Before I ever helped scale companies in healthcare, logistics, or digital marketing, I was deep in the short-term rental world.
And for good reason.
I’m Dr. Connor Robertson, and when I talk about short-term rentals (STRs), I’m not talking about Airbnb side hustles. I’m talking about fully operational businesses that require forecasting, management systems, real estate awareness, and strategic marketing to work.
STRs were my first serious business focus, and they taught me everything I now apply across other industries.
Let me break down exactly what I learned and how that experience shaped the way I now help founders build scalable, process-driven companies.
Lesson 1: Local Regulations Can Make or Break You
One of the first things I learned in short-term rentals is that revenue means nothing if you’re out of compliance.
Cities, counties, and even HOAs have rules that can gut your entire business overnight. And no amount of guest satisfaction, clever furnishings, or five-star reviews will save you if the zoning board decides you’re in violation.
What that taught me:
Due diligence isn’t optional.
Every business has regulatory risk, whether it’s real estate, healthcare, transportation, or digital marketing compliance. Knowing the local and federal landscape is step one in building anything that lasts.
Lesson 2: Operations > Aesthetics
You can have the nicest-looking Airbnb on the block and still lose money.
The difference between profitability and burnout isn’t decor—it’s operations:
- Automated messaging
- Cleaner scheduling
- Maintenance workflows
- Check-in check-out processes
- Calendar and pricing optimization
When I help other businesses scale, I apply the same principle.
The front end gets attention. The back end makes money.
You don’t scale a company on branding.
You scale it on repeatable, efficient systems.
Lesson 3: Marketing Must Be Predictable
Early on, I realized that STRs lived and died on visibility.
Whether you’re getting bookings on Airbnb, VRBO, Booking.com, or direct channels, the game is simple:
You must be found before you can be booked.
This taught me two critical marketing truths:
- Algorithms matter. You need to understand the platform and how it promotes listings.
- You can’t rely on luck. Reviews, pricing, photos, and messaging must be managed with intent.
Today, when I help founders in other industries, I use that same mindset to build intentional, consistent, and algorithm-friendly marketing systems, whether it’s for a local clinic, a consulting agency, or a concrete delivery firm.
Lesson 4: Real Estate Is a Business Platform
STRs taught me that real estate is not just a financial asset, it’s an operational asset.
When used strategically, real estate gives you:
- Control over your environment
- A stable base for operations
- Brand permanence
- Flexibility in customer experience
I carry this perspective into everything I do now. From helping founders lease vs. buy for business use, to analyzing commercial utility for business operations, real estate is always a consideration, but never the whole game.
Lesson 5: Systems Buy Back Your Life
The final and most important lesson?
Without systems, you own a job. With systems, you own a company.
Short-term rentals forced me to think this way.
Because when you have guests checking in seven days a week, you don’t have time to reinvent the wheel.
Now, whether I’m advising a founder or acquiring a company, my first question is:
“Can this business run without the owner?”
If the answer is no, the next step is obvious:
Build the systems.
Final Thoughts from Dr. Connor Robertson
Short-term rentals were my first serious business.
They taught me how to manage operations, interpret data, market with intention, and systematize at scale.
More importantly, they taught me the real difference between hustle and infrastructure.
That lesson applies to every business I touch today.
I’m Dr. Connor Robertson, and if you’re building or rebuilding a business, the short-term rental mindset may serve you more than you think.
Not because it’s trendy.
Because it’s operational.
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Written by Dr. Connor Robertson