E286: Deals Don’t Fail on Paper—They Fail in People - Watch here 

About the Guest:

David Miller is a seasoned dealmaker with an unusually diverse portfolio. From growing a finance firm in the depths of the 2008 crisis to diving headfirst into cannabis cultivation, clean energy, and even competitive fashion, Miller blends strategy with heart. He’s a global speaker, EO member, MIT graduate, and firm believer that small business is powered by soul—not spreadsheets. His coaching practice is rooted in aligning people, strategy, and scalable systems to turn growth into exit velocity.

Summary:

David Miller’s journey isn’t your typical “finance guy turned entrepreneur” story—it’s a gritty, globe-spanning career that merges heart and horsepower. From buying his first company via seller financing to managing roll-ups in industries as varied as cannabis, clean energy, fashion, and finance, Miller shares hard-earned insights from the trenches. In this in-depth episode, Ron Skelton and David dig into what actually makes M&A work—hint: it’s not just spreadsheets and strategy. It’s trust. Culture. Emotional intelligence.

This conversation serves as a blueprint for anyone serious about scaling through acquisition. Whether you're on your first deal or your fifteenth, Miller’s frameworks around emotional readiness, culture integration, and trust-building are worth replaying. Often.

Key Takeaways:

1. M&A Begins with Trust: Deals live and die on rapport—not just with the seller, but with the acquired team. Trust is the true currency in successful transactions.

2. Seller-Financing Wins: Miller's first acquisition was a small, seller-financed deal—highlighting that not every transaction needs SBA debt or a PE fund.

3. Don’t Skip Culture Fit: A players don’t stick around if you bulldoze culture. Integration takes time, patience, and listening.

4. Vision Without Execution is Fantasy: Miller emphasizes method + magic = alchemy. Intuition and process must coexist.

5. Diversification is Learnable: He’s run companies in industries as varied as cannabis, fintech, and fashion. Why? Because business fundamentals—people, process, and trust—are universal.

6. Buyers Often Move Too Fast: Rushing in to change systems, fire people, or “fix” things too soon leads to resistance and turnover. Observe before acting.

7. You Might Outgrow Your Business: Founders need to recognize when their business has surpassed their skillset—and decide whether to level up or step aside.

8. Most M&A Fails Are People Failures: 70% of acquisitions fail, and it’s rarely because of numbers. It’s trust breakdowns, poor communication, and mismanaged change.

Article:

Trust Is the True Due Diligence: Why David Miller’s M&A Framework Is Built on People, Not Just Profit

There’s a quote tucked inside this episode that should be framed on every buyer’s wall:
“Method and magic equals alchemy.”

David Miller doesn’t buy businesses the way most finance bros do. He doesn't open with a spreadsheet. He opens with a conversation. And it’s not about EBITDA—it’s about origin stories, employee vibes, and whether the seller still dreams about the business they built. Because for Miller, deals aren’t numbers. They’re people.

His first deal? Seller-financed. He put 10–20% down, bought from a retiring woman with a horse farm dream, and used trust—not leverage—to close the deal. Fast forward years later, and he’s engineered roll-ups across cannabis, clean energy, and even fashion (yes, fashion—ask him about dresses made of trash).

Miller’s view is refreshingly counterintuitive in today’s “snag a deal on BizBuySell” echo chamber. For him, most M&A failures have nothing to do with financial modeling and everything to do with emotional blind spots. “If the seller doesn’t trust you, the deal’s already dead,” he says. “And if the team doesn’t trust you post-close, the integration’s doomed.”

His six-part framework for what you’re really buying in an acquisition is gold:

• Time

• Customers

• A-Players

• Team Intelligence

• Cross-sell Opportunity

• Operational Efficiency

But they all hinge on one invisible asset: trust.

And it doesn’t stop there. Miller unpacks how many founders don’t exit because their business is failing—but because it’s outgrown them. Knowing when to level up or get out of your own way is a skill few entrepreneurs master. That emotional maturity, he argues, is what separates serial sellers from first-time flounderers.

So, if you’re looking for the magic formula to M&A, Miller makes it clear:
It’s not magic. It’s method, people, and a whole lot of listening.

Buy the company.
Honor the culture.
Earn the trust.
And then scale.

---- MORE COOL STUFF ---

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