I mean, this one was a no brainer. Women shouldn’t work, let alone run companies! Don’t have to tell me twice. List item = done.
If any part of you thinks I am being serious, then dear reader, I fear you don’t know me very well. Or, if you’re new here, and really actually don’t know me yet, let me be clear: while it may have been a harsh and awful truth in 1958, in 2024, that is what the kids call a joke.
When one thinks of a woman in the workplace, their mind may jump to The Devil Wears Prada's Miranda Priestly, a notoriously kind and fair boss. Of course that is also a joke (I’m being silly today), but this part is real: despite her many, many flaws, Miranda Priestly stands tall as an example of a trailblazing, badass, no-nonsense leader who defied expectations to achieve something extraordinary.
I’m not sure anyone should aspire to work for, or become, a Miranda Priestly type, but in thinking about #19. “Don’t Work at a Company Run by Women,” I found myself itching to talk to real female leaders. The non-fiction, non-nightmare kind. I wanted to know how they got where they are, what obstacles they’re up against, what’s their life like, what do they hope for, are they hiring?
So I did just that. My first conversation was with Julia Dixon, the founder and CEO of ESAI, the original AI platform leveling the playing field for college applicants and young professionals. But, I’ll let her tell you more about it.
Julia: I’m Julia. I'm 28. I live in New York City. I am a marketing professional-turned-founder, who is trying to transition to full-time founder.
Emily: Are you still working as a marketing professional?
Julia: Technically, yes. I am now able — and we can get into this — but I have now raised an entire round [of funding] that we're closing for ESAI, which means I'm able to now do this full time. So we're in transition mode. I guess technically I’m not really a marketing professional anymore, but I do play a large marketing role in my own company, which I actually think was a huge superpower.
Emily: I want to go into where you've worked before. I think that's going to be a large part of this. You've just raised a massive amount of funding for ESAI, so why don't you tell the world what ESAI is, and can you give me like a brief overview of how you got here?
Julia: ESAI is an AI platform primarily for college applicants and young professionals as a whole.
The origin story is that I used to be a college advisor. It was more of a side gig for me. I wanted to pay my rent while I was interning and started formalizing what I was already doing informally in undergrad: helping all my law school-bound and med school-bound friends edit their admissions essays. I've always been more of the writer and creative type and all my brilliant science friends were like, “help me write an essay.” And then I had people's siblings asking me and random friends of my parents asking me and I was like, I gotta start charging for this and I started working with some high schools as their go-to advisor. I was able to build my own little side business, but it was just a human-based service.
And the kind of obvious problem was I was only really working with well resourced families. I charged on the lowest end of what these kinds of advisors charge, but most of them, especially here in Manhattan, charge $300 an hour. And some of these more elite services that work with you year round, or even for all of high school, charge well over six figures, sometimes $750,000. This is a service for very wealthy families, and that's cool. If you can afford that, it's proven to be very helpful.
But I wanted to create a way that all kinds of students could get this support. Very individualized coaching in terms of… what should you write your essays about? What school should you even apply to? How do we match your story to those schools? All those things that are a lot for a 17-year-old to grasp when it comes to creating a personal brand and summarizing everything about yourself.
I realized AI is really good at those kinds of things. It's great at making unlikely connections. It's great at taking a large amount of data and distilling it into something simpler.
That was the origin, and we've been scaling from there. We've reached over 10 million kids on TikTok, helped over 100,000 in the admissions process last year, and now we're doing this thing for real.
Emily: It's the best kind of writer origin story. You started using the skill you have, which is writing, to make money for yourself and survive. And then you were like, wait, I can help other people. And now you're making a whole ass company.
Julia: It was certainly not the game plan. I never was like, “I'm going to start my own company,” but it's just one of those things where I genuinely had a light bulb moment. It was so early in the generative AI boom. I was like, no one's doing this.
And so it just happened.
Emily: So it wasn't in the plan. Can you walk me through what the plan was? What was your resume before you started this? Where were you working?
Julia: I've worked at Weber Shandwick for the last six years, and shout out to them. Best place to launch my career. It's a pretty full service communications and marketing firm. I started there in a traditional PR, earned comms role and then transitioned into their more future facing tech team, which is where I got a lot of the knowledge that informed ESAI.
