How Jesse Singal built a 6-figure income through Patreon and Substack

He managed to take a large Twitter following and convert it into paying subscribers.

A year ago, Jesse Singal had a very traditional freelance writing career. When he wasn’t working on his book, he’d write articles for places like The Atlantic and New York magazine. The mixture of book advance and freelance revenue provided a reasonably stable income.

Today, the economic climate for journalism is much more dire. The Covid-induced recession has led to mass layoffs and a squeeze on freelancer budgets. Some publications have closed up shop completely. But in many ways, Jesse’s income streams are more secure than ever. That’s because he launched a paid newsletter through Substack and co-hosts a hit podcast that monetizes through Patreon. Together, these two sources generate a nice six-figure income for him.

I recently interviewed Jesse about why he decided to monetize his audience directly, how he designed his paid offerings, and whether he thinks platforms like Substack and Patreon can replace the income for laid-off and underemployed journalists.

To listen to the interview, subscribe to The Business of Content on your favorite podcast player. If you scroll down you’ll also find some transcribed highlights from the interview.

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This transcript has been edited for clarity.

On what motivated Jesse to launch a Substack account

Jesse had a pretty stable freelance career. He had his book advance and regular contract gigs at major media outlets. So why bother with a paid newsletter? The decision came after the founders of Substack reached out to him and encouraged him to join the platform. “I figured I have some free time. The freelance market does not look particularly sturdy, not because of reasons having to do with me, just because of structural reasons. So why not give it a shot? And it ended up working out for me, in part, because I arrived already having a large following.”

The newsletter started out completely free. “I do think one of my strengths as a writer is I can do the sort of breezy, bloggy, almost Gawkery style posts. And then I can also dig deep into a social science paper that I think is important and show lay people why it's important. If you look at the most successful Substack writers, they usually operate under a single theme or tone or style. I think I’m a little bit more all over the place. As with everything else I do, I cannot point to any particular strategy or forethought. I'm sure if I'd been a bit smarter, I would have written myself a memo. I would have predicted benchmarks and saw if I reached them. I didn't do any of that. It just sort of worked out from the hard work of writing, basically.”

As the freelance market continued to get shakier, Jesse began thinking of Substack as a way to diversify his revenue, and he eventually launched a paid version. Unlike most Substack writers, he now puts the bulk of his longform work behind the paywall. “I try to limit the free ones, especially now that I have a solid base of subscribers, but when I do a free one, I try to make it either a big sweeping argument that latches onto the present conversation, or I often just do these book giveaways, which are a good way to draw new eyes for the newsletter. Basically, if a book looks interesting to me and I feel like I'm unlikely to have time to cover it or sometimes even read it, I'll just ask the publisher for a few copies to give away on my newsletter. And I think I'm batting a thousand on that. They're always happy to. It's so brutal getting publicity for books that they're basically always happy to do it and I'm happy to do it.”

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Why he also launched a Patreon account

So if he was seeing so much success with Substack, why bother with another payment platform? In the beginning of the Covid-19 pandemic, his journalist friend Katie Herzog got furloughed from her job, and the two decided to launch a podcast called Blocked & Reported. “I think the goal was always to make money off it. We didn't really have a strategy. We decided to just launch it and see where it goes.” The success was almost instantaneous. “The beginning of June was just this huge inflection point. And then maybe a month after that, I started noticing that our first day download numbers had jumped by three or four times.”

Their Patreon strategy was pretty simple: you need to pay to access all their episodes. “Right now we're doing at least three paid episodes a month for our lowest tier. We always do one free weekly one on Monday morning. For those who pay $10 a month, every two months we do an ask us anything and we do a live video stream, both of which you get access to. And then for the $20 tier, the only other perk you get is we'll give you a shout out once a month, if you want one.” 

How this success affected his freelance career

Jesse is now generating a six figure income between Patreon and Substack. I asked him how this impacted his work for traditional media outlets. “I'm no longer going to do the quick column for a few hundred bucks. These days, even if you can get $300 for an online column, that's fairly generous. The point is there's a big segment of the freelance market that's collapsing anyway, but I basically don't have to deal with it, which is incredibly fortunate. There are a lot of outlets I still like to write for, especially ones that they can support you and give you travel money for reporting and pay you well. And I feel like I can still pitch those despite whatever controversy has gone on. And I think when the book comes out, it will maybe bring more reporting opportunities. But at the end of the day, this gives me a comfortable base of income and I can just write and it's very enjoyable.”

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on Twitter, Facebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.

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