Why Self-Funded Search Is Harder Now and How to Stand Out as a Business Buyer

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:

(00:00:00) - Intro

(00:02:32) - Introducing Jacob

(00:04:14) - Jacob's path from operations to investing