That was also accidental. My former boss and mentor, Chris Perry, exposed me to emerging tech before I knew I cared about that, and taught me how to think five years in the future, specifically from a marketing lens, but also just in general.
It wasn't meant to inform me starting a business. It just gave me this understanding that I think helped me see opportunities where I wouldn't have before. Otherwise I've mostly done traditional marketing for consumer brands, everything from Coca Cola to big cruise lines and consumer electronics. I thought I was going to have a successful marketing career for a long time.
But then I just saw another path and became obsessed with it. And here we are.
Emily: The obsession is great. Part of the reason I asked where you worked before, is this is a prompt called “Don't Work at a Company Run by Women.” And marketing and comms firms, would you agree it’s more heavily a female field?
Julia: So I can at least speak to Weber, but I know this is the general vibe across these big agencies and even marketing departments in house. Yes, it's very much predominantly women. And most of the men are gay men. We would always talk about this in my agency and at other agencies, so this is not just a critique of Weber, but it's so many women and gay men and it's empowering and awesome because we're running this… until you get to the highest up folks and then suddenly there's all these straight men. It's this very female industry until you get to the tippity top and then it's not.
That said, Weber Shandwick has a female CEO who is actually retiring and transitioning power to another female CEO. So it's not like there's not women in leadership, but there's suddenly a lot more straight men towards the top.
Emily: I don't think it's an accident that working at a place where you're surrounded by empowered women made it so that you could think, okay, like maybe I could start my own company.
Do you think that the men at the top is part of a delayed trickle down effect? In 10 years, are there going to be more women? Or is that just emblematic of a larger system that we haven't yet cracked?
Julia: I don't know if I know the answer to that. I think of a lot of the people that worked at my junior and mid level marketing roles: all these women will end up in leadership. And I hope that means that we'll keep seeing more women at the top. I just think somehow these men get pulled back up in these top roles even though it’s not as much of a pursuit among young straight men to go into a comms agency.
Maybe this isn't inherently bad. It's just interesting. There's this willingness among women to take — agencies are known to be pretty low paying — so there's a lot of opportunity, you can definitely do well. But at the beginning I just feel like women are willing to sacrifice money for something that they really want to do, or that feels creatively empowering.
I don't have the data for all this.
Emily: I have some data, which is that as of 2024, only 10 percent of Fortune 500 companies are women-led. And the number has increased in the last ten years, but it's now a little stagnant. It's the same number that it was from 2023, which I think what you said is really on point about men just taking whatever… I'm hopefully going to talk to someone that works in finance because those are famously male led industries.
It's obviously much harder for a woman to make her way up in something that is not only cutthroat, but also systemically designed to uplift the man. I'm wondering how these men find their way, for example, at a place like Weber Shandwick, back to the top.
Julia: You're getting at this whole idea, which is, why wouldn't men take an agency job in the first place? Because it’s not like men aren’t creative.
They just don't pursue creative things as much in general. But in defense of men, something I don't say super often, they are faced with more pressure to have big earnings and be providers. I felt this myself, which is so crazy because now I do not feel this way, but I felt like I had a little more flexibility in my career cause I wasn't necessarily expected to make a lot of money. I wanted to be successful, but success to me meant pursuing the most interesting and creative thing, getting recognition and good results from my job, it didn't really mean money.
It meant being able to afford to live in the city I live in. Now, that’s changed for me a lot. For a lot of reasons. But I just think that men feel like they have to pursue these high earning jobs because they have to be earners. And it's so ingrained in us that, even though I didn't actively think that way when I was picking a career, it was a factor subconsciously.
Emily: It's fascinating because this whole thing is adapted from a 1958 list when in 1958, they were like, don't take a job at a company largely run by women. Also, there weren't companies largely run by women for the most part.
Julia: Yeah, that's definitely true because there still aren’t.
Emily: I tried to do some research before and find out what are these companies that this magazine is warning women against?
There aren't a ton. And in the fifties, women only represented roughly 30 percent of the workforce and 70 percent of them were in clerical positions. Secretary roles. And I wonder if that's where this idea of… and this is a tiny tangent, but I promise it makes sense.
A couple months ago I was with some friends and we were grilling. And the boys immediately were like, “Oh, we'll handle the grill.” And the girls were like, “Don't worry we'll make the fruit.” (We're not making fruit, but we'll cut up the fruit.) And we got into this whole thing of, where did the idea that only men can grill come from?
