The AI Drop™

Latest Episodes:

The AI Drop™ #30: Out of the Shadows: Seeing and Steering Enterprise AI Agents with Hanah-Marie Darley Nov 10, 2026

Show notes

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.

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☑️ Hanah-Marie Darley | LinkedIn

☑️ Geordie AI | LinkedIn

☑️ Anna Gressel | LinkedIn

☑️ Freshfields

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The AI Drop™ #29: Beyond the Ballot: What the Midterms Mean for AI Policy with Chloe Autio Nov 03, 2026

Show notes

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.

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☑️ Chloe Autio | LinkedIn

☑️ Autio Strategies | LinkedIn

☑️ Anna Gressel | LinkedIn

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The AI Drop™ #28: Product-Market Fit Isn’t Forever: Why AI Founders Must Keep Iterating with Juliet Bailin Oct 27, 2026

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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.

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☑️ Juliet Bailin | LinkedIn

☑️ Kindred Capital VC | LinkedIn

☑️ Anna Gressel | LinkedIn

☑️ Freshfields

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The AI Drop™ #27: On the Front Lines: Tracking AI Regulation From California to New York with Megan Kayo Oct 20, 2026

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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.

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☑️ Megan Kayo | LinkedIn

☑️ Anna Gressel | LinkedIn

☑️ Freshfields

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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 Oct 13, 2026

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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.

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☑️ Giles Pratt | LinkedIn

☑️ Anna Gressel | LinkedIn

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The AI Drop #25: The Mouse and the Maze: How to Govern AI Agents That Keep Evolving with Jason Stanley Oct 06, 2026

Show notes

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.

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☑️ Jason Stanley | LinkedIn | github

☑️ Anna Gressel | LinkedIn

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The AI Drop #24: The Seatbelt, Not the Brake: Building AI Governance That Enables Innovation with Polina Zvyagina Sep 29, 2026

Show notes

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.

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☑️ Polina Zvyagina | LinkedIn

☑️ Anna Gressel | LinkedIn

☑️ Freshfields

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The AI Drop #23: The 360-Degree View: How AI Product Counsel Build Trust at Scale with Polina Zvyagina Sep 22, 2026

Show notes

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.

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☑️ Polina Zvyagina | LinkedIn

☑️ Anna Gressel | LinkedIn

☑️ Freshfields

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The AI Drop #22: Hardware, Software, and Everything in Between: How Export Controls Are Adapting to the Full AI Stack with Nabeel Yousef Sep 15, 2026

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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.

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☑️ Nabeel Yousef | LinkedIn

☑️ Anna Gressel | LinkedIn

☑️ Freshfields

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The AI Drop #21: Least Agency: Rewriting the Cybersecurity Playbook for AI Agents with Megan Kayo Sep 08, 2026

Show notes

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.

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☑️ Megan Kayo | LinkedIn

☑️ Anna Gressel | LinkedIn

☑️ Freshfields

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