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How to Write a Pitch: The Ultimate Guide for Freelance Writers

by Sean Ogle | Last Updated: June 25, 2021

It always starts the same.

“Dear Editor.”

“Hey Admin.”

“Hi Location Rebel Editor.”

And my personal favorite, “Dear Mr. Sean.”

They always end up in the same place too.

The trash.

Sometimes, if I’m feeling annoyed, I’ll respond to especially egregious pitches in the hopes that a glimmer of awareness will help people realize they need to shape up.

This happened to the guy who pitched about landscaping ideas and the girl who sent a blog topic on how pregnant women can watch their protein intakes.

Unless I hit my head too hard and missed something over the last 5 years, we don’t talk about anything close to those topics here.

My last response looked something like this (sorry, Stella):

bad pitches

If you’ve gotten this far and think this topic doesn’t apply to you.

Think again.

Because it probably does.

Here are some more examples of just how bad these pitches get:

Here’s the harsh truth: you probably suck at sending emails

If terrible pitches were the exception, not the rule, then every popular blogger you know wouldn’t spend time on social media venting about the piles of crap they get in their inboxes every day.

Here’s an example from John Doherty from GetCredo.

He posted this on his Twitter account and went so far as to critique it:

email john

Check out the responses.

You’ll see people like Brennan Dunn from Double Your Freelance Rate and Tim Soulo from Ahrefs commenting about the same thing. Tim’s even written his own post all about this same topic.

This is a common problem.

I know this because I’ve done it myself.

I’m no email guru, but I have sent a lot of bad emails. Especially when I started freelance writing.

And if you asked me 3 years ago if my outreach emails sucked, I would have said ABSOLUTELY NOT thankyouverymuch.

However, the proof was hard to deny. I wasn’t getting much of a response. I wasn’t seeing new clients. And I wasn’t counting all that extra money in my bank account every month.

Something wasn’t working.

And guess what?

It was me. Turns out my emails did suck.

Ouch.

It wasn’t until I admitted that, and then turned red for 15 minutes from the embarrassment of all those terrible emails I’d sent, that I decided to get my act together and work on my emails.

Once I started actively practicing, testing and improving my emails, things started changing.

First, a story about shotguns

In his book, 80/20 Sales and Marketing, Perry Marshall talks about ‘racking the shotgun.’ It’s based on a story from his friend John. Perry tells the story of John, who learned an important life lesson in the middle of a Vegas club one night, in the book, but I’ll give it a quick summary here.

John’s new buddy pulled out a sawed-off shotgun (I’m going to ignore any of the various laws and safety issues this presents for the sake of the story) and loudly snapped it as if he was loading it. Around the club, a few people turned their heads. The rest either didn’t hear the noise or actively chose to avoid it.

John’s buddy told him to pay close attention to the people who noticed the sound. In this case, those were the people who were interested in what he was doing.

Here’s more what Perry Marshal has to say on the topic:

Everything you do in marketing is racking the shotgun. Some people search Google; some don’t. Some people click on your ad; some don’t. Some open the email, some don’t. Some sign up for the webinar, some don’t. It’s all racking the shotgun.

You send one calculated signal that most ignore, but a few to respond to.

It separates the 80 percent from the 20 percent and it’s the fastest way to separate the amateurs from the pros, even in sales & marketing.

The key to this lesson is that you only want to pay attention to the people who are interested in what you’re doing. (In poker, the lesson is the opposite, a pro wants to play with the people who didn’t turn their heads. Hence John’s buddy only wanted to play with the people who didn’t turn their heads).

It’s the same for your email outreach too.

Most people ignore racking the shotgun. Here’s what they do instead:

  1. They reach out to everyone under the sun that has an easily available email address.
  2. They spend 2 minutes typing out that super generic email and click send to everyone on that list.

Out goes 350 generic form emails. By accident and a bit of luck, one lands in the inbox of someone who at that very moment happens to need a writer. And it turns out, behind that terrible email, there’s actually a pretty good portfolio so they get the gig.

All that effort and they have a 0.27% success rate. So 99.97% of the people they reached out to are the ones in the club who didn’t turn their head. They lucked into the one yes.

Soooooo, congrats?

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How to send a cold pitch email (and where you should focus your time)

Now, I’m not here to tell you that you can get 100% positive response rates from your emails. That works for Beyonce. For us mere mortals, we have to settle for say 30% (which is pretty good, incidentally).

But you’d be surprised how easy it is to stand out from the crowd with a bit of effort and understanding how to rack the shotgun.

