My Three Biggest Substack Failures

I found great success on Substack, but I've had some major failures along the way.

Every now and then, I write about writing. I don’t like to do this very often because I’m afraid it might veer into LinkedIn-style posting, which is the last thing anyone wants. But given that people frequently ask me questions about Substack and the success I’ve found here as the #1 humor publication, I might as well share the other side of things: the things I did on Substack that turned out to lose money. And in the spirit of losing money, I’m making this article free (typically my 5x/week articles are paid).

Anyway, here are the biggest disasters of my Substack career so far. I acknowledge it’s important to write what you want, and not be completely beholden to audience capture, but this is my sole source of income. I have to be realistic if something isn’t working out. A good way to tell that something isn’t working out is if I lose money on it, and bleed paid subscribers (especially if it happens time and time again) so that’s my primary metric.

My “Book”

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I’ve tried publishing books several times in the past. I was professionally published before I was CHH (it didn’t go well, I wrote about that here). Part of the problem was that I wrote my book when I was twenty-five and part of the problem was that I had no “network” to promote it and my agent didn’t really do anything. But I tried self-publishing too, which also didn’t go well. When Substack started out going well for me, I thought I might try a more unorthodox avenue for publishing my next book: every chapter as a separate “article.” Last year, I published my Substack “book,” Will There Be Free Food?, which I can best describe as David Sedaris-adjacent (I wish) humorous memoirs about my awkward twenties in the San Francisco tech world. You can still find all the chapters (and some extra ones) here.

But this was a major miss—perhaps my biggest miss of all. Not because the book was badly-written (I actually still think it’s some of the better stuff I’ve written) but because of how I organized and published it. Not everyone got the heads up about the recurring chapters, which actually didn’t need to be part of a book, because each chapter was a completely separate story. These chapters could have easily been published as standalone personal essays, with more descriptive titles. My choice to put the word “Chapter” at the beginning of each story meant that people who were new to these essays felt out of the loop and didn’t click, figuring they would need to read the rest first. I had a feeling this was a problem early on, but I felt like I had to keep going or it would be too embarrassing.

The Sublet Caper was one of my funniest chapters—it’s a personal essay about how my husband and I cooked up a bunch of pencil-headed schemes to obtain affordable housing in San Francisco, culminating in a kicked-down door among other hijinks. But because it was “Chapter 10” of my book, very few people read it. I gained two paid subscribers, lost nine, and I only got 56 likes, which even at the time was low for me.

Part of the problem wasn’t just that it was a chapter but that the title wasn’t descriptive enough. Let’s contrast that with a personal essay that had a more descriptive title and was presented as a standalone personal essay: I was Extorted By My Neighbors for $2000. Even though these were published relatively close to each other, I gained 88 paid subscribers from this personal essay. I also lost a lot—39! But the ROI was clearly there. I also gained 72 free subscribers, and had more than twice the likes. I actually don’t think this one was funnier or better-written than The Sublet Caper. It was just dumb of me to try and present these essays like books.

I might publish another book in the future, but it’ll be either through a real publishing house or Amazon, not as recurring chapters on Substack.

My Podcast

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This one pains me because I had so much fun doing my podcast! It was the only way to get my brother to agree to talk to me for an hour and a half. For the record, I still stand by my podcast episodes. I think they were really funny and I think you should still listen to them. But they lost me way more time and money than they made, with little explanation.

First of all, I could only do my podcast interviews at night, so they cut into my only time alone with my husband. Because I watch my toddler during the day, and because my podcast interviews typically went for 1-2 hours, it would have been risky to schedule them during the day, even during her nap which can often be cut short. So while you can’t put a price on time with your spouse, I had to keep in mind that every time I recorded an episode I would definitely not be getting laid, and my husband would be irritated that I screwed up his anti-insomnia routine by going to bed after him.

