How Richard Rushfield founded one of Hollywood’s most influential newsletters

Richard wrote the newsletter in a raw, unfiltered voice; he was an insider who wasn’t afraid to ruffle feathers.

By the time Richard Rushfield launched his newsletter The Ankler in 2017, he had held journalism jobs at several major media companies that included The Los Angeles Times, BuzzFeed, and Gawker. But because he served as a behind-the-scenes editor in most of these roles, he didn’t have much of a personal brand to speak of, which meant he needed to build his newsletter readership from the ground up.

Despite these headwinds, Richard managed to replace his full-time salary within about two years, and The Ankler is now a must-read for virtually every Hollywood studio executive. In our interview, he explained how he built his audience and why he prefers his life as an independent writer much more than his past career as a traditional journalist.

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.

His introduction to Hollywood reporting

Long before he founded his newsletter, Richard covered the entertainment industry as both a reporter and editor, starting with the LA Times. “This was in the early 2000s, I think about 2002. They had had a very rudimentary website, but it had been largely behind a paywall.” He was hired as a part of a team charged with building editorial products for the website, and he eventually migrated to writing about Hollywood. “At the time American Idol was in its sixth season, so it was the biggest show on TV. Through the LA Times. I was able to go and attend the tapings and hang around the set and talk to people. And I became very interested in just seeing what went into producing two live shows a week for a giant audience. I spent three years going to every taping of it. I did profiles of the makeup artist, the lighting guy, the lawyers, the producers, the stage manager. And I just got to learn about all the elements that go into creating such a production, and it really made me appreciate the craftsmanship and the decisions that go into something like that.”

After Richard left The LA Times in 2009, he went on to edit the entertainment verticals of several prominent websites including Gawker, BuzzFeed, and Yahoo News. While he enjoyed the freedom that came with writing for these media upstarts, the economics of digital publishing began to wear on him. “The idea for how to make a website pay was through programmatic ads and Facebook ads and Google ads, and sites needed to have so many millions of people come to them every month to just break even, even with a skeleton crew. It became just this game of clickbait and optimizing your Facebook pages and all this other stuff that was about anything other than just doing good quality work. And there was no longer this concept of building an audience and having a loyal readership that was with you on a journey. It was just about grabbing people with a headline, any way you can. It was not a satisfying way to be living as a writer.”

Launching a newsletter

Richard launched The Ankler in 2017, a few years before Substack had normalized the idea that a newsletter career was possible. Unlike other journalists who took this path, he didn’t have much of an online brand to speak of. “I had mostly been an editor for the 10 years previous to that, which means you're mostly invisible to everybody, so I didn't have any following at all. I just saw that there was this opportunity to do something in entertainment coverage that was more interesting.” He figured that if he could just find 2,000 people in the entertainment industry who found his content interesting, then they’d pay for it.  

Richard started with a soft launch of the newsletter, only sending it to a few close friends. “When I started off, I was just writing reviews of whatever I watched on TV last night. It was kind of all over the place. I took a while to find my voice, and I knew I wasn't ready to launch this as a product yet. So the first week I sent it to five friends and asked them to tell me what they thought of it. And then I added five more the next week, and then five more the week after that.” Once the list reached about 50 people, he finally opened the newsletter to the public.

Richard wrote the newsletter in a raw, unfiltered voice; he was an insider who wasn’t afraid to ruffle feathers. “As it took off, people started reaching out to me and giving me their insight about what was happening, how I should look at certain stories that were breaking, and how the industry was evolving. When I started doing this, I knew more about the issue than the average person, but there was still a lot I didn't know, and I feel like this newsletter has kind of been the education of Richard Rushfield — me going away and learning about the industry and what really matters and asking the stupid questions and finding it out. And there have been a lot of people that talked to me and kind of led me through that process.”

Monetizing the newsletter

About nine months after Richard launched The Ankler, he rolled out a paid version. “When I launched, you had to cobble together several tools. The newsletter was sent through Mailchimp, it was a Wordpress site, and then I had Stripe to process the payments. None of those things connected well, and I know just enough about tech to be very dangerous to myself and think I can fix all these problems, which just led to all sorts of nightmares and crashes. It was a real Frankenstein's monster for the first year and a half or so.” Eventually, he learned about Substack, which streamlined all of these processes. “When I moved to Substack it was all just seamless.” 

Richard’s newsletter output fluctuated over time. “Pre COVID I was doing two or three emails a week, and I would make one of them free.” For the paid newsletters, he’d send out “preview” issues to the entire list that would allow non-subscribers to sample the first few paragraphs. Subscribers had the option of paying $10 a month or $100 a year. 

Because he didn’t have a large personal brand to start with, his subscription growth was gradual. “The only thing that the business has to sustain is my family. I don't have any other employees or offices or anything. So its measure of success was: is this enough for me to live on? And I'd say by year one, it was halfway there, and by year two it was enough to live on.”

At the end of our conversation, I asked Richard if he’d ever consider taking another job in traditional media. “I've been really happy over the last three years that I've been doing this. They’ve been the most rewarding of my career, because I'm writing what I want to write. I feel like I'm doing my best work. The great thing about a newsletter is I'm not thinking about anyone but the readers, I'm not thinking about SEO or how this fits in with a larger publication or whether this will get us in trouble. I just don’t have any of that. ”

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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 simonowens@gmail.com. For a full bio, go here.