The Intentional Owner

Buying a Remote Business Through Self-Funded Search

Thu, 30 Apr 2026 05:00:00 -0000

Sam Rosati and Kaustubh Deo are joined by Vince and Kalyn Saulsberry-Fong to share the story behind acquiring a niche data business as a married couple. They walk through their transition from corporate careers into entrepreneurship, the intentional planning that led to their search, and how they aligned their business goals with their personal priorities. The conversation highlights their highly specific investment thesis around proprietary data, the unexpected challenges they faced post-close, and how they are thinking about building a scalable, automated business while preparing for a major life transition.

They discuss:

How Vince and Kalyn transitioned from corporate careers into a joint search and acquisition journey
Why proprietary data became the foundation of their highly targeted investment thesis
The process of finding and acquiring a remote healthcare data business through a direct seller connection
Lessons from early ownership including working capital surprises and operational realities
How they are balancing business ownership, automation, and preparing for their first child

Support our Sponsor:

NewCo Risk gives SMB businesses access to the same bespoke approach, sophisticated strategies and big thinking as the leading global insurance consulting firms. Learn more @ https://www.newcorisk.com/

Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses. Learn more at ⁠https://bay-biz.com

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

Links:

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Links:

Kalyn on LinkedIn - https://www.linkedin.com/in/kalynsaulsberry/

Vince on LinkedIn - https://www.linkedin.com/in/vince-saulsberry-fong/

Audience Synergy - https://audiencesynergy.com/

Topics:

(00:00:00) - Intro (00:02:17) - Meet Vince and Kalyn (00:10:02) - Vision planning and goals (00:21:34) - Search thesis and buy box (00:27:18) - Audience synergy explained (00:30:52) - The catch and founder fit (00:32:42) - Monetization and revenue mix (00:35:27) - Data diligence and margins (00:37:41) - Finding the deal fast (00:41:25) - Direct seller negotiations (00:44:54) - Self funded search reality (00:46:53) - Day one transition plans (00:49:12) - Channel partners onboarding (00:51:20) - Working capital surprises (00:55:14) - Pregnancy and operations (01:01:03) - Automation and ai systems (01:09:24) - Spouse partnership dynamics (01:13:31) - Wrap and sponsor reads

Insurance Due Diligence in Small Business Acquisitions

Thu, 16 Apr 2026 05:00:00 -0000

Sam Rosati and Kaustubh Deo are joined by Andy Harbut and Josh Richman to break down the often-overlooked role of insurance in small business acquisitions. Drawing from decades of experience in private equity and insurance brokerage, Andy and Josh share how they built NewCo Risk through a hybrid of acquisition and startup, and why they chose to focus on the underserved search and ETA community. The conversation dives into real-world examples of how insurance diligence can make or break a deal, along with lessons from their first year as entrepreneurs scaling a niche, service-heavy business.

They discuss:

- How insurance diligence can uncover hidden risks that materially impact deal viability

- Why many small businesses are underinsured or mispriced and how that affects buyers

- The strategy behind building an insurance brokerage through a carveout and acquisition model

- Key operational and technology decisions that shaped NewCo Risk’s early growth

- Why sales capability is critical for operators and searchers running small businesses

Support our Sponsor:

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

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
(00:02:34) - Introducing Josh and Andy
(00:07:22) - Learnings from the self-funded community
(00:12:15) - How Josh and Andy think about the NewCo Risk business model
(00:15:22) - The decision to start NewCo Risk
(00:24:45) - The state of NewCo in 2026
(00:29:14) - How to run your business for less money
(00:32:16) - Josh and Andy’s roles within the business
(00:39:28) - War stories
(00:51:23) - Getting in touch