It feels counterintuitive but stick with me for a minute.

Not a lot of people are willing to try to improve their response rates. Or actually, let me rephrase, they focus on the wrong side of the equation.

They don’t get any responses to their emails. So what do they do?

Send more emails.

Here’s what I want you to do instead.

SEND FEWER EMAILS.

Stop emailing someone out of a blue asking them to do something for you.

Instead, focus on building relationships with a select group of people who are interested in what you are doing instead.

To do this you have to change your approach.

The main goal most emails you send to people should be to introduce yourself and see if they are interested. This is the slow and the not hot and sexy approach.

It’s like chatting with someone in a coffee shop or a beer softball game or a developer’s meetup before deciding if you want to ask them out.

Sure you could walk right up and ask them to marry you. But chances are, you are going to turn people off doing that.

Instead, it’s all about working on a foundation that can move you along to the next step and then if they are interested.

In this post by Growth Ramp on improving email outreach this type of approach is detailed:

I optimize emails only for a reply. Once someone responds back, they are more invested in the relationship. As a result, I make bigger asks as more emails are exchanged between myself and the person I’m emailing.

This is racking the shotgun in action.

5 steps to sending better cold pitches

Here’s what I do (with the occasional tweak). Is it perfect? Nope. Am I always trying to improve? Yup.

My focus is always on the long game, building relationships for the long haul, getting people to feel comfortable with me, and letting them know I’m genuine and invested in helping them.

Step 1: Do your best to niche down

Niche.

I get that this is hard when you’re first starting. You want to take anything and everything out there, just in case.

First, relax for a minute. Second, try as much as you can to get into a niche. Maybe it’s dentists, or graphic designers, or industrial exterminators.

These are the only people you want to start with at first. You’re going to send an intro email to say hello (pre-coffee date, remember) and rack the shotgun.

The people who respond, you take the next step. The people who don’t, you follow up with over the long term because they’re in your niche and they might not be ready to buy until down the road.

We highlight more on how to figure out a writing niche in the B2B writing post.

Step 2: Spend 10-20 minutes researching

Get your timer out and do this if you have to.

Read the site. The about page. The blog posts.

Google the name of the company and see where they pop up in the news.

Google the executives you can find (especially if one happens to be the person who can hire you) and see what you can find.

All of this research will give you a leg up. You can use what you find to turn a very cold email into a slightly warmer one.

You might find you have something in common with the hiring manager, or someone in common, or very specific language they use (that you can use in your email), or a news story that ties in perfectly with what you want to talk about.

What you want to do is avoid that BS ‘oh I love your posts’ junk that most people start their emails with. False flattery will get you nowhere. Having an insightful thought or comment on a post or interview is going to help you get somewhere.

Step 3: Craft your letter of introduction

This is the problem step for most people.

I generally see two types of emails in this area.

  1. The generic boring email with mail merge links and something the author read that was ‘cool’
  2. The 500 word life story email

I don’t want you to take this the wrong way, but these people don’t care about your life, your major, your passions, or how you think how great you are (with rare exceptions see Step 2).

Instead, focus on them. How you can help them make more money, get more clients, increase their click-through rates, promote their tool, anything along those lines.

Last month, I sent out an introduction email to an agency where I did this. I found an interview the CEO did in a local magazine that gave lots of little nuggets of info.

When I sent out my email, I noted I had read about them in that interview and picked out a comment that I (genuinely) found interesting.

I got a response that they did work with freelancers and I’d get added to their list.

This might feel like a failure because I didn’t close the deal.

Nope.

I racked the shotgun and this CEO took the time to respond. He raised his hand that he was interested. Now it’s my job to keep nurturing the relationship over time until he’s ready to say get lost or yes let’s work together.

Step 4: Keep track of your pitches

There are about a million tools you can use to keep track of your pitches.

I use Streak and I think it’s an awesome tool for staying organized right from your inbox.

There are a couple of reasons why I think it’s really important to keep track of these things:

Why does all this actually matter?

Because you have to be marketing all the time. And part of that is sending out emails.

You can draw a direct line between getting better at emails and seeing more success in everything from getting jobs to building real connections.

Step 5: Do it all the time

For the last 6 weeks, I’ve been doing a marketing challenge. Every week, I keep track of every potential client I’ve pitched, job I’ve applied to, past client I’ve followed up with, and letter of introduction I’ve sent out.

