Why This “Crazy” Deal Was Worth It

“It is far better to have understood why you failed than to be ignorant of why you succeeded.” — Dr. Burgelman

In 2020, I made what some people might have called a crazy move:

I bought a property management company that was still being run entirely by the owner, with paper systems for everything….even monthly owner statements.

On the surface, that might sound outdated. But here’s the truth: it was a smart move.

The acquisition added significant doors and revenue to my company and immediately grew both my size and market share. From the outside, it looked like a big win — and it was.

But what I didn’t anticipate was the client reaction once I began integrating that portfolio into my business.

The Uphill Battle I Didn’t See Coming

I knew how the business had been run. I’d done my due diligence.

What I didn’t expect was how deeply clients were tied to those old-school systems.

• Some resisted moving from paper to portals.
  
• Others struggled with losing “their one person” since I ran a hybrid departmental model with a team.
  
• Even upgrades like faster communication by email and text — and monthly owner statements delivered digitally — backfired with a few who felt the “old way” was safer.
  

At first, it felt like I’d stumbled. I thought I was just buying a book of business. But what I was really inheriting was an entire way of doing business.

Why I Don’t Regret It

Here’s the deal: it still ended up being a very good acquisition.

• My revenue grew significantly.
  
• My market share expanded.
  
• And the lessons I learned made me sharper than ever.
  

Because success isn’t just about closing the deal. It’s about understanding the hidden work that comes with change. It’s about anticipating where friction will show up — and knowing whether you’re ready to lead people through it.

The Lens That Changed How I Evaluate Companies

That experience gave me a new lens when I later evaluated property management companies on a national level.

I could instantly recognize the “paper and personality” businesses — the ones that looked shiny on the outside but carried uphill battles tucked inside.

Those are the details that separate a business that simply operates from one that’s truly an asset.

The Takeaway for Business Owners

If you’re growing your company, here’s the lesson:

• You’re not just adding doors.
  
• You’re not just adding revenue.
  
• You’re shaping the very way your business operates.
  

Growth isn’t just contracts. It’s habits, systems, and expectations.

And if you want your business to be worth more tomorrow than it is today, you have to build it with intention — not just acquisition.

Final Thought

Not every win is a clean home run. Sometimes the real victory is in the swing you sharpen for what’s next.

Your turn:
What’s one challenge that felt messy in the moment but taught you a lesson you still carry today?