How to Cold Pitch Like a Pro with Joe Dyton

This post may contain affiliate links.

Every Friday I host (and record) a live Blab with a fellow freelancer. For those of you who can’t catch it live, want a review or just prefer reading a blog post to watching a video, here’s a recap of my recent chat with Joe Dyton, a 30 Days or Less to Freelance Writing Success alum.  

After completing 30DOL in the summer of 2015, Joe wasted no time in perfecting his cold pitching approach. He’s been in the freelance game for three years, all the while working a full time job in Washington D.C.

Joe joined me on last week’s Blab to share his tips on how to cold pitch like a pro. Here are the highlights of our chat.

What’s the balance between using job boards and cold pitching for you, Joe?

I’d say it’s about 50/50. If I am feeling a bit lazy and I want to pitch, I’ll go right to the job boards. But I know that’s competitive, and everyone is pitching to those jobs.

That’s why I’ve turned to cold pitching.

Are you marketing in any other way right now?

I do cold calls.

Emails can get lost, deleted, or prospects don’t check them right away. Sometimes it’s easier to get somebody on the phone if you’re calling their line directly. At the very least, you’ll talk to them for a few seconds.

I also found out that some people don’t use email that much when I had to reach out to some sources recently. Some people are old-school, so it’s good to try and mix it up.

Have you landed any clients through cold calling?

Yes, I landed my most recent client that way. It’s a content marketing agency.

I Googled “content marketing agencies in Chicago.” I wrote down 5-6 numbers. Then I made a few phone calls and got to one.

I left a message, the owner of the agency got back to me, and I turned in an article for them this past week.

Are you cold calling businesses as well, not just content marketing agencies?

I sometimes do that too.

I ask to speak with the Head of Marketing, Communication or PR. Those are the departments that probably need writers.

Do you get through to those people without knowing their names?

It varies.

Sometimes you can’t get through when they think it’s a sales call. So I research their company in advance. Doing your research is key in pitching.

Do you use a template for your pitches?

I have two templates now. You helped me craft one of them: I compliment the person, find a writing sample from their site, then I link to three articles I wrote that relate to that company or that publication.

I have another one that’s more specific to job boards. I use that for jobs I find on MediaBistro or JournalismJobs.

“I use a template and modify it to match the pitch. I just can’t turn off the marketing side of my business, so I’m always looking for clients, even though they might not be writing clients.”

How long does it take for you to send a pitch?

It usually takes me 10-15 minutes.

I should do a better job at organizing my samples by topic. Finding articles to show off is what takes most of my time.

How often do you change the samples that you show off?

Not very often, because I mostly write in the real estate niche.

Lately, I’ve been gathering samples from the Human Resources niche, so that has put me in a better position. I have pitch drafts for the major niches I write in.

What are your top 3 tips for pitching, Joe?

  1. Always follow instructions. Follow the directions in the job description to a T, if you’re applying to a specific job.
  2. Follow up with 10/100 rule. Your chances of getting business are better if you pitch 100 people ten times each, than if you pitch 1000 people once.
  3. Don’t feel like you have to do it one way. If something is not working, don’t be afraid to try something else: shorten your email, tweet a prospect, post on their Facebook page. Don’t feel like you’re stuck just using one strategy.

Gina’s top 3 pitching tips:

  1. In the introductory paragraph of your pitch, clearly state that you’re an expert, and that you can fulfill the needs of that particular niche. That’s what prospects want to hear about.
  2. Lead with confidence. Say “I AM the person for this job”. Don’t say “I think I am the person for this job.”
  3. Don’t highlight the fact that you’re a newbie. Don’t lie about it, but don’t highlight it. Have the confidence that you can do the job whether or not you’ve done it before.

I use Leadpages for my email list, to build that up and stay in touch with people. Do you have an email list, Joe?

I don’t.

I should look into that. (And so should the rest of y’all!)

Do you blog for yourself regularly?

Not as much as I should.

Last year, I started The Aspiring Freelancer Blog. But as I got more clients, I didn’t have as much time for it.

“Blogging for yourself is a good exercise for building your writing muscles.”

Did you track how many pitches you sent last year?

I only tracked them for the 30 Days or Less #PitchingChallenge.

I sent around 500 pitches over the last several months. I picked up around 13 clients from these efforts.

“It’s better to set a goal that’s backed by actions, because that’s what you can control. You can’t control the number of clients you get, but you can control the number of pitches you send.”

How do you follow up on the pitches you send?

I can give you the example of the last time I followed up. I gave the client a week, and then asked them “Have you made a decision about what writer you’re bringing onto your team?”

Pitch often and pitch smart. The more you do it, the better your chances to get work.

“In the first phase of your business, chase the rejections. In a more advanced phase of your business, when you already have some clients to rely on, choose quality pitches over quantity.”

Thanks for joining us, Joe!

Joe Dyton (@JoeDyton) is a freelance copywriter and journalist in Washington, DC and author of  The Aspiring Freelancer blog. He may be reached at dytonwande@gmail.com. Check out his site at joedyton.com.

If you missed our live blab you can catch the replay here:

3 thoughts on “How to Cold Pitch Like a Pro with Joe Dyton”

  1. Joe–cold calls?!? You are brave. Way to go!
    I like your theory about cold pitching (because the job boards are so inundated). Cold pitching doesn’t scare me nearly as much as cold calling! 😉 And I can’t wait until it only takes me 10 minutes to whip out a pitch email! Nice interview, Joe. Thanks for inspiring us!

    • Thanks, Renee! I was hesitant about making cold calls at first, but I wanted to explore as many pitching methods as possible. I realized the more prepared I was, the less nervous I was. So now I have a brief script I use for every call; it’s a big help!

  2. In a digital world, getting on the phone can really make you stand out as a writer. Rock on, Joe! This isn’t a great method for me because I’m trying to avoid relationships based on the phone, but that leaves plenty of gigs for writers who are brave enough to try!

Leave a Comment