In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo sit down with Mike Botkin for a wide-ranging conversation on operator mindset, capital alignment, and what it really takes to build and scale small businesses. Drawing from his experience growing a tiny landscaping company into one of the largest in the Southeast, Mike shares hard-earned lessons on choosing partners, knowing when to stay in the CEO seat, and why not all growth paths are created equal. The discussion blends candid reflections on leadership, stress, and lifestyle tradeoffs with tactical insights on capital structures and service business economics.

They discuss:

Why underwriting the operator matters as much as underwriting the business
The realities of giving up the CEO role and when it backfires
How capital partner incentives shape decisions in both good and bad times
The differences between residential and commercial services from an operator's perspective
When turnarounds and small businesses can outperform larger, more polished deals

Links:

Mike on X - ⁠https://x.com/MikeBotkin_⁠

Mike's website - ⁠https://botkinhq.com/⁠

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

Sam on X - ⁠https://x.com/Sam_Rosati⁠

Topics:

(00:00:00) - Intro (00:00:55) - Introducing the guest: Mike Botkin (00:06:23) - Mike's journey in the landscaping business (00:17:35) - Challenges of being a CEO (00:23:26) - Finding the right role: operator vs. advisor (00:36:04) - The value of turnarounds and small business investments (00...