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A Lesson In Email Introductions From Facebook's Mark Zuckerberg

Updated: Sep 25

By Neil St. Clair

This article was originally published on Forbes.com (July 14, 2014)


It was March 21, 2005, and I was a sophomore at Boston University. I had been on this new social networking site called "The Facebook" for a little more than a year-and-a-half (user #900,000 and some change), and was growing increasingly intrigued.


Facebook itself had only launched in February of 2004 and was gaining traction among the college set with user figures somewhere between the 1 and 5.5 million mark--about .25% of its nearly 1.5 billion users today. Well, somehow, I got it in my head that as a journalism major with no experience I would be an amazing communications director/media coordinator for this upstart startup. This was still a time when Facebook founder Mark Zuckerberg had a "friendable" profile and could be reached by a standard Facebook message. Below is my note to the man who would be worth more than $30 billion by the next decade:

Emails must embody a sense of Intrigue, provide Value, and make a clear call to Action in order to be successful.

Looking back, I certainly don't blame Mark for not responding to me.  While I do applaud my efforts to reach him through his startup's native messenger app, everything about the note is wrong. From the subject line: "Proposal"; to the lack of information (though I will give a self-congratulatory pat on the back for my brevity); to my not knowing he was the founder; to my modicum of arrogance about helping him grow his revenue (Facebook closed a more than $12m funding round two months later and now has a $246bn+ market cap).


Had my note been a bit better, and had the Facebook founder deigned it fit to send me a reply, who knows what paths I might have taken, but there will be no crying over my lost hypothetical billions today. Rather, I'm hoping we can use my "epic fail" of email introductions as a teachable moment--one that helped me develop a new set of effective email writing principles.


The Zuckerberg affair is only the start of my email writing journey. The principles I've developed were drafted from a subsequent decades-worth of email writing and receiving--everything from job asks, to requesting an introduction to a billionaire, to raising money for startups. But where I gained the most knowledge was in sending out "cold" invitations to a private dining society I run in New York for entrepreneurs and innovators. Over dozens of events, I've A/B tested just about every subject line and body copy you can imagine, and I've come to one unequivocal conclusion: Emails must embody a sense of Intrigue, provide obvious Value to both parties, and make a clear call to Action in order to be successful. Using this formula, my Society was able to bring people around our table that I had no business emailing in the first place, and, as a result, we formed some of the most outstanding experiences and relationships for our group.


The Planning Phase 

Before you even put digits to keyboard you need to have a plan. Assuming a) That you've identified the person you want to contact (and it should only be one or two targeted people at most, not the whole company) and b) That you have a valid reason for contacting them, you need to decide on your medium. Will an email work? A tweet? A LinkedIn message? Each circumstance cries out for a particular type of outreach, and each media has its own rules of etiquette. But, generally, I still believe email is the most effective electronic means of reaching somebody directly to encourage a timely business response.


(There's perhaps a special case to be made for connecting on LinkedIn as a means of gaining access to details and contact information and creating pre-email familiarity, but that's another topic for another day. However, I would suggest checking LinkedIn to see if you have any common allies who can perhaps make a "warm" intro on your behalf.)

Beyond your medium, you need to realize several things:


  1. Not everyone checks all their email accounts all the time. Find which email account is most material to them and use that one to communicate. Blasting to all accounts is a sure-fire way to get ignored.

  2. Send from a business or non-personal email address when you can. I'm typically less likely to believe an email's validity if it's sent from @hotmail.com. And avoid HTML or email "send bots" like MailChimp for these more personalized business communications. Write in simple, old plain text.

  3. Most people tend to check their emails at specific times of the day--usually on early weekday mornings for busier executives. Sending between 6 and 9 a.m. local time gives you a better chance of being seen "top of inbox."

Beyond these "logistical" concerns, it's important to ensure you keep it brief, state your purpose upfront (and make sure the ask is small), and have a desired outcome/goal and action item in mind (usually one that can occur within a relatively short timeline). Having a clear goal in mind will help you orient your writing from something rambling to something material while having a bite-sized ask will ensure that your recipient doesn't feel overburdened.


Finally, be bold and direct in your outreach. Email the person you want directly (and there's a whole other lesson in how to find their email), no matter how high up the proverbial corporate ladder. You'd be surprised who responds to their own emails, and how generally receptive most folks are to a well-written note.


The Subject Line

It all starts with the subject line. This is the first thing people see, and sometimes the only thing they'll see on a mobile device. Oddly, in some scenarios leaving the subject blank can offer enough "intrigue" to promote an open. You'll notice that a lot of political organizations do this in their weekly calls to action. However, I still believe in offering a simple headline that states your purpose in 100 characters or less (60 or less is even better) and introduces your potential value proposition to the other party--do NOT make it sound like a sales pitch, be genuine and straightforward.


