Boardroom Governance with Evan Epstein

(0:00) Intro

(1:25) About the podcast sponsor: The American College of Governance Counsel

(2:08) Start of interview

(2:51) James D. White’s Origin Story.

(3:57) James’s current work across public and private company boards. 

(6:15) The Jamba Juice Turnaround: taking over as CEO during a crisis, reshaping the culture, and rebuilding the board

(8:46) Combining the Chair and CEO Roles: when it can work, why leadership structure depends on context, and the importance of a strong lead independent director

(10:20) The CEO–Board Chair Relationship: working with The Honest Company CEO Carla Vernón and why trust between the CEO and chair is central to board effectiveness

(13:18) Working With Founders: lessons from Jessica Alba, Ron Shaich and Max Levchin, and navigating the founder–CEO–chair relationship

(15:34) His experience with IPOs: lessons from The Honest Company, CAVA, and Affirm, and why an IPO is the beginning of the journey rather than the destination

(18:04) Private vs. Public Markets: why companies are staying private longer and why James believes the public markets will remain an important source of capital

(19:00) Pattern Recognition Across Boards: how his experience across consumer, retail, restaurant, and food companies informs his role as a director

(21:10) Director Tenure and Overboarding: why James generally thinks about board service in a 7-9 year window and when independence or relevance can begin to fade

(22:40) Board Culture: how meeting structure, communication, onboarding, offboarding, and the balance between strategy and compliance shape board effectiveness

(25:41) Board Evaluations and Refreshment: why boards struggle to remove underperforming directors and how continuous feedback can make renewal easier

(26:14) Are Some Board Skills Becoming Obsolete? How AI and rapid technological change are forcing boards to rethink whether they have the right capabilities around the table

(27:28) Board Diversity: why James believes boards should draw from the broadest possible pool of talent and reflect the customers and markets they serve

(30:10) Directors Academy and the Future of Governance: training the next generation of directors, the craft of governance, and preparing boards for AI and geopolitical change

(32:08) Keeping Pace With Change: why every board should ask whether it has the right people to help management navigate the current moment

(33:22) Books That Have Influenced James:

1. The Leadership Engine by Noel Tichy (2007)
2. Doing What Matters by Jim Kilts (2007)
3. Know What Matters by Ron Shaich (2023)

(34:35) His mentors

(35:00) The quotes he thinks of often, or lives his life by

(36:03) What Makes an Effective Director? Why the best directors understand context, stay in learning mode, ask how they can help, and contribute beyond formal board meetings

(37:18) An unusual passion: jazz and music festivals

(38:20) The living person he most admires: his 94-year-old father, and lessons about hard work and family

James D. White is an experienced CEO, board chair, and director who has served on more than 20 public and private company boards. 

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.

(00:00) Introduction and about the inaugural Boardroom Governance Summit

(1:50) AI and the enduring role of the board: why new technology does not change directors’ fundamental responsibilities, and why human judgment remains essential

(3:32) Demystifying AI: understanding how the technology is actually used inside the business, asking clear questions, and testing AI through real-world applications

(5:40) AI, Investment, and Talent: evaluating AI spending, automation, hiring decisions, and whether technology is actually improving the business

(6:50) Delaware and the Competition for Corporate Domicile: why DE has historically balanced the interests of investors and management

(9:33) Long-Term Leadership: why directors should consider more than the immediate political or market environment when making governance decisions. Impact of climate change.

(12:57) AI, Energy, and Corporate Responsibility: data centers, energy and water consumption, environmental impact, and the broader costs of AI. "I think it's a very scary time."

(23:25) Public Benefit Corporations: how the Delaware PBC structure works and why companies like OpenAI and Anthropic are experimenting with new governance models

(24:20) Purpose vs. Branding: why benefit corporations can create useful governance flexibility, but only if companies are willing to stand behind measurable commitments

(27:19) What Good Corporate Citizenship Looks Like: responsibilities to customers, employees, communities, the environment, and the broader workforce

(29:19) Boards, Workers, and Economic Opportunity: why boards should understand the workforce beyond executive compensation and how business can help reduce economic anxiety

(31:02) The Growth of Private Markets: venture capital, private equity, accredited-investor exemptions, and the accountability gap between public and private companies 

(34:25) Disclosure and Market Trust: why SEC reporting, fiduciary enforcement, and access to reliable information remain strengths of U.S. capital markets. About quarterly reporting.

