30. Guest Ira Weiss on Boardroom Strategy, Leadership Fit, and the Power of Persistence
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30. Guest Ira Weiss on Boardroom Strategy, Leadership Fit, and the Power of Persistence
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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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