We F*cked Up Our Resort - And You Will Too

We’re in a good spot at Posh Outdoors. 

Our SkyGlass units at Skyridge Glamping are nearly fully booked, charging sky-high daily rates.

We’ve ordered more units, and we’re shooting for at least one more location in 2026.

But it hasn’t all been smooth-sailing. We’ve made a ton of mistakes along the way.

Here’s how we messed up, and why it’s perfectly okay.

Going Too Big, Too Soon

Ambition is great, but you need to know what’s realistic.

Because Posh does revenue share partnerships rather than ground-up developments, we thought we could open several locations at once.

So, we asked institutional investors for millions of dollars to make it happen.

They laughed us out of the room.

We had no track record of development. This made it hard to raise money for one project, let alone three.

Cue a reset. We decided to crowdfund money to capitalize one project: Skyridge Glamping.

13 months of hustling later, we hit our raise target thanks to 185 investors who believed in us. It was the catalyst for the huge launch and further investment that followed.

But we only got there through messing up first!

The lesson: Start small and prove your model before going big

Underpricing at Launch

By the time we opened the booking calendar in May, we had around 1,500 “Skyridge VIPs”. They’d paid $25 for first access to the calendar.

We’d built that VIP list over a couple of months. They were hyped up to book, which was obvious by the activity in our VIP Facebook Group.

Basically, these weren’t price-sensitive buyers. They were our earliest adopters, desperate to get the Skyridge experience.

Still, we were conservative with our pricing. We were scared that if we charged too much, we’d face a backlash and nobody would come.

We capped our rates at $800 CAD (c. $575 USD) for the height of summer, with fall and winter rates in the $400 CAD ($285 USD) range.

This was a big mistake.

We achieved our objective with the launch, which was to fill the booking calendar. And, at the time, we were happy with the rates we’d achieved.

Now though? Those rates are small fry.

Earlier this week, a guest paid $1,334 CAD ($950 USD) for 1 night in September 2026. That’s more than 4x the September rates we charged at launch.

So yeah, we were delighted with how strongly things started. But we could have made a ton more money!

The lesson: Don’t let fear stop you charging what you’re worth!

Cheaping Out on the Website

Posh Outdoors doesn’t really need a fancy website yet.

We’re not taking bookings directly (they all go through Skyridge or the OTAs), and we had plenty of interest from potential revenue share partners before our website went live.

But still, we wanted a good website.

We thought we could get away with being cheap. We hired a random web designer from a platform called DesignCrowd. It’s a bit like Fiverr, where you can find cheap freelancers.

His design work was okay, but he couldn’t host the website himself. And the design files he gave us were basically unusable (I won’t go into the boring technical details). 

Weeks of hard work went down the drain. We had to start from scratch.

We decided to use a proper agency, based locally in Edmonton. The difference was night and day. They got a functional website up and running in a matter of weeks.

Check it out here if you like.

The mistake cost us a bit of money, but the real headaches were the time and frustration we expended. We should have worked with the experts from the start.

The lesson: Spend real money on your website

Not Trusting Our Partners

A reminder on how the Posh Outdoors revenue share model works.

We partner with a landowner (or in the case of Skyridge Glamping, a leasholder). We install the lodging units on their land, taking a % of the revenue.

In most cases, we’ll handle the marketing too. But for the Skyridge deal specifically, they’re in charge of marketing.

We knew Team Skyridge were a good bunch. But we had concerns over their marketing expertise. None of them had specialty experience in marketing a resort like this.

I’m a big advocate in bringing in content teams to come to a property, batch-capture a ton of videos, and repurpose them into Instagram Reels throughout the year. I still think this is the most effective way of creating content that works.

We recommended this route to Skyridge Glamping early on, but their budgets were tight. They didn’t want to sign it off, and their decision was final. They’d do everything in house.

It was all very amicable. We understood their cost constraints, and we told them we’d support their decision regardless. But we were a little worried.

We didn’t believe they’d go from Instagram rookies to experts in the space of a couple of months.

But that’s exactly what they did.

They captured their own content, edited their own Reels, and posted them for the world to see.

It was a little ropey at first, but content got better, and better, and better.

Now, Skyridge’s Instagram page is performing brilliantly. It’s growing by the day, and the Reels are hitting big numbers.

Crucially, it’s converting to a tidal wave of direct bookings.

We knew the guys involved were smart, competent and hard-working. But we didn’t think they’d figure things out that quickly.

I still believe in using big content teams. But sometimes budgets don’t allow for it. And when the purse strings are tight, you need to have faith in smart people to figure it out.

The Lesson: If you have a talented team, trust them!

Final Thoughts

We weren’t alone in messing up along the way.

Under Canvas’ first location completely failed. Bolt Farm Treehouse thought they could skip the permitting stage and nearly lost their business.

The best operators get things wrong, and you will too. Mistakes are par for the course.

The key is to navigate those mistakes, and learn from them. It’s those harsh lessons that will make you a better operator.

Here’s to f*cking up!

Posh Outdoors is preparing to raise more capital for our expansion. To learn more about upcoming investment opportunities, fill out this form.