Making Smarter Financial Decisions in Your SMB with Michael Young

Thu, 02 Apr 2026 05:00:00 -0000

In this episode of The Intentional Owner, Kaustubh Deo sits down with Michael Young to explore the realities of building and scaling a people-first accounting firm after a long and uncertain search journey. Michael shares how he transitioned from Big Four accounting into entrepreneurship, ultimately acquiring and growing Bay Business Group while navigating the challenges of hiring, client selection, and operational discipline. The conversation dives into what small business owners should actually expect from bookkeeping, controller, and CFO services, and how financial clarity can drive better decision-making. Along the way, Michael offers an honest look at the emotional and practical challenges of search, and why defining your “why” matters more than anything. They discuss: - The differences between bookkeeping, controller, and CFO support, and what small businesses actually need - Why search is unpredictable and heavily influenced by luck, not just effort - How to scale a people-driven business and the challenges of hiring high-quality talent - The importance of client selection, scope control, and saying no to the wrong fit - How AI is changing accounting and why advisory and judgment still matter Support our Sponsor Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses. Learn more at ⁠https://bay-biz.com/⁠ Have SMB questions for Kaustubh and Sam? Email them to ⁠kd@sunthra.com⁠ and they will answer them on the Pod! 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
(00:01:26) - Introducing Michael Young
(00:04:06) - Dropping search to build a startup
(00:07:49) - Bookkeepers vs controllers
(00:11:35) - When do you need a CFO?
(00:13:03) - Owner finance literacy
(00:14:51) - Scaling a people firm
(00:16:42) - Client fit and boundaries
(00:20:09) - Operational metrics and change
(00:24:07) - Family life and time control
(00:25:22) - Long term vision and short term priorities
(00:28:50) - Ideal client profiles
(00:31:37) - Searchers as clients
(00:34:02) - Churn and scope control
(00:35:41) - Sales versus service
(00:36:34) - AI and accounting
(00:39:01) - Future proofing systems
(00:44:53) - Search journey reflections

The Financial Controls Every Small Business Needs w/ Denisse Montenegro - TIO #34

Thu, 19 Mar 2026 05:00:00 -0000

In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo sit down with Denisse Montenegro to unpack the realities of operating and scaling a business while fully owning the P&L. Denisse shares a candid look at navigating financial visibility, decision-making, and the evolving responsibilities that come with ownership. The conversation explores the tension between delegation and accountability, as well as the importance of building the right support systems across finance and operations. Throughout the episode, Denisse offers an honest perspective on what it actually feels like to be in the operator’s seat, especially when answers are not always clear.

We discuss:

The responsibility of being both the operator and the ultimate owner of the P&L
How to think about delegation when everything still feels like your responsibility
The role of bookkeeping, accounting, and advisory support in growing a business
Why complementary partnerships across finance and operations create leverage
The challenge of finding peers who truly understand the financial realities of ownership

Support our Sponsors

Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses. Learn more at https://bay-biz.com/

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

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
(00:02:22) - Introducing Denisse
(00:06:41) - Acquisition story and first year challenges
(00:12:11) - Financial awareness as an owner
(00:17:48) - The P&L owner seat
(00:23:14) - Cash flow vs reported profits
(00:29:55) - Bookkeeping vs real financial insight
(00:35:40) - Surviving the turnaround year
(00:42:12) - Advisory support and peer groups
(00:48:27) - Advisory board idea
(00:55:12) - Discipline in financial review
(01:02:30) - Closing thoughts and advice for new owners

Self-Funded ETA vs. Independent Sponsorship - The Intentional Owner #33

Thu, 05 Mar 2026 06:00:00 -0000

In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo break down the real differences between self-funded ETA and independent sponsorship. Drawing from their own experiences, they explore how each path shapes your day-to-day responsibilities, risk profile, compensation structure, and long-term upside. They go beyond surface-level comparisons to unpack capitalization, personal guarantees, M&A strategy, and the often misunderstood economics behind equity splits and carry.

The conversation also addresses a growing misconception: that moving “up market” to avoid an SBA personal guarantee automatically makes the path easier. Sam and Kaustubh explain why larger deals come with rarer air, more sophisticated competition, significantly higher deal costs, and greater dead-deal risk. They provide practical context around governance control, management fees versus salaries, pref/common structures, and why leverage is the hidden engine behind self-funded search economics.

They discuss:

- The Core Differences Between Self-Funded Search And Independent Sponsorship

- Day-To-Day Responsibilities Of An Operator Versus A Board-Level Sponsor

- How Capitalization Structures Shape Risk, Control, And Upside

- Why Dead Deal Risk Is Dramatically Higher In Larger Independent Sponsor Deals

- The Real Economics Of Equity Step-Ups, Carry, And Long-Term Wealth Creation

Support our Sponsor:

