In this episode of The Intentional Owner, hosts Kaustubh Deo and Sam Rosati explore the realities of long-term ownership in small business. Many entrepreneurs enter the space with the intention of holding a business indefinitely, but the challenges of day-to-day operations, shifting risk tolerance, and unforeseen opportunities often reshape that vision.

Kaustubh shares insights from his own experience running Blooma Tree Services, discussing how his perspective on ownership has evolved over time. He and Sam break down the differences between private equity-style exits and long-term small business ownership, the mental and strategic shifts required to make a business less owner-dependent, and how liquidity preferences shape decision-making for both operators and investors.

Other key takeaways include:

• How small business owners transition from high-risk, high-reward mindsets to long-term stability
• The role of acquisitions in scaling an SMB and creating financial flexibility
• How investors think about liquidity and exit strategies in search fund deals
• The challenges of balancing growth, personal fulfillment, and financial returns

Whether you're a search fund entrepreneur, small business owner, or investor, this episode offers a deep dive into what it truly means to hold a business for the long haul—and why so many owners change course along the way.

 

Links: Kaustubh on LinkedIn - https://www.linkedin.com/in/kaustubh-deo/

Sam on X - https://x.com/Sam_Rosati

 

Topics:

(00:00:00) - Intro

(00:01:36) - Long-term holds

(00:03:00) - PE approaches to long-term holds

(00:08:58) - SMB long-term hold philosophies

(00:17:40) - Accounting for an exit in fnancinal modeling

(00:19:21) - Kaustubh’s thoughts on holding after 3 years in the business

(00:22:31) - Investor philosophies on holding periods

(00:27:30) - Are hold periods even important?

(0:28:20) - Sam’s rollup holding thesis

(00:36:21) - Kaustubh’s thoughts on M&A

(00:43:07) - Strategic planning tools and support groups