I’ve got a challenge for you…

652 startups on AngelList are based in Tokyo, Japan.

In 2 weeks, can you book meetings with 10 of them — using only cold outreach?

Let’s make it more interesting…

You can’t use your connections to make an introduction for you.
You have to play by Japan’s email laws. (Or risk 1 year in prison or a $3.7 million fine.)
Oh, and you can’t communicate in Japanese.

Think you can do it?

That’s the question Jeremy and I asked ourselves 2 weeks before we landed in Japan.

We were travelling to Tokyo to record our course on cold email. So we thought this would be a fun challenge to test if our outreach strategies worked halfway around the world.

What happened?

In 7 days, we scheduled 19 meetings with startup founders in Tokyo using a 5 sentence email and a simple outreach strategy.

This post explains how we did it.

(Feel free to use the same approach to connect with anyone, anywhere.)

Step 1 – Define your goal

Before we wrote a single email, we had a 60 minute skype call to go over our goal for this challenge.

Important: Our goal was not to book 10 meetings in 2 weeks.

Sure, that’s what we wanted to achieve in the end, but it would have been a terrible goal for this challenge. Why?

We needed a goal that was 100% in our control.

If you’ve ever sent a single cold email, then you know getting someone to reply is not in your control.

Sure, you could write an incredible email and send it to the hottest prospect in your industry, but you don’t get to decide if they open your message, send you a reply, or book a meeting with you.

However, we could control how many emails a day we send and who we send them to.

So we asked ourselves, “How many emails do we need to send, per day, to give us the best chance of booking 10 meetings in 2 weeks?”

Math time.

We estimated that we’d get a 10% reply rate.

Of those replies, we estimated that 50% of them would be positive.

Out of those positive replies, we estimated that 25% of them would lead to a meeting.

Still with me? Good.

So… In other words, if we contacted 1,000 people, we’d get 100 replies, 50 positive replies, and 10 meetings.

So in other words, to get 10 meetings, we would need 40 positive replies.
To get 40 positive replies, we’d need to get a total of 80 replies.
To get 80 replies, we’d need to contact 800 people.

Divide 800 by the number of days we had (14) and we knew that our goal was to contact 57 people a day.

Goal: Contact 57 Prospects a Day for 2 weeks or until we book 10 meetings.

Now that we had a clear idea of what we needed to do, we started researching to figure out how to get a Japanese startup founder to reply to our message.

Step 2: Research

We needed to answer 2 BIG questions during our research efforts:

1) What email content will most likely get a reply
2) What country-specific email laws are in Japan

We learned a few game-changing facts during our research phase.

1) We learned that cold email was illegal in Japan. And carried some heavy fines/jail time penalties for people who broke the rules.

2) We asked on Quora “How do you could email Japanese startups” and got back some rough answers.

“a cold call will be rejected 99.99% for just being a nuisance, etc.”
CEO at consulting firm, living in Tokyo for almost 30 years

“Cold Calling is Japan is VERY uncommon. The possibility that you will actually achieve a business meeting within the 3-4 weeks you will be in Tokyo are slim to none.”
Company owner, living in Japan

So we had to adjust a few things. But we did learn 2 tips that ended up playing a huge role in our outreach success:

1) In Japan, it’s important to be humble. An arrogant tone in an email could crush your chances of landing a meeting.
2) Japan’s sales cycle is loonnng. In fact, talking “business” typically doesn’t happen until a face to face meeting is in progress. So we knew our Call-To-Action had to be conversational and miles away from sounding “salesy”.

Step 3: Prospecting

To contact 57 prospects a day, you need, well, prospects.

So we set out to build a list of the startup companies in Tokyo. This was pretty easy.

Just go to angel.co/tokyo and you’ll see 652 companies.

Now, normally, you’d go to work finding the email address of the founders of those companies. But since cold email is illegal in Tokyo, we decided to:

Check their website to see if a public email was given. (It’s legal to contact an email if it’s shared on a company website.)
If no email was listed, use the contact form on their websites to deliver our message.


We could have stopped there. After all, we have a list of startups in Tokyo.
But there’s another segment we targeted called “VIP’s.” These are ultra-connected people that were running incubators, startup meetups and investors who had the power to connect us with 10+ meetings in 1 shot.

This was a much smaller list, but it deserved lots of attention because of the potential pay off.

To build our list of VIP’s, we found startup/tech MeetUp organizers, business incubators and prominent investors in Tokyo. Same email rules applied to this group, so we had to contact them through their website contact form — unless their email was publicly available on their site.

Step 4: Email content

2 things we used from our research notes to write our emails:

1) The emails are quite humble. If we came across as “braggy” or arrogant, we would have killed our chances of getting a reply. (This is not exclusive to Japanese companies. However, we had to be extra careful on which facts we included to establish our credibility.)

2) The CTA (call to action) respects the fact that sales should not be discussed until a face-to-face meeting. In fact, it doesn’t even mention setting up a meeting. It’s simply getting a conversation started. The conversations led to booking meetings.

IMPORTANT: The people on the VIP list got completely custom emails. Why? Their was only 8 people on our VIP list, so spent 2 hours crafting individual emails to increase our chances of getting replies.

Step 5: Deliverability

Now that the emails were written, it was finally time to send ‘em out.

During the prospecting phase we identified the websites of 652 startups in Tokyo.

We ran each domain through a google search to find the contact page for each site.

site:example.com inurl:contact OR inquiry would return the contact page for 80% of the sites.

All others we ran through a scraper to find the publicly available emails to contact them using Quickmail.io.

After we had the contact form, we had a VA go through each one and fill out the form for us. It took 2 hours 10 minutes at 5.90/hr.

It helped save time by finding the contact page because most sites were in Japanese.

Next time, I would have build a web crawler in Python to automatically find the contact page and submit our contact form.

Step 6: Booking meetings

Once somebody replied, they got a personal reply so we could address the specific questions/ideas that they mentioned in their reply.

Handling replies is where we spent most of our time during this outreach effort. It was worth it, because we were now dealing ONLY with founders who responded with interest.

Plus, we knew if they agreed to exchange a few emails, they would be more likely to set up a meeting in person.


This outreach challenged proved that you can start a conversation (and book meetings) with practically anyone using cold outreach alone.

It doesn’t matter if you don’t have a mutual connection.
It doesn’t matter if you are new to the industry.
It doesn’t matter if your reaching out to people 5,000 miles away.
And it doesn’t matter what haters say on Quora about cold email.

So what’s stopping you from connecting with anyone?