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

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 (00:01:32) - Super Bowl in Seattle (00:07:41) - ETA models compared (00:12:05) - Day to day roles (00:15:54) - Hold period and equity (00:22:46) - Salary vs management fee (00:25:04) - M&A strategy differences (00:28:29) - Capital stack basics (00:29:33) - Earnouts and leverage (00:30:08) - Personal guarantees explained (00:31:09) - Who fits indie sponsorship (00:33:40) - The deal size no man's land (00:35:24) - SBA vs conventional debt (00:36:20) - SBIC lenders overview (00:39:26) - Dead deal cost risk (00:45:15) - Indie sponsor economics reality (00:45:49) - Search fund equity step up debate (00:49:45) - Owner pay and cash flow (00:52:37) - Lifestyle and age advantage (00:56:11) - Wrap up and sponsor plug

#TheIntentionalOwner #TIO #SMB

A Weekly Time Audit for Small Business Owners - The Intentional Owner #32

Thu, 19 Feb 2026 06:00:00 -0000

Sam Rosati and Kaustubh Deo take a transparent look at how they actually spend their time as entrepreneurs juggling multiple commitments. From running their primary businesses to investing, community building, family life, and personal admin, they break down their weekly hours in real numbers. The conversation evolves into a broader discussion about tradeoffs, intentionality, screen time, and what balance really looks like when you are building businesses and raising families. By the end, they explore what would change if life circumstances shifted and how their “secondary” passions might one day become the main event

They discuss:

Breaking down primary and secondary business commitments into real weekly hours
The difference between recurring obligations and one off time commitments
How live deal cycles can dramatically shift workload and family balance
The hidden cost of phone usage and screen time in entrepreneurial life
How to think about adding or removing commitments as life stages change

Support our Sponsor:

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

Topics:

(00:00:00) - Intro (00:00:58) - Discussing personal and professional commitments (00:02:12) - Breaking down work and personal life balance (00:05:24) - Detailed analysis of primary job roles (00:07:10) - Secondary job roles and extracurricular activities (00:13:20) - Time allocation and efficiency strategies (00:23:56) - Peer groups and community involvement (00:31:13) - Calculating weekly hour (00:36:14) - Challenges of business growth (00:40:03) - Time management strategies (00:48:06) - Screen time and productivity (00:56:00) - Future plans and retirement thoughts (00:58:13) - Conclusion and call to action

The Real Tradeoffs Between Operating and Investing - Mike Botkin - The Intentional Owner #31

Thu, 05 Feb 2026 06:00:00 -0000

In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo sit down with Mike Botkin for a wide-ranging conversation on operator mindset, capital alignment, and what it really takes to build and scale small businesses. Drawing from his experience growing a tiny landscaping company into one of the largest in the Southeast, Mike shares hard-earned lessons on choosing partners, knowing when to stay in the CEO seat, and why not all growth paths are created equal. The discussion blends candid reflections on leadership, stress, and lifestyle tradeoffs with tactical insights on capital structures and service business economics.

They discuss:

Why underwriting the operator matters as much as underwriting the business
The realities of giving up the CEO role and when it backfires
How capital partner incentives shape decisions in both good and bad times
The differences between residential and commercial services from an operator’s perspective
When turnarounds and small businesses can outperform larger, more polished deals

Links:

Mike on X - https://x.com/MikeBotkin_

Mike's website - https://botkinhq.com/

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Topics:

(00:00:00) - Intro (00:00:55) - Introducing the guest: Mike Botkin (00:06:23) - Mike's journey in the landscaping business (00:17:35) - Challenges of being a CEO (00:23:26) - Finding the right role: operator vs. advisor (00:36:04) - The value of turnarounds and small business investments (00:37:23) - Navigating business challenges and stress (00:38:03) - Finding your passion in business operations (00:38:42) - The micro business operator's advantage (00:42:15) - Balancing lifestyle and business goals (00:52:59) - Choosing the right capital partner (00:58:33) - Residential vs. commercial services debate (01:10:50) - Launching commercial services: tips and strategies

Buying a Business Means Owning the Sales Function with Andrew Gazdecki of Acquire.com - The Intentional Owner #30

Thu, 22 Jan 2026 06:00:00 -0000

Andrew Gazdecki joins Kaustubh Deo and Sam Rosati for a wide-ranging conversation on building, buying, and selling small businesses. Andrew shares the origin story of acquire.com, from selling his first startup to realizing how broken the small business M&A process was for founders. The discussion explores how sales, market selection, and distribution matter more than perfect products, along with the realities of valuation in small tech-enabled businesses. The episode also dives into Andrew’s personal journey, including burnout, delegation, and redefining success as a founder.

