Sam Rosati and Kaustubh Deo dive into the realities of small business ownership, exploring the tension between working in the business versus working on it. They share firsthand experiences from recent projects, unpack the challenges of scaling into larger, more complex jobs, and reflect on how owner involvement shapes day-to-day operations. The conversation offers a candid look at the trade-offs entrepreneurs face when balancing growth ambitions with operational realities.

We discuss:

• Lessons from moving between residential and commercial projects

• The role of owner dependency and how to assess it in acquisitions

• Defining the difference between working in versus on the business

• The importance of lead generation and long-term customer value

• Why strong operators are often more critical than capital or deals

This episode provides practical insights for entrepreneurs navigating the complexities of ownership and growth.

Support our Sponsors:

Kalmar Group

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, [email protected]) 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

Follow along with the guys' fitness tracker! - https://bit.ly/3T4EpHw

Topics:

(00:00:00) - Intro (00:01:05) - Challenges of large-scale projects (00:01:59) - Daily operations and coordination (00:07:29) - Commercial vs. residential jobs (00:17:56) - Working on vs. in the business (00:27:23) - Evaluating business relationships (00:29:03) - Understanding owner dependence (00:31:54) - Case study: Seller separation (00:33:15) - Challenges of owner dependence (00:33:55) - The role of technical expertise (00:38:16) - Managing customer complaints (00:40:41) - Lead generation strategies (00:52:23) - Reflections on search partnerships (00:56:20) - Conclusion and final thoughts