EPISODE · Nov 26, 2025 · 30 MIN
250 Board Meetings Later: This CEO’s playbook will change your board meetings forever
from Executives Unplugged · host Keith Cowing
Matt Blumberg reveals why he bans slides, forces independent directors to audition for a seat, and uses AI to simulate Steve Jobs in the boardroom.For many founders, the board meeting is a dreaded time sink full of status updates and glazed eyes. In this episode Matt Blumberg, the CEO of Markup AI and author of Startup Boards, breaks down how to turn your board meetings into your ultimate strategy session. Matt shares the story of a "perfect" board candidate who failed a live audition, the "Rule of Ones" that will lead to an effective board composition, and why he strictly forbids slides during meetings.He also reveals a new experiment: using AI agents to simulate a "Fantasy Board" meeting with personalities like Steve Jobs and Warren Buffett to stress-test decisions before the real directors show up.Executives will come away with a playbook to stop reporting and start using their board to build the business.Chapters00:00 — The No Slides Rule 02:04 — Turning the eye roll into strategy 03:20 — The Audition: Making directors do the work 06:58 — How to reference check your VCs 08:59 — The "Rule of Ones" for board composition 13:25 — Stop writing 50-page board decks 17:24 — Specific rules for better conversations 20:58 — Inside the Markup AI pivot 23:05 — The "Fantasy Board": Simulating Steve Jobs with AI 26:19 — How to fire a board member 28:17 — Why every CEO should sit on another boardFollow Matt on LinkedIn: https://www.linkedin.com/in/mattblumberg/ShoutoutsStartup Boards: https://www.amazon.com/Startup-Boards-Building-Effective-Directors/dp/111985928XMarkup AI: https://markup.aiFred Wilson: https://avc.xyzMike Collins: https://www.linkedin.com/in/mike-collins-362100/Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Executives Unplugged inner circle: https://kc.coachSubscribe to the show: YouTube — https://www.youtube.com/@kcowing Spotify — https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts — https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263
What this episode covers
Matt Blumberg reveals why he bans slides, forces independent directors to audition for a seat, and uses AI to simulate Steve Jobs in the boardroom.For many founders, the board meeting is a dreaded time sink full of status updates and glazed eyes. In this episode Matt Blumberg, the CEO of Markup AI and author of Startup Boards, breaks down how to turn your board meetings into your ultimate strategy session. Matt shares the story of a "perfect" board candidate who failed a live audition, the "Rule of Ones" that will lead to an effective board composition, and why he strictly forbids slides during meetings.He also reveals a new experiment: using AI agents to simulate a "Fantasy Board" meeting with personalities like Steve Jobs and Warren Buffett to stress-test decisions before the real directors show up.Executives will come away with a playbook to stop reporting and start using their board to build the business.Chapters00:00 — The No Slides Rule 02:04 — Turning the eye roll into strategy 03:20 — The Audition: Making directors do the work 06:58 — How to reference check your VCs 08:59 — The "Rule of Ones" for board composition 13:25 — Stop writing 50-page board decks 17:24 — Specific rules for better conversations 20:58 — Inside the Markup AI pivot 23:05 — The "Fantasy Board": Simulating Steve Jobs with AI 26:19 — How to fire a board member 28:17 — Why every CEO should sit on another boardFollow Matt on LinkedIn: https://www.linkedin.com/in/mattblumberg/ShoutoutsStartup Boards: https://www.amazon.com/Startup-Boards-Building-Effective-Directors/dp/111985928XMarkup AI: https://markup.aiFred Wilson: https://avc.xyzMike Collins: https://www.linkedin.com/in/mike-collins-362100/Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Executives Unplugged inner circle: https://kc.coachSubscribe to the show: YouTube — https://www.youtube.com/@kcowing Spotify — https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts — https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263
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250 Board Meetings Later: This CEO’s playbook will change your board meetings forever
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