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:  

• (00:00 ) Introduction of guest Tom Nagler 

• (05:22 ) Joining the family business, early career decision making process 

• (17:14 ) Father-son dynamics and building complementary business partnership skills 

• (27:06 ) Building company culture, values and hiring the right people 

• (41:15 ) Managing cash flow challenges and capital intensive business growth 

• (51:51 ) First acquisition offers and decision to decline early exit 

• (01:18:19 ) Strategic acquisition of supplier, vertical integration and lessons learned 

• (01:28:02 ) COVID impact on diagnostics business and final sale opportunity 

• (01:32:03 ) Working with Ryan on exit planning and decision framework 

• (01:44:24 ) Post-sale reflections, lessons learned and advice for business owners 

• Rate, comment, and share with the owner/operators you know! 

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Chapters

• (00:00:00 ) - Independence by Design: The Full Story arc
• (00:02:37 ) - Tom Brokaw on His Personal
• (00:04:48 ) - Tom Flannery on Starting and Selling a Plastics Business
• (00:07:47 ) - Snowmobile Shield Making in the Twin Cities
• (00:09:21 ) - Going to Business School With My Dad
• (00:12:13 ) - Tom on the Importance of Family Business
• (00:14:34 ) - Multiple People Tell The Same Story
• (00:17:06 ) - On The Differance With His Dad
• (00:19:42 ) - On The Transition at YouTube
• (00:22:30 ) - Tom Walton on Going From Dad to Owner
• (00:27:31 ) - In the Elevator With My Business Partner
• (00:30:08 ) - The Secret Life Of Working At a Startup
• (00:31:39 ) - In the Elevator With Dave Ramsey
• (00:36:52 ) - Ryan on The Hard Decisions
• (00:40:49 ) - Expert Talk: Cash Flow
• (00:45:22 ) - How to Manage Your Own Psychology
• (00:49:10 ) - Tom Clancy on The Fear of Making a Decisive Decision
• (00:51:37 ) - How My Dad Passed Away In 2016
• (00:56:14 ) - In the Elevator With Tom Cruise
• (00:56:58 ) - Credible Offer for GE's CEO
• (00:57:35 ) - Decision Tree: Ownership Value
• (01:00:35 ) - Why I Didn't Sell My Company
• (01:03:09 ) - Tom Clancy on Why He Doesn't Regret the Sale
• (01:04:41 ) - How to Acquire a Tool Making Business
• (01:08:22 ) - Integrated Molding: The Hard Part
• (01:12:12 ) - Executive Compensation and the Leverage
• (01:17:03 ) - The Right to Behave
• (01:18:10 ) - Why we Bought Covid.
• (01:23:20 ) - In the Elevator With Tom Cruise
• (01:27:12 ) - On The Sell vs. Buy Decision
• (01:32:45 ) - The Importance of Regret
• (01:37:18 ) - In the Elevator With Warren Buffett
• (01:41:05 ) - Ryan on Financial Fear
• (01:42:51 ) - Post-Expiry Capital Decisions
• (01:48:33 ) - "To Trust Yourself"
• (01:49:28 ) - How to Manage Your Time
• (01:53:43 ) - What Your Dad Would Have Thought of The Dragon Project