When Richard Rushfield launched The Ankler in 2016, the media professionals he spoke to told him it was a terrible idea. Nobody was going to pay for a newsletter, they said. He pitched the concept — an insider’s guide to Hollywood, all delivered via email — to every trade publication he could think of. Had one offered even $1,000 per month to write for them, he probably would have said yes.
Instead, he went solo, and nearly a decade later, The Ankler has become one of the most successful outlets covering the entertainment business. Though Rushfield did not disclose revenue numbers to Inbox Collective, one website that tracks Substack’s data, Substats, estimated their subscription revenue at more than $1.9 million per year. But that’s just a fraction of their overall revenue. Advertising and events are big moneymakers for The Ankler — in 2024, they were reportedly on pace to break $10 million per year in revenue.
What began as a one-man column has grown, under the partnership of Rushfield and former Hollywood Reporter editor-in-chief Janice Min, into a full-fledged media company. Min became co-owner and CEO of Ankler Media in early 2022, with The Ankler becoming the flagship title in a network of subscription newsletters, podcasts, and events focused on the entertainment industry’s business and technology. Min told TheWrap at the time. “I was an Ankler addict first — and then became dazzled by its list of subscribers, a real who’s who of power in entertainment.”
Ankler Media now publishes over a dozen newsletters, including their daily briefing, Wakeup; Series Business, which reports on TV industry’s big names and bigger shifts; and Prestige Junkie, covering awards and cultural influence. They have about 20 employees, plus contributors across the globe. The company has been profitable since year one, with its subscriber base up 13 percent year over year — and some of its fastest growth coming in 2026 alone.
That growth has now brought the company to a new inflection point. Requiring advertising technology that went beyond what their old platform offers, April 2026, The Ankler moved off Substack onto its own independent platform. Its new owned-and-operated site and subscription infrastructure is powered by Passport, a product from Automattic and Ben Thompson of Stratechery. The move, as Min and Rushfield wrote in their announcement, reflects a broader shift in their ambitions. “If the first wave of newsletters in media was about supporting independent creators,” they said, “the next wave is about building durable businesses.”
Not many newsletter operators will end up with a partner with Janice Min’s résumé, or the particular cultural moment that made Hollywood insider analysis a hot commodity. But the arc of The Ankler’s story is full of lessons that translate to any newsletter builder trying to build something authentic and grow it to be sustainable.
A few things stand out from talking with Rushfield about his journey:
For one, original growth was built entirely on independence. The Ankler’s earliest traction came from saying plainly what everyone in the entertainment industry already knew but wasn’t seeing written down anywhere — largely because the trades were too entangled with the sources and advertisers they depended on. That independence, more than any tactic or strategy, was the product.
The business itself was built on small, honest thresholds rather than ambitious projections. Rushfield kept the newsletter free for nine months, relied on word-of-mouth for growth, and only put up a paywall once he had 2,000 free signups, with a target of converting 10% of readers to paid. (Rushfield said they exceeded that target.) At the start, there was no growth deck or investor pitch.
When it came time to build the team, Rushfield found a partner whose instincts ran in exactly the opposite direction from his own. He is candid about the fact that his natural impulse is to alienate his audience and make the product as unattractive to success as possible (his words!) — not the best foundation for a business. The division of labor with Min wasn’t just logistical; it was psychological. Each of them could do what they were actually good at.
And even now, with a scaled operation behind him, and with Min handling the general editorial oversight of the spinoffs, Rushfield still carves out space for things he’s doing purely for pleasure. He launched a side project, the the freewheeling Rushfield Jamboree, to cover everything from books to Gen X liberation to relationship advice. (It’s free on Substack and separate from The Ankler’s lineup of newsletters.)
How did Rushfield navigate some of the big decisions over the past decade? I sat down with him to talk through the arc of The Ankler’s journey, from the cobbled-together early days to how he still remains scrappy and experimental. Here’s how he’s built this media company and handled the big moments along the way — in his own words.
(This transcript has been edited and condensed for clarity.)
When do you know it’s time to go independent?
