Welcome to this week’s transcribed edition of This is Your Life in Silicon Valley. We’re running an experiment for Extra Crunch members that puts This is Your Life in Silicon Valley in words – so you can read from wherever you are.
This is your Life in Silicon Valley was originally started by Sunil Rajaraman and Jascha Kaykas-Wolff in 2018. Rajaraman is a serial entrepreneur and writer (Co-Founded Scripted.com, and is currently an EIR at Foundation Capital), Kaykas-Wolff is the current CMO at Mozilla and ran marketing at BitTorrent. Rajaraman and Kaykas-Wolff started the podcast after a series of blog posts that Sunil wrote for The Bold Italic went viral.
The goal of the podcast is to cover issues at the intersection of technology and culture – sharing a different perspective of life in the Bay Area. Their guests include entrepreneurs like Sam Lessin, journalists like Kara Swisher and Mike Isaac, politicians like Mayor Libby Schaaf and local business owners like David White of Flour + Water.
This week’s edition of This is Your Life in Silicon Valley features Lisa Fetterman – the Founder/CEO of Nomiku (a Y Combinator alum). Lisa talks extensively about why Silicon Valley does not care about female founders, and proposes a solution to the problem.
If you are interested in diving deep into the diversity problem in technology, this episode is for you.
Rajaraman: Welcome to season three of This is Your Life in Silicon Valley. A podcast about the Bay Area, technology and culture. I’m your host Sunil Rajaraman and I’m joined by my co-host Jascha Kaykas-Wolff.
Kaykas-Wolff: So, now I got a straw poll for you. Are you ready?
Before deepfakes and alternative facts, the online world was already telling us fibs. In our series Lies the Internet Told Me, we call ’em all out.
When I was a teenager, I’d wait until my parents were out of the house before slinking off to the study to fire up our family computer and ask Google questions about what I’d heard at school that day.
Does too much sex make your vagina loose? Can too much masturbation stretch your vagina? How can you tell if your vagina is loose? Ways to tighten your vagina. These are just a few things I’d type with abandon into the search engine.
Once I’d hit my limit for fear-mongering and medically inaccurate information, I’d wipe clean the search history and watch TV with my brother. My eyes would be fixed on the show, but my mind was busy elsewhere, turning over the morsels of inaccurate information I’d just consumed as fact.
It took me many years to realise that the after-school internet searches that fed me dangerous lies about sexual health had a lasting influence on how I felt about my vagina, my sexual behaviour, and my self-worth.
My adolescence coincided with the birth and mass adoption of search engines, and I often found myself getting lost in the novelty of these newfangled portals to boundless sources of information. Coupled with the fact that the sex education I received at school amounted to being shown photos of STI-riddled genitalia and not much else, my insatiable curiosity and unregulated search engine usage were a hazardous combination.
At school, I’d hear terms like: “bucket fanny” to describe a loose vagina. “It was like throwing a hot dog into a cave,” was one particularly coarse description that has unfortunately stuck with me. “Loose mitt,” “wizard’s sleeve,” and “clown’s pocket” are a few other choice expressions. These phrases elicited loud guffaws from the teenage boys at my school, but when I heard them, I burned with shame.
The message to my teenage self was loud and clear: Loose vaginas aren’t just undesirable, they’re a source of mirth and scorn. Later, in my twenties, worries about my vagina would enter my mind often — too often for my own good. If I was in a new relationship with a man, I’d fret over whether my vagina felt tight enough during sex. These worries would heighten when friends of mine would repeat things said to them by men after sex. A friend once told me her boyfriend used to always say “your pussy feels so tight” after they had sex, which prompted me to go home and stare at the wall while my brain spiralled out of control.
I’m not alone. Vaginal tightness is still a major source of worry for youth and adults, said Amber Newman-Clark, education and wellbeing specialist at sexual health charity Brook, which works with those under 25. That’s partially because of the free-flow of misinformation about sex online as well as poor sex ed in schools. E-commerce marketers manipulating women’s fears to sell shady vaginal tightening products on sites like Amazon don’t help either.
Can a vagina actually stretch out of shape?
Vaginas don’t stretch out of shape due to lots of sex. Bianca Palmisano, founder of , a sexual health training organization, explained that the vagina is an organ made of smooth muscle tissue. “It expands when stretched and then goes right back to its resting state, just like your stomach after a big meal,” she said.
