#57 - From Navy Pilot to General Counsel: IPOs and Legal Innovation with Phil Mazzara
Release Date: 12/03/2024
#81 - The New Structure of AI Powered Law Firms
Pearls On, Gloves Off
When many law‑ and consulting‑firms ask “Which AI tool do we buy?” they’re missing the bigger shift: the very business model is changing. In this episode, Mary sits down with David Duncan and Tyler Anderson—two long‑time service‑firm innovators—to explore how AI is not just a new tool, but a structural force reshaping professional services: staffing models, pricing, talent, and even the nature of expertise. In this episode: The pyramid unravels: We revisit the traditional "analyst → manager → partner" model and why AI is eroding the base layers. From pyramid to obelisk:...
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#80 - Harvey AI’s GC: Lawyers Are 20x More Efficient... Now What?
Pearls On, Gloves Off
In this episode of Pearls On, Gloves Off, Mary O’Carroll sits down with John LaBarre, General Counsel of Harvey. From Google to Snowflake and now a leader in legal AI, John’s career reflects the tech world’s evolution. Together, they dig into the pivotal moment we’re living through — when generative AI enters the legal profession not as a futuristic idea but as a productivity‑enhancer in real time. In this episode: Why legal is ripe for AI: He explains how the legal profession acts as a “low‑hanging fruit” for generative AI, given its massive volumes of unstructured data...
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#79 - In House Career Growth: Being a Great Lawyer Isn’t Enough
Pearls On, Gloves Off
In this episode, Mary O’Carroll sits down with Rachel St. Peter, General Counsel at Nestlé Health Sciences US, to unpack a bold career move: stepping into legal ops mid-career to grow beyond the “good lawyer” baseline. From leading global transformation out of Switzerland to reshaping her executive presence and business fluency, Rachel explains how ops experience changed her leadership—and her trajectory. They also dig into the future of in-house legal: AI realities, law firm pricing shakeups, and what the next generation of GCs must bring to the table. In this episode: Why being a...
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#78 - The Joyful Legal Team
Pearls On, Gloves Off
In this episode of Pearls On, Gloves Off, Mary sits down with Jacqueline Lee, Senior Vice President and General Counsel at Flynn Group, to unpack what it takes to lead legal, compliance, and risk functions at scale. Flynn is the parent company behind brands like Panera, Taco Bell, Wendy’s, Planet Fitness, and more, with 75,000+ employees across the U.S., Australia, and New Zealand. Jacqueline shares her journey from big law to being unexpectedly tapped for a GC role just a year into her in-house life. Along the way, she reveals what’s really changed (and what hasn’t) in that transition...
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#77 - Do Law Firms Actually Want Innovation?
Pearls On, Gloves Off
Eddie Hartman has been disrupting legal long before it was fashionable. As Co-Founder of LegalZoom and now a Partner & Board Member at Simon-Kucher, he’s worked with everyone from startups to AM Law 100 firms on pricing, innovation, and tech strategy. In this episode, Mary sits down with Eddie to talk about the legal industry’s industry’s uneasy relationship with change. From AI hype to the stubborn grip of the billable hour, they unpack why so many “innovations” fail, what clients actually mean when they ask about tech, and how law firms can evolve without losing their...
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#76 - Why “Brilliance” Doesn’t Sell: Rainmaker Strategies for 2025
Pearls On, Gloves Off
When it comes to business development in professional services, Matt Dixon has spent decades decoding what actually works—and what doesn't. As a bestselling author and Founding Partner at DCM Insights, he’s reshaped how companies think about sales. Now, with his new book The Activator Advantage, Matt turns his focus to the world of law, consulting, and other relationship-driven fields, where selling is often taboo—but still essential. In this episode, Mary sits down with Matt to unpack what top-performing partners do differently—and why it has nothing to do with cocktail parties or...
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#75 - Owning the AI Narrative (Before Someone Else Does)
Pearls On, Gloves Off
When it comes to legal innovation, Jim Delkousis doesn’t just have a front-row seat—he’s one of the architects of change. As Founder and CEO of PERSUIT, Jim has spent almost a decade transforming how legal departments buy outside counsel services. With billions in legal work processed through the platform, he offers a rare, data-rich perspective on the shift from opaque hourly billing to value-driven, transparent legal spend. In this episode, Mary reconnects with Jim for a wide-ranging and insightful conversation about what’s changing in legal procurement, why, and what it means for...
