The Changing Narrative of Women on Wall Street

Recently I was asked to give a talk at a conference focused on connecting female fund managers to institutional allocators, and I uncomfortably agreed. Uncomfortably because women need another 59-yo finance guy “giving them a talk” like a fish needs a bicycle, and agreed because a) I want so badly to help, and b) I think I can provide a useful perspective on the narrative-world dynamics of women on Wall Street that is largely separate from my age and y-chromosome.

So when I say “women on Wall Street”, I’m focusing on ‘risk-takers’, which is a term that has a specific meaning in finance. It’s someone who is taking risk or recommending risk in the technical sense of the word, meaning a discretionary allocation of capital to a non-risk-free security. It doesn’t mean risk-taking in the sense of running a red light or putting it all on black at the roulette table. On Wall Street, risk doesn’t mean high risk, it just means that the money is at risk. The typical examples of risk-takers in this context are portfolio managers and discretionary/prop traders (not to be confused with execution-only traders, who are just following orders), but for our purposes today I’m also going to include risk-taker adjacent positions like allocators, analysts, and investment bankers. Finance jobs that are not risk-takers include anything in compliance, anything in sales, anything in investor relations. If you’re a lawyer, you’re not a risk-taker. If you’re a psychiatrist/performance coach at Ax Capital in Billions, you’re not a risk-taker. All interesting jobs and all part of Wall Street, but not my focus here.

And when I say “narrative-world dynamics”, I mean the changing structures and archetypes of the stories we tell each other and ourselves, stories that are both created and reflected by popular media like movies and television. I’ve spent my professional career studying these story arcs and narrative archetypes, especially those we tell ourselves in the investing world. Plus, I … ummm … watch a lot of movies and television. So I’ve spent the past few days tracing the narrative archetypes around female risk-takers in movies and television shows about the banking or investment industries, and here’s what I found:

Prior to 2016, dramatic portrayals of female risk-takers (in the Wall Street sense) do not exist!

There’s not one female portfolio manager or trader or allocator or analyst or investment banker – someone whose job is to put other people’s money at risk – in any dramatic movie or television series prior to 2016 of which I am aware. Wall Street (1987), The Bonfire of the Vanities (1990), Boiler Room (2000), Money Never Sleeps (2010), Margin Call (2011), The Wolf of Wall Street (2013), The Big Short (2015) … forget risk-takers, there are hardly any women in these movies at all who aren’t wives or girlfriends or hookers or assistants. It’s really crazy! The one significant professional female role in any of these movies is Demi Moore as the Chief Risk Management Officer (the opposite of a risk-taking job!) in Margin Call, where – as all risk management and compliance folks suspect will eventually happen to them – she becomes the scapegoat for all the bad things that happen. Margin Call is, by the way, the best movie ever made about Wall Street by a mile.

All of these movies embody a specific portrayal of women that I’ll call the Rounders narrative, after Ed Norton’s famous line in that film: women are the rake. Rounders (1998) isn’t about Wall Street, but the next best thing in popular mythology – gambling. Like movies about Wall Street, the notable thing about women in movies about gambling is that they don’t exist as risk-takers, as professional equals to men. And to the extent they exist at all in these movies – as wives, girlfriends or hookers – they are a distraction to the hero’s journey. They may be beautiful and loving (I mean, Gretchen Mol, Margot Robbie, Melanie Griffiths, etc. etc.), but ultimately they are a drag and a burden to the focused risk-taking that professional investing or professional gambling requires. As for whether women themselves are capable of that focused risk-taking that professional investing or professional gambling requires … haha! don’t make me laugh.

That “haha!” is important because while there are zero (as far as I can tell) portrayals of female Wall Street risk-takers prior to 2016 in dramas, there are two that I can find in comedies – Sigourney Weaver’s villainous M&A banker boss in the rom-com Working Girl (1988) and Whoopi Goldberg’s investment banker/stockbroker (it’s never really clear) in The Associate (1996). I don’t have a lot to say about The Associate because it’s a farce in the technical sense of the word – a ludicrously impossible set-up where Goldberg’s character invents an old white guy to front her brokerage + “high-tech computer company”, who she ultimately decides to impersonate in a latex mask and then fake-murder, only to be charged with the fake-murder and blackmailed, only to mask-up again as the fake old white guy who was not fake-murdered and then unmask “in order to teach the male-dominated industry the evils of racial and sexual discrimination”. Yeah. Let’s just say that The Associate is about Wall Street in the same way that A Night at the Opera is about opera, just with 1/100^th the humor and 100x the “message”. There’s no character portrayal to analyze in a farce like The Associate – it’s a vehicle for Whoopie Goldberg as Whoopie Goldberg – just like there’s no character portrayal to analyze in a farce like A Night at the Opera – it’s a vehicle for the Marx Brothers as the Marx Brothers.

