Unleash Your Inner Comedian: How to Craft Irresistibly Quirky Cold Emails That Don’t Go Unnoticed

Is your cold emailing approach as exciting as watching paint dry? Does the thought of drafting another yawn-inducing business email make you want to abandon your desk and become a mountain hermit? Fear not! You’re about to discover an innovative and hilariously refreshing tactic to breathe new life into your email marketing. Picture this: cold emailing, but with a generous serving of comedy! In this piece, we’ll dive deep into the world of quirky email marketing, transforming the bland ‘business as usual’ into a fun-filled fiesta that will have your recipients eagerly clicking open. Buckle up, we’re about to add some much-needed LOLs to your inbox!

The Experiment

The digital marketing landscape is crowded, to say the least. With the sheer volume of emails that SEO business owners receive on a daily basis, it’s become increasingly difficult to stand out and capture their attention. In response to this challenge, our team at GetOffTheDamnPhone embarked on an experiment to test the effectiveness of a quirky, humor-infused approach compared to a traditional, professional style in email marketing campaigns.


Our team used GetOffTheDamnPhone’s email finder, a powerful tool for sourcing accurate and relevant email addresses of SEO business owners. The experiment involved two campaigns:

  1. Professional Campaign (Campaign 1): 200 emails were sent out with a polished, business-oriented tone and content.
  2. Quirky/Funny Campaign (Campaign 2): A set of 200 emails were crafted using a humorous and unique tone, adding unexpected flair to the usually standard email pitch.

Both campaigns included follow-up emails for those who did not respond initially.


The results of both campaigns over a three-month period were compelling:

CampaignEmails SentOpen RateResponse RatePositive ResponsesLeads Generated
Professional (Campaign 1)20020%5%105
Quirky/Funny (Campaign 2)20045%25%5025

The quirky/funny campaign (Campaign 2) significantly outperformed the professional campaign (Campaign 1) in terms of open rates, response rates, positive responses, and leads generated. The novel approach led to a more than two-fold increase in email engagement and resulted in five times more leads.

First You Need To Grab Attention & Trust

The Warren Buffet Technique

Warren Buffett is famous for his honest and upfront communication style, especially his habit of delivering bad news first. 

He believes in the principle of tackling the hard truths head-on, which helps build trust and credibility.

In the context of cold emailing, this could mean acknowledging potential objections or challenges at the outset. This shows your prospects that you’re not trying to gloss over the facts or manipulate the truth. Instead, you’re being transparent about the whole picture, even if it isn’t entirely rosy.

Here’s an example of how you could integrate this into a cold email:

Subject: “Facing ABC Challenge? We Did Too!”

Dear [Recipient’s name],

I hope this email finds you well. I’m [Your name] from [Your company], and I wanted to address something that I’m sure you’re no stranger to – the challenge of [insert problem here]. It’s a tough issue that many in our industry face, including ourselves.

[Insert story about how your company faced this issue and how you overcame it.]

[Discuss your product/service and how it can help the recipient solve the same problem.]

Although we’ve seen success, we know that our solution may not work for everyone. Every business is unique, and what worked for us may not necessarily work for you. However, we thought it was worth sharing our experience, as our solution might be the answer you’ve been looking for.

I would love to learn more about your business and see if we can help you overcome the [insert problem here]. Could we schedule a call next week to discuss this further?

Looking forward to hearing from you, [Your Name]

The idea here is to upfrontly address a common challenge in your industry and share how your product/service helped tackle it. By acknowledging that your solution may not be a one-size-fits-all, you’re demonstrating honesty and building credibility. You’re also showcasing empathy and understanding, which can go a long way in establishing a connection with your recipient.

How James Altucher Uses “Damaging Admissions” To Create Trust In His Emails

James Altucher, a renowned entrepreneur, angel investor, author, and podcaster, is well-known for his brutally honest and raw style of writing. One of his powerful strategies is the use of “damaging admissions” in his emails, an approach that he leverages to engage with his readers and establish a strong connection.

A “damaging admission” is essentially sharing a flaw, mistake, or a piece of potentially negative information about oneself or one’s business. It’s a counterintuitive approach to building credibility and trust with the audience. While it might seem risky or even counterproductive, it works on the principle of vulnerability, authenticity, and transparency, all of which are key to building rapport and trust.

In the context of email writing, this could mean sharing a failure story, admitting a mistake, or discussing a challenge or obstacle that you or your business is currently facing. By doing so, you give your audience a peek behind the curtain, humanizing your brand and making it more relatable.

Here’s an example of how you could use a damaging admission in a cold email:

Subject: “The mistake we made and how we fixed it”

Hello [Recipient’s Name],

I hope this email finds you in great spirits. I’m [Your Name] from [Your Company], and I have a confession to make.

We screwed up. Big time.

A few months ago, we launched our new [product/service], confident that we’d nailed it. But soon after, we realized we’d missed the mark. We received feedback from our customers that [insert problem here], and they were right. It was a hard pill to swallow, but we needed that wake-up call.

So, we went back to the drawing board. We spent countless hours addressing the issues, refining our [product/service], and making sure we got it right this time.

Today, I’m thrilled to introduce you to the new and improved [product/service]. We’ve taken our customers’ feedback to heart, and we believe we’ve created something that genuinely solves [insert problem here].

I’d love to share more about our journey and how [product/service] can benefit [Recipient’s Company]. Could we schedule a call next week to discuss this in more detail?