They discuss:

Why sales is the most important role for owners of small businesses under $3–5M in revenue
How acquire.com evolved from a side project into a marketplace with thousands of closed transactions
The difference between startup-style valuations and how small businesses are actually priced and sold
What makes a strong buyer in competitive acquisition processes, and why trust often beats price
Lessons from burnout, delegating control, and building a company that supports long-term 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, 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 (00:01:03) - Andrew's entrepreneurial journey (00:03:03) - The birth and growth of acquire.com (00:03:57) - Challenges and successes in acquisitions (00:06:53) - Marketplace dynamics and buyer profiles (00:20:28) - Andrew's first startup experience (00:25:14) - The role of luck and market trends (00:30:33) - Building the marketplace: from script to success (00:31:53) - Non-technical founders and code scripts (00:33:08) - Early influences and entrepreneurial drive (00:35:01) - Day in the life: from hustle to balance (00:40:07) - Burnout and finding balance (00:45:29) - Delegation and business growth (00:47:56) - The rewarding journey of entrepreneurship (00:54:03) - Advice for aspiring buyers (00:59:52) - Final thoughts and reflections

Search Sucks, But it's Easier than Running a Business - The Intentional Owner #29

Thu, 08 Jan 2026 06:00:00 -0000

In this episode of The Intentional Owner, co-hosts Sam Rosati and Kaustubh Deo unpack the less talked about realities of search, small business ownership, and operating with leverage. They explore why the search phase feels emotionally taxing yet pales in comparison to the ongoing stress of running a business, especially during year end. The conversation weaves together personal experiences, listener questions, and practical reflections on cash flow, risk tolerance, and the mental load that comes with ownership. Along the way, Sam and Kaustubh frame hard earned lessons that aspiring and current owners often only learn the difficult way.

They discuss: • Why search feels stressful but is easier than running a business with leverage • The cash flow challenges and seasonality pressures that hit small businesses in December • How leverage and personal guarantees shape decision making and risk tolerance • Four key questions every searcher should ask before buying a business • The realities of people management and why incentives do not always drive behavior

Support our Sponsors:

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 (00:02:00) - Winter break and business challenges (00:05:10) - Holiday season financial struggles (00:08:38) - Housekeeping and upcoming events (00:09:57) - The reality of search and entrepreneurship (00:20:08) - End-of-year financial dynamics (00:26:23) - Managing costs and leveraged business challenges (00:29:31) - Introducing the newsletter: Big deal small business (00:31:24) - Four questions for aspiring searchers (00:32:39) - The personal guarantee dilemma (00:40:01) - Family support and small business ownership (00:44:02) - Running towards or away from a career (00:48:51) - Managing people and business realities (00:56:34) - Final thoughts and newsletter promotion

Owning Your Time Through Intentional Schedule Design - The Intentional Owner #28

Thu, 18 Dec 2025 06:00:00 -0000

Sam Rosati and Kaustubh Deo unpack what it actually means to own your time as a small business operator and why schedule control is harder than it sounds. Drawing on their backgrounds in demanding corporate roles and their current experience running owner led businesses, they explore the tradeoffs between productivity, energy, and personal life. The conversation moves from reactive work habits to intentional schedule design, highlighting how physical space, time blocking, and boundaries shape long-term sustainability. Throughout the episode, they emphasize that independence is not automatic and requires deliberate practice and discipline

They discuss:

• Why time independence is one of the main reasons people pursue entrepreneurship

• How early career habits from finance and law can work against long-term sustainability

• Designing weekly schedules around energy instead of hours worked

• The difference between working in the business, on the business, and on your work

• Creating physical and mental boundaries to avoid constant reactivity

Links:

Support our Sponsors:

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 (00:01:22) - Catching up (00:06:00) - Transitioning from corporate to small business (00:15:37) - Optimizing schedules for personal and business success (00:27:44) - Balancing work and personal time (00:28:33) - Creating effective work categories (00:28:55) - Importance of physical space for work (00:31:54) - Managing energy and work hours (00:40:16) - Shifting personal activities to weekdays (00:49:40) - Future plans

Navigating the Grind and Growth of SMB through Peer Groups - The Intentional Owner #27

Thu, 04 Dec 2025 06:00:00 -0000

Kaustubh Deo and Sam Rosati open this episode of The Intentional Owner with an unplanned but timely conversation about recent wins, a standout commercial project, and the value of having the right people around you. They walk through how strong project management can outperform low bids in commercial work, why certain clients prioritize quality, and how this job challenged their assumptions about pricing and margins. From there, they move into discussions around travel, golf, and time away from the day-to-day, using those experiences to reflect on leadership, focus, and the pressures of ownership. Throughout the episode, they return to a central theme: the need for peer support, shared pattern recognition, and intentional structures that help owners navigate both the grind and the growth phases of building a business.

