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When everyone said yes, Jordan Breslow said no, and that decision kept his company out of scandal.

The longtime Silicon Valley GC (Geoworks, Opsware, Silver Spring Networks, Etsy) joins host Cecilia Ziniti to share what decades inside tech taught him about courage, integrity, and how to stand by your instincts when the pressure is high.

He tells the now-legendary story of advising Ben Horowitz not to backdate stock options just before the Silicon Valley scandal broke, explains why he sent Etsy’s IPO documents back to outside counsel to “rewrite them in English,” and reflects on how lawyers can stay human as AI reshapes their world.

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@Jordan Breslow on LinkedIn

Books, Authors & Thinkers Mentioned:
– The Hard Thing About Hard Things by Ben Horowitz
– Adam Grant (leadership and integrity frameworks mentioned by CZ)

Other References:
– Opsware (formerly LoudCloud)
– Etsy IPO and B Corporation certification
– Andreessen Horowitz (A16Z)
– Silver Spring Networks
– ASCAP & BMI (analogy for AI creator compensation)
– Down the Rabbit Hole (band)
– Lake Tahoe residency

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Holly Hogan has built her career leading through change, from nearly a decade scaling Automattic (WordPress.com, Tumblr, Day One) to her new role as General Counsel at Deepgram, a frontier voice AI company.

In this episode, she shares how to create AI guardrails that enable innovation, why “clear prompting reflects clear thinking,” and how small language shifts can transform how legal teams work and are perceived.

You’ll hear:
– What it means to be a “GC-in-Residence” at Mayer Brown and why firms need visibility into the in-house mindset (01:11–04:46)
– Automattic’s legal evolution from two lawyers to global scale (05:19–06:59)
– A nine-year free-expression case in Turkey that tested principle and perseverance (07:13–09:00)
– Building agile teams with “home bases” and embedding legal in the business (10:46–13:03)
– “Clear prompting reflects clear thinking” — why lawyers are built for the AI era (20:35–23:12)
– Using AI like a “supercharged thesaurus” to write, edit, and communicate better (23:12–24:04)
– How leadership language changes team culture (“We helped close the deal,” not “We cleared legal”) (24:33–26:35)
– Seeing legal as persuasion: “You’re selling to the lawyers on the other side” (27:53–28:55)
– Building responsibly in voice AI while embracing progress over fear (36:12–39:01)
– Why changing your mind is a leadership strength (41:01–42:14)
– Her career advice: Be original—both as a lawyer and as a leader (43:12–44:04)

Holly shows how curiosity, clarity, and originality can guide legal teams through any era of change, from open source to AI and beyond.

Follow Holly:

@Holly Hogan on LinkedIn

Books, Authors & Thinkers Mentioned:
– Decision Quality by Adam Grant
– To Sell Is Human by Daniel Pink

Other References:
– Automattic (WordPress.com, Tumblr, Day One, VIP)
– Mayer Brown GC-in-Residence Program
– Deepgram (Voice AI for the Enterprise)
– CDA 230 and Senator Ron Wyden
– AI Guardrails & Policy Frameworks
– “Clear prompting reflects clear thinking”

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Doug Leeds has lived through multiple technology booms—from the early internet to today’s AI wave. As CEO of Ask.com and IAC Publishing, he went head-to-head with Google, scaled digital publishing, and even pivoted a search engine by partnering with his fiercest competitor. 

Today, Doug teaches leadership and persuasion at UC Berkeley’s Haas School of Business and is co-founding a nonprofit, Really Simple Licensing, to create a licensing protocol for AI and the open web.

Follow Doug:

@Doug Leeds on LinkedIn

You’ll hear:
– Why leadership is persuasion: “getting people to do what you want as if it’s their own idea” (23:09)
– The Catch-22 of being a lawyer-turned-operator—and why he calls law a “better hobby”
– How improv training for 2,000 employees built trust, creativity, and psychological safety
– The WAPOTI framework: “Why Aren’t People Already Doing It?”
– The Three H’s of communication: heard, helped, or hugged
– Why legal should act like product managers, co-designing solutions instead of saying no
– How Really Simple Licensing (RSL) could reshape the economics of content and AI

Doug shows how leaders can evolve across industries and cycles, turning disruption into opportunity with curiosity, persuasion, and yes, silliness.

