Does a creator even need 1,000 true fans?

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Does a creator even need 1,000 true fans?

A few weeks ago I published a newsletter that curated some really good insights from an independent creator who’d successfully built a thriving membership program from his Apple-focused content. 

In the piece, I wrote about my own struggles maintaining a strong output of both free and paid content:

As someone who’s trying to build his own paid subscription offering, I struggle each week to produce enough high-quality content to deliver to both paying and non-paying subscribers. If you don’t produce enough good free content, then you can’t get new readers into your sales funnel so that you can convert them into paid subscribers at a later date. If you don’t produce enough paid content, then your already-existing subscribers will wonder why they’re paying you at all.

A few days later I received an email from Josh Specter, who runs the For the Interested newsletter. 

Hey Simon, I dig your stuff and just want to offer some unsolicited feedback as someone who's spent a lot of time in the newsletter (free and paid) space and does a lot of thinking about how the whole world seems to be trying to sell paid newsletters these days.

I think what you're getting at here is obviously a common challenge for people trying to build paid newsletters, but increasingly I'm starting to believe it's because they're approaching paid newsletters in the wrong way.

I'm not sold that the idea of selling subscribers "more" content is the best approach. I think you may be better served trying to sell  "different" instead of "more." Most people don't want extra emails - even if they're good - so they're unlikely to pay for extra emails. Getting people to pay for anything is challenging to begin with, but trying to sell "more content" I think makes it even more difficult.

I'd recommend thinking about what you could offer that would be different in some way - a product, resource, service, access, different format, etc. Or, a newsletter that's on a slightly different topic or spin to more clearly differentiate it as a product from your free newsletter. It would also make your life easier as relates to figuring out what content goes where.

Unfortunately, I don't have a specific recommendation for you, but I'll throw out a random (and probably not great) example...

Imagine if instead of a $10/month subscription you held a monthly Zoom meetup with an industry expert and limited participation to 10 people who would pay a premium to join (maybe $100? per meetup or $600 for a year pass or something).

In that scenario, they're paying for access to this person, it's a networking event in some ways in addition to being content, you need a lot fewer people to "convert," it's likely less work for you each month, etc. You could even then have a lower paid tier where people get access to a recording of the Zoom meetup/Q&A after the fact for a lower price (maybe that's your $10 a month).

I'm not saying that would necessarily work, but it's an example of selling a different product that represents potentially greater value to your target audience.

One other idea - Try to pre-sell a "package" of content before you create it.

For example, if 200 people pay $10 each for you to put together a series of 5 interviews with a certain type of industry leader, you greenlight the project (and you don't have to put in the work until you sell it).

Long story short, I think it's easier to get people to pay for "a thing" than to pay a subscription for a generic "more."

Josh touched on something I’ve given a lot of thought to over the years: how do you design something that people will actually want to pay for? He’s right, in that there are a lot of people who are perfectly happy receiving one or two free newsletters from me each week, so would they really want to pay for even more to land in their inbox?

He also touched on an idea that I’ve seen discussed more often lately in the independent creator space: Why bust your ass trying to find 1,000 true fans to pay you $100 a year when you can find 100 mega fans to pay you $100 a month? In other words, could I design a product or service that’s so premium that I could charge at a much higher pricepoint and therefore only need to convert a smaller portion of my free audience?

Believe me, Josh, I’ve racked my brain about how such a product would be designed, and I’ve come up mostly empty. Let’s take your suggestion as an example: could I find one influencer a month and set up a session where 100 people could pay $100 to participate in an intimate Q&A with that person? Sure.

But could I actually get 100 people to sign up? I doubt it. To be clear, I think a publication like Digiday or Business Insider has the kind of  marketing reach to pull this off. But my audience is relatively tiny compared to theirs. I think I’d need something like 100,000 free subscribers to my newsletter just to convert 100 of them into paying $1,000 a year for some super exclusive product. And I certainly don’t have 100,000 free subscribers.

I’ve seen some creators attempt to approach this challenge by creating some comprehensive course and then charging users a relatively high price -- $500 to $1,000 -- to enroll in it. Could that work for me? 

I’ll actually answer this question further down in the newsletter. Keep reading...  

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The challenges of selling online courses to your audience

If you spend any amount of time listening to podcasts or even perusing social media platforms, you’ve likely come across an ad for MasterClass. Its pitch is simple: spend a few hundred dollars a year and you can take online courses taught by actual celebrities. You can learn about the art of film from Martin Scorsese or how to play tennis like a pro from Serena Williams. These aren’t D-list celebrities. The company has access to actual superstar talent.

