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
Why Purpose Outlasts Profit in Building a Successful Business - Mark Sinatra - CEO @ AspenHR
Nov 601:09:52Tap to summarizeMark Sinatra joins Sam Rosati and Kaustubh Deo to reflect on his 15-year journey through entrepreneurship, search funds, and leadership. From launching his first search in 2007 to navigating the 2008 financial crisis as a new CEO, Mark shares how perseverance, self-discipline, and purpose carried him through some of the most difficult chapters of his business life. He discusses building resilience during downturns, the evolution of the ETA ecosystem, and how his experiences led him to his current role at Aspen HR, where he helps professionalize HR operations for small and mid-sized companies. They discuss: • How Mark discovered the search fund model and built conviction to pursue it • Navigating the 2008 financial crisis just months after acquiring his first company • Lessons learned from employee turnover, client loss, and leadership under pressure • Why physical and mental health are essential to sustaining long-term success • The transition from owner-operator to investor and executive at Aspen HR Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first Sam on X - https://x.com/Sam_Rosati Mark on LinkedIn - https://www.linkedin.com/in/msinatra/ Please contact our valued sponsor Aspen HR (www.aspenhr.com, sales@aspenhr.com) for a quote on PEO services and a complimentary HR due diligence assessment Topics: (00:00:00) - Intro (00:02:23) - Mark's career and background (00:07:24) - Launching a search fund (00:13:53) - Navigating the Great Financial Crisis (00:21:17) - Operational challenges and employee turnover (00:24:44) - Inflection point and recovery (00:33:03) - Building a strong management team (00:35:50) - Navigating non-linear business paths (00:41:04) - Winning competitive deals (00:43:28) - Insights from investors and turning points (00:47:24) - Challenges of change management (00:49:56) - Joining Aspen HR during the pandemic (00:52:40) - Aspen HR's business model and client focus (01:03:37) - PEO model explained (01:07:54) - Advice for searchers and operators
Transcribe →Building Industry Credibility and Managing Risk as an Owner - The Intentional Owner #24
Oct 2301:11:33Tap to summarizeKaustubh Deo and Sam Rosati return for a conversation on blending lessons from recent industry conferences with a deep dive into the financial realities of running a small business. Drawing from Kaustubh's experience speaking at an arborist conference and Sam's perspective on using events for networking and deal flow, they explore how conferences can reinforce professional credibility and open new opportunities. From there, the discussion shifts toward capital structure, liquidity, and risk management—offering practical insights into how owners can balance leverage, cash reserves, and personal investing to build more resilient companies. They discuss: • How industry conferences can strengthen brand reputation and open new doors • Why liquidity often matters more than lowering leverage in small business acquisitions • Structuring debt and equity for long-term stability and optionality • Managing cash flow swings and working capital through changing market conditions • How operators think about inflation, investing, and personal risk alignment Support our Sponsors: The Kalmar Group is a recruitment firm who partners with small business owners around the nation to find Manager to VP level hires in sales, marketing, operations, and finance across multiple niche industries. Website: https://www.thekalmargroup.com Twitter: https://x.com/thesmbrecruiter LinkedIn: https://www.linkedin.com/in/dylanscroggins/ Aspen HR Please contact our valued sponsor Aspen HR (www.aspenhr.com, sales@aspenhr.com) for a quote on PEO services and a complimentary HR due diligence assessment 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 (00:01:33) - Catching up (00:04:23) - Arborist conference insights (00:06:10) - The value of industry conferences (00:10:03) - Networking and education (00:12:54) - Leadership and industry engagement (00:24:57) - Conference strategies for searchers (00:31:31) - Building industry relationships (00:39:07) - Discussing Seattle's climate and business potential (00:40:09) - Approach to business leverage and debt (00:50:56) - Personal finance strategies and investments (01:04:45) - Sports and networking benefits (01:09:51) - Closing thoughts and fun facts
Transcribe →How Great Hiring Decisions Transform Small Businesses - Dylan Scroggins - The Intentional Owner #23
