Cindy Gallop, advertising executive turned multi-hyphenate entrepreneur, has built her whole career out of memorable statements. An outspoken advocate for more open attitudes about sex, she founded her first tech startup, Make Love Not Porn, in 2009; this year, she created her own fund, All The Sky Holdings, to help other “Sextech” companies get off the ground. Here, she talks disruption, workplace harassment, and why trust makes businesses successful.
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ON CHILDHOOD: I am the antithesis of my upbringing, in many ways. My father is English, and my mother is Chinese. They met in Singapore, and I was born in the U.K. When I was six we moved to Brunei, where my father got a job, and my mother subsequently taught and then started her own school. It’s a very small, orthodox Muslim country, and we never talked about sex at all. My parents are very old-fashioned. My mother was a “Tiger Mother” par excellence, and my childhood was characterized by extreme academic pressure.
I’m the eldest of four sisters. We’re close now, although we’re all very different. As the oldest child, I was expected to conform to my parents’ vision for my future. My father didn’t take a typical career path; he cut sugarcane in the fields of Australia, traveled with a carnival, motor-biked across America, and worked on a farm. When he found himself back in the U.K. with a wife and two small children—me and my sister Annabel—and no way of getting a decent job because he had no university degree, he drove a van delivering groceries and studied for an English literature degree. As a result, from the moment I was born, I was told that I was going to Oxford—taking the traditional path. I had no choice whatsoever; it didn’t matter what I wanted to do. It was, “Get to the top of the class or don’t come home.”
That being said, I did get into Oxford, and the moment I set foot there, I was so grateful to my parents. To spend three years at Oxford studying English literature was a privilege, and it’s opened doors for me ever since. Oxford is where I fell madly in love with theater. I wrote, acted, directed, stage-managed, and was president of the Somerville Drama Society, and from there, I became a publicist and marketing officer for a number of theaters around the U.K. However, after several years of doing that, I was fed up with working 24/7 and earning chicken feed. Part of my job involved giving talks about the theater I worked for, and after one of those talks, a woman came up to me and said, “Young lady, you could sell a fridge to an Eskimo.” So I thought, okay, that’s the universe telling me something: Time to go into advertising. So, at 25, I did.
“I was told that I was going to Oxford—the traditional path. I had no choice whatsoever; it didn’t matter what I wanted to do. It was, ‘Get to the top of the class or don’t come home.’”
ON STARTING HER CAREER: In London in the mid-’80s, it was very, very difficult to get into advertising, because it was the sexy industry that everybody wanted to work in. I took a drop in salary to start at the very bottom of the ladder. But that was fun, because I knew I’d make it up pretty quickly, which I did.
I’ve been lucky enough to work in male-dominated environments where I did not encounter, to the same degree, the appalling sexual harassment that has affected many women across every single industry. And by the way, I did encounter harassment—back then, that was the norm. But I didn’t experience it in the career-destroying way that many women have, so I was lucky. And I was also fortunate to work for male bosses who saw my potential, championed it, mentored me and were fantastic role models. There is that saying, ‘The harder I work, the luckier I get.’ And I think that is true, but unfortunately, being great at your job and working hard is not enough. Sometimes it really is pure luck that you end up in an environment that allows you to flourish.
ON TRUST AND SUCCESS: There is a formula for success in business, and it goes like this: You set out to find the very best talent in the marketplace, and then give them a compelling and inspirational vision of what you want them to achieve for you and the company. Then you empower them to achieve those goals using their own skills and talents in any way they choose. If, at the same time, you demonstrate how enormously you value them, not just through compensation, but also verbally, every single day, and if you enable that talent to share in the profit that they help create for you, you’ll be successful. It’s so simple, and virtually nobody does it, because it requires a high-trust working environment, and most business environments are low-trust. In order to own the future of your business, you have to design it around trust.
ON AGE AND SEX: I tell everybody my age, which is 57, as often as possible. I consider myself a proudly visible member of the most invisible segment of our society, which is older women. I want to help redefine, in the way that I live my life, what society thinks an older woman should look like, be like, talk like, work like, and fuck like.