And it's the same thing: in the fifties, it was a marketing ploy to sell grills. And it ingrained this idea that grilling is very masculine.
Especially because until — if you'd like the exact number: 1974 — women couldn't have credit cards. I just wonder if this idea that a man has to enter a career that is financially lucrative comes from these stagnant fifties ideals and the whole history of humanity.
Julia: I 100% think so. In the way it was ingrained in me. In some ways it’s nice, I felt like I had this freedom to really follow my passions because money didn't matter as much, which is great, but it's also rooted in this very sexist idea that I would probably marry someone who would make more money than me or be the primary earner. I never said that out loud or even specifically thought it, but I know that was somewhere in my mind and probably my parents’ mind. My parents encouraged me to do whatever I wanted, and I think they did my brothers too. But I just, I think it is very true, and it's rooted in very old ideas.
I see it in the way that whenever we have a family gathering, all the men immediately sit on the couch and all the women immediately go ask how they can help in the kitchen. It took me so long to even notice that pattern and be like, “Why can't I walk into my aunt's house and sit on the couch?” I'm expected to go help her. And my brothers aren't, and no one ever said that, but that's just the assumption.
Emily: The problem here is I actually like being in the kitchen. I'd love to help, but if I'm there and that disparity happens, I'll sit on the couch just to prove that the system can't win.
Julia: It's a hard one to protest because I do believe in being helpful, but also my brothers should go and be helpful.
Emily: Yeah. I'm like, you got to help.
Okay. So you used to think, all right, I'm going to marry someone who make more money than me, but now, to quote Cher, you're a rich man.
You've been pitching ESAI and apologies because I'm not as well versed in pitching a tech company as you are.
Julia: I was not until pretty recently, but I can tell you I've learned a lot.
Emily: Yeah. So before you even talk me through, I want to put one more thing out that I read about women-owned startups. It's a little dated. I would love to know what the updated stat is. But in the same way that the wage gap exists in payment, BCG (Boston Consulting Group) put out an article that the wage gap exists in women when they're pitching to investors for early stage capital.
And as someone that just pitched for early stage, can you talk me through how did that go? Did you run into this at all?
Julia: The stat that gets thrown around a lot on LinkedIn, I don't know what the latest figure is, but it's always around this, is only 2 percent of venture capital goes to women. So of all the money that gets fundraised every year, 2 percent of it goes to women. So that gap is way bigger than just the pay gap in salaries.
It's insane. Women do not raise money like men do. And part of it is that women don't start companies at the same rate, which means there's just a bigger pool of men trying to raise money, but also because it's harder for women to raise money. Both things are true.
This is such an intense topic to talk about because first of all, it's really hard to raise money for anyone, especially right now. It's like the worst fundraising environment it's been in over a decade. There was a really big spike in 2021 where people were raising money with relative ease and now it's in the toilet. That actually gets even worse for EdTech, which is technically our category. So I'll just say it was hard for a lot of reasons. And I think being a woman is one of them.
Similar to how people will rip on DEI in the workplace, people will sometimes say, “There's all these special funding programs and impact funds that only fund women and people of color.” There are some, but there's, first of all, really not that many. And they'll pick one. It's not like these big VC funds that fund hundreds of companies every year. No, they'd all try to be more inclusive, but none of them ever share their data or very few do about how many women they funded each year, what percent of their portfolio companies were created by women or people of color.
The first success I really had in funding was out of LGBT funds and LGBT communities. I do think women and minorities have to lean into them cause there aren't as many and in my case, that's not where I raised most of my money, but it is where I got my foot in the door and the confidence to keep going.
So I’m glad these things exist. I don't know if I already said this, but we just raised over $1 million in our pre-seed round. It was very hard. I have a lot of tips on how people and especially women should approach raising money for a startup.
Emily: What was the most unexpected, challenging thing about raising that money?
Julia: It's so hard because there's a knowledge gap. There's so much information online and you can basically take a masterclass in raising startup funds, but you'd have to watch hours and hours of programming. And when you're trying to build a business at the same time, that's really hard. At the beginning, people would ask me these very specific questions about our terms and our runway and our burn rate and all these things that now I get asked every day and are easy to answer. But at the beginning I was just like… “I just have this idea.”