And how can it afford this access? Certainly not from revenue alone. The company just raised a monster $100 million Series E round at an $800 million valuation. According to Crunchbase, it’s raised $236.4 million since its founding.

But one thing I’ve always wondered is if its courses are worth paying for. Is Martin Scorsese actually taking the time to craft a comprehensive course that will advance one’s filmmaking abilities? This description from TechCrunch left me doubtful:

Despite its flashy lineup of stars, MasterClass doesn’t sell access but instead sells a window into someone’s work diary. Celebrities are not interacting with students on a day-to-day basis, and sometimes, not at all.

It is relatively a light lift for celebrities once they get their content on the platform, which of course only happens if they are personally invited by the company. Any MasterClass on the site includes a number of lessons, broken down in separate videos that range from 20 to 30 minutes, and a downloadable workbook. Students for each class can flock to community hubs to chat with their fellow virtual classmates. There are opportunities for celebrities to interact with students, but nothing is put in the contract to make the instructors give back.

The Cut’s Sangeeta Singh-Kurtz was also curious about the quality of a Masterclass course, and so she actually signed up for and took the one offered by Vogue editor Anna Wintour on “how to be a boss.” I wasn’t surprised to learn from reading Singh-Kurtz’s piece that the course didn’t contain anything that couldn’t be found from your average entrepreneurship channel on YouTube:

The advice was banal (“Don’t micromanage,” “Be daring and take risks,” “Have a broad range of experience”), and the accompanying PDF workbook is much the same, with 35 pages of leadership and success boilerplate lifted from a corporate-retreat handbook …

… I wanted this class to live up to the potential it promised: to give me and other hungry, ambitious young women a real shot at learning something from one of the only women of her standing in media. But what we get, like Wintour’s previous ventures in authenticity, is a highly produced branding exercise that serves only to further the mythmaking around her.

While Wintour has enough star power that her course will likely sell just fine, regardless of content quality, I think this speaks to some of the weaknesses of the online courses industry at large. For many content creators, selling an online course has a certain appeal: instead of trying to get a thousand people to pay you $10 a month, you can just package a self-contained course and sell it for hundreds of dollars. That way, you can convert far fewer customers, and the course, if successful, can become a passive source of income. I’ve heard stories of people who supposedly set up well-designed sales funnels and then traveled the world while their courses generated six figures in revenue. 

But here’s the thing: how many people out there have the depth of knowledge and commitment to build out a course that’s actually worth paying so much money for? I think there are a lot of lifestyle and business “gurus” who’d like to slap together the same milquetoast advice Wintour offers and start generating income.

A great example of someone who got the online course model right is Ben Collins, who I had on for an episode of my podcast. Collins launched a niche blog based on his highlighly technical skill: using Google Sheets. He built up an audience around this blog and then developed a series of courses that taught one how to carry out extremely advanced tasks on Google Sheets. The course is well worth the price for any business owner who manages their books on the Google Sheets platform. Back when I interviewed him, Collins was generating $80,000 a year in income through his courses. I’m sure it’s much more now.

But can most of us become a Ben Collins? For all my expertise that I display in this newsletter, I don’t know that I could package it into a single course that someone would want to pay for. And so I can’t help but wonder if we’re in an online courses bubble, one in which a lot of consumers are left feeling unsatisfied with what they paid good money for. In other words, I don’t think Masterclass is actually worth $800 million.  

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Other news

The rise of Twitch grifters. [link]

An interesting look at the behind-the-scenes people who manage famous YouTubers' careers. [link]

The biggest thing this article about how “Joe Rogan got ripped off” overlooks is that it can be quite nice to let a middleman cut you a nice big check just so you can be rich and focus on doing what you love: creating great content. [link]

Is this the first example of New York Times writer decamping to Substack? [link]

"Ms. Atkin, who is 11th on Substack’s ranking of paid newsletters ... said she was on track to gross $175,000 this year from more than 2,500 subscribers." So we know there are at least 10 Substack publications generating north of $175k. Good to know. [link]

Great article about how my friend Jaclyn Schiff created a niche business out of converting podcast episodes into web articles. I remember when she first told me about it and I knew instantly that the idea was brilliant. [link]

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on TwitterFacebook, or LinkedIn. Email him at For a full bio, go here.

Creative Commons image via Pxhere