Books, authors & frameworks mentioned:

– Getting to Yes by Roger Fisher and William Ury

– The Three H’s framework (heard, helped, hugged)

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Today’s guests are Nicole Altman, Senior Counsel, and Kelly Noguchi, Senior Legal Technology and Operations Manager, at Instacart. They are helping shape how a public company’s legal team experiments with, adopts, and scales AI. Together, they show what innovation looks like when it is encouraged and operationalized.

You’ll hear:
– How Instacart Legal made AI exploration part of team and company-wide goals
– Why curiosity and a learning mindset are the foundation for adoption
– Real examples of tools like Contract Compass and Legal@ triage in action
– How leadership and culture drive not only productivity but creativity
– Why legal ops is critical for moving from early experiments to enterprise systems

Nicole and Kelly reveal the human side of scaling legal with AI: the joy, the overwhelm, and the opportunities to lead change across the business.

Follow Nicole & Kelly:

@Nicole Altman on LinkedIn

@Kelly Noguchi on LinkedIn

Books, Authors & Thinkers Mentioned:
– The Worlds I See by Fei-Fei Li
– Radiolab podcast
– More Perfect (Radiolab’s legal spinoff)

Other References:
– MIT study on AI adoption and productivity
– Instacart’s “AI First” company initiative
– Bolt hackathon (Contract Compass project)
– Enterprise AI tools and internal chatbot (“Ava”)

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Today’s guest is Ali Hartley, Chief Legal Officer at SimplePractice. Ali has spent her career navigating healthcare’s toughest challenges at Sutter Health, Favor, and Carbon Health before stepping in to help scale SimplePractice. Along the way, she’s shown how legal can be more than compliance–it can be a growth engine.

You’ll hear:
– How telehealth regulations during the pandemic opened unexpected opportunities
– Why trust is the foundation of every legal and business partnership she builds
– How Ali rolled out AI in her team (with creativity and fun) to save hours of work
– Lessons from serving as both CLO and Chief People Officer
– Why empowering teams to embrace imperfection makes them stronger

Ali’s perspective is a guide for GCs and operators who want to unlock growth, especially in high-stakes, highly regulated industries.

Follow Ali:

@Ali Hartley on LinkedIn

Books & Authors mentioned:
– Mel Robbins (“Let Them, Let Me” framework)
– Michelle Obama (leadership wisdom on confidence and perspective)

Show notes:
– Pandemic-driven telehealth policy changes (cross-state licensing, billing)
– Nevada, Illinois, and New York AI-related laws in therapy/companionship
– SimplePractice private equity spinout

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Peter Katz (GC at Expel; former first GC at Duo Security) shares how he scaled legal inside high-growth cybersecurity companies while keeping the business moving. He explains why great in-house lawyering starts with relationships, clear risk choices, and the humility to say “I don’t know - yet.”

You’ll hear:
– Why Peter left firm life in year four and chose Vanguard to build business context and people management skills
– Building the legal startup inside the startup at Duo—through dual-tracking an IPO and a $2.5B acquisition process
– How Expel’s MDR model shapes legal support, and why privacy × security is where in-house teams add outsized value
– The principle that unlocks speed: informed, collaborative risk decisions instead of “capital-L Legal” answers
– Hiring for ceiling, not tasks: developing future GCs and CPOs
– AI as a tool that gives time back for judgment work across legal and security

The book he rereads in every new role: The First 90 Days by Michael D. Watkins

Follow Peter:
@Peter Katz on LinkedIn

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From 16 years at Southwest to leading legal at JSX, Kerrie Forbes knows what it means to navigate turbulence—regulatory battles, competitor challenges, and high-stakes litigation—while keeping fairness and trust as her North Star. In this episode, she reveals how legal leaders can find clarity at 30,000 feet and on the ground.

You’ll hear:
– How JSX operates under FAA and TSA frameworks while delivering a 20-minute airport experience
– Turning adversarial airport disputes into ribbon-cuttings through relationships and tone shifts
– Why “play fair” is a leadership principle that sustains credibility with regulators and competitors
– The differences between firm and in-house litigation strategy—and knowing when to fight vs. resolve
– How EOS (Traction) and GC AI are helping her team build capacity and accountability
– Preparing the next generation of lawyers (including her daughter, now a 1L) for an AI-driven future

Books Mentioned:
– Traction: Get a Grip on Your Business by Gino Wickman

Follow Kerrie:
@Kerrie Forbes on LinkedIn

Show Notes:

– Kerrie’s journey from Jones Day to Southwest Airlines to JSX CLO
– The real regulatory stack: FAA Part 135/380 + TSA TFSSP
– Case study: Orange County dispute → resolution and ribbon-cutting
– Why “outcomes, not arguments” defines in-house success
– EOS (Traction) as a system for accountability and productivity
– Lessons from building trust with regulators and airport authorities
– Family of lawyers: mentoring the next generation in an AI era
– Leadership values: fairness, positivity, and passion for your company

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What does it look like when a general counsel reframes legal as a growth engine instead of a cost center?

