In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati respond to a powerful message from a fellow operator grappling with the emotional side of small business ownership—specifically the gap between success on paper and fulfillment in real life. What unfolds is one of their most candid conversations yet, tackling everything from burnout and routines to long-term sustainability in the seat.

They unpack how the day-to-day grind of ownership—especially in the first few years—can leave even thriving operators feeling disoriented or dissatisfied, and why this “arrival fallacy” is so common among searchers and first-time CEOs. Along the way, they explore what it really means to build a business that lasts 10 years, not just three, and how to create systems, habits, and expectations that make that possible.

Key themes include:

• How small business ownership reshapes identity, routines, and personal boundaries

• Why perfectionism and checklist obsession can quietly kill sustainability

• The mental toll of constant decision-making, unpredictability, and false urgency

• Redefining success beyond equity value and financial milestones

• Building in non-negotiables to protect relationships, health, and focus

• Why longevity requires both operational delegation and emotional endurance

If you’re deep in the operating seat—or about to step into it—this episode offers a deeply relatable, tactical conversation about what it actually takes to stay in the game long enough for ownership to be worth it.

 

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   (00:03:30) - Listener Email: The Reality of Business Ownership   (00:05:31) - Challenges of Small Business Ownership   (00:11:09) - Personal Routines and Business Demands   (00:19:19) - Financial Realities: The Long Road to Success   (00:23:43) - Setting Boundaries as a CEO   (00:26:42) - Balancing Family and Work Routines   (00:27:50) - Identity and Habit Formation   (00:29:36) - Negotiating Work and Personal Time   (00:30:30) - The Importance of Disconnecting   (00:32:12) - Weekend Work Strategies   (00:35:46) - Perfectionism vs. Effective Delegation   (00:39:52) - Setting Realistic Expectations   (00:43:13) - Measuring Success and Finding Balance   (00:48:39) - Concluding Thoughts and Reflections