He quit banking, lost his savings, and then found his startup passion

Yoshi Yokokawa is a fintech pioneer in Japan. You can read about other new fintech in Japan here.

AlpacaDB founder and CEO Yoshi Yokokawa.

Yoshi Yokokawa brings a new meaning to making your money work for you. From a career in banking to losing his savings and being cursed out on stage, Yoshi has finally found what makes him happy.

Yoshi joined the Lehman Brothers Tokyo office full-time in 2005 but was hesitant to tell me exactly what he did. “We were making products out of consumer risks,” he says. Spoken like a true politician, but eventually the truth came out, “it was subprime mortgages… home equity loans.”

“You did it! You did it!” I jokingly screamed at him for his role in the 2008 global financial crisis.

Yoshi’s experience at Lehman left a lasting impression on him. “What is happiness?” he thought. “What do I enjoy the most?”

He watched his team and friends fall apart after the downturn. “It was really miserable,” he says. “About three or four people left the team. They became physically ill.”

Yoshi started doing ultimate endurance sports like extreme marathons to stay fit, but the long hours and loss of purpose took its toll. “I felt sick every time I went to the office,” he remembers. “I didn’t find real happiness that I was searching for with money.”

50K for grandma

While weighing up his career, Yoshi’s grandmother’s health began to deteriorate. “She was living alone and not doing well, so I decided to take care of her.” He left his banking position and moved in with her, but it wasn’t all milk and cookies.

I lost a lot of money.

Looking for a way to support himself and his grandmother, Yoshi turned to day trading. “Why not? I was in finance and I can do it from home,” he thought naively. Although Yoshi had a lot of experience in due diligence, he found it hard to keep his emotions in check. “When I was managing my own money, I realized how stressful this is and how difficult it is to keep your logic in place.”

“I lost a lot of money,” he concedes. After blowing US$50,000 in savings, Yoshi found his holy grail in a book. “Oh shit, this book has all the mistakes I made,” he exclaims.

He started to make money but found himself returning to traditional banker hours. He woke up at 2:00 am to prepare for Chicago markets, stayed up until New York close, and then reviewed his trades until finally sleeping at 11:00 pm.

Yoshi reconnected with his super hacker friend who returned to Japan to take care of an aging teacher. They began talking about working from home and sharing business ideas. “I felt that excitement where you talk and your partner understands ten times more.”

I’m sorry, Dave. I’m afraid I can’t do that.

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