The AI Drop™

Freshfields

Unlock the future of artificial intelligence with The AI Drop™, a podcast dedicated to delivering cutting-edge insights on how AI is transforming industries worldwide. Each episode features expert interviews and actionable strategies to help you harness AI, drive business value, and navigate evolving legal challenges. Fresh drops every week so you never miss a beat.

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#31
Tuesday · 25 min
The AI Drop™ #30: Out of the Shadows: Seeing and Steering Enterprise AI Agents with Hanah-Marie Darley
Most companies can’t govern AI agents they can’t see. Once visible, the challenge is keeping them useful without losing control. Host Anna Gressel welcomes Hanah-Marie Darley, co-founder and Chief AI Officer of Geordie AI, to discuss the challenges of monitoring and governing agents at scale. Hanah explains what changes when companies run hundreds of thousands of agents, from high-volume logs to behavior that varies across tasks. She also shares how agent visibility continues to evolve. Looking ahead to 2027, Hanah expects businesses to move beyond large language models toward a broader mix of specialized and efficient models. Tune in to hear what it takes to keep agents productive, secure, and accountable as they spread across enterprise workflows. Connect and Learn More ☑️ Hanah-Marie Darley | LinkedIn ☑️ Geordie AI | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#30
November 3 · 23 min
The AI Drop™ #29: Beyond the Ballot: What the Midterms Mean for AI Policy with Chloe Autio
For AI companies, the most consequential result of the 2026 midterms may not be a new law but a subpoena. In this special midterm edition, Anna Gressel welcomes Chloe Autio, founder and CEO of AI policy consultancy Autio Strategies, to discuss where AI policy pressure may emerge after Election Day. Chloe explores why data centers have become a campaign flashpoint, and why a Democratic House could bring greater scrutiny of AI companies through congressional investigations, subpoenas, and testimony. Looking ahead, she flags agentic commerce, including the growing policy questions raised by AI agents transacting on users’ behalf, as a key issue to watch in 2027. Connect and Learn More ☑️ Chloe Autio | LinkedIn ☑️ Autio Strategies | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#29
October 27 · 28 min
The AI Drop™ #28: Product-Market Fit Isn’t Forever: Why AI Founders Must Keep Iterating with Juliet Bailin
AI companies may be overvalued in places, but Juliet Bailin doesn’t see today’s market as another dot-com bubble. A venture partner at Kindred Capital, Juliet joins host Anna Gressel to explain why she believes AI is creating lasting value even if the market eventually corrects. They explore whether customers will ultimately pay the full cost of AI models now subsidized by venture capital, why physical AI may prove harder to copy than software, and what Juliet looks for in founders building in fast-changing markets. Juliet also shares how she’s rethinking the traditional venture fund model to give experienced investors more time to focus on founders and investing. With product-market fit less durable than it once was, she argues that founders need to pay close attention to customers and keep adapting as markets change. Connect and Learn More ☑️ Juliet Bailin | LinkedIn ☑️ Kindred Capital VC | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#28
October 20 · 20 min
The AI Drop™ #27: On the Front Lines: Tracking AI Regulation From California to New York with Megan Kayo
California and New York are taking different approaches to AI oversight, but both reflect a shift toward more active regulation. Host Anna Gressel welcomes back Freshfields partner Megan Kayo to share key takeaways from PLI’s first AI governance event in New York, which Anna chaired. The event featured keynote fireside chats with two leading state regulators, offering a view from the front lines of AI regulation in California and New York. Megan shares insights from her conversation with Sabrina Ross, Chief Privacy Auditor at CalPrivacy, on California's new automated decision-making rules and cybersecurity risk assessments, and on why compliance responsibility stays with the business, not its vendors. Anna discusses her conversation with Kaitlin Asrow, Acting Superintendent of the New York Department of Financial Services (“DFS”), about the RAISE Act and DIGIT, DFS’s new frontier AI office. Anna and Megan also explore New York City’s latest AI proposals and California’s wave of new AI laws. Against this increasingly complex patchwork of state requirements, the episode offers businesses a timely look at where AI regulation is heading and what to watch next. IConnect and Learn More ☑️ Megan Kayo | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#27
October 13 · 22 min
The AI Drop #26: A View from Two Desks: The Dispatch from London on AI Policy, IP, and the Future of Personal Agents with Giles Pratt
When two lawyers who co-head a global AI practice spend the day at a high-level policy forum, they come home with a lot on their minds. In this episode, Anna Gressel and Giles Pratt, Freshfields' Global Head of IP/Data Practice and Global Co-Head of AI, cover The Observer's new global AI cities rankings, the copyright questions looming over AI-generated code, the UK's pro-innovation policy bet — and a prediction for 2027 that involves all of us. Consider it the debrief that didn't stay in the room. Giles explains why investors now ask whether the AI work they fund can actually be owned, and how UK law uniquely protects computer-generated works for 50 years, versus life plus 70 for a human author. He also warns that unsettled rules on model training could shape where data centers get built. Connect and Learn More ☑️ Giles Pratt | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#26
