Podcast
The Intentional Owner
Hosted by Kaustubh Deo & Sam Rosati · EN
The Intentional Owner provides an in-depth & personal look at life as a small business owner. We discuss how to acquire, operate, and grow small businesses in ways that achieve positive impacts for yourself, for your family, for your employees, and for your community. We love everything to do with small business acquisitions & entrepreneurship and want to support our fellow small business owners in having a fulfilling life.
39episodes
Episodes
Newest firstAll episodes
Designing a Sustainable Life as a Small Business Owner - The Intentional Owner #11
May 8, 202500:38:28Tap to summarizeIn 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
Transcribe →Avoiding the Arrival Fallacy in Entrepreneurship - The Intentional Owner #10
May 1, 202500:49:46Tap to summarizeIn 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
Transcribe →Debt Service Coverage Ratio in SMB - The Intentional Owner #9
Apr 24, 202500:49:23Tap to summarizeIn 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
Transcribe →SMBash Recap - The Intentional Owner #8
Apr 17, 202500:46:11Tap to summarizeIn 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
Transcribe →Long-Term Hold Philosophies: SMB, PE, and Investor mindsets - The Intentional Owner #4
Mar 20, 202500:45:25Tap to summarizeIn 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
Transcribe →The Mindset and Skills that set Successful SMB Owners Apart - The Intentional Owner #3
Mar 13, 202501:05:32Tap to summarizeIn 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
Transcribe →Surviving Search, Closing the Deal, and Scaling a Business for the Long Haul - The Intentional Owner #2
Mar 6, 202500:54:34Tap to summarizeSurviving 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
Transcribe →Abandoning the Rat Race for SMB & ETA -The Intentional Owner #1
Feb 27, 202501:04:02Tap to summarizeIn 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
Transcribe →Welcome to The Intentional Owner
Feb 19, 202500:01:41Tap to summarizeWelcome 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.
Transcribe →