So you want to start a newsletter in 2022, you say?

Never let it be said that a journalist respecting his time will let any amount of unused work go to waste: yours truly was invited to fellow journalist Valia Kaimaki’s Sunday radio show about a month ago to discuss how the much-talked-about trend of newsletters as a viable alternative for professional journalists is evolving. Available airtime inevitably proved to be short for that broad a subject, but the part of the discussion that did air can be found here on Spotify. Apologies if it all seems Greek to many of you but, well, it kind of has to be when aired on a Greek National Radio show!

The whole thing, though, makes for a great anniversary post: today marks a year since yours truly started Entechtainment Today, his very own Substack newsletter about tech and entertainment. Yes, it’s been twelve months already! So, after 200 issues of that newsletter sent out in the course of a difficult year, what’s the main takeaway for professional journalists thinking about starting theirs? Why start a newsletter in the first place, regardless of profession? Is Substack really all that? Can one expect to make a living out of a newsletter? How about some practical tips that would help move things along? Answers!

Why start a newsletter anyway?

There are hundreds of articles out there exhaustively answering that very question but… it’s simple really: because it’s the most personal and most sincere form of content delivery at the moment. That makes it, at the very least, interesting. People subscribe to your newsletter because they mean to. They are genuinely interested in what you have to say. You write stuff for them to read and have it delivered straight to their inbox. You don’t work for a media outlet that may or may not have an agenda, you don’t answer to an editor that may or may not like what you have to say. For journalists freedom of speech is important and their personal newsletter offers them that.

For everyone else, it makes sense in other ways. Content creators and writers in general start newsletters in order to connect with readers in the most direct way possible and build an audience around the stuff they want to publish. Business people use newsletters to establish a presence that can be leveraged later in various ways: growing a mailing list of recipients interested in what one has to say, for instance, makes for a very effective marketing tool.

Practical experience proves this: yours truly is still astounded — after running Entechtainment Today for a year — by how high the open rate of that newsletter on Substack is compared to the newsletter he’s running for his day job. The latter boasts an open rate of 25%-30%, which is considered great by any standards. That Substack newsletter? Never less than 45%, usually about 65% and an all-time record of 90%, depending on the kind of story published. That’s huge. No other content platform can achieve that, period.

Sounds like fun, but is there a business aspect in all of this?

Believe it or not, there is. It all comes down to the “1000 True Fans” manifesto of Kevin Kelly, the founding executive editor of Wired magazine. It was written all the way back in 2008, it’s well worth a read in 2022 for a lot of reasons but — as far as this newsletter thing is concerned — here’s the main takeaway: according to Kelly, for every creator willing to provide a steady stream of quality content there are at least a thousand people out there in the world willing to support his/her efforts. Not just people enjoying his/her work, but people actively helping in making that happen.

Substack, the most famous platform for starting and maintaining a newsletter at the moment, makes it really, really easy to set one up in no time and — crucially — easy enough to manage free newsletters, paid newsletters or a mix of both. So what most people writing articles about Substack advise is that everyone just getting into the newsletter game should start offering a free newsletter in order to start building his/her subscriber list, as well as his/her brand, immediately. After that list has become large enough, anyone can convert their newsletter from free to paid — or to a hybrid one, offering some issues for free while subscribers get access to all of them — in order to start making money out of it.

Substack itself makes it clear in its own helping guides that when a newsletter owner “flips that switch” from “free” to “paid” or “hybrid” he/she can expect no more than 10% of subscribers to actually pay for the privilege (5%-10% is most often the case). But if the mailing list one has been building over time exceeds e.g. 10.000 or 20.000 subscribers, then 10% or 5% of that provides a person with an income of $50.000 per year (minus some platform and transaction fees). It’s all going back to Kelly’s “1000 True Fans” manifesto: if one manages to reach enough people so as to “drill down” to those one thousand supporters, he/she can essentially create an annual $50K small business venture on Substack.

