๐Ÿฆโ€โฌ› Total stranger -> paying client (my playbook)

Cold Pitching Strategies
(That Actually Work)

ยท August 7th, 2025 ยท

Hey friend ๐Ÿ‘‹

Cold outreach can be one of the most miserable tasks you’ll ever undertake.

Most freelancers I know would rather spend the day scrubbing the bathroom ’til it shines than send one more cold email.

No one likes begging for work. It sucks.

If you opened this email hoping I have a magic solution to make it un-suck, sorry. Until I learn how to become a wizard, that won’t happen.

But if you’re going to spend time cold pitching, you might as well make sure you get your money’s worth (literally).

These days, I don’t do a whole lot of cold pitching. Most of my work comes to me through referrals. (Here’s a good post on that if you’re interested).

That said, I’ve spent my fair share of time sending cold emails trying to find work.

This week, I’m sharing the exact framework I’ve used to keep my freelance writing calendar full for nearly a decade.

Hope you find it useful!

Best,

๐Ÿฆโ€โฌ› Cody – Founder @ Ravenwood Writing Academy

P.S. What is one cold pitching tactic you’ve had success with? Hit reply and let me know. I want to create a list of everyone’s best tips and share with everyone next week. Teamwork helps us all (get) work!

๐Ÿง› Freelance Bites:

News and Resources in 2 Minutes

  • Placed is a great new hub for connecting your pitches with editors who are looking for stories. Check it out here and sign up for free.
  • If you’re also a fiction writer, like me, you’ll love Fabled Planet! They have a ton of great resources on writing (mostly fantasy/sci-fi), including monthly masterclasses and a fledgling community of awesome writers. Check it out! (Fabled Planet)
  • What’s one easy way to grow your freelance writing business. Well, I’ll just let Kat Boogaard tell you (LinkedIn).
  • SEO is always changing. No, you can’t escape it… sorry! Here are some predictions on SEO trends for the rest of 2025 from the folks who literally wrote the book on it (Hubspot).

๐Ÿ“ฌ Letters From My Desk

Cold Pitching for Freelance Writers: Turning Strangers Into Clients

If youโ€™ve been freelancing for any length of time, youโ€™ve surely heard the advice, โ€œJust put yourself out there.โ€

Which is greatโ€ฆ until you realize that โ€œout thereโ€ often means cold pitching. Reaching out to people who have no idea who you are and asking if they want to work together sucks.

Not my idea of fun. Iโ€™m sure itโ€™s not yours either.

That said, cold pitching is often a necessary evil if youโ€™re a new freelance writer or just need to fill space on your calendar. Eventually, you can start getting most of your work from referrals.

But until you get there, outreach is key.

Cold pitching takes time, research, and lots of mental fortitude. If done right, it can give you control over your client pipeline and your business.

So, what does โ€œrightโ€ look like?

1. Shift Your Mindset

Thereโ€™s a big misconception about cold pitching. Most people think it means sending a hundred emails to a list they scraped up and hoping for the best.

Itโ€™s not.

Cold outreach also isnโ€™t about closing a deal. If you lead off asking for a job, youโ€™re going to be turned down 99.9% of the time. If a client was that desperate for a writer, they would have already been looking for someone. The chances of your email finding them at the exact right moment (without some sort of indication that they want to hear from you) is basically zero.

Successful cold pitching is about curiosity.

Your goal isnโ€™t to land a job, but to get a client hooked and ready to hear more. If you can do that, your prospects are far more likely to respond.

2. Build a Shortlist

โ€œTraffic Secretsโ€ by marketing expert Russel Brunson is a fantastic book that I recommend every entrepreneur read. In it, Brunson suggests making a Dream 100 list. Thatโ€™s one hundred clients you would LOVE to work withโ€”no matter how realistic.

From there, youโ€™re able to craft a more targeted pitch thatโ€™s focused on the specific pain points your ideal clients are experiencing.

If 100 is intimidating, start small. A shortlist of 25-50 companies is better than a database of 500 random ones.

You should also prioritize companies that are ready and able to hire a freelance writer to create their content. I recommend looking for green flags like:

  • Regularly sharing success stories or thought leadership
  • Recently launched a product, secured funding, or hit a major milestone
  • Active publishing on LinkedIn or industry blogs

3. Do a Micro-Audit

Before you reach out, you have to do your homework. People can smell an unprepared pitch from a mile away, and itโ€™s a shortcut to the spam folder.

Spend some time looking at their website, blog, LinkedIn page, and even sales decks if theyโ€™re public.

