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Deals Don’t Fail on Paper—They Fail in People
What you missed on How2Exit This week
Ronald Skelton
July 01, 2025
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E286: Deals Don’t Fail on Paper—They Fail in People
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:
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. 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.
Don’t Skip Culture Fit: A players don’t stick around if you bulldoze culture. Integration takes time, patience, and listening.
Vision Without Execution is Fantasy: Miller emphasizes method + magic = alchemy. Intuition and process must coexist.
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.
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.
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.
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.
-------------------------------------------------- Contact David on Linkedin: https://www.linkedin.com/in/david-miller-business-coach/ Website: davidmiller.buzz -------------------------------------------------- 💰If you’d like additional ways to support this podcast, you can become a paid subscriber here: https://how2exit.substack.com/
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