The Double Standard of Female CEOs Moving Fast and Breaking Things

Women get fired and apologize while men get praised for "intensity".

In February of 2017, Susan Fowler’s description of the pervasive cultural issues at Uber, after the company’s abject failure to address her sexual harassment complaints properly, finally broke through in a way that garnered the tech community’s appropriate attention.

The company’s bad behavior was nothing new.

Just weeks before, Uber was fined $20 million for recruiting drivers while publicly exaggerating claims of their earnings potential.

Long before that, the company engaged in anti-competitive practices and antagonized critics, especially female journalists like Sarah Lacy, who called out years of the company’s toxic issues as early 2014. She was threatened by the company, yet her call for change and her callout of top investors went largely ignored.

Even after Fowler’s article came to the forefront and investors Freada and Mitch Kapor broke ranks with their silent co-investors in their now-famous open letter, things didn’t get better. 

They got worse.

There was what seemed like an endless stream of bombshell announcements for four months:

  • Alphabet’s Waymo unit filed a lawsuit against Uber claiming that a former Waymo employee, Anthony Levandowski, stole secrets related to autonomous vehicle technology.

  • CEO Travis Kalenick was caught on film arguing with an Uber driver about Uber’s new plans to lower fares. “Some people don’t like to take responsibility for their own s---. They blame everything in their life on somebody else. Good luck,” Kalanick told his driver.

  • The New York Times revealed that Uber had been using a feature that showed people it suspected to be government officials a fake version of the app that would deny them a ride when in areas where Uber was illegal.

  • A rape victim of an Uber driver in India filed a lawsuit against Uber after executives had taken her medical records. 

There was a comment in Susan Fowler’s original public post about her experience that struck me:

“Travis should apologize and hire you back as a director.”

The comment, left by “Bob”, was prescient.

No matter how bad things got, it didn’t seem to occur to anyone, not even to that one pair of outspoken investors, that perhaps the CEO should get tossed—or at least they weren’t willing to say it.

Not in the “founder friendly” culture of tech anyway. 

Travis should hire her back?? He should have been long gone.

These vocal shareholders expressed “satisfaction” when a formal advisory committee recommended not a firing, but a “diminished responsibility” for the CEO, among other recommendations.


Two reasons:

One, they had no other real choice. Investors let him control the board as long as he continued to make them paper rich, and then actually rich--so they couldn’t technically force him out.

The second reason?

An examination of several high profile stories this past year about female CEO issues lays bare the other reason:

It’s not “founder friendly.” It’s male founder friendly.

Being a male CEO under fire affords you far more margin for error than if you were female.

Take the story of luggage startup Away’s CEO Steph Korey. It was written that she also created a toxic work environment.

There were issues around pushing employees to the brink when it came to trying to overcome the growing backlog of customer service issues--work over holidays, late nights, etc.

Many complained about her communication style, finding it to be abusive when specific employees or groups were singled out on company Slack channels— particularly customer service employees when she thought the company was failing its customers.

Yet, when Jeff Bezos famously opened up his e-mail address to customers, redirecting the onslaught to individual employees with his famous single character “?” question mark e-mails, “they reacted as though they’d discovered a ticking bomb.” 

Steph Korey can hardly be the first CEO on the face of the earth to hang an employee out to dry in the face of poor performance.

Unfortunately, she did it while being female.

If you disagree, just imagine how quickly TV viewers would be aghast if Gordon Ramsay were replaced by an equally angry female chef who screamed at anyone who burnt a crust.

It’s hard to see the difference in the levels of micromanagement and the resulting stress it created across their teams, but with Bezos, journalists explained that it just showed “how important customer service is to him.”

In fact, the Amazon founder’s ire at his perceived underperformance had become so commonplace, that it was cataloged in a series of angry “Jeffism’s” that they happily shared with his biographers:

“Why are you wasting my life?”

“Are you lazy or just incompetent?”

When men do it, they get a biography. When women do it, they don’t get to stick around long enough to see if their company is successful enough to warrant a biography.

Don’t get me wrong--the mental and emotional well-being of startup employees is a serious issue. The tech community has been having a long-overdue conversation about mental health and work/life balance and it’s something I’ve been talking up as far back as 2006, 2009, and 2014 on my blog and in public.

I continue to emphasize that as an investor today.

But I personally don’t know if working at Away is any more difficult of a work environment than your average inner-city school classroom, factory floor, or post office, not having worked in any of those places—or whether various stakeholders and onlookers just have different expectations of female founders.

