damien as a legal technologist—they provide a roadmap for navigating the "trough of disillusionment" toward a state of "enlightenment".

In this Conversation, we explore:

• The power of Retrieval Augmented Generation (RAG): How connecting symbolic AI with LLMs reduces hallucination rates to near zero.
• The shift from hourly to value-based billing: Why AI efficiency forces a rethink of the ‘slowest lawyer wins’ model.”
• Access to justice: How shrinking the unit cost of legal work can unlock the "latent market" of 92% of unmet legal needs.

Mentioned in this Conversation:

• Co-Intelligence by Ethan Mollick.

After surviving nearly two decades in solitary confinement, Ian Manuel brings a deeply personal perspective to the meaning of justice. Drawing from his lived experience, he challenges the legal system to pair accountability with empathy—calling for both technological and systemic changes to ensure no one is defined solely by their worst mistake.

In this conversation, we explore:

• Ian’s journey from a juvenile life sentence to becoming an advocate for people the system overlooked.
• The psychological toll of solitary confinement and the resilience of the human spirit.
• How legal technology can be used as a tool for liberation.

Mentioned in this conversation:

• My Time Will Come: A Memoir of Crime, Punishment, Hope, and Redemption by Ian Manuel.
• The Equal Justice Initiative (EJI) and Bryan Stevenson.

Harvard professor and best-selling author Sarah Lewis reveals how visual narratives—from courtroom photography to AI-generated imagery—hold the power to either uphold systemic bias or dismantle it. 

The conversation moves beyond the surface of courtroom aesthetics and virtual backdrops to examine how legal technologies can either reinforce systemic inequalities or become tools for greater inclusion. From the evolving role of AI in justice to reimagining legal education, this discussion offers a thoughtful exploration of how seeing differently can lead to justice done differently.

In this conversation, we explore:

• The gift of failure: How the legal profession can move past risk-aversion to embrace "near wins" as fuel for justice.
• Narrative as evidence: Why historical civil rights victories like Brown v. Board of Education relied as much on photographers as they did on lawyers.
• The ethics of AI imagery: The dangers of historical bias in machine learning and how tech companies can design for "representational excellence."

Mentioned in this conversation:

• The Rise: Creativity, the Gift of Failure, and the Search for Mastery by Sarah Lewis
• The Black List created by Franklin Leonard

As lawyers and law firms have made the effort to meet clients where they are, the transition to remote work was well underway in the legal profession long before the COVID pandemic made it a necessity. In this episode, we hear about what a remote experience looks like for three very different firms: an internationally-distributed law firm, a digital-first law firm, and a law firm that delivers legal services from an RV.

Specific topics highlighted in this episode include:

• How lawyer mobility contributes to an improved client experience
• The technology that enables a remotely-delivered client experience
• How remote legal work can simultaneously improve access to justice and the client pipeline for law firms
• How to manage remotely distributed legal teams

Listen now to learn how to ensure a great client experience whether you’re working in the office, from the courthouse, or on the road.

Our Guests

Mitch Jackson

Jon Mitchell “Mitch” Jackson is a senior partner and founding attorney of Jackson & Wilson. He has represented clients in the Orange County, CA, area for over 30 years, and he is committed to providing the trustworthy and skilled legal representation people need during the most difficult times of their lives—after a serious accident or the loss of a loved one. He has met with considerable success in this endeavor, recovering millions on behalf of the injured, including numerous multimillion-dollar settlements and verdicts. Also known as “The Streaming Lawyer,” Mitch is a legal social media expert who speaks regularly across the US and teaches other lawyers how to market themselves better. You can follow Mitch on Twitter at @mitchjackson

Justin Osborn

Justin Osborn is a founding member of Counsel Carolina (Osborn Gambale Beckley & Budd PLLC), whose personal advocacy for fairness and progressive social policies led to the firm’s RV-based mobile services program. A former insurance adjuster and insurance defense lawyer, Justin now represents clients against the same corporate and insurance interests he once defended. A proud tribal citizen of the Cherokee Nation and one of the first in his family to obtain a college degree, Justin has rededicated his career to making legal services more equitable and universally accessible. You can follow Justin on Twitter at @justin_osborn

