#444: Understanding Main Street Valuations (Through the Buyer’s Lens)

If you're running a mid-sized company and considering acquisitions—or you just want to understand how smaller companies get valued—this episode is for you. 

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I sat down with Clint Fiore, a business broker who’s helped hundreds of Main Street businesses try to sell. And here’s the truth: most of them don’t get what they want. Not because their business is bad—but because it’s not built to be bought. 

We break down what actually happens when a $1–5M owner tries to exit: how they think, what they miss, and what buyers really see when they dig into the financials. Along the way, we talk through working capital expectations, earn-outs, founder dependency, and how to structure a deal that actually works. 

If you’re thinking about buying a business to grow—or you want a better understanding of how the lower market operates—this episode will give you the lens of a buyer and the clarity of someone who’s seen it all. 
 
Clint Fiore is the founder of Bison Business, a boutique M&A advisory firm that helps owners sell their companies and buyers find the right opportunities in the lower middle market. With experience as both an entrepreneur and a broker, Clint has built, scaled, and sold companies—and now helps others do the same. He’s personally advised on hundreds of deals, from owner-operated shops to more complex transactions, and he knows what buyers care about: clean financials, transferable operations, and a clear path to post-close success. Before founding Bison, Clint built and exited a national consumer brand, led sales in high-growth tech, and served aviation clients as a top commercial broker. In addition to leading Bison, Clint is developing Dealonomy—a new platform designed to modernize the small business deal marketplace by combining tech, transparency, and relationship-based brokerage. He’s also a private pilot, father of four, and a lifelong entrepreneur who brings a grounded, no-BS perspective to buying and selling businesses. 
 

Chapters:  

• (00:00) Introduction and catching up with Clint Fiore's remarkable journey 

• (01:28) From aviation dreams to entrepreneurship through insurance industry insights 

• (12:24) The business brokerage pivot and learning deal complexity firsthand 

• (21:04) Creating the hundred million dollar offer and zero commission model 

• (28:04) SDE versus EBITDA and the harsh realities of main street valuations 

• (38:30) Compassionate bubble bursting and managing seller expectations realistically 

• (50:15) The whale shark strategy for acquisition and market consolidation 

• (01:03:18) Launch of Deal Nominee platform and the future of business transactions 

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

 

Resources: 
 
Bison Business Brokers – http://lackbeltmembers.com 

Clint’s LinkedIn - https://www.linkedin.com/in/clintfiore/ 

Ryan Tansom Website