In this episode of The Intentional Owner, cohosts Kaustubh Deo and Sam Rosati take a reflective look at the realities of small business ownership, personal growth, and the long road toward sustainability. Their conversation begins with an honest assessment of the emotional cycles that define entrepreneurship and evolves into a thoughtful exercise in imagining advice from their future selves. Along the way, they explore comparisons with peers, the tension between ambition and personal values, and the challenge of balancing financial security with meaningful control of time. They also discuss delegation, team building, and what it takes to create optionality as an owner.

They discuss:

• How Kaustubh and Sam would advise their younger entrepreneurial selves

• Why comparisons with peers can both motivate and distract

• The ongoing struggle to balance work, stress, and long term sustainability

• Lessons learned from early management challenges and evolving values

• The importance of building team capacity to reduce day to day volatility

• Opportunities for nonlinear growth, including new service lines and commercial work

• How long term financial security shapes decisions and personal fulfillment

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, [email protected]) 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 (00:02:24) - Introspection and entrepreneurial mindsets (00:06:18) - Comparing journeys and business strategies (00:11:10) - Balancing work and personal life (00:19:02) - Evaluating financial security and time independence (00:29:41) - Looking ahead: Future goals and reflections (00:31:35) - Balancing the emotional rollercoaster of small business ownership (00:32:57) - Delegating tasks to manage business setbacks (00:35:29) - Reflecting on business growth and future expansion (00:38:03) - Exploring non-linear growth opportunities (00:39:43) - Challenges of adding new service lines (00:47:08) - Considering commercial and residential market differences (00:53:54) - The importance of optionality in business strategy (00:56:22) - Tax and financial management insights (00:57:55) - Concluding thoughts and future plans

Mark 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, [email protected]) 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

Kaustubh 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, [email protected]) 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

In 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

In 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

Sam Rosati and Kaustubh Deo dive into the realities of small business ownership in this episode of The Intentional Owner. They start with a lighthearted discussion about a bizarre voicemail Kaustubh received, then move into deeper conversations around decision-making, lifestyle shifts after leaving corporate jobs, and the mental weight of being an owner. The hosts break down the misnomers about time freedom, the challenges of managing people, and the constant need to sell not just to customers but also to teams and stakeholders. They also debate whether aspiring buyers should pursue larger businesses with structure or smaller companies that allow faster entry, sharing candid lessons from their own journeys.

They discuss:

• The mental and emotional burden of decision-making as an owner
• Lifestyle changes and work-life balance after leaving corporate careers
• Misconceptions about time control and workload in entrepreneurship
• The importance of people management and sales as core ownership skills
• Trade-offs between buying large structured businesses versus smaller, scrappier ones

Support our Sponsors:

Kalmar Group

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, [email protected]) 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

Follow along with the guys' fitness tracker! - https://bit.ly/3T4EpHw

Topics:

(00:00:00) - Intro (00:01:06) - Unexpected voicemail drama (00:10:10) - Balancing work and personal life (00:14:15) - The reality of being an SMB owner (00:31:35) - The burden of decision-making as a business owner (00:33:56) - Strategies for prioritizing decisions (00:39:26) - The risks of buying smaller businesses (00:41:06) - The importance of liquidity and cash flow (00:51:03) - The competitive landscape of business acquisition (00:54:18) - The need for direct proprietary search (01:00:26) - Concluding thoughts and future plans

Sam Rosati and Kaustubh Deo dive into the realities of small business ownership, exploring the tension between working in the business versus working on it. They share firsthand experiences from recent projects, unpack the challenges of scaling into larger, more complex jobs, and reflect on how owner involvement shapes day-to-day operations. The conversation offers a candid look at the trade-offs entrepreneurs face when balancing growth ambitions with operational realities.

We discuss:

• Lessons from moving between residential and commercial projects

• The role of owner dependency and how to assess it in acquisitions

• Defining the difference between working in versus on the business

• The importance of lead generation and long-term customer value

• Why strong operators are often more critical than capital or deals

This episode provides practical insights for entrepreneurs navigating the complexities of ownership and growth.

Support our Sponsors:

Kalmar Group

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, [email protected]) 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

Follow along with the guys' fitness tracker! - https://bit.ly/3T4EpHw

Topics:

(00:00:00) - Intro (00:01:05) - Challenges of large-scale projects (00:01:59) - Daily operations and coordination (00:07:29) - Commercial vs. residential jobs (00:17:56) - Working on vs. in the business (00:27:23) - Evaluating business relationships (00:29:03) - Understanding owner dependence (00:31:54) - Case study: Seller separation (00:33:15) - Challenges of owner dependence (00:33:55) - The role of technical expertise (00:38:16) - Managing customer complaints (00:40:41) - Lead generation strategies (00:52:23) - Reflections on search partnerships (00:56:20) - Conclusion and final thoughts

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 allocation, and supporting CEOs for sustainable success.

They discuss:

• How Palmer transitioned from finance to entrepreneurship through small business acquisitions

• Lessons learned from failed operator hires and the value of developing leaders internally

• The challenges and rewards of running a company without prior industry experience

• Why Chenmark prioritizes long-term orientation over aggressive short-term growth targets

• Strategies for blending work and personal life to maintain balance and sustainability

This episode offers valuable insights for aspiring business owners and operators who want to build enduring companies while preserving quality of life.

Support our Sponsors:

Kalmar Group

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, [email protected]) 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

Follow along with the guys' fitness tracker! - https://bit.ly/3T4EpHw

Chenmark - https://chenmark.com/

Palmer on LinkedIn - https://www.linkedin.com/in/palmerhiggins/

Topics:

(00:00:00) - Intro (00:01:18) - Work-life balance and office chaos (00:04:18) - Palmer's background and career path (00:04:43) - The genesis of Chenmark (00:08:53) - First acquisition and early challenges (00:13:58) - The decision to leave finance (00:17:00) - Exploring entrepreneurship (00:33:46) - The first business acquisition (00:42:15) - Taking charge: From search to CEO (00:47:00) - The intensity of business ownership (00:50:11) - Sustaining long-term success (00:54:23) - Managing multiple businesses (00:57:22) - Work-life integration strategies (01:04:10) - The future vision for Chenmark (01:16:54) - Fitness competition updates!

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

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