León Fernando del Canto

León Fernando Del Canto leads Del Canto Chambers’ International Tax & Legal team. In 2006 he became the first Spanish citizen to hold a double qualification as a barrister in England and Spanish Abogado and he joined The Honourable Society of Lincoln’s Inn in London. He is a member of the Worshipful Association of Tax Advisers in the City of London, and a liveryman of the City of London. Fernando has represented clients in Madrid, New York, London, Doha, and Hong Kong. He advocates for private clients and their families as well as for companies with international operations. You can follow Fernando on Twitter at @LeonFDelCanto

How do you measure the impact of a big idea? Shifting to a client-centered model is a big, broad change for the legal profession—but how can law firms tell it’s the right one? In the latest episode of Matters, Jack and Nefra are joined by a data scientist and three law firm leaders to learn what firms should be looking at, business metrics to focus on, and how their clients are letting them know they’re on the right track.

Specific topics highlighted in this episode include:

• Data points and metrics for measuring the impact of a shift to a client-centered model
• What ‘success’ means to different law firms
• The opportunities for law firms to collect feedback from clients

Listen now to learn how to measure what matters to your law firm.

Our Guests

Nika Kabiri

Nika Kabiri has spent 20+ years studying how people make decisions in a variety of contexts. She has a JD from the University of Texas, a PhD in Sociology from the University of Washington, and currently teaches Decision Science at the University of Washington. Nika has worked with businesses of all sizes, including Amazon, Microsoft, VMware, Sony, Oakley, PepsiCo, General Mills, Anheuser-Busch InBev, the Seattle Seahawks, Zillow, Expedia, Smartsheet—and Clio. She is also an Advisor at Madrona Venture Labs, where she helps startups get their footing. You can follow Nika on Twitter at @nikakabiri

Rebecca Bell

Rebecca is the founder and principal attorney at rb LEGAL, LLC. She started the firm to provide people with real and  practical solutions to their legal questions in a welcoming and comfortable environment. Rebecca brings a wealth of expertise, wisdom, experience, and compassion to the rb LEGAL team. She helps clients with their probate, estate planning, business law, and equine law issues. Her hobbies include Latin & Ballroom dancing and spoiling her dogs. She prefers Haagen-Dazs® Vanilla or Culver’s® Chocolate Custard. You can follow Rebecca on Twitter at @rb_legal.

Katy Young

On a typical day you’ll find Katy, Ad Astra’s managing partner and boss lady extraordinaire, out on the front lines advocating fiercely for her clients — as well as behind the scenes, helping to build a law firm full of wonderful people she’s proud of. “You miss 100% of the shots you don’t take” is one of Katy’s life mantras, and she’s never backed down from pursuing the outcome that represents a true victory for each client. You can follow Katy on Twitter at @astralegalsf.

León Fernando del Canto

León Fernando Del Canto leads Del Canto Chambers’ International Tax & Legal team. In 2006 he became the first Spanish citizen to hold a double qualification as a barrister in England and Spanish Abogado and he joined The Honourable Society of Lincoln’s Inn in London. He is a member of the Worshipful Association of Tax Advisers in the City of London, and a liveryman of the City of London. Fernando has represented clients in Madrid, New York, London, Doha, and Hong Kong. He advocates for private clients and their families as well as for companies with international operations. You can follow Fernando on Twitter at @LeonFDelCanto

The COVID pandemic has fundamentally and permanently transformed industries around the world—and the legal industry is no exception. In this episode of Matters, we’ll speak to organizational leaders, educators, and practicing attorneys to hear how the practice of law has changed—and what attorneys need to do to keep pace.

Specific topics highlighted in this episode include:

• How the COVID pandemic highlighted the mental health crisis in the legal industry
• How client behaviors have permanently changed as a result of the COVID pandemic
• How professional organizations can support law firms through the transition

Listen now to learn how your law firm needs to adapt to these permanent changes.

