Cartoon drawing of a blond woman wearing a pink apron, standing just outside the door, smiling with a freshly baked apple pie in hand, which she is presenting to the brown-haired man who opened the door.

Cold outreach is the worst. And cold outreach is the best. 

It all depends on how you use it. 

On the one hand, it is absolutely to blame for the dozens upon dozens of generic pitches crowding everyone’s inbox (mine too) that roughly amount to: 

“Dear Business Owner, would you like to buy my crap? No, I have not done any research on who you are and what you sell, how dare you expect me to make an effort. I shall expect a wire transfer by this afternoon.” 

(I’m embellishing, but not by much.) 

But on the other hand, cold outreach — done properly — can work miracles of human connection. It can land big-name clients, JV partnerships, mentorships, book deals, media placements, you name it. 

One well-crafted cold email or DM can open doors that would otherwise stay firmly, snootily shut, and change the course of your business forever. 

Except… almost nobody does cold outreach right. And it’s about to get a lot worse, all thanks to canned scripts and AI.

So if you rely on cold outreach to find new opportunities, be it clients, affiliates, media placements, industry connections, etc… brace yourself. Because rest assured, everyone you’re trying to contact is already swimming in the lowest of the low-effort pitches, where someone just copy-pasted a word-for-word script off some $97 prospecting course — or popped their LinkedIn bio into chatGPT and fired it off sight unseen.

And if you follow the path of least resistance and use the same lazy shortcut, you’ll be ignored just like everybody else. 

So how can you do cold outreach properly — in a way that gets responses and creates opportunities for you and your business? That’s what today’s article is all about.

Read on, and you will learn:

  • 2 strategies to increase your odds of success with cold outreach dramatically — before you send a single pitch. (Almost nobody does this, by the way.)
  • The #1 thing your contacts actually want to see in your cold email / DM, and how to incorporate it into your message without fail.
  • A proven cold outreach template that will help you craft an absolutely irresistible pitch that resonates deeply with the person you’re emailing.
  • One underappreciated secret of successful cold outreach that can make all the difference between a pitch that gets buried… VS the one that gets a response.

And more.

Let’s start with the single most critical lesson I have ever learned about cold outreach. And it goes like this:

The most important work happens before you send your cold pitch — or even write a single word. 

Here’s what I mean…


1. Spend 80% of your time qualifying and prioritizing contacts

In the realm of cold outreach, targeting is queen.

WHO you contact and WHY is vastly more important than WHAT you write in your message.

Emailing 100 leads you’ve painstakingly researched and qualified beforehand will always, ALWAYS generate superior results than putting 1,000 random strangers on blast.

And while it’s true that compelling copy can help you get the attention of the right people… 

…it only works if you know who those right people are, and you have an aligned pitch ready for them.

But if you haven’t done the homework? It won’t matter if you’ve crafted the greatest cold email script the world has ever seen — you’re not going to get results.

That’s why 80% of your time and effort should be spent finding and qualifying the absolute perfect-fit candidates for your offer. For example…

  • Pitching to the media? Take your time to find 5 reporters whose “beat” and past work align with the story you want to send them.
  • Need free beta users for your SaaS? Don’t just give out accounts like candy — find 20 people you’d LOVE to have as paying customers someday.
  • Looking for a joint venture partner? Resist pitching the people with the biggest email lists and social media followings, and find smaller partners whose audiences are the perfect fit for you.

Remember: you don’t need everyone. Not even close! Just a handful of the right people can make a massive impact. So be extra selective about who you pitch.


2. Warm up your cold contacts before you pitch

The best cold outreach… is warm outreach.

When your first interaction with somebody begins with a pitch, it’s very difficult to establish trust. Even if you do everything you can to craft a persuasive, authentic pitch, the person you’re emailing might still wonder: 

“Is this legit, or are they simply an internet weirdo?”

How do you overcome this barrier? Spend some time interacting with your contacts before you pitch them:

  • Follow their social media and leave a couple of friendly comments / replies.
  • Read their public-facing work online and tell them how you’ve implemented their advice, or how something they wrote impacted you.
  • Check if you have a mutual connection — if you do, that person might be able to make a warm introduction for you.

That way, by the time you actually pitch something, you’d be able to point to a previous interaction and say, “We chatted on Twitter about XYZ the other day,” — and make your outreach just a few degrees warmer.

