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. They 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. Topics: 00:00 - Intro 01:05 - A day in the life: Managing chaos 02:01 - Big jobs and unexpected challenges 02:44 - Activity competition and physical work 03:42 - Equipment issues and problem solving 04:11 - Collaborations and trades 05:32 - Commercial vs. residential projects 07:24 - The complexity of large-scale jobs 09:27 - Balancing operations and project management 18:27 - Working in vs. on the business 28:27 - Ride along insights 29:46 - Customer communication dynamics 32:29 - Owner dependence in small businesses 41:41 - Lead generation strategies 49:28 - Challenges of being an operator 53:49 - Reflections on search partnerships 57:48 - Conclusion and wrap-up