And it was more than an idea. By the time I was pitching it, we had legitimate traction in terms of users and virality and all this stuff, but at the same time the bar keeps getting higher. Like it used to be in a pre-seed round, you're basically pitching an idea with maybe some credible founders who came from that space.
But now it's you have to have actual revenue. You have to have a ton of users. You have to have some serious not just vision, but go-to-market strategy. So the bar keeps raising. And I do just think that people are more doubtful.
A lot of people will take my calls and then they go, “I like that idea, I would love to stay in touch with you.” And I'm not aggressive enough to get them to close. Especially in the beginning would get a lot of people on the phone and get like a lot of nice feedback. And it'd be really hard for me to be like, “So are you interested or not?”
And I feel like men always take the opportunity a little more seriously. I actually pitched one fund in particular. They loved my idea and it was one of the best meetings I had early on in my fundraising journey and they were so, “You might be a little early for our fund, but we'd love to angel invest before the fund would come in, and this idea is so awesome, we've been looking for something like this.”
I got so excited. And then they ghosted me after that, which is not rare, but that one surprised me. And then I found out a couple of months later, they funded a very similar idea founded by two guys still in college.
Emily: No!
Julia: They had started later than me, had no traction. They're younger, with no professional experience.
Emily: I hate that. So that's an interesting segue, because you're working in a nascent field. You're in EdTech, you're in AI, where there's less of a history, obviously, because it's new. Are you finding that you're being treated differently?
Are these emerging markets offering new ways for women to make headway? Or are these patterns repeating itself? Like these two college kids are getting more funding than you do?
Julia: In some ways, like the VC and startup world, regardless of the exact hype of the year, remains consistent. People only take warm intros, which means you already have to be connected to get on calls in the first place. And that's a huge barrier that I could talk about forever, but I will say it is not impossible to crawl your way in. After just going to two of the main conferences, I feel like my network has really expanded and people love intro-ing each other to people because it's free and so it's not impossible, but it takes a while to spiral up and build some credibility among a certain community. But EdTech is pretty small and once you get a few under your belt, you get warm intros pretty easily.
All of that stuff stays consistent regardless of if we're talking about Crypto or AI or just SaaS platforms or whatever has been the focus of the last decade. What I do think is different is because it's so new and there's so much excitement about it, we're seeing people carve really unique spaces in it, like you can basically build an AI with AI. There's so much equalizing with this technology. Almost anyone can do it. That doesn't make it easy, but I truly use AI to help me figure out code and help me figure out everything.
I just don't think I could have built my AI company without the help of AI.
So I do see women doing really cool stuff that's creative and different and impactful. There's also specific communities. There's a Women in AI Education Slack group that has a thousand people in it now. It's all about celebrating women in the AI space. There's definitely stuff popping up, but I don't know if it's radically different than it has been for the last, who knows how long.
Emily: History of the world.
Julia: Yeah.
Emily: The other AI thing that's interesting, especially with the Women in AI Slack group, is what I was reading about the AI gender bias. I think it said 20 percent of AI workers are women right now, and because it's machine learning, the people feeding the machines are more often than re-feeding these biases
Julia: This is the problem with everything. All of the medicines we have were tested on men, and all of the safety features in cares, and now we have AI. And I, can speak to our own system in particular, our two main people behind the actual training and proprietary method in our AI are myself and my chief academic officer, Dr. Carol. If anything, ours might lean the other way. So I think we have a nice balance, but it's a huge consideration and it's maybe not as life threatening as, medical biases, but it's a real problem, and just another case for why women need to be in tech and in AI.
Emily: Women in STEM. So at ESAI, you have you — your title is CEO — you have Dr. Carol, who's your chief academic officer. How big is the team right now? And what was building it like?
Julia: Garrett is our CTO, Chief Technology Officer, and that's the core team. We have a really awesome BizDev intern, Jillian from Northwestern. And then we've got about five or six additional Product and Dev folks. So our Product Officer is Yohan Demont, and he was one of the first people to come on to ESAI and be, like, a real C-level person. He brought in our UX designer and our AI engineer, Ao, and our additional developers. We have a couple of new developers, so we've got a lot of people circling the organization. Not everyone is full time employee and some people work under the dev house we work with.
And some people work more under me. But yeah, we've got about 10 people working on this thing every day, which is pretty cool.
