The Intentional Owner podcast

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The Pursuit of Unhinged Demand - The Intentional Owner #18 1:03:42

8일 전1:03:42

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1:03:42

Kaustubh Deo and Sam Rosati return for a wide-ranging episode that blends personal updates with deeper reflections on business building and investment philosophy. They begin by recapping Sam’s family trip to Hawaii and updating their ongoing fitness tracker challenge, before diving into a detailed reflection on their recent interview with Chase Murdock. The conversation explores Chase’s unique approach to building a HoldCo in Salt Lake City, emphasizing leadership, locality, and a low-leverage, high-growth strategy. From there, the hosts discuss the appeal and drawbacks of various HoldCo models, the nuances of risk management, and their evolving approaches to cash management, M&A, and side hustles. They close by reflecting on the power of writing and teaching as a tool for community building and legacy. They discuss: Chase Murdock’s approach to building a local, low-leverage HoldCo and why it works The pros and cons of operating with a partner and staying in a narrow geographic market How both hosts are thinking about personal cash allocation, passive investing, and risk barbell strategies The case for buying small add-ons in industries you already know Building a long-term content and syndicate platform through consistent writing and investing An insightful episode for entrepreneurs balancing operations, investing, and long-term life design. 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 (00:01:10) - Hawaii vacation recap (00:04:51) - Fitness and activity tracker update (00:05:52) - Reflecting on the Chase Murdock interview (00:19:39) - Personal reflections on business models (00:22:23) - Diverse investment strategies (00:32:53) - Risk management in investments (00:33:13) - Cash management strategies (00:35:02) - Approach to M\&A and industry focus (00:38:35) - Sourcing and outreach in M\&A (00:46:39) - Building a side hustle (00:50:53) - The importance of creative writing and communication (01:03:04) - Upcoming guest and conclusion…

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Rejecting the Arrival Fallacy - Chase Murdock: CEO of Decada Group 58:09

22일 전58:09

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58:09

In this episode of The Intentional Owner, co-hosts Sam Rosati and Kaustubh Deo welcome their first guest, Chase Murdock, CEO of the Decada Group. Chase reflects on his transition from high-growth, venture-backed startups to building a durable, decentralized holding company rooted in Salt Lake City. He shares how his early career in venture capital led to burnout and the realization that long-term fulfillment comes from building intentionally, not chasing exits. The conversation dives into the formation of Decada, the value of partnerships, and how Chase and his partner, Adam, have shaped their portfolio by focusing on sustainability, operator autonomy, and local impact. Chase also details how Decada structures its companies, the evolution of their operating model, and what it truly means to be a steward of enduring businesses. They discuss: * Why Chase and Adam rejected the “arrival fallacy” in favor of a sustainable, long-term ownership model * How their first business, Tailor Cooperative, became the foundation for a broader holding company vision * The importance of partnerships and how complementary mindsets—not just skillsets—can strengthen resilience * Why Decada decentralizes operations and empowers CEOs with budgetary and strategic autonomy * How Chase is redefining success by aligning work, life, and family within his operating model This episode is a must-listen for anyone building a portfolio with long-term vision and intentional design. Links: Chase on LinkedIn - https://www.linkedin.com/in/chasemurdock/ Decada Group - https://www.decada-group.com/ 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 (00:01:54) - Introducing Chase Murdock (00:03:27) - The intention of Decada (00:10:38) - Getting off the arrival fallacy treadmill (00:17:41) - Building a great partnership (00:23:56) - Personal missions (00:29:59) - Strengths and weaknesses between partners (00:33:39) - Building a “figure it out” attitude (00:36:01) - The current state of Decada (00:39:50) - Placing CEOs into businesses (00:42:54) - Capitalization structures (00:46:54) - Operating cadences (00:53:13) - Arriving at the arrival fallacy point…

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Evaluating Industries & Revenue Quality in SMB Acquisition - The Intentional Owner #16 50:38