The vagina’s smooth muscle and rugae allow it to “stretch for penetration or for a vaginal delivery” as well as collapse at rest with its walls touching to prevent air getting inside, wrote Jennifer Gunter, a gynaecologist, in her book (publishing Aug. 27). “Everyone (okay, the patriarchy) seems very impressed with the ability of a penis to grow, but the few centimetres of change that a penis can muster up pales in comparison with the vagina’s ability to stretch.”
It’s the muscles surrounding the vagina, not the vagina itself, which can loose tone if they’re traumatically stretched during a difficult or extended childbirth. In those instances, physical therapy is required to restrengthen the muscles that hold the uterus in place and circle around the bladder.
This cultural obsession with vaginal tightness — and its lack of foundation in science or medicine — is a hangover from a bygone era when a woman’s value was measured by her virginity and childbearing potential. Beneath the persistent veneration of virginal women lies a desire to control women’s sexual behaviour. And it works. If women become scared that their vagina is loosening, they often “self-limit the number of partners they have” in order to be more accommodating to men’s sexual desires, Palmisano said.
Andrea Barrica, founder of online sex ed platform O.school, echoed that sentiment. “This whole concept likely stems from cultural shame around people, especially women, having many sexual partners, not the medical and wellness community,” she said.
Vagina snake oil
If you Google “how to make your vagina tighter,” scores of tightening sprays, gels, and electrical “wands” will appear at the top of your search results. The first product that appeared for me in Google’s search results is an “Amazon’s Choice” product called “Intelligent Tightening Spray 15ml, for Women to Become a Virgin Again.” Amazon even has a dedicated category page titled “vagina tightening products” containing over 5,000 items.
Mashable flagged several worrying products to Amazon, which the retailer reviewed and removed from the site. “All selling partners must follow our selling guidelines and those who do not will be subject to action, including withholding of funds and potential removal of their account. The products in question are no longer available,” an Amazon spokesperson told Mashable. Per Amazon, the dedicated category page is automatically populated based on people’s search terms.
Gunter warned in her book that these tightening products risk killing the healthy bacteria in your vagina, damaging the mucus, or even causing microtrauma due to vaginal tissue irritation.
“It’s scary because a lot of these products and methods are actively dangerous, and they’re being sold to vulnerable people.”
Ellen Scott — lifestyle editor at Metro.co.uk who regularly reports on medicallyunsafeproducts marketed to women as vaginal tighteners — thinks Etsy, Pinterest, and Instagram are particularly troubling because “ideas of ‘wellness’ go unchecked.”
“If you look around Etsy you’ll find so many vagina tightening products,” said Scott. “It’s scary because a lot of these products and methods are actively dangerous, and they’re being sold to vulnerable people who have been taught to hate their vaginas or that something’s wrong with them.”
Or that they’re having too much sex.
“Sex is a normal, healthy part of life and as long as you are happy with it, it’s consensual and you don’t feel it’s getting in the way of your everyday life, then there isn’t such a thing as ‘too much’ sex,” said Barrica.
And for those still worried about their vaginas’ size, Palmisano has some useful advice:
“Take some time to read some literature that affirms your worth as a person beyond how satisfying your vagina is to your future partner. If you’re not in pain, then you’re perfect. Look for narratives that speak this truth about your body.
I wish I’d been told this when I was growing up. I could’ve used accurate, positive, and science-based information about my own anatomy during those formative years.
All I can do now, though, is reaffirm that my value doesn’t lie in the way my vagina feels to someone other than myself.
Play it cool. Keep it breezy. Treat ’em mean. Don’t reply straight away. Be aloof. Be distant. Be hard to get. These are the rules you need to follow in order to be “The Cool Girl” — a prevalent dating trope that many women feel pressured to conform to lest they be labelled clingy or desperate.
The cool girl started out as a stock character born out of male-authored literature and movies. But, the trope has since become so pervasive, the cool girl is now firmly cemented in dating culture, with no sign of disappearing anytime soon. The cool girl is no longer merely a character in a book — she is the acme of female desirability. She is the three-dimensional flesh and bone incarnation of the male fantasy. She is the rejection of the nadir of female behaviour — clinginess. And to many of us, she is a stifling behavioural standard that forces us to hide our true personalities.