October 6 · 27 min
The AI Drop #25: The Mouse and the Maze: How to Govern AI Agents That Keep Evolving with Jason Stanley
In this episode of The AI Drop, Jason Stanley, Head of Applied AI Research at ServiceNow, returns for another discussion with host Anna Gressel on one of the most pressing challenges in AI governance: how to oversee AI systems that continue to adapt after deployment. Together, they explore what adaptive and self-improving AI means for enterprise risk and governance. He explains why an AI system can excel at one task yet fail at a slightly reworded version of it, and why critical governance controls must sit beyond an agent's ability to modify them, even if those safeguards may not hold indefinitely. Jason and Anna also discuss how contracts can transform voluntary standards into binding obligations more quickly than new regulation, and why effective oversight must extend to how AI systems evolve at runtime. For legal, risk, and technology leaders alike, this conversation gives insight on the governance questions likely to dominate 2027. Connect and Learn More ☑️ Jason Stanley | LinkedIn | github ☑️ ServiceNow | LinkedIn | Instagram | Facebook | X | YouTube ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#25
September 29 · 22 min
The AI Drop #24: The Seatbelt, Not the Brake: Building AI Governance That Enables Innovation with Polina Zvyagina
The most effective AI governance programs don't slow innovation down. They create the guardrails, visibility, and trust needed to scale AI responsibly and confidently. In Part 2 of this conversation, Anna Gressel welcomes back Polina Zvyagina, Director and Executive Lead Counsel for AI & Data Governance at General Motors, for a deep dive into what effective AI governance looks like in practice. From NIST's AI Risk Management Framework to the challenges of AI agents, shadow AI, evaluations, and scalable governance, Polina shares practical insights on building governance that works in the real world. The conversation also examines why governance should function as a "seatbelt, not a brake," helping organizations innovate faster while maintaining trust, transparency, and accountability. They also discuss the importance of human judgment, evaluating AI outputs, fitness-for-purpose testing, and avoiding overreliance on AI systems as organizations scale adoption. For governance leaders, legal professionals, and business leaders alike, this episode offers a important insights for building responsible AI programs that can evolve alongside the technology. Connect and Learn More ☑️ Polina Zvyagina | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#24
September 22 · 24 min
The AI Drop #23: The 360-Degree View: How AI Product Counsel Build Trust at Scale with Polina Zvyagina
In this episode of The AI Drop, Anna Gressel sits down with Polina Zvyagina, Director and Executive Lead Counsel for AI & Data Governance at General Motors, to explore one of the most sought-after legal roles in tech today: AI Product Counsel. Polina shares how she helped pioneer the AI product counseling field and explains why the future of AI governance depends on embedding legal, policy, and risk expertise directly into the product development process. Together, Anna and Polina explore how organizations can move beyond treating AI governance as a compliance exercise and instead use it to enable responsible innovation. Polina also offers a behind-the-scenes look at the AI product counsel role, sharing how legal teams work alongside engineers and business leaders to balance innovation with privacy, transparency, consumer protection, and other key risks. For lawyers and governance professionals alike, the conversation provides practical insights into one of the fastest-growing roles in the AI ecosystem. Connect and Learn More ☑️ Polina Zvyagina | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#23
September 15 · 19 min
The AI Drop #22: Hardware, Software, and Everything in Between: How Export Controls Are Adapting to the Full AI Stack with Nabeel Yousef
Export controls have always started with a simple question: what is the thing, and where can it go? AI is complicating that equation. Nabeel Yousef, a Freshfields partner whose practice spans US sanctions, export control, and anti-corruption law, joins host Anna Gressel to map where frontier technology meets national security regulation. Together, they explore the three issues clients are grappling with most: semiconductor controls, the software powering AI infrastructure, and the potential impact of the pending Remote Access Security Act. They also discuss the risks of integrating Chinese AI models, the emerging East-West divide in AI development, and why many compliance programs have become outdated “Frankensteins” in a rapidly evolving regulatory landscape. As Nabeel explains, one of the biggest compliance risks is assuming your house is already in order. Connect and Learn More ☑️ Nabeel Yousef | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#22
September 8 · 21 min
The AI Drop #21: Least Agency: Rewriting the Cybersecurity Playbook for AI Agents with Megan Kayo
