Managing Relationships between Investors, Operators, and Searchers - The Intentional Owner #14

In this episode of The Intentional Owner, Kaustubh Deo and Sam Rosati dive deep into the often-overlooked art of managing investors in self-funded search deals. From communication best practices to governance structures, Kaustubh and Sam explore the nuances that define healthy investor relationships. They share personal experiences, trade perspectives as both operators and investors, and offer candid commentary on what it really takes to build trust and discipline in capital partnerships. The conversation also touches on capital structuring, ownership dynamics, and how to thoughtfully balance investor involvement. They also discuss: * Common pitfalls searchers face when managing investor relationships * The difference between defensive deal-making and thoughtful diligence * How investor reporting impacts long-term cost of capital * Trade-offs of working with active vs. passive investors and mini-funds * Real-world insights on liquidity rights, put/call structures, and governance A must-listen for searchers and owners seeking to build disciplined, long-term relationships with capital partners. Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first Sam on X - https://x.com/Sam_Rosati Follow along with the guys' fitness tracker! - https://bit.ly/3T4EpHw Topics: (00:00:00) - Intro (00:01:05) - Recapping the week (00:16:00) - Kaustub's investor set up (00:20:32) - Passive vs. active investors (00:30:41) - Liquidity rights (00:39:19) - What is the "right" check size? (00:43:06) - Sam's investing style (00:45:35) - Board philosophies (00:48;19) - Types of People who can be useful to searchers as investors (00:51:09) - Tactical tip of the week