How to leverage live audio to drive paid subscriptions

PLUS: How Richard Rushfield built The Ankler into a thriving industry newsletter

Welcome! I'm Simon Owens and this is my media industry newsletter. If you've received it, then you either subscribed or someone forwarded it to you.

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Let’s jump into it…

My latest: The products that Jared Newman, the tech journalist behind Cord Cutter Weekly, can’t do without

Jared is a longtime tech journalist who’s written for Fast Company, PCWorld, and TechHive, the latter for which he’s written a weekly column about cord cutting since 2014. In 2016, he launched Cord Cutter Weekly, a weekly newsletter that helps people learn how to ditch cable TV and maximize their savings on streaming services. It now has more than 30,000 free subscribers, with weekly open rates above 50%. In 2018, he launched Advisorator, a newsletter that offers the kind of tech advice you’d hope to get from a geeky friend. Each newsletter has an in-depth advice column, some quick news hits, new apps to try, and deals. It now has over 1,000 paying subscribers.

Jared walked us through the products that are absolutely essential to his business. You can find our interview over here.

BTW, I’m still looking for creators and media entrepreneurs to feature in this series. Each interview is heavily featured in front of my 14,247 newsletter subscribers, and I share it out to my 70,472 social media subscribers. Go here if you’re interested.

Do you live in the Washington, DC area?

Each month I organize a dinner with other media operators in the area. I keep these pretty small and intimate — around six people max — and they’ve been incredibly fun so far. They’re completely free to attend (you just have to pay for your own meal). If you’re interested in being invited to a future dinner, reach out to me.

Quick hits

Now THIS is a great way to leverage live audio. I especially liked this part: "Anyone can listen in, but only subscribers can ask questions using the chat-like text box or being invited to speak by one of the hosts." [Nieman Lab]

"James Daunt, the CEO of Barnes & Noble and of British bookstore chain Waterstones, told Insider last year that BookTok created a phenomenon unlike any other he'd seen in 35 years as a bookseller." [Insider]

I think this is probably a smart way about approaching VC investments for media companies: specialize in a specific content vertical and inject small amounts of money into promising ventures to help take them to the next level. [Axios]

Music blogs were incredibly influential in the mid 2000s. I remember being able to surf these blogs and then download all sorts of songs to my iPod. They embedded the mp3s directly into their posts so all you had to do was right click and download. [NYT]

Wow. YouTube is now a much bigger business than Netflix. And a lot of that revenue is flowing directly toward creators. [Bloomberg]

Did I give bad advice about delaying a paid subscription launch?

Earlier this week, I published a piece on the perils of launching a paid subscription product too early. I argued that doing so could limit your audience growth, decrease your paid conversions, and blind you to other monetization opportunities.

I got plenty of pushback on my thesis.

Ari argued that there’s a path to launching a compelling subscription product without hindering audience growth:

I think the harm surrounding launching a subscription product too early is entirely dependent on your product.

If your paid content is similar to your free content, or, even better, has more viral potential than your free content, then yes, putting it behind a paywall will slow your growth. IMO, the best setup is a consistent free product that is viral, very good, and drives growth, alongside a completely separate and distinguishable paid product that provides a lot of value to those who like the regular content and are willing to pay.

In that case, starting the paid product as early as possible is key, because it gives you time to (1) perfect the paid product and (2) find the correct combination of free and paid that is conducive to growth. Introducing a paid product too late in the game could make flaws with the free product pretty obvious.

Suw Charman-Anderson says that delaying a subscription launch would prevent your audience from supporting your work:

As others have said, I think it really depends on who you are, what you're doing, and what people are actually paying for. If they're paying for the product as a product, then yes, you're going to need a bigger audience in order to convert and there's the risk that putting too much energy into a subscription product is going to take time and effort away from growing your audience.

However, if people are paying because they like you and what you do, if they are essentially donating because they want you to succeed, then you need to turn on subscriptions asap so that you can benefit from that generosity. It's also valuable to build up a library of paid articles as that increases the attractiveness of the offer, and it's easier to do that early on.

I also agree with those who've said that it's helpful to be able to experiment and iterate quickly on what you're offering for paid tiers, but that depends again on what kind of audience you have, how much audience data you're starting with, and what you have the capacity to do. So I do think it's pretty complicated and people, esp on Substack, have to think about what they can feasibly do and what the implications are in terms of time and resources.

Pete Ericson offered a way to keep your content free but also build up a large list size that you can sell to once you’re ready to launch a paid product:

I would make sure all my content was published on my website and set up a metered paywall with free registration wall to build my audience. This lets my content stay visible in search and social media. I might target 3-12 months of full access until I decide it's time to pull the trigger on paid access. The free registration remains and changes to offer extra content access and my free newsletter (content excerpts). The free newsletter's job is to drive readers back to my site to trigger upgrade messaging for full paid content access on my website.

And finally media analyst Thomas Baekdal thinks a paid subscription keeps you focused on the metrics that matter:

I disagree with this. I think it's vital for independent publishers to start monetizing early, otherwise they will be distracted by traffic goals that will make it much harder to convert people later. And I know this from experience. I made this exact mistake when I started.

I do agree that it's vital to create momentum and have something that brings people in, but I tell everyone to make sure that their primary focus and value is monetized from the start.

How Richard Rushfield built The Ankler into a thriving industry newsletter

In the world of media startups, The Ankler is one of the most exciting outlets to watch. What started out as a single newsletter authored by entertainment journalist Richard Rushfield has morphed into a full-fledged trade outlet. In the last year or so, it’s raised $1.5 million in seed funding, recruited a former editor from The Hollywood Reporter, and launched a bevy of talent-led newsletters. In 2022, it brought in seven figures in just sponsorship revenue alone.

In a Zoom call earlier this week, Richard walked us through how he launched his business, what drove conversions for his paid product, and why he decided to take VC investment to scale up the business.

You can watch our conversation in the video embedded below:

If video embeds don’t work in your inbox, go here.