It probably fall somewhere in between. I believe the emotions and experiences employees shared with journalists are real, but I can’t objectively say whether or not these startup CEOs were harsher than my first boss in a Wall Street mailroom. 

Every generation sees themselves as having had it more difficult than the ones that come after them, but the reality is that workplace attitudes and norms have shifted. 

Founders have to reckon with that.

What I do find hard to believe is that somehow all the male CEOs are doing a bang-up job of striking that balance, while all the female CEOs are struggling on where to draw the line between intense and abusive.

The media certainly seems to have decided which group they’d rather work for.

Elon Musk called an all-hands meeting at 1AM on a Sunday and got a CNBC article explaining how the move was a “vignette [that] is telling about what it is like to work for Musk”, quoting him saying “There are way easier places to work, but nobody ever changed the world on 40 hours a week.”

Side note: I’m going to go out on a limb and say that the world hasn’t quite changed yet just because a few more cars, which are a horribly inefficient mode of transportation to begin with, are electric and *questionably* better for the environment when waste and disposal is taken into consideration.

Time and time again, we see instances where employees complain about negative work environments, such as when Julie Horvath complained about her untenable experience at Github, male CEOs continue on, making some wonder where exactly the buck stops.

When it happens at companies run by women, the media, disgruntled employees, and their investor board members, burn them at the stake. 

(Pardon the very intentional expression.) 

This seems especially true when female founders aspire for their companies to fulfill a higher purpose via a lofty narrative.

In the case of Away, the media pointed out the “gap between how Away appears to its customers and what it’s like to actually work there.”

“It’s a cult brand, and you get sucked into the cool factor. Because of that, they can manipulate you.” said one Away employee.

Is it me or is there no bigger cult founder figure in the founder world than Elon Musk?

How come employees of Elon Musk never feel manipulated into overworking themselves or subjecting themselves to be pushed beyond reasonable limits? 

Or is it that the media just never tells the story this way?

Given the average person’s opinion of female authority figures, perhaps both.

Gwynne Shotwell joined Musk’s rocket company, SpaceX, as employee No. 7.

“There’s no question that Elon is very aggressive on his timelines, but frankly, that drives us to do things better and faster,” Shotwell said in a TED talk. “I think all the time and all the money in the world does not yield the best solution, and so putting that pressure on the team to move quickly is really important.”

Maybe he’s just nicer in Slack channels? I have my doubts.

Even when a female founder isn’t blamed for anything related to her own company culture and creates a genuinely female-friendly product, like Bumble founder Whitney Wolfe Herd, she gets attacked for her association with a problematic male business partner and investor.

Nevermind that the only reason she connected up with this person was that she had just been unfairly tossed out of a company she blew the whistle on as part of a sexual harassment lawsuit. Fundraising was hard enough as a woman, let alone one coming out of that kind of controversial situation.

She did an amazing job making the most of what she could start with, creating a safe and largely respectful product for women compared to competitors. She became a terrific and triumphant example of resiliency—yet a takedown story still found its way to her.

You could argue it’s more about her co-founder/partner, but the article doesn’t seem to expect much of him—reinforcing the generally low standards for male founders and how damaging these stories can be to women.

There’s probably no better example of a founder who tried to elevate their company around a higher purpose than Audrey Gelman of The Wing, a co-working space for women. 

In late 2018, the company raised $75 million Series C from Sequoia, arguably the top VC firm in the world. They were opening locations left and right and had one celebrity after another on its events roster. After being largely ignored by Valley investors (the biggest checks in her seed, Series A, and Series B came from men on the East Coast), she finally found support from the VC elite.

Nine months later, Audrey became the first executive to appear visibly pregnant on the cover of Inc magazine. Parade called it a “a helluva boss move” and she was praised far and wide for bringing the difficult balance of motherhood and career progression to the forefront. 

Yet, and this will come as a surprise to no one who has ever managed a hospitality business, things weren’t going *perfectly* at the four-year-old startup with 10,000+ members—which feels like the standard female founders are held to.

The media, genuinely tired of the story of her success, was all too eager to point that out.

When covering a story of a mishandled altercation between members of The Wing that involved issues of race, Jezebel referred to The Wing as “a glossy women’s coworking space we keep having to write about.”

I do not recall, in the entire history of Silicon Valley’s obsession with Uber and their ever-growing valuations... or Tesla, Facebook, or Apple for that matter… ever reading a journalist saying they were tired of covering the company. 

