What I’d Do Differently If I Were Starting My STR Business Today

When I started my STR business, I had a clear vision: a well-run property, steady income, and flexibility.

What I didn’t anticipate was how quickly good intentions can turn into overextension — even with automation tools — especially when you’re trying to do everything “the right way” by yourself.

Looking back, there are three lessons I learned the hard way. They reshaped how I run my STR business — and how I think about growth, sustainability, and leadership.

Lesson 1: Waiting until you’re overwhelmed is the most expensive option

Like many hosts, I delayed investing in help.

I told myself I’d bring on support once things stabilized or once revenue justified it. The problem? By the time you reach that point, you’re already operating in survival mode.

I waited too long to:

Hire a VA
Start consistent marketing outside of Airbnb

These weren’t growth moves — they were infrastructure decisions. And delaying them came with a cost: mental, emotional, and eventually financial.

When I finally invested in the right solutions, the impact was immediate. Within a few months, we generated nice direct bookings we wouldn’t have received otherwise. But the biggest change wasn’t revenue.

It was time.

Time to think.

Time to breathe.

Time to run the business strategically instead of reactively.

And with that shift came something I didn’t expect but desperately needed: more mental space. Less stress. More presence in my relationships — and more energy for the life I was building.

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Pro Tip: If support feels “too early,” that’s often a sign you’re right on time. Start with right-sized help, not perfection. Even part-time VA support can dramatically reduce operational drag.

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Lesson 2: Relying solely on Airbnb is not a long-term strategy

Airbnb still drives the majority of bookings for most hosts. That’s the reality.

But the landscape has changed. Rule updates, rising competition, shifting algorithms, and higher guest expectations have made the game tougher. Relying solely on OTAs creates vulnerability.

Even a modest direct-booking strategy:

Reduced pressure during slower seasons
Built stronger guest relationships
Reinforced that our STR was a business — not just a listing

Consistency mattered far more than complexity. I didn’t need flashy marketing campaigns. I needed sustainable efforts aimed at the right audience.

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Pro Tip: You don’t need to go “all in” on marketing. Start with one channel you can maintain — a simple website, email capture, or social presence that builds trust and social proof — and build from there. Momentum beats intensity.

Lesson 3: Doing everything usually means being less effective

This one was the hardest.

After a bad experience with a revenue management service — one that made costly mistakes resulting in thousands of dollars in lost revenue — I decided I couldn’t trust anyone else with pricing.

So I took it on myself for all our STR listings.That meant late nights buried in data analytics, pricing tweaks, and performance tracking. I learned a lot — but honestly, I’d much rather have spent those hours binge-watching YouTube. More importantly, it wasn’t the highest and best use of my time.

I was deep in my dread zone, not my genius zone. Eventually, it became clear: if I wanted to grow strategically and sustainably, something had to give — certain parts of operations needed to be transitioned to others, whether that meant a vetted revenue manager or a well-trained VA.

Letting go wasn’t about losing control; it was about stepping fully into the role of owner, not just operator.

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Pro Tip: If a task drains your energy and limits strategic thinking, it’s a delegation candidate — even if you’re good at it. Effectiveness beats capability.

Support Is a Leadership Decision

STR hosts are resourceful. We’re resilient. But we’re not superhuman.

If you’re doing everything yourself and feeling stretched thin, it’s not a personal failure — it’s a signal that your business needs structure.

The biggest shift for me wasn’t adding more hours (because there aren’t any left) or learning more skills. It was deciding where my time mattered most — and building support around that.

What’s one task in your dread zone you could start delegating to create breathing room to scale?

Feeling stuck on what to prioritize?

Feeling stuck on what to prioritize?
If you’re reading this and thinking, “I know something needs to change — I just don’t know where to start,” you’re not alone.

This is the exact stage where early guidance can save you months — sometimes years — of frustration.

Whether you need help launching or optimizing an STR, or building a scalable system with VA training and consistent marketing, Savvy Breezy offers right-sized support designed for early-stage STR businesses.

👉 Book a discovery call to walk through your current setup, pinpoint what’s holding you back, and identify the next smartest move for your STR.

Book A Free Discovery Call With Savvy Breezy