The Intentional Owner – Details, episodes & analysis

Welcome to The Intentional Owner, hosted by Sam Rosati & Kaustubh Deo. Sam is a Founder at SMBootcamp, SMB Law Group, SMBash and Pursuant Capital as well as an investor in self-funded Searchers. Kaustubh is the President at Blooma Tree Experts and former analyst at Bain Capital and Associate at Searchlight Capital Partners.

Together, they'll discuss small business operations, acquisitions, and investing through entertaining and insightful stories from their own experiences and those of other small business owners and searchers.

In this inaugural episode of The Intentional Owner, Sam and Kaustubh discuss their transitions from high-pressure corporate careers in law and finance to owning small businesses. They delve into the emotional and practical challenges they faced during their searches, the importance of having a clear 'why,' and how they manage time and productivity as business owners. With personal anecdotes and actionable tips, they aim to provide a candid view into the realities of entrepreneurship and small business ownership.

Links:

Kaustubh on LinkedIn - https://www.linkedin.com/in/kaustubh-deo/

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

Watch this episode on YouTube - https://youtu.be/b2NbK-XP-bM

Topics:

(00:00:00) - Intro

(00:03:06) - The Journey to Small Business Ownership  

(00:06:48) - From Law School to Big Law

(00:14:40) - The Decision to Pursue Entrepreneurship  

(00:19:44) - Launching a Self-Funded Search  

(00:30:10) - Starting the Search for a Business  

(00:31:21) - Defining Roles and Strategies  

(00:32:45) - Balancing Introversion and Leadership  

(00:35:28) - Work-Life Balance and Career Choices  

(00:39:23) - Operational Challenges and Solutions  

(00:44:10) - Time Management and Productivity Tips  

(00:52:21) - The Reality of SMB Ownership  

(00:57:22) - Tactical Tips for Business Owners  

Surviving Search, Closing the Deal, and Scaling a Business for the Long Haul

In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo dive deep into the journey of buying and running a small business—specifically, Kaustubh’s experience acquiring and growing Blooma Tree Services.

Kaustubh shares how his path from private equity to entrepreneurship was shaped by a desire for ownership, control, and long-term equity building. He opens up about the reality of searching for and buying a business, including the setbacks of a failed deal, the learning curve of running a trades business, and the unexpected challenges of owner dependency in a company where the sellers were still climbing trees daily.

Other key insights include:

• What it’s really like to transition into an owner-operator role
• The importance of hiring and structuring a team post-acquisition
• Navigating the growing pains of shifting from survival mode to scaling
• Why location and community connections matter more than you think

Whether you’re considering entrepreneurship through acquisition or are in the trenches of running a small business, this episode is packed with real-world lessons from an owner who’s lived it firsthand.

Links:

Kaustubh on LinkedIn - https://www.linkedin.com/in/kaustubh-deo/

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

Topics:

(00:00:00) - Intro

(00:02:03) - Kaustubh’s journey to ETA

(00:13:50) - Going under LOI on a business and losing it

(00:20:39) - Expectations vs. Reality in the day to day of running an acquired business

(00:27:53) - Discovering owner dependency

(00:32:21) - The importance of control in ETA

(00:35:19) - The Whack-a-Mole method

(00:40:47) - Sustainability is a false pretense early in ownership

(00:46:17) - Life owning a small business in your hometown

(00:52:37) - Tactical tips

In this episode of The Intentional Owner, hosts Kaustubh Deo and Sam Rosati dive into what it truly takes to succeed as a small business owner. They break down the mindset, attributes, and leadership qualities that make the difference between thriving in SMB ownership and struggling under its demands.

Kaustubh shares lessons from running Blooma Tree Services, including the reality of transitioning from finance and private equity to operating a blue-collar business. He and Sam discuss the challenges of managing people, the importance of financial understanding, and the surprising role of vendor relationships in long-term success.

Other key takeaways include:

• How to prioritize tasks when you’re wearing multiple hats
• Why revenue generation is the biggest challenge for new SMB owners
• The difference between high IQ and high EQ leadership in small business
• How to leverage vendors and suppliers as true business partners

If you’re considering entrepreneurship through acquisition or already in the trenches of SMB ownership, this episode is packed with real-world insights and hard-earned lessons.