They discuss: • Why certain commercial jobs reward operational excellence rather than low bids • How Kaustubh and Sam think about margin, project management, and client quality • The emotional and strategic value of peer groups for owners • Balancing ambition with rest, time management, and personal priorities • Ideas for building team culture, industry communities, and better training systems

Sam is hosting a 6-part Wednesday Winter Webinar Series for searchers focused on moving deals forward:

• Financial modeling

• Investor equity

• Deal flow

• LOIs

• Debt raise

• M&A strategy

Starts Dec. 10 at 12 PM EST

Link to Register: https://us06web.zoom.us/webinar/register/WN_C9KdZyJmRmCb-Xtzxt-Ixg#/registration

Support our Sponsors:

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 (00:01:12) - Navigating commercial jobs and project management (00:05:38) - A week on the road: Golf trips and networking (00:11:47) - Insights from small business owners (00:22:49) - The value of peer groups and business coaching (00:25:51) - Setting quarterly goals with peer groups (00:26:36) - Peer groups vs. business coaches (00:28:27) - Starting a niche peer group for tree care owners (00:30:03) - The benefits of group purchasing organizations (gpos) (00:32:21) - Innovative team building activities (00:38:24) - Challenges in standardizing tree care pricing (00:42:58) - Using technology to improve operations (00:46:24) - Planning and organizing peer groups (00:49:58) - Seasonal trends in blue-collar trades (00:52:39) - Upcoming events and travel plans

What a Successful 20 years in SMB Looks Like - The Intentional Owner #26

Thu, 20 Nov 2025 06:00:00 -0000

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:

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 (00:02:24) - 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

Why Purpose Outlasts Profit in Building a Successful Business - Mark Sinatra - CEO @ AspenHR

Thu, 06 Nov 2025 06:00:00 -0000

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, 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

Building Industry Credibility and Managing Risk as an Owner - The Intentional Owner #24

Thu, 23 Oct 2025 05:00:00 -0000

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:

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

How Great Hiring Decisions Transform Small Businesses - Dylan Scroggins - The Intentional Owner #23

Thu, 09 Oct 2025 07:00:00 -0000

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:

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

The Long Game of Owner Psychology - The Intentional Owner #22

Thu, 25 Sep 2025 07:00:00 -0000

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

SMB Buying Strategies that Work - The Intentional Owner #21

Thu, 11 Sep 2025 07:00:00 -0000

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

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

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

Working IN vs. ON Your Business - The Intentional Owner #20

Thu, 28 Aug 2025 07:00:00 -0000

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

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

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

The Realities of Leading and Scaling Multiple Businesses - Palmer Higgins - Partner at Chenmark

Thu, 14 Aug 2025 07:00:00 -0000

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

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

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!

The Pursuit of Unhinged Demand - The Intentional Owner #18

Thu, 31 Jul 2025 07:00:00 -0000

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

Rejecting the Arrival Fallacy - Chase Murdock: CEO of Decada Group

Thu, 17 Jul 2025 07:00:00 -0000

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

Evaluating Industries & Revenue Quality in SMB Acquisition - The Intentional Owner #16

Thu, 03 Jul 2025 07:00:00 -0000

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!

How to Navigate the First 90 Days Post-Acquisition - The Intentional Owner #15

Thu, 19 Jun 2025 07:00:00 -0000

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

Managing Relationships between Investors, Operators, and Searchers - The Intentional Owner #14

Thu, 05 Jun 2025 07:00:00 -0000

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

Podcast Announcement! - The Intentional Owner

Thu, 29 May 2025 07:00:00 -0000

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!