Our Guests

Charlene Theodore

Ms. Theodore, the President of the Ontario Bar Association, draws on her experience as a lawyer who has practiced international human rights, labour and employment law. She started her career as a human rights lawyer, appearing before administrative tribunals and various levels of court, including Canada’s Federal Court of Appeal.  She also represented the interests of Canadians of African descent before federal and provincial legislative committees, as well as United Nations human rights treaty bodies. She then focused her practice on labour and employment law, specializing in complex workplace and union challenges.  Her advocacy extends beyond the courtroom to society at large through her dedication to community service. You can follow Inti on Twitter at @CharleneYYZ

Elise Buie

Elise Buie is Founder of Elise Buie Family Law Group, a family lawyer, and a Guardian ad Litem based in the Seattle area. Elise is an active member of the Washington Bar and many other bars and legal organizations. She provides her time and services through the Moderate Means program of the Washington State Bar Association, and she completed the ABA Family Law Trial Advocacy Institute sponsored by the National Institute for Trial Advocacy in Boulder, Colorado. Elise and her firm focus on advocating for children's best interest in high-conflict divorce and dependency matters. You can follow her on Twitter at @elisebuie

Mitch Jackson

Jon Mitchell “Mitch” Jackson is a senior partner and founding attorney of Jackson & Wilson. He has represented clients in the Orange County, CA, area for over 30 years, and he is committed to providing the trustworthy and skilled legal representation people need during the most difficult times of their lives—after a serious accident or the loss of a loved one. He has met with considerable success in this endeavor, recovering millions on behalf of the injured, including numerous multimillion-dollar settlements and verdicts. Also known as “The Streaming Lawyer,” Mitch is a legal social media expert who speaks regularly across the US and teaches other lawyers how to market themselves better. You can follow Mitch on Twitter at @mitchjackson

Bill Henderson

Bill Henderson joined the Indiana University Maurer School of Law faculty in 2003 following a visiting appointment at Chicago-Kent College of Law and a judicial clerkship for Judge Richard Cudahy of the U.S. Court of Appeals for the Seventh Circuit. Drawing upon more than a decade of research, Bill is a sought-after commentator on the changing legal marketplace and has accumulated numerous awards. In the last five years, he has been named one of the 100 Most Influential Lawyers in America by the National Law Journal, the Most Influential Person in Legal Education by National Jurist Magazine, and one of the inaugural group of “Legal Rebels” profiled by the ABA Journal. You can follow Bill on Twitter at @wihender

In the past couple of episodes, we’ve looked at practical ways to put yourself in your client's shoes, and to adopt a client-centered mindset. This episode, we’re looking at how to put client-centered ideas into practice at your firm, and to help us, four legal experts shared their knowledge around implementing techniques that improve the experience for clients and members of the firm. 

Specific topics highlighted in this episode include:

• Why it’s important to put client-centered practices in place at your firm
• How to build your practice around the client experience
• How to try new techniques, evaluate them, and make adjustments over time
• The value of getting feedback from clients, and using it to improve your practice

This episode features Mitch Kowalski, Shreya Ley, Elise Buie, and Fernando del Canto. Listen now to hear their valuable perspectives.

Our Guests:

Mitch Kowalski

Mitch Kowalski is a lawyer, writer, keynote speaker, legal operations consultant, and author of the critically-acclaimed books The Great Legal Reformation and Avoiding Extinction: Reimagining Legal Services for the 21st Century. A College of Law Practice Management Fellow and a Fastcase 50 Innovator Award honoree, Mitch has general counsel, international law firm partner, and Board of Directors experience. As a legal consultant, he helps teams and law firms to deliver value and perform at higher levels. Mitch speaks on legal service innovation at conferences around the world and writes for a variety of publications about the challenges of legal operations. You can follow him on Twitter at @MEKowalski

Shreya Ley

Shreya Ley is a Lawyer-Human with LayRoots. While on a surfing trip in Westport, WA, she and her partner in life and business chose to open a practice focusing on estate planning and asset protection. They have a special interest in how small business owners can protect their personal assets, continue to provide for their families in case of an emergency, and protect their intellectual property. A graduate of the University of Texas at Austin, Shreya received her J.D. at Tulane University Law School in 2010. You can follow Shreya on Twitter at @layyourroots

