In this special live episode of The Intentional Owner, co-hosts Kaustubh Deo and Sam Rosati take the stage at SMBash in Dallas for a wide-ranging, honest, and often humorous conversation with two operators who’ve taken very different paths into small business ownership.

First up is Chris Williams, owner of System Six, who shares how he transitioned from investment banking and private equity to running a remote bookkeeping and finance operations firm. Chris opens up about the real motivations that led him to entrepreneurship, the challenges of stepping into the CEO role, and how becoming a new father has shaped his perspective on work-life balance, time management, and the long game of ownership.

Later in the episode, they’re joined by Jeff Driskel, a current NFL quarterback and co-founder of Four Pillars Group, an independent sponsor platform. Jeff talks about balancing pro football with building a portfolio of small businesses, the surprising overlap between athletics and entrepreneurship, and what it’s been like running a company alongside his brother. He also shares lessons on discipline, learning new systems, and how he's using the trust he’s built in the locker room to raise capital and source operators.

This episode covers:

• Why people choose the small business path—and how that motivation evolves
• The highs and lows of parenting while owning and growing a business
• Building companies with family and managing partnership dynamics
• Operator-first investing and how to find the right fit between people and businesses
• The importance of long-term thinking, pattern recognition, and staying power in ETA

Recorded live, this conversation blends real stories, practical advice, and a behind-the-scenes look at what it truly means to build a life—and a business—with intention.

 

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

(00:01:23) - Chris Williams' journey and motivations 

(00:05:15) - Balancing business and personal life 

(00:17:28) - Jeff Driscoll's background and transition to ETA 

(00:21:49) - The secret sauce to success 

(00:21:58) - Transitioning from football to business 

(00:24:24) - Working with family 

(00:25:19) - Choosing the right business 

(00:27:46) - Finding the right people 

(00:31:05) - Leveraging football for business success 

(00:34:44) - Lessons from football 

(00:40:46) - Adapting to new teams and systems