Growing up, Brian Chesky never envisioned himself as an entrepreneur. Instead, the Airbnb co-founder came up with the idea for his company almost by accident. Struggling to make rent in their San Francisco apartment, he and co-founder Joe Gebbia blew up several air mattresses and rented out their apartment to attendees of a design conference in town.

That idea blossomed into a company that now lists 1.7 million homes for travellers looking for a place to stay in 34,000 cities worldwide. Chesky did not go to business school and is a first-time CEO. He has successfully managed to raise Airbnb from a bootstrapping company to a multi billion dollar platform.


Here are 10 success lessons from Brian Chesky – “Airbnb Founder and Billionaire” for entrepreneurs,

1. Don’t brainstorm startup ideas, solve a problem

Citing the story of how Airbnb came about from renting out the founders’ apartment for a weekend, Chesky says he’s learned the best ideas for companies often stem from attempting to solve personal problems. “If we tried to think of a good idea, we wouldn’t have been able to think of a good idea at all,” he says. “You just have to have a solution for a problem in your own life.”

2. Surround yourself with role models

Chesky says he considers about 20 to 30 entrepreneurs, including Y Combinator president Sam Altman, to be his mentors. “Every time I didn’t know how to do something, I figured there’s someone who does,” Chesky said. Aspiring entrepreneurs should be aggressive about seeking help and advisors, as they are often eager to impart their wisdom, he adds. “Some of the best entrepreneurs are the most shameless people in the world,” he says.

3. If you believe in your idea, you will find a way to make it work

Initially, investors dismissed his idea as ‘crazy’ and Chesky has a tough time keeping the company afloat. He and his co-founders sold special breakfast cereal in boxes that carried funky names (Obama O’s and Cap’n McCain’s) to attendees of the Democratic National Convention in November 2008 so they could keep Airbnb going.

4. Building a platform is tough; both sellers and buyers need to be on board

No travellers would come to the Airbnb website without accommodation listings; however, no one would list their place without travellers on the site. Brian Chesky said that he had to build the business one home at a time, then block by block, street by street and city by city.

5. Being your own customer is the best way to learn

In 2011, when the company was in the process of strengthen its service, Chesky lived in 30 different locations he found on AirBnB. The more he used his service, the more he figured out ways to polish it.

6. Focus on a small but loyal customer base

Chesky says some of the best advice he has received is that it’s preferable to have 100 people that love your company, rather than a million people that “sort of” like it. “If 100 people like you, then they tell 10 people,” he says. From a management perspective, it’s also easier to focus on the needs of a smaller core group of customers.

7. Get informed about your industry’s laws and regulations

Airbnb has run into its fair share of issues with local and national hospitality laws. Part of that comes from the inevitable clash of starting a tech company that must work around laws that don’t take into account the burgeoning concept of the sharing economy. The best solution to those hurdles is knowledge and an open mind, Chesky says. “We can definitely have more than just a coexistence [with local laws],” he says.

8. The first employee is like bringing in new DNA

When hiring their first employee (who was an engineer), Chesky ran through thousands of applicants and interviewed hundreds of people. After six months, he found his guy. Chesky tells that he viewed bringing this first employee as analogous to bringing in new DNA into the company. He didn’t view it as the person to build a few features. He viewed it much more long term, because there were going to be a thousand people just like him. You want diversity, of course, but you won’t want diversity of values.

9. There’s no learning curve for people who are in war or in startups

He has had meetings with Facebook’s Mark Zuckerberg, Amazon’s Jeff Bezos, and eBay CEO John Donahoe. He went to Bob Iger and Marc Benioff to ask how they push their executive teams to do more. From Facebook’s Sheryl Sandberg he picked up tips about efficiency in scaling internationally. Learning is a constant process for Chesky.

10. A company’s culture is what defines it

Chesky believes that working at Airbnb is not a job, but a calling. He personally interviewed the first 300 employees of the company. Even now, he makes sure that he meets every employee. He wants to be the world’s largest start up.

About Author

Biplab Ghosh

Biplab lives his life around technology and is particularly keen to explore the intersection of technology and human behaviour. Always looking for new ideas, and ways that can make things simpler. He is a geek with the flair for travel and has great passion for music and theatres.

Leave A Reply