Links:

Kaustubh on LinkedIn - https://www.linkedin.com/in/kaustubh-deo/

Sam on X - https://x.com/Sam_Rosati

Topics:

(00:00:00) - Intro

(00:03:18) - Weekly recap

(00:10:04) - How it feels right before you sign your first deal

(00:14:22) - How to know if you’re ready to take over a business

(00:20:20) - Getting your arms around the numbers

(00:29:07) - What Sam looks for in a Searcher

(00:35:32) - Managing perfectionism in Search

(00:39:18) - Attributes in people that ensure you won’t be successful in Search

(00:43:50) - Prioritization philosophies

(00:56:48) - Tactical Tip - Building vendor/supplier relationships

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?

In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati dive into a topic that rarely gets the spotlight in small business ownership: how running a company impacts your personal relationships, especially with spouses and children.

Through honest, personal reflections, Kaustubh and Sam explore how owning and operating a small business affects everything from daily routines and communication habits to financial risk tolerance and mental health. They discuss the early sacrifices, time constraints, and emotional toll that come with entrepreneurship—and how those pressures can ripple through a family if not managed intentionally.

They also share:

• How boundaries around time, work, and presence evolve over the ownership journey

• Ways to stay aligned with your partner through better communication and regular check-ins

• The reality of raising kids while running a business

• Lessons learned from missed moments, personal resets, and building structure at home

• Tactical advice for maintaining clarity with your spouse when navigating financial risk, investor conversations, and growth decisions

This episode is less about answers and more about starting the conversation. If you’re building a business while trying to be a present partner or parent—or plan to someday—this one is full of real-world perspective and practical takeaways.

Links:

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

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

Topics:

(00:00) - Intro

(00:02:00) - Weekly recap

(0:07:19) - How SMB ownership impacts spouses and children

(00:25:30) - Conversations to have with spouses as Searchers

(00:33:20) - Financial involvement from spouses

(00:33:49) - Marriage and family planning in SMB ownership

(00:44:50) - Home success assessments

(00:48:21) - Children

(00:56:28) - Tactical tip: how searchers should reach out to investors

In this episode of The Intentional Owner, hosts Kaustubh Deo and Sam Rosati explore the realities of long-term ownership in small business. Many entrepreneurs enter the space with the intention of holding a business indefinitely, but the challenges of day-to-day operations, shifting risk tolerance, and unforeseen opportunities often reshape that vision.

Kaustubh shares insights from his own experience running Blooma Tree Services, discussing how his perspective on ownership has evolved over time. He and Sam break down the differences between private equity-style exits and long-term small business ownership, the mental and strategic shifts required to make a business less owner-dependent, and how liquidity preferences shape decision-making for both operators and investors.

Other key takeaways include:

• How small business owners transition from high-risk, high-reward mindsets to long-term stability
• The role of acquisitions in scaling an SMB and creating financial flexibility
• How investors think about liquidity and exit strategies in search fund deals
• The challenges of balancing growth, personal fulfillment, and financial returns

Whether you're a search fund entrepreneur, small business owner, or investor, this episode offers a deep dive into what it truly means to hold a business for the long haul—and why so many owners change course along the way.

Links: Kaustubh on LinkedIn - https://www.linkedin.com/in/kaustubh-deo/

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

Topics:

(00:00:00) - Intro

(00:01:36) - Long-term holds

(00:03:00) - PE approaches to long-term holds

(00:08:58) - SMB long-term hold philosophies

(00:17:40) - Accounting for an exit in fnancinal modeling

(00:19:21) - Kaustubh’s thoughts on holding after 3 years in the business

(00:22:31) - Investor philosophies on holding periods

(00:27:30) - Are hold periods even important?

(0:28:20) - Sam’s rollup holding thesis

(00:36:21) - Kaustubh’s thoughts on M&A

(00:43:07) - Strategic planning tools and support groups

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 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