An Honest Review of Outsite – Haleiwa

I just got back from a 9-day trip to the North Shore of Hawaii, specifically the town of Haleiewa (pronounced hal-ay-eve-ah).

I stayed the whole time at the co-living, co-working house there, and wanted to write a review of the house, Outsite itself, and my experience.

I would like to start out with the background of my story, and a bit of my experience with the company in general…

Here we go!

I discovered Outsite in January, as I was living in Venice, CA. I went to meetup with a presentation by the founders of Safety Wing, a digital nomad travel insurance company with some world-changing goals. (you can listen to my interview with the founder, Sondre Rasch, here.)

Outsite seemed like a wonderful idea! Traveling to cool, fun, interesting places and living with others who are also working on projects or just working while they travel. This solves a lot of the problems I’ve experienced in the past, where the backpacker crowd is kind of the default of who you meet on the road.

When you’re not a 20-something penny pinching backpacker trying to scrape up enough to travel and barely get by, and you’re not highfalutin resort-type, and enjoy meeting people with business and life goals that align with your own, Outsite is pretty ideal.

I was really wanting to leave LA and work from somewhere else. I noticed they had a house on the beach in Costa Rica, and I had a couple friends traveling throughout that country that I thought would be cool to meet up with.

So I first applied to become a member of Outsite, since you get booking discounts as a member, and it’s only $150.

I filled out the application and days went by, but no response.

Oh well, I thought, I’ll just book a room at the CR house anyway, as it might sell out, and I was only about 8 days out from when I wanted to leave.

So I requested to book a room in the Costa Rica location.

I got a confirmation in less than a day. “Congratulations! You have been accepted, please fill out the form with your credit card to reserve your room for the stay”.

So I filled everything out, got a confirmation that they got my booking, and went ahead and booked a flight (one way) to San Jose, CR.

The next morning, Outsite sent me a message:

“Apologies for the inconvenience, but the house is full for the dates you requested.”


I was accepted and booked it, how could it be full?

I emailed them back, but rather than wait, since the clock was ticking, I went to their Facebook page.

I told them what happened and my situation with a non-refundable plane ticket.

Here’s the exchange on FB messenger:

So they ended up offering me the 2 free nights, and I took them. I searched and found that there was room at the Haleiwa house, and I had some United Airlines miles to use for a flight, so I just went ahead with it- I wanted to give Outsite to full chance here.

Unfortunately, I lost about $480 on the flight to Costa Rica that I had to ditch. The 2 free nights make up for some of this, maybe $160 worth, which is much better than nothing, and I’ve been wanting to go to Hawaii for a while, so I was not upset- only disappointed that Outsite didn’t seem to want to acknowledge their mistake, or that they would correct the process for others in the future, so that it does not happen again.

Off To Hawaii – Haleiwa

I was excited to hang out on the North Shore of Oahu, experience the lovely weather, get some work done, and hike, surf, swim, and meet some interesting people.

I booked 9 nights. Why not? YOLO and I had no reason to hurry back to California.

I spent one night at a hotel in Waikiki. This is not my favorite place. I waded through the mass of Japanese and American families on their vacations and grabbed breakfast at IHOP. $20!

Then I went to Starbucks to do some work. Yep, living the American dream here!

I thought the Outsite house was 35 minutes away, but unfortunately that must be late at night, because I checked Uber and it said 1 hour 10 minutes, while the bus was 2 hours, 10 minutes away! I opted for a $61 Uber to get to the North Shore.

When I got dropped off, there was this odd gate at the front. It was clearly there to block cars from getting through, but it was “locked” with a bike lock that you could easily lift up and open the gate!

The house and the grounds were REALLY cool! It’s on a farm and you’re surrounded by green grass- along with chickens, roosters, lots of chirping bird, frogs, lizards and more!

I was a bit confused when I walked up to the house (there’s no front door), but a couple of people were in a little co-working area downstairs, and one of them showed me around a bit, and I found my room on the 2nd floor.

