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Newsletters: The Naughty and The Nice

2 min readNov 23, 2021

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Over the last two decades, new forms of media have waned in and out of popularity and favor. Now, in 2021, the fruit of a new venture takes front stage: the creator economy. Bloggers, vloggers, freelancers are our inspirational muses for their often humble beginnings and perceived authenticity.

One newer subsection of creators is that of newsletter writers, especially those congregated on the site Substack.

Huge success stories like The Morning Brew and Matt Taibbi are hugely appealing to both new and established creatives, especially to journalists and writers who want to break away from traditional paths.

But the road to newsletter success is not as easy as one would hope. Without a convertible following elsewhere (Twitter), it’s hard to devise a profitable income from running a newsletter alone. Striking the right balance of free versus paid content, mitigating burnout, and managing steady growth are all considerable obstacles when starting a newsletter. Not to mention that being one’s own boss comes with a plethora of other challenges.

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Many people enthralled by the fantasy of Substack success are drawn to the idea of living off of a steady income as a means to build their newsletter, where eventually the income brought home from their side venture will fully replace their office job. That line is not as clear as one would imagine. Especially when one considers that building a newsletter to that point would likely involve treating it as a full time occupation- even while it has no direct monetary output.

But not all is gloomy, like YouTube, many have struck a comfortable middle ground between content and revenue. The same is likely to happen for Substakkers.

Simon Owens, a successful blogger himself, phrased this group as Substacks middle class.

Some estimate that creators have collectively taken home about $20 billion in the last year (I ran through the math in this video). If you divide that by the median household income of $50,000, that means the creator economy supports upwards of 400,000 jobs

Of course, there are outliers on either end- but there finding a place in between is more than attainable given the right direction.

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