How Hollywood’s Wildest Assistant Stories Sparked a Community—and a Business with Assistants vs. Agents Founder Warner Bailey

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3:16Because the Devil Wears Prada sequel is filming right now, a lot of people are reminiscing on the OG film starring Meryl Streep as the character based not so loosely on Anna Wintour and Anne Hathaway, her cerulean and blue-wearing assistant. If you haven't worked in entertainment, you might watch this movie and think, there is no way that being an assistant is actually like this. Oh, but it is. And like most things, the truth is stranger than fiction. And to tell us some of those wild stories today, I'm talking to Warner Bailey. Back in 2018, while working as an assistant at a major agency, Warner created Assistants vs.

3:50Agents, a then-anonymous Instagram page that shared the real-life Devil Wears Prada stories of assistants working in entertainment. When Money Rehab was in the very early days, actually, and Warner was still anonymous, we DM'd Assistants vs. Agents asking for an interview, and Warner said no, which we get into with him in this conversation. But since we DM'd, the account has blown up to over 100 ,000 followers, inspired important data collection on industry pay, and if we're being real, probably made a few agents think twice before popping off in the office. Kudos, guys. If you are or have ever been an assistant, you will find this conversation extremely cathartic.

4:32But the conversation isn't just for people living inside Hollywood. Warner also talks about how to monetize a community without taking money from your community, which sounds impossible, but there are ways, and how to be a leader that inspires good work, not fear. This conversation is about accountability, money, and the power of speaking up, even when the people in charge would rather you didn't. Warner Bailey, welcome to Money Rehab. It is so good to be here. I appreciate you having me. Appreciate you getting into all this. It's so juicy. Let's start with the origin story of assistants versus agents?

5:07Was it blowing off steam to start or were you just like, these are juicy, juicy stories that nobody's telling and I have to? Yeah. So it started off the origin of it, true meme page. I had a graphic design interest as an assistant and at WMA. And when you're an assistant, there's not much creativity involved in what you're doing. The origin, origin of it was we had these manila envelopes that you would put either contracts or things along those lines within and pass them off to each other's offices. And we started kind of as a joke, putting a meme or two, something funny, a handwritten note, knowing that the first line of defense for your boss was always the assistant.

5:45So they would retrieve it. Then we went digital with it and started an Instagram account. The first, I would say a couple months, 10, 15, 20 followers. And I think that's where I thought it would cap out at. But I think the reason why I think it caught on was because it was a shared, call it trauma bonding or whatever, shared therapy. Everyone was dealing with these things. And at that point, no one was talking about it really, you know, maybe in closed circles. But, you know, I would put fun stuff, funny, I hope, and relatable things up on the Instagram account, and people were engaging with it.

6:17And it gave me kind of a interesting sight into the fact that I wasn't alone in all of it in a weird way. And it started to spread from there. What's the craziest stuff you've heard? Because you crowdsource all these stories. Yeah, it's crazy stories. We've thousands of them calling NASA to try to have a private plane land on their runway. A lot of like crazy visa stories where, you know, people had to fly to a country and try to secure a visa for someone. Then you get the absurdity of people. I think that the part that I love the most is the juxtaposition between two things you might be doing within the same hour.

6:55So again, I referenced this earlier, securing a visa for your boss's nephew or taking a driver's test for someone that was a story submitted, taking an SAT test. Probably those are pretty illegal, but then also going back and sorting M &Ms for Marshawn Lynch with gloves on. And those are probably done within the same hour. And then going out and getting six coffees for the whole office and spilling them in your 2008 Toyota Corolla. So I I think it's the absurdity of the things that you're doing within the same day or even within the same hour that makes it stand out the most. But we've been submitted.

7:27Someone had to break into a FedEx to get their boss's dress for an Emmys party. Do you think that the people that had to do some of the questionably legal things were told to do those things or they were just instructed to get it done at all costs? Yeah, I think I think it's the latter. Well, who knows? I mean, certainly the former for many. But I think with this industry, it is within the history of assistants, the ones that rise are the ones that are able to figure it out at all costs. So I think that - Get the Emmy dress. Exactly. How do you get it? There's only one way. You break in. You pay someone off.