In my note to Mark, a subject line such as "Hoping to Learn More About Facebook," is likely too vague. "Proposition to Help Facebook" is similarly vague, but also a bit arrogant and sales pitchy. Rather, I likely would have gone with something such as, "Looking to Buy You Coffee & Shake Hands." It's got the right amount of intrigue and cheekiness that would play well in this dynamic between two men both in their early 20s. It indicates that the body is going to be some type of request for a business meeting (Action). And what college-aged student doesn't need more coffee (Value)?


In my now near-30-year-old world, this introduction is probably a bit too informal, but the tenants stand the test of time: Intrigue, Value, and Action (IVA). The idea of I-V-A also applies to the body of the email itself, but with added layers of complexity as we'll discuss shortly. But whether in subject or body these principles must be applied with a balancing test--too much or too little of the I-V-A elements and you will fail.


INTRIGUE: Simply sending something that says "Intro" has too little intrigue to warrant attention; whereas no subject at all may have too much mystery in today's cybersecurity-conscious world.


VALUE: I need to understand why I should take my time (on which I clearly place value) to open this email. In my email to Mark, my hope is that he values coffee and getting to know another human being. Overstating your value can come across as too arrogant: "Top Sales Executive Looking to Discuss Ideas" is likely to smack your recipient the wrong way. Conversely, a too gentle approach: "Hoping for a Minute of Your Time" feels passive and creates a sense of burden on the part of the recipient--namely, that you're looking for help.


ACTION: I tend to ignore emails that have no call to action, but I'm very likely to open an invitation to an event or something interesting. However, emails that channel down the path of clickbait, "We found these three problems with your site" or that are too sales-y "Are you looking for more leads?" automatically go in the trash.


Important to note here is that if you've received an intro through a trusted referral, you'll want to state that in the subject. I tend to like to send "warm" intro emails with subject lines such as "Intro from Joe Smith. RE: XYZ Subject."There's a great article on the "send/receive" aspect of referral emails from Chris Fralic, a Partner at First Round Capital that's worth a read here.


The Body

Ninety Percent of the battle is typically just getting your busy recipient to open your email. If you've done that, you've done enough to likely get them to at least read your first paragraph and see if a response is warranted. When it comes to these intro emails (and especially with so many folks checking their email on mobile apps these days), it behooves you to be as succinct as possible while still getting your point across. Two hundred and fifty words (three-four paragraphs) is the cap for something like this--remember, you're not going to close on a first email, your goal is to get the next step--a meeting.


Depending on the person's position, age and what you know about them, the formality of the letter can vary. I tend to prefer using first names as it creates an immediate sense of familiarity and an even playing field, but again certain titles and honorifics might need to apply.


INTRIGUE:: My first paragraph is usually just a single line stating why I'm emailing them.


VALUE 1: My next paragraph is always a simple introduction to who I am (or the organization I'm representing) and why I'm sending the email--ensuring to keep it in the context of my subject line--nothing worse than an email that doesn't deliver what it promised. This paragraph will also include any relevant information about the person or company I'm contacting to show that I'm serious. In Mark's case, we were essentially the same age and both born on May 14th. I was also an early adopter of Facebook and went to his ex-girlfriend's school. Relevant points that may have shown I was worth five minutes.


VALUE 2: The next middle paragraph provides a bit more detail on why my email (and the specific action I'm requesting) is worth their time. What's in it for them? Maybe it's the event itself and the people that will be there, maybe it's the ideas you'd like to share, or perhaps it's simply the value of your company--don't underestimate the human desire to connect or mentor, we are social and egotistical creatures after all.


ACTION: The closing paragraph provides the ask. It may also offer suggestions as to a time/place for the meeting or the specific details of an event.

As for a salutation, I tend to prefer to again be a bit more personal and opt for "Best" and then sign with my initial "N." If an email relationship strikes up over time, this initial-only "sign off" adds a bit of personal brand to my e-missive.


Optionally, below this last paragraph, you might include links to your work if your goal is to engage the individual in a review of material. I also typically add some type of email footer that includes my full name, title, and all relevant contact information.  In certain cases, where compliance is necessary, I may add some type of small-print disclosure.

Again, if you're receiving the email as part of a "warm" introduction the rules are a bit different. It typically behooves you to reply first after the introduction is made, and move the introducer to BCC (common courtesy after all). This shows you have an eagerness to engage and a respect for others.


