Jun 3
"For twenty years we tried to eliminate maverick spend. The AI era is about to show us it was never the problem — it was the signal."
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"For twenty years we tried to eliminate maverick spend. The AI era is about to show us it was never the problem — it was the signal."
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How I Evaluate Technology Debt in Small Businesses
When I buy a business, one of the most invisible but costly risks I look for is technology debt. Over time, I’ve learned that technology debt can quietly erode efficiency, create security risks, and block growth. It’s not always obvious on financial statements, but once you take over operations, it shows up in downtime, employee frustration, and customer complaints. Why Technology Debt…
The First Questions I Ask When Meeting a Seller
When I sit down with a seller for the first time, I know that the conversation will shape the entire deal. Financial statements and documents come later, but that first meeting gives me insights no spreadsheet can provide. It reveals motivation, culture, and the human side of the business. Over the years, I’ve developed a set of questions I always ask in that first meeting. These aren’t about…
The Importance of Employee Retention After a Business Sale
When I first started buying companies, I thought the hardest part would be negotiating the price or securing the financing. Over time, I realized that the real challenge comes after the deal closes. And at the heart of that challenge is one thing: retaining employees. A business isn’t just assets, contracts, or financials it’s people. The employees carry the knowledge, relationships, and culture…