Rushfield’s worked all across the web: Gawker, BuzzFeed, Yahoo, the Daily Beast. But years before subscriber-only newsletter products became commonplace and “Substack” a household name, Rushfield decided to launch his own venture called The Ankler. (The term “to ankle” is an old industry term used by Variety, meant to imply either quitting or being terminated from a job.) The launch was met with skepticism from friends and colleagues.
It was the time of the constant pivot to video, and everyone was still trying to figure out how to chase this dream that we could have revenue to rival what print publications made — if we just added the Google keywords, then all of a sudden we’d be like the New York Herald in 1943 or whatever. A lot of pivots.
My last stop was a site called HitFix, which I edited. It was a consumer entertainment news site — kind of like [Entertainment Weekly], but it had a few very notable critics, including Drew McWeeny, Alan Sepinwall, and Dan Fienberg. It was a very talented group, but it was a very challenging time to grow revenue for a website. You needed tens of millions of users every month just to keep your head above water against the declining Google ad dollar. They ended up being acquired by a company that basically folded in HitFix’s numbers to make it look like they had a big leap in audience, raised money off that news, and then shut HitFix down — all within 90 days.
After that, I said, “I’m not going to do another one of these.” And that was what led to me going out on my own.
I used Mailchimp as the basic CMS, which wasn’t really made for individual writers, but that was the best there was. Then you had to have a payment service, which was Stripe, and then a list management service that linked them together, and none of those things were really meant to speak to each other. You also had to handle your own security and site hosting and make all of that connect. About half my time was basic tech maintenance, which I’m not at all good at. It was a real schlep.
The first [newsletter] I sent to like five friends and said, “Take a look at this and tell me if you think it’s any good.” Then in the second one, I added maybe five more people and said the same thing, and said, “Please keep this secret.” Then I think after some point, when we were maybe 40 people, I said, “If you like it, feel free to pass it on.” And then it just kind of started growing.
When I was just starting out, it was kind of the height of mindless Netflix boosterism. Netflix would put out these statements like, “Our new movie was the fifth most-watched in North America for a Tuesday premiere,” or whatever, and every trade would just run that uncritically. I think it was that everyone was so in the tank that a lot of people in the industry felt like they were being gaslit and going crazy. So me saying, “Hey, wait a second — is that really what this is?” resonated. I’ve said that I could have renamed The Ankler “The Netflix Gazette” and it probably would have done even better, because there was such hunger for people in this industry to hear something else.
How do you know when to turn on a paid subscription?
Rushfield didn’t immediately start to monetize the newsletter. The first few months were spent building an audience, establishing the brand, and trying to figure out if there was a path forward for The Ankler as a full-time gig. In summer 2019, after meeting Substack co-founders Hamish McKenzie and Chris Best through the Information Accelerator, Rushfield eventually moved to Substack, becoming an early, prominent writer on the platform. His success was proof that talented writers could make a living through a newsletter, and others quickly followed that example.
When I started, every media professional and genius I talked to told me it was a terrible idea and that I shouldn’t do it. I don’t think there was a single person who said, “Oh, that sounds like fun — I could see that working.” Certain friends begged me not to do it. The common thing was “Okay, you’re a good writer, whatever, but nobody’s going to pay for an email. That’s just not going to happen.”
I had pitched it to every trade publication before I started, and really, if any one of them had been willing to pay me $1,000 a month to do it, I would have done it for them. But no one was even a little bit interested in having that conversation.
So I applied to teaching school. I thought, “This is very unlikely to work out, and I’m not going to go work for another screwed-up media company, so I’ll become a teacher.” And I was accepted, despite my Hampshire College transcript. I was waiting for teaching school to start, which I think was about six months away, and I did this in the meantime. When the six months came, it was doing well enough that I said I needed to see this through a little more, so let me defer for a semester. And then that semester came, and I deferred one more. I think I did four deferments before I finally said, “I think this is the thing I’m doing for a stretch here.”
