Why I Love Buying Properties With Friends

When I talk about buying properties with friends (we’ve bought an island, a flat in Budapest, an apartment in Tokyo, and an apartment in Hawaii), some people get it immediately. Others don’t get the point, quickly do the math and realize that they’d save money and hassle if they just stuck with Airbnbs. It’s hard to rebut that argument, because most of the benefits are hard to explain unless you’ve experienced them. But as I sit here in Honolulu Airport on my way back from a trip to Hilo, I think I can use this trip as an example to illustrate why it’s worth buying properties with your friends.

First, the decision to do a trip at all was much easier. The three of us that went on the trip all own the property together, so it makes Hilo an obvious place to visit. There are also no logisticts to worry about. We can come or go on any days we want, don’t have to check in or meet someone to get keys, and have our minivan parked out front. Imagine if we wanted to go to Maui. We’d need to rent cars, choose an airbnb, and all go on the same days because no one wants to pay for an Airbnb by themselves if others leave early.

And, of course, the marginal cost was totally insignificant. We had to buy plane tickets (or use miles, more realistically), but we had no lodging or car rental costs. Because of this we can go on trips whenever we want, so we tend to travel together much more often. Before owning a place in Hawaii I visited once every few years. Now I go once every few months, almost always with at least one of the other owners.

Once we arrived in the apartment, everything was just as we left it. I changed into my linen Hawaiian shirt and board shorts, both of which sit in a plastic bin under one of the beds. I took out my set of sheets and made up one of the beds. Unlike an unfamiliar apartment or AirBnb, I feel like I’m home.

The next day we went and had poke at Poke Market, which I think may literally be the best poke in the world. We eat lunch there every single day, so we know the owner and all of the employees. We chat with them for a while and catch up on the latest Hilo news. Even though we don’t live there full time, we’re regulars and have made friends all around the city. When we leave people don’t ask when we’re coming back, they ask how long we’re leaving for. Besides getting to see friendly faces immediately, we don’t have to waste any time figuring out where to eat. We still try new restaurants all the time, but we have our default routine.

After Poke Market we go get shave ice at Kula Shave Ice, which is one of the best shave ice places in the world. They have lots of employees so we don’t know them all, but we’ve become friends with the owner. I ask her about some sesame oreo ice cream she had on her instagram a few months ago and she says she’ll try to make some before we leave. From Kula it’s a two minute walk to Nautilus Dive Shop, a really cool mom and pop dive shop. I actually learned to scuba dive there 20 years ago. We ask about the conditions and get some advice on when to dive. They found a GoPro underwater, so they give it to me to charge for them to see if they can look through the pictures to figure out whose it is.

We end up not diving that day, but instead dive a few days later. We have three sets of scuba gear in a closet, so we don’t have to pay to rent anything except for an air tank. We just load our plastic bins into the van and head to the beach. Sometimes it’s amazing and we see really cool stuff, other times it’s just a relaxing hour underwater with the usual fish and sea life. But for $8 and no hassle, we may as well go whenever we want. I brought a diving compass this trip so we explore a few hundred feet beyond our usual underwater landmarks. If we were renting and going on vacation, we would have to rent all of the gear and go with a diving company. If we didn’t see amazing fish we might feel like it was a waste of money.

In the afternoons we might go for a little hike or something, but we’re also happy to just stay at the apartment. It’s equipped pretty well for us to work, and because we know we’ll be back dozens or maybe hundreds of times in our lives, there’s no pressure to be doing tourist stuff all the time. Some days we just sit around and drink tea and chat, taking breaks to play VR together.

We also spent a good day or so improving the apartment. Our living room use to be pretty spartan and had one awful light mounted to a noisy old ceiling fan. We replaced the ceiling fan, got end tables and lamps, some decorative pillows, and a couple poufs for extra seating. Now the living room feels great and I noticed that we congregated and spent more time there than usual trips. It was fun to permanently improve our apartment and was very inexpensive for all of us because we shared the cost six ways. I also got really bad allergies at the apartment so I got a HEPA filter and started running it. I was skeptical, but it solved my allergies completely! I don’t think I could count on an Airbnb to have an air filter.

I left tonight, but one friend is leaving tomorrow and another friend is staying for almost an extra week. It’s impossible (or at least expensive) to have that kind of flexibility if it’s not your own place.

Even leaving is easier. I just put my stuff back in my little bin and lock the door behind me. If this was a once-in-a-lifetime Hawaii trip, maybe I’d be sad that I was leaving or be disappointed that I didn’t pack every single day full. Instead I just feel grateful for my trip and look forward to doing even more next time.

I hope this post gives a glimpse into why it’s so great to own properties with your friends. You can’t just do the math and decide that AirBnB is a little bit cheaper and easier. Those things are true, but it’s such a different and better way to spend time in different places that there’s really no comparison.


By the way, people always ask me to write a book on how to buy properties with friends. I doubt I’ll write a book, but I think I will do a YouTube Live and talk about it and answer questions. If that’s something you’re interested in, let me know.

I did a podcast interview that was just released a couple days ago. Check it out!






One response to “Why I Love Buying Properties With Friends”

  1. Gillian Avatar

    Phil Levin is writing about this over at Supernuclear, the blog we co-write about coliving. A few people have mentioned this post in reply to that one so wanted to drop a reference over here too! https://supernuclear.substack.com/p/how-to-co-buy-a-vacation-home-with

Leave a Reply

Your email address will not be published. Required fields are marked *