He could have been huge in Japan, but wanted to play in the big leagues of Silicon Valley

ChatWork founder and CEO Toshi Yamamoto wants to play ball.

Toshi Yamamoto is founder and CEO of ChatWork, a team chat app for traditional small and medium businesses.

Toshi is a born hustler who learns as he goes. After a successful start in Japan in the days before Slack even existed, Toshi is now eyeing the American market.

Do the hustle

In the late 1990s, Toshi was like any other teenager trying to balance school and an expanding social circle.

Looking for some pocket money, Toshi started an ecommerce site. He searched his room for things he didn’t need and posted them to the website. Surprised that people would actually buy his used items, he went on a cleaning spree until finally running out of stuff to sell.

Next Toshi tried to find other jobs he could do part-time online. He compiled a list of 1,500 such possibilities. He didn’t take any but found that housewives wanted such information.

Most existing jobs paid between US$50 – 300 per month but Toshi sold that list for US$200, marketing it as an investment where part-timers could make their money back after just one month of work.

Following love

At university, Toshi met a girl. “She was from Taiwan. She could speak three languages and was making money off the stock market,” he remembers,

“I was so impressed. I fell in love with her.” He confessed his feelings and pleaded with her, “please be my girlfriend.”

Never one to let failure keep him back, after several refusals, she agreed but with a small catch. “I’m going to study abroad in Los Angeles from next month,” she said.

I didn’t even know Los Angeles was in California.

“I never wanted to go to the US, I wasn’t interested,” laughs Toshi.

“I didn’t even know Los Angeles was in California. East coast? West coast? What’s the difference? I didn’t know anything about the United States.” He ended up taking a year off school to study in LA. It became a turning point for Toshi. “That [decision] woke me up. It was so different,” he says.

‘Make Happiness’

Toshi continued to operate his own online businesses and do consulting.
He graduated from the university and followed the standard employment path of taking company entrance exams.

Model status

Compete with Slack