The biggest mistakes paid newsletters make
Writers often make bad assumptions about what kind of content people will pay for.
Hello there! This is the latest edition of my Q&A series where readers ask me questions and I do my best to answer them.
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The biggest mistakes paid newsletters make
The first question comes from Ari:
What mistakes do most newsletters make in converting subscribers to paid subscribers?
One of my most popular articles I’ve ever published to this newsletter was called “The gritty reality for Substack’s middle class.” It talked about the brutal economics for subscription businesses and the disappointment many writers face when they realize how difficult it can be to convince their readers to turn over their credit card information.
Publishers like The New York Times and Bloomberg make it look easy when they generate thousands of subscriptions a month, but they employ entire teams dedicated to optimizing content and reducing churn. The average newsletter writer just doesn’t have access to those kinds of resources, and writers often make bad assumptions about what kind of content people will pay for and the calls to action that will convert a free newsletter reader into a paid one.
Let’s go through a few of the most common mistakes:
Not switching up their messaging
Potential subscribers exist on a spectrum. On the one end of the spectrum, you have the subscribers who simply like your work and want to economically support it. You could publish everything in front of the paywall and they’d still subscribe, provided that the price is low enough.
Then on the other end you have the people who subscribe because they truly want access to the paid content. The only way they’re going to convert is if they try to read an article and instead hit a paywall.
Most potential subscribers will fall somewhere between these two ends of the spectrum, and because of that, no single call to action will be able to address them all equally.
Too often, I see paid subscription newsletters simply copy and paste the same call to action over and over again. They’re speaking to their audience as if it’s a monolithic bloc, when instead they should be constantly swapping in new calls to action that aim to communicate the newsletter’s value in different ways.
You should experiment with different conversion strategies. One week, expose your readers to an excerpt of your paid content. The next week, try to guilt them by talking about the importance of supporting your journalism. The following week, offer a steeper-than-usual annual discount and stress that it’s available for only a limited time. It often requires exposure to several different messages before a subscriber finally converts.
Simply publishing more of the same
So many newsletter strategies boil down to this: “I will publish two newsletters a week, one on Monday and another on Wednesday. The Monday newsletter will be free and the Wednesday newsletter will be for paying subscribers.”
That strategy is only going to move the needle so far. Remember what I said before: it’s incredibly difficult to pry away the credit card information from a reader, and most readers are inundated with way too much content already. Simply offering them more of the same is not going to convince most of them to convert to paid.
Instead, you should think about how you can offer a truly differentiated product for paying subscribers. Maybe it’s access to a private message board. Perhaps it’s participation in group video chats. Or it could be just an entirely different kind of article format than what gets sent in the free newsletter. The more new features you add for paying subscribers, the easier it gets to convince your free audience that recurring payments are worth the expense.
Not trying to reduce churn
When you launch a new subscription product, those early days can be exhilarating. That’s when your most hardcore fans start converting and you have a nice hockey tick growth graph going up and to the right.
But then, about six months in, the churn starts kicking in. Suddenly, for every few new subscribers you convert, there’s one person who unsubscribes. If that ratio gets bad enough, then growth becomes extremely difficult to sustain.
There’s a reason that successful publishers like The New York Times employ entire teams who are solely dedicated to reducing churn. It’s so much less expensive to keep an already-existing subscriber than it is to acquire a new one. And even if you don’t have the NYT’s resources at your disposal, there are strategies that can help you reduce churn.
For instance, one of the leading causes for churn is simple billing failures — cases where the credit card expired or the subscriber switched banks. There are all sorts of ways you can toggle your Stripe account and other payment platforms so that these billing problems are identified ahead of time and the subscriber receives automated emails asking them to change their payment information. If that fails, you could always resort to sending them a personal email.
As for everyone else, there are several ways to steer them away from cancellation. You can monitor your open and click-through rate analytics to identify subscribers who have become less engaged. You can run exit surveys for cancellers to determine why people are terminating their subscriptions. You can offer steep annual discounts if they agree to stay on. A lot of these tactics can be automated.
