The Cake

I Tried to Build a Social Justice Startup. It Was Tougher Than I Thought.

My dream of creating a sex education platform proved to be complex and contentious

Photo: Klaus Vedfelt/Getty Images

As a queer woman of color, I’ve long regarded my work as a founder and entrepreneur in the straight, male world of tech as a form of activism. But I also knew I could do more. So after successfully co-founding my first company, the accounting software InDinero, I wanted my next project to focus more directly on social justice — specifically sex education.

I’d been raised in a working-class immigrant household that was deeply religious. My own sexual development was suffused with shame and stigma, and I knew that if I could reach outside the progressive bubbles of New York and San Francisco, I might save future generations from the trauma I experienced.

As a woman, I understood the need. As an entrepreneur, I saw an opportunity. As an activist, I saw a way to lift up a community.

I raised a small amount of initial capital, and in 2017, with a team of queer women and women of color, I set out to build a platform called O.school — similar to YouTube or Twitch — with which local, community-based sex educators could reach a global audience. Hundreds of millions of people would be able to learn from and chat with live educators anonymously.

Knowing a startup’s culture forms early, I immediately began reaching out to queer and nonbinary educators, educators of color, sex-work educators, educators with disabilities, and other educators of varied cultural experiences, inviting them to use the platform.

In bringing in members of a community that is often marginalized, there were unexpected challenges. Many educators were good and wanted to stream, but didn’t have functional internet. Others weren’t familiar with the complexities of live streaming. We trained people, helped them through their internet issues and, in one case, purchased them a new computer.

As anyone who’s founded a startup knows, everything about the first phase of development is theoretical, a bold experiment.

O.school’s initial revenue model supposed that educators would generate revenue from tips. We would then split the revenue with the educators, using our portion to market the platform so that educators would have larger audiences — and so that educators would make more money. It wasn’t meant to be collectivist, but it was meant to be sustaining.

But as anyone who’s founded a startup knows, everything about the first phase of development is theoretical, a bold experiment.

O.school’s launch received a lot of positive media attention, both for the subjects we were covering and how we were doing it. But a few months in, we discovered the audience still hadn’t reached a level where it could sustain the educators while we grew.

So rather than split tips, we gave educators 100% of the tips that came in. We wanted to encourage participation, so any educator who was reasonably adept at streaming — or working with us to get better — was given performance bonuses. Those who streamed with us with any regularity made at least $30 per hour, and many made much more. We also paid for feedback and emotional labor.

Many of my investors thought this was the wrong move. But I knew what it was like to struggle, and, as an activist, I was determined to bring the community with me. Our initial months were exciting. We were greeted with wide acclaim and had users streaming in from across the globe. Our educators were really helping people and were proud of their association with O.school.

By spring, however, there were signs that despite our shared goals, I’d underestimated the difference between the startup ethos and a social justice ethos.

I obsessed over scale, speed, and achieving the biggest possible impact, while they focused on process, ideology, and stakeholder consensus. At times, it felt like we were speaking completely different languages. Words like transparency, impact, collaboration meant different things to each of us.

I was humbled by how little I actually understood about sex educator and activist communities and was reminded often that, while our goals were the same — the elimination of shame and stigma around sexuality — our paths to getting there weren’t.

Most of my team and I had worked only in fast-paced, early-stage startups, so we had a very high tolerance for imperfection, uncertainty, and making hard decisions. I was also privy to information they weren’t: Behind the scenes, we were fighting to stay alive. We were almost always out of money, and the money we had was always prioritized to pay educators.

I was caught off guard when some educators voiced concerns that not everyone was earning the same amount, and wanted full transparency on payments. This was central to an activist ethos, but as the CEO, I struggled to understand how to put it into practice. I wasn’t trying to hide anything, but I had questions about how to manage consent and privacy — those who were performing better or doing intense work were making more.

There are many ways we could have addressed these situations better — such as reaching out to each person individually, to hear and be heard — but the honest truth was I often had to focus on making sure we survived the next week.

I saw my fight to keep O.school alive as a form of activism, as a natural change in the lifespan of a startup. They saw it as a betrayal of community ideals.

In May 2018, we did what struggling tech companies do. We pivoted. We cut back on the number of streams, focusing instead on generating the traffic that might eventually make them financially sustainable.

The fallout with the community was swift. My commitment to social justice was questioned. Slack discussions suddenly appeared on social media and tagging replaced conversation.

I saw my fight to keep O.school alive as a form of activism, as a natural change in the lifespan of a startup. They saw it as a betrayal of community ideals.

If I was going to have an effect on billions of people, I didn’t have the luxury of ideological purity. Raised in a working-class immigrant family, I know what it’s like to be practical. Whether in business, activism, or sex, purity shouldn’t be used as a tool for shame.

Eighteen months later, O.school is stronger than ever. By focusing on evergreen, search-friendly, medically accurate, stigma-free written and video content, we’ve attracted over 1 million visitors each month — the type of traffic that could once again make workshops viable. By experimenting with new models, we’ve learned to survive and thrive.

The central mandate of the tech world is that we break things. That we have to fail in order to succeed. But in bringing in a community that lived outside that ethos — that worked often in a collaborative, nonprofit space — I had exposed them to more risk than either of us initially understood.

Should I have been more cautious? Perhaps. But I don’t regret bringing communities into a vision early on, even if neither of us was fully prepared. What I do regret is that miscommunication over strategy could become a political schism — one that, once it started, shut down all conversation in favor of social media blasts.

A year and a half later, I’m grateful to those who have stayed with me to continue the fight. I still hope to find ways to bring back those who feel I initially fell short. But I know that activists, like founders, are strong-willed and independent-minded. That’s their power. Mine is to continue the original work O.school set out to do, while always keeping my door — and DMs — open for those who want to invest in the future.

founder/ceo at O.school. previously: venture partner @500startups. co-founder @inDinero. she/they. QWOC.

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