Ever since I started dating as a teenager, I have internalised the notion that I need to to feign indifference and affect cool standoffishness in order to “Get The Guy,” so to speak. Unconsciously, I carried this rule into adulthood — it manifests in my behaviour at the start of relationships, it infiltrates the advice I give to friends, and it fuels my anxiety until the mask slips and my authentic self is exposed.
In the books I read, the films I watched, the most beguiling and intoxicating female characters were unobtainable and remote — their desirability being inextricably tethered to their silent disinterest and unattainability. Think of Eustacia Vye from Thomas Hardy’s Return of the Native, Cecilia Tallis in Ian McEwan’s Atonement, Estella in Great Expectations by Charles Dickens.
“I kind of feel pressure from the world in general not to be who I am.”
Lately, I’ve begun questioning the suffocating pressure I feel to adopt this role whenever I start seeing someone new. Who told me I need to masquerade as someone else and to literally adopt a different personality in order to be desirable to the opposite sex?
Writer Katie Tamola, who dates men, told me the “cool girl” ideal has been drummed into her since she was a child. “I’ve just always had people close to me tell me I need to play it cool with dudes,” she tells me. Tamola says family members and teachers have told her to “stop being so emotional and expressive” — especially with men.
“I kind of feel pressure from the world in general not to be who I am,” Tamola says. “I’ve always been emotional and immensely passionate about things. I often find myself wishing I could be the calmer, cooler version of a girl that I see portrayed in media.”
Student Alex C. (who prefers not to disclose her full name) tells me that “attempting to be the “cool girl” doesn’t just apply to heterosexual dating.”
“I constantly feel this pressure as a gay woman dating women,” she says. “It definitely seems to be the case that the person who is the least interested and most aloof holds the most power, and will get hurt less if things go south.
“I believe some of the pressure also comes from trying to avoid the lesbian U-Haul stereotype where women get serious way too quickly because nobody is putting on the brakes,” she says.
Alex explains that she now tempers her expectations and holds herself back from expressing the full extent of her feelings. “It’s a shame dating has come to this because how can anybody feel really excited about a date or know if someone is really interested in them when we’re all suppressing those feelings?”
“The person who is the least interested and most aloof holds the most power.”
The cool girl is everywhere. She’s in the books we read, she’s on our TV and movie screens, she’s in the dating advice we give and receive. From every angle, the pop culture we consume solidifies the cool girl ideal as the zenith of feminine desirability. Perhaps one of the best descriptions of this trope can be found in Gillian Flynn’s Gone Girl. Flynn’s summation of this trope hits the nail bang on the head: “Being the Cool Girl means I am a hot, brilliant, funny woman who adores football, poker, dirty jokes, and burping, who plays video games, drinks cheap beer, loves threesomes and anal sex, and jams hot dogs and hamburgers into her mouth like she’s hosting the world’s biggest culinary gang bang while somehow maintaining a size 2, because Cool Girls are above all hot.”
Dr. Stacy Gillis — senior Lecturer in 20th century literature and culture at Newcastle University —believes the cool girl is rooted in “how women are discursively positioned within patriarchal structures of power.” Gillis views this trope as related to a “predator-prey conquest model” whereby the cool girl is unobtainable until she’s conquered by the right man. “It’s about unattainability, but with the hint that you will be able to be attained,” says Gillis. “With the promise that with the right man, he will be able to break down this woman’s barriers.”
Research into the ways in which women present themselves on dating apps can also shed some light on the pressures women still face to conform to certain behavioural ideals. Siân Brooke, DPhil researcher at the Oxford Internet Institute, has conducted research into how women present themselves on dating apps like Tinder and Bumble.
“‘Coolness’ or ‘being cool’ is a trope that is gendered and often racialised,” Brooke tells me over email. “When used to describe women, ‘coolness’ refers to the adoption of typically masculine ideals of behaviour, such as a liking football or gaming.” Brooke believes the cool girl is a rejection of an antithetical feminine dating stereotype: the clingy woman.
“A particularly prevalent idea is that women are ‘clingy,’ which was quite common in research I have conducted both on dating apps and memes,” says Brooke. Clinginess is, per Brooke, a gendered term which pertains to “excessive emotional dependence” — an “undesirable” behaviour in dating culture.
