https://www.youtube.com/watch?v=M7dTr6-X0DI

Let’s be real: in today’s short-term rental world, it’s easy to get caught up in the next best tool, shiny new dashboard, or "must-have" automation. But at Unlock & Learn 19, we took a different route. Straight into the emotional trenches of growth, change, and making better decisions when it comes to your tech stack and business direction.

If you’re scaling, shifting, or even just trying to breathe easier in your day-to-day, this conversation was for you.

Growth Isn’t Always Glamorous

Hosted by Talia Lockard (Hosteeva) and featuring special guest Brittany Blackman (Discover Freedom), this session pulled back the curtain on what real growth looks like - not the polished Instagram version, but the kind where you're juggling 10 logins, constantly pivoting, and wondering if you’re the only one overwhelmed.

Spoiler: You’re not.

Brittany’s journey from ops manager to founder, and then selling her vacation rental company, laid the foundation for a rich conversation around how - and when - to actually optimize instead of just operate.

Shiny Object Syndrome is Real (and Costly)

We’ve all been there. A new tool drops. You hear rave reviews. You sign up. Six months later, it’s collecting digital dust and no one on your team knows how to use it.

Here’s the kicker: 74% of businesses experience buyer’s remorse after purchasing software. Why? Because the purchase was emotional, rushed, or made without the right voices at the table.

Pro tip from Brittany: Always ask for a trial. Always ask if your software already does what you’re trying to solve for. You might be surprised at how much value is hiding in tools you already pay for.

The Three Tech Mindsets

Talia broke it down brilliantly:

  1. Things are working, we’re good → That’s great! But still check in regularly.
  2. We’ve been cobbling together tech as we grow → Time to stop, document, and assess.
  3. Nothing is working and we’re overwhelmed → You’re not alone. But it’s time to get strategic.

No matter where you fall, the answer isn’t always “buy something new.” Sometimes the answer is better delegation, clearer processes, or asking your current vendor how to get more value.

You Don’t Have a Tech Problem. You Have a Strategy Problem.

This one hit hard. We all love tools. But a tech stack without a strategy is just noise.

“Deciding on tech is a delegation decision. Are you delegating to a person, or delegating to technology?”
— Brittany Blackman

Start with what you’re trying to solve. Map your guest journey. Document your internal processes. Then ask: what actually needs a human? What could be automated?

And yes—use AI tools to help you document and identify gaps. Even a free ChatGPT account can turn a team conversation into a starter SOP.

Talk to Your Team. Talk to Your Vendors.

Just because no one’s complaining doesn’t mean everything’s working. Sometimes, your team has found duct-tape workarounds they haven’t told you about. And sometimes, your vendor rolled out a feature six months ago you never knew existed.

Ask. Reconnect. Use the resources you’re already paying for.

Communication Is the Heart of Hospitality

This one might sound obvious, but it bears repeating: your vacation rental business doesn’t work without clear communication. That includes communication with:

If your tech isn’t supporting better communication, it’s probably time for a rethink.

Give Yourself Permission to Slow Down

Growth can feel like a sprint. But optimization? That’s a marathon. Make the time. No one’s going to give it to you.

“You have to decide—do you want to pay for clarity now with time or later with regret?”
— Talia Lockard

Whether you’re running solo or leading a team of 30 (even 100), the principle holds: pause. Write it down. Think long-term. And don’t be afraid to say “no” if something doesn’t serve your business. And remember, it is never too late to start.

Final Thoughts: Your Business, Your Timeline
 There’s no one-size-fits-all tech stack. No magic system. No perfect path. But there is your path and this conversation was a reminder to honor it.

So whether you’re still operating or just beginning to optimize, take a deep breath. Growth isn’t always linear, and decisions don’t have to be perfect. They just have to be intentional.

Need help finding tech that actually fits your business?
 Reach out to Talia Lockard at Hosteeva or connect with Brittany Blackman at Discover Freedom.

👉 And don’t forget to subscribe to our newsletter here for future sessions and industry updates.