The One Reason Airbnb Succeeded

When evaluating why a company succeeded, we might first consider what the idea was. What made it a good idea? Why was the time right for it? Why didn't anyone else think of it? The truth is there were a handful of start-ups with the same idea as Airbnb that were started around the same time, and this is often the case. Ideas are easy to have, and people have lots of them.

Maybe then we might say well what did they do different in their execution? Michael Sibel a prominent leader at Ycombinator would tell you one of the things they did right was allowing hosts to add their bnb for free whereas a competitor charged a small fee for hosts to post on their site. These kinds of things are important, but I'd argue still isn't enough. I believe even if Airbnb hadn't done many of the things they did well, they still would have succeeded. In fact, I think there is really only one key factor that matters when starting a company. So why did Airbnb succeed?

Brian Chesky wanted it to happen – no you don't get it, like he was going to die before Airbnb failed. In fact, you might not know it, but the two Airbnb founders literally almost did starve to death during the first few years of trying to get traction. Could you imagine yourself being so committed to an idea that you spend years trying to get significant traction? I'd bet they would have gone years longer too. This is the difference. It was going to be successful because Brian Chesky said so.

As an ambitious and curious person, this is fascinating, and I immediately wonder two things: 1. How do I become like that? 2. How did he go about choosing this idea? The answers are not exciting for entrepreneurs because you can't muscle your way to becoming like this; however, that is not to say you can muscle your way to success. You just can't muscle your way to this particular kind of success where you stick out a crazy idea because it has to exist. You can't resourceful your way to becoming psycho crazy obsessive, and you can't resourceful your way to picking an idea that will likely work and you will be crazy about – it seems like the idea picks you. So even if you did have the idea for Airbnb, it probably wouldn't have made you hyper committed to it.

It feels to me that being an obsessive person is not a choice. It feels to me that whatever idea does make you obsessive about itself is also not a choice. So what do we do? What do us people who want to be successful do? Live. Just live. Don't get me wrong, try hard! Try your hardest, but you can't find the answers on Google. You'll have to trust your gut. Try hard; trust your gut.


I think you can feel why a person is doing what they are doing. I don't know Brian, but I get the feeling he is very much an artist. He has a degree in design and has all the key attributes of someone making totally irrational decisions. All this to say I think his creative intentions are pure – he just wants to make great things... art with some density and substance. There are many other successful and unsuccessful people that I do and don't know that feel very much NOT like an artist. On paper, yes, they are tech start-up people too, but they feel off... They feel yucky and desperate – I'm very aware Brian was desperate too, but that is a desperation that feels heroic whereas this other desperation feels sad. These other people feel like their intentions aren't pure – they want something that isn't worth sacrificing for.

I wish I had examples or anecdotes to explain this better, but these other kinds of people are who I was shocked and appalled by in San Francisco. Only a very small percentage of tech people I met felt pure in their pursuits. Maybe I'm wrong. It probably doesn't matter if the only goal is to make money and therefore something useful. But if you really want to make something that fills your soul and not just something successful, it probably does matter. I'd imagine it is very hard to find that obsessive idea if your mind is distracted by all the other ideas that could very well become successful.

This might best be explained as the fundamental difference between Apple and Microsoft or, in other words, the difference between Steve Jobs and Bill Gates. I won't go into the details here because this Mac vs PC issue is well documented, but it is the reason Steve Jobs is cool and Bill Gates isn't, despite both being very successful, smart, and obsessive; although, they were clearly obsessive over different things.

2025-05-23