Kiyo Kobayashi is slight, soft-spoken and self-effacing, with an unruly tousle of black hair.
The silhouette he cuts is a far cry from Marlon Brando’s Don Corleone, but the 41-year-old could conceivably be called San Francisco’s Japanese startup godfather. He helped seed a community of like-minded immigrant founders who moved halfway around the globe to change the world from the Bay Area.
“I’m too old,” Kobayashi joked about the godfather label. “But I’m living the dream. Doing startups is my passion, and so is helping other founders.”
Through group chats, calls, dinners and daily feedback reports from younger founders laying out their activities, challenges and questions, his aim is to build up a stronger pathway for these entrepreneurs.
Kobayashi also serves as an advisor and an early-stage investor for dozens of startups from Japanese founders. “Kiyo’s Family” is a collection of around 25 Japanese immigrant entrepreneurs in San Francisco and 50 in the wider Bay Area he helped foster.
“We are probably the first generation of Japanese immigrant startup founders in the U.S.,” Kobayashi said. “Every time I see traction and good news, I feel like we should accumulate this value to the next generation.”
Around a dozen people met for a dinner party at the apartment of one of the group’s members on a recent balmy evening, sharing stories and advice over Korean short-rib stew and above the din of standing fans. These gatherings are a common occurrence for the family.
When Japanese business leaders swing through the Bay Area, they will often stop by for a meeting or a meal as a way to glean insight into the entrepreneurial community.
Kobayashi himself has started and wound down a number of companies in the decade since he’s been in San Francisco. He’s currently working on a recruiting startup in the Web3 space, but his larger project is working to develop a sustainable pathway for Japanese immigrant founders.
Forging a Path
Kobayashi became a known figure in the Japanese business world when—spotting the coming opportunity enabled via smartphones—he founded Nobot in 2009, one of the country’s first mobile advertising companies. The real sea change came when he ended up selling his startup a couple years later to major telecom corporation KDDI for $19 million.
“It was essentially one of the first successful case studies of [mergers & acquisitions] in Japan,” said Kaz Tamai, founder and CEO of startup design firm Zypsy. “Back then, everyone thought M&A was a betrayal because you were passing along ownership to someone else. It was like selling your family.”
But Tamai said the sale proved that the startup model could work and helped provide the foundations for what is increasingly becoming a thriving domestic startup ecosystem. According to data from Initial Enterprise, total venture capital funding in Japan has grown more than 16 times between 2009 and 2021, rising from $130 million to $2.2 billion.
Kobayashi tried to take Nobot international but was stymied by the domination of American tech giants like Google. The roadblock helped inspire him to move to San Francisco to create a company that could have global impact.
To hear it from Kobayashi, he arrived in the city in 2013 with no connections, no English skills and, really, no idea. His first stop was at language school to help him learn to communicate.
“In Japan, I was connected with pretty much every startup founder and investor,” Kobayashi said. “But when I moved here, I was treated like an elementary school kid because I couldn’t speak English.”
Kobayashi notes that a community of Japanese founders at the time was virtually nonexistent, a stark contrast to the strong connections made among immigrant entrepreneurs from Asian countries like India, South Korea and China.
Those early days were filled with plenty of discomfort and shame. Kobayashi said he was scammed a few times by those offering to provide connections or help with the business and visa processes. Through painful trial and error, Kobayashi was able to build up the right set of contacts to help others in his situation with business incorporation and immigration issues.
One of his early protégés was Satoru “Steve” Naito, the CEO of Anyplace, which offers furnished apartments with high-speed internet for remote workers. Naito was writing a blog about his experiences in Silicon Valley after he arrived in 2014, and Kobayashi reached out to connect.
Kobayashi helped inspire Naito and a handful of entrepreneurs like Tamai to root themselves in San Francisco instead of retreating back to Japan and provided meals, advice and some initial seed funding. The group would often tag-team meetings together to help one another communicate with limited English skills.
“When I moved to San Francisco, I didn’t speak English. I didn’t have money. I didn’t have friends,” Naito said. Ordering a cup of coffee at Starbucks was a challenge, Naito said, and often led to cloyingly sweet drinks.
