Leaving Behind Silicon Valley: Launching an AI Venture in Tokyo as an Expat

Seeking a new beginning, I relocated to Tokyo last year.

Exploring a New Market

California had lost its allure for me; the exorbitant cost of living and the fading spirit of the Bay Area made it clear a change was necessary. My previous visits to Tokyo left a lasting impression with its orderliness, safety, and dynamic atmosphere.

An intriguing aspect of Tokyo is its landscape dotted with over three million small enterprises, such as eateries, bars, cafés, and shops. Unlike in America, where large corporations reign, Japan thrives with numerous family-run businesses. This makes Japan an ideal testing ground for my concept.

In 2024, my initial visit was a temporary three-month stay. With no personal ties to Japan, such as familial roots, language skills, or heritage—I hail from a Hong Kongese background—the move was a leap of faith. I believed success here would mean success was possible anywhere.

Deciding to Move On from New York

My upbringing took place in Brooklyn, New York, in a modest, working-class family. My father, who migrated from Hong Kong, undertook numerous jobs throughout his life, including waiter, limousine driver, and FedEx employee. At one point, my parents even managed a restaurant.

Despite my family's hopes for a conventional 'white-collar' career, entrepreneurial spirit was ingrained in me. I pursued advertising and public relations at Penn State, but it wasn't long before corporate confines pushed me towards startups. Opportunities to innovate and lead teams presented at an advertising agency convinced me to explore company building further.

Embracing the Challenge in San Francisco

The initial ventures I pursued—a job site for visa sponsors and a travel camera app—didn't find their footing. This, paired with the dreariness of corporate roles, made clear that I needed to pivot. The intense competition characteristic of the Bay Area was palpable, but working in a fast-paced data company honed skills valuable in pursuing market share.

By 2019, I co-founded my first venture with two former colleagues, developing tools for engineers using AI before it was widely recognized. Although successful initially, the unpredictable nature of startups, further complicated by the pandemic, led to our exit. Following this, I ventured into the restaurant business, managing multiple eateries in California before automating operations.

Eventually, I entrusted managers with these enterprises and shifted focus to my fresh startup, Colega AI. Founded in the US, our operations revolve around crafting AI-driven marketing solutions tailored for small businesses. Despite being an American company, the team primarily operates out of Tokyo, reflecting our remote-first culture.

Adjusting to Japan's Professional Environment

My relocation to Tokyo has been both rewarding and complex.

To bridge cultural and linguistic divides, I've collaborated with a local expert, ensuring smoother engagements within Japan's formal business landscape. Concerns about acceptance as a foreign entrepreneur lingered initially, as Japan highly values tradition.

The work life here contrasts sharply with that of San Francisco. Familiar faces keep pillows at their workstations for office naps—a testament to long hours and entrenched hierarchies. As a founder, I've had to integrate this cultural respect with a more agile startup atmosphere.

My spouse, Shana, whom I met in San Francisco, has seamlessly adapted, delighting in Tokyo's security. Her jewelry business also adds to our rich experiences here, though developing friendships is a slower journey amidst language challenges.

We've settled into a roomy apartment near Shibuya, notably costing nearly half the rent of our Californian residence—$1,350 for 500 square feet. Compared to San Francisco's rates, this is significantly economical.

Despite the apartment's cozy size by American measures, it offers wonderful convenience—whether indulging in late-night ramen or accessing speedy transport. Everyday expenses, especially on dining and groceries, are quite reasonable, though certain items like fruit can be surprisingly costly.

The future remains open-ended. Whether Tokyo remains our home for the long haul or we venture to other parts of Asia or return stateside eventually, we'll decide as events unfold.