#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 

• (21:15) Cash vs EBITDA: the fundamental truth of business transactions 

• (30:37) The Independence Flywheel: balancing time, cash flow and equity 

• (37:19) AI and clear principles: the keys to better business decision-making 

• (47:30) The leadership gap: finding qualified executives in today's market 

• (54:31) Creative acquisition models: partial buyouts and leadership transitions 

• (1:04:15) Reconciling business owner goals with financial realities 

• (1:14:15) The war for talent and identifying unicorn executives 

• (1:23:00) Bridging the gap between owners and acquisition entrepreneurs 

• (1:32:00) Building trust and shared risk in business succession planning 

• (1:38:00) The importance of deep conversations and earned freedom 

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

 

Ryan Tansom is a seasoned entrepreneur, speaker, and the founder of Independence by Design™, a transformative ownership framework for growth-oriented business owners. After turning around and selling his family business in an eight-figure exit, Ryan spent over a decade dissecting the lessons learned from his journey. His mission is to help other business owners avoid the pitfalls he encountered by providing them with the tools and knowledge to align their business operations with their personal and financial goals. 

With a deep understanding of the challenges faced by owner-operators, Ryan developed Independence by Design™ to empower owner-operators to create sustainable cash flow, grow their company’s equity value, and achieve true independence. He has shared his insights on hundreds of stages, including Vistage, EO, and industry associations, and has reached over 500,000 listeners through his podcast. 

Ryan is passionate about helping business owners get unstuck from the day-to-day grind and design a business that serves their life, not the other way around. 

Resources: 
Elliott Holland LinkedIn: https://www.linkedin.com/in/elliottholland/ 
Guardian Due Diligence: https://www.guardianduediligence.com 
The Business Buying Masterclass: https://www.businessbuymasterclass.com 
IBD Owner’s Scorecard: Time, Cash Flow, Equity trade-offs https://ryantansom.com/clarify-goals 
Independence by Design™ Workshop: https://ryantansom.com/independence-by-design-workshop  
Independence by Design™ Ownership Coaching: Ryan Tansom’s Ownership Accelerator programs and coaching https://ryantansom.com/coaching 
Ryan Tansom Website https://ryantansom.com/ 
Ryan Tansom LinkedIn https://www.linkedin.com/in/ryantansom/ 
Ryan Tansom Twitter https://twitter.com/RyanTansom 
Ryan Tansom YouTube https://www.youtube.com/@ryantansom 
Ryan Tansom 30-Minute Ownership Strategy Call https://calendar.app.google/tsKk7z6ohugDchWq8 

 
Sound Bites 

“EBITDA doesn’t pay the debt. Cash does.” 

“Owners want out. Acquisition entrepreneurs want in. There’s a massive opportunity to meet in the middle—if we structure it right.” 

“Most people are fishing in a pond with no fish. Then they blame the bait.” 

“You don’t just buy the business. You buy the risk. And the risk has to be shared.”