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From Operator to Investor: Lessons from Both Sides of the Table

05.29.2026 | Duration: 27:50

A founder-to-investor perspective on navigating growth, leadership, and evolving market dynamics.

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Podcast Overview

What does the journey from building a company to funding one really look like? In this episode of the Privately Speaking podcast, KPMG partner and podcast host, Erika Whitmore, sits down with Kat Kennedy, General Partner at Kickstart Fund, who has seen it all. From her beginnings as a software developer and startup president to her current role as a venture capitalist, Kat shares practical insights into the realities of scaling a business.

Join us for a candid conversation about what investors truly look for beyond the pitch deck and the critical mindset shifts required at every stage of the entrepreneurial journey.

This episode offers actionable insights for private company leaders, including:

  • Embracing the "dumpster fire": Why moments of chaos are not just normal, but essential for growth.
  • Beyond the pitch deck: What investors are truly looking for in a founding team.
  • The scaling journey: How to evolve your role and team as your company grows from one stage to the next.

If you're leading a private company through the challenges of growth, this is a conversation you won't want to miss.

Meet our podcast team

Image of Erika R. Whitmore
Erika R. Whitmore
Office Managing Partner, Audit, KPMG US

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