#473: John Bartlett | What Selling a Business Really Looks Like

Most owners don’t wake up wanting to sell their business. They wake up tired, overloaded, and unsure how much longer they can keep doing everything themselves. In this conversation, John Bartlett and I start by unpacking that reality — the moment when success on paper doesn’t feel like freedom, and selling starts to feel like the only option. 

From there, we zoom out and talk about what’s really going on beneath the surface: phantom wealth, misunderstood cash flow, and why many owners don’t actually see the full set of options available to them. We talk about how value is created, what actually drives multiples, and why clarity around cash flow and owner dependency changes everything. 

Only after that foundation is set do we walk through the real process of selling a company — what actually happens when you go to market, how deals are structured, how long it takes, where owners get surprised, and why the headline price is often the least important part of the transaction. This episode is about helping you see the whole landscape clearly — so whether you build, transition, or sell, you’re making an intentional decision instead of reacting out of exhaustion. 
 
John Bartlett is the founder of Brentwood Growth, where he helps owner-operators navigate valuation, growth, and M&A decisions with clarity and realism. A former serial entrepreneur, John grew and sold multiple businesses before becoming an advisor to lower middle-market owners. His work focuses on turning companies into durable assets—whether that means scaling, de-risking, or exiting on aligned terms. 

Top 10 Takeaways  

• Most owners don’t want to sell their business — they want relief from carrying everything themselves. 

• Phantom wealth is common: businesses look valuable on paper but don’t produce real freedom or liquidity. 

• Enterprise value is driven by adjusted EBITDA and the confidence buyers have in future cash flow. 

• Owner dependency is one of the biggest value killers, even in otherwise strong businesses. 

• Selling is not a moment — it’s a long, demanding process that reshapes the owner’s life for months or years. 

• Deal structure (taxes, earn-outs, rollover equity, timing) often matters more than the headline price. 

• Most owners dramatically underestimate how long a real M&A process takes and how consuming it is. 

• Buyers pay for predictability, not potential, and confidence in cash flow determines the multiple. 

• Owners who wait until burnout have fewer options and less leverage than they realize. 

• The best outcomes happen when owners understand their options early and choose intentionally, not reactively. 

Chapters:  

(00:00) Making a meaningful difference in business owners' lives and transitions 

(06:08) Three categories of sellers: burned out, transitioning, and scaling 

(10:40) Life as jigsaw puzzle: balancing financial and lifestyle goals 

(25:45) What owners really want is work-life balance and control 

(36:10) Valuation process: determining current worth and future potential value 

(46:10) Valuation fundamentals: adjusted EBITDA and multiple determine enterprise value 

(01:01:40) Complete M&A process timeline from teaser to final offers 

(01:10:10) Marathon hydration analogy: plan your exit before you're exhausted 

(01:14:00) Quality of earnings: the detailed due diligence cavity search 

(01:26:20) Critical difference between gross sale proceeds and after-tax reality 

(01:28:33) Lock business down within twelve months of planned sale 

 
Resources: 
John Bartlett LinkedIn: https://www.linkedin.com/in/johnl...

Chapters

• (00:00:00) - Independence by Design: Selling Your Company
• (00:01:55) - Why Business Owners Should Sell Their Companies
• (00:05:59) - Owners in Their 60s, 70s Should They Sell the
• (00:12:41) - Ownership: The 7 Levels of Growth
• (00:20:24) - Jack Stack on Ownership at 82
• (00:22:26) - Ownership vs Operator: The Problem
• (00:24:48) - Owner Operator Bifurcation
• (00:32:05) - Steve Ballentine on the Value of the Business
• (00:35:35) - Exploring the Value of the Business
• (00:43:30) - How to Win with a Size Client
• (00:43:49) - Private Equity Brokers: Enterprise Value of Companies
• (00:45:05) - Exploring the Multiple of a Private Business
• (00:50:43) - Adjusted EBITDA Multiple
• (00:57:55) - How To Find a Buyer for Your Startup
• (01:02:32) - Have You Validated Any Offer?
• (01:05:26) - Part 6: Hydration