Megan Kayo, a Freshfields partner focused on AI, cybersecurity, and privacy, joins host Anna Gressel to unpack what makes agentic incidents fundamentally different from traditional cybersecurity incidents. Since agents act on their own, spawn sub-agents, and reason unpredictably, they strain frameworks like NIST built for human threat actors. Megan explains why agents require immutable identities and adherence to the principle of "least agency," and why shadow AI and third-party sprawl make the risk surface so hard to govern. Drawing on her experience guiding clients through incidents, Megan also offers practical steps security and legal teams can take to get ahead of agentic risk. Connect and Learn More ☑️ Megan Kayo | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#21
September 1 · 24 min
The AI Drop #20: The Morning Brief: How AI Workflows Are Transforming Legal and Governance Teams with Suchismita Pahi
Whether you're automating your morning to-do list or an entire enterprise compliance program, one principle separates success from failure: figure out the process before you hand it to the tool. Suchismita Pahi, Lead Counsel for Product at Databricks, joins host Anna Gressel to trace that thread from her own daily AI workflows to the AI compliance program she built from the ground up . Instead of a legal checklist nobody wants to fill out, Suchi took an operations-first approach that integrates legal, IT, and security. She and Anna dig into what changes as passive LLMs give way to an agentic enterprise — identity management, the principal-agent problem, acceptable error rates - and they share practical insights on building cross-functional AI governance. The episode concludes with a look at the AI use cases that excite Suchi most, including the future of AI-powered scientific research and innovation. Connect and Learn More ☑️ Suchismita Pahi | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#20
August 25 · 36 min
The AI Drop #19: From Mycelia to Machines: Rethinking Intelligence in an Age of AI with Dr. Rumman Chowdhury
Intelligence isn't a fixed quantity we can measure — it's a construct, and the moment we insist on measuring machines against ourselves, we could miss what they can do and misjudge what they can't. Dr. Rumman Chowdhury — founder and CEO of Humane Intelligence and the first U.S. Science Envoy for AI — joins host Anna Gressel to unpack the ideas behind Thinking About Thinking, her podcast and the book she's now writing. Drawing on everything from mycelial networks to a recent Oxford debate on legal personhood, Rumman and Anna also explore reasoning, anthropomorphizing, and the human skills — discernment, curiosity, imagination — that AI can't automate. Connect and Learn More ☑️ Rumman Chowdhury | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#19
August 18 · 29 min
The AI Drop #18: What's a Robot Worth? Valuation, Data & the Power of Physical AI with Shenwei Zhu and Lauren Schwartz
Is physical AI ready for primetime? Recorded live at Citi's Robotics and Physical AI Conference, this episode captures a market at an inflection point, maturing in "dog years" as it accelerates from demo to deployment at breakneck speed. Host Anna Gressel is joined by Shenwei Zhu, a Citigroup managing director covering industrial technology and robotics, and Lauren Schwartz, CISO and General Counsel of Centific, a global data and AI solutions company. Together they explore why data has become both the bottleneck and the moat in physical AI, how investors evaluate robotics companies on unit economics and customer value, and why the winning proposition is to sell measurable outcomes. Shenwei and Lauren also weigh liability gaps and offer founders hard-won advice on capital and data strategy. Connect and Learn More ☑️ Lauren Schwartz | LinkedIn ☑️ Shenwei Zhu | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#18
August 11 · 18 min
The AI Drop #17: Delegate the Decision, Not the Liability — How the SEC Views Agentic AI with Melissa Hodgman
In this episode, host Anna Gressel is joined by Freshfields Partner Melissa Hodgman, a former SEC enforcement official, who traces that arc from the SEC’s interest in pattern-spotting tools built after the 2008 crisis to today's "AI washing" disclosure cases and other areas of SEC enforcement interest. As Melissa puts it, “you can delegate decision-making to a machine, but you can't delegate liability.” For years, enforcement turned on what a single person knew — knowledge firms could contain with walls, locked doors, and policies. Melissa explains why a learning system that moves information across an organization makes that a far harder question: what did the system know? From there she unpacks how investor protection shapes the agency's interest in agentic AI, and what belongs on a general counsel's hit list. Her closing advice — engage regulators early, and treat securities law as principle-based. Connect and Learn More ☑️ Melissa Hodgman | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#17
August 4 · 22 min
The AI Drop #16: The AI Race: China's Open-Source Play for Global AI Adoption with Beth George
In this episode of The AI Drop, Anna Gressel sits down with Beth George (Freshfields Partner, Head of US Litigation and Global Co-Head of Strategic Risk Management) to discuss the geopolitical implications of China's latest AI advances, including Kimi K3, and what they signal for the global AI race. Rather than focusing solely on who builds the most powerful model, they explore why the real competition may be over AI infrastructure, trust, and global adoption. The conversation examines China's open-source AI strategy, the limits of export controls and bans as policy tools, and why accessibility, reliability, and safety may become the defining differentiators in the next era of AI. They also discuss the growing role of robotics, AI agents, and cybersecurity risks as AI systems become more deeply embedded in everyday life.