(36:52) AI Inside the Boardroom: the risks of AI-generated minutes, recording board meetings, transcription, discovery, and two-party consent laws

(37:33) Before Artificial Intelligence, Use Human Intelligence: AI agents, privilege, confidential information, hallucinations, and the importance of verifying AI-generated information 

Leo E. Strine, Jr. is Of Counsel at Wachtell, Lipton, Rosen & Katz and previously served as Chief Justice of the Delaware Supreme Court and Chancellor of the Delaware Court of Chancery.

Recorded at the inaugural Boardroom Governance Summit in Healdsburg, California, on August 27, 2026.

Join us for the next Boardroom Governance Summit, August 25–27, 2027, in Healdsburg, California. Register here.

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.

(00:00) Introduction and about the inaugural Boardroom Governance Summit

(1:59) Collaborative Board Leadership: strengthening collaboration among directors and with management 

(4:36) Moving Beyond Pattern Recognition: shrinking decision windows, comfort with ambiguity, and approaching disruption with a beginner’s mind.

(7:52) Board Focus and the Governance Gap: why more information does not necessarily produce better decisions

(11:30) Navigating AI Regulation: conflicting rules across jurisdictions, practical judgment calls, and focusing on the regulations most relevant to the business.

(13:36) Trust as a Driver of Innovation: why companies cannot wait for regulatory clarity to build trust, and how trusted technology can accelerate adoption.

(15:35) The Board as a Strategic Asset: constructive engagement with management, access to leaders across the company, and adapting committee responsibilities to emerging risks.

(18:00) Scenario Planning and The Art of the Long View: challenging the assumptions behind business plans and deciding where to lead, where to follow, and where to wait.

(19:36) Fiduciary Duties in the AI Era: why these duties remain unchanged, even as directors confront new technologies and risks.

(22:53) AI Policies for Directors: why a board’s AI policy should be tailored to directors’ responsibilities.

(23:30) Mission-Critical Risks and Oversight: revisiting risk priorities, applying an all-of-board approach to AI governance, and allocating responsibilities across committees.

(27:32) Governing the Agentic Enterprise: distinguishing augmentation, automation, and autonomy, with clear boundaries, human override, and accountability.

(31:25) AI Agents and Liability: asking where agents operate, whether their decisions are material to the business, and how responsibility is allocated when something goes wrong.

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Sabastian Niles is President and Chief Legal Officer at Salesforce. 

Jackie Liu is a partner at Morrison & Foerster and serves on the board of CEVA, a Nasdaq-listed company.

Recorded at the inaugural Boardroom Governance Summit in Healdsburg, California, on August 27, 2026.

Join us for the next Boardroom Governance Summit, August 25–27, 2027, in Healdsburg, California. Register here.

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Stay connected with Boardroom Governance:

• Website: boardroom-governance.com
• Newsletter: Boardroom Governance on Substack
• YouTube: Boardroom Governance
• LinkedIn: Evan Epstein
• X: @evanepstein

Subscribe to the Boardroom Governance newsletter for governance insights and exclusive subscriber content: evanepstein.substack.com

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.

