Sam Rosati, Kaustubh Deo, and Jacob Hall explore the evolving challenges of self-funded search on The Intentional Owner. Jacob Hall runs Kando Capital, a minority equity investor focused on self-funded searchers, and teaches entrepreneurship through acquisition at the University of Texas. His operational background includes Fortune 500 turnarounds and firsthand experience uncovering embezzlement in a small business. The conversation addresses how the playbook that worked from 2019 to 2021, max leverage, wide-open geography, hockey stick projections, no longer matches today's market reality. Interest rates have risen, competition has intensified, and buyer awareness has exploded without a corresponding increase in buyer preparedness. They discuss: • Why searchers must define a specific edge rather than treating any quality business as a fit • How emotional intelligence and transparency matter more than credentials when diligencing people • The underestimated difficulty of operating a small business compared to corporate work • Why geographic constraints can become advantages if leveraged through in-person relationship building • The gap between romanticized perceptions of business ownership and the visceral reality of layoffs, cash constraints, and daily firefighting This episode offers a clear-eyed view of search for anyone considering leaving a stable career to buy and operate a small business. Topics: 00:00 - Intro 02:32 - Introducing Jacob 04:14 - Jacob's path from operations to investing 10:26 - How Kando Capital works 11:29 - Deal flow and investment pace 18:00 - Why the old search playbook doesn't work 20:30 - The Four Horsemen of search challenges 27:00 - Running a business is harder than it looks 30:12 - What separates successful searchers 33:30 - The importance of EQ over IQ 35:43 - Diligencing the people side 46:14 - Preparing searchers for reality 51:54 - Finding your edge as a searcher 01:01:23 - Geographic constraints as advantage 01:08:50 - The pep talk for searchers