No subscription business has 0% churn. But once your subscriber base gets large enough, then the difference between a 2% monthly churn rate and a 5% churn can be enormous.
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Why every podcaster should experiment with Twitter Spaces
J.B. Wogan asks:
What is the case for a podcaster to host more ephemeral Twitter Spaces conversations in addition to their permanent, recorded content?
Let’s start with a quick primer to make sure everyone is up to speed: Twitter Spaces is one of the many Clubhouse clones to emerge over the last year. Essentially, one or more Twitter users can host a Spaces room, and it’s basically a cross between a conference call and a live webinar. Not only can the hosts speak to the room, but participants can raise their hands and be called on to speak. For the most part, Twitter Spaces are audio only, though the hosts can embed different forms of media at the top.
Now, let’s get to your question: should podcasters start hosting live Twitter Spaces?
Yes, I think they should at least test out the format. Here are a few reasons why.
It’s the best of the live audio tools
Yes, Clubhouse is the OG live audio platform, but it’s never had a very strong value proposition for most users. Let’s face it: live audio is a niche offering, and the vast majority of live sessions aren’t very interesting, especially if you hop into them mid-conversation. Because of that dynamic, Clubhouse has never been worth the effort of adding it into your mobile app rotation.
Twitter Spaces, on the other hand, fits into your already-existing social graph. You can be surfing through your timeline and then all of a sudden see a tweet from a favorite podcaster or YouTuber announcing they’re launching a Twitter Space session, and with just a single click you’re suddenly listening to a live conversation with a social media personality you already know of and admire. You can even leave the Space open in the background as you continue surfing your Twitter timeline. It’s just such a low-friction environment, especially for those podcasters who already have a large following on Twitter.
A Twitter Spaces session can be repurposed as a podcast episode
Longtime readers of this newsletter know that I’m a huge proponent of repurposing content, and that’s especially true for podcast recordings. Twitter allows you to natively record Spaces, and it doesn’t require too many technical hurdles to distribute that recording into your podcast feed. Case in point: the Techmeme Ride Home podcast invited me to participate in a Twitter Spaces event several months back and then later published the discussion as a podcast episode.
Is the audio quality serviceable? I’m not going to say it’s the same level of quality that you get when you’re recording with a dedicated microphone, but I’ve found that a minimal level of editing that eliminates the awkward pauses can produce the same level of audio fidelity that you get from recording a live conference panel, and those get repurposed as podcast episodes all the time.
It’s a great way to add a level of interactivity with your audience
I’ve been producing my own podcast since early 2018, and I’d say that it’s a pretty lonely experience. Other than the raw download numbers, I get very little feedback as to whether my content resonates with my audience. Every now and then someone will tweet at or email me when they enjoy an episode, but for the most part, it’s a one-way relationship.
Twitter Spaces provide a great way for a podcaster to go out and actually meet their audience, and I think Spaces could help strengthen your relationship with your already-existing listeners. I don’t have any hard data to back this up, but my guess is that a listener who has a conversation with you in a Twitter Space session is more likely to listen to your episodes and even recommend your podcast to others. We’ve long talked about the “intimacy” of podcast listening — a level of intimacy that doesn’t exist on most other mediums — and I think that a live audio experience could strengthen that parasocial relationship even further.
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Legacy newspapers keep eliminating print editions. [WashPo] To be honest, I find it kind of strange that print newspapers still exist considering that I don't know a single person my age or younger who reads print versions with any regularity.
I'm talking to more and more content creators who bristle at the idea that just because a media company contracted work from them, that it therefore owns all the IP associated with that work. In fact, I have an upcoming podcast interview with a famous writer whose motivation for going to Substack was because he could own 100% of his IP. [Poynter]
Lots of media startups have experimented with live video news (who remembers HuffPost Live? How about BuzzFeed's morning Twitter show?), but I have a hard time thinking of many that actually succeeded. [Digiday]
"In 2021, with about 285,000 followers on Instagram, 220,000 on TikTok, and 37,000 on Pinterest, she made $241,000 as a creator." [Insider]
A reminder to struggling creators: sometimes it feels like you're failing when in reality you're just building the foundation. [Digiday]
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