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

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!

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

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

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!

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