How Operators can Balance Ambition with a Sustainable Life - The Intentional Owner #13

Thu, 22 May 2025 07:00:00 -0000

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

The Eisenhower Matrix for Small Business Operators - The Intentional Owner #12

Thu, 15 May 2025 07:00:00 -0000

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 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

Designing a Sustainable Life as a Small Business Owner - The Intentional Owner #11

Thu, 08 May 2025 07:00:00 -0000

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 healthy operating rhythm for owners who want to stay in the game for years, not just quarters.

They also discuss:

Why many business owners neglect their physical health despite having time
The difference between startup energy and long-term operational sustainability
How habit stacking and decision fatigue shape daily behavior
Building accountability through competition and peer support
Designing boundaries around work, family, and wellness
How ownership allows for time control but requires discipline to use it well

This episode is a candid, tactical look at the intersection of personal growth and business responsibility, perfect for any owner working to align their health, habits, and leadership.

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

(00:01:12) - Catching up

(00:04:39) - Buying businesses where certification is required to operate them

(00:10:45) - Personal and Professional Non-Negotiables

(00:14:17) - Making physical fitness a priority

(00:29:50) - Creating a competition for fitness

(00:34:03) - Tactical Tips: What Sam and Kaustubh keep in their golf bags

Avoiding the Arrival Fallacy in Entrepreneurship - The Intentional Owner #10

Thu, 01 May 2025 07:00:00 -0000

In 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 and first-time CEOs. Along the way, they explore what it really means to build a business that lasts 10 years, not just three, and how to create systems, habits, and expectations that make that possible.

Key themes include:

How small business ownership reshapes identity, routines, and personal boundaries
Why perfectionism and checklist obsession can quietly kill sustainability
The mental toll of constant decision-making, unpredictability, and false urgency
Redefining success beyond equity value and financial milestones
Building in non-negotiables to protect relationships, health, and focus
Why longevity requires both operational delegation and emotional endurance

If you're deep in the operating seat—or about to step into it—this episode offers a deeply relatable, tactical conversation about what it actually takes to stay in the game long enough for ownership to be worth it.

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 (00:03:30) - Listener Email: The Reality of Business Ownership (00:05:31) - Challenges of Small Business Ownership (00:11:09) - Personal Routines and Business Demands (00:19:19) - Financial Realities: The Long Road to Success (00:23:43) - Setting Boundaries as a CEO (00:26:42) - Balancing Family and Work Routines (00:27:50) - Identity and Habit Formation (00:29:36) - Negotiating Work and Personal Time (00:30:30) - The Importance of Disconnecting (00:32:12) - Weekend Work Strategies (00:35:46) - Perfectionism vs. Effective Delegation (00:39:52) - Setting Realistic Expectations (00:43:13) - Measuring Success and Finding Balance (00:48:39) - Concluding Thoughts and Reflections

Debt Service Coverage Ratio in SMB - The Intentional Owner #9

Thu, 24 Apr 2025 07:00:00 -0000

In 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 member, buying equipment, or weathering seasonal slowdowns, Kaustubh and Sam explain how even well-capitalized businesses can find themselves squeezed when the math on debt coverage gets too tight.

Other key insights include:

How DSCR impacts hiring timelines, capex decisions, and strategic flexibility
Real-world frameworks for understanding payroll, margins, and revenue mix
The tradeoffs of financing with SBA debt and how to build in early breathing room
Why many operators underestimate cash volatility even in profitable businesses
Strategies for aligning long-term vision with the financial realities of leverage

This episode is a must-listen for anyone currently running a small business—or planning to buy one—who wants to avoid being blindsided by the very structure that made their acquisition possible. It's a candid, tactical, and grounded conversation about what it really means to operate within financial constraints.

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

(00:01:05) - Tax day For SMB and ETA folks

(00:04:42) - Podcast origins

(00:07:26) - Is SMB just micro-PE?

(00:09:38) - What Searchers are hoping to get out of ETA and SMB

(00:18:08) - The growing interest of PE in tree-care

(00:26:04) - Kaustub's intentions with Blooma

(00:32:49) - DSCR issues in SMB

(00:42:28) - Staying involved in the search community post-acquisition

(00:46:06) - Investing in Searchers

SMBash Recap - The Intentional Owner #8

Thu, 17 Apr 2025 07:00:00 -0000

In 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 reflect on standout keynotes from voices like Brent Beshore and Moses Kagan, lessons from building community outside of business, and the value of stepping outside your industry to gain perspective.