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#74 - From the Ground Up: Building Legal Ops with Sean Houston
Pearls On, Gloves Off
When you think of legal ops at a global company like Heineken, you might not picture a former sports broadcaster leading the charge. But that's exactly Sean Houston’s path—and it’s given him a unique edge. In this episode, Mary sits down with Sean, Heineken’s Head of Legal Operations, to unpack how he built the function from scratch. From vendor-side lessons to internal change management, Sean shares sharp, actionable insights on making legal ops work in a complex, global environment. In this episode: Unlikely Origins: How Sean went from a mic in hand as a sports broadcaster to a key...
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#73 - Futurist Says: Legal’s Real Risk Is Playing It Safe
Pearls On, Gloves Off
In this episode, Mary sits down with futurist and bestselling author Mike Walsh to explore what happens when a tradition-bound industry like law collides with generative AI. Walsh, CEO of Tomorrow and author of The Algorithmic Leader, has advised the world's biggest companies on digital transformation—and he believes legal is facing a moment of radical reinvention. Together, they pull no punches on what the next decade will bring, why legal might be the most vulnerable industry of all, and how leaders can stop dabbling in AI and start building the future. In this episode: The Law of (AI)...
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#72 - Moderna GC’s AI Strategy
Pearls On, Gloves Off
What does it look like when a general counsel doesn’t just adopt AI—but rewires her entire legal function around it? In this episode, Mary O’Carroll sits down with Shannon Thyme Klinger, Chief Legal Officer at Moderna and President of Moderna Charitable Foundation. Named by the Financial Times as one of the most innovative GCs of the past two decades, Shannon is reshaping what it means to lead a legal team—and a profession—through profound change. In this episode: “AI won’t replace lawyers, but…” Shannon lays out her bold vision: why lawyers who don’t harness AI may get...
info_outlineThis special episode was recorded live at Goodwin's Tech Retreat in San Francisco, where Mary sits down with Phil Mazzara, General Counsel of Astera Labs, to explore the evolving role of the general counsel in today's rapidly changing technological landscape.
Phil's journey is nothing short of extraordinary. Before becoming an attorney, he spent over a decade on active duty as a Navy pilot, bringing a unique perspective to the legal field. With a JD/MBA from Stanford, Phil skipped the traditional law firm route and went straight in-house. Prior to joining Astera Labs, he served as General Counsel and Secretary at Innovium, where he oversaw multiple venture financings, negotiated critical commercial agreements, settled bet-the-company litigation, built a robust IP portfolio, and ultimately led the company through its $1.1 billion acquisition by Marvell Technology.
At Astera Labs, Phil played a pivotal role in taking the company public in March 2023, a challenging year for capital markets. Under his legal guidance, Astera Labs has been riding the AI wave, focusing on AI infrastructure and experiencing significant growth.
In this engaging live conversation, Phil and Mary delve into:
· The Journey to IPO: Phil shares his experiences taking Astera Labs public in a tough market, the importance of choosing the right outside counsel, and how Goodwin played a crucial role in their successful IPO.
· AI in Legal Practice: How AI is impacting the legal profession, both within corporate legal departments and in law firms, and the potential future applications of AI in complex legal work.
· The Evolving Role of General Counsel: Discussing how the general counsel's role has expanded beyond traditional legal services to include compliance, business strategy, and being a key advisor to the executive team.
· Building Strong Law Firm-Client Relationships: Phil offers advice to law firms on how to better serve their clients, emphasizing the importance of understanding the client's business deeply, being proactive, and building trust.
· Quality of Legal Work and Service: How to measure and ensure high-quality legal services, the significance of responsiveness, attention to detail, and open communication.
· Advice for Junior Lawyers: The value of seeking opportunities to engage directly with clients, asking questions to understand their business, and stepping up to deliver work product in front of senior executives.
· Leadership Lessons from the Navy: Phil reflects on how his experience as a Navy pilot informs his approach to leadership, project management, and the use of checklists to ensure quality and reduce errors.
· The Future of Legal Practice: A candid discussion on how AI and technological advancements are shaping the legal industry, the enduring importance of judgment and counsel, and the skills lawyers will need to succeed in the future.
If you're interested in the intersection of law, technology, and business—or if you're curious about how military experience can translate into corporate leadership—this live episode is a must-listen.
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