Brian Chesky: Breaking social norms

Daily Hint
Daily Hint
Published in
5 min readJun 11, 2016

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If there is one thing every parent tells their children it’s not to talk to strangers, so staying with them is surely out of the question?

Someone should probably inform Brian Chesky, clearly his parents didn’t get the memo…or perhaps they had bigger plans?

Hell bigger plan… you can call me Airbnb. Airbnb is a website where people can list, find and possibly rent places to stay, all over the world. Without even going further into detail you can probably already guess the concerns and criticisms this venture was met with prior and post its success. First of all, why on Earth would you pay to stay with a stranger?

Naturally…you wouldn’t. Yet, despite numerous attempts to undermine his idea Chesky and his partner were able to make it work and in the process were able to change both the public perceptions of the idea as well their way of living and that’s essentially what every good entrepreneur wants. They want to provide a service that changes people’s lives for the better, Chesky did anyway. But to do this often comes at a great cost, one that is upfront, non-refundable and is guaranteed, unlike any future success that may or may not strike. It usually means going against the public, introducing something new into their lives, something that will ultimately replace or drive out something that is a huge part of their daily/weekly/monthly routines. That’s a lot of somethings. But that something is usually met with hostility, people fear what they do not understand, they also don’t like change. And so it’s stunning how Chesky has not only challenged his critics head on but has seemingly won a lot of them over.

Warning: The following quote is the worst quote that ever made sense.

‘The worst idea that ever worked’ — Brian Chesky

Brian Chesky is another one of those entrepreneurs who starting out by not wanting to be one, he was an artist. As cliché as it sounds he had parents who wanted better for him, they were social workers and wanted him to help people but to also make some money from it. In a recent interview he humorously quoted his mother saying ‘you want to be the only thing that pays less than a social worker’ — this was her response to his career choice.

Naturally, all great entrepreneurial projects have seemed to blossom from a contagious human condition I-don’t-want-to-starve-to-death Syndrome, Chesky is no exception. In order to help others, he first had to learn to help himself and this involved a lot of moving around and numerous job changes.

Everything about his journey to success essentially challenged the status quo, the only thing he did right in terms of convention was disappointing his parents in terms of career choice…but even then he failed, I mean an estimated Net Worth of $3.3B is not too shabby.

Above all however, his business is what raised the most concerns, be it ethical issues or more general queries about practicality. Unfortunately for Chesky these weren’t just critics being critics, these questions were in fact very valid and the answers to these questions would actually spur on his rise to success. Even so, after a year of launching people still hated his idea and he had no interested investors or customers, he ended up re-launching three times!

Chesky was called many things whilst building his empire. One of which was a disruptor, it was said that Airbnb was undermining old companies and industries by being fast moving/growing and asset light, but that’s not his fault, everything is online these days and there was room for his creation. He was also called inexperienced and was criticized for his lack of knowledge in terms of being an entrepreneur, like I said…he was an artist. But Chesky agreed with these claims and embraces both of these factors as they empowered him to succeed. In not knowing any better he was able to contradict the impossible because he wasn’t thinking rationally about what was possible. He even goes on to say that all experts are in fact experts of History, they are only geniuses about concepts that have already been proven not what has yet to be proved.

He also says that it wasn’t until he realized that people needed to experience what he and his roommate had before they understood the need for it and this is the key to challenging people who are set in their ways. Make them believe they need something, make them WANT to believe they need something. Because they often do, they just don’t realize it.

New York State’s Attorney General claims 72% of Airbnb rentals in New York City are illegal hotels, but Airbnb is such an ‘original’ concept shall we say, that the laws regarding hotels and general housing are not necessarily applicable because the premise of Airbnb is somewhere in-between. And so Chesky moves his product from city to city, country to country in the hope that despite certain cities not embracing it not everyone or every law will have the same views on it. The problem is, open platforms like this will always lead to extraneous variables and with 35 million people using it not every experience is going to be a positive one. Instead, Chesky and his partner use all of these negative experiences as a data point via the online reputation system and so all Airbnb hosts have a vested interested to provide a great service. And this business acumen that has been thrust into everyday people is another part of Chesky’s scheme which he calls ‘Sharing Economy’. Sharing economy is the notion that a person can become a ‘makeshift or even full time entrepreneur’ using any of their own resources that have yet to be monetized. This essentially transforms you and I into YES…ENTREPRENEURS…congratulations. This doesn’t just mean becoming an Airbnb host, it could simply mean loaning that dusty bike in your shed to an unhealthy neighbour for a small fee a week.

Brian Chesky…turning strangers into acquaintances, bored couples into landlords, empty rooms into businesses, and those on a budget into travelers.

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