5 weeks 전50:38

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50:38

In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo dive deep into two interconnected topics: the real tradeoffs of self-funded search versus traditional high-income careers, and tactical frameworks for evaluating industries and revenue quality in SMB acquisition. They open with a candid conversation about what draws people into ETA, weighing lifestyle freedom and long-term upside against the more predictable, but often relentless, trajectory of big law, PE, and IB. Then, they shift gears into practical diligence frameworks, sharing how they’ve each evaluated revenue quality, industry dynamics, and growth opportunities in their own businesses. From win rates and customer retention metrics to local market analysis and pricing strategy, this conversation is rich with hard-earned insights. They discuss: Why expected returns in self-funded search may be lower than other high-income career paths How to measure and evaluate revenue quality using real customer data Frameworks for assessing industry attractiveness as a first-time searcher The role of local market dynamics, backlog trends, and customer segmentation in due diligence Common pitfalls in organic growth assumptions and the limits of TAM analysis A tactical conversation for anyone considering ETA or looking to sharpen their diligence process. 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 (00:00:48) - Catching up (00:07:02) - The alternatives to Self-Funded Searches (00:20:07) - The pitfalls of an industry-agnostic Search (00:22:34) - Thoughts on Revenue quality (00:31:46) - Key data points and gut checks to know if the business/industry is healthy (00:36:52) - Developing organic growth (00:42:10) - Discovering win-rates in Search (00:45:35) - Closing questions!…

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How to Navigate the First 90 Days Post-Acquisition - The Intentional Owner #15 1:00:44

7 weeks 전1:00:44

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1:00:44

In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo dive deep into the critical first 90 days following a business acquisition. Drawing from their own operating experience, they discuss tactical items like transition checklists and asset conversion, while also exploring the softer—but equally important—aspects of communication with employees and customers. They examine the nuances of announcing a deal, managing early team dynamics, and the risk of misaligned retention strategies. Along the way, they share candid reflections on the evolving identity of a business owner and the long road to earning trust and building cultural buy-in. They discuss: Practical challenges and checklists for the first week of an asset deal transition Strategic communication approaches for customers and employees post-close Why retention bonuses can backfire and what to consider instead The long timeline and emotional complexity of "owning" a business culturally How to assess operator readiness in self-funded search deals A valuable episode for anyone navigating the early stages of ownership or evaluating what it really means to lead a small business. 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) - Catching up (00:06:26) - First 90 days post-acquisition (00:16:03) - Communication with the team (00:22:58) - Retention bonuses (00:32:26) - The moment an acquirer feels like the business has become their own (00:38:47) - Feeling like you’ve earned the team’s trust, such that you can make fundamental changes (00:50:25) - Becoming better at assessing potential operators…

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Managing Relationships between Investors, Operators, and Searchers - The Intentional Owner #14 55:06

9 weeks 전55:06

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55:06

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…

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Podcast Announcement! - The Intentional Owner 1:31

10 weeks 전1:31

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1:31

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!

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How Operators can Balance Ambition with a Sustainable Life - The Intentional Owner #13 1:03:04

11 weeks 전1:03:04

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1:03:04

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…

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The Eisenhower Matrix for Small Business Operators - The Intentional Owner #12 46:23

12 weeks 전46:23

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46:23

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…

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Designing a Sustainable Life as a Small Business Owner - The Intentional Owner #11 38:28

13 weeks 전38:28

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38:28

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…

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Avoiding the Arrival Fallacy in Entrepreneurship - The Intentional Owner #10 49:46

14 weeks 전49:46

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49:46

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…

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Debt Service Coverage Ratio in SMB - The Intentional Owner #9 49:23

15 weeks 전49:23

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49:23

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…

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SMBash Recap - The Intentional Owner #8 46:11

16 weeks 전46:11

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46:11

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…

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Live From SMBash! - The Intentional Owner #7 42:59

17 weeks 전42:59

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42:59

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…

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Owning 100% vs. Taking Capital: The Tradeoffs That Matter - The Intentional Owner #6 1:03:09

18 weeks 전1:03:09

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1:03:09

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?…

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The Impact of SMB Ownership on Family, Spouses & Children - The Intentional Owner #5 1:04:14

19 weeks 전1:04:14

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1:04:14

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…

The Intentional Owner

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Long-Term Hold Philosophies: SMB, PE, and Investor mindsets - The Intentional Owner #4 45:25

20 weeks 전45:25

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45:25

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…

The Intentional Owner

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The Mindset and Skills that set Successful SMB Owners Apart - The Intentional Owner #3 1:05:32

21 weeks 전1:05:32

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1:05:32

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…

The Intentional Owner

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Surviving Search, Closing the Deal, and Scaling a Business for the Long Haul - The Intentional Owner #2 54:34

22 weeks 전54:34

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54:34

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…

The Intentional Owner

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Abandoning the Rat Race for SMB & ETA -The Intentional Owner #1 1:04:02

23 weeks 전1:04:02

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1:04:02

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…

The Intentional Owner

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Welcome to The Intentional Owner 1:41

24 weeks 전1:41

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1:41

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.…

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