The Secrets Behind Assistants vs. Agents? Content, Community — and a Newsletter with Priceless Intel

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When Warner Bailey was working in the mailroom at WME, which has represented some of Hollywood’s biggest stars for more than a century, he and a few pals started an Instagram account called Assistants vs. Agents. It was 2018, and he just wanted to make his colleagues laugh and not feel so alone in the fast-changing, often-bewildering world of entertainment. 

But as the account grew — Bailey took it over himself shortly after launch — and generated some high-profile publicity in L.A., he leveraged his expertise, connections, and audience into a newsletter in 2023. Since then, as Bailey put it, “it has grown into a multi-faceted educational ecosystem” connecting and informing those breaking into or still getting their footing in the entertainment field. 

From that meme page, Bailey has built an entire business around a highly engaged niche: the young professionals who make up entertainment’s next generation. Today, that ecosystem includes:

• A newsletter
• A standalone job board
• Online summits
• Classes
• A book in development
• Branded events with some of Hollywood’s biggest studios

How’d he turn a single Instagram account into a diversified media property and educational platform, with newsletters as a core tenet? Let’s explore.

A meme page grows into a newsletter

Bailey spent years working behind the scenes in entertainment in Los Angeles— at WME, Live Nation, and in festival production — before launching the Assistants vs. Agents on Instagram. Witty, wry memes about Hollywood’s power dynamics struck a chord — the account reaches more than 150,000 followers today — and the attention of some of the industry’s biggest names. Typical takes cover how a boss’s summer email feels at 3 p.m. on a Friday (like Hello Kitty taking a sledgehammer to a laptop), what it’s like to go to work knowing that you passed on a script that’s up for an Oscar (a clown staring sadly at himself in the mirror), and how an industry superior typically replies when he’s informed that his laptop isn’t working due to a global outage (“Fix it.”) 

One moment in particular marked a turning point for the account. “Ari Emanuel had shared two of the memes that I posted,” Bailey said of the Endeavor CEO, one of Hollywood’s most powerful players. “He screenshotted the memes and shared them with the entire company worldwide.” Bailey said he woke up to 100 missed calls the following day. “That was a big moment where people were like, ‘Okay, this is read by more than just assistants.’”

Where AvA fits into the larger media landscape

Back in 2022, when Inbox Collective first published its guide to newsletter business models, we didn’t cover the overlap between the influencer world and what we were calling the “indie newsletter” world. The influencer world was all about attracting attention, most often on social media channels. The indie newsletter world — or the creator space, as it has become more commonly known — focused more on building a loyal audience, primarily through newsletters, and then monetizing through a variety of revenue strategies. These two worlds rarely intersected.

As his audience grew, Bailey began to see Assistants vs. Agents as more than a social media page designed to entertain. It was a community of people in the same professional boat. “There’s always been a taboo around asking questions you don’t understand,” he said. “I’m trying to eliminate that and say it’s totally okay to not understand this industry because it’s complex, it’s fragmented, it’s changing.”

In shifting the focus of Assistants vs. Agents — less about sharing inside jokes about Hollywood, more about creating the go-to brand for anyone trying to build a career in the industry — he bridged the influencer space and a creator model. The new version of Assistants vs. Agents would be a larger brand, monetized in multiple ways, with a newsletter serving as the link between the memes and the professional content.

Launching The AvA Connection

The inbox is still the professional hub for most industries, so adding a newsletter as a core pillar of the brand made sense. In 2022, Bailey launched The AvA Connection to build community for people working behind the scenes in Hollywood.Bailey had answered the big questions that anyone needs to answer before launching a newsletter:

• He knew who he was building a newsletter for (assistants in Hollywood) and why they needed his help (to get ahead in their careers).
• He had expertise in the space, which meant that he had insights this audience would value in a newsletter.
• He knew that this audience wasn’t being served by other Hollywood publications.
• And he already had an existing audience base on Instagram that he could market to.

The AvA Connection publishes three times a week. Industry news goes out on Monday, the job board publishes on Wednesday, and an interview comes out on Fridays. The core audience:  Hollywood assistants, coordinators, junior executives, and students looking to break into the industry and get practical advice about how to grow their careers,

That Friday series features conversations with high-level figures like the head of music at the NFL, the head of editorial at Spotify, and partners from UTA and WME. “The throughline of it all is approachability,” Bailey said. “I hope through AvA, people feel more comfortable that they’re not alone in struggling to understand the industry.”