Whereas the tech community was quick to coin the Uberization of everything and laud the company’s boldness, the media seemed to find The Wing’s success and its pastel color scheme…


In 1991, Hillary Clinton was thought of as “a potential liability to her husband’s political career whose feminism and ambition were a bit unseemly.”

And her voice… We look for reasons to take women down. Even the questions that VCs ask women are different than those they ask men—oriented more towards failure and less towards potential success.

As an investor in The Wing, I have no doubt that Audrey can relate the impossible expectations we set for ambitious women and the nearly non-existant margin for error, especially given that the company took off after the 2016 election. 

With both leaders, mistakes were certainly made. Hilary Clinton isn’t perfect and neither is Audrey Gelman.

I’m no more privy to any of the internal issues that led to the June staff walk out of The Wing during the country’s racial reckoning, but I couldn’t help find a pattern in what I was seeing.

Both male and female founders have blind spots. Their singular focus on a company’s mission often causes them to overlook the contributions of their teams and take them for granted.

Yet, time and time again, this seems to get folded into a narrative of boldness and unyielding dedication when it comes to men—who rise above the “distractions” and “naysayers”.

When it comes to women, the story becomes about abusiveness, insensitivity, or oversensitivity towards victims of those very same potential shortcomings.

Ty Haney of Outdoor Voices was criticized for being difficult to work with--even called “spoiled”

The Times wrote about how “Mickey Drexler, the retail legend” joined the company in 2018, and his “decades of experience and deep knowledge of the retail industry were expected to help Outdoor Voices make the transition from scrappy start-up to mature business. But his input was not always welcomed at a company built on the vision of its charismatic founder.”

Translation: This older guy told this young woman how to be successful and the problem is she wouldn’t listen.

Perhaps she was right not to.

Drexler wound up having to leave his post at J.Crew with his last two years there being seen as a failure.

Now Haney is back, admitting her mistakes, but not getting wrapped around the axle in apologizing for them--instead focusing on a new mission of empowerment for the company.

On the other hand, we praise men for not caring at all about things like culture or values--but instead in vague, handwavy concepts like “the democratization of financial systems”. 

Lack of care for “distracting” political issues like racism is a brand new management style that some Silicon Valley elites say aspiring founders should strive to adopt.

In a memo detailed on the company’s blog, Coinbase CEO Brian Armstrong moved his company towards an entirely “work-focused” apolitical stance, citing, as far as I can tell, management’s inability to empathize with anyone for whom government policy, save for capital gains tax, couldn’t be conveniently and easily ignored. 

The whole thing started with Armstrong’s outright refusal to publicly support the Black Lives Matter movement and a walkout of employees.

YCombinator founder and aspiring elite men’s secret retreat leader Paul Graham tweeted, “I predict most successful companies will follow Coinbase’s lead.”

VC David Sacks tweeted “💪 leadership”, demonstrating that there’s no such thing as being too on the nose with tropes when describing successful leadership with a flexed bicep. 

I wonder how they would have felt had Audrey Gelman faced her employee’s digital walk out with the same indignance, instead of offering her resignation. Over the summer, employees of The Wing exercised their right to speak out against their employer after experiencing emotional distress in their workplace, undoubtedly exacerbated by the financial instability created by the pandemic. 

For her attempts at *trying* to create an inclusive space for women, and failing to navigate the complexities of intersectionality and race, she lost the support of her team and board, was ousted, and then apologized for her actions.

Yet, many said this wasn’t enough.

Meanwhile, even after *sixty* Coinbase employees decided they’d rather take a buyout than work for a company with such insensitive policies, the praise continued for Armstrong, who got to keep his job.

I’m not defending Audrey’s actions as a CEO. 

Not only do I not know what it was like to work for her at The Wing, but I also haven’t ever worked a hospitality job, which I’m pretty sure I would be terrible at. I especially haven’t worked in a hospitality job or any other job while Black. 

I do not imagine it to be in any way easy.

I’m sure it was made more difficult than it perhaps needed to be given that the speed at which a startup moves is often too fast for an adequately healthy and respectful culture to take hold. 

Having worked with over eighty founders in general and nearly thirty female founders, I know this can be a blind spot.

What I also see is that male CEOs have far more freedom to either work out their blind spots or ignore them entirely at their own discretion—earning unrelenting board support either way.

