The Transaction Abstract Podcast

From Searcher to Operator to Investor: Lessons in Ownership


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In this episode of The Transaction Abstract Podcast, Redpath's Joe Hellman sat down with Rob Cherun, founder and managing partner of Legate Partners, to talk about what ownership really requires and how the search journey shapes better operators and investors.

Drawing from his experience building and scaling a business to nearly 2,000 employees before exiting and returning as an investor, Rob shares how grit, accountability, and hands-on leadership define long-term success far more than credentials or deal structure.

In this episode, you'll hear insights on:

  • Why ownership is a long-term commitment, not a shortcut
  • What investors really look for beyond resumes and industry experience
  • How grit and emotional durability separate strong operators from the rest
  • Why the entrepreneur matters as much as the asset in any deal
  • How alignment and trust shape better partnerships between operators and investors

Listen to the full episode of The Transaction Abstract Podcast to hear Rob's real-world perspective on search, ownership, investing, and what it truly takes to succeed.

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The Transaction Abstract PodcastBy Redpath and Company