Home Is Not the Point.

Three Investments, One Pattern

Over the past six months — from last autumn through this spring — I made three new angel investments. On the surface, they have little in common. One is building an AI-powered credit infrastructure for immigrants. Another runs a travel business with operational excellence at its core. The third is creating a peer community platform for early-stage founders. Different sectors, different stages, different geographies.

But when I stepped back and looked at all three together, a pattern emerged — one I hadn’t planned, but one that turned out to be the clearest articulation of what I believe in as an investor.

All three use AI. All three were founded by people who left their home country to build something elsewhere. And all three have a deep connection to Japan — either through their founders’ roots or through where they chose to land.

Dwilar: When the Immigrant Becomes the Founder

I first met the founder of Dwilar at IVS Kyoto in 2024, through a mutual connection. Honestly, I wasn’t immediately drawn in. But when I heard his business model, something clicked.

Here’s his story. As a university student in Kobe, Yoshitaka Nakamura had built and operated over a dozen after-school learning centers for children of immigrants. These were bright kids — talented, capable — but because their Japanese language skills lagged behind, they couldn’t keep up in public schools. The city of Kobe recognized the problem and funded the program through grants. It was working. Then the mayor changed, and the grants disappeared.

He went on to work at Toyota and P&G, then earned his MBA at UC Berkeley. And that’s when the tables turned. Suddenly, he was the immigrant. No credit history. No local track record. Trying to rent an apartment or get a credit card in the US felt nearly impossible.

That lived experience became his startup. Dwilar uses AI to analyze immigrants’ economic data from their home countries — the financial track records that exist but are invisible to American landlords, property managers, and financial institutions. He is solving a real problem, born from real pain, on both sides of the Pacific.

Retreat Technologies: The Quiet Strength of Operational Excellence

I was introduced to one of the co-founders of Retreat Technologies through a mutual acquaintance — another Japanese founder building in the Bay Area. Their business is in the travel space.

Now, you might wonder: travel is a mature industry. Expedia, Booking.com, and other giants already dominate the market. Where is the opportunity? But here’s what the founders spotted — those incumbents are all B2C players. On the B2B side, there is a wide-open gap. Corporate travel, group retreats, team offsites — this is a space where operational excellence matters more than flashy consumer branding. And I thought: isn’t that precisely where Japanese founders have a natural edge?

What tipped the scale for me was the founders themselves, Shun Yamada and Jack Tadami. Two people of deep integrity, the kind you trust to hold steady when things get hard — and in startups, things always get hard.

I didn’t have a grand strategic thesis when I invested. It was more of an intuition — a sense that this company would connect to something larger. And as it turns out, pieces are starting to come together in ways I couldn’t have predicted at the time.

Entention Social: Diamonds in the 97%

The third investment has the longest backstory.

The founder, Philip, is a Vietnamese-American who earned his PhD in nuclear engineering at Kyoto University. He fell in love with the city and stayed. I first backed him years ago, when I was running a fund at Sunbridge in partnership with Hankyu Railway. That company was Gochiso — a platform where dining at participating restaurants would automatically direct a percentage of your bill to an NPO of your choice. It was a beautiful idea rooted in his passion for social impact, but it didn’t scale. He put it into hibernation.

But Philip kept going. His next venture was a product to help small businesses visualize and display their CO2 reduction efforts — a sustainability play. It got accepted into an Estonian accelerator, and things were moving forward. Then Trump 2.0 happened. Across the US, renewable energy startups that had been counting on government grants saw their funding evaporate. Philip had to pivot again.

What he landed on this time, I believe, is the most promising idea yet. His insight is simple but powerful: seed-stage founders are overwhelmed and isolated, with no one to talk to. The accelerators — YC, Techstars, and the rest — serve roughly 3% of startups. But what about the other 97%? Among them, there must be diamonds in the rough.

Entention Social is building a peer community where early-stage founders can support each other — practically and emotionally — without needing to win the accelerator lottery first.

This resonated with me on a personal level. When I founded DreamVision in 2006, I originally wanted to build an EdTech platform — specifically, a platform where practitioners learn from each other. I did my own feasibility study and concluded that Japan wasn’t ready. The idea of embedding entrepreneurship into university curricula seemed impossible at the time. I shelved it.

Fifteen years later, in 2021, Yoichi Ito invited me to help create the School of Entrepreneurship at Musashino University. I said yes immediately. It felt like a message from the universe — the idea I had abandoned had come back in a form I never expected.

So when I saw what Philip was building with Entention Social, I felt the same resonance. The founder who refuses to quit. The idea that keeps finding new shapes. And at its core, a belief I share: where diamonds shape themselves.

What Connects Them

I didn’t set out to build a portfolio around a thesis. These three investments found me — or perhaps I found them — through the network of relationships I’ve built over 25 years as an entrepreneur and investor in Japan.

But when you look at them together, the thesis is clear.

The most interesting founders I meet today are not the ones optimizing for a single market from within. They are the ones who have left home — by choice or by circumstance — and are building at the intersection of cultures, languages, and systems. They carry the discipline and integrity of their roots, but they refuse to be confined by geography.

Japan, as I have written before, has a structural handicap as a relatively mono-ethnic nation in a globalizing world. But these three founders — and many others like them — are the living proof that the handicap is not destiny. The future of Japanese entrepreneurship may not come from Tokyo alone. It may come from Kyoto, from Berkeley, from Tallinn — from wherever founders with a connection to Japan choose to build.

Home is not the point. The building is.

Thanks for reading. If you know founders building across borders with a connection to Japan, I’d love to hear from you.