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Hey folks! Today I’m answering questions from readers. If you have a question you want me to answer in a future newsletter, leave it in this thread.

The best way to leverage paid marketing to drive newsletter signups

The first questions comes from Neal Bascomb:

On Twitter, I often see advertisements for various newsletters, whether independent creators or from legacy publications like NYT and Economist. In your view, what is the most effective paid marketing for driving subscriptions (whether paid/free).

Paid marketing has become a pretty common practice in the newsletter space, especially for outlets looking to scale up very quickly. Morning Brew was an early pioneer with this strategy, and I’ve since seen many other newsletter publishers copy its approach.

I would say there are three main ways to deploy paid marketing spend (not including blackhat tactics like buying lists). I’ll start with the most effective and work my way down:

Paid placement in other newsletters

The best way to acquire a new newsletter subscriber is to be recommended by another newsletter. Not only are they self-selected as newsletter readers, but they already have their inbox open, which means they’re more likely to see and click on a confirmation email after they’ve signed up.

Lots of newsletters sell sponsorships now, but there are also marketplaces like Paved and Sparkloop that have paid referral programs you can sign up for. The way it works is that you set the maximum amount you’d be willing to pay per subscriber – say, $3 – and then individual newsletter creators can go in and grab customized links that track those conversions. This arrangement can be ideal because you only have to pay for the ads when they actually work. 

Paid social promotion

As you mentioned in your question, more and more newsletters are buying native ads on social media. There are two approaches to this.

The first is to create some kind of call to action that attempts to entice the person into directly signing up for the newsletter, usually by explaining  its value proposition. I definitely wouldn’t go this route unless you’re retargeting the ad toward people who already consumed your content but neglected to sign up.

The second kind of ad actually promotes a specific piece of premium content. These are not only better at driving clicks, but can also lead to organic sharing that you don’t have to pay for. Snigdha Sur, founder of the paid newsletter The Juggernaut, spoke to me previously about how she leverages internal analytics to choose which articles to promote with paid spend:

Paid [marketing] is usually not a sustainable growth strategy unless you have signal. The way you get signal is to *not* do paid at first and see how your articles perform. Wait about 1-2 weeks. Then put paid marketing spend behind your best performing articles. This might be obvious but I feel that marketing departments often are too quick to put spend behind something. You want to figure out if it is truly a global vs local maximum first. …

…The results? Content is often a hit driven business. Sometimes one article can lead to hundreds and even thousands of subscribers long after you’ve published it. Oh and our strategy is to do about 90-95% evergreen and 5-10% news cycle related. That increases the longevity of each piece to basically infinity. 

Influencer marketing

This isn’t as common, but I have seen newsletter publishers work directly with influencers on Instagram, TikTok, and YouTube to recommend their newsletters.

When done well, this can be pretty effective. On a recent Office Hours Zoom call with my subscribers, the political blogger Taegan Goddard mentioned that one of his biggest jumps in paid subscriptions came when a random TikTok star devoted an entire video to talking about his blog, Political Wire. He didn’t pay for the placement, but it certainly opened his eyes to TikTok’s ability to drive real engagement.

The Daily Upside, a finance-focused newsletter, also experimented with influencer marketing. Here’s how founder Patrick Trousdale described it to me:

“We're kind of a scrappy media upstart, and that resonates with a lot of creators on TikTok and Instagram. So when we reach out to creators, it's not as some big stodgy brand, it's kind of like we’re fellow creators.”

Some of this creator outreach resulted in collaborations. “Sometimes we'll almost license out some of our content or story ideas. A TikTok creator will make a video about it as if they came up with the content, but then give us a shout out at the end of the video, because it was our legwork that they used to make the script.”

Overall, I wouldn’t recommend diving into influencer marketing unless you have a substantial ad budget and the resources to monitor the results. Mileage can vary widely depending on the influencer’s dedication to the sponsorship and the engagement level of their audience, so it’s an easy way to waste a lot of money if you’re not constantly optimizing for which influencers actually drive signups.

What do you think?

Do you want to reach my audience of creators, media operators, marketers, and tech workers?

On January 1, I plan to increase my sponsorship prices significantly, which means that if you’ve ever thought about buying an ad on my newsletter, now is the time to do so. Go here to learn everything including list size, open rate, audience demographics, pricing, and ad availability.

Quick hits

Are esports a growing market with a huge amount of future potential? Yes. Did investors get too far out ahead of their skis with assuming that esports would quickly overtake traditional pro sports in market value? Definitely yes. [Bloomberg]

It turns out media companies don’t make for very good tech companies. [The Rebooting]

Will a recession bring direct-to-consumer brands back to podcasts? [Bloomberg]

How BookTok is fueling a resurgence in fiction reading. [Vulture]

How to price your paid newsletter

The next question comes from Krystal Knapp:

What are current subscription pricing trends for B2C newsletters? I talked to dozens of journalists over the summer and many didn't have a rationale for their pricing. They assumed X was the going rate and priced theirs accordingly. How should creators determine a price? What should they factor in (including inflation and the fears of a recession)?

A lot of writers struggle with the question of subscription pricing, mostly because the per-unit cost of sending a newsletter is basically zero. At least with physical products you can start with the price of production and then calculate from there. But how do you determine the financial value of an item that costs you nothing but your time?...