(0:00) Intro

(1:28) About the podcast sponsor: The American College of Governance Counsel

(2:12) Start of interview

(3:25) Ryan Nowicki Stewart’s Origin Story

(5:06) The origin of Pennant AI and Ryan’s goal of building a “world model for corporate governance”

(5:21) Why institutional investors struggle to scale governance oversight across thousands of portfolio companies

(7:48) How Proxy Voting Works: annual meetings, shareholder votes, engagement, and why governance decisions can have major financial consequences

(10:28) Proxy Season: why voting is concentrated in the spring in the U.S., but governance engagement is increasingly a year-round and global process

(11:28) Ryan’s decision to join Y Combinator and why a corporate governance startup fit into the YC ecosystem

(15:00) His experience with technology founders and executives perception on current proxy voting system

(15:54) Building a “living, breathing operating system” for governance rather than relying on static reports and PDFs

(18:53) The continuing role of proxy advisors and why institutional investors are looking for alternatives to legacy providers

(24:12) Who Pennant Serves: institutional investors, public companies, and corporate advisors

(25:18) Why Pennant does not publish a house voting policy and instead helps investors implement their own governance frameworks

(29:57) Founder Control, Dual-Class Shares, and Investor Power: the shifting balance among founders, boards, management, and institutional investors. Reference to Stripe's Investor Letter from August 2026 “the Singularity started on 1/1/26”

(30:50) Public and Private Markets Converging: SpaceX, Anthropic, OpenAI, Stripe, and new approaches to ownership and governance. *Reference to E210 with Eric Ries.

(35:20) Global Governance: Japan, the U.K., the U.S., and how shareholder engagement differs across markets. *Reference to E221 with Stavros Gadinis.

(38:40) Y Combinator, OpenAI credits, and why Pennant remains model-agnostic

(39:39) Choosing AI Models for Governance: why different models perform better at different governance tasks

(41:47) Pennant’s Governance Arena: testing how frontier AI models respond to governance questions

(43:33) Pennant after YC Demo Day: new investors, enterprise clients, and plans to grow the company

(45:12) What Ryan wants directors to understand about AI, shareholder engagement, and why technology can create more time for meaningful investor conversations

(46:37) Books that have influenced Ryan:

1. Horrible Histories by Terry Deary (1993-2013)
2. The Thinking Machine by Stephen Witt (2025)
3. Mobilize by Palantir CTO Shyam Sankar and Madeline Hart (2026)

(48:46) His mentors: Stephanie Creary and Abe Friedman (reference to E43 with Abe from 2021)

(50:44) A quote Ryan thinks of often: “Success is not final, failure is not fatal: it is the courage to continue that counts” 

(51:37) An unusual habit: Settlers of Catan. An unusual passion: the Australian Baseball League 

(53:11) The living person he most admires: Angela Merkel, and lessons from her patient, evidence-driven approach to leadership

(54:42) Where to find Pennant AI and follow Ryan’s work

Ryan Nowicki Stewart is the co-founder and CEO of Pennant AI, a Y Combinator-backed governance technology company building AI-powered tools for institutional investors, public companies, and advisors. 

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.

(0:00) Intro

(1:23) About the podcast sponsor: The American College of Governance Counsel

(2:07) Start of interview

(2:58) Stavros Gadinis' Origin Story

(4:27) The origin of his new book Corporate Ordering: How Corporations Navigate Social Conflict

(5:30) Shareholders vs. Stakeholders: why the century-old debate over corporate purpose remains unresolved

(7:37) Corporations as Rulemakers: how companies increasingly create rules that affect millions or even billions of people

(11:07) Who Really Has Decision-Making Power? Boards, founders, dual-class shares, institutional investors, and corporate hierarchies

(13:31) AI Governance Models: Microsoft, OpenAI, Anthropic, and different approaches to governing AI

(14:43) Microsoft’s approach to Responsible AI and building internal systems for accountability, transparency, and oversight

(18:00) Creating internal checks on product decisions and giving employees a process to challenge governance decisions

(18:48) The OpenAI Governance Crisis: Altman’s 2023 firing, the power of employees and investors, and the limits of formal board authority

(20:25) Why governance structures designed for startups may not survive when companies grow into massive global businesses

(22:25) OpenAI vs. Anthropic: detailed rulebooks versus Constitutional AI and the tradeoffs between specific rules and broad principles

(25:09) Meta’s Oversight Board: what worked, what did not, and why independent monitoring requires real authority

(28:10) Stavros’s Three-Part Corporate Ordering Framework: 1) rule making, 2) implementation, and 3) monitoring.