When I launched, I had this idea — and I still think it’s true — that if you put up the paywall immediately, your readers are your marketers, and your growth depends on people passing things along. At least that was true in those days. So if you only have, say, 100 readers and you’re charging for it, you’re essentially dead in the water, because you only have 100 people who can market it — unless you’re a celebrity who can draw attention from outside or have some massive following elsewhere. I said I was going to keep it free until I reached a certain number of free signups, and then put up the paywall. That was about nine months. I brought down the paywall when I had 2,000 free signups, with the thought that if 10% of them come aboard, that’s enough to give me a little gas in the tank to keep it going. That was what I was shooting for, and it turned out to be much better than 10%.
How do you find the right partners and support systems?
Rushfield first met Janice Min when they were seated together at the press table at the Golden Globes in the early 2010’s. She had worked previously in top roles at Us Weekly and the Hollywood Reporter, and was well-respected in the industry. (Reporting on her departure at the Reporter in 2017, the New York Times said she’d “orchestrated a stunning turnaround” at the publication.) Her arrival at The Ankler changed the trajectory of the business.
By that point, most of the companies that had said no to me in the first place had come back and said, “Hey, we should do something together.” Most of that consisted of “Why don’t you give us everything you’re about to print and it’ll be great exposure for you to be in our publication for free.” So there were other things floating around, but none of them were particularly tempting.
Janice came to me with the notion of building something together, and frankly, I didn’t actually think she was going to throw her lot in with some guy’s email. We would talk about it every week or so. She was looking for what she was going to do next. I enjoyed our talks very much, and I thought she had a great vision for it. I didn’t actually believe it was going to happen — it seemed too big. And then one day she said, “I’m ready to do it.” There was about a year of conversations leading up to that.
The basic idea was that I would keep being a columnist, and she would build a larger thing around it. In reality, when you’re building something and starting a new business, it’s kind of all hands on deck.
Something Y Combinator really beat into our heads: They demanded that on everything, you had to name the one person in charge. It can’t be both of you. They said, “You will have conflict if you don’t spell that out from the beginning.”
[When you bring on a partner, you want to] work with someone who has a vision you’re comfortable with and where you share a basic sense of what the thing could be, but who has different skills. If you’re both good at the same things, you’re also both going to be bad at the same things, and that leaves a big gap. First, you have to be aligned on what this is and where it can go, or you’re going to have lots of problems. And just know, at any moment, who is in charge of what. Don’t have ambiguity about it. Have all the hard conversations upfront.
Just after we launched, we applied to and got into Y Combinator [in January 2022], which is a very intensive program where you get real business training. It’s like business school in three months, but you’re running your business at the same time, and you’re expected to basically grow by 10% every week while you’re doing it. You spend the mornings in seminars and workshops, and then in the afternoon you have to go run your business. And I also had two very young children at the time. It was an intense few months, to say the least.
Before we got to demo day, our Y Combinator advisors said. “You guys are already profitable and growing — you don’t really need money, so you probably shouldn’t raise very much, because then you’re giving away a piece of your business.” So we were only actually raising a little bit to give us a cushion in case we had a bad month or something. But it was a great education. I learned a ton, and it’s really guided us ever since.
When and where should you expand your business?
Over the next few years, the rebranded version of The Ankler, now called Ankler Media, really started to grow. They raised $500,000 from Y Combinator, and then another $1.5 million in June 2022. Their company was valued at $20 million, per Pitchbook data. They reinvested that money back into the business, adding staff, building out their live events business, and becoming one of the go-to sources for news about Hollywood.
When you’re starting a business, there are all kinds of ways you can grow. You can grow subscribers, signups, revenue — and it really focused on what the one metric was that mattered. For us, that was growing the subscriber base while staying profitable. So it was all about what we could add that would bring in new subscribers. We tried a lot of things — other writers, freelance features, different verticals.
Basically, the result was that we just started publishing a lot more. It went from me publishing twice a week to, very soon, publishing twice a day with different things. And obviously, I couldn’t write all that, so we started bringing on other writers.
