Shows
The Intentional OwnerThe Pursuit of Unhinged Demand - The Intentional Owner #18Kaustubh 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...2025-07-311h 03The Intentional OwnerRejecting the Arrival Fallacy - Chase Murdock: CEO of Decada GroupIn 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...2025-07-1758 minThe Intentional OwnerEvaluating Industries & Revenue Quality in SMB Acquisition - The Intentional Owner #16In 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 ra...2025-07-0350 minThe Intentional OwnerHow to Navigate the First 90 Days Post-Acquisition - The Intentional Owner #15In 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. 2025-06-191h 00The Intentional OwnerManaging Relationships between Investors, Operators, and Searchers - The Intentional Owner #14In 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...2025-06-0555 minThe Intentional OwnerPodcast Announcement! - The Intentional OwnerQuick 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!2025-05-2901 minThe Intentional OwnerHow Operators can Balance Ambition with a Sustainable Life - The Intentional Owner #13In 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 ri...2025-05-221h 03The Intentional OwnerThe Eisenhower Matrix for Small Business Operators - The Intentional Owner #12In 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...2025-05-1546 minThe Intentional OwnerDesigning a Sustainable Life as a Small Business Owner - The Intentional Owner #11In 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...2025-05-0838 minThe Intentional OwnerAvoiding the Arrival Fallacy in Entrepreneurship - The Intentional Owner #10In 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...2025-05-0149 minThe Intentional OwnerDebt Service Coverage Ratio in SMB - The Intentional Owner #9In 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...2025-04-2449 minThe Intentional OwnerSMBash Recap - The Intentional Owner #8In 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...2025-04-1746 minThe Intentional OwnerLive From SMBash! - The Intentional Owner #7In 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 fat...2025-04-1042 minThe Intentional OwnerOwning 100% vs. Taking Capital: The Tradeoffs That Matter - The Intentional Owner #6In 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 al...2025-04-031h 03The Intentional OwnerThe Impact of SMB Ownership on Family, Spouses & Children - The Intentional Owner #5In 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. ...2025-03-271h 04The Intentional OwnerLong-Term Hold Philosophies: SMB, PE, and Investor mindsets - The Intentional Owner #4In 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...2025-03-2045 minThe Intentional OwnerThe Mindset and Skills that set Successful SMB Owners Apart - The Intentional Owner #3In 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. 2025-03-131h 05The Intentional OwnerSurviving Search, Closing the Deal, and Scaling a Business for the Long Haul - The Intentional Owner #2Surviving 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 runni...2025-03-0654 minThe Intentional OwnerAbandoning the Rat Race for SMB & ETA -The Intentional Owner #1In 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 o...2025-02-271h 04The Intentional OwnerWelcome to The Intentional OwnerWelcome 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.2025-02-1901 min
Acquiring MindsHow to Raise Money from Investors to Buy a Business2 searchers, Kaustubh Deo & Kevin Bibelhausen, share how they found investors to provide money to buy their businesses. Topics in Kevin and Kaustubh’s interview:How Twitter helps searchers learn and networkHow Kevin found investors after his funding fell throughHow they selected investorsWhat a good pitch meeting looks likeHow they communicate with investors post-acquisitionThe power of superconnectors when raising fundsThe size of their cap tablesHow they organized their contacts while pitching investorsHow to get the most equity in your businessThe most gratifying and stressful parts of running their businessesLinks and how to contact Kevin and Kau...2023-05-0848 min