“Clingy is not just attachment but is specifically associated with men complaining about a woman’s behaviour and perceived excessive need for attention,” says Brooke. The negative connotations of being branded “clingy” may, according to Brooke, cause some women to choose to act “distant and removed” from a potential partner. “The negative association of feminine behaviour can lead women to adopt masculine traits that they see as making them more desirable in dating, where so-called feminine behaviour is often demonised.”
Brooke says during her research she found that women who use dating apps often choose to feature a selection of images that exhibit common cool girl attributes. “My research has shown that women will populate the images they have on their profiles with items they believe show ‘coolness,’ such as engaging in physical activities in photos where they aren’t ‘made up’ (i.e. hair and makeup),” she says.
So, where does this ideal actually come from? Male-authored female literary characters have historically embodied characteristics like aloofness and unattainability. They are often troubled and in need of taming. Gillis says this trope can be found in popular fiction at the end of the 19th century, beginning of the 20th century, but it may well go further back than that.
“I can certainly think of a few instances of it appearing in 1860s sensation fiction, and this is a longstanding discursive structure,” says Gillis. “It’s very seductive, women are coercively interpolated into feeling that this is how they need to be in order to attract male attention.
“It’s that distancing come hither look, you see this being written about in popular fiction in the end of the 19th century, beginning of the 20th century, and invariably those women in those narratives end up married,” Gillis continues. “It’s an inversion of the Rochester-Darcy model except that there’s no agency for women behind it because it’s still located within patriarchal structures.”
“We become supplicants, we want the male gaze to come at us so we’ll do whatever it takes.”
Things have arguably moved on a little in society since the 19th century, so why is it that women still feel pressured to adhere to an outmoded concept of female attractiveness? Gillis believes this comes from a “desire to be desired within the patriarchy.”
“If there’s only certain ways in which you can be desired within the heteronormative patriarchy then you’re inculcated into this position,” says Gillis. “This is how we — as minorities in a patriarchy — are interpolated into these positions whereby we become supplicants, we want the male gaze to come at us so we’ll do whatever it takes.”
In my own infuriating experience, I feel a kind of damned-if-you-do predicament when faced with my desire to rail against this archetype. “The thing is, though,” a female friend recently said with a grimace. “Being the cool girl actually works.” She’s right, in a way. Women are continuously told that this behaviour model works, that it’s a tried and tested trick of the trade, one that you can deviate from at your own risk.
So, how do we go about dismantling this stereotype? Gillis hypothesises that queer popular culture has the power to upturn these stereotypes that are still a source of pressure for women. “‘Queer popular culture’ is a space in which there’s a playfulness to these tropes and roles, they’re seen as something you can move in and out of,” she says.
“Any stereotype can be dismantled, it doesn’t happen overnight. The challenges to this come from Young Adult and LGBTQ fiction which mocks these longstanding romance traditions.”
In the meantime, I’ve made a vow to avoid playing the cool girl when I’m dating. I can no longer pretend to be someone I’m not just so I can fulfil a rigid stereotype of female attractiveness. I am not the cool girl, nor will I ever be. Take it or leave it.
“Feminism,” the writer and editor Marie Shear famously said in an often-misattributed quote, “is the radical notion that women are people.” The genius of this line, of course, is that it appears to be entirely non-controversial, which reminds us all the more effectively of the past century of fierce debates surrounding women’s equality.
And what about in tech ethics? It would seem equally non-controversial that ethical tech is supposed to be good for “people,” but is the broader tech world and its culture good for the majority of humans who happen to be women? And to the extent it isn’t, what does that say about any of us, and about all of our technology?
I’ve known, since I began planning this TechCrunch series exploring the ethics of tech, that it would need to thoroughly cover issues of gender. Because as we enter an age of AI, with machines learning to be ever more like us, what could be more critical than addressing the issues of sex and sexism often at the heart of the hardest conflicts in human history thus far?
Meanwhile, several months before I began envisioning this series I stumbled across the fourth issue of a new magazine called Logic, a journal on technology, ethics, and culture. Logic publishes primarily on paper — yes, the actual, physical stuff, and a satisfyingly meaty stock of it, at that.
In it, I found a brief essay, “The Internet of Women,” that is a must-read, an instant classic in tech ethics. The piece is by Moira Weigel, one of Logic’s founders and currently a member of Harvard University’s “Society of Fellows” — one of the world’s most elite societies of young academics.
