My Cold Email “Template”

First of all, I should preface. Though I find templates to be useful when you’re shooting for quantity over quality, I default to only using limited elements of one, if at all, when my goal is quality > quantity. The goal with 90% of my emails I have ever sent is where I’m punching above my weight class, be it –

• Applying to college – writing a letter to the deans of respective schools to get a personal tour,
• Asking for funding – from top-tier VCs and potential long-term partners,
• Asking for advice – from VCs and seasoned founders, in the form of tactical and veteran mentorship,
• Or, exploring perspectives. I’m pretty liberal in my scope here.

If you’re here reading this and are looking for a silver bullet. If you’re looking to be that John Wick walking away from a massive explosion behind you… well, I regret to let you know – I don’t have one. I wish, but I don’t. But to me, that’s what makes this black box of relationship building ever the more fascinating. Had it been easy, I would have gotten bored real fast. Unfortunately, I have a limited mental stamina for things that work because… well, they work.

Inspired and encouraged by my conversations with 4 amazing souls over the past week – a founder, product manager, startup mentor, and my mom, here are the tactics I learned after years of reaching out to folks that inspire me, specifically closing one a week since 6 years ago.

The Subject Line

My email subject lines, fortunately and unfortunately, have the highest variance. So, I can merely share the 2 frameworks I use the most often:

1. Getting straight to the point – Who are you? And what is your CTA (call-to-action)/ask? – In these situations, limit the number of words ideally to 5-7 words. – For people who have straightforward, “no beating around the bush” personalities.

2. Cite a quote they recently said – We all have some level of ego. And this method feeds into it a little. – This method, on the other hand, can get gimmicky/clickbait-y really fast, if the contents of your email is irrelevant to the subject line. – A close cousin is using a quote they personally love. – For people you want advice from and have more curious personalities.

The Content

I leave the greeting of an email (i.e. Dear…, Hi…, or Hey…) pretty open-ended, as long as it reflects a similar tone as the rest of the email. For example, don’t start with “Dear” whereas the rest of the email has a whimsical tone.

The order of the following is something I play around with, but my emails usually cover a majority, if not all, of these areas:

• Introduction
• Why them?
• Showing understanding (and the opt-out)
• Doing your homework
• Call-to-action (CTA)
• Personality
• Signing off

And of course, each with varying length, depending on who I’m reaching out to and what their bandwidth for new content and priorities look like.

Introduction

Simple, easy. To the point. Who are you? And, what do you do? Your first impression, or second impression, if you count the subject line. Build up social capital with the person you’re reaching out to. Why should they care?

To play my own devil’s advocate, I either go all in on ‘seriousness’ or not at all. As famous philosopher, Ron Swanson, once said:

“Never half-ass two things; whole ass one thing.”

For instance, I once reached out to a brilliant reputable artist with:

“I’m David. You’re David. You like to paint. I like to doodle.”

Again, consider your audience.

Why them?

Everyone’s special. But even if they think (think being the keyword) they aren’t, they still want to feel that way. There are 2 ways I approach this:

1. If they’re not extremely well-known, but may be popular in their niche vertical…
   • Where/how did I find them?
   • Did I do further research on them?
   • What is one thing they said/did that stood out to me?
2. If they’re a household name…
   • I better have a damn good reason, other than ‘rubbing shoulders’.
   • What is their track record in life/career look like? Are there parallels to what I’m seeking?
   • What are the inflection points in their life I’m curious about? Am I at a similar inflection point now?
   • In VC vernacular, “why would they be the best dollar on the cap table?” The more similarities between how they overcame a previous circumstance and the circumstance I am in now, the better. I might be seeking different outcomes, but that leaves room for discussion.

Showing understanding (and the opt-out)

“I know you get a hundred emails a day, and if you don’t have any time to respond, I completely understand. But if this makes it through your inbox, I can’t describe how much your reply would make my week. I couldn’t think of a better person to reach out to.” [insert research]

So what are the signals of what I just said?