I can’t tell you how much easier it is to see what is working and my progress all in one place. My marketing outreach system has gone from sloppy and infrequent (at best) to a repeatable, scalable, system that is now baked in as part of my weekly activities.

And guess what?

In the last few weeks, I’ve gotten contacts from incredible sites, pitches accepted, old clients back in the mix after follow-ups, and (most importantly) a dramatically reduced aversion to pitching.

How to write a pitch: A checklist

Now we’ve covered the fundamentals sending your pitches, but what about the granual details? What should your cold pitches actually include?

Fortunately, we’ve got a checklist for you.

#1. Have you triple-checked your grammar and spelling?

This one should be the most obvious. And yet…

Image: http://blog.hubspot.com/sales/email-pet-peeves
Image: Hubspot

Four thousand(!) people responded to this survey question, and almost half of them responded with poor grammar. So it’s pretty clear, having an email riddled with poor spelling and grammar mistakes is an issue.

But, amazingly, people still do it all the time.

Here’s a recent example:

Hi Sean,

My name is Joe. I’m a huge fan of your blog and have learned a ton reading it. I’ve been thinkgn about niching down into blogwriting, specifically targeting travel agencies.

I’ve been travel blogging for about a year and think I have a good idea of what the market is right now do you think you could give me a couple of tips on how I can start reaching out to travel agencies, this is the part of the process where I am finding myself getting a little bit stuck and unsure about how I should move forward.

Appreciate your help!

Thanks,

Joe

You don’t need to be a spelling and grammar pro to see some of the glaring problems in this email. Do you really think I’m interested in investing a lot of time with Joe?

Now, it’s one thing to be casual with friends and family, I tend to drop my capitalization when I’m emailing with them. But for a potential client, business partner, or influencer? No way.

Ignoring your spelling and grammar automatically makes you look less professional and credible. I know it sounds harsh, and being a poor speller myself I can get a little testy at the “grammar police” but there are people out there who will immediately send your email to the trash if they notice one error.

The way to solve this is simple: re-read your emails before clicking send. Yup, it will take you an extra five minutes, but it’s likely to save you from further embarrassment down the road.

#2. Have you kept your email short and to the point?

If you look back at that pie chart above, you’ll see that while spelling and grammar is the biggest pet peeve of most people who get cold emails, there is a very close second: the very long email.

Listen to entrepreneur and investor Guy Kawasaki on this:

Long emails are either unread or, if they are read, they are unanswered … Right now I have 600 read but unanswered emails in my inbox.

In fact, he goes on to say he thinks emails should be no longer than 5 sentences. Period.

You would be shocked to find out how many people routinely send 500 (and longer) word emails to very busy people, clients, and influencers and expect a detailed response.

Yea, unfortunately, that’s not happening.

If I have a choice between responding to a 100 word email and a 500 word email that ask essentially the same question, the 100 word guy will get the response right away. The other one will just have to wait until I have the time or patience to read something that long and sift through what the actual question or comment is.

Remember, people are busy. You’re probably busy too. Save yourself, and the person you’re contacting, time and keep your emails short, as in about 150 words and under. You’re far more likely to have a positive response and move the conversation forward.

#3. Do you have a clear (and concise) point or question?

When it comes to the cold email, live by the Rule of One (I’ve made up this rule, but it’s still important, that’s why I capitalized it). Focus on one thing in the email.

Just One Thing.

That one thing could be getting a potential client to get on the phone with you, it could be telling a blogger you loved their latest post, it could be asking an influencer for a quote to put in your upcoming eBook.

It does not mean:

Nope, nope, nope.

See how it’s very easy to get the One Thing lost in the shuffle when you jam a bunch of other stuff in there too?

While you think it’s harmless to slip in an extra ask or more info about you, it just muddies the conversation, it’s more things for the person on the other end to do or process, and that’s rarely a good thing.

The more information and asks you stuff into your first cold email, the less of a chance there is you will actually see any results.

#4. Did you avoid any touchy subjects or off-color jokes?

Look, I’m about as sarcastic as it comes and loves a good saucy joke, but there is a time and place for that, and it’s not inside a cold email.

In general, when you send out emails you want to be able to walk the line between showcasing a bit of your own personality and still keeping things above board. That means staying away from topics that are touchy subjects and have the ability to offend people.

You never know what someone might find funny or offensive, that’s up to them, not you. So, if you have even an inkling of doubt as to something that might be inching up to that line you don’t want to cross, save it.

If you’ve done a good job with your original cold email, and are able to move to the next stage and develop a relationship then joke around and debate all the topics you like, just don’t lead off on that foot.