Best, [Your Name]

In this example, you’re openly admitting a mistake your company made with a product or service. Instead of hiding it or glossing over it, you’re addressing it head-on, sharing how you listened to customer feedback, made necessary improvements, and came out with a better product or service. This strategy builds credibility, demonstrates resilience, and highlights your commitment to quality and customer satisfaction.

Now… We Get Quirky

Injecting Humor

Humor is an impactful tool for establishing a human connection with your recipients. It can break down barriers and make your message stand out amid a flood of formal and conventional business communications. For example, your email might start with an unusual greeting such as, “Greetings [Recipient’s Name], You’ve never heard of me. Hi, I’m [Your Name], your new favorite person.”

The Rule Of 3

The “Rule of 3” is a fundamental principle in writing that suggests information or actions are more engaging and memorable when presented in trios. This trifecta has a rhythmic cadence that helps readers process and recall the information more easily.

Applying this concept to the realm of email writing can amp up the effectiveness of your communication. Here’s how you can harness the power of three:

  1. Attention-grabbing Introduction: Start by addressing three crucial issues your reader might be grappling with that your product or service can alleviate.

    Example: “Feeling bogged down by dwindling conversion rates, elusive quality leads, or an under-motivated sales squad?”

  2. Body: In the meat of your email, lay out your primary propositions or arguments in groups of three. This structure keeps your message neat, digestible, and easy to follow.

    Example: “Our revolutionary software has been engineered to skyrocket your conversion rates, reel in top-tier leads, and transform your sales team into unstoppable deal-closing machines.

  3. Call to Action (CTA): If you’re giving your reader multiple CTAs, stop at three. Otherwise, you risk information overload. Ensure each CTA is sharp, snappy, and seductive.

    Example: “Ready to take the leap? You can (1) book a zero-cost consultation with our experts, (2) dive into our success stories through our case studies, or (3) enroll your pet iguana for a free software tutorial – we’re committed to diversity in tech!”

  4. Conclusion: Wrap up your email or your proposal with a summary of three main points. This reinforces these ideas and leaves a lasting imprint in the reader’s mind.

    Example: “To put it in a nutshell, our trailblazing software is your secret weapon to boost conversion rates, magnetize premium leads, and inspire your sales team to break barriers. (P.S. The iguana is optional.)”

By injecting the “Rule of 3” into your emails, you not only add clarity and structure but also a twist of unexpected humor, making your communication more engaging and unforgettable.

Creativity and Storytelling

Rather than beginning your email with a standard pitch, consider spinning a narrative. Storytelling captivates the reader and forms an emotional bond. For example:

“Once upon a time, a harried marketer named [Your Name] chanced upon your company. Amazed by your astounding work, I felt compelled to reach out and see if we might start a tale of corporate synergy.”

Compliments and Flattery

Used genuinely and appropriately, flattery can be potent. Ensure your compliments are specific to the recipient’s work, indicating you’ve done your research. For instance:

“I came across your recent article on [Topic]. Your insights blew me away, especially your perspective on [Specific Point]. It’s clear you know your stuff.”

The Unexpected Ask

This strategy involves an atypical request that makes the recipient pause and engage. For example:

“I’m sure you’re inundated with emails asking for meetings, partnerships, or 15 minutes of your time. I won’t do that. Instead, could you spare 47.3 seconds to ponder how we might revolutionize your business operations?”

Transparency and Honesty

Being straightforward about your intentions can be refreshing for the recipient. For instance:

“This is a cold email. I’m reaching out because I believe [Your Product/Service] could bring immense benefits to your team. Here’s why…”

The Close

Conclude the email on a humorous note to leave the recipient with a smile and a positive impression. For example:

“If you’ve read this far without hitting ‘delete’, thank you. I’m as surprised as you are. If you’d like to continue this wild ride, feel free to reply.”

WARNING – Some People May Get Triggered

While the quirky, humorous approach to email writing can do wonders for your engagement and response rates, it’s not without its share of perils. The realm of humor is a vast one, with people’s sense of what’s funny as diverse as their fingerprints.

Not everyone is going to chuckle at your witty one-liners or appreciate the humorous spin you put on your proposition. In fact, some might even perceive it as unprofessional or flippant. There’s a risk of misunderstanding or even causing offense if your brand of humor doesn’t jive with your reader’s.

Moreover, in certain industries or corporate cultures, a quirky email style may be viewed as inappropriate or out of place. Some situations call for a more buttoned-up, straightforward approach.

But don’t let this deter you. Remember, to make an omelette, you’ve got to break a few eggs. The ones who enjoy your emails are not just going to like them; they’re going to love them. You might ruffle a few feathers along the way, but you’ll also attract those who appreciate your unique style and resonate with your brand’s voice.

This method has the potential to fast-track the “know, like, trust” factor with your audience, fostering strong relationships with the clients who appreciate your distinct flavor. These are the people who are likely to become your loyal customers, your enthusiastic advocates, the ones who truly understand and appreciate your brand’s personality.

So, while it’s essential to be aware of the risks and exercise judgment with the quirky method, don’t shy away from showing your brand’s true colors. Just like baking a cake, it takes a few cracked eggs to create something truly delightful.


Adopting this quirky approach to email marketing not only renders your emails more engaging but also forms a more human connection with the recipient. By integrating humor, creativity, flattery, an unexpected ask, transparency, and a light-hearted closing remark, you transform a standard cold email into an unforgettable and quirky message. It’s about cultivating relationships, not merely closing deals. And that’s a technique worth mastering.

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