I date younger men, and about ten years ago, I realized that I was encountering the convergence of what happens when today’s access to hardcore porn online meets our society’s reluctance to talk openly and honestly about sex. These two factors result in porn becoming, by default, sex education—and not in a good way. So I put up a tiny clunky website, MakeLoveNotPorn.com, that balances the myths of hardcore porn with reality—the porn world versus the real world. When we launched at TED in 2009, the talk went viral. I realized I’d uncovered a huge global social issue, and saw an opportunity to do good and make money simultaneously. I turned MakeLoveNotPorn into a business, into MakeLoveNotPorn.tv. We are pro-sex, pro-porn, and pro-knowing the difference. We’re building a whole new category on the internet that has never existed before—social sex. MakeLoveNotPorn is about socializing sex, and capturing what goes on in the real world, as it happens spontaneously, in all its funny, messy, glorious, silly, wonderful, beautiful, ridiculous humanness.
Our key mission is to help make it easier for the world to talk about sex. It’s an area of rampant insecurity for every single one of us, no exceptions, all around the world. We all get very vulnerable when we get naked, and the sexual ego is very fragile. Therefore, people find it difficult to talk about sex while they’re actually having it. They are terrified that if they say anything, they will potentially hurt the other person’s feelings, put them off, derail the encounter, or ruin the entire relationship. But at the same time, everybody wants to be good in bed, and will seize upon cues for how to do that in any way they can. If the only cues you’ve ever seen are in porn, then those are the cues you’re going to take, to not very good effect.
“I tell everybody my age, which is 57, as often as possible. I consider myself a proudly visible member of the most invisible segment of our society, which is older women. I want to help redefine, in the way that I live my life, what society thinks an older woman should look like, be like, talk like, work like, and fuck like.”
ON “DISRUPTING SEX”: I’ve been working for the past two years to try and raise just $2 million for MakeLoveNotPorn to scale, which is not a huge amount of money in the tech world. When you understand what we’re doing and why we’re doing it, no one can argue with it—the business case is clear. But in the area of sex, people are still afraid of what other people think, and that has been my biggest obstacle. So I began to define and pioneer my own category, Sextech, which is any form of technology or tech venture designed to innovate, disrupt, and enhance any area of the human sexual experience. I did that for two years, and I’ve still failed to raise the $2 million. So, about six months ago, I realized that in order to fund my own startup, I had to fund the entire category. So I’m starting the world’s first and only Sextech fund. Now I’m not just raising that $2 million for MakeLoveNotPorn, but also $10 million to start my fund. Anything good in business only ever happened to somebody who went, “I don’t think I’m qualified to do this. I’m going to do it anyway.”
The name of my fund derives from a quote by Chairman Mao, who famously said many years ago, in the interest of gender equality, that “women hold up half the sky.” I think that’s relatively unambitious, and so my Sextech fund is called All The Sky Holdings. My fund will have a primary focus on radically innovative Sextech ventures founded by women. The most interesting things in sex are coming from female founders, and when you tap into that huge primary market, you also tap into a huge secondary market of extremely happy men. I want to be very clear on this: Yes, MakeLoveNotPorn.com and All The Sky have enormous social benefit, but I am also out to make an absolute goddamn fucking shit ton of money.
ON WOMEN AND INNOVATION: I say to every woman, “You just set out to make as much money as possible, because we don’t get taken seriously until we get taken seriously financially.” Also, when you’re a woman and you make an absolute goddamn fucking shit ton of money, you can then fund other women. You can donate to other women. You can support other women. In a tech landscape where female founders get 5% of all venture capital and 95% goes to men, we need to create our own financial ecosystem to lift women up.
Diversity drives innovation. At the top of every industry today, you have a closed loop of white guys talking to white guys about other white guys, and the product you get from that closed loop is Batman versus Superman. When you invite women and people of color into “The Room Where It Happens,” what you get is “Hamilton,” which has not only exploded every creative convention of the Broadway musical, but—and this is not coincidental—is also currently making billions of dollars. There is a huge amount of money to be made out of taking women and people of color more seriously.
“I say to every woman, ‘You just set out to make as much money as possible, because we don’t get taken seriously until we get taken seriously financially.’”