Every owner’s journey is made up of inflection points, the moments where you have to make big, irreversible decisions. 
 
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In this episode, my friend Tom Nagler shares his full story arc as an owner. From growing up in a family business, to buying it from his dad, to juggling cash and growth pains, to considering a sale but choosing to acquire instead, to bringing on a partner, and finally making the hard decision to sell — Tom lived through the full journey of ownership.  
 
What makes Tom’s story powerful is how openly he shares both the human side and the technical side of those decisions. He talks about family dynamics, cash pressure, risk, and identity — but also about valuations, deal structures, and what actually creates value in a company. He also reflects on how education, an ownership framework, and clarity gave him the confidence to understand his options and choose intentionally at each step. 
 
If you’re an owner navigating the day-to-day grind, facing big decisions, or just wondering what the road ahead might look like, Tom’s story will give you a clear window into the full arc of ownership — and the lessons you can carry into your own journey. 

What We Covered: 
Growing up in the family business and deciding to buy it from his dad 
The reality of juggling cash flow, debt, and growth pains 
The moment he considered selling — and why he chose to acquire instead 
Bringing on a partner and how it reshaped the business 
How he approached his valuation and learned to understand what really drives value 
The difficult decision to sell — and how he and his family worked through it 
What life and perspective look like after the business 

Tom Nagler is a former business owner who grew up in a family company, later bought it from his father, and spent years navigating the challenges of cash flow, growth, acquisitions, and partnerships. Through a series of major inflection points, he gained a deep understanding of valuation and what truly drives company value. After ultimately selling his business, Tom now shares candid lessons from the full arc of ownership — from family handoff to life after the sale. 

Chapters:  

Resources: 
Tom Nagler LinkedIn https://www.linkedin.com/in/tomnagler/ 
Ryan Tansom Website https://ryantansom.com/