30. Guest Ira Weiss on Boardroom Strategy, Leadership Fit, and the Power of Persistence
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24:42
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What does a board member really look for in a CEO? What signals competence, and what quietly erodes confidence?
In this episode, Mike and Corey sit down with returning guest Ira Weiss—educator, investor, and longtime board member—to decode the often-misunderstood relationship between boards and founding teams. Drawing from over 60 investments and hundreds of founder interactions, Ira shares how he evaluates early-stage CEOs, the underrated power of persistence and curiosity, and the true markers of success (spoiler: it’s not always the outcome).
They dive into:
How founders can turn board meetings into strategic assets
When and why boards start thinking about leadership changes
The real reason investors push for independent board members
Why transparency—especially from the C-suite—is a signal, not a vulnerability
Whether you're raising your first round or leading a growth-stage company, this episode is a practical guide to working with your board, not just reporting to them.
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Episode 30