by Theo Strauss

The Emailer’s Guide To The Galaxy: Part II

As I explained in my last post, I’m 17, so my network isn’t too big just yet. For me, cold emails are the easiest and most direct way to reach a founder. Over the past year, I’ve sent over one hundred emails to CEO’s, founders, and heads of design, and have gotten a response from over 80% of them.

My emails started out unconventionally — filled with long paragraphs, massive intros, and frankly, very little about the recipient. But, with A/B tests, just the right amount of analytics, and persistence, I was able to notice what stuck.

Most people just assume they’re bad writers, others think it takes a degree in communications. Not me. In this post, I’m going to give you a play by play handbook on what I learned in the past year. And, by the end, you should be able to lock down a meeting with whomever you want.

The email address

Depending on whom you’re emailing, the address you choose to send your email to can decide your fate.

Why? I get into this in the first post of this series - How to find any CEO’s email address in minutes. I touch on deciding which email address to use in the first part of that post. You should probably read that before getting into this one.

Composing the email

The subject line

In the world of email, the battle starts before your message is even opened.

It’s your subject line against the rest in their inbox. You’re a mere peasant among the hundreds of others vying for the king’s attention. To get in front of the throne, to have the king hear your thoughts, the subject line of your email has to be perfect. There are two ways of going about this:

  1. The trojan horse
  2. Knocking on the front door

The trojan horse strategy is another name for camouflaging. Here’s an example:

What do you think?

Remember, with hundreds of emails coming in a day, the CEO you’re emailing skims their email for the ones that need the most attention. This subject line blends perfectly into the myriad of other work emails they’re receiving.

“What do you think?” can apply to a proposal that needs looking over, a meeting that needs confirming, or a random question. Consistently clicking on subject lines similar to this one might get your email opened.

Knocking on the front door is the complete opposite of the trojan horse. These types of subject lines are perfect for a pitch or if you stand out and can take advantage of that. Here’s an example:

$10 million in revenue 1 month in, now I need your help

This is complete clickbait, but it can pay off in big ways. The rest of this post will guide you in keeping their attention now that you’ve grabbed it.

The greeting

“Hi,” “hey,” “hello,” “what’s up,” “yo,” “dear,” “good morning,” “whomever it may concern”. The first two words of your email set the tone for your entire note.

That’s why deciding which greeting to use is crucial. The one I’ve found the most success with is “Hi [first name],” and Business Insider agrees. This is because it’s not too casual (For example, “hey” or “what’s up”) and it’s not too formal such as “dear” or “whomever it may concern.”

It’s ultimately up to the person you’re emailing, though. When they respond, they might use a different greeting than you. From then on, use their greeting while emailing with them. If they respond with the same greeting, you hit a home run.

The first line

You’ve convinced the person you’re emailing into looking at your note and you set the tone with the greeting. Now, it’s time to grab their attention.

Here’s a look at the line I use:

I’m not a normal kid. I’m 17, go to the Dalton School, right uptown from [insert their company here], and I’d love to ask a question.

Let’s break that down. In one sentence, I’ve said:

  1. Who I am
  2. Why I’m different
  3. How we’re distantly related
  4. What my purpose is with this email

CEO’s don’t have much time, and they have even less for people they don’t know. Captivating them in the first sentence is key.

The bolded words are the most important. Being 17, a kid, sets up who I am and what makes me differenct. Because I’m local to where they are, it gives them an incentive to learn why I’m reaching out to them. And, instead of just saying “Hi, nice to meet you”, I’m declaring that I have an intention.

Let’s look at an example opener:

I’m a junior at Stanford, 95% of the campus is on my app, and I wanted to talk about YC.

The same four keys appear in this sentence. The sender is a Stanford student, they’re different because of the number of users they have, the example recipient is a Stanford alum, and has gone through YCombinator.

The first sentence is setting the stage for the rest of the email and offers a quick preview from the inbox. On that topic, here’s how much preview space there is for different email clients.

Apple Mail: 140 characters
Gmail: 110 characters
AOL: 75 characters
Outlook: 55 characters

The example above has 88 characters, and if you include the subject line, it’s 109, just below Gmail’s cap.

The bio

Here’s one thing to keep in mind while writing an email: just like it was a fight to get your email clicked on, it’s still a fight to have them read line after line of the body. Captivating your reader with every paragraph is essential.

The key to making the CEO read each line is to draw connections between the two of you. With more in common, the recipient will want to keep reading, just to see what sets you apart. It’s exactly like how getting a job is easier if you went to the same school as the founder of the company.

The bio is the place to do that. While making connections, you’re also touting everything you’ve done that’s impressive and how you’ve gotten to where you are.