It can not only make you look bad, but it can also make the other person uncomfortable, or they could mention your faux pas to some of the other people in their network, suddenly making you someone no one wants to deal with.

When it doubt, leave it out!

#5. Do you make it easy to say yes?

When cold emailing you want to make it as easy as humanly possible for the other person to say yes to you.

What that usually means is doing the heavy lifting before you press send. I’m a huge proponent of research and personalization when it comes to cold email.

Yes, it takes longer. But, in my experience, I get much better results, so I don’t have to send 100 generic lazy emails and hope for one or two responses when I can send 10 well-researched and personalized emails and get two or three responses.

Math!

Here’s an example of a content writing post Liz recently applied to via cold email.  This is a great example of making it very easy for the brand to say yes to giving her the job.

In the job posting, the brand was looking for someone who could hit a specific list of qualifications, and the listing also dropped a little Easter Egg in there to refer to hard cider.

I’ve recreated the email here to remove any information specific about the brand or Liz:

Here’s what she sent:

Subject line: When I drink hard cider, it’s Woodchuck…

Email Body: …but mostly I drink Whiskey. First, on to the job! A little about me:

Links: (Here, she included three links to posts she had written that touched on three specific things they mentioned they wanted from the writer). A post that leverages others for shares. A post that is well researched. A post that explains stuff to others.

Pitch ideas: (Here, I included the titles of three ideas for posts).

Take care,  Liz

You can see in the email she went through their gig listing and had every part of her email speak directly to each of their wants and wishes, step by step.

She also took it a bit further and provided them with three pitches for post ideas, something they hadn’t asked for.

She wanted to make sure that in one quick glance of this email, they found someone who could deliver everything they were asking for, removing much of the back and forth.

Here was the response:

Screenshot 2016-03-09 13.04.11

Success.

Not only did she get a yes pretty quickly, she actually removed the need for a step, the Skype interview, and instead got down to writing.

That highlights the power of making it easy to say yes.

Do the hard work for the person you’re reaching out to. Make it an absolute no-brainer to take the next step with you. From there, closing the deal gets much easier.

#6) But also…. make it easy to say no?

How’s that for contradiction?

One of the biggest mistakes people make with their pitches is not showing respect for the person they are reaching out to.

For all the reasons we’ve already talked about usually it’s all about “what can get out of it” as opposed to “what can I do for them?”

I’ve found one of the best ways to prove you respect the email recipient and their time is to make it easy to say no.

You can do this with 4 simple words:

It’s totally cool if.

Watch this video to see what I mean:

Also, this applies more often to full cold emails, less so in the example above when you’re responding to a request for pitches.

#6. Are you using too many exclamation points and emojis?

I’ve gotten one too many emails where every sentence ends with ! or :D.

Even though using these (especially the emojis) are totally common and acceptable today, your cold email is not a text message.

Unless the Oxford Dictionary has something to say about that…

Image: http://blog.oxforddictionaries.com/2015/11/word-of-the-year-2015-emoji/
Image: Oxford Dictionary

An exclamation point here and there is totally fine to really drive something home. But there is no way you need to put one at the end of every single sentence, or worse, multiple exclamation points.

Just one will suffice, I assure you!

The same can be said about question marks, though I see this to a lesser extent.

You don’t need to end your email with something like this: I can’t wait for you to call me!!!!! When can I expect your call???? I hope we have a chance to chat on the phone 🙂  🙂 🙂

It can not only be a bit of overkill, but to some people I can just seem plain unprofessional, which is not the first impression you want to be making.

Remember, in the vast majority of cases, you have one chance to hit a home run with a cold email, so it’s the very small details that set you apart from everyone else.

Keep your exclamation points and emojis for social media, where they can totally enhance the conversation. 🙂

#7 . Do you have a call to action?

Nope, call to actions aren’t just for sales pages and copywriting. You need them in your emails too, especially your cold emails.

This ties right into the concept of making it easy to say yes. How can you make it as easy as possible for the person you’re emailing to act if you don’t tell them what you want them to do?

Here are a bunch of common calls to action you’ll likely want to use in your emails:

See, pretty simple.

You don’t have to go crazy and channel your inner Gary Halbert, you just want to be able to gently direct the person or brand you’re emailing in the direction towards taking the next step with you.

Don’t leave it up to them to figure out what they have to do to move forward, or what the next steps are, or have three back and forth emails to set a call time.

Take it out of their hands and put it into yours.

#8. Have you made the email all about you?