8:00But I think there's ways to frame things, certainly saying, get it done and they'll figure it out. I was never instructed to do any of these crazy things. I was lucky enough to have some great bosses. But others, I'm sure, have dealt with crazier stuff than we've been submitted. but I think the anonymous nature at which people are able to share their stories. And some of them are, I mean, most of them are hilarious. It's just dealing with like taking your dog to a vet to get, you know, there to get braces on or like taking a turtle to get Botox done was another one. Yeah. It's probably a pretty good looking turtle at this point, but yeah, like crazy, but those aren't even the craziest ones.

8:34Does it ever scare some of them away from getting into the? Maybe, but maybe that's not a bad thing. Cause I think, you know, there's a reality of our industry, but the reality is shifting. And that's where I'm really headed towards now. It's how can we put together resources to give more insight into the current landscape, but also help change it. So to give more access to people, to find out that there's roles outside of just going to the mailroom, to we're working on a book, scripted show, things like that, that will highlight, again, the absurdity of the industry, but also provide roadmaps that may have not existed, certainly didn't exist.

9:07When I was joining the industry, and definitely didn't exist when, you know, the generation before. So that's kind of the goal now. Yeah, it may scrape some people away, but, you know, there's a reality that, you know, within every industry is there's difficulties, but there's ways to overcome it, I think. But what was your experience like at WME? Did you feel like it went from hazing to exploitation to a point where this was actually getting above and beyond the normal course of business? So to be honest, like, this might be a bit of a letdown, but I actually loved my time at WME. I think I can't pretend to share the same experience as many others who have worked in entertainment, but I enjoyed it.

9:47I also had the benefit of working for some great bosses. And I think that's where it starts. It depends who you're working for. So I was lucky enough to work for three great bosses who I'm still close with then. But no, I really enjoyed my time at WME. I come from Philly. I had no connections to the industry. It took me six months to even get an interview. I'd never been to LA before I moved here. I got an interview on a Thursday. They said, be out here by Sunday. You start on Monday. I'd never been to LA. I just felt lucky and had to just think about all the times that I wanted to break into the industry.

10:21Those points at which I was there, I appreciated my position there. Obviously, dealing with some of the stuff we did, and we'll get into how much we were getting paid, made it difficult at times, but I was lucky enough to work for some great people. What's the craziest thing you ever dealt with as an assistant? I wasn't an assistant. So what's the craziest thing you've ever dealt with in entertainment? Oh, I don't know. I was always surprised. Anytime – I had an agent very young because I started in the business very young. But I would always talk to the assistants. This is not – it just feels like normal decorum of life and be like, hey, how are you?

11:00And oftentimes they'd be like, okay, here's my boss. or like I'm not supposed to say anything. Like I'm not a human. And it would always be like the name of the person, assistant at whatever, like not their actual name because. Oh yeah, we've made many memes about not having an email address, which I still find insane. They're like people, my email was initials ASST2 because I was the second assistant for a while. So I didn't even have the first assistant email. It's crazy. It was like people reached out, they're like, hey. Second string. Second string guy, like it's great to see you. But yeah, it's crazy, but go on.

11:32because I think that part is still insane that people don't have their own email address. I just, I felt there was just like this general nervousness about talking about themselves or like having an identity. And so, you know, because I would talk to them whenever I would call and be like, how are you? You were out sick, like, are you okay? But like, there wasn't very much willingness to just have general small talk or discussion. And I just felt like, oh, my gosh, are they like in a cage or like in a dungeon? Like, are they instructed not to talk? I just felt like, are you trying to tell me something?

12:13Is this like, you know, a Brittany like cry for help situation? Are you OK? That was my only like experience with assistants. And I didn't understand the concept of the mailroom. That seemed to me. Still is. I mean, crazy. When we first started at WME, this is public knowledge probably at this point, you were handed a stack of 120 note cards and you had to memorize all of the agents initials, their four digit extension, who their assistants or assistants were by name, what territory or business unit they were working on. And you had 120. You couldn't start work till you did that. And once you did, then you had to take a states test.

12:49You had to memorize all 50 states, which I loved because that was like my brain works in that way. I'm very bad at like the math area, but that wasn't too bad. And then you had to take a typing test to ensure that you're able to type to take notes and some of that stuff like looking back it all makes sense why we were doing that you had to if your boss is like give give someone a call you had to you know know their extension now it's probably easier with you know the data that's there or states if you're routing a tour to understand where they were but it was like it literally was it was crazy to be graduating georgetown you're working in tech for six months i'm like i'm gonna go to la and then being put literally in the mailroom which is at the basement and taking a cards test i was like oh my god what I sign up for.

