The AAAi Podcast

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May 2026

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About the show

AAA CEO & President Bridget McCormack and Killer Whale Strategies founder and startup investor Zach Abramowitz explore the impact of AI on the legal ecosystem and peel back the curtain on the AAA's AI journey in a series of conversations with industry influencers.

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21 recent

May 15, 202631 min

TrialKit and the End of Impossible Discovery

What happens when discovery becomes too large for any lawyer, or even any team, to meaningfully review? In Episode 21 of the AAAi Podcast, Bridget McCormack and Zach Abramowitz speak with Ariel Deshe, founder of TrialKit, about the criminal defense case that led him to build the platform and what it reveals about the future of legal AI. The conversation explores the sheer volume of modern discovery, wrongful convictions, and how AI is helping lawyers take on cases that were previously too costly or too complex. Bridget also connects these issues to the broader vision behind the AAA's AI Arbitrator: expanding resolution options for disputes that often go unresolved because traditional processes are too expensive or impractical. Ariel explains why criminal defense lawyers have been quick to embrace technology that can uncover critical evidence hidden within overwhelming volumes of data, in cases where the stakes are immediate and deeply human. Episode 21 highlights a version of legal AI that often gets overlooked, showing how it can help lawyers do work that is otherwise practically impossible under the weight of modern discovery and rising legal costs.

April 16, 202637 min

Governance Is the Key: How Legal Teams Are Learning to Move Fast Without Breaking Trust

In this episode of the AAAi Podcast, Bridget McCormack and Zach Abramowitz record live from Legalweek in New York to explore a clear shift in legal AI. The risk of not moving is now greater than the risk of moving. AI is no longer theoretical, and whether it works is no longer the question. The focus has shifted to how to deploy it in a way that builds trust and scales safely. That is where governance comes in. The conversation now centers on how organizations can move quickly while maintaining trust and managing risk effectively. For legal leaders and operators navigating AI implementation, this episode offers a practical look at what is working today and what comes next.

March 5, 202629 min

Why The AI Arbitrator is Capturing Attention

In Episode 19 of the AAAi Podcast, hosts Bridget McCormack and Zach Abramowitz discuss why the AI Arbitrator is gaining mainstream attention and why governance, not hype, is the real driver of AI adoption. They examine why technology is now the primary strategic focus for 38% of CLOs, unpack the "Walmart model" of intelligent application, and explain how the American Arbitration Association is using agentic systems to expand dispute resolution options. The episode also explores what responsible AI deployment looks like in 2026 and previews Bridget's upcoming Legalweek panel, "Trust Is the Product," featuring leaders from OpenAI, Moderna, and Freshfields.

January 16, 202651 min

2026 Legal Tech Trends: What's Happening Below the Surface

Legal tech is starting to shift from AI-enhanced tools that help lawyers work faster to AI-native systems that change how legal work gets done. In this episode of the AAAi Podcast, Bridget McCormack and Zach Abramowitz are joined by Bob Ambrogi, the founder of LawSites and host of the LawNext podcast, and Timo Karakashev, founder of Cosmonauts, to explore what this shift looks like heading into 2026. They discuss new platform models, emerging AI-native law firms, and the move toward AI as a decision-maker in courts and arbitration. At the heart of the conversation is where pressure is building within the legal system, and why some of the most important changes are happening below the surface.

December 4, 202534 min

How the AAA's AI Arbitrator is Transforming Dispute Resolution: Inside the Innovation with AAA COO and CRO Frank Rossi

The American Arbitration Association (AAA) launched its AI Arbitrator in November 2025, and AAAi Podcast hosts Bridget McCormack and Zach Abramowitz sit down with Frank Rossi, AAA COO and CRO, to take listeners inside the project. They explore how the AAA's legacy of trust, neutrality, and innovation shaped the development of the AI Arbitrator, and why the AAA was uniquely positioned to build the AI Arbitrator. Together they share a behind the scenes look at how the system was developed, the testing and safeguards built into it, and how Frank's skepticism shifted to conviction about the potential of AI to transform alternative dispute resolution.

October 8, 202533 min

Dioptra Cofounder and Chief Product Officer Farah Gasmi

What if the real ROI of legal AI isn't efficiency, but lawyer happiness? Bridget McCormack and Zach Abramowitz talk with Farah Gasmi, cofounder and Chief Product Officer of Dioptra, about making contracts less painful with AI. Farah shares how Dioptra helps lawyers get "in the zone," why usable outputs matter more than speed, and how partnering with the AAA adds the trust lawyers need to rely on AI. Social Handles https://www.dioptra.ai/ https://www.linkedin.com/in/farahgasmi/ https://www.artificiallawyer.com/2025/03/18/aaa-partners-with-dioptra-genai-pioneer/

July 31, 202522 min

AAA Chief Marketing Officer Michael Joseloff

Recorded live at Legalweek 2025 back in March, this episode asks a simple question: What happens when a veteran of CBS, Paramount, and Fortune steps into the world of arbitration? Bridget and Zach talk with AAA's new CMO Michael Joseloff about why legal's "business as usual" days are over, what lessons from media's disruption matter now, and how telling the right story builds trust when half a million disputes cross your desk every year.

July 17, 202542 min

Podcast host and founder of Creative Lawyers Jennifer Leonard

In Episode 14 of the AAAi Podcast, Bridget McCormack and Zach Abramowitz sit down with Jennifer Leonard, Chief Innovation Officer at Penn Carey Law and founder of Creative Lawyers. Drawing on her work in legal ethics and education, Jennifer explains why the legal profession does not just need new tools. It needs a new operating system. The conversation covers the limits of traditional training, the role of systems thinking, and how law schools can better prepare lawyers to work with AI while staying grounded in public service.

June 19, 202540 min

Hence Cofounder and Unruly Author Sean West

What if the biggest legal risk today is institutional memory loss? Bridget and Zach talk with Sean West, author of Unruly and cofounder of Hence Technologies, about how geopolitical instability, AI disruption, and legal short-termism are converging. He explains why the future of dispute resolution depends on preserving memory, rethinking incentives, and acting before the storm hits. This episode is a wake-up call for legal leaders who want to do more than just react.

June 5, 202534 min

Professor Richard Susskind

Bridget and Zach talk with Richard Susskind about his new book, How to Think About AI, and what AI means for the future of courts, lawyers, and justice. Richard challenges the legal profession's deep resistance to change and asks: what if access to justice mattered more than preserving legal work as we know it? LinkedIn: ⁠linkedin.com/in/richardsusskind/⁠ X⁠: @richardsusskind⁠ Amazon⁠: How To Think About AI: A Guide For The Perplexed by Richard Susskind⁠ Website: ⁠susskind.com⁠

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