They say the hardest point in a business is between when you have one and seven employees, because you’re growing, but there aren’t a lot of people to handle everything. You’ve got to start thinking about taxes, and healthcare, and payroll, and who’s handling the tech stuff — and there’s not yet enough people to do all of that, but there’s a lot of growth in income. It’s kind of chaos and a free-for-all until you get to the point where people are in defined roles.
For me, the importance was always the integrity of what I wrote and what had my own name on it. That’s always been — because I’m an egomaniac — what really matters to me, more than The Ankler name. And there was never any question about that. Nobody was saying, “Why don’t you start doing red carpet coverage?” I was still doing what I wanted to do, driven by my own interests. Still am. Having a bigger business built around that was nothing but good for me.
Being a member of Gen X, my natural instinct is: how do I alienate my audience and push away as many people as I can, and make this product as unattractive and unpalatable to any kind of success as possible? I recognize that if you’re going to grow a business, that’s not the best instinct. I understood what we had to do, and there was no one better than Janice to do that. My instinct to make our readers feel uncomfortable and ashamed of themselves is, you know, hard to build a business around.
It’s really driven by talent. We have a hundred ideas for “a newsletter about this would be good,” but the person who can actually do it has to know everything about that field and they can’t just write about it like everyone else who writes about it. They have to have the knowledge of a reporter who comes from it, but they also have to have a voice. They can’t just be a beat reporter, because there are already those, so why would anyone pay for it? And they also have to have an entrepreneurial spirit about growing it and maintaining their independence.
That’s a hard combination. When you’re trying to figure out who will be successful, it’s the people who have all of those qualities. And that is not everybody.
What worked with The Ankler — and why?
So much of The Ankler’s success has been about finding what other industry publications were doing — and then doing the opposite. When others were investing heavily in algorithmic channels, like social media, The Ankler built around email. While other trade publications bombarded their readers with emails from sponsors, The Ankler built partnerships that resonated with their audience. Even Rushfield’s new video series, Rushfield Lunch, came from identifying something missing in the public discourse. He was frustrated that good industry conversations, like a recent chat with legendary comedy writer Bruce Vilanch, were disappearing without a public record. The series, much like the earliest Ankler newsletters, was designed to fill that gap.
You know, I think the newsletter medium actually forces something important in you. When you’re writing for these websites — which is what the trade publications have become — you do so much stuff for reasons other than the readers. You’re doing it to make a source happy, for SEO, because of a partnership, because someone promised something to someone. And you just get deluged by it. In the list of who you’re thinking about, your core readers just sink down to, like, the 20th spot. You look at those sites, and there’s so much content that’s not really written to be read by anybody, except maybe one person you made some promise to.
The thing about newsletters is that when you’re on one stream with one newsletter, everything is on center stage. Everything is in the center ring. There are no throwaways. You can do sponsored emails, and we do, but that better be way less than what’s important — way, way less. Because if that’s how people start thinking of you, you’re dead. Everything you do has to rise to the level of: Should our readers stop their day to look at this?
For me, everything starts as “I’m doing it for fun.” If it begins with “I see a money-making opportunity,” it always fails. With the Rushfield Lunch, I spend a lot of time talking to really smart people about the industry, and much of what I write is kind of recycling and filtering the wisdom they gave me. I just kept wishing I could share these conversations in their unfiltered form with the public. I think that was the impetus to start doing those.
I’ve decided that rather than being religious about interviewing someone every week, I’d rather wait for the right guest. If that means four a month, great. If it means one a month, maintaining quality is more important than filling a time slot.
I interviewed an acrobat at Cirque du Soleil in Las Vegas many years ago. She did amazing flips a thousand feet in the air, and I asked her. “Aren’t you terrified doing that without a net?” She said. “Well, this is what we do. We practice for it and we train for it, so we know how to do this. But the danger isn’t that we don’t know what we’re doing up there — it’s that if it gets too routine, you get bored, and then your mind wanders for a millisecond. And in that millisecond, you might miss grabbing the person’s hands. So you have to continually make it harder. You have to be scared all the time.”
The fear is what keeps you alert — otherwise, you’ll die. That’s the metaphor that’s guided my life.
