From Zero to $138M: Tim O’Brien’s Blueprint for Building a Business That Lasts

Ever wonder why some businesses thrive during economic chaos while others collapse? Many believe success in the trades comes from luck or endless hustle, but the truth is discipline, systems, and culture determine survival. 

In this episode of The Better Than Rich Show, host Mike Abramowitz sits down with Tim O’Brien, founder of Tim O’Brien Homes, who shares how launching a homebuilding company during the Great Recession became his greatest advantage. He unpacks how faith-based principles of stewardship, integrity, and servant leadership fueled his growth from zero to $138 million. From building long-term trade partnerships and defining company values to using the Entrepreneurial Operating System (EOS) for sustainable scale, O’Brien shows how simplicity, trust, and vision create businesses that last. 

Timestamps:  

[00:00] Starting from Zero During a Recession 
[07:00] Building Brand Awareness with No Budget 
[11:00] Culture Before Scale 
[16:00] Hiring and Delegation Lessons 
[20:00] Communication Cadence and the EOS Revolution 
[27:00] The Trade Council Blueprint 
[33:00] Empowering Trades Through Shared Values 
[43:00] How to Get the Attention of a $138M General Contractor 
[48:00] Scaling from $25M to $138M 
[54:00] Simplicity, Sustainability, and Freedom of Time 

Key Quotes 

• “You can’t lead from the valley; you have to get up on the hill to see what’s really going on.” 
   

• “We’re in the people business. We just happen to build homes.” 
   

• “Culture isn’t a slogan—it’s a system that decides who stays and who leaves.” 
   

• “Your best trade partners aren’t your vendors, they’re your collaborators.” 
   

• “Freedom of time is the ultimate wealth.” 

Key Takeaways 

Links Mentioned