06/01/2026
Five years ago, everyone knew someone making a fortune in vacation rentals.
Your neighbor's boyfriend's best friend's dentist was supposedly making $20,000 a month doing absolutely nothing.
You ignored it.
Then your cousin bought a cabin.
Then your CPA bought a cabin.
And suddenly it didn't sound so crazy.
So you bought one too.
At first, it worked.
The bookings came in.
The market kept climbing.
The cabin that felt like a stretch suddenly felt like a genius decision.
Then the market changed.
The same pine walls that once felt rustic and authentic now feel dated and tired.
The furniture that looked cozy five years ago now looks like every other cabin in a sea of listings.
What used to feel like passive income is now a second job–but worse.
Instead of getting paid, you're paying to work it. A lot.
Honestly, it makes me sad.
Because most owners weren't trying to get rich quick.
Most were hardworking people trying to make a smart decision for their family, their retirement, or their future.
And now they're stuck with some unfair self-doubt wondering what to do next.
Sell?
Wait it out?
Renovate?
Lower prices?
Add a pool? A slide? Pickleball?
Spend another $50,000?
Spend nothing?
The problem is that everyone has an opinion.
Contractors.
Management companies.
Facebook groups.
YouTube.
AI.
Friends.
Realtors.
Designers.
But very few people are helping owners answer one simple question:
If this were your money, where would you spend the next dollar?
That's the question I've become obsessed with.
Over the last five years I've worked in vacation rentals, hospitality, design, construction, real estate, branding, guest experience, tourism, and marketing.
I've watched owners spend tens of thousands of dollars on improvements that didn't move the needle.
I've also watched relatively small changes completely transform the way a property competes.
So I've been building something new.
Not a design package.
Not a property audit.
Not a strategy call.
And definitely not a hunch.
A decision-making package.
A way to systematically evaluate a property, identify opportunities, estimate costs, prioritize improvements, and determine where to spend–and where not to.
No revenue promises.
No booking guarantees.
Just a clear roadmap.
Because it's my biggest ick to tell people I'm an expert–or the funniest person they know. I'd rather show them (so they can tell me).
If you own a vacation rental right now, what's the biggest question keeping you up at night?