Also in this episode:

Behind-the-scenes of organizing SMBash and why it continues each year
The tension between being too in the weeds vs. too far removed as an operator
How Kaustubh applies lessons from peer groups in other industries to Blooma Tree Services
The challenge of managing growth, KPIs, and people when scaling a small business
Why community building in SMB often fills the role of religion or tribe for many entrepreneurs
A discussion on shared services, equity incentives, and decentralization in holdco structures

This episode blends event recap with personal insight, practical lessons, and a candid look at the realities of operating and building in the world of small business.

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

(00:01:07) - The Masters

(00:09:16) - SMBash recap

(00:20:11) - Why Kaustubh joins national organizations

(00:24:13) - Does being in the weeds to much take away from working "on" the business?

(00:27:13) - Recapping Kaustubh's KPI Presentation

(00:31:55) - How to improve SMBash

(00:36:21) - Why do you go to SMBash?

(00:38:15) - Wishlist for SMBash 2026

(00:42:21) - Dealing with Tax returns

Live From SMBash! - The Intentional Owner #7

Thu, 10 Apr 2025 14:02:00 -0000

In 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 father has shaped his perspective on work-life balance, time management, and the long game of ownership.

Later in the episode, they're joined by Jeff Driskel, a current NFL quarterback and co-founder of Four Pillars Group, an independent sponsor platform. Jeff talks about balancing pro football with building a portfolio of small businesses, the surprising overlap between athletics and entrepreneurship, and what it's been like running a company alongside his brother. He also shares lessons on discipline, learning new systems, and how he's using the trust he's built in the locker room to raise capital and source operators.

This episode covers:

Why people choose the small business path—and how that motivation evolves
The highs and lows of parenting while owning and growing a business
Building companies with family and managing partnership dynamics
Operator-first investing and how to find the right fit between people and businesses
The importance of long-term thinking, pattern recognition, and staying power in ETA

Recorded live, this conversation blends real stories, practical advice, and a behind-the-scenes look at what it truly means to build a life—and a business—with intention.

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

(00:01:23) - Chris Williams' journey and motivations

(00:05:15) - Balancing business and personal life

(00:17:28) - Jeff Driscoll's background and transition to ETA

(00:21:49) - The secret sauce to success

(00:21:58) - Transitioning from football to business

(00:24:24) - Working with family

(00:25:19) - Choosing the right business

(00:27:46) - Finding the right people

(00:31:05) - Leveraging football for business success

(00:34:44) - Lessons from football

(00:40:46) - Adapting to new teams and systems

Owning 100% vs. Taking Capital: The Tradeoffs That Matter - The Intentional Owner #6

Thu, 03 Apr 2025 07:00:00 -0000

In 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 also dive into:

How much control investors should have—and where to draw the line
The importance of aligning investor involvement with expectations up front
Building informal and formal support systems around the CEO
What makes an ideal investor profile and cap table structure
How investor communication and transparency affect outcomes
Why having the ability to sell—or step back—should always remain with the operator

This episode is full of practical advice for searchers, operators, and investors who want to better understand the dynamics behind ownership structure, investor relationships, and long-term alignment.

Links:

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Topics:

(00:00) - Intro

(00:01:30) - Catching up after vacation

(00:11:21) - Self-funding vs. Raising money in acquiring businesses

(00:18:00) - The pros of owning 100% of a business

(00:23:28) - Advisory boards

(00:24:48) - Is there a "right" number or mix of investors?

(00;27:35) - Finding mentors

(00:30:11) - Paying for consulting

(00:33:01) - Investor mindset towards returns

(00:39:53) - Investor communication

(00:49:38) - Governance

(00:56:34) - Should a Searcher be able to do work outside of the business they just bought?

(00:59:07) - If you could only choose one profile of investor, what would the ideal be?

The Impact of SMB Ownership on Family, Spouses & Children - The Intentional Owner #5

Thu, 27 Mar 2025 07:00:00 -0000

In 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.

They also share:

How boundaries around time, work, and presence evolve over the ownership journey
Ways to stay aligned with your partner through better communication and regular check-ins
The reality of raising kids while running a business
Lessons learned from missed moments, personal resets, and building structure at home
Tactical advice for maintaining clarity with your spouse when navigating financial risk, investor conversations, and growth decisions

This episode is less about answers and more about starting the conversation. If you're building a business while trying to be a present partner or parent—or plan to someday—this one is full of real-world perspective and practical takeaways.