Elise Buie

Elise Buie is Founder of Elise Buie Family Law Group, a family lawyer, and a Guardian ad Litem based in the Seattle area. Elise is an active member of the Washington Bar and many other bars and legal organizations. She provides her time and services through the Moderate Means program of the Washington State Bar Association, and she completed the ABA Family Law Trial Advocacy Institute sponsored by the National Institute for Trial Advocacy in Boulder, Colorado. Elise and her firm focus on advocating for children’s best interest in high-conflict divorce and dependency matters. You can follow her on Twitter at @elisebuie

León Fernando del Canto

León Fernando Del Canto leads Del Canto Chambers’ International Tax & Legal team. In 2006 he became the first Spanish citizen to hold a double qualification as a barrister in England and Spanish Abogado and he joined The Honourable Society of Lincoln’s Inn in London. He is a member of the Worshipful Association of Tax Advisers in the City of London, and a liveryman of the City of London. Fernando has represented clients in Madrid, New York, London, Doha, and Hong Kong. He advocates for private clients and their families as well as for companies with international operations. You can follow Fernando on Twitter at @LeonFDelCanto

In our last episode, we explored how to adopt a client-centered mindset at your firm. In this episode, we’ll build on that discussion to understand how to truly put yourself in your clients’ shoes. By doing so, you’ll be able to provide better service, and to align your firm’s interests with those of your clients.

Specific topics highlighted in this episode include:

• The importance of understanding who your clients are
• Techniques you can use to gain insight into your clients’ wants and needs
• The value of the client journey mapping technique
• Which technologies and practices make things easier for clients
• How to increase Access to Justice by serving “the latent legal market”

This episode features three practicing attorneys who excel at providing modern client service. To hear what they have to say, listen now!

Our Guests:

Inti Martínez-Alemán

Inti Martínez-Alemán, a third-generation lawyer from Honduras, is the winner of the 2020 Reisman Award for Excellence in Client Service. Inti is bilingual and has been practicing law since 2008. Inti practices business, civil, and employment litigation. His bilingual office, Ceiba Fôrte Law Firm, serves Hispanics in the state of Minnesota, and in New York State. Ceiba Fôrte’s fees adapt to the needs of every client—especially for hardworking Hispanics, foreigners, expats, transplants, and other immigrants. Foreign clients and companies prefer Ceiba Fôrte because the firm offers alternative fee arrangements like flat fees, contingency, and hybrids. You can follow Inti on Twitter at @LegalMines

Rachel Roche

Rachel Roche LL.M. TEP, Founder and Solicitor Director of Roche Legal in York, England, is an experienced, fully-qualified private client solicitor. In 2018, Rachel was honored as the Law Society of England & Wales’ Sole Practitioner of the Year. Roche Legal focuses on Wills & Probate, Powers of Attorney, and Court of Protection work in the UK. In addition to her role at the firm, Rachel is also a Commissioner for Oaths, a full member of the Society of Trust & Estate Practitioners (STEP), and a Full Accredited Member for Solicitors for the Elderly (SFE). Rachel is also the winner of the 2020 Reisman Award for Legal Innovation. You can follow Rachel on Twitter at @Roche_Legal

Tiffany Graves

Tiffany M. Graves serves as Pro Bono Counsel at Bradley, a 500-attorney law firm with offices across the southern United States. In her role, Tiffany oversees the development and administration of the firm’s pro bono programs. Prior to joining Bradley, Tiffany was the executive director of the Mississippi Access to Justice Commission, where she led a 21-member commission created by the Mississippi Supreme Court and promoted its initiatives to improve and expand access to civil justice to the nearly 700,000 Mississippians living in poverty. In addition, Tiffany previously served as interim director and adjunct professor for the Pro Bono Initiative at the University of Mississippi School of Law, and as executive director and general counsel for the Mississippi Volunteer Lawyers Project. You can follow Tiffany on Twitter at @tiffmgraves