The Brian Chesky playbook for success

Co-founder and CEO of Airbnb Brian Chesky speaks during an interview in Langa township, Cape Town, South Africa March 17, 2017. REUTERS/Mike Hutchings

After Airbnb’s smashing IPO on December 10, Brian Chesky will never have to worry about having a roof over his head. The company’s co-founder and CEO became richer by $6.5 billion after the company went public.

Even before the IPO, Airbnb was a success story, financially and in terms of impacting lives. Luckily for aspiring entrepreneurs, Chesky has often shared advice on how to build a thriving brand.

One of his insightful tips was to not be in a rush to find investors, and to ultimately meet them through a mentor who knew your abilities and who would first make a case for you.

“Wait longer before you meet investors, because you’re going to spend an enormous amount of time getting rejected,” Chesky once said on the podcast ‘Masters of Scale’. “When you meet investors, you need to make sure that you have people vouching for you, that are telling the investors how amazing you are.”

The NASDAQ market site displays an AirBnb sign featuring CEO Brian Chesky on their billboard on the day of their IPO in Times Square in the Manhattan borough of New York City, New York, U.S., December 10, 2020. REUTERS/Carlo Allegri

In the event that you did not have such people, Chesky advised seeking out mentors.

“Investors aren’t going to meet you, unless through an introduction,” he said. “And they may not have the courage to invest in you. Your mentors should be people your investors will admire and respect when they brag about you and say how smart you are.”

Chesky also famously believes in not raising too much money in a company’s early stages. He believes it helps a company stay disciplined and hungry.

Airbnb Co-Founder and CEO Brian Chesky pose for selfie with students at Fudan University in Shanghai, China March 21, 2017. Picture taken March 21, 2017. REUTERS/Stringer

“I would make sure that I did not raise too much money,” Chesky said on the podcast. “If you develop a scrappy culture, it requires you to build more novel solutions, use fewer out-of-the-box software things and you end up just building a scrappy, more frugal, more startup-like environment.”

Chesky said one more advantage of raising less money from investors was that founders retained more control of the company. And though that could create constraints, Chesky feels that “Constraints create creativity.”

“In the upside that you’re super successful, you will be happy that you raised a little less money, gave up less control, and you have a higher-quality investor,” Chesky said.