The Pros

I had a great feeling about the place. From the house, to my room, to the kitchen (there’s actually 2 kitchens in this house), to my “housemates”, to all the sounds of the jungle outside, I quickly felt like I was in the right place.

And a fascinating thing happened when the house was full, that I really appreciated. I think there were 7 people staying in the house at one point. And there are really no rules. Some might think that this would lead to chaos.

But something called spontaneous order took over.

Someone would always do the dishes.
Someone would make the coffee in the morning.
Someone would take the trash out.
Everyone helped with cleaning.
Everyone respected noise levels at night.

There was no schedule or top-down set of rules to keep things orderly, yet, spontaneous order worked very well every day I was there.

Doing without a car at the Haleiwa house was not ideal, as it isn’t extremely close to town, but it worked out just fine for me, as I was able to get rides from housemates, and occasionally bike into town.

The co-working space was just about ideal for me. It’s indoors but the walls are screens, so you get to feel like you’re outside, and you can hear all the birds and roosters (although the birds and their games can be distracting, they do funny things at odd times!)

The food in Haleiwa was also amazing.

Everything I ate from a truck was delicious- the Pitaya bowl, the Japanese place, the Thai place, the taco/Mexican place, all fantastic!

And if you want to stay in, you can order food from Dude, Where’s My Food? (no joke!) I tried it one night and it worked very well.

As far as things to do? Too much to squeeze into just a week or so! Surfing, hiking getting a tan, biking, bird watching, waterfalls…paradise!

Top of the Crouching Lion Hike
Top of the Pillbox hike overlooking Sunset Beach

And I want to comment on the house manager, Trini. She was very on top of things and very responsive to any needs I had. She even offered to lend me her car on my last couple of days! She organizes events once a week at the house, and while I was there, the event was an awesome hike near Sunset Beach.

The Cons

In the co-working room, there was a tear in one of the screens, and mosquitos were getting through.

There were a few other details that were lacking. Sometimes, things were needed at the house that        weren’t there, and there wasn’t anyone to help. For example, we needed a can opener, and apparently that was reported but we never got a new one.

There were TVs but I don’t think they connected to Macs, so difficult to watch anything.

If you are staying downstairs, you will hear the toilets flush upstairs loudly. That only woke me up a few times.

And my main issue goes back to the organization of the company. I was scheduled to leave on Sunday, but wanted to see if I could stay an extra day. I asked on Friday, when there were only 4 of us in the    house, with 2 empty rooms. I figured it would not be a problem to either keep my room, or move to another empty one.

“Sorry, house is full on Sunday” is what I was told.

But Saturday, nobody new showed up. It was hard to imagine that 4 or 5 new people were going to arrive Sunday!

So I left. And, as I heard from one of the housemates later, nobody showed up on Sunday either.

This goes back to organization. I have to question Outsite’s system of keeping track of guests at various houses. Just like when I was told the Costa Rica house was full after I booked. Just like when I applied to be a member and never heard back.

This is clearly a system issue that needs to be worked out.

Maybe they are just passing around an excel spreadsheet, and someone forgot to update it! 🙂

They lost money on me, and I’m sure I’m not the only one having this problem (in fact there was another guy in the house that was having trouble booking multiple nights as well).

The other thing that is missing is a rating and review system for houses.

When you go to book a room on the Outsite webstie, you have no way to get info from previous guests. This is a basic feature that anyone who’s traveling needs to know. This would help both customers of Outsite, to find out more about various locations, and also the company itself- to get better feedback and improve things where needed.

Summary or TL;DR

I’m very bullish on the concept of co-living and co-working.

Haleiwa is a cool little town with lots to offer.

I think Outsite has some issues with organization, customer service, and a way to rate/review houses.

But they get a lot of things right, and the Haleiwa house in Hawaii is overall one of those things.

Incredible Sunset a little West of the house
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Kevin Koskella

Kevin is a podcaster and writer on living free, despite the crazy world we live in. Kevin travels full time and explores the world and how to achieve and maximize freedom in life.

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