#440: Cash, Risk, and the Real Reason Most Deals Fall Apart with Elliott Holland

This episode is fire. Elliott Holland is a straight shooter who has seen hundreds of deals from every angle—searcher, investor, operator, and QofE provider. In this conversation, we cut through the noise to talk about what’s really going on in the acquisition market, why most self-funded searchers fail, and how owners can actually position their business (and themselves) for the next chapter. 

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We dig into why most companies don’t cash flow the way owners think they do, how the wrong expectations destroy good deals, and what it takes to bridge the gap between buyers and sellers. Elliott shares what he’s seeing across the market through his firm Guardian Due Diligence, why real cash matters more than reported EBITDA, and what kind of leaders are needed to keep growing Main Street businesses when the owner steps away. 
 

Whether you're trying to step back, prepare for an exit, or find the right leader to replace you, this episode reframes how to think about buyers, successors, and what actually makes a company valuable in today's market. It's a must-listen if you're planning your next move—or still figuring out what it should be. 
 
This conversation ties directly into the Elevate phase of the iBD™ Magic Model—helping owners replace themselves, build strategic leadership, and unlock true independence across time, cash flow, and equity. 
 
Key Takeaways 

- Cash is king, not EBITDA. Owners need real cash flow clarity before thinking about transitions, exits, or valuations. 

- Searchers aren’t the enemy—they’re the key. When structured properly, acquisition entrepreneurs may be the best shot at long-term succession. 

- The traditional brokered exit path is broken. Creative deal structures, mentorship windows, and phased transitions are underutilized but powerful. 

- Risk must be shared. Deals fall apart when expectations aren’t aligned and buyers are asked to shoulder too much risk without support. 

- Succession planning starts now. The sooner you clean up your numbers and clarify your leadership gap, the more optionality you’ll create. 

 
Elliott Holland is the founder of Guardian Due Diligence, where he helps acquisition entrepreneurs avoid lemons and close deals with confidence. He’s reviewed hundreds of financials, run his own deals, and coached dozens of buyers through the self-funded acquisition gauntlet. Elliott’s no-BS approach cuts through bad data, bad deals, and bad advice—and his coaching programs help real operators buy real businesses the right way. With deep roots in private equity, small business ownership, and financial diligence, Elliott brings the rare perspective of someone who’s seen both sides of the table and knows what it really takes to succeed. 

 
Chapters:  

• (00:00) How Elliott built a seven-figure business with zero employees 

• (06:05) SBA loan changes and their impact on the acquisition market 

• (08:52) US business landscape: key market statistics and buyer-seller dynamics 

• (13:18) Small business valuations vs retirement needs: the math problem 

• (17:55) Signal vs noise: cutting through marketing hype in entrepreneurship