Bearing in mind that there are now more people on the Web than back in 2008 — and that it’s easier than ever to promote a small business — some creators and writers can earn much more than $50K in a year.

Great! So just doing this Substack thing will make me rich, yes?

No. If only it was as simple as that. A thousand true fans may not sound like a lot of people to find on the Web today, but they are… well, scattered. All over the place. One has to reach a lot of people — an awful lot, actually — in order to find those 1000 fans willing to support his/her work financially. There is no easy or quick (legal) way to achieve that with a newsletter other than putting in the work and spreading the word. That takes time and effort. Lots of it.

What is worse, Substack does not do nearly enough to promote new newsletters and new writers. It only highlights the most successful paid ones — because it stands to gain the most from the expansion of their subscriptions — only making frequent recommendations in its own newsletter (!), which is not all that helpful. Discoverability on Substack’s website is so low right now that it’s practically up to the owner of a newsletter to do all the promoting — otherwise, chances are that it will not gather enough subscribers to ever find its “1000 True Fans”. That might or might not change in the future, but as of March 2022, it really can be disheartening.

So there’s just no guarantee that starting a newsletter will actually make anyone money, especially short-term. The only way this model can work fast on Substack, or any other newsletter service for that matter, is obvious: if the writer or content creator already has a loyal following, then yes, those people will probably continue to support him/her on a new platform too. But chances are that the people who already have that kind of brand power do not need to get into the newsletter business in the first place (and that is why Substack itself will offer serious money to get them on its platform).

There’s always the “slow and steady” approach, of course. People with day jobs and/or other sources of income can start a newsletter and be patient about it, investing as much time as they have available in writing and promoting their work. It will take way more time than it would if they focused all their energy and time on that newsletter, but for people who have that luxury it’s a viable option. Many content creators have “side hustles” like this nowadays and newsletters can be managed that way too.

OK, then. Got any tips for people eager to start their newsletter?

The question that spawned a thousand SEO-optimized answers, to be sure, but yours truly will only include advice that he himself has found useful. In no particular order, the following.

First of all, pick a niche. Nobody is an expert at everything and, since you will strive to provide value to readers, make sure you start out with stuff you know a lot about. Some people have many areas of expertise and can easily juggle between them, but being an authority on a subject is valuable and really helps in drawing interest to what one has to say.

Then be consistent. When sending out a newsletter it’s easier to establish a personal relationship with your readers if they know what to expect from you and when to expect it. If you plan to send out stories three times a week and have claimed to do so, do that. If only once a week, do that. But try not to backtrack on your promise, especially in the beginning.

Try to be concise: newsletters can be about anything, so stories published in that form can wildly vary in length, yes. But a lot of people open those newsletters on smartphones or tablets, so 10000-word stories just won’t be read as much as shorter ones. When taking into account people’s shorter attention span as well as the way they receive your newsletter (it is an e-mail among many other e-mails they’ll be receiving in their mailbox during the same day), it’s obvious why it pays to not publish stories longer than 1000 words (that’s a 4- or 5-minute read) very often.

Make sure that you focus on quality. It’s highly unlikely that you’ll be sending more than one story per day in your newsletter under normal circumstances, so make that one count. Make it as well-written and informative as you possibly can. People may be scanning article headlines from website homepages all day long, but when they open your newsletter, they expect to read something worth their time. Do your best to offer them that.

Understand that promoting your work is as important as writing it. There’s no “if you build it, they will come” in the modern content industry. In the case of newsletters, you have to make time for letting people know about yours. Use social media, comment sections, guest writing, anything that can make your newsletter known to as many readers as possible. If they come and they recognize the value on offer, they will subscribe to your newsletter. But they have to know it’s out there first!

So, long story short: go start a newsletter if you have things you want to say, if you have enough time to do it well and if you understand that you’ll probably be playing the long game when investing time in this. It’s hard, but not impossible to make a living out of a newsletter. Decide how you want to play this and go for it. A Thousand True Fans are not that many, after all, are they?