Links:

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Topics:

(00:00) - Intro

(00:02:00) - Weekly recap

(0:07:19) - How SMB ownership impacts spouses and children

(00:25:30) - Conversations to have with spouses as Searchers

(00:33:20) - Financial involvement from spouses

(00:33:49) - Marriage and family planning in SMB ownership

(00:44:50) - Home success assessments

(00:48:21) - Children

(00:56:28) - Tactical tip: how searchers should reach out to investors

Long-Term Hold Philosophies: SMB, PE, and Investor mindsets - The Intentional Owner #4

Thu, 20 Mar 2025 07:00:00 -0000

In 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

The Mindset and Skills that set Successful SMB Owners Apart - The Intentional Owner #3

Thu, 13 Mar 2025 07:00:00 -0000

In 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.

Other key takeaways include:

How to prioritize tasks when you're wearing multiple hats
Why revenue generation is the biggest challenge for new SMB owners
The difference between high IQ and high EQ leadership in small business
How to leverage vendors and suppliers as true business partners

If you're considering entrepreneurship through acquisition or already in the trenches of SMB ownership, this episode is packed with real-world insights and hard-earned lessons.

Links:

Kaustubh on LinkedIn - https://www.linkedin.com/in/kaustubh-deo/

Sam on X - https://x.com/Sam_Rosati

Topics:

(00:00:00) - Intro

(00:03:18) - Weekly recap

(00:10:04) - How it feels right before you sign your first deal

(00:14:22) - How to know if you're ready to take over a business

(00:20:20) - Getting your arms around the numbers

(00:29:07) - What Sam looks for in a Searcher

(00:35:32) - Managing perfectionism in Search

(00:39:18) - Attributes in people that ensure you won't be successful in Search

(00:43:50) - Prioritization philosophies

(00:56:48) - Tactical Tip - Building vendor/supplier relationships

Surviving Search, Closing the Deal, and Scaling a Business for the Long Haul - The Intentional Owner #2

Thu, 06 Mar 2025 08:00:00 -0000

Surviving 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 running a trades business, and the unexpected challenges of owner dependency in a company where the sellers were still climbing trees daily.

Other key insights include:

What it's really like to transition into an owner-operator role
The importance of hiring and structuring a team post-acquisition
Navigating the growing pains of shifting from survival mode to scaling
Why location and community connections matter more than you think

Whether you're considering entrepreneurship through acquisition or are in the trenches of running a small business, this episode is packed with real-world lessons from an owner who's lived it firsthand.

Links:

Kaustubh on LinkedIn - https://www.linkedin.com/in/kaustubh-deo/

Sam on X - https://x.com/Sam_Rosati

Topics:

(00:00:00) - Intro

(00:02:03) - Kaustubh's journey to ETA

(00:13:50) - Going under LOI on a business and losing it

(00:20:39) - Expectations vs. Reality in the day to day of running an acquired business

(00:27:53) - Discovering owner dependency

(00:32:21) - The importance of control in ETA

(00:35:19) - The Whack-a-Mole method

(00:40:47) - Sustainability is a false pretense early in ownership

(00:46:17) - Life owning a small business in your hometown

(00:52:37) - Tactical tips

Abandoning the Rat Race for SMB & ETA -The Intentional Owner #1

Thu, 27 Feb 2025 08:00:00 -0000

In 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 on X - https://x.com/Sam_Rosati

Watch this episode on YouTube - https://youtu.be/b2NbK-XP-bM

Topics:

(00:00:00) - Intro

(00:03:06) - The Journey to Small Business Ownership

(00:06:48) - From Law School to Big Law

(00:14:40) - The Decision to Pursue Entrepreneurship

(00:19:44) - Launching a Self-Funded Search

(00:30:10) - Starting the Search for a Business

(00:31:21) - Defining Roles and Strategies

(00:32:45) - Balancing Introversion and Leadership

(00:35:28) - Work-Life Balance and Career Choices

(00:39:23) - Operational Challenges and Solutions

(00:44:10) - Time Management and Productivity Tips

(00:52:21) - The Reality of SMB Ownership

(00:57:22) - Tactical Tips for Business Owners

Welcome to The Intentional Owner

Wed, 19 Feb 2025 16:09:00 -0000

Welcome 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.