Working Girl, though … this is a character. In fact, Sigourney Weaver was nominated for an Oscar as Best Supporting Actress here, one of six Academy Awards, including Best Picture, Best Director and Best Actress, that this Mike Nichols-directed film was nominated for. That sort of industry recognition is incredibly rare for a rom-com. Such a popular movie! Everyone loved Working Girl and its profoundly anti-feminist story arc about a smart and sweet secretary (Melanie Griffiths) discovering that if she just takes off her glasses and changes her drab haircut and wardrobe, she can win the Harrison Ford pick-me contest with her evil boss (Sigourney Weaver) and find a fulfilling job far away from the rough-and-tumble boys’ world of Wall Street. Worse, because Working Girl was a comedy, and a romantic comedy at that, it could make a truly awful statement – that women who DID succeed in the man’s world of Wall Street risk-taking were terrible people – and not only get away with it but be praised for it and nominated for Oscars for it because they said it as a joke.

Why aren’t there more women portfolio managers or discretionary traders or M&A bankers on Wall Street? Because they’re not very good at it. And if they are good at it, they must be – haha! – a really awful person.

I submit to you that until fairly recently this was our common knowledge – what everyone knew that everyone knew – about women on Wall Street. Certainly this was the universal Hollywood portrayal.

That universal portrayal ended in 2016 with the release of Equity, a movie about three women: a senior investment banker, her friend a federal prosecutor, and her junior on the deal team. You probably didn’t see Equity. Its worldwide box office was <<checks notes>> $1.7 million. That is not a typo. One million seven hundred thousand dollars. Its broadest theatrical release was across 255 theaters. But you should see Equity. Not because it blows up the common knowledge about women on Wall Street. Not because of its ‘message’. Not because it was written by women, produced by women and directed by women. You should see it because it’s a good story about women who are professional risk-takers and real people!

In addition to Equity, since 2016 we’ve also had Billions (2016-2023) and its two similarly common knowledge-breaking risk-taking roles: a non-binary (but coded female) hedge fund portfolio manager (Taylor) played by Asia Kate Dillon and a female hedge fund analyst (Rian) played by Eva Victor. More recently we had Industry (2020-2023), an R-rated Brit version of Suits set in a London investment bank, with two major roles for female risk-takers. More recently still we had Fair Play (2023), a movie about a woman promoted over her boyfriend to a hedge fund portfolio manager position. Honestly, I think the writing for all of these roles is strong to quite strong, particularly for the non-binary Asia Kate Dillon role in Billions. Fun fact, the writers of Billions – Brian Koppelman and David Levien – also wrote Rounders. What makes the writing strong to me is that the characters’ non-maleness is never relevant for whether or not the characters can do the job. It’s not a thing. There’s never a moment of oh golly, I just don’t know if I can hold my own with these wicked smart men and make rapid fire decisions like they do.

And yet … while these more recent well-written, more-fully-human characters CAN do the focused risk-taking that a career in professional finance requires, there is also a strong moral message that they SHOULDN’T pursue these risk-taking careers.

Don’t get me wrong, these aren’t Working Girl cartoon villain portrayals of women who succeed as risk-takers in Wall Street. But in Equity, Billions, Industry and Fair Play,all of these non-male characters are presented as either a potential tragedy or a realized tragedy, not because they can’t do the job well, but because doing the job well requires them to choose money over virtue. They either become or are at risk of becoming a fallen woman, a tragic figure not by circumstance but by choice. At best, they get a happy ending written for them, happy because it’s an unexpected opportunity to leave the business … Taylor leaves the hedge fund to run that philanthropy she always dreamed about, Rian leaves the hedge fund to backpack around the world and rediscover her humanity. Otherwise, the emotional payoff of these scripts is that the audience gets to tsk-tsk and shake their head at the bad choices made by the women who stay!

Sure, you can do it. But you shouldn’t.

This used to be our common knowledge about risk-taking men on Wall Street, like in Wall Street or Margin Call.

Today this is our common knowledge about risk-taking women on Wall Street, like in Equity or Billions.

Is this a convergence of narrative portrayals, so that both women AND men get to be more-fully-human characters in these morality plays about love of money? Maybe. But I can’t help but notice that we haven’t had a male character struggle with this choice since Margin Call in 2011. I can’t help but notice that for every male character who did struggle with this choice in Wall Street movies from 20 and 30 years ago, there were plenty of sympathetic male characters who didn’t. I can’t help but notice that ALL prominent non-male risk-taking characters since Equity in 2016 must struggle with this choice.