It can make all the difference between a pitch that gets a response — and one that gets insta-deleted without reading.


3. Answer the “what’s in it for me?” question

Humans are innately selfish, and the targets of your cold outreach are no exception. No matter who you’re writing to and what you’re asking of them, those people are going to wonder about the same thing…

“What’s in it for me? What do I get if I do this? ‘Cause unless it’s something REALLY nice, I’m not going to bother and just delete this email, forgetting it ever existed.”

That is the question — except I phrased it like the response of a grumpy teenager being asked to do their chores for once. 

(I mean, prospects and grumpy teenagers have a surprising number of things in common, as any entrepreneur with kids would tell you.)

You’ve got to have a clear, compelling answer to the “what’s in it for me” question when you craft your cold outreach campaign. It’s ABSOLUTELY CRITICAL. Because unless you can persuade people that something is in their selfish interests to do… they won’t do it.

Here’s a very easy way to do it.

Think about what you’re pitching to your leads, and ask yourself: “So what?” And then keep asking this question until you hit on a satisfying answer.

E.g. let’s say that you’re an intellectual property attorney pitching a guest webinar to someone with a big audience of graphic designers:

“I want to teach your community about IP protections they can put in their ToS / client contracts.” => (So what?) “So that they can legally defend themselves from plagiarism and effectively take down stolen work when it appears online. Your audience has a real need to protect their work, I have the relevant expertise — let’s collab.”

(Of course, you’d phrase it differently in the actual pitch, I’m just showing you how your thought process might go.)


4. Don’t use a canned script…

…but DO follow a proven cold outreach template.

In my experience, it helps to structure your pitch in the order of questions your recipient is going to have. Imagine them opening your message — their thought process is most likely to go like this, in order…

  • “Why am I seeing this?”
  • “Who are you?”
  • “What’s in it for me?”
  • [top-of-mind objection your contact might have]
  • “OK, what do you want me to do?”


With that in mind, you want to start your email proving you’re not a random internet weirdo; then, spend the bulk of your time and energy showing what your lead will get as a direct result / benefit of your pitch; head off any potential concerns they might have; and end with a very clear, very specific call to action.

Now that I think about it, writing a good cold email / DM is kind of like writing a compelling marketing video!

Here’s a real-life example of a tremendous cold email I’ve found online. Notice how it hits the beats I’ve just described pretty exactly:

Source of the email (without my highlights):


5. Follow up, and do it more than once

Don’t bet the farm on your first pitch. The reality of cold outreach is, your initial message might easily get overlooked. 

(Or it might get read once, filed away for future response, only to be lost in the chaotic machinery of life.)

It happens.

And a strong follow-up game will help ensure that, even if life gets in your contact’s way all at once, your pitch will still have a chance to get noticed.

Here are some tips to help your follow-up messages stand out:

  • For your 1st follow-up, forward your original outreach email to your contact, so it looks like “Fwd: [your original subject line]” (As a general tip — “re:” and “fwd:” subject lines work great in cold outreach, but it’s important not to use them disingenuously)
  • Stagger your follow-up messages so they’re spaced out. E.g. if you reach out on Thursday, have the follow-up go out the following Monday when your contact is likely to check their email.
  • Follow up at least 3-4 times, and then make a note for yourself to circle back to that lead after a few months — they might be ready for your pitch then!

Here’s a graph by Yesware that perfectly captures the importance of follow-up. Sometimes, it can take a staggering 10 emails to get a response from a prospect — don’t give up too early!

Graph by Yesware that charts the correlation between how many ppl respond vs the number of emails you have to send.Source:


Cold outreach isn’t going anywhere — but…

It will only get harder from here. We’re about to get flooded with pitches that look and sound human enough at first glance, but aren’t actually any more relevant or valuable than the hordes of spam polluting the internet every day. If you don’t want your offer to be lumped in with them, then you’ll have to start approaching cold outreach with extra care, extra attention to detail, and extra humanity.

I know it sounds naive in the age of generative AI, automation, and our collective obsession with shortcuts, hacks, and silver bullets — but it’s the only way forward. Because every business is a relationship business, and the human-to-human connection will never grow obsolete.

In fact, it’s about to become more important than ever. And I hope the tips I’ve shared with you today will help you make the most of it.


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