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

In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati dive into one of the most misunderstood yet critical concepts in small business ownership: Debt Service Coverage Ratio, or DSCR. Drawing from Kaustubh’s experience running Blooma Tree Services and Sam’s ongoing involvement with operators and investors across the ETA community, the discussion unpacks how DSCR directly affects an owner’s ability to invest, grow, and sleep at night.

They break down what DSCR really means—not just in theory, but in the everyday cash flow decisions operators face. Whether it's hiring a new team member, buying equipment, or weathering seasonal slowdowns, Kaustubh and Sam explain how even well-capitalized businesses can find themselves squeezed when the math on debt coverage gets too tight.

Other key insights include:

• How DSCR impacts hiring timelines, capex decisions, and strategic flexibility

• Real-world frameworks for understanding payroll, margins, and revenue mix

• The tradeoffs of financing with SBA debt and how to build in early breathing room

• Why many operators underestimate cash volatility even in profitable businesses

• Strategies for aligning long-term vision with the financial realities of leverage

This episode is a must-listen for anyone currently running a small business—or planning to buy one—who wants to avoid being blindsided by the very structure that made their acquisition possible. It’s a candid, tactical, and grounded conversation about what it really means to operate within financial constraints.

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

(00:01:05) - Tax day For SMB and ETA folks

(00:04:42) - Podcast origins

(00:07:26) - Is SMB just micro-PE?

(00:09:38) - What Searchers are hoping to get out of ETA and SMB

(00:18:08) - The growing interest of PE in tree-care

(00:26:04) - Kaustub’s intentions with Blooma

(00:32:49) - DSCR issues in SMB

(00:42:28) - Staying involved in the search community post-acquisition

(00:46:06) - Investing in Searchers

In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati reconnect after a busy stretch that included SMBash and the Masters to reflect on what made this year’s event the best one yet. They dive into the evolution of SMBash, from its scrappy beginnings during the pandemic to a thoughtfully curated gathering that now draws operators, searchers, and investors from across the country.

Kaustubh and Sam discuss what’s changed about the event, why the mix of attendees felt refreshingly diverse, and how the conference has become a cornerstone for the ETA community. They reflect on standout keynotes from voices like Brent Beshore and Moses Kagan, lessons from building community outside of business, and the value of stepping outside your industry to gain perspective.

Also in this episode:

• Behind-the-scenes of organizing SMBash and why it continues each year

• The tension between being too in the weeds vs. too far removed as an operator

• How Kaustubh applies lessons from peer groups in other industries to Blooma Tree Services

• The challenge of managing growth, KPIs, and people when scaling a small business

• Why community building in SMB often fills the role of religion or tribe for many entrepreneurs

• A discussion on shared services, equity incentives, and decentralization in holdco structures

This episode blends event recap with personal insight, practical lessons, and a candid look at the realities of operating and building in the world of small business.

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

(00:01:07) - The Masters

(00:09:16) - SMBash recap

(00:20:11) - Why Kaustubh joins national organizations

(00:24:13) - Does being in the weeds to much take away from working “on” the business?

(00:27:13) - Recapping Kaustubh’s KPI Presentation

(00:31:55) - How to improve SMBash

(00:36:21) - Why do you go to SMBash?

(00:38:15) - Wishlist for SMBash 2026

(00:42:21) - Dealing with Tax returns