Elliott Holland: Why 90% of Business Buyers Fail

Elliott Holland is a Harvard Business School graduate and veteran of small business acquisitions, and we spoke about why most aspiring business buyers never close a deal—and what you can do differently.

With over 15 years in the trenches as a buyer, advisor, and coach, Elliott brings real talk to a world filled with overhyped promises and group-cohort gimmicks. “90% of business buyers never get a deal done. But that doesn’t have to be you,” he tells us. So what separates the 10% who succeed?

We covered the messy reality behind the glossy dream: how corporate professionals earning $200–400K annually struggle to make the leap to business ownership, not due to lack of talent—but because they enter a completely new game without the right training, time, or tactical support.

Key themes we explored:

• Why self-learning or group courses fall short when you're negotiating $3–7M deals
  
  
• The psychological leap from “safe employee” to “deal-making owner”
  
  
• Why mastering BS detection is more valuable than spreadsheets
  
  
• The brutal truth about due diligence, valuation, and seller games
  
  
• How one-on-one coaching can compress 30 years of learning into 6 months
  
  

As Elliott puts it:

“You don’t go from negotiating $20,000 salary bumps to $3 million acquisitions by reading a book.”
 “Everybody lies—and telling the truth can get you fired. This isn’t corporate America anymore.”

He also shared a powerful story of one student who failed solo for 12 months, then bought a 7-figure company within six months of joining Elliott’s program—transforming not just their career, but their family legacy.

Takeaways:

• Deal-making is a skillset, not a mindset—and most people are dangerously underprepared.
  
  
• You need 1-on-1 coaching to navigate the hundreds of nuanced, high-stakes decisions in a deal.
  
  
• Time is your enemy when you’ve got a family, a job, and one shot to make it work.
  
  
• Buying a business isn’t just about money—it's about freedom across generations.
  
  
• “This isn’t painting your room. This is a life’s work.”
  
  

Whether you're a six-figure earner ready for your next chapter or just curious about the business buying journey, this episode offers a rare, honest look behind the curtain—and a roadmap to avoid joining the 90% who never make it.