As a general rule, I tend to like to take out as much filler content as possible--no "Hope you are well." Remember, your goal is to Intrigue them (hence the brevity), provide a clear Value to your outreach, and provide details on an Action to which they can follow up. Above all, be respectful, it's likely you need them more than they need you. As such, I would not offer up any ideas in the email that are critical. Every day I get bombarded with sales pitches that tell me how I could be doing things better. That puts me on my heels, and doesn't necessarily make me hit the reply button any faster. I get 300-400 emails a day or more, and I only give myself an hour to source through them and maybe open/read 30-40 and reply to 10-15. Telling me what I'm doing wrong is the wrong way to beat those odds. Asking for a chance to meet in person to share ideas, or inviting me to a genuinely good event gets me to take notice.


An Example 

Here's how I would have re-written my email to Mark applying the lessons and standards above:


SUBJECT: Looking to Buy You Coffee & Shake Hands


Mark,

I'd love to sit down with you over coffee and discuss Facebook. 


My name's Neil St. Clair, and I'm a sophomore studying journalism at Boston University. I've been a Facebook user since June of 2004, and have been massively impressed with its meteoric growth. Everyone I know at BU is on it, and I think it has a lot to do with the unique design approach you took versus other social networking competitors (e.g. MySpace).

From what I gather people of my generation are your target audience, and I have a few ideas that I'd enjoy sharing with you. Most of them revolve around using Facebook to serve as a platform for news outlets to more effectively engage the next generation of media consumers while creating a monetary stream for your company.


I'll be in Harvard Square tomorrow all day, and wondering if you're free at 11 a.m. to meet at  Starbucks on JFK St. near Lehman Hall. Looking forward to connecting.


Best,

N


P.S. I'm always intrigued to meet a fellow Taurus and saw on your Facebook that we share a May 14th birthday


Neil St. Clair

Boston University Journalism Student


Phone | Email | Address or Website 


From what little we know now of the iconoclastic and idiosyncratic Facebook founder this may or may not have found favor with him, but I wager that for most it provides enough Intrigue, and a small enough ask with clear Value and direct Action to warrant a response. But do note that you'll want to write for your audience and adjust your tone/language to what you think will be most likely to get them to respond while being careful to avoid being both too generic and too cheeky. While you do want to be memorable, sending an intro email that's a funny animated GIF isn't a great way to make a first impression, broadly speaking.


A Few Final Thoughts

Silly as it may sound, when composing your email, make sure you break your paragraphs up properly. Do not bunch them together or make a new paragraph with each sentence--it's optically overbearing. Similarly, put any hyperlinks into text rather than just leaving them raw.

Sometimes bolding certain key points or underling/italicizing can make sense, but don't overuse. Make sure, however, that you're using proper English and that all your words are spelled correctly--notice in my original note I sent to Mark I misspelled "interesting," which is pretty unforgivable. Use the same font throughout and make it a standard, easy-to-read, sans-serif of moderate size. And avoid graphic attachments in your footer if you can.


Above all, be patient. Your recipient may take a while to respond, if they respond at all. Sending a thousand follow ups is inappropriate. Wait a week, and drop another line to check in. Wait one more week and send a final follow up (average vacation is about two weeks, maybe that's to account for the lack of response?), and after that if you don't get a reply, drop it. You may also want to try Chris Fralic's technique of the "presumptive negative" and follow up by saying "I assume this wasn't a fit since I didn't hear back from you..."


Importantly, if your recipient does reply, be sure to respond in a timely manner. Most windows of opportunity close quickly. And if they're a warm referral, be sure and thank your introducer and let them know what the next steps are--it's just polite.


While there's no magic wand that can guarantee 100% open rates and extensive, active follow up, the techniques laid out here (intrigue, value, action) are the best ways that I've found to increase your chances for serious email-based engagement. And, who knows, maybe it will land you the billion-dollar opportunity of a lifetime.


***

Neil St. Clair is a respected social entrepreneur, journalist, and philanthropist. He is currently CEO & Founder of social change consultancy, NES Impact as well as fear-focused venture studio, Notimor. An advocate for children and gender equity, he founded and chairs The NextMen Foundation. Follow him on IG @neilstclair

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N.B. Regarding certain quotations used on this site: I recognize the modern controversy following some of the quoted figures. I further recognize the potentially harmful beliefs these figures held in their time. In quoting them, it is not my intention to glorify or demonize. Rather, I cite their discrete thoughts, which represent a moment of interesting thinking, as separate from their total biography.

© Neil St. Clair, 2020-2025

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