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!

In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati unpack what it looks like to build a fulfilling life around small business ownership without sacrificing long-term goals. Framed around personal goal setting, competing priorities, and everyday tradeoffs, the episode offers a candid look at how both hosts are trying to design lives that support sustainability—not just scale.

They share stories of recent chaos, from moving mishaps and work-life boundaries to surprise break-ins and activity trackers, all while reflecting on how much structure is enough to keep life moving forward without being overly rigid.

They also discuss:

• The tension between goal-setting and adaptability in both life and business

• How to balance ambition with long-term personal sustainability

• Frameworks like EOS and the Vision Traction Organizer for business planning

• The opportunity cost of hobbies and how personal priorities evolve with family

• Leveraging tools like KPI dashboards and Google Sheets for operational clarity

• The importance of community, fitness, and calendaring for intentional living

This episode is a thoughtful, unfiltered conversation for anyone navigating the overlap between business ownership, relationships, and building a meaningful life—one decision at a time.

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

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

Topics:

(00:00:00) - Intro

(00:01:08) - Catching up

(00:14:39) - Setting meaningful goals

(00:20:34) - BHAGs

(00:22:47) - M&A Approaches

(00:26:53) - Goal setting at Blooma and at home

(00:33:48) - Maintaing friendships

(00:45:35) - Living with a long-distance SO

(00:48:50) - Priority tradeoffs