A fast-talking 30-something Brooklynite with a Ph.D. from Yale, Weigel’s work combines her interest in sex, gender, and feminism, with a critical and witty analysis of our technology culture.
In this first of a two-part interview, I speak with Moira in depth about some of the issues she covers in her essay and beyond: #MeToo; the internet as a “feminizing” influence on culture; digital media ethics around sexism; and women in political and tech leadership.
Greg E.: How would you summarize the piece in a sentence or so?
Moira W.: It’s an idiosyncratic piece with a couple of different layers. But if I had to summarize it in just a sentence or two I’d say that it’s taking a closer look at the role that platforms like Facebook and Twitter have played in the so-called “#MeToo moment.”
In late 2017 and early 2018, I became interested in the tensions that the moment was exposing between digital media and so-called “legacy media” — print newspapers and magazines like The New York Times and Harper’s and The Atlantic. Digital media were making it possible to see structural sexism in new ways, and for voices and stories to be heard that would have gotten buried, previously.
A lot of the conversation unfolding in legacy media seemed to concern who was allowed to say what where. For me, this subtext was important: The #MeToo moment was not just about the sexualized abuse of power but also about who had authority to talk about what in public — or the semi-public spaces of the Internet.
At the same time, it seemed to me that the ongoing collapse of print media as an industry, and really what people sometimes call the “feminization” of work in general, was an important part of the context.
When people talk about jobs getting “feminized” they can mean many things — jobs becoming lower paid, lower status, flexible or precarious, demanding more emotional management and the cultivation of an “image,” blurring the boundary between “work” and “life.”
The increasing instability or insecurity of media workplaces only make women more vulnerable to the kinds of sexualized abuses of power the #MeToo hashtag was being used to talk about.
Several states, including Alabama, Georgia, and Missouri have recently passed laws that effectively ban abortion. They prohibit the procedure just weeks into pregnancy and, in some cases, make providing abortion care punishable by a years-long prison sentence.
While these bills have yet to go into effect, and will likely be stalled by lawsuits challenging their constitutionality, the bans have prompted outrage and panic.
As legal battles play out in courts around the country, it’s important to remember that state-based grassroots groups and clinics will need even more support to serve patients who continue to seek abortion care.
Earlier this week, Steph Herold, an activist and social scientist who studies representations of abortion in the media, tweeted a comprehensive thread of local and regional organizations that help protect access to abortion in every state in the U.S. as well as in Washington, D.C., and Puerto Rico.
Hopping mad about dwindling abortion access? Welcome, we’ve been waiting for you.
Here are some ways you can show up today in your state — please settle in for the long haul. We need you now, and we need you for the weeks, months, and years to come.
Some groups, like abortion funds, help people access care by paying for their medical costs, providing transportation, and arranging child care. Herold also included information about clinics that provide abortion care, and her follow-up thread provided even more details about how to support community-run clinics, including through financial donations and volunteer hours.
“What gives me hope is that people are looking for a way to support abortion rights where they live, and that there are existing organizations — abortion funds — that [have] the infrastructure, historical context for these abortion bans, and a race, class, and gender analysis that will help abortion rights advocates win in the long term,” Herold wrote in an email to Mashable. (See below for excerpts from her viral thread to learn more about how to help in states like Alabama, Indiana, and Ohio.)
While people might first think of donating to well-known advocacy organizations that can sue to stop the bans, aiding on-the-ground, local groups can make a big difference as well.
“It’s important to resource grassroots efforts because these are the people and organizations closest to the people most impacted by the barriers and bans,” Yamani Hernandez, executive director of the National Network of Abortion Funds, wrote in an email. “They are often the least resourced and abortion funds are no exception.”
The average budget for an abortion fund is $75,000 whereas national reproductive health organizations may have millions of dollars to work with, Hernandez said. Meanwhile, abortion funds can typically aid just one-fifth to one-third of people who call looking for assistance.
For people interested in supporting abortion funds, Hernandez recommends joining and paying dues to their local fund as well as donating to the funds impacted by the most recent bans.
“Policy and litigation strategy is not enough,” Hernadez wrote. “People need abortions today and the people served by abortion funds deserve an invitation into our movement to fight back in their own voice.”