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:

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

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

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.

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

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:

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

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

#TheIntentionalOwner #TIO #SMB

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:

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

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:

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

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

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:

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

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:

The Kalmar Group is a recruitment firm who partners with small business owners around the nation to find Manager to VP level hires in sales, marketing, operations, and finance across multiple niche industries.

Website: https://www.thekalmargroup.com

Twitter: https://x.com/thesmbrecruiter

LinkedIn: https://www.linkedin.com/in/dylanscroggins/

Aspen HR

Please contact our valued sponsor Aspen HR (www.aspenhr.com, [email protected]) for a quote on PEO services and a complimentary HR due diligence assessment

Links:

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

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

Topics:

(00:00:00) - Intro (00:02:00) - 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