This one is a biggie.

So many cold emails are all about the person sending them, not about the person receiving them.

This is a classic error that’s usually done with good intentions. Of course, as you do your research before you email, find and call attention to things that can help build a connection, but in your first email keep it brief.

I did that too in the beginning.

When I started in Location Rebel, I jumped into SEO content writing, which involves a lot of cold emails. I figured these companies would want to know all about me before they hired me, right?

So I gave them endless amounts of information, where I grew up, my hobbies (?!), where I went to college, blah blah blah…

As you can imagine, I didn’t get much in the way of responses.

It wasn’t until I learned that I had to approach cold email in a different way, focusing the email on the person (or brand) getting it that made the difference.

Look, it’s natural to want to highlight a bit about yourself, but don’t go over the top. And you should give a little insight into who you are. Afterall, building a little rapport can go a long way.

But you’d be shocked to see the emails we get where the other person writes a 500 word email where 99% of it is about them, followed by a “big ask.”

Don’t make this mistake.

Keep the email about the person you are trying to connect with: how you can help them, solve their problems, get them more readers, get them more attention, highlight how awesome they are, make them more money, etc.

You get the drift.

#9. Did you avoid bulk messaging and spamming?

I know what you’re thinking.

“But, Sean. I work a full-time job and I’m trying to get a gig, so I got a list off of Fiverr with 1,000 companies. I don’t have time to email them all so I sent out 10 bulk emails of 100 companies each, what’s wrong with that?”

Oof.

Yes, I’ve been there, I know it’s a slog sending out tons of cold emails, especially when you’re trying to get that first gig.

That’s why we included this one, even though it’s mostly a rookie error.

At first, it feels like a great way to save time. But it also means you’re not going to get very good results.

Chances are your email is incredibly generic, the same generic email these brands get from the other 1,000 people emailing them on a daily basis, so you don’t stand out.

Does this look familiar?

Dear Manager, 

I am contacting you about my SEO writing services. I provide excellent articles that you will be able to send to your clients. I am a native English speaker and a University graduate. My rate is $20 per 500 word article. I look forward to hearing back from you.

Thanks, 

Sean

Zzzzzzz….oh you’re still reading?

How useless that email is?

You can spot it as a generic, copy and paste job from a mile away. But that’s not the only reason why this is bad, it’s also incredibly easy to make a mistake.

A big mistake like not bcc-ing all the companies, so they can all see that you’ve just sent them a bulk email. That’s happened to more than a few people I know.

Remember, when you send generic bulk messages, you aren’t actually doing yourself any favors.

The vast majority of the time it’s a waste of your time, sure you might get lucky and hit a client or two, but most of the time I see people give up on the bulk and start from the beginning with personalized cold emails.

One Last Thing to Note: FOLLOW UP

Just because you sent off your cold email does not mean your job is done.

Nope, in fact, far from it.

In the case of cold contacting, persistence is your friend.

Let’s face it, people get a lot of emails, they are busy, maybe you sent an awesome email and exactly the wrong time and it got lost in a vast inbox. So what are you supposed to do, call it a day and move on to the next?

Of course not, you follow up. It doesn’t have to be anything crazy (or rude or passive-aggressive) understand that sometimes things get lost in the shuffle, and you’re sending over a gentle reminder about that email.

Here’s what you can use as a quick and easy template:

Hey Sean,   

Sending over a quick follow-up to my email last week about guest posting. I know you’re busy, so I copied the contents of the first email below to save you time searching. Let me know what you think!

Thanks, 

Liz

See, a simple three-sentence follow-up can get the job done.

If after a few days you still hear nothing, follow up again. Remember that old saying “the squeaky wheel gets the grease?”

They were predicting cold emails.

Don’t give up on following up.

There are a couple of tools out there you can use that will help you track emails and remind you of when to follow up. So check out BoomerangStreak, and Followup.cc to help streamline and organize your follow-up approach.

Don’t let me down…seriously

I’m on a one-man mission to help people send better emails.

I promise if you spend time doing these things, researching, and coming up with a solid marketing plan you will see success.

Are you ready to do it?

Did you know that inside Location Rebel Academy we have an entire course completely geared towards helping you send amazing emails that get you the response you’re looking for?

It doesn’t matter if you’re pitching clients, influencers, friends, or anyone else. Our course helps with the psychology behind it, gives dozens of templates for every situation imaginable, and will help you feel confident every time you hit the send button.

Check out Location Rebel Academy and get out full “How to Send a Cold Pitch” course.

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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