Today’s guest is David Morris, a seasoned GC who has led through IPOs, multi-billion-dollar SPAC transactions, and global market expansion. At TripAdvisor, David helped take the company public, opened new markets, including Cuba, and launched a government affairs function that won the license to sell travel into Cuba. Later, he built Vivid Seats’ legal team from scratch, guiding the company through a $2B de-SPAC during COVID. He’s also rebuilt legal organizations at scale in cybersecurity and high-growth SaaS, championing what he calls a “legal as a product” mindset.

You’ll hear:
– How GCs can earn a true seat at the table with product and business teams
– Building political capital inside a company through early wins and trust
– Lessons from expanding into Cuba, Singapore, and other global markets
– Why government affairs is critical even for $100M companies
– How AI is reshaping legal work, law firm relationships, and career paths for young lawyers
– The future of legal teams as business architects, not departments of “no”

Follow David:

@David Morris on LinkedIn

Books & Authors Mentioned:
– Dune by Frank Herbert
– Liar’s Poker by Michael Lewis
– Works by Thomas Friedman (geopolitics, globalization)

Podcasts Mentioned:
– Everyday AI
– Masters of Scale
– Plain English
– The Ringer

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What does going from writing code to leading legal, compliance, HR, and security at a high-growth tech company look like?

In this episode, Diane Honda shares her journey from Carnegie Mellon software engineer to GC who took Barracuda Networks public, to her current role as Chief Administrative Officer at Redis. Along the way, she’s shaped how companies adopt AI, built legal teams into growth engines, and developed a leadership philosophy rooted in trust, adaptability, and action.

Follow Diane:

@Diane Honda on LinkedIn

Books Mentioned:
– Burn the Boats by Matt Higgins
– The Diamond Eye by Kate Quinn

Show Notes:

– Diane’s path from software engineer to GC to CAO
– Why Redis leans into AI adoption across every function
– How AI is redefining the associate role at law firms
– Trust, risk, and liability when AI generates work product
– Leading through cybersecurity crises and high-stakes board roles
– Developing multi-hat leadership across legal, HR, compliance, and security
– Career decisions that shaped her trajectory from HP to Redis
– Lessons from taking Barracuda public and leading transformative deals

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What does it take for a GC to operate as a true executive leader—driving transformation across legal, compliance, and beyond?

Today’s guest is Chuck Kable, General Counsel and Corporate Secretary at Innovative Renal Care, whose career includes transformative leadership roles at Axiom Medical, Emerus, and Cardon Outreach. Chuck has guided companies through high-value private equity transactions, built legal functions from scratch, and led turnarounds, including a $400M acquisition delivering a 16x valuation increase.

You’ll hear:
– How to align legal strategy with private equity timelines while protecting long-term business health
– Why judgment, trust, and credibility are the foundation of GC leadership
– Making compliance a driver of business value, not a bottleneck
– The benefits and challenges of leading both legal and HR functions
– How to identify and automate low-value work to free up strategic capacity
– Maintaining influence and relationships in an AI-enabled legal function
– Why “thinking time” is a leadership superpower every GC needs

Follow Chuck:
@Chuck Kable on LinkedIn

Books Mentioned:
– Building an Outstanding Legal Team by Bjarne P. Tellmann
– No Fail Meetings by Michael Hyatt

Show Notes:
– Chuck’s path from litigator to multi-hat executive leader
– Lessons from leading a $400M turnaround at Cardon Outreach
– Navigating high-stakes private equity transactions in healthcare
– Building compliance cultures that enable growth
– Integrating legal, HR, and compliance for maximum impact
– Using technology to automate routine work and focus on strategy
– The importance of designing intentional business interactions for legal teams
– Leadership practices for bringing teams along through major change

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