From Toronto to Tokyo: How To Land A Dream Internship Through 150 Cold Messages

Misaki Funada
4 days ago
5 min read

Updated: 14 hours ago

Aryan Khurana is a business student at Western University's Ivey Business School in Toronto, Canada. Despite speaking zero Japanese and having no Tokyo connections, he landed a role leading international expansion at a fast-growing startup through systematic cold outreach. He's now supporting a matcha export business connecting Japanese farmers with North American consumers.

What you'll learn in this article:

How to systematically find and land startup roles in foreign countries through cold outreach
Why taking calculated career risks pays compound returns
The real cost-benefit of international work experience for your career trajectory

Aryan Khurana didn't speak Japanese. He had no Tokyo connections. No job lined up.

What he had: a $10,000 scholarship, genuine interest in Japanese culture, and willingness to send 150+ cold Slack messages.

Four months later, he led international expansion for Tabechoku, a farm-to-table marketplace connecting 10,000 Japanese farmers with Asian consumers.

The Constraint That Forced Creativity

By his third year, Aryan had completed three respectable, yet unsatisfying, internships (credit bureaus, tech consulting, startup sales). He needed time for self-discovery and, crucially, real international experience to achieve his goal of becoming an international business leader.

Then, a competitive fellowship provided the perfect structure: $10,000 for a minimum four-month work placement in Asia.

The requirements—go somewhere new, where he didn't speak the language—were deliberate constraints designed to prove that if he could secure a job halfway across the world without language skills or a network, he could achieve anything once he had those advantages.

The 150-Message Campaign

Without any connection in Japan, Aryan first joined Slack communities for expats in Tokyo—channels full of designers and engineers interested in working in Japan. He'd mine the introductions channel, cross-reference names on LinkedIn, assess role fit.

If interested, he'd send a direct message:

"Hi, my name is Aryan, I'm a Canadian business student. [Background]. I saw you're at [Company] working on [specific thing]. I'm interested in learning about [related topic]. Open to a 30-minute call?"

The math was brutal but instructive:

150+ messages sent
10 responses
7 actual calls
3 useful introductions
1 job

That 1 came through a referral chain. One person couldn't help but they connected him to Nathan. Nathan connected him to Shota Eda at Vivid Garden. After several "casual interviews" focused on culture fit, Eda became his manager.

"Rejection therapy is good for future business leaders," Aryan jokes.

The lesson: you need volume, but you also need targeting. Generic "I'd love to connect" messages went nowhere. Specific messages referencing someone's actual work got responses.

What He Actually Did

Tabechoku helps small Japanese farmers sell produce directly, bypassing traditional distribution.

Founder Akimoto-san was inspired by her parents' struggles as farmers lacking market access.

Aryan was the first non-Japanese employee; only his manager spoke English among 50 staff.

His role: international sales of Japanese produce, starting in Hong Kong.

The work involved farmer negotiations, distribution, and regulatory navigation, while learning Japanese. Success stemmed from prioritizing mission alignment and granting real autonomy post-budget approval. The company had less cross-functional coordination and more structured company-wide standups.

"The emotional bond to the work was there for everyone," Aryan noted, attributing their hiring to openness towards non-Japanese staff. By his departure, the CEO revealed she'd been taking English lessons for international expansion, and coworkers began practicing English with him. His presence introduced the company to diverse perspectives.

The Compound Returns

The Tokyo experience keeps paying dividends.

A Y Combinator startup manager in San Francisco saw Aryan's resume on the "Work at a Startup" portal. "For a Canadian business student, that's so strange," the manager said. "I just wanted to learn more."

That curiosity led to eight months on the go-to-market team. Now Aryan's supporting a matcha export business with his former manager Eda-san, connecting Japanese farmers with North American consumers. He'll travel to Japan frequently this year meeting farmers.

He has a network spanning Tokyo, San Francisco, and beyond that wouldn't exist otherwise.

More importantly: the confidence that comes from succeeding in an ambiguous, high-constraint environment. "If I can find a job in Tokyo where I don't speak the language and have no resources, what can't I do back in North America where I have all those things?"

The Decision Framework

When choosing between Tokyo and a product management role in the US (with visa sponsorship and relocation), Aryan used a simple heuristic: "When I'm faced between two major life decisions, I always pick the one that gives me the better story."

Not the flashier story. The better story—the one you'll be proud to tell, that shapes who you become, that opens unpredictable doors.

He also thought about risk mitigation. He knew he could return to a Procter & Gamble internship if needed. That safety net gave him mental space to take the Tokyo risk.

"It really depends on risk tolerance," he says. "But you need to be intentional about knowing what you want and actively communicating that. That's the only way to quickly assess alignment."

His three questions for any opportunity:

Can I learn a ton here?
Am I excited to work with these people?
Does this give me the better story?

If you can't answer yes to at least two, keep looking.

What He'd Tell His Past Self

On risk: Figure out what happens if things don't work out. Have a backup plan. That mental clarity lets you actually take the risk.
On intentionality: Be crystal clear about what skills you want to build, who you want to meet, what type of role and company you're targeting. You can't evaluate opportunities without knowing what you're optimizing for.
On finding good companies: Trust your gut. When his eventual manager came to the interview with a custom deck showing how he could help Aryan's career, that was an immediate green flag. "Nobody's ever done that before."
On execution: Join expat Slack communities. Send cold messages. Many of them. Accept that rejection is part of the process. You only need one yes.

Key Takeaways

Systematic cold outreach works when targeted: 150 messages with specific references to someone's work beats 1,000 generic "let's connect" messages. You only need one yes, but you need volume to get there.
International experience compounds differently than domestic experience: The Tokyo internship led to exponential growth: YC roles, co-founding opportunities, and cross-border networks that couldn't have been predicted.
Risk mitigation enables risk-taking: Aryan could take the Tokyo bet because he had a clear fallback. Smart risk-taking requires clarity on downside scenarios.
Mission-driven culture beats perks-driven culture: Tabechoku's team worked hard because they cared about helping farmers, creating sustainable intensity and development.
The "better story" heuristic is underrated: In major decisions, pick the option that creates experiences you'll be proud to share and that shape who you become. These open more doors than the safer choice.

What's next

You now understand how to systematically find and land opportunities. But once you're in, a different challenge emerges: how do you evaluate whether a startup is actually worth joining when you can't rely on internet search or alumni networks?

Next article: How to evaluate startup culture in Japan when traditional signals don't exist—the 3 signals that reveal whether a company will develop you or burn you out, and the questions to ask that expose the truth in 2-3 conversations.

This is Article 1 in a 3-part series on building a startup career in Japan as a foreigner.