Musings of a weary former CEO

My startup was like a leather Catwoman suit

Illustration by Stephanie Davidson

When I was a female CEO in Silicon Valley, I never felt like I was a strong woman, or a trailblazer, or an important representative of my gender, or, really, powerful at all in any way. This is interesting to me because all the ingredients were there: technically, I was a woman, I was the leader, I was doing things that mostly men do, like attending the illustrious Y Combinator incubator and raising coveted venture capital and, eventually, selling my company to another company for a bunch a money. All evidence would suggest that I was a woman leaning in. I can see the hypothetical article about me in my mind: there’s a header photo of me in a stunning slim-cut red jumpsuit and crisp white blazer, sporting bright red lipstick and a closed-lipped smile, set in the foreground of a bright office with soaring white ceilings and gleaming European white oak floors. The caption says something about how I spent all my savings to start the company and look at me now.

But that photo was never taken, and I never felt the way that a female founder in such a photo looks like she should feel—accomplished, powerful. I slunk away from my role as CEO with the same cowering posture that I held (mostly internally, mostly invisibly) for the whole life of the company. At the end of the day, I never felt good about the thing. Why is that?

The stories we tell

My cofounder and I were opportunistic about choosing our business—we wanted to choose something that was a good business. While this might sound like a good strategy for someone trying to create a successful business, it runs counter to the prevailing Silicon Valley approach, in which, ideally, a founder’s entire life story to date culminates in their startup idea, the seeds of which were planted in grade school, nay, in the cradle, and which idea has grown to consume this founder’s every thought and desire.

This was not how I felt about my company, but in order to play the game I still had to speak about