Today, the newsletter has over 33,000 subscribers and a 68% open rate. Growth has been organic — and intentional. Bailey’s strategy has never relied on paid ads. Instead, he’s met his audience where they are. “I’ll post on my personal LinkedIn, ‘Hey, we just published these jobs,’” he said. “We’ll get like 500 people dropping their emails below each Wednesday. I also go into Reddit groups, Discord, WhatsApp, Slack. I’ve spent $0 ever on advertising anything that I’ve done.”

Building the flywheel

Around the same time that the newsletter launched, an article in Variety heralded Bailey’s coming out as the man behind the Instagram account. He realized his newsletter had the potential to be the foundation for a much larger ecosystem of educational and career tools. “When I publicly showcased that it was me behind the account, I got thousands of people reaching out — with ideas, or even just simple messages saying, ‘Thanks, this helped me secure a job,’” he said.  

The growth of the newsletter unfolded naturally, through conversations and listening to what the audience wanted. The newsletter began as a series of interviews that began with Bailey’s own network. “I made it a New Year’s resolution two years ago to reach out to one person each week that I admire from the industry,” he said. “I started small through my close circle, people I’ve worked with, and then it started expanding to people like the head of music the NFL.” 

Bailey also realized that a large portion of his audience was college students looking to break into the industry, and they had many questions about how the business worked. Capitalizing on this, he leveraged students’ appetite for information and connection into a series of talks at college campuses, including Georgetown University and the University of Michigan.  

This expansion inspired Bailey to start building a team to support AvA. That team, now six people and growing, is building out multiple ventures, including:

• The AvA Job Board, connecting early-career professionals with vetted roles at major entertainment companies.
• Virtual summits and university partnerships that scale Bailey’s one-on-one mentorship model.
• Educational classes and an upcoming book designed to update the “industry bibles” for a new generation.
• Forthcoming social-first short form series, tech and a scripted series expanding AvA’s reach beyond email.

Each piece feeds the next — what Bailey calls a “flywheel of content, community, and infrastructure.”

One of Bailey’s favorite stories from AvA’s organic expansion came from an email out of the blue. “A student named Dominik [Sansevere] from Cornell reached out to me and said, ‘All my friends read the publication. I have some ideas for you,’” Bailey said. “He broke down and built me essentially a mini business plan on how I should execute it. I hired him on the spot.”

Dominik now helps run the new job board, and Bailey takes pleasure in rewarding his hustle: “It’s very rare that someone will take the initiative and do that. He’s been an incredible person that I’m excited to bring along the journey.”

Bailey’s emphasis on collaboration is intentional, focused on building a team where everyone adds something, and not just growing for growth’s sake. “I built it alone for the first six years, and once I started bringing people in, that’s when it started scaling,” he said. “I just want to surround myself with people who are smarter than me or experts.”

Monetization to fuel expansion

Despite the scale of Assistants vs. Agents, Bailey remains cautious about how he monetizes. “I really do my best not to charge the end user,” he said. “Most of our revenue is brand oriented.”

Partnerships with Netflix, Apple TV+, and Paramount+ have helped fund AvA’s events and activations — from digital campaigns, film screenings, and panels to large-scale networking events. “For Netflix, we screened [the 2024 film] ‘A Family Affair’ with Joey King, and they brought out about 300 assistants to their campus,” Bailey said. “For them, it’s promotion and alignment with our community, but also an opportunity for assistants that they’re not getting elsewhere.” 

The events, now under the branding Ava IRL, are “scaling immensely,” Bailey said, with 20 sold-out events in 15 cities in 2025. Some have had more than 600 guests show up to network and listen to top names in entertainment share their expertise. In November, AvA hosted happy hours in nine cities. Tomorrow night, he’s hosting the first-ever AvA Awards, highlighting assistants who’ve done great work in Hollywood. He’s expecting more than 450 people to attend.

The job board also represents a major revenue stream, with companies paying to post listings. (A featured listing, including promotion in the newsletter and on LinkedIn, costs $400.) And as AvA has evolved onto multiple platforms, Bailey plans to develop more products and technology designed to make job hunting and networking more effective — and more human, like the man behind the memes. One example: He’s created an interview guide to help first-timers through the job interview process.

