Long-Term Hold Philosophies: SMB, PE, and Investor mindsets - The Intentional Owner #4
Release Date: 03/20/2025
The Realities of Leading and Scaling Multiple Businesses - Palmer Higgins - Partner at Chenmark
The Intentional Owner
Palmer Higgins joins co-hosts Kaustubh Deo and Sam Rosati to discuss building Chenmark, lessons from operating small businesses, and maintaining a long-term approach to leadership. Palmer shares his early career in finance and a startup, the path to acquiring multiple companies with family members, and the importance of agency in shaping his career decisions. He reflects on the challenges of hiring operators, stepping into a CEO role without prior management experience, and the operational intensity of turnaround situations. The discussion also covers Chenmark’s philosophy on growth, capital...
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The Pursuit of Unhinged Demand - The Intentional Owner #18
The Intentional Owner
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...
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Rejecting the Arrival Fallacy - Chase Murdock: CEO of Decada Group
The Intentional Owner
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...
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Evaluating Industries & Revenue Quality in SMB Acquisition - The Intentional Owner #16
The Intentional Owner
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...
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How to Navigate the First 90 Days Post-Acquisition - The Intentional Owner #15
The Intentional Owner
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...
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Managing Relationships between Investors, Operators, and Searchers - The Intentional Owner #14
The Intentional Owner
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...
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Podcast Announcement! - The Intentional Owner
The Intentional Owner
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
The Intentional Owner
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...
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The Eisenhower Matrix for Small Business Operators - The Intentional Owner #12
The Intentional Owner
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...
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Designing a Sustainable Life as a Small Business Owner - The Intentional Owner #11
The Intentional Owner
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...
info_outlineIn 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