Is the choice between success and virtue “real”? Is there a soul-subverting dimension to the entire exercise of managing other people’s money for profit? Of course there is! But it’s only one dimension of many – one story of many! – to what is “real” about the life of risk-taking on Wall Street. It bugs me to no end that this has become the ONLY story told about women on Wall Street over the past seven years, just as it bugs me to no end that this story has not been told AT ALL about men on Wall Street over the past twelve years.

Sure, you can do it. But you shouldn’t.

This narrative, or rather, the modern divergence in how this narrative is applied to men and women, bugs me so much for three reasons.

First, it nudges young women to choose a non-Wall Street risk-taking career in ways that young men are not similarly nudged. I’ve had this experience with my own college-age daughters. Career in law? Career in medicine? Career in science, art, tech, academia, media? Maybe the FBI? Hmm! Interesting! Career in finance? Ugh. No way. Not for me. Does it make a difference that my daughters have seen hundreds of personally and professionally successful young women portrayed in movies and television, but not ONE of those women worked and stayed on Wall Street as a risk-taker? I think it does.

Second, it nudges the rest of the risk-taking financial world (i.e. men) to doubt the women who make the choice to pursue success as investment risk-takers. <<out loud>> Oh, you’re a portfolio manager for this fund and you’re asking me to invest money in it? Well first of all, congratulations for all you’ve accomplished! I can only imagine the personal sacrifices you’ve made to get this far. <<thinking>> And the sacrifices your family has made for your choices. If you even have a family. Tsk-tsk.

Third, it nudges the women who make the choice to pursue success as investment risk-takers to doubt themselves. I think this is the most pernicious aspect of any entrenched narrative structure, that it changes the stories that we tell ourselves about ourselves. If you believe that pursuing professional success as a Wall Street risk-takers inevitably requires you to compromise your personal virtues and morality, then the more professional success you find, the more self-loathing you will experience! I call it the Nate Phenomenon, after Anne Hathaway’s boyfriend in The Devil Wears Prada. We think that the villain of that movie, the person standing between Andy (Anne Hathaway) and a successful fashion career, is her cruel boss Miranda, played by Meryl Streep. But no, Miranda is not the villain. She is the obstacle. She is the trial. The villain is Nate, the boyfriend who tells Andy that “she’s changed” once she overcomes the trials of Miranda, the boyfriend who breaks up with her because “she’s not the same person that he fell in love with”, that she’s “colder” and “only wants to talk about business”. And Andy agrees! She quits her job. She finds a lesser, smaller job, far away from the fashion industry where she thrived. At which point she reconnects with Nate and they start to rekindle (maybe) their relationship. And NOW Andy can be happy.

Look … I am all for every human being making the life choices that do indeed make them happy. Being happy does NOT require “success” in a professional field. I would be (and am) enormously supportive of anyone living their real, human life who makes choices similar to Andy! But movies and their characters are not real-life. Andy is a STORY. Andy is a constructed story, constructed purposefully to elicit your attention and approval, to generate a dopamine-heavy neurochemical response and get you to like that movie and give your money and time to the owners of that movie. There is nothing about this story that should shape or nudge your real-life decisions. But it does! And this is what bugs me. This is why the story-telling industrial complex is so problematic. We are exposed to an incredibly limited number of stories in general, and an insanely limited number of stories when it comes to women’s participation in finance, ALL of which are geared towards a very specific narrative structure for how women should make their real-life decisions.

What’s the answer to the core narrative problem here, that Sure you can do it but you shouldn’t has become the ONLY story told about women on Wall Street, and a story no longer told AT ALL about men on Wall Street?

The answer is more stories.

More stories by women about women, sure. But more stories by men about women, too. And men about men. And women about men. And everything in between or on different scales or whatever. Just more stories. So many more stories! From so many more voices!

This is why I am so excited about generative AI and its nascent video-authoring capabilities. Yes, this technological revolution will be incredibly disruptive to the current story-telling industrial complex, and I care about supporting that complex. But I care even more about getting so many more stories from so many more voices.

Within a year, maybe two, I think anyone will be able to create a feature-length movie using AI-generated imagery, voices and actors, a full-fledged story about a lived experience as a risk-taker on Wall Street that can include Sure you can do it but you shouldn’t if the author likes but is not limited toit!

A golden age of story-telling from the bottom-up is about to begin, and it’s going to change everything.