After sacrificing his car and all his assets, will the Crowdworks CEO be rewarded with a $100 million funding round?

Koichiro Yoshida, CEO of Japanese freelancer marketplace Crowdworks, has thrown everything into his venture.

Before starting his firm, he liquidated his assets in order to give himself an extra mental edge. If he owned nothing to begin with, he would have nothing to fear losing. Two years later, his bold approach paid off. Crowdworks has delivered approximately US$110 million worth of client projects and has a current tally of 33,000 companies and 180,000 freelancers registered on its network. Yoshida’s vision of the future? Conquering Japan and expanding throughout Asia, while keeping fear in the rearview mirror.

Known for his quick wit, Yoshida comes off as a natural born entrepreneur. He insists, however, that nothing could be farther from the truth. “When I was growing up, founding a company meant that you did not fit in and needed to drop out of society,” he explained.

Entrepreneurship may have had a social stigma but that could not suppress his innate affinity for imagination and creation. As a child, he would physically make playing cards to be used for Monster Hunter-style card games and even develop his own mecha-inspired science fiction comic books. In college he became the leader of a theater troupe – writing, acting, building sets, and directing productions. He intended to make his career in the creative arts but he would soon learn how hard that transition could be.

Learning the first step of entrepreneurship – making the sale

Yoshida’s dreams of earning a living in theater dissipated when he failed to follow through on the terms of a contract. He had been leading his troupe of thirty for six months in preparation of opening a play but, due to his oversight, the production was cancelled and he fell into debt. Though he blames himself for not being more careful, he believes that his failure was avoidable.

“In Japan, there is a strong culture of mutual support, but up through college, we don’t teach kids much about the real world,” he observed. Chastened by the experience, Yoshida grew determined to enter the workforce and become a proper businessman.

After graduation he entered digital entertainment conglomerate Pioneer and set out on his career as a salesman. Success at Pioneer translated into a management position at Reed Exhibitions Japan.

But by the time he turned 28, Yoshida’s mind returned to his long-forgotten entrepreneurial ambitions. If he decided to abandon his current executive-track career path would he be considered just another guy who couldn’t cut it in Japanese society? Yoshida had his doubts. “My parents said that entrepreneurs were dropouts but every company needs a founder. Are all the founders of [major companies] JAL, ANA, and Sony dropouts?”

Always get back up

Yoshida’s early forays into entrepreneurship were scattered and unfocused. He took a crash course in entrepreneurship and business development at Attackers Business School, a local school for would-be entrepreneurs that counts tech luminaries like Kenji Kasahara, the founder of Mixi, among its alumni. True to his new alma mater’s name, his entrepreneurial assault was nothing if not aggressive.

Prior to hitting a winner with Crowdworks, Yoshida had founded and managed thirteen different enterprises, some concurrently. Due to his gifts as a salesman, he was generally able to keep the businesses afloat but was not able to scale them into a stable entity. Yoshida’s most ambitious gambit? Angling to build a planned city in the middle of Malaysia. That plan was ultimately shelved when he blanched at the expected 60-year completion time.

The youthful optimism of his early days are not lost on Yoshida. “If I think about it now, maybe I was a bit foolish… but I wanted to give it a shot, “ he said, also noting, “If you think through everything logically, you will likely predict your own failure and decide not to start.”

Building a winner

Crowdworks began when Yoshida realized he could take advantage of a rising interest in crowdsourcing to return to his lifelong love of working with creators. Upon its debut in March 2012, Crowdworks was almost an instant hit, gobbling up funding rounds of US$3.75 million in October 2012 and a further $10.7 million in December 2013. Yoshida credits that success to very calculated preparation prior to the service launch. Unlike most entrepreneurs who build their service, show it around, and then adjust in accordance with customer needs, Yoshida wanted to have a service that was ready for customers from day one.

What next for a man without fear?