The trick to making those connections in each paragraph is research. I recommend you find five links about the founder, CEO, or person you’re reaching out to before even starting your draft:

  • 1 interview with them
  • 2 articles covering them
  • Their website / about page
  • Their LinkedIn (past companies, education, volunteer work, and contact info)

On each page, you’re bound to find one piece of information that helps your case. Whether it’s a shared city or school, or even if you have a friend who worked for a company they did, it’s helpful to put that in your bio.

Here’s an example of the bio I used for my last email:

New York has taught me to take a deep interest in the world around me: the energy, the innovation, and the perspectives.
A couple years ago I started to brand companies, one of which Hillary Clinton Instagrammed about, which led me to start designing apps, creating solutions to New Yorkers’ daily problems.
To bring them to life, I taught myself to code, which landed me at WWDC as a scholar.
Meeting founders there, I started to conduct case studies, looking at how design can help solve problems the future poses, looking at how ride-hailing can be made more accessible.
After WWDC, during the summer, I Citi Biked across the Brooklyn Bridge every day to intern at a startup in DUMBO.
And last fall, I trained to run a marathon, running every day in Central Park. In November, I crossed the finish line in Cape Cod.

You’re probably thinking, “that’s one long bio.” In reality, the more in common you two have there, the more they’re willing to read.

Let’s break this bio down. The person I emailed 1) lives in New York and was on the former mayor’s communications & marketing team, 2) worked on Hillary’s campaign, 3) had tagged WWDC on her Instagram, 4) is at Citi Bike right now working on alternative transit, and 5) is a runner.

Five things in common from five websites, all in chronological order. This makes the email flow, progressing from the past to the present.

The flattery and the ask

After making the connection between the founder and yourself, now is the point to make the connection between you and the company they founded/run.

Showing why you love their company so much is the perfect stage to deliver your ask. This section is short, but it is impactful. Before getting into why this is so successful, let’s look at an example:

Your work and mindset, frankly, inspire me. As a co-founder of a startup and an aspiring designer, I look up to you, your past work, and [company name].
Your platform has changed the way people communicate, but in a way none has before: it’s done so with design.
Now, I want to help [company name] inspire more people by joining your interaction team. With my background being intertwined with the word design, itself, I’m positive that I can truly help make a difference. I know both sides of the coin, the engineering, and the design side, and I hope to bring that with me.

In three short paragraphs, I explain why I think the CEO is so special, why I think their company is so special, and why I’m emailing in the first place.

This works because, in the first paragraph, the flattery makes the recipient excited. In the second, the CEO sees a true understanding of their company. And by the third, the quick acceleration has brought the reader to the ask in a good mood, allowing them to absorb why it was worth getting to the point of this email and what separates the writer from the average.

As you might’ve noticed in this email, and this Medium post, paragraphs are kept to two or three sentences max.

The shorter paragraphs make the email feel shorter as a whole. Instead of endless scrolling, the reader feels as if they are making progress after each paragraph ends.

Longer paragraphs also lead to skimming, and somewhere in the middle sentences, the reader loses focus.

Finally, as most CEO’s read their email on a mobile device, long paragraphs look long, and short paragraphs look normal.

The conclusion

Just how the email accelerated to its apex quickly, it needs to decelerate quickly as well. Once the reader knows the point of your email, they don’t care much about the rest. So in the conclusion, you need to wrap up and get out.

I’d be thrilled to hear your thoughts and would love to continue this conversation. My resume is attached and reference letters are included in it. My portfolio is just my website, so that’s linked as well. Let me know what you think.

This sums up everything you need, you can even copy and paste. The reason this works is that it continues the positive attitude and excitement while offering further reading, like a resume or portfolio.

The signature

Similar to when talking about the first line, many options are available to sign off with.

“All the best,” “best,” “thanks a ton,” “thanks,” “cheers,” “sincerely,” and a simple dash are some examples.

Full disclosure, I use “cheers,” but Business Insider recommends “thanks.” Look at their do’s and don’ts for this one.

Just like five links were recommended in research, five links are recommended for the signature. After testing as few as one link to as many as six, I’ve found it’s a in perfect balance. You should add your:

  • Website/portfolio/Github
  • Resume
  • LinkedIn
  • Email
  • Phone number

Formatting tip: put a space between the first three and the last two, in order to separate your personal links from contact info.

The send button (don’t press it yet!)

One last thing: before pressing the send button, you need to prepare the war room.

If you send an email without a tracker or the right analytics, your odds of getting a response go down significantly. So, in my next post, I’ll cover how to ensure a response by seeing when they read your email, what they click, and how that can inform what your follow up should look like.

If you liked this post, hold down that ? icon (you can go up to 50, you know). Stay tuned for the next post and the one after that, which will go into tracking the progress of your email.

Follow my Medium to learn more about design from a new perspective, literally. For the next few months, I’m diving into how design will intersect with the future. On this page, you’ll see case studies looking into self-driving cars and posts highlighting interfaces that are breaking boundaries in the world of UI/UX.

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