• “I know you get a hundred emails a day…” – I acknowledge that they’re busy people. Let them know I understand their daily pain points. Feel free to tweak the number as you see fit for the individual you’re reaching out to.
• “… and if you don’t have any time to respond, I completely understand. But if this makes it through your inbox, I can’t describe how much your reply would make my week.” – The opt-out. Give them room to retreat.
  1. It reduces the level of social pressure for them to respond.
  2. If they do do you a favor and reply, you preemptively showing your gratitude and its magnitude.
• “…I couldn’t think of a better person to reach out to. [insert research]” Before I even dive into “why them?”, I preface what they’re about to read. A signaling of #spoileralert – spoilers of me describing how awesome they are.
  1. I show them this is not a ‘copy pasta’ email. I’ve done the legwork. And I am very purposeful as to why I’m reaching out.
  2. Well, it makes harder to turn down, or ghost, the email once they open it. It’s still possible they would, but I’m just trying to lessen that probability.

Often times, I employ a mix of my 2 frameworks here.

Doing your homework

So, I did my homework on them. Now… so what? Why should they care?

The mental model I use is:

“One thing I’m really struggling with is _____, and I know you went through a similar situation. Here’s what I’ve tried so far…”

The more they can relate/have context to what I’m going through and how they might fit in this puzzle, the better.

Call-to-action (CTA)

Keep it simple. My 2 most used CTAs are:

1. One specific question that only this individual can answer.
   • I also complement my question with: “If it’s easier, here’s my cell (XXX)XXX-XXXX.” To give them multiple options where they can choose which is the most convenient for them.
   • On occasion, if the individual is extremely busy (possibly within the time frame in which I reach out in) with other priorities, I ask: “If your time is limited, could you point me in the right direction? What resources and literature should I look into, or people should I talk to?”
2. A 20-minute call
   • 20 minutes, because it’s long enough to ask at least 2 questions, but doesn’t carry the stigma of the overused 30-minute ‘coffee chat’. So less mental commitment, and less anxiety before jumping on the call.
   • Part of the reason why I think The Twenty Minute VC podcast by Harry Stebbings is so successful.

Personality

Ideally embedded throughout the email. Be yourself. Have fun!

Putting on a facade of professionalism, at least for me, only makes my future interactions with people more draining. For the sake of ‘protecting’ my reputation, I end up building anxiety which stresses me out.

A more esoteric method, possibly controversial, I learned from a world-class salesman many years back is to use memes or GIFs. It stands out. And frankly, pictures speak a thousand words (if used aptly). And yes, it’s helped me start conversations with Fortune 500 CEOs, VCs, and our friends in Hollywood. One senior executive who worked at a household name shared that she loved it and picked up this habit for herself.

Signing off

Admittedly, this is another section I have a lot of fun in. It happens to be another segment of the letter format that is often overlooked for its redundancy, like the greeting. But unlike the greeting, by the time the individual I’m reaching out to reaches here, they’d already have committed to the entirety of my email. At this point, they have a relatively good grasp as to what kind of person I am.

So being a bit more creative in your email signature does you no harm. Maybe even get you some brownie points. For instance, I have signed off with “Cheerios and orange juice,” and “Hunting for phoenix feathers,“. Usually with a closing that has a metaphorical bond with the content of the email.

I also never sign off with my full name. Just David, or D. Since my goal is to be more personable. And hopefully gain another friend in the process.

Once in a while, if I find something pertinent to the individual, but irrelevant to the content of the email, I add in a postscript.

“P.S. I noticed you’re in the market for the best fried chicken and waffles recipe. I highly recommend [insert restaurant].”

And, if you’ve made relationship building a habit…

“… If you tell them I sent you, they’ll give you a cooking lesson on the house.”

In closing

I don’t have a cure-all elixir, and trust me, if I had one, I would share it. After all, my goal is to make my current self obsolete. If I can actualize the world around me to motivate me more to improve, I will. For instance, this blog is a record of that. But I digress.

I hope my years of honing my craft may prove to be useful to you in some meaningful way. If you’re interested in the mental models I use to approach reaching out to the passionately curious and the curiously passionate:

• How I “pre-game” cold emails. Why do I play the long game? When do I choose warm intro over cold email, and vice versa? Above all, who are the stakeholders in the relationship ecosystem?
• The elephant in the room for cold emails. Answering “why are you reaching out to me?” and “how long will this interaction take?”
• My contrarian beliefs for the ‘optimal’ length of an email. What are the parameters I consider when deciding length?

Photo by Nathan Dumlao on Unsplash

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