Find one specific gap where your work could help. Maybe they have great testimonials but no case studies. Maybe they recently announced a company win but havenโ€™t shared the story beyond their website.

Leading with an observation tailored to their business helps you stand out from the thousands of โ€œIโ€™m a freelance writer, hire me,โ€ messages clients see every day.

4. Write a Personal Message

Remember, the goal isnโ€™t to sell here. Your message is about driving curiosity and getting the person on the other end to read it to the end and take action (reply).

Iโ€™ve found in my years of doing cold outreach that the simple formula of Insight + Invitation works best.

  • Insight: Reference something specific youโ€™ve noticed about their work, achievement, or challenge.
  • Invitation: Offer to show them what a solution could look like, with no strings attached.

This structure shifts the focus away from selling your services toward giving the client a reason to continue the conversation.

Example: โ€œI noticed you helped [Client] achieve [Result], but I couldnโ€™t find a public story about it. Would you be interested in showing other customers how your solution delivers results like this? This type of story is one of the hottest tools in marketing right now. If youโ€™re curious, Iโ€™d be happy to mock up a quick outline. No pressure!โ€

5. Deliver Value Upfront

One of the fastest ways to build trust with a stranger is to give them something useful before they pay you a dime.

It could be a simple story outline or a short list of content ideas. It could be a quick video message offering a professional critique of their existing materials. Or you can go deeper and create a custom piece of content that shows how you can solve their problem.

When you do this without expectation, it creates immediate goodwill. It also demonstrates your expertise far better than any resume or writing sample ever can.

It also lets you leverage the principle of reciprocity (a proven psychological trigger). When you give freely, others are naturally inclined to give back. Sometimes that can be in the form of a paid project.

6. Follow Up (More Than Once)

I cannot stress this enough. Most deals donโ€™t happen from the first cold outreach message. In fact, Iโ€™ve landed the vast majority of my jobs from the second or even third follow-up.

Be sure to reconnect after about a week. Keep your messages friendly, light, and reference something new if possible. A recent update can catch their eye.

If they donโ€™t respond after two or three tries, move on gracefully.

Play the Long Game

Cold pitching wonโ€™t transform your client list overnight. Iโ€™m sorry to say it.

Over time, though, a strategic approach will yield a network of warm connections and paying clients. All from one thoughtful pitch.

When youโ€™re ready to start sending better cold pitches, head on over to the website and grab our FREE Cold Pitch Quick Reference Checklist to stay on track.

Cody’s Top Picks

This is the part where I share some of the content Iโ€™ve been enjoying lately. Hope you enjoy!

(This section may contain affiliate links. If you make a purchase through these links, Iโ€™ll earn a small percentage, which helps support this free newsletter at no extra cost to you.)

  • ๐ŸŒ Iโ€™m Doingโ€ฆ Hiking at Mount Rainier National Park. Our time in Seattle is getting short, but we finally made it to this bucket list park. The Skyline Trail was stunning, from glaciers and meadows to waterfalls and a friendly marmot. I even got to rep Ravenwood atop the peaks.
  • ๐Ÿ“บ Iโ€™m Watchingโ€ฆ “Quarterback” on Netflix. I’m a huge NFL football fan (Broncos are winning the Super Bowl this year) and I’ve loved this inside look into being a quarterback at the highest level. It really scratches that “Hard Knocks” itch when it’s not in season.
  • ๐ŸŽง Iโ€™m Listening toโ€ฆ2010s Emo Punk Rock” on Spotify. This playlist has so many awesome throwback hits. I’ve had it on pretty much non-stop this week.
  • ๐Ÿง  You Should Remember:
โ€œIf you believe in something, sell it.โ€ โ€” Unknown

More From The Blog…

How to Turn Your Network Into a Freelance Referral Engine: Part II

Want more freelance writing referrals? Start leaning on your network! Here are three ways to encourage people to share your message.

My Client Ditched AI and Hired Me Back. Now I Charge Them Double

AI wonโ€™t replace great freelance writers who have a niche. Iโ€™m charging a client double after they hired me back because AI failed them.

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Sharing the word helps our human-first writing community grow. ๐ŸŒฑ

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P.S. Please donโ€™t sign up with your dogโ€™s email or create fake accountsโ€”weโ€™ve got surprisingly good spidey senses for that kind of thing ๐Ÿ•ต๏ธโ€โ™€๏ธ (and they won’t count).

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ยฉ DeBos Ventures LLC // Ravenwood Writing Academy 2024

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