Win with stories: Barack Obama and Airbnb

Back in 2016, at an event in Havana in Cuba, the US President appreciated an entrepreneur. Barack Obama cheekily asked him,”How much is your company worth?”

“About 25 billion USD”, replied the young man.

That was Brian Chesky, the founder of Airbnb. The book ‘The Airbnb Story’ recounts that since then Chesky counts Obama as one of his mentors.

The book also narrates another interesting story. Earlier in 2008, Obama had unknowingly helped Airbedandbreakfast(Airbnb’s name back then) survive a near death moment.

With no investor in sight and mounting credit card debt, Chesky and Gebbia(a co-founder) came up with an idea. They were going to make collector’s edition cereal boxes inspired by the presidential campaign. They hot glued 1000 boxes named ‘Obama’s O’s’ and ‘Captain McCain’s’ with cheap one dollar cereal.

Thanks to Obama’s popularity, boxes inspired by him were sold out in no time. This brought in 20,000USD or more, helping the company with a few months’ runway.

Of course, Obama knew nothing about Chesky or his company back then.

See what a few years can do?

So if you are a few months into a new job, startup or a new project that you find rather challenging – don’t quit.

Let time figure out the compound interest for your efforts.

That’s the story. Yes, it’s that short. Save this in your notes and share it whenever you need to provide inspiration to someone.

Three communication tips:

  1. Emotions over numbers: Barack Obama believes that he started becoming successful in politics after he learnt to boil issues down to their essence and convey the emotional meaning of his plans and policies. In your presentations or conversations at work or in business, remember to place ’emotions over numbers’.

So ‘The world has seen 3.3 million deaths due to covid’ may hit harder when you say ‘Over 1 million kids have now lost both their parents to this deadly disease.’ These numbers are hypothetical, but you get the drift.

  1. Go to the source: Brian Chesky of Airbnb has had to evolve faster than most young professionals. His company went from a struggling startup in his living room to a USD 30 billion valuation in less than a decade. To learn and prepare for his evolving roles, he believes in going to the source. He finds someone who has the best knowledge or experience of a subject in his network and gets his answers from him. Maybe something you and I could use too?
  2. Never miss an opportunity to speak: We learn more by doing than by planning and preparing. I have noticed that when I speak at a public forum, I notice many of my shortcomings which introspection would never throw up. That helps me improve.

That’s it for today. Hope you enjoyed the first edition of ‘win with stories’ newsletter. If you have a question about business or personal communication, feel free to reply here or connect with me on Linkedin or Twitter.

Stories mean success. Let’s create many more of them.

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