In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati explore the concept of time prioritization and how small business owners can focus on non-urgent but important tasks to drive long-term success. They frame the conversation around the Eisenhower Matrix, examining how founders often get stuck in reactive decision-making and struggle to create space for deeper work.

Kaustubh shares specific examples from running Blooma Tree Experts, including how written scopes of work, real estate planning, and lead attribution have impacted operations. Sam and Kaustubh also dive into how to build organizational trust, encourage team accountability, and design business systems that reward consistent, strategic effort—rather than firefighting.

They also discuss:

• Why task repetition builds a strong accountability culture over time

• How new service lines like tree healthcare create stickier customer relationships

• The limits of capital and people in high-leverage small businesses

• Mental models for hiring, equipment investment, and lease decisions

• The role of consistency, presence, and humility in earning team respect

• How a fitness challenge turned into a real-time case study in incentive design

This episode blends tactical insight with personal reflection, offering a grounded look at how owners can lead intentionally—one week, one system, and one habit at a time.

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

(00:01:49) - The Eisenhower Matrix

(00:04:36) - Applying the EM to Blooma

(00:13:55) - Generating trust with teams

(00:21:03) - What investments do you want to make but lack people/capital? How are you going to solve that?

(00:27:08) - Kaustubh’s decision to pursue different revenue channels and non-linear growth

(00:36:52) - Updates on the fitness competition

In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati unpack the concept of personal non-negotiables and what it takes to make business ownership sustainable over the long haul. What begins as a reflection on physical health quickly evolves into a broader conversation about habit formation, time prioritization, and the limits of willpower.

Kaustubh shares his recent experience becoming a certified arborist while leading Blooma Tree Experts. The two reflect on the difference between project-based discipline and long-term personal routines. Together, they explore a healthy operating rhythm for owners who want to stay in the game for years, not just quarters.

They also discuss:

• Why many business owners neglect their physical health despite having time

• The difference between startup energy and long-term operational sustainability

• How habit stacking and decision fatigue shape daily behavior

• Building accountability through competition and peer support

• Designing boundaries around work, family, and wellness

• How ownership allows for time control but requires discipline to use it well

This episode is a candid, tactical look at the intersection of personal growth and business responsibility, perfect for any owner working to align their health, habits, and leadership.

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

(00:01:12) - Catching up

(00:04:39) - Buying businesses where certification is required to operate them

(00:10:45) - Personal and Professional Non-Negotiables

(00:14:17) - Making physical fitness a priority

(00:29:50) - Creating a competition for fitness

(00:34:03) - Tactical Tips: What Sam and Kaustubh keep in their golf bags

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