The Intentional Owner

Kaustubh Deo & Sam Rosati
  • 5.0 (12)
  • CAREERS
  • UPDATED BIWEEKLY

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 for yourself, for your family, for your employees, and for your community. We love everything to do with small business acquisitions & entrepreneurship and want to support our fellow small business owners in having a fulfilling life.

  1. APR 2

    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 ⁠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

    50 min

  2. MAR 19

    The 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 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

    1h 17m

  3. MAR 5

    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 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

    57 min

  4. FEB 19

    A 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 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

    59 min

  5. FEB 5

    The 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

    1h 15m

  6. JAN 22

    Buying 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, 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

    1 hr

  7. JAN 8

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

    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, 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

    58 min

  8. 12/18/2025

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

    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, 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

    54 min
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Trailer

5
out of 5
12 Ratings

About

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 for yourself, for your family, for your employees, and for your community. We love everything to do with small business acquisitions & entrepreneurship and want to support our fellow small business owners in having a fulfilling life.

Information

  • Creator
    Kaustubh Deo & Sam Rosati
  • Years Active
    2025 - 2026
  • Episodes
    37
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    The Intentional Owner

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