Trail running

A meditation on being a startup founder

It’s been almost 20 years and I still remember the dread of Mile Day in high school gym class: four terrible loops around the track, greeted at the graceless end by the rest of the class long awaiting us, some of the cool popular athletic girls laughing in that mean girl way at the misery of the final finishers.

Last week I went out with no particular training and hit an 11.5 mile rocky trail run through the desert, up 1600 feet of elevation gain. One thought kept drifting through my mind as I pushed through the sand and gravel and rocks: A mile on this run is so much harder, and in so many ways I didn’t even know it could be harder! than a mile on one of those synthetic rubber tracks, but damn am I feeling so much stronger and more powerful and yes it still sucks and I’m hurting but I’m going to make it.

It reminded me of a cartoon I saw in a diversity & inclusion workshop a long time ago. There are two runners at the starting line of a race. One, to the left, is in his running uniform and cleats, sprint position, ready to tear down a smooth track lane. On the right is someone who doesn’t have proper athletic gear and is looking down a path that’s torn up, obstacles in her way, rain and weather adding insult and mockery to the course she’s about to run. Tell me, is it fair to compare their mile times?

In high school, in that artificial, controlled environment, we were all on the same track, close to perfect conditions for running our best. In the real world, in life, in work, it’s not so comparable. Some people are still on the track and others of us are out here on the trails. I think running is hard no matter what the conditions (“running never gets easier — you just get faster”), but I’ve learned it can be comically more difficult than I ever imagined. I’m going through unknown terrain, under hot desert sun, on a path so poorly marked and mislabeled I keep losing it, up rocky inclines, through dried out river washes that sap my energy as my feet keep slipping through the sand and gravel, dodging accidental cactus pricks, just barely avoiding face-plants when my shoes catch against rocks, the strap of my hydration vest rubbing against a blistered bug bite.


I feel like I’m doing a miserably tough trail run version of the startup founder race. Of course startups are always hard. But I’m a solo female founder, working on a problem that most of the gatekeepers of capital and power neither understand nor empathize with. I’m an activist trying my utmost to dismantle those systems of bias and privilege that have elevated them and kept them floating in those roles. As a competent and experienced software engineer in my own right, I also threaten some people’s notions of what a woman in tech might be capable of. Anticipating the reply guys who’ll come along to tell me it’s unbecoming of me to be sure of my worth, I will not enumerate all the ways in which I am outrageously better than most of my peers and yet still am treated with far less respect or even outright disrespect.

I have been sexually harassed during fundraising. I have had different investors inquire about my age and relationship status and tell me about their first time having sex. In roomfuls of men, I have been completely ignored and talked over, despite being the expert in the room. Although Twitter is the water cooler of the tech industry, on that platform being a woman of color with an opinion and a minor following means I deal with harassment every day, some drive-by, some extremely targeted and persistent, spanning 6+ years by this point. I get racism, misogyny, sexually explicit threats, links to Asian porn, incoherent and disturbing professions of love, conspiracy theories involving me and a former FBI director, all sorts of anonymous heroes just letting me know that I’m off-putting to men and I would be more attractive and dateable if I weren’t so angry. I have been stalked in real life and then gaslit by law enforcement and private security firms trying to make me feel like I’m self-obsessed.

Over and over I’ve had men who purport to be advocates of diversity & inclusion try to take advantage of me and my company, costing me months of invaluable time, attention, and energy, not to mention so many tens of thousands of dollars in legal fees, billed by the 6 minute increment. One, I discovered later, has a pattern of using his position of fame and wealth to prey on female founders, I suppose because we are more vulnerable. A potential co-founder, after negotiating vigorously for special terms that I almost acceded to, accidentally emailed me his diary full of unflattering and coded sexist thoughts about me, wondering if I would be able to step up to the role of CEO. Another job candidate sent repeated emails after a bombed interview and subsequent rejection berating me for making a huge mistake and not seeing that he would be a huge asset to the team and telling me I was a bad interviewer anyways.

The stories go on. It’s a lot of abuse to take, in so many different forms.

Through all of this, I’m just trying to build my company. The great irony is that everything I’m trying to do directly addresses the adversity I’ve had to face and stare down. The tech industry’s dearth of diversity, ethics, and accountability has led us to a place where our real and digital worlds are rife with harassment, and disproportionately women, minorities, and other marginalized groups bear the brunt of it. I started my company not only to give people a safer experience online, to empower them and protect them from bullying and abuse, but also to attempt another existence proof for a company run by a woman, with a diverse team, that prioritizes the well-being of our users.

The people who care most deeply for me ask me if it’s worth it to put myself through all of the pain, suffering, and stress. But how could I not? I’m one of the few that even has the privilege to try. I am immensely lucky to be able to do what I do. And my crucible of experiences makes me uniquely suited and determined to solve the problems I’m trying to solve.

I was never a gifted runner but by force of will and perseverance over decades I can now casually do the kind of trail running that I once thought sheer impossibility. The rocks, the hills, the sun, the heat, the dehydration, everything that makes the running a challenge is that much more a reminder that I’m alive and it’s glorious to be able to move through this beautiful world. And it’s that same endurance and brutality of training that I trust will make me stronger, faster, and more resilient as a founder, an activist, and someone trying to make a little bit of positive difference.

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