And there’s even an AvA merch store now, highlighting memes and jokes that fit right in on the Instagram page. In Hollywood, an actor or band that suddenly rises to stardom without organic support — often because of behind-the-scenes connections or nepotism — is known as an industry plant. Naturally, you can buy a desk plant — your personal industry plant — for $39. Or treat yourself to a mug reading “This meeting could’ve been a text.” 

Ultimately, Bailey sees Assistants vs. Agents not just as a brand, but as a bridge. “My goal with AvA is to capture a highly valuable niche that’s been overlooked for a long time,” he said. “Access is the hardest part of entertainment, and I want to make people feel like they belong in this industry.”

There have been full-circle moments, too. Bailey was working for a talent agency when he launched a meme account about how to break into Hollywood. It got big enough that he left his big Hollywood job to focus on building a business around it. And in December, Variety reported that he’d signed with United Talent Agency to help him further scale this business. So yes: Bailey left his agency job to create a business about how to break into the agency world — and ended up signing with one of the biggest agencies in Hollywood.

Six lessons from Assistants vs. Agents

1.) Go one level deeper — A general newsletter about assistants might’ve done OK. After all, there are lots more people working as assistants outside Hollywood than inside it. But by taking things one level deeper — focusing on people at the intersection of Hollywood + assistant work — Bailey created a product that felt indispensable. If you’re working as a Hollywood assistant or hoping to work in the field one day, AvA feels built specifically for you. And that specificity means you’ll always make time for their newsletter or events, since they can help you get ahead in your career. When you’re thinking through the pitch for your newsletter, ask yourself: Is there a deeper level I can get to that will make my newsletter feel tailor-made for my readers?

2.) Make your community the star — In the TV and film industry, everything’s focused on the stars. Every event and every industry publication is built to showcase the people at the very top. But what about the people behind the scenes? There isn’t an Oscar for Best Assistants, but winning an AvA Award, speaking on an AvA panel or being highlighted in the AvA newsletter means being recognized for excellence by your peers. If you work in any sort of industry publication, think about ways you can celebrate excellence in the space and elevate the work your peers are doing.

3.) Know what your audience needs — Anyone who’s watched “Entourage” feels like they know a little about the world of Hollywood, but having worked in this space, Bailey’s been able to build a series of products that are designed to help his readers advance through the industry. His readers want the chance to learn from people who are further along in their careers, so he launched an interview series featuring advice from Hollywood veterans. His readers are looking for job opportunities, so he created happy hours to help them network and job boards where they can find industry gigs. Matching up the audience with their needs can make any newsletter a winner.

4.) Follow the money — These assistants are a powerful group — powerful, but underpaid. Trying to charge them directly through a subscription or membership strategy might not work. So, how has AvA monetized? They charge employers for access to the community. Want to hire someone great? You can pay to promote your listing through the AvA job board. (The kind of person who reads AvA is probably more of a Hollywood insider than the usual applicant from Indeed.) Want access to Hollywood decision-makers? You’ll have to go through these assistants anyway, so why not partner with AvA on events around town? (Plus, getting in front of the assistants is a lot easier — and cheaper — than getting in front of the A-listers.) By following the money, Bailey’s created multiple impactful revenue streams.

5.) Think partnerships, not ads — There’s an issue with industry publications: They can only reach a certain level of scale. There’s a limit to the number of Hollywood assistants (or would-be Hollywood assistants) out in the world. Even with AvA’s size and open rate, an ad in a single newsletter would only be worth a few hundred dollars. (Editor’s note: B2C newsletters have a slightly different opportunity, and that’s why we’ll shamelessly plug the Newsletter Advertising Playbook as a resource that can help you scale your ad strategy.) But by focusing on larger partnerships around events, Bailey’s been able to unlock more profitable ad opportunities that drive better long-term results for the advertiser than just an ad in a newsletter.

6.) Stay authentic — It would be understandable, if a bummer, to see the content on the Assistants vs. Agents water down as the brand and Bailey became more successful. But the Instagram page remains snarky and relentlessly punching up, whether featuring a Christmastime screenshot from an agent texting an assistant, “Kids r about to open gifts. What did you get them so I know when they open??” or an unflattering closeup of a White House spokesperson with the caption “POV: I’m about to follow up at 9:08 a.m. on an email I sent yesterday at 5:17 p.m.” Whether you need reminders by reading through your most popular posts or by surveying readers about what they most like about your newsletter, stay true to the content and voice that made your most loyal readers follow you and keep following you.