The Intentional Owner

By Kaustubh Deo & Sam RosatiBusiness Careers

The Intentional Owner episodes

May 14Durability vs. Growth in Small Business Ownership
Kaustubh Deo and Sam Rosati examine the hard tradeoffs that come with building a service business for durability instead of chasing the highest possible annual earnings. They discuss Q1 planning, seasonality, backlog pressure, pricing strategy, crew utilization, and the operational leverage that shows up when a business adds capacity without adding overhead. Kaustubh walks through how he is thinking about seasonal pricing, commercial work, delegation, and the choice to optimize for a well-run business that can still exist 10 years from now.

They discuss:
Why seasonal pricing may matter more than blanket advice to raise prices

How adding a fourth crew changes margin math, capacity planning, and backlog pressure

The tradeoff between higher annual earnings and a smoother, more durable business

Why owner bottlenecks often remain in HR, accounting, sales meetings, and growth systems

How commercial work, pricing discipline, and delegation can support the path to a five-crew business
Support our Sponsors:
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 [email protected] 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
(00:03:01) - Listener Questions Grab Bag
(00:04:01) - Why Q1 Feels Brutal
(00:06:06) - Seasonality And Lead Gen
(00:12:30) - Vacation Backlog Problem
(00:13:59) - Recurring Meeting Cleanup
(00:15:08) - Sales Meeting Bottleneck
(00:16:37) - Can AI Replace You?
(00:19:27) - Seasonal Pricing Strategy
(00:31:01) - Scale Vs. Price Hikes
(00:32:19) - Seasonal Layoffs Dilemma
(00:38:50) - Choosing Stability Over Peaks
(00:40:17) - Service Adjacencies Brainstorm
(00:53:24) - Sales Systems And Constraints
58 min
April 30Buying a Remote Business Through Self-Funded Search
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 [email protected] 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
1 hr 15 min
April 16 Insurance Due Diligence in Small Business Acquisitions
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:
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/
Have SMB questions for Kaustubh and Sam? Email them to [email protected] 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
55 min
April 02 Making Smarter Financial Decisions in Your SMB with Michael Young
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 ⁠[email protected]⁠ 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
50 min
March 19The Financial Controls Every Small Business Needs w/ Denisse Montenegro - TIO #34
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/
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/
Have SMB questions for Kaustubh and Sam? Email them to [email protected] 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
1 hr 18 min
March 05 Self-Funded ETA vs. Independent Sponsorship - The Intentional Owner #33
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:
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/
Have SMB questions for Kaustubh and Sam? Email them to [email protected] 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
57 min
February 19A Weekly Time Audit for Small Business Owners - The Intentional Owner #32
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:
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/
Have SMB questions for Kaustubh and Sam? Email them to [email protected] 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
1 hr
February 05The Real Tradeoffs Between Operating and Investing - Mike Botkin - The Intentional Owner #31
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
1 hr 16 min
January 23Buying a Business Means Owning the Sales Function with Andrew Gazdecki of Acquire.com - The Intentional Owner #30
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, ⁠[email protected]⁠) for a quote on PEO services and a complimentary HR due diligence assessment

Links:

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

Sam on X - ⁠https://x.com/Sam_Rosati⁠

Topics:

(00:00:00) - Intro (00:01:03) - 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
1 hr 1 min
January 22Buying a Business Means Owning the Sales Function with Andrew Gazdecki of Acquire.com - The Intentional Owner #30
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, [email protected]) for a quote on PEO services and a complimentary HR due diligence assessment
Links:
Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first
Sam on X - https://x.com/Sam_Rosati
Topics:
(00:00:00) - Intro
(00:01:03) - 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
1 hr 1 min

About The Intentional Owner

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The Intentional Owner provides an in-depth & personal look at life as a small business owner. We discuss how to acquire, operate, and grow small businesses in ways that achieve positive impacts…