Oct 901:06:29Tap to summarizeIn this episode of The Intentional Owner, co-hosts Sam Rosati and Kaustubh Deo sit down with recruiter and entrepreneur Dylan Scroggins to discuss his unconventional path from software sales to launching his own recruiting firm, Kalmar Group. Dylan shares how his experience in sales, his exposure to the SMB and ETA communities, and a pivotal decision not to buy a business led him toward building one instead. The conversation explores what entrepreneurship truly looks like—its realities, risks, and rewards—as well as how Dylan helps small business owners find and develop leadership talent through intentional recruiting. They discuss: The lessons Dylan learned at ETA Bootcamp that made him realize he didn't want to buy a business Why recruiting is a critical yet undervalued function in small business leadership The emotional and practical challenges of starting a business while raising a family How to evaluate whether you should buy, build, or lead a company based on your strengths and stage of life The value of intentional hiring and how owner-led businesses can think strategically about talent acquisition Support our Sponsors: The Kalmar Group is a recruitment firm who partners with small business owners around the nation to find Manager to VP level hires in sales, marketing, operations, and finance across multiple niche industries. Website: https://www.thekalmargroup.com Twitter: https://x.com/thesmbrecruiter LinkedIn: https://www.linkedin.com/in/dylanscroggins/ 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 (00:02:21) - Dylan's career journey (00:04:02) - SMbootcamp (00:05:34) - Launching Kalmar Group (00:11:58) - Balancing entrepreneurship and family (00:16:41) - The reality of entrepreneurship (00:25:02) - The challenges and rewards of recruiting (00:30:37) - Support systems and family dynamics (00:33:35) - Navigating emergency work and boundaries (00:37:58) - Understanding the role of recruiters (00:40:57) - The importance of a recruiter in SMBs (00:46:21) - Confidential searches and client expectations (00:53:13) - Recruiting misconceptions and client education (00:57:57) - Pricing and payment structures for recruiters (01:02:57) - Final thoughts and contact information
Transcribe →The Long Game of Owner Psychology - The Intentional Owner #22
Sep 2501:17:34Tap to summarizeIn this episode of The Intentional Owner, co-hosts Sam Rosati and Kaustubh Deo are joined in the opening segment by Alex Hinch, co-founder of Rejigg, a platform designed to streamline small business acquisitions. Alex shares how Rejigg connects business owners with buyers, the inefficiencies in traditional brokerage models, and how their success-fee structure aligns incentives. After the discussion with Alex, Sam and Kaustubh dive into broader conversations about operating a business, managing busy seasons, and finding ways to create both short-term wins and long-term growth. They discuss: How Rejigg is creating a more efficient marketplace for small business acquisitions Why charging buyers instead of sellers attracts higher-quality deal flow The challenges and tradeoffs between fixed price versus time and materials contracts Strategies to maintain team morale during peak seasons Ways to generate consistent cash flow and growth in a leveraged small business Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first Sam on X - https://x.com/Sam_Rosati Support our sponsor, Rejigg - https://bit.ly/RejiggTIO Topics: (00:00:00) - Intro (00:01:25) - Our conversation with Alex Hinch of Rejigg, sponsor of today's episode (00:04:07) - Rejig's unique approach (00:05:03) - Understanding the market dynamics (00:06:44) - Rejig's business model and success fees (00:10:03) - Building inventory and outreach strategies (00:13:30) - Challenges and opportunities in ETA (00:20:42) - Time and materials vs. fixed price (00:31:08) - Boosting team morale during busy season (00:45:24) - Sales vs. crew efficiency (00:47:02) - Seasonal work and backlog management (00:49:09) - Navigating financial leverage (00:50:36) - Growth strategies and challenges (00:58:09) - Exploring geographic expansion (01:10:14) - Optimizing marketing and lead flow (01:12:09) - Financial strategies for cash flow (01:16:14) - Invitation for business coaching
Transcribe →Evaluating Industries & Revenue Quality in SMB Acquisition - The Intentional Owner #16
Jul 3, 202500:50:38Tap to summarizeIn 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!
Transcribe →How to Navigate the First 90 Days Post-Acquisition - The Intentional Owner #15
Jun 19, 202501:00:44Tap to summarizeIn 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
Transcribe →Managing Relationships between Investors, Operators, and Searchers - The Intentional Owner #14
Jun 5, 202500:55:06Tap to summarizeIn 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
Transcribe →Podcast Announcement! - The Intentional Owner
May 29, 202500:01:31Tap to summarizeQuick 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!
Transcribe →How Operators can Balance Ambition with a Sustainable Life - The Intentional Owner #13
May 22, 202501:03:04Tap to summarizeIn 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
Transcribe →The Eisenhower Matrix for Small Business Operators - The Intentional Owner #12
May 15, 202500:46:23Tap to summarizeIn 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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