In this episode of The Intentional Owner, Kaustubh Deo and Sam Rosati dive deep into the often-overlooked art of managing investors in self-funded search deals. From communication best practices to governance structures, Kaustubh and Sam explore the nuances that define healthy investor relationships. They share personal experiences, trade perspectives as both operators and investors, and offer candid commentary on what it really takes to build trust and discipline in capital partnerships. The conversation also touches on capital structuring, ownership dynamics, and how to thoughtfully balance investor involvement.

They also discuss:

* Common pitfalls searchers face when managing investor relationships

* The difference between defensive deal-making and thoughtful diligence

* How investor reporting impacts long-term cost of capital

* Trade-offs of working with active vs. passive investors and mini-funds

* Real-world insights on liquidity rights, put/call structures, and governance

A must-listen for searchers and owners seeking to build disciplined, long-term relationships with capital partners.

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) - Recapping the week

(00:16:00) - Kaustub's investor set up

(00:20:32) - Passive vs. active investors

(00:30:41) - Liquidity rights

(00:39:19) - What is the "right" check size?

(00:43:06) - Sam's investing style

(00:45:35) - Board philosophies

(00:48;19) - Types of People who can be useful to searchers as investors

(00:51:09) - Tactical tip of the week

Quick Update for the listeners! We're excited to announce that we will soon be bringing guests onto the show, as well as moving to a release cadence of every other week. See you next Thursday!

In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati unpack what it looks like to build a fulfilling life around small business ownership without sacrificing long-term goals. Framed around personal goal setting, competing priorities, and everyday tradeoffs, the episode offers a candid look at how both hosts are trying to design lives that support sustainability—not just scale.

They share stories of recent chaos, from moving mishaps and work-life boundaries to surprise break-ins and activity trackers, all while reflecting on how much structure is enough to keep life moving forward without being overly rigid.

They also discuss:

• The tension between goal-setting and adaptability in both life and business

• How to balance ambition with long-term personal sustainability

• Frameworks like EOS and the Vision Traction Organizer for business planning

• The opportunity cost of hobbies and how personal priorities evolve with family

• Leveraging tools like KPI dashboards and Google Sheets for operational clarity

• The importance of community, fitness, and calendaring for intentional living

This episode is a thoughtful, unfiltered conversation for anyone navigating the overlap between business ownership, relationships, and building a meaningful life—one decision at a time.

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Topics:

(00:00:00) - Intro

(00:01:08) - Catching up

(00:14:39) - Setting meaningful goals

(00:20:34) - BHAGs

(00:22:47) - M&A Approaches

(00:26:53) - Goal setting at Blooma and at home

(00:33:48) - Maintaing friendships

(00:45:35) - Living with a long-distance SO

(00:48:50) - Priority tradeoffs

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

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

In this special live episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati take the stage at SMBash in Dallas for a wide-ranging, honest, and often humorous conversation with two operators who've taken very different paths into small business ownership.

First up is Chris Williams, owner of System Six, who shares how he transitioned from investment banking and private equity to running a remote bookkeeping and finance operations firm. Chris opens up about the real motivations that led him to entrepreneurship, the challenges of stepping into the CEO role, and how becoming a new father has shaped his perspective on work-life balance, time management, and the long game of ownership.

Later in the episode, they're joined by Jeff Driskel, a current NFL quarterback and co-founder of Four Pillars Group, an independent sponsor platform. Jeff talks about balancing pro football with building a portfolio of small businesses, the surprising overlap between athletics and entrepreneurship, and what it's been like running a company alongside his brother. He also shares lessons on discipline, learning new systems, and how he's using the trust he's built in the locker room to raise capital and source operators.

This episode covers:

• Why people choose the small business path—and how that motivation evolves
• The highs and lows of parenting while owning and growing a business
• Building companies with family and managing partnership dynamics
• Operator-first investing and how to find the right fit between people and businesses
• The importance of long-term thinking, pattern recognition, and staying power in ETA

Recorded live, this conversation blends real stories, practical advice, and a behind-the-scenes look at what it truly means to build a life—and a business—with intention.

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

(00:01:23) - Chris Williams' journey and motivations

(00:05:15) - Balancing business and personal life

(00:17:28) - Jeff Driscoll's background and transition to ETA

(00:21:49) - The secret sauce to success

(00:21:58) - Transitioning from football to business

(00:24:24) - Working with family

(00:25:19) - Choosing the right business

(00:27:46) - Finding the right people

(00:31:05) - Leveraging football for business success

(00:34:44) - Lessons from football

(00:40:46) - Adapting to new teams and systems

In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati unpack one of the most important and nuanced decisions a small business buyer can make: whether to self-fund and retain 100% ownership or raise equity from outside investors.

Drawing from their own experiences and those of other operators, Kaustubh and Sam explore how this decision impacts governance, financial flexibility, and long-term strategy. They get into the real trade-offs between maximizing ownership and building in room to breathe—especially when it comes to leverage, personal guarantees, and navigating the stress of early-stage operations.

They also dive into:

• How much control investors should have—and where to draw the line
• The importance of aligning investor involvement with expectations up front
• Building informal and formal support systems around the CEO
• What makes an ideal investor profile and cap table structure
• How investor communication and transparency affect outcomes
• Why having the ability to sell—or step back—should always remain with the operator

This episode is full of practical advice for searchers, operators, and investors who want to better understand the dynamics behind ownership structure, investor relationships, and long-term alignment.

Links:

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Topics:

(00:00) - Intro

(00:01:30) - Catching up after vacation

(00:11:21) - Self-funding vs. Raising money in acquiring businesses

(00:18:00) - The pros of owning 100% of a business

(00:23:28) - Advisory boards

(00:24:48) - Is there a "right" number or mix of investors?

(00;27:35) - Finding mentors

(00:30:11) - Paying for consulting

(00:33:01) - Investor mindset towards returns

(00:39:53) - Investor communication

(00:49:38) - Governance

(00:56:34) - Should a Searcher be able to do work outside of the business they just bought?

(00:59:07) - If you could only choose one profile of investor, what would the ideal be?