The Intentional Owner

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

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

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

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

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