4 Comments

Simon, you've got a great newsletter here. As a substack writer myself (I think I'm lower class lol) who is experimenting with selling some sponsorships (I charge way more than typical ads) and I am thinking about going the paid subscriber route I do see a lot of these problems you describe. Selling sponsorships is additional work. I'm not 100% sure it's worth it. It's nice to have a bit of side income early on, but it's also annoying to have to cold email people, follow up, and get rejected.

One thing I think we forget is that people like Casey Newton had a free newsletter for 5+ years before he started doing substack. The same is true of other successful writers here that might have had careers as journalists just grinding it out. If you are a new newsletter writer the idea of working on something for peanuts for 5+ years as a side hustle seems crazy. It's what I'm doing and I'm in year 2 (hopefully breaking 1000 free sign-ups by June).

I think perhaps I'm just getting to a point where I'd feel comfortable doing a paid version. Maybe in the next few months.

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Great article. Thank you so much for sharing. Through my experience of writing on Substack over the past few months, I could relate to everything you said, and I agree that even if it is challenging, it is eventually possible, and definitely an enjoyable process, for me at least, it is the work portion of my day that I look forward the most.

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As a middle-class newsletter writer myself (I write L'Économiste Sceptique, a French-speaking newsletter popularizing economics: https://www.ecosceptique.com), I agree with a lot of what you wrote. Or at least, I have a very similar experience myself. The difficulty of A/B testing and collecting data on what works and what doesn't. The harsh learning curve of “marketing” when you start — regularity over quality. How you need to carefully plan the financials. And so on.

That being said, I also agree that in the middle run, building a sustainable newsletter is definitely possible.

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A lot of what you wrote resonated with me. You put it down so well, Simon.

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