Newsletter #19 – My Highest Earning Newsletter So Far

Hey everyone,

I’m writing this email from Dresden, where I’m working for a couple of weeks before heading back to Berlin.

If you’re not familiar with Dresden, it was once considered one of the “jewels of Europe” and it was also a major part of Germany’s rail network – which made it the target of a brutal, 3-day blitz by the US and allied forces in WW2.

The entire city was flattened and then gradually rebuilt from the rubble. So there’s a certain emotional weight to the place.

And if you read Slaughterhouse 5 at school (when I came up out of the meat locker, the city was gone…), that iconic building is still here.

It’s an incredibly beautiful city to walk around.

Today’s newsletter marks 6 months of sending weekly emails. Thanks for reading, I appreciate you!

As many of you know, I LOVE testing out different ideas for side-income streams.

So I thought I’d take you along on my newsletter growth journey so far:

  • Start date: January 1, 2023
  • Subscribers: 1,912
  • Average open rate: 55.8%
  • Average click through rate: 8.2%
  • Total newsletter earnings since January: $1,798.99

That’s about $359 a month from 1 January to 1 June. Not bad.

I’m only doing basic promo posts about this newsletter on Twitter and LinkedIn, so I fully expect this growth to stall soon. I’ll do another update at the 12-month mark.

For most people, it can take 2-3 years (or more) to reach 50,000 subscribers, so there’s a LOT of writing, testing, and thinking to be done.

My topic is relatively niche (the business of freelancing) so those big numbers might not even be possible.

And we might have already reached ‘peak newsletter’ too, based on this Fast Company article, so these are all things I’m factoring in.

Why I didn’t set this newsletter up on Substack

Substack is all the rage for creators right now, but I’m not a huge fan of “building on rented land”.

I’ve seen many founders and creators get seriously burned by building their products on third-party platforms. When those channels died or changed their business models, the creators’ businesses disappeared overnight.

Creating your own mailing list is definitely the harder option, but you can monetize it much better, and you’re not at risk of losing all your hard work to the random whims of another company.

How I got 498 new subscribers in 2 days

The article I wrote about “How to earn $100k to $400k as a content writer” smashed through all my expectations about how popular this topic would be.

I send the link to my newsletter readers before I publish it online, and as a result my subscriber numbers exploded in the couple of days before this article went live.

Not sure I’ll ever be able to repeat that, but I’ll keep trying!

The newsletter that earned me $1,022.50

A couple of months back, I sent out an email that made me nervous about launching it into the wild.

But as I keep preaching to anyone who will listen — we all have to do uncomfortable things to grow our business sometimes, and we need to test what works and doesn’t work for us personally.

So after editing, re-editing, and re-re-editing I finally hit “send”.

And watched a ton of people unsubscribe.

I also got a couple of emails asking what the heck was up with the sales pitch…?


Right before my weekly email was due to send, I got approved as an affiliate for the Copy School training courses.

This has a launch window of only a few days, so I didn’t have time to think up anything clever to send out, and I couldn’t wait until the next week.

I shared my personal story about how these courses seriously levelled up my income and the types of companies I work with.

Would I have felt confident enough to pitch and win clients like Uber, Amazon, and Stripe without this training?

Absolutely not.

So I didn’t hesistate to promote these courses hard. They’re 100% the real deal.

I did a couple of social posts to promote the email and had about 200 new email signups from that. All up, this translated into a handful of Copy School sales, and a decent amount of Sparkloop income too (you can read more about that below).

Despite the overall awkwardness – that one, nervous, sweaty, email send earned me $1,022.50.

Was it worth sending? Totally. Would I do it differently next time? Yep.

Copy School doesn’t open again until 2025, so I have lots of time to prepare.

How I monetize my newsletter

I’m a pretty transparent, no BS person, and I run my business the same way.

It’s no secret that some of the links in my newsletters are affiliate links (I have this disclaimer at the end of each email) — and I’ve been asked a few times why I do this.

So here’s the facts:

First, the bigger this newsletter gets, the more it costs to run. My current ConvertKit plan costs $490 a year for up to 3,000 subscribers.

So once I get another 1,000 subscribers, I’ll paying $790 a year.

That amount of money puts a serious dent in my fancy cheese budget.

Second, I fully set out with the intention to build this newsletter into another source of income outside of client work. How exactly, I didn’t really know – but everything is figureoutable, and it’s fun learning about this stuff.

Third, writing a newsletter I’m happy to send out each week takes hours. So if I get a couple of dollars back when someone shouts me a coffee or buys a book through a link, it really motivates me to keep going.

Here’s how I’m monetizing right now:

Sparkloop – this is a total no-brainer if you want to start making money from your newsletter.

Even if you only have a trickle of subscribers, adding this to your signup page can help you get in a bit of cash each month without any effort. It feels like free money – and who doesn’t love that!

My highest earning month so far was $158. A typical month for me is around $60. Sparkloop also lets you set up a referral program to help grow your list, so I’ll be looking into this soon as well.

* Affiliates – I apply for affiliate accounts if I absolutely LOVE a product and think it would be useful for other freelancers.

These include courses I’ve taken, the copywriting coaching I recommend, books I’ve read etc. Affiliates are by far the best way to make money from your newsletter – BUT – you need to find the programs that are 100% relevant to your readers.

* 1:1 clarity calls – I get a lot of people in my inbox asking for advice, looking for help to iron out some sticky stuff in their business, and people who just want a sounding board to get some feedback for ideas, offers, pricing and so forth.

A few of these people have booked 1:1 clarity calls through my newsletter link. It’s a great way for me to meet new people and expand my network too – so thank you to everyone that’s booked a call so far 🙂

* Buy me a coffee – although getting $5 seems like a small amount it’s still very exciting when I get these notifications. A big thanks to everyone who’s pressed this button!

If you’re starting a newsletter, or you’ve been growing one without monetizing it yet, my advice is — don’t wait until you’ve hit 500, 1000, or 2000 subscribers — start looking for ways to get your newsletter paying for itself as soon as possible.

If you’ve got time on your hands, it’s free to start a newsletter with tools like ConvertKit or MailerLite — so you can try your hand at creating emails that could eventually turn into another source of income for you.

Remember that freelancing is only part of your business journey, and there’s a point where most freelancers want to seriously cut back on client work.

There are a ton of other things you can do to boost your revenue, help you learn new marketing skills, and maybe even take you in a whole new direction.

Whether that’s a newsletter, a course, consulting, making a digital product, or starting a YouTube channel – there’s never been a better time to start exploring new ideas for your business.

Have a great week!


Oh wait – I almost forgot! If you’re reading this, you’re automatically in the draw to win one of 3 annual subscriptions to Freelancer Magazine.

I’ll be doing a random draw this week, and I’ll announce the winners in next Monday’s email. You’ll get a personal email this week with all the details if you win a sub.

Good luck!

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