Even when it feels seemingly obvious to everyone that a CEO’s behavior puts a company in jeopardy, as in the case of WeWork’s Adam Neumann, investors left him in control for so long that they had to negotiate a payout worth billions just to get him out.

That seems to be a common thread as well. 

High profile male CEOs, like ultimate example Mark Zuckerberg, retain ultimate control of their startups for far longer than female CEOs--often leaving no bad deed punishable by any means.

What I see is that when male leadership “intentionally doesn’t give a shit about any of this,” they have a better chance of succeeding and getting support than when women position themselves as “far from perfect, but striving to improve.”

Armstrong first explained that the company will be focused on nothing else but “the mission,” only to take to Twitter to constantly talk about being focused on the mission of being focused on the mission when his stance earned him more and more praise.

In hindsight, it seems clear that instead of actually attempting to build something *more* than just a coworking space, a clothing brand, or a luggage company, the female founders I mentioned shouldn’t have bothered at all. For women, the startup ethos of moving fast and breaking things as part of a larger mission is a bunch of pure bullshit and they’re likely to get called out for their own personal shortcomings before they’ll have the same opportunity to eventually making good on the hype as men.

Although, had they just ruthlessly pursued growth and financial success in a head’s down manner, it’s not clear they would have had an easier time appearing any easier to work with. Women are expected to have a mission for their company, or to not just be a founder, but to be defined as a female founder with all of its resulting extra expectations.

It’s frustrating to read Audrey’s sincere apology knowing I’ll never read apologies from the founders of Uber, WeWork, or Github--and for that matter, Facebook, Apple, or Amazon, whose leaders get praised for their bottom-line success by any stylistic means necessary, no matter what kind of interpersonal friction or failures they may have had.

It took me a long time to write this—to figure out exactly what I wanted to say, how to capture the issue, and to try hard not to be dismissive of the criticism of these founders. I’m quite sure I didn’t get it all right.

I’m also quite sure I’ll face less scrutiny than had a female VC or founder wrote what is obviously true:

There is a double standard.

We hold our female CEOs to impossible standards while not holding their male counterparts to high enough ones.

Also, it pisses me off. 

I’m pissed off that the startup ecosystem is supposed to be founder-friendly, supportive of trying really hard things, there for you even if they don’t work out as planned, but that this courtesy gets applied completely unevenly.

Women don’t get the same leeway as men do when it comes to making mistakes or just making attempts. 

It makes me want to quit venture capital entirely. It’s an embarrassment to the ecosystem.

I’m a small, passive investor in The Wing, financially incentivized to want it to come back and be a wonderful working environment for both members and staff. I believe it still will.

Did I think it had achieved perfection? Of course not. 

All startups, and all founders, operate far from perfectly. How the rest of us handle that reality is where I take issue. 

I’m tired of women trying ambitious things and winding up being the only ones apologizing for getting things wrong.

I know I couldn’t run The Wing, Away, Rent the Runway or Outdoor Voices and I’m quite sure that few of the journalists that write about them could either—at least not without being written about as a female CEO who doesn’t do the absolutely perfect job of walking the impossible tightrope between aggressive and prickly, pleasant, glamorous but serious, ambitious and… you get it... 

Instead of inspiring people to find the best possible solutions to complex problems by informing and educating, some journalists thrive on just alerting—pointing out problems, most notably when there’s a female founder in the middle of them.

Nothing drives up the clicks on both sides like a struggling female CEO.

There’s a real conversation to be had about the intersectional conflicts that exist in the workplace and the changing attitudes around the pressures of work. There’s a reality that a lot of the work that needs to get done isn’t that interesting or rewarding, and that the person who is going to be rich after everyone’s hard work is mostly just the founder and the first handful of employees.

That doesn’t mean anyone should be made to be sick or unhealthy for doing it--but this is hardly an issue that ever comes up when a man is at the helm.

Do we think Microsoft was a joy to work at in the early days under Bill Gates?

Hollywood made movies about Steve Jobs and Mark Zuckerberg being absolute assholes, not just to their employees but even to their family or friends.

We tell young founders to aspire to be the next one of these guys.

I want every company I invest in to be a great working environment, and if it isn’t, tell me what I can do about it. 

My e-mail address is

My biggest fear is not that there’s some toxic workplace lurking around in the dozens of companies run by female founders I backed that I don’t know about—it’s that there’s a female founder who won’t even bother starting up because she knows she’s one bad day’s Slack thread or one heated office exchange away from being roasted on a spigot while her investors duck and cover.

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