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

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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
(00:02:34) - 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