Episode #222
Ryan Nowicki Stewart (CEO, Pennant AI): AI, Proxy Voting, and the Future of Governance
(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. --- 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 --- Music: “Seeing The Future” by Dexter Britain , via Free Music Archive , licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 United States License .
