Boardroom Governance with Evan Epstein

(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
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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:
Horrible Histories by Terry Deary (1993-2013)
The Thinking Machine by Stephen Witt (2025)
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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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
(1:23) 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:
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.

(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:
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) 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:
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.