We started doing these daily stand ups to get everyone on the same page and it has been a little surreal to be like, wow, a year ago, I used to say the word we, so we sounded more legit when talking to people. And now there is a real we, like we are ESAI. And so it's been cool to see it grow.
Emily: Do you ever wake up and just pinch yourself? This is real.
Julia: Sometimes I'm like, why did I do this to myself? I am nine days behind on my inbox, and it's just nuts. But yeah, it is definitely surreal.
Emily: I want to talk about the term girl boss. And we can go as deep into the female focused women leader language as you want. But I'm thinking about like girl boss, She-E-O, the future is female.
A) do you hear this stuff, and B) what do you think about it?
Julia: The one I hear the most is girlboss. First of all, I’ll say a lot of it is from my own friends in a funny way, and it's not that deep. They’ll just be like, oh, Julia's girlbossing again, and it's funny, it's fine.
But in general, when some more random people say that to me, the obvious critique that we don't call it boyboss and it's just a little condescending in a way, like, “Aw, you're really trying to do that, huh?”
It feels a little gross, but I think on a deeper level it feels like this weird tendency to almost justify that, I'm starting a business, but I'm still really feminine, and I'm doing it in a feminine way. Don't worry.
There's something deeper there that feels almost like it's a defense mechanism to be like, yeah, this is the girly way to do business. So I’m still desirable. People love to say that to me and it's usually a joke, but I am like, “Why was that your first reaction?”
Emily: In some ways I feel like it undercuts an achievement because they'll be like, she's founder and she's a woman instead of just, or when people add that descriptor, and this goes for women, people of color, blah, blah, blah. It's like, why can't you just be that one thing?
Julia: Yeah, that Fleabag scene where she's I just want to be a person in business and not a woman in business.
But there's the other argument, which is we need to celebrate women in AI and women founders, because there aren't any, we need to lift them up as examples.
And it's a qualifier that's accurate. I get that. It's just, when it's the automatic descriptor in a setting that isn't really necessary. And you're like, “Why was that something you felt you needed to do?”
But I will say in the EdTech industry, compared to some other tech industries, there is always a note that there's so many women teachers, but a lot less women EdTech founders, which is interesting because you think it should be more similar, but I do think there's as a whole still more female EdTech founders than there are in other fields because education tends to touch on a women's focus.
I haven't faced a ton of this in investor calls or interviews I've done, but it's just even random people that I'll meet socially. They're always like, “Oh, she's a girl boss.” I'm just like…
Emily: If you insist.
The last big question I have for you is as you look at the next year, the next five years, to the point of girlboss and there being this disparity of women leaders, it's just generally harder for a woman to move her way up the ladder. Often, we find there's that stereotype of “Women don't always support women in the workplace,” or they can be harder on each other because they view each other as competition. As a leader and someone that is growing a company, what do you look out for and how do you center yourself and make sure that you're being the boss you want to be for other people?
Julia: To the point where women don’t look out for each other in the workforce, I've never felt that. And maybe that's a testament to how great of a place Weber Shandwick was, but it was, like I said, almost all women. And so if it felt like that, then no one would have any career growth.
So I've never felt that, some of the people who have advocated for me the most in my career have been women. Obviously I want to pay that forward. To me, one the biggest problems is that it's not that usually, of course, there's some blatant sexism going on, but it's not usually that the companies or decision makers are sexist themselves, but they're forced to make decisions based off the fact that the man came into the room with this very much ultimatum, deals defined, whatever, asked for more, and women don't.
It's not because the women are less smart or less deserving or even less good of argument makers or debaters, but we've just been taught to not do that and not cause a scene and not be too aggressive and not come off that way because it is received differently, even if you do the exact same thing.
So I think it's really hard. I've had conversations like this with my roommate who works in HR. If you're dealing with two candidates and one comes in and puts their foot down and says, “I'm only taking a salary above this.” And the other one doesn't, that the HR person can only respond to what the people tell them.
I hope that I can be someone who helps women just figure out how to advocate for themselves and be better arguers — not they have to be argumentative — but to make a strong argument for yourself.
