My Cold Pitch That Hooked A VIP Client (Plus Two That Flopped)

cold email pitches freelance writer

By Dominic Vaiana, Freelance Writer


Two Types of People

Psychologist Adam Grant distinguishes between two types of people that climb the success ladder in vastly different ways: Givers and Takers.

Takers, Grant explains, squeeze as much value as they can out of others by force – they’re out for themselves. Givers, on the other hand, are in tune with the needs of others – they’re empathetic and emphasize solutions over self-interest.

It might seem that sending cold emails to earn freelance work is a Taker’s game. You’re cajoling strangers into paying you to write for them. You’re selling yourself for a paycheck.

However, I’ve learned that cold emailing doesn’t have to be as ugly as some writers make it out to be. It’s possible for freelancers to thrill people with a cold email.

Allow me to explain.

Bring Something To The Table

Adam Grant says Givers tend to have more long-term success than Takers in the workplace. I’ve recently taken this insight and run with it. After graduating school with virtually zero connections, I knew I had to embrace cold emailing at some point. If I didn’t, I’d cut myself off from a world of potential clients.

It’s easy to bash cold emails that use copy-and-paste messages such as “Can you please refer me to your marketing director?”


However, if you use your pitch as an opportunity to make a compelling offer as opposed to a vague request, your pitching game will do a 180. The purpose of your cold email is to bring something to the table, not ask for an invitation to the table.

As I write this article (which entailed a pitch to Find a Way Media), I’m reflecting on the fact that I’ve sent more pitches than I can keep track of. Few have panned out. But through a slow, tedious process, I’ve taught myself to think like a Giver rather than a Taker and earn responses that have turned into paying work. Let’s dissect a few examples.

My pitches that were (apparently) bad enough to warrant no response

Cold emails are a necessary tool for many freelancers to generate leads and make connections. But without the proper framework, all they do is familiarize you with being ghosted by would-be prospects. Hopefully, this section will spare you the time and energy I wasted on cold emails that yielded even colder no-replies.

Exhibit A:

cold email flop exhibit a

While this email is polite (thanks for teaching me manners, Mom) and relatively brief, there are five big problems:

  1. The subject line is more boring than watching paint dry (the blanked out part is the brand’s name.) How I ever thought that would cut through the clutter is beyond me.

  2. There’s no recognition of the brand, what they’ve accomplished, or how my skills relate to their mission.

  3. “A friend of mine…” – What friend? For all she knows, I could’ve just made that up.

  4. “I’d love to contribute.” – Contribute what? Blog posts? Elvis impersonations? Cooking lessons?

  5. “I’ve written X, Y, and Z” – No examples? That’s a big no-no. Nobody has time to scour the web for writing samples, especially for a stranger.

Exhibit B:

cold email flop exhibit b

While this email is better in some respects (mentioning a connection, including writing samples) than the previous, it has its own flaws. Here are my hot takes on why it flopped:

  1. The subject line is about me rather than the recipient. It’s a plea for help (building my freelance client base) when it should’ve been an offer. Think: Givers vs. Takers.

  2. The message creates work for the recipient – determining if she has a need for more writers. Instead, I should have bypassed that issue with something like, “I’m not sure what your staffing situation is, but I can offer you X, Y, and Z starting next week.”

  3. What’s in it for her? (Besides having to cut a paycheck and figure out how, if at all, I’d fit into her network.) That’s not too appealing. Could I have helped her find more clients? Offer a new perspective on writing projects? Maybe. But I didn’t mention it.

These two analyses might seem picky, but cold pitching is a meticulous art that demands constant fine-tuning. Without a healthy dose of self-criticism, teaching yourself how to send pitches that actually make people care can be as frustrating as it is futile.

Read how to write jargon-free sales emails.

The Cold Email That Scored A Meeting With A Successful Startup

Sifting through your sent email folder to figure out why your pitches aren’t being answered (like I did to research this article) is deflating. But the joy of one successful pitch will erase the misery of all the unsuccessful ones.

Here’s a cold freelance writing pitch that piqued the curiosity of a globally-recognized entrepreneur:

cold email success

After a brief exchange about a logistical question, he came back with:

Screen Shot 2019-03-29 at 3.11.52 PM.png

Why would a prominent entrepreneur want to schedule a meeting with a recent grad, much less a total stranger?

To answer this question, we need to go back to Adam Grant: This entrepreneur is busy, he’s probably stressed, and he’s accountable to dozens of employees and shareholders. Does he want to explain what open positions may or may not be available? No. Does he have time to wonder what I might bring to the table? No. He needs to get s*** done. And that’s why the Giver approach almost always triumphs over the Taker.

  1. The subject line kills two birds with one stone. It acknowledges that I put in the time to research his company and makes an offer

  2. I identified a pain point: an inactive blog

  3. I offered a solution, supplementing it with the idea that his audience would enjoy them.

  4. I offered tangible examples of what that content would look like.

  5. I included social proof by mentioning my work with other tech brands like GoDaddy and Mastercard.

As I mentioned earlier, there is no cut-and-dry formula for cold email pitching yourself as a freelance writer. Each email is its own unique entity that requires research and tinkering. But that doesn’t diminish the importance of a guiding framework (giving instead of taking). Not every offer will earn you a meeting, much less a job. But at least you’re heading in the right direction.

Final Thoughts

Most of us (freelancers or otherwise) live in a silo of our own imaginations, thoughts, and desires – we assume that people are selfless when, in reality, they’re in the same boat as us. They need help, just different kinds of help. We need an opportunity, they need an article written, a fresh idea, a story to reference, and so on. It’s our job to create symmetry between their needs and ours.

Of course, most people don’t realize this (or refuse to acknowledge it), which leads to Taker questions like:

Do you have any open positions for freelance writers?

Can we set up a call to talk about content marketing?

Can I have a gig with your company?

Contrast those questions with Giver questions:

I thought this idea would resonate with your audience – can I write about it?

What content marketing work can I take off your plate?

Can I start a blog for your brand?

As the author Robert Greene notes in his book The 48 Laws of Power, “There is an art to asking for help, an art that depends on your ability to understand the person you are dealing with and to not confuse your needs with theirs … if you make no appeal to [someone’s] self-interest, [they] merely see you as desperate or, at best, a waste of time.”

Cold email cliff notes

  • Your subject line is your key to entry. Use it to make or imply an offer.

  • Don't copy and paste your emails. Personalize them. Do your research and leave no doubt that you did your homework.

  • Don't be vague. Give specific examples of what you’ve done and what you can bring to the table.

  • Don't assume your recipient cares about you. Your job is to make him or her care.

  • Ask questions: Do you think your readers would enjoy X article? Can I do Y for you? People are more inclined to respond to questions than assertions.

  • Be a human being, not a salesperson. Don’t be afraid to tone down the professional language – a conversational email can be a breath of fresh air. The people you pitch are humans before they’re decision makers, and reminding them of that is a sure-fire way to stand out in their inbox

Black and White

Dominic Vaiana, Writer, Marketer, Strategist

Dominic Vaiana is a writer, bibliophile, and oxford comma enthusiast. You can find his articles and book recommendations at