13:30Wait, what is a state's test? You have to fill it out on the map? Yeah, and get it 100%. It's crazy. I know. I was like, am I in fourth grade? I'm implementing this in our company. You should have everyone who goes on this podcast take a state's test. I would do the best. Do you know the state's song? No, I don't. Should you sing it? I love the state's song. Alabama, Alaska, Arizona, Arkansas, California, Colorado, Connecticut, Delaware, Florida, Georgia, Hawaii, Idaho, Illinois, Indiana. I know them in alphabetical order. You would ace the state test. Yeah, you would ace it.

14:09Hold onto your wallets. Money Rehab will be right back. And now for some more Money Rehab.

14:22So how much were you getting paid? Yes, I actually pulled my W-2s for fun. And looking back, first year in the industry, my gross pay and putting the gross in gross was$41 ,000. I think it was about$41 ,700, netting probably around$31 ,000. You think about the rent at that point,$1 ,700, I think I was paying. So you're netting out after all of it. I think it was about$1 ,000 a month you were dealing with. The second year, big bonus. I started working overtime. Started working for the head of music over there, Kirk, who I love and still very close with. But I was making 55K at that point. And to me, it was great.

15:01But at the same time, thinking about back now, it's an insane amount to be making living in LA. It was extremely hard. There was no safety net. I had to make a lot of decisions financially that weren't exciting. My brother was working at Goldman and BlackRock. And we never really talked about it. But always looking back, I think it was probably a huge juxtaposition in terms of what we were making. And we're a year apart. So yeah, 41K, first year out of college, living in LA, not an easy time for sure. So you collected data from your community about pay, right? And so you found that an entertainment system makes around 45K, but that's for a 24-7, like always on situation.

15:42But why did you start looking into how much everybody was getting paid? I'm assuming you guys didn't talk about it. Yeah, no, we never talked about it. Because I think everyone knew at that point that everyone was making the same. It was an hourly rate. Overtime was great. if you could get it. And it wasn't always allowed. So fast forward to about two years in, it started to grow a lot, reaching 50 ,000 maybe at that point within the community. And I started to think about it as a business opportunity and also identifying where the gaps were in pay and opportunity that we could start building businesses and resources around.

16:12So I set out and we did a data study. I think it was about two years ago. And we did another one last year. I think they should, everyone should pay their assistance what they think is their worth. And I'll leave it at that. But for me, I saw it as an opportunity to get a lot of really rich first party data and also set ABA apart from a lot of these other digital accounts as a true media brand, but also this educational research driven arm of the company, which we've developed a lot in the past couple of years. But it was shocking. I mean, some of the responses we got back, people were making 30 something K in 2024 was the last time we did it, which was wild to me in LA.

16:52You're also sitting on some more survey data from the music industry specifically by gender. So you found that the average for men was 85K a year. The average for women was 75K and for non-binary was 55K. What do you think the reason for that is? Men are getting promoted faster or it's simply a crazy pay gap? Yeah. So I think there's two things working at the same time with that data. One is we found that there were more men in senior roles. So that's obviously going to skew the data. And the second is, yeah, I mean, historically men have been paid more in this industry, but I do think it skewed the data much higher because men were in those leadership roles in a more prominent way.

17:38I think hopefully that has been addressed, certainly, since I've been in the industry. It's been amazing. I've interviewed 100 plus execs over the past two years. And it's been amazing to see, I think, the hope they're giving this next generation of women, non-binary individuals, that there is a path towards success and growth. But I will say, yeah, I mean, traditionally, our industry, like many, men have risen faster and are in more leadership positions. And you still see that at the C-suite level, certainly. So what's your hope by surveying everybody, bringing all of this data onto the platform?

18:10Yeah. And again, I started a meme page in 2017. Let's be clear. I had a career totally outside of that, went full-time on AVA six months ago. So there wasn't really a goal starting it. It was to kind of blow off some steam, have some fun. But for me now looking at it, I am in a position with leverage and a hyper-engaged, high-value community that I feel like I can do some good. So I'll publish the data. There are publications that will run with it. I'll let them do their thing. But then it's for me to identify where the gaps in the market. There's two of them. One is entrance into the industry.

