In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati unpack one of the most important and nuanced decisions a small business buyer can make: whether to self-fund and retain 100% ownership or raise equity from outside investors.

Drawing from their own experiences and those of other operators, Kaustubh and Sam explore how this decision impacts governance, financial flexibility, and long-term strategy. They get into the real trade-offs between maximizing ownership and building in room to breathe—especially when it comes to leverage, personal guarantees, and navigating the stress of early-stage operations.

They also dive into:

• How much control investors should have—and where to draw the line
• The importance of aligning investor involvement with expectations up front
• Building informal and formal support systems around the CEO
• What makes an ideal investor profile and cap table structure
• How investor communication and transparency affect outcomes
• Why having the ability to sell—or step back—should always remain with the operator

This episode is full of practical advice for searchers, operators, and investors who want to better understand the dynamics behind ownership structure, investor relationships, and long-term alignment.

Links:

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

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

Topics:

(00:00) - Intro

(00:01:30) - Catching up after vacation

(00:11:21) - Self-funding vs. Raising money in acquiring businesses

(00:18:00) - The pros of owning 100% of a business

(00:23:28) - Advisory boards

(00:24:48) - Is there a “right” number or mix of investors?

(00;27:35) - Finding mentors

(00:30:11) - Paying for consulting

(00:33:01) - Investor mindset towards returns

(00:39:53) - Investor communication

(00:49:38) - Governance

(00:56:34) - Should a Searcher be able to do work outside of the business they just bought?

(00:59:07) - If you could only choose one profile of investor, what would the ideal be?