Perhaps I gave up too soon, but just as an example, the aforementioned (paid) episode with my brother gained me seven paid subscribers. Great, right? Not so great, because I lost seventeen. You might think that’s because my brother is (no offense to him) a total nobody. So what about the famous and genuinely talented Noah Smith and Matt Yglesias? I had them both on, and I still think those episodes were awesome! I’m still honored either of them agreed to talk to me. I talked to Noah Smith about sex and Matt Yglesias about parenting, and I was so excited to be doing the whole “talking to serious pundits about stuff they never discuss” theme. The Noah Smith episode was my first one ever, and it was free. I gained one paid subscriber, and lost fourteen. My Matt Yglesias episode was paid, so I gained 63 paid subscribers (that’s right—major banger) but I lost 42! Also, keep in mind that a great deal of the paid subscribers were people taking advantage of a free trial solely to listen to that one episode, so I probably lost a bunch of those a week later. And as great as that episode was, it would be pretty hard to get someone as famous as Matt Yglesias every week. I was thinking the podcast format might be the problem, because my interview with Will Stancil had gone well in article form. But alas, even though I gained twenty-two paid subscribers from that interview, I lost just as many!

These episodes also took at least an hour to edit (I left the Noah Smith one unedited, and got feedback that I needed to edit and normalize sound, so I did that going forward). When you combine the time it took to record them, plus the time it took to edit, they were way more time-consuming than writing my daily articles, which usually wind up acquiring more paid subscribers than they lose.

I don’t regret doing these episodes, because they were super fun, and people enjoyed them. I had a few others lined up, and I was really excited about those too. But the ROI just wasn’t there so I didn’t move forward with recording them. Maybe I needed to keep going, maybe I needed to make them all paid (or all free? I don’t know) but the revenue impact didn’t make sense for the time it took to do them.

Satire/Trolling

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Technically I run a humor Substack, and some people get confused about that because not all my content is meant to be Comedy with a capital C. But I guess it’s all meant to be humorous, in the sense that even if you’re reading about debilitating OCD or the loneliness epidemic, the voice is one of a humorist. If you still don’t think it’s funny, that’s okay—some people just have terrible taste.

Sometimes, I have this feeling where I worry I’m not doing enough obvious humor content. So I try my hand at straight-up satire. Usually, I make these articles free because they’re not my usual milieu. And so far, it hasn’t gone well. I wrote an article (in the form of a fake guest post) from a grown man who was inordinately upset about woke princess movies, and it was one of my lowest-traffic articles of all time. I gained three paid subscribers and lost four. I wrote about how I need to be the next liberal Joe Rogan and lost fourteen paid subscribers. I also wrote a fake guest post from a self-pitying CEO talking about the emotional labor of getting his employees back into the office. Perhaps unsurprising, I lost more paid subscribers than I gained. Also, several people thought the post was real and “confusing.”

My most successful satire was I’ve Been Personally Victimized by MAGA Taylor Swift. I got over 400 likes on that article and 40 new free subscribers. But I still lost more paid subscribers than I gained—I gained 11 and lost 16. Given how many free subscribers I gained, I would still consider this article a success, but it’s probably not a format I’d repeat often. I also wrote about my former life as a Reddit troll, and this did a little bit better (it was in the early days of this Substack, so it’s hard to say) but this one had more of a personal essay format, which is more what people expect from me.

Note that losing 10+ paid subscribers on a post is completely normal for me—a lot of people unsubscribe because it’s toward the end of their free trial and it doesn’t really matter what article prompted them to do it because they were going to do it anyway. But the subscribers I lose need to be made up with new subscribers. So far, the satire articles have failed at this.

Honorable Mention

There’s another Substack failure of mine, but I refuse to stop doing it because it just gives me too much personal fulfillment, and that is my series of free Trump impressions. My best impression was probably my “Trump reacts to Elon Musk’s Epstein list accusation” one, which was the only one that actually made me money (and barely). I did another one where Trump is interviewed by Elmo about Taylor Swift, which performed more typically for these: I gained three paid subscribers and lost fourteen. Again, I’m aware a lot of the unsubscribes could be from people who were always planning to unsubscribe and this just reminded them, and I genuinely believe I am the best female Trump impersonator alive, but it’s clear these aren’t moneymakers for me. That’s okay though, I’ll still keep making that garbage.

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