The same goes for funding. You have to be ready to field so much pushback and so much questions and just have the confidence to do that. Sometimes when people ask me a question, I now have the confidence to say, “Can I disagree with the line of questioning a little?” and just be like, “I'm not sure I even agree with the question you're posing.” It's fine to push back as long as you're respectful. So that's something that, yes, I hope to obviously give fair shots to all my employees and women in my life, but also empower people to advocate for themselves the way that men just seem to be naturally empowered to do.
Emily: I do wonder, if the way Weber Shandwick was set up was a place where you felt empowered. And I agree. For the most part, all of my jobs have been in female led and female empowered organizations. And I think it is where you learn these behaviors that influences how we move through the workplace.
Julia: Totally. So would you prefer to work for a female run organization?
Emily: Absolutely not. No. If there's a female CEO, I'm like, remove my resume from the pile, please. I cannot be, yeah. Kidding! Yes. I want to work in places where I'm inspired and it's, often women inspire me cause they're badasses.
Okay. Final question, because this questions is influenced by a dating listicle.
Has this affected how you think about relationships and how you think about dating?
Julia: I feel like in a lot of ways, me coming out and dating women has empowered me, mostly in subconscious ways, to do things that are also outside of the cultural norm: do something crazy like start a company. I still think I bring a lot of reason and risk analysis to the decisions, but I'm just more comfortable doing other things that are unexpected because I've already faced the biggest backlash I'll ever face. (I hope.) It feeds off the other way too, now I suddenly see myself as maybe — even if I did have a husband who makes a lot of money — that's never something I want to rely on. Nor do I think that anyone should ever approach their career that way.
But I think all those subconscious assumptions have gone away. Even my own risk analysis, I have to make sure that if this thing goes to hell tomorrow, I have other options and I can provide for myself and ideally a partner that contributes.
My partner works a really non traditional job and I work a sort of non traditional job, so it's very complicated to schedule things. We just had to cancel a big trip that we were really excited for because actually both of us had career random bombs go off and we just we're now losing money on a trip we’re not going on.
It's hard, but for me, especially because my girlfriend's a dancer and I'm raising money, we are both constantly getting these rejections and good news. I felt like I was auditioning with investors and she's auditioning to casting agents and we had have these weird parallels, but it's good. We very much support each other and very much live in different universes also.
Emily: Which often makes for the healthiest kind of relationship because you can be like, here's the wild thing I did today.
Removing the need for financial security from a partner can open it up because then you're looking like, who's the person I want instead of, are they going to take care of me? Because you can take care of yourself.
Okay. I could talk for hours, but people are running companies, no one has time to listen for hours. Do you have any parting thoughts?
Julia: I'm thinking about starting a TikTok where I talk about more of these things, about how to raise money for a company and how to do really hard stuff like this. So let me know if you would watch that.
Emily: Yeah, we will. And if you're in need of an essay, go to ESAI?
Julia: Any college admissions support, figuring out what schools to apply to figuring out your personal brand, we got you. First tool is free.
Emily: I would watch your TikToks.
Julia: Thank you so much.
Emily: Okay. That's it. Goodbye!
After talking to Julia, I spoke with Amelia Montooth — the founder of Mutuals Media — about her thoughts on female leaders in the workplace. I was intrigued by a similar theme which emerged from both conversations: historically women have been trained to wait for life to happen, while men are expected to just go for it.
We are conditioned to wait. For permission, an opportunity, a text back, a first move, a lucrative offer, a husband to return from war.
In many ways, dating is not so different from fundraising for a start-up. There’s rejection, imbalances of power, and risk-taking. It’s an imperative yet impossible task: to steadfastly believe in your own self-worth and value as others question it; to get back up after a set-back; to believe in what could be, rather than what currently is.
Julia and Amelia both touched on how their rejections of the “standard” heteronormative stereotypes we’ve come to accept empowered them to take a gamble on themselves. I’ll be writing more in depth about this, and my conversation with Amelia, in a follow-up essay, but for now it’s just something worth considering.
“Don’t Take a Job at a Company Run by Women” is a small example of a larger issue which has permeated our society for, excuse my language, a long-ass time. What else are old norms and ideas are holding us back from? It reminds me of the horrible (sorry to those who love it) phrase, “If he wanted to, he would.” It’s true, but not because it’s right — maybe because it’s just what we’ve come to expect.
Julia and Amelia did something different. They challenged convention. In their cases… they didn’t wait, they didn’t ask permission, they didn’t doubt.
They wanted to, so they just did.
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