Podcast
The Intentional Owner
Hosted by Kaustubh Deo & Sam Rosati · EN
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.
35episodes
Episodes
Newest firstAll episodes
The Guide to Information Sharing w/ Employees for SMB Owners
4d ago01:01:25Tap to summarizeKaustubh Deo and Sam Rosati unpack the complicated balance between transparency and confidentiality as small business owners managing growing teams. They explore how much financial and operational information should actually be shared with employees, where the line exists between helpful transparency and unnecessary stress, and why many owners unintentionally create confusion by failing to define what information is confidential. The conversation moves beyond theory into practical examples from their own businesses, including SBA debt, KPI dashboards, compensation structures, equipment purchasing decisions, and the realities of managing perception inside small companies. They also discuss how the search fund playbook has changed dramatically since 2021 and why many traditional acquisition assumptions no longer work in today’s market. They discuss: • The tradeoffs between transparency and oversharing with employees• Why KPI visibility should align directly with what each team member can control • How SBA debt and rising interest rates shape owner decision making• The danger of employees making assumptions when owners communicate too little • Why equity compensation often fails to create “owner mentality” in small businesses • The importance of clearly defining what information is confidential internally • How today’s acquisition environment differs from the low-rate search fund boom years • The four “horsemen” of bad deals in the current ETA market This episode is valuable for operators, searchers, and small business owners trying to build trust with teams while navigating the financial realities of ownership. 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 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:
Transcribe →Durability vs. Growth in Small Business Ownership
3w ago00:57:30Tap to summarizeKaustubh 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 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(00:03:01) - 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
Transcribe →Buying a Remote Business Through Self-Funded Search
Apr 3001:14:53Tap to summarizeSam 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 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 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
Transcribe →Insurance Due Diligence in Small Business Acquisitions
Apr 1600:54:58Tap to summarizeSam 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 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(00:02:34) - 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
Transcribe →Making Smarter Financial Decisions in Your SMB with Michael Young
Apr 200:49:38Tap to summarizeIn 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
Transcribe →The Financial Controls Every Small Business Needs w/ Denisse Montenegro - TIO #34
Mar 1901:17:28Tap to summarizeIn 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
Transcribe →Self-Funded ETA vs. Independent Sponsorship - The Intentional Owner #33
Mar 500:56:32Tap to summarizeIn 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
Transcribe →A Weekly Time Audit for Small Business Owners - The Intentional Owner #32
Feb 1900:59:02Tap to summarizeSam 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
Transcribe →The Real Tradeoffs Between Operating and Investing - Mike Botkin - The Intentional Owner #31
Feb 501:15:23Tap to summarizeIn 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...
Transcribe →The Real Tradeoffs Between Operating and Investing - Mike Botkin - The Intentional Owner #31
Feb 501:15:22Tap to summarizeIn 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
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