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:
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:
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.