18:43The second's retention. So I think entry and access to entertainment's always been an issue because if you're getting paid, again, 45K to work at one of these legacy companies and your rent is$1 ,800 a month, do the math, you're coming out with student debt, it's not possible for a lot of people to enter the industry. So we're building resources. We launched a job board. Actually, yesterday, we've had a newsletter for the past two years with 70 plus open jobs. We've interviewed recruitment leads. We've interviewed execs to give advice for the next generation. We're throwing events all around the country, both virtual and in person.

19:16We're doing panels. So I think we're trying to provide the tools now for people to see, and students specifically, that there are more ways to enter the industry than just to go into the mailroom at a WME or CA or UTA. There's more companies popping up than ever. There's more opportunities. I think it's easier now to launch a company than it's ever been. So to go back to the data, I think it gives us a leverage point. not only with brands, not only with investors, but also the public to say, hey, here's the issue. Let's all work on fixes to allow more people into the industry and allow for assistants and others to continue and stay in the industry longer.

19:52Do you find that a lot of rich kids go that route because they can? Yeah, I mean, certainly. And you're surrounded by a lot of it. I think, yeah, of course. I mean, if you're making 45K, to some extent, you have to have some sort of supplement. I didn't know anyone in the industry. I had very supportive parents. And I probably had a year runway before I had to really make a decision. And luckily, I was able to move up and then left to go to Live Nation. But for many, this was impossible. That's probably the biggest rag that our industry gets is that people coming from wealth will have an immediate step up.

20:28Because the other aspect of it is these opportunities are highly concentrated in cities that cost a lot to live in. So in New York and LA, even like a London, Nashville is growing now. But yeah, so I think certainly. And you get those people everywhere in finance. My brother works in finance. And when I visit in New York, everyone's wearing a vest and running around. I couldn't be seeing the tie anymore. But I think you deal with those stereotypes at every industry. But I certainly think in entertainment, you have a lot of those people. So do you remember that we reached out to you? Yeah, I do.

21:012021? And you said no. I thought it was fake, first of all. I'm like, there's a 0 % chance that you guys are reaching out to me for an interview. And I was obviously humbled by it. But yeah, I think at that point, I was anonymous behind it. So when you all had reached out, I was still in that position of kind of waiting for a firestorm to come my way from people that I had worked with. So I think at that point, I was saying no to anything that attached my name or let me have a platform with it. But here we are. Here we are. What were you so nervous about? Yeah, I mean, I think at that point, I hadn't been able to speak publicly a lot on why I was doing it.

21:37And now I am in platforms like this and, you know, through our newsletter and other forums. So I think at that point, I needed to prove to the public and people that I had worked with prior and even at that, at that point, I had a boss and I was working full time that didn't know I was doing any of this. And even six months ago, when I went full time on AVA, I still had a full time gig that didn't know I did a lot of this. And, you know, who knows, but But now they know. Well, now they know. Yeah, it's pretty obvious now. But I think the worry in my mind was that, you know, I was still not senior enough in my role for individuals to look at me like he's doing it for the right reasons.

22:16I think I was still kind of in that middle man lane, junior level, and still rising at a traditional company like Alive Nation to where they certainly would not have wanted me to hop on this podcast and talk about the issues people are facing. So I needed to set out, build a company, hopefully do some good and talk on it a lot more before I hopped on something as big as this. And I'm honored again to be on this platform and the show with you. Thank you so much for this coming out party. Yeah, here we are. Were you worried about getting blacklisted in the industry? I mean, because agents knew about the platform at this point.

22:51Yeah, certainly. I think the reason why it wasn't was because there's enough platforms out there. I won't name names that identify people by name or bring names into stories that are things that are potentially legal or wrong, immoral. For me, it's always been taking things and putting a positive spin on them. As much as the memes may seem like negative, it's really just pointing out things that everyone deals with and relatable instances in the industry. So I was never worried about the blacklist side of it because nothing I had ever posted to that point called people out by name. It was a general theme about things that assistants deal with trying to get their bosses, cousins, like daughter of visa and in Brazil, like that's not a specific tied to one person.

23:37Many people out there may be like, I've made my assistant do that at some point. But it was really about making relatable content that puts some lighthearted nature on the crazy stuff that we deal with. So in a way, I wasn't really nervous ever about that. Some people probably were like, what the hell is that guy doing? People probably were shocked it was me because a lot of people around me had no idea. So I got a lot of notes being like, I had no idea that was you behind the account for all these years. But I also got a lot of positive notes about people wanting to now support what we were doing.