When I look at Denver’s business landscape, I see a city built on the hard work of small business owners. The restaurants that people line up for, the construction companies that keep neighborhoods expanding, the local service providers who know their customers by name—all of these represent decades of sweat equity. The challenge I see every day is that many of these businesses don’t have a succession plan. The owners are aging, and when they step away, there’s a real risk that the business simply shuts its doors.

Dr Connor Robertson

That’s a problem not just for the owners but for Denver’s neighborhoods. When a long-standing company closes, employees lose their jobs, customers lose reliable providers, and the city loses part of its fabric. I’ve built much of my career around solving that exact problem. For me, the answer lies in a model that doesn’t get enough attention: debt-based acquisitions.

Debt-based acquisitions are different from the flashy equity deals you hear about on the coasts. Instead of piecing together a group of outside investors or selling off big chunks of equity, the buyer uses a combination of conservative bank financing and seller financing to complete the deal. The business itself generates the cash flow to cover debt repayment. It’s cleaner, it’s more direct, and in my experience, it works beautifully in markets like Denver.

I always start with the numbers. Before I get excited about any deal, I strip down the financials to their most conservative form. I remove one-time revenue bumps, take out discretionary owner expenses, and look only at the recurring, predictable cash flow. Then I stress-test it. Can this business support the debt even in a slow season? Is the debt service coverage ratio above 1.25x? If not, I know the deal isn’t structured correctly. Hope doesn’t pay the bank, and I’d rather walk away than chase something that will collapse under its own weight.

In Denver, I’ve seen seller financing play a crucial role. Many owners want to retire but still want to see their business succeed. A seller note lets them collect payments over time, while also giving the buyer space to stabilize operations. When structured properly—subordinated to the bank and with realistic repayment terms—this arrangement keeps everyone’s interests aligned. The seller has an incentive to see the business thrive, and the buyer gets breathing room.

But let me be clear: the real work starts the day after the closing. I’ve learned through experience that the first 100 days decide the entire trajectory of a deal. When I step into a new acquisition, I don’t hide in an office. I meet every employee personally, I walk through the workflows, I sit in on customer calls, and I look at the cash management systems. I want to see exactly how money flows in and out of the business.

I implement what I call a weekly operating cadence. Every week without fail, I review the sales pipeline, receivables, vendor terms, and operational bottlenecks. This rhythm brings clarity and accountability. Within the first 30 days, I look for two quick wins—maybe it’s renegotiating supplier terms for cash discounts, or tightening up the quoting process so customers get answers faster. These improvements don’t just boost cash flow; they show the team that the new ownership is serious and capable.

Culture is where many new owners fail. Denver has a deeply local, relationship-driven culture. Employees can be skeptical when ownership changes, especially if they fear cost-cutting or benefit changes. That’s why I make it a point to keep benefits consistent in the early stages and to sit down with team members to talk about their career paths. People want to know that they’re valued and that there’s room to grow. If the team believes in the vision, the financial side becomes much easier to manage.

So why does this matter so much for Denver? Because the health of small businesses is directly tied to the health of the community. When a family-owned business transitions smoothly to new ownership, the employees keep their jobs, customers keep their services, and the neighborhood keeps its economic anchor. The city maintains its tax base, and the ripple effects extend far beyond the balance sheet.

I see debt-based acquisitions as a form of financial stewardship. It’s not about flipping businesses or chasing speculative returns. It’s about preserving what works, improving operations, and setting up a business to thrive for another generation. In a place like Denver, where local businesses are the heartbeat of the economy, this approach creates stability.

Over time, these acquisitions build something bigger: resilience. A resilient city doesn’t depend on national chains or outside capital swooping in. It depends on local leaders stepping up, buying local businesses responsibly, and carrying them forward. That’s the type of financial influence that makes a lasting difference.

If you’re an owner in Denver thinking about retirement, or someone considering acquiring a small business here, I encourage you to study this model closely. Don’t get caught up in speculative structures or promises of outside equity. Focus on what the business can actually support, build conservative safeguards into your deal, and commit to the culture of the team you’re inheriting. That’s how you create real long-term value.

I’ve put together detailed frameworks, checklists, and case studies from my own acquisitions that walk through this process step by step. If you want to learn more about how I structure these deals and why they work so well in Denver, you can find those resources at www.drconnorrobertson.com.