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Hello World | Entrepreneurship is hard. Successful founders make it easier by adding playfulness to the mix

Many times entrepreneurs become too serious and get bogged down by the headwinds they face. This can be counterproductive.

October 21, 2021 / 08:26 PM IST
(Representative image) Atlassian founders Mike Cannon-Brookes and Scott Farquhar used rock-paper-scissors to make decisions they were tied on.

(Representative image) Atlassian founders Mike Cannon-Brookes and Scott Farquhar used rock-paper-scissors to make decisions they were tied on.

Note to readers: Hello world is a program developers run to check if a newly installed programming language is working alright. Startups and tech companies are continuously launching new software to run the real world. This column will attempt to be the "Hello World" for the real world.

hello-world-logo-258x258Mike Cannon-Brookes and Scott Farquhar have a company that does serious business. They started a tech support company in 2001. Mike and Scott worked nights and days until they landed on a hit product called Jira, which helps companies manage projects, track bugs and such. The two were in Sydney, Australia. Which meant they didn’t have access to venture capital or mentors like Silicon Valley companies.

They worked really hard. Atlassian, the company they founded and grew against all odds, now has a market cap of over $100 billion. That puts them in the league of the greatest companies in the world. 

Dan Kurzius and Ben Chestnut founded a web design agency in 2001. Eventually, they landed on an email marketing product called Mailchimp. In September, financial software maker Intuit acquired Mailchimp for $12 billion. The startup, founded in Atlanta, also bootstrapped to success. Which means their early days were tough. 

Xiaomi, one of the world’s largest smartphone makers, has become wildly successful on the back of the hard work of its founders and employees. Xiaomi’s founder Lei Jun’s work ethic is well known. Blackberry, the Canadian phonemaker which was wildly successful, was founded by Mike Lazaridis and Douglas Fregin with some serious technology chops. 


Freshworks, the company that I work for, makes enterprise software that thousands of businesses rely on. Last month the company went public. Again, serious business built by great people. 

These companies and founders are very different from each other. The obvious thing about all of them is that they’re all hardworking people. But if you study them closely, all of them have one common trait. They understand the value of ‘Play’.

Mike and Scott would play rock paper scissors if they were tied about a decision. In fact, they added the rock paper scissors method of resolving ties to their first shareholders' agreement. 

The Mailchimp logo and persona was designed around the playfulness of a pet monkey that Ben’s parent’s once owned. At their web agency, they’d throw in concepts with monkeys in them in client presentations. On particularly long and unfinished projects, they’d joke “let’s put some monkeys in there”.

Xiaomi’s mascot, Mitu, a white rabbit wearing an Ushanka, is indicative of a similar playfulness its founders wanted to instill in the company. They’d obsess over details but strive to build a playful relationship with their users, and also within the company. 

Blackberry’s founders wouldn’t chastise a senior executive for coming into a meeting late but made the same point by playfully suggesting that the latecomer buy donuts for everyone. It became a culture at Blackberry to come on time for meetings. 

Girish, the founder of Freshworks, has codified “Happy workplace” into the company’s values. The emphasis being on work. “We should celebrate small wins and try to create a happy work environment,” he’d say to employees. 

The import is that many times entrepreneurs become too serious and get bogged down by the headwinds they face. As time passes, morale takes a beating. But some of the most successful founders try to make it easy on themselves and the people who work with them by introducing a bit of play into the mix. Entrepreneurship is hard. Don’t forget to have fun on the journey. Or the joke is on you.
Jayadevan PK is a storyteller who focuses on business and technology. His first book, Xiaomi: How a Startup Disrupted the Market and Created a Cult Following, was published by Harper Collins in April 2021.
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