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

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:

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 (00:01:22) - 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

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

MORE:

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:

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 (00:01:12) - 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

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

They discuss:

• How Kaustubh and Sam would advise their younger entrepreneurial selves

• Why comparisons with peers can both motivate and distract

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

• Lessons learned from early management challenges and evolving values

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

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

• How long term financial security shapes decisions and personal fulfillment

Support our Sponsors:

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

Website: https://www.thekalmargroup.com

Twitter: https://x.com/thesmbrecruiter

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

Aspen HR

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

Links:

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

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

Topics:

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

Mark Sinatra joins Sam Rosati and Kaustubh Deo to reflect on his 15-year journey through entrepreneurship, search funds, and leadership. From launching his first search in 2007 to navigating the 2008 financial crisis as a new CEO, Mark shares how perseverance, self-discipline, and purpose carried him through some of the most difficult chapters of his business life. He discusses building resilience during downturns, the evolution of the ETA ecosystem, and how his experiences led him to his current role at Aspen HR, where he helps professionalize HR operations for small and mid-sized companies.

They discuss: • How Mark discovered the search fund model and built conviction to pursue it • Navigating the 2008 financial crisis just months after acquiring his first company • Lessons learned from employee turnover, client loss, and leadership under pressure • Why physical and mental health are essential to sustaining long-term success • The transition from owner-operator to investor and executive at Aspen HR

Links:

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

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

Mark on LinkedIn - https://www.linkedin.com/in/msinatra/

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

Topics:

(00:00:00) - Intro (00:02:23) - Mark's career and background (00:07:24) - Launching a search fund (00:13:53) - Navigating the Great Financial Crisis (00:21:17) - Operational challenges and employee turnover (00:24:44) - Inflection point and recovery (00:33:03) - Building a strong management team (00:35:50) - Navigating non-linear business paths (00:41:04) - Winning competitive deals (00:43:28) - Insights from investors and turning points (00:47:24) - Challenges of change management (00:49:56) - Joining Aspen HR during the pandemic (00:52:40) - Aspen HR's business model and client focus (01:03:37) - PEO model explained (01:07:54) - Advice for searchers and operators