In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo dive deep into the critical first 90 days following a business acquisition. Drawing from their own operating experience, they discuss tactical items like transition checklists and asset conversion, while also exploring the softer—but equally important—aspects of communication with employees and customers. They examine the nuances of announcing a deal, managing early team dynamics, and the risk of misaligned retention strategies. Along the way, they share candid reflections on the evolving identity of a business owner and the long road to earning trust and building cultural buy-in.

They discuss:

• Practical challenges and checklists for the first week of an asset deal transition

• Strategic communication approaches for customers and employees post-close

• Why retention bonuses can backfire and what to consider instead

• The long timeline and emotional complexity of "owning" a business culturally

• How to assess operator readiness in self-funded search deals

A valuable episode for anyone navigating the early stages of ownership or evaluating what it really means to lead a small business.

Links:

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Follow along with the guys' fitness tracker! - https://bit.ly/3T4EpHw

Topics:

(00:00:00) - Intro

(00:01:05) - Catching up

(00:06:26) - First 90 days post-acquisition

(00:16:03) - Communication with the team

(00:22:58) - Retention bonuses

(00:32:26) - The moment an acquirer feels like the business has become their own

(00:38:47) - Feeling like you’ve earned the team’s trust, such that you can make fundamental changes

(00:50:25) - Becoming better at assessing potential operators

In this episode of The Intentional Owner, Kaustubh Deo and Sam Rosati dive deep into the often-overlooked art of managing investors in self-funded search deals. From communication best practices to governance structures, Kaustubh and Sam explore the nuances that define healthy investor relationships. They share personal experiences, trade perspectives as both operators and investors, and offer candid commentary on what it really takes to build trust and discipline in capital partnerships. The conversation also touches on capital structuring, ownership dynamics, and how to thoughtfully balance investor involvement.

They also discuss:

* Common pitfalls searchers face when managing investor relationships

* The difference between defensive deal-making and thoughtful diligence

* How investor reporting impacts long-term cost of capital

* Trade-offs of working with active vs. passive investors and mini-funds

* Real-world insights on liquidity rights, put/call structures, and governance

A must-listen for searchers and owners seeking to build disciplined, long-term relationships with capital partners.

Links:

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Follow along with the guys' fitness tracker! - https://bit.ly/3T4EpHw

Topics:

(00:00:00) - Intro

(00:01:05) - Recapping the week

(00:16:00) - Kaustub’s investor set up

(00:20:32) - Passive vs. active investors

(00:30:41) - Liquidity rights

(00:39:19) - What is the “right” check size?

(00:43:06) - Sam’s investing style

(00:45:35) - Board philosophies

(00:48;19) - Types of People who can be useful to searchers as investors

(00:51:09) - Tactical tip of the week

Quick Update for the listeners! We're excited to announce that we will soon be bringing guests onto the show, as well as moving to a release cadence of every other week. See you next Thursday!