#16
July 28 · 27 min
The AI Drop #15: Designing the Future: How Kohler Is Building an AI-Enabled Enterprise with Eric Tabor and Megan Belcher
Kohler's approach to enterprise AI starts with a simple bet: teach every employee to build and manage their own agents rather than bring in consultants. Eric Tabor, Kohler's chief digital officer, and Megan Belcher, the company's chief legal officer, join host Anna Gressel to explain how that philosophy has shaped both the 153-year-old design company's technology roadmap and its governance model. Eric details Kohler's "two-in-a-box" model, pairing associates with technical partners, and the recent rollout of 3,000 AI agents across the company. Megan explains how legal meets clients' risk tolerance while moving with speed, and how she keeps the board abreast of a rapidly evolving competitive landscape. Their advice for teams starting out with AI: "hold hands...and be willing to jump." Connect and Learn More ☑️ Megan Belcher ☑️ Eric Tabor | LinkedIn ☑️ Kohler ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#15
July 21 · 24 min
The AI Drop #14: Privilege, Meet Prompt: A Practical Guide to AI in the Legal World with Rob McCallum
When privileged prompts pass through an AI tool, whether they stay privileged is a key question coming before courts globally today — and those courts are digging into the facts and terms to decide. Rob McCallum, a Freshfields tech litigator, tells host Anna Gressel that privilege questions come up in his practice pretty much every day, and that the conversation has shifted from whether to use AI at all to how to use it responsibly when privileged communications are in the mix. He and Anna also cover AI note-takers as discoverable records, cross-border differences in privilege law, and where governance over privileged communications and documents actually starts. Connect and Learn More ☑️ Rob McCallum | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#14
July 14 · 26 min
The AI Drop #13: Who Watches the Agents? Governing Work in the Era of Agentic AI with Jason Stanley
As AI agents become more autonomous, who is responsible for overseeing their work? In this episode of The AI Drop, host Anna Gressel is joined by Jason Stanley, Head of Applied AI Research at ServiceNow, for a deep dive into the emerging world of agentic AI governance. Together, they explore why traditional AI governance frameworks may not be enough for autonomous systems, the importance of deployment-specific evaluation, and how organizations can build trust, accountability, and effective human-AI collaboration. Connect and Learn More ☑️ Jason Stanley | LinkedIn | Substack ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#13
July 7 · 26 min
The AI Drop #12: The Honest Oracle: Smart Contracts, AI Agents, and the View from Abu Dhabi, with Magdalena Konig
What happens when agentic AI's agility meets blockchain rigidity? Magdalena Konig, GC of Sirius International Holding — IHC's technology subsidiary — argues the result is paradoxically powerful: a more agile, rigid structure where use cases multiply exponentially. Host Anna Gressel sits down with Magdalena in Abu Dhabi to explore how smart contracts and agents are natural partners, from logistics pipelines that auto-execute payment on delivery to new financial access for the world's unbanked. The conversation also covers governance, liability, and human oversight in increasingly autonomous systems, alongside a look at the UAE's rapid emergence as a global hub for AI, blockchain, and digital infrastructure innovation. The conversation also covers governance, liability, and human oversight in increasingly autonomous systems, alongside a look at the UAE's rapid emergence as a global hub for AI, blockchain, and digital infrastructure innovation. Connect and Learn More ☑️ Magdalena Konig | LinkedIn ☑️ Sirius International Holding | LinkedIn | Instagram ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music
#12
June 30 · 32 min
The AI Drop #11: Concrete and Capital: Building the Backbone of the AI Era, with Jessamy Gallagher and Harry Evans
Data centers are dominating headlines — and the pressures behind them are only growing. In this episode, host Anna Gressel welcomes Jessamy Gallagher, Freshfields partner and global head of the firm's Energy and Real assets group, and Harry Evans, a Freshfields partner in Singapore focused on tech, telecom, and financial services. They map the data center boom from two angles: global capital markets and Asia's build landscape. They break down why AI has nearly doubled sector growth rates, how asset-backed securitization is unlocking new capital pools, and why power is the fundamental long-term constraint. The conversation covers off-grid power solutions, community pushback from Tokyo to Ireland, and what keeps investors awake: geopolitics, cooling constraints, and whether quantum chips could eventually upend today's infrastructure stack. Connect and Learn More ☑️ Harry Evans | LinkedIn ☑️ Jessamy Gallagher | LinkedIn ☑️ Anna Gressel | LinkedIn ☑️ Freshfields ☑️ Subscribe Apple Podcasts | Spotify | Amazon Music

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