(32:20) Is corporate ordering just Compliance 2.0? Why Stavros sees an important difference between compliance and product design

(34:55) Uber’s Safety Reckoning: how outside consultation changed the company’s approach to reporting sexual assault 

(38:06) AI Regulation: the emerging patchwork across the United States, Europe, China, and other jurisdictions

(40:04) How corporate AI governance practices can eventually become the foundation for government regulation

(42:17) The increasingly important role of the General Counsel in governance, regulation, and helping shape emerging rules

(43:21) A book that influenced Stavros: a biography of Louis XIV, and lessons about concentrated power and decision-making

(44:19) His mentor, Howell Jackson of Harvard Law School, and the importance of embracing complexity

(45:27) A lesson from his painting instructor: don’t be afraid to start with the wrong line

(46:20) An unusual passion: French patisserie 

(46:56) The living person he most admires: Icelandic pianist Víkingur Ólafsson

(48:20) Where to find Corporate Ordering: How Corporations Navigate Social Conflict

Stavros Gadinis is the George R. Johnson Professor of Law and Faculty Director of the Berkeley Center for Law and Business at UC Berkeley School of Law

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Stay connected with Boardroom Governance:

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.

(00:00) Intro and about to the inaugural Boardroom Governance Summit

(02:45) About Ivonne Wassenaar, and Alla Whitston from MUFG

(04:51) AI and Board Oversight: what directors should be asking as AI moves from experimentation into core business strategy

(05:59) Looking Beyond Today’s AI: why boards need outside perspectives on startups, venture investment, and where the technology may be heading next.

(06:58) Building Optionality: avoiding long-term technology lock-in while models, infrastructure, and token economics are changing rapidly

(07:18) AI and Cybersecurity: how AI is accelerating attacks and why boards should be conducting cyber tabletop exercises with management

(08:39) Data Governance and AI: protecting company and customer data and preventing sensitive information from being used to train outside models

(10:21) AI Regulation: why stronger and more consistent regulatory guardrails may actually help companies manage risk

(13:24) What Directors Should Ask the CIO: data architecture, AI infrastructure, controls, third-party assessments, and protecting the company’s “crown jewels”

(16:34) The AI Venture Boom (the "psychotic edge"): why investors acknowledge they may be overpaying but still fear missing the eventual winners

(18:20) Separating AI Hype from Durable Businesses: customer problems, competitive moats, proprietary data, gross margins, and sustainable unit economics

(19:50) Global AI Competition: U.S., Chinese, European, and Japanese models and the importance of avoiding dependence on any single provider

(23:11) AI and the Workforce: how AI is changing engineering, sales, marketing, and other functions inside companies

(24:40) Headcount Dollars vs. Token Dollars: how companies are reallocating budgets as AI becomes part of everyday operations

(26:15) Citizen Development: why AI is democratizing software development and allowing business users to build their own tools and agents

(28:48) How Boards Should Think About AI Budgets: experimentation, large strategic bets, acquisitions, and holding management accountable to the original business case. "The sure path to death is to not do AI"

(32:39) Recommendation to boards: "[W]hen you think about AI, think about not necessarily your straight ROI case or your cost case. Think about what am I trying to achieve in the next six to 12 months? And that's literally as far as you can see, and it's probably closer to six." When to Shut Down AI Projects: why boards need discipline around stopping experiments that are not producing results.

(33:30) Beyond Productivity: moving from cost savings and efficiency to true value realization through faster decisions, autonomy, and new business opportunities

Ivonne Wassenaar is a technology executive, advisor, and experienced board director whose career spans software, strategy consulting, and CEO roles. She currently serves on boards across public, private equity, and venture-backed companies.

Alla Whitston is CIO for MUFG Americas and brings more than three decades of experience leading technology in the financial services industry.

Recorded at the inaugural Boardroom Governance Summit in Healdsburg, California, on August 27, 2026.

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Stay connected with Boardroom Governance:

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.

