In this episode of The Intentional Owner, co-hosts Sam Rosati and Kaustubh Deo unpack the less talked about realities of search, small business ownership, and operating with leverage. They explore why the search phase feels emotionally taxing yet pales in comparison to the ongoing stress of running a business, especially during year end. The conversation weaves together personal experiences, listener questions, and practical reflections on cash flow, risk tolerance, and the mental load that comes with ownership. Along the way, Sam and Kaustubh frame hard earned lessons that aspiring and current owners often only learn the difficult way.

They discuss: • Why search feels stressful but is easier than running a business with leverage • The cash flow challenges and seasonality pressures that hit small businesses in December • How leverage and personal guarantees shape decision making and risk tolerance • Four key questions every searcher should ask before buying a business • The realities of people management and why incentives do not always drive behavior

Support our Sponsors:

The Kalmar Group is a recruitment firm who partners with small business owners around the nation to find Manager to VP level hires in sales, marketing, operations, and finance across multiple niche industries.

Website: https://www.thekalmargroup.com

Twitter: https://x.com/thesmbrecruiter

LinkedIn: https://www.linkedin.com/in/dylanscroggins/

Aspen HR

Please contact our valued sponsor Aspen HR (www.aspenhr.com, sales@aspenhr.com) for a quote on PEO services and a complimentary HR due diligence assessment

Links:

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

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

Topics:

(00:00:00) - Intro (00:02:00) - Winter break and business challenges (00:05:10) - Holiday season financial struggles (00:08:38) - Housekeeping and upcoming events (00:09:57) - The reality of search and entrepreneurship (00:20:08) - End-of-year financial dynamics (00:26:23) - Managing costs and leveraged business challenges (00:29:31) - Introducing the newsletter: Big deal small business (00:31:24) - Four questions for aspiring searchers (00:32:39) - The personal guarantee dilemma (00:40:01) - Family support and small business ownership (00:44:02) - Running towards or away from a career (00:48:51) - Managing people and business realities (00:56:34) - Final thoughts and newsletter promotion