Insurance Due Diligence in Small Business Acquisitions

The Guide to Information Sharing w/ Employees for SMB Owners

Kaustubh 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/ [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 [https://bay-biz.com] Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com [kd@sunthra.com] and they will answer them on the Pod!  Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first [https://bigdealsmallbusiness.substack.com/p/read-me-first] Sam on X - https://x.com/Sam_Rosati [https://x.com/Sam_Rosati] Topics:

Durability vs. Growth in Small Business Ownership

Kaustubh 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/ [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 [https://bay-biz.com] Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com [kd@sunthra.com] and they will answer them on the Pod!  Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first [https://bigdealsmallbusiness.substack.com/p/read-me-first] Sam on X - https://x.com/Sam_Rosati [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

Buying a Remote Business Through Self-Funded Search

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: * 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/ [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 [https://bay-biz.com] Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com [kd@sunthra.com] and they will answer them on the Pod!  Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first [https://bigdealsmallbusiness.substack.com/p/read-me-first] Sam on X - https://x.com/Sam_Rosati [https://x.com/Sam_Rosati] Links: Kalyn on LinkedIn - https://www.linkedin.com/in/kalynsaulsberry/ [https://www.linkedin.com/in/kalynsaulsberry/] Vince on LinkedIn - https://www.linkedin.com/in/vince-saulsberry-fong/ [https://www.linkedin.com/in/vince-saulsberry-fong/] Audience Synergy - https://audiencesynergy.com/ [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

Insurance Due Diligence in Small Business Acquisitions

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/ [https://www.newcorisk.com/] Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com [kd@sunthra.com] and they will answer them on the Pod!  Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first [https://bigdealsmallbusiness.substack.com/p/read-me-first] Sam on X - https://x.com/Sam_Rosati [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

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/⁠ [%E2%81%A0https://bay-biz.com/%E2%81%A0] Have SMB questions for Kaustubh and Sam? Email them to ⁠kd@sunthra.com [%E2%81%A0kd@sunthra.com]⁠ and they will answer them on the Pod! Links: Kaustubh on Substack - ⁠https://bigdealsmallbusiness.substack.com/p/read-me-first⁠ [%E2%81%A0https://bigdealsmallbusiness.substack.com/p/read-me-first%E2%81%A0] Sam on X - ⁠https://x.com/Sam_Rosati⁠ [https://x.com/Sam_Rosati%E2%81%A0] 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