(0:00) Introduction to the inaugural Boardroom Governance Summit

(02:18) The Board’s Role in CEO Succession: why succession is about more than hiring and firing the CEO, and why boards should think about the entire executive management team

(04:57) Is the CEO You Have Today the CEO You Need Tomorrow? How rapid changes in markets, technology, and industry can change the leadership profile a company needs

(06:31) Why Succession Plans Fail: boards know succession is important, so why are so many still unprepared?

(07:54) Succession as an Ongoing Process: why the conversation should begin on the first day of a CEO’s tenure

(09:23) The Emotion of CEO Succession: ego, fear, trust, and why succession can become one of the most difficult conversations between a board and a CEO

(11:14) Who Owns CEO Succession? The role of the board chair, Nom/Gov Committee, Comp Committee, and other board leaders

(13:24) Developing Internal Candidates: how directors can build relationships with senior executives and assess whether they could realistically become CEO

(14:57) The P&L Test: if operating experience is essential for the next CEO, boards need to create those development opportunities years in advance

(17:53) Private Equity and CEO Succession: the influence of investment horizons, exit expectations, and the private equity sponsor

(19:24) Family-Owned Companies: long-term ownership, outside CEOs, independent boards, and succession across generations

(20:41) Venture-Backed Companies: what happens when investors have backed the founder but the founder may no longer be the right CEO to scale the company

(22:47) Founder Control and Dual-Class Shares: the limits of board influence when founders retain voting control

(24:56) Shareholder Activism: why activists often target CEO performance through the board and how directors should assess their own vulnerabilities

(28:00) AI and the Next Generation of CEOs: why intellectual curiosity, adaptability, and the willingness to learn may matter more than claiming to be an AI expert

(30:06) How AI, geopolitics, and accelerating change are reshaping the qualities boards should look for in CEOs

Karen Francis DeGolia is a board member at Vontier, CelLink, and NAUTO. Penny Herscher is a board member at Lumentum, Penguin Solutions, Forvia SA, and Modern Health.

This conversation was recorded at the inaugural Boardroom Governance Summit in Healdsburg, California, on August 26–27, 2026.

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Stay connected with Boardroom Governance:

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.

(0:00) Thank you to everyone who joined the inaugural Boardroom Governance Summit

(0:30) Intro

(1:51) About the podcast sponsor: The American College of Governance Counsel

(2:38) Start of interview

(3:21) Raffaela Rein’s Origin Story

(4:44) Rocket Internet: the “copycat factory,” global expansion, execution, and leadership lessons

(8:36) Founding and selling CareerFoundry

(9:16) Raffaela’s Board Journey: Porsche and other boards: PE, tech unicorn, startups and non-profits.

(11:04) Why she founded BoardLens

(15:00) AI as a Strategic Sparring Partner for board members: better preparation, sharper questions, and challenging assumptions

(16:14) How BoardLens is different from a traditional board portal and why individual directors are adopting it

(18:37) Confidentiality, Privilege, and AI: the risks of using public AI tools for board work

(21:03) The AI models behind BoardLens: Anthropic, Gemini, and OpenAI

(23:25) Open vs. Closed AI Models and balancing performance, security, and confidentiality

(25:01) BoardLens users and the growing demand for AI in regulated industries

(26:37) The “private equitization” of the economy and the rise of private-company boards

(31:38) OpenAI, Anthropic, and New Governance Models: PBCs, nonprofits, trusts, and mission-driven governance

(35:15) The Sam Altman episode and the unusual balance of power among boards, employees, and investors

(36:34) Mission vs. Financial Interests in AI governance

(37:47) Founder Control and Dual-Class Shares: SpaceX, Elon Musk, and investor willingness to accept unconventional governance

(39:17) The Porsche IPO and other unconventional governance structures

(41:07) U.S. vs. German Boards: comparing the single-board and two-tier governance models

(44:00) Why the board meeting should be one of the most valuable meetings in the company, not simply a reporting exercise

(44:40) Why Raffaela believes the AI transformation may be bigger than the digital transformation

(45:36) AI Strategy and Governance education for directors

(46:00) Building a Directors Council to think about the future of board work in an AI-driven world

(47:44) Autonomous vehicles, disruption of the German and European auto industries, and global competition

(48:15) What happens if AI makes many goods and services dramatically cheaper, or even effectively free?

(49:04) Books that have greatly influenced her life:

(51:13) Her mentors and the people she admires for perseverance

(52:12) Quotes she thinks of often: Invictus and “I am the master of my fate, I am the captain of my soul.”

(52:54) An unusual habit: going through different color phases

(53:56) The living person she most admires: Tony Robbins, and his ability to sustain a sense of purpose over decades

Raffaela Rein is the CEO and founder of BoardLens, an AI-powered intelligence platform built for board members. Her career spans BlackRock, Rocket Internet, entrepreneurship, and corporate boards. 

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Stay connected with Boardroom Governance:

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Subscribe to the Boardroom Governance newsletter for governance insights and exclusive subscriber content: evanepstein.substack.com

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.

(0:00) Thank you to all participants of the Boardroom Governance Summit (Aug 26-27, 2026) 

(0:16) Intro *Boardroom Governance YouTube Channel launch.

(1:45) About the podcast sponsor: The American College of Governance Counsel.

(2:31) Start of interview. 

(3:25) Origin Story of Marc Huffman

(6:26) About OnBoard

(10:35) AI Risks for SaaS and OnBoard

(12:46) Directors Using AI in Shadows. His ideal board books.

(17:05) Building a Better AI Policy

(20:44) Agentic AI for Boards. Semantics search inside the board portal.

(23:30) Recording Risks in Meetings

(27:34) Improving Board Effectiveness

(29:44) Public, Private, and Governance

(32:50) The Private Markets Shift

(37:37) AI and Board Dynamics. Empowering Independent Directors.

(41:40) Semantic Search and Governance IQ Breakthrough (institutional memory).

(44:15) Models, Costs, and Trust

(47:26) Book that has greatly influenced his life: Shantaram, by Gregory David Roberts (2003)

(48:17) His mentors

(49:22) Quotes that he thinks of often or lives his life by "I'm a product of my own expectations"

(49:43) An unusual habit or an absurd thing that he loves. 

(50:35) The living person he most admires.

Marc Huffman is the CEO of OnBoard, a global leader in digital board governance solutions, serving over 6,000 boards worldwide.

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Stay connected with Boardroom Governance:

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Subscribe to the Boardroom Governance newsletter for governance insights and exclusive subscriber content: evanepstein.substack.com

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.

(0:00) About the Boardroom Governance Summit (Aug 26-27, 2026) 

(0:43) Intro

(2:08) About the podcast sponsor: The American College of Governance Counsel.

(2:54) Start of interview. 

(3:56) Origin Story of Shannon Nash

(7:00) Her pivot from Law to Finance

(9:15) Her operating and finance career 

(12:55) Her experience in tech (subscription businesses) and current COO and CFO role at Vibrant Planet

(15:50) Her first board (UserTesting) and subsequent board career (Netscout, SoFi, Lazy Dog Restaurants, Silicon Valley Community Foundation) 

(22:04) Cybersecurity Meets AI

(28:47) Where are the Humans? The next wave in the agentic era

(31:44) Regulated Boards and Risk

(36:25) Private Board Experience (VC and PE). 

(41:13) About Alpha AI, focusing on AI Governance

(43:53) On her podcast No Boxes, Just Verses

(46:45) Her obsession with the Acquired podcast

(47:41) Her mentors

(49:40) Quotes that she thinks of often or lives her life by.

(51:06) An unusual habit or an absurd thing that she loves. Beat Shazam show

(52:15) The living person she most admires.

Shannon Nash is a qualified financial expert, attorney, and CPA with over 30 years at the intersection of technology, finance, and governance. She serves as a board member in both public and private companies.

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Stay connected with Boardroom Governance:

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Music: “Seeing The Future” by Dexter Britain, via Free Music Archive, licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License.