#476: Tom Shipley | Why Most Owners Get Stuck at $1–$2M EBITDA (and How to Break Through)

This conversation with Tom Shipley goes far beyond “growth” or “M&A tactics.” It’s about understanding the real game of ownership — how value is actually created, how capital really works, and why most owners unknowingly trap themselves by optimizing the wrong things. 

We start by reframing business as a finite game of time, energy, and capital. Tom shares how his background in Special Forces shaped his approach to leadership, resourcefulness, and decision-making — and how those principles carried into building, acquiring, and ultimately selling businesses. 

From there, we go deep into the mechanics most owners never truly understand: valuation, EBITDA vs. cash flow, multiple expansion, acquisition strategy, and deal structure. Tom breaks down how value is created before the exit, why fundamentals matter more than hype, and how acquisitions can create real wealth — or destroy it — depending on how they’re done. 

We end with one of the most important insights in the episode: the “valley of despair” facing owners with $1–$2M EBITDA, and Tom’s merge-to-exit model designed to help founders escape it by building scale, optionality, and alignment before they sell. 

Tom Shipley is a serial entrepreneur and M&A expert with 20+ years scaling brands to $2B+ in sales via D2C, Amazon, and retail giants like Costco and Ulta. A "lone soldier" in Israel's elite IDF Unit 669, he bootstrapped Atlantic Coast Brands to $100M (exited 2021), raised $100M for Foundry (e-com aggregator), and founded AVA Acquisitions for digital agencies. Now, via Deal Boardroom and bi-annual DealCon Summit, he empowers founders to acquire, scale, and exit—often with $0 down. Host of Deal Playbook podcast, Shipley splits time between Austin and Tel Aviv, mentoring hyper-growth via Shipley Capital. 

Top 10 Takeaways 

• Ownership is a finite game — time, energy, and capital are limited, so priorities must be chosen deliberately. 

• Great leaders optimize for resourcefulness, not resources, especially when conditions get constrained. 

• EBITDA and cash flow serve different purposes: cash is survival, EBITDA is valuation. 

• Revenue growth without fundamentals often destroys value instead of creating it. 

• Valuation is ultimately about confidence in future cash flows, not past performance. 

• Multiple expansion is one of the most powerful — and misunderstood — wealth creation tools in business. 

• Acquisitions create value only when they are strategically complementary, not just additive. 

• Poor integration turns acquisitions into “Frankenstein” businesses that collapse under complexity. 

• Most $1–$2M EBITDA owners are stuck in a no-man’s land where selling doesn’t deliver real freedom. 

• Merging before exiting can dramatically increase the probability, multiple, and outcome of a successful sale. 

 
Chapters:  
(00:00) Introduction of Tom Shipley and discussion of acquisition strategies 

(02:37) Finite resources require prioritizing impact, adventure, and resourcefulness 

(07:10) Writing your own epic novel with five-year chapters 

(09:40) Buying businesses without cash using creative deal structures 

(12:16) Special Forces lessons on resourcefulness, tenacity, and team leadership 

(21:30) Valuation fundamentals and confidence in future cash flows 

(35:00) Multiple expansion and compounding value through strategic acquisitions 

(43:32) Strategic fit and avoiding Frankenstein rollups in acquisitions 

(55:13) Integration work upfront generates cash flow versus Frankenstein EBITDA 

(58:36) Where to find Tom Shipley and information on Dealcon 
 
Resources: 
Tom Shipley LinkedIn: https://www.linkedin.com/in/t-shipley/ 
Ryan Tansom Website https://ryantansom.com/