To help build a home base for the community, the group started a shared house in Balboa Park that worked as a living space for Japanese founders. Although described lovingly by Naito as a crowded and messy dorm, the home accommodated hundreds of prospective founders and visitors.
“It became a good place for Japanese people to land in San Francisco and be together and exchange information,” Naito said.
The group also continued to write for a Japanese audience, blogging online about their experiences in Silicon Valley and interviewing other founders and members of the local tech industry to spread word of their activities.
Kohei Nagata, founder of blockchain startup Senate, said he was inspired to come to San Francisco five years ago after reading Naito’s own account of moving to the city despite not knowing any English.
He started speaking to Kobayashi after connecting on social media. What started out as occasional conversations during household chores turned into daily feedback sessions.
“There were times when there was no point in using his time to help, when I had no hope literally,” Nagata said. “But he still kept trying to give me advice every single day.”
Nagata didn’t hesitate to say that, without that line of support, he would have already left the city.
“In order to keep grinding for that startup dream,” he said, “you have to believe in yourself, sure, but you have to have someone who believes in more than you do yourself. That’s the feeling Kiyo gave me.”
Family Time
Kobayashi lives in Mission Bay with his wife and two small children. More than a dozen other entrepreneurs have moved to his apartment building or his neighborhood to be nearby for advice and a stronger network of support.
Kobayashi's mentorship provides a warm embrace for many folks who move to San Francisco with few connections. He and his wife host regular events like barbecues or weekend trips, and he said he considers the community of founders part of his extended family. He also brings together small groups of founders at the start of each year to set their intentions and share their learnings and mistakes.
Datz Daito is an entrepreneur who was drawn to building a global tech startup in San Francisco, moving to the city as a teenager in 2019. Daito runs DeStore, an apparel shop in Hayes Valley that operates with a collective decision-making model by the company’s members.
Instead of rooting around in the proverbial darkness, these immigrants found that Kiyo’s Family provided a way to plug into investors, mentorship and a place to live. There’s a team spirit that fosters a feeling of camaraderie. A win for one founder is a win for their entire family.
“If anybody’s successful, they add more value to the overall ecosystem, and the probability for success for everyone is higher,” Daito said.
Sumino Koiso, found her way into the community during her first trip to San Francisco through her mentor, who is a member of Kiyo’s Family. Now, she relies on their connections to find trustworthy accountants and lawyers to guide her through the visa process.
Her working theory on why there’s been only a limited number of Japanese immigrant founders has to do with a discomfort with speaking English in professional settings and a cultural fear of failure, which leads to calculated risks rather than the wide swings in fortune seen in Silicon Valley.
There’s also the relative geographic isolation of Japan, which has a strong domestic economy, as well as an internal business culture difficult to penetrate for outsiders.
She struggled to find the right words to characterize how she and other members feel when returning to Japan, so she used a translation app on her phone.
“Societally unfit,” the screen read when she turned it around. “We’re different because we can take these risks and tell our thoughts directly which for some Japanese people make them uncomfortable.”
Although there have been a handful of Cinderella stories for Asian immigrant startup founders like Zoom’s Eric Yuan, that level of success has thus far eluded Japanese immigrant entrepreneurs.
Kobayashi believes that the Japanese are great at following role models, but someone needs to act as a trailblazer. He wants to be part of the team proving that having success is possible. For an analogy, he turned to baseball’s Ichiro Suzuki, who was the first Japanese position player to find success in Major League Baseball.
The startup journey is, for the most part, defined by failure. And many entrepreneurs in the network said Kobayashi’s most valuable advice was in dealing with personal and business failures and giving them confidence to move forward.
Kobayashi has weathered his own share of failures in his entrepreneurial journey. On particularly rough days, he’ll pop into a neighboring apartment where a number of Japanese founders live and work.
“I’ll have dinner with them, and I’ll ask if they have any problems that I can help them with,” Kobayashi said. “It’s confirming that the reason why I am a founder and an entrepreneur is to help others.”