13 years of hustle: how Jay Winder built the only company in Japan backed by AngelList

Jay Winder speaker at a HackerNews readers meetup he organizes

Life is good for Jay Winder in 2015. His second company – a fintech firm called MakeLeaps – is integrated with Evernote, serves prominent Japanese clients like Rakuten and Voyage Group, and is on track to becoming profitable. He is a familiar face in Tokyo’s startup scene, where his natural friendliness and fluent Japanese wins him plenty of fans. He is even entering the year with some nice momentum, only a few months removed from a US$750,000 funding round that included AngelList founder Naval Ravikant and 500 Startups founder Dave McClure. The signs are all pointing up, but journey did not happen overnight. For Winder, it has been a story 13 years in the making.

Japan ho!

Australian, affable, and with a gift for tackling internet technology problems, Winder was hired by the IT department of Ernst & Young Australia in 2002 at age 18. By age, his closest coworkers were 10 years older than him. He had been given a unique opportunity to skip college and immediately start working with a highly-talented team for one of the most respected companies in the world. But that was not the life he chose.

“Three months later, I quit that job to follow my dream of going to Japan to study martial arts. Everyone told me I was an idiot to quit, since they couldn’t believe I’d gotten the job in the first place. My boss at Ernst & Young even offered to give me a promotion to get me to stay, but my heart was set on Japan,” he recalls.

Bujinkan Taijutsu is a defense-minded discipline that was one of the many tricks ninjas would keep up their sleeves. Winder’s martial arts studies would not last long, however. He had the entrepreneurial bug, and in September of 2003, his first company opened for business.

Webnet IT, which is still running today, is a bilingual IT services company for firms which don’t have the right personnel to handle their tech issues. Winder doesn’t have any regrets about dedicating his time to becoming an entrepreneur. He sees it as an extension of his core personality: someone who enjoys finding solutions to thorny problems.

Enter MakeLeaps

That stubborn inquisitiveness lead Winder to create MakeLeaps. In 2005, he was having trouble managing Webnet IT’s invoices. The solutions he found were not well suited for Japanese currency or language. So he prototyped a system and hired a developer to build it.

“The first version of the system was barely functional, since I was so inexperienced at designing and building software. Over a few years I got better at it, and the system got a lot better. Finally someone said to me, ‘I don’t care how much this costs – 50,000 yen, 500,000 yen, 5 million yen – I NEED this solution. My business is being run on Excel, and I have no idea what’s going on, or whether I’m profitable or not,’” he says.

The process took years. But after determining that the invoicing software did have a solid product-market fit, Winder brought Paul Oswald, a former Sony employee who Winder met via HackerNews, onboard as a technical co-founder. In 2010, Makeleaps went live as an additional service offered by Webnet IT.

Over the next several years, the team worked on improving the core product and improving the user experience. Winder eschewed advertising spend in favor of getting new clients via word of mouth. Now, MakeLeaps purports to be the only invoicing solution that is both bilingual and compatible with 13 currencies. Ultimately, the service grew big enough (15 employees and thousands of companies using it monthly) that Winder decided to incorporate it separately in July 2014.

The MakeLeaps team