Ryan Nowicki Stewart, co-founder and CEO of Pennant AI, joins the Boardroom Governance Podcast to discuss how AI is changing proxy voting, shareholder engagement, and institutional investor stewardship. We also discuss proxy advisors, Y Combinator, founder control, the convergence of public and private markets, emerging governance structures at companies like OpenAI and Anthropic, and why human judgment remains critical as investors adopt AI-powered governance tools.
(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:
(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.