In this episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati reconnect after a busy stretch that included SMBash and the Masters to reflect on what made this year’s event the best one yet. They dive into the evolution of SMBash, from its scrappy beginnings during the pandemic to a thoughtfully curated gathering that now draws operators, searchers, and investors from across the country.

Kaustubh and Sam discuss what’s changed about the event, why the mix of attendees felt refreshingly diverse, and how the conference has become a cornerstone for the ETA community. They reflect on standout keynotes from voices like Brent Beshore and Moses Kagan, lessons from building community outside of business, and the value of stepping outside your industry to gain perspective.

Also in this episode:

• Behind-the-scenes of organizing SMBash and why it continues each year

• The tension between being too in the weeds vs. too far removed as an operator

• How Kaustubh applies lessons from peer groups in other industries to Blooma Tree Services

• The challenge of managing growth, KPIs, and people when scaling a small business

• Why community building in SMB often fills the role of religion or tribe for many entrepreneurs

• A discussion on shared services, equity incentives, and decentralization in holdco structures

This episode blends event recap with personal insight, practical lessons, and a candid look at the realities of operating and building in the world of small business.

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

(00:01:07) - The Masters

(00:09:16) - SMBash recap

(00:20:11) - Why Kaustubh joins national organizations

(00:24:13) - Does being in the weeds to much take away from working “on” the business?

(00:27:13) - Recapping Kaustubh’s KPI Presentation

(00:31:55) - How to improve SMBash

(00:36:21) - Why do you go to SMBash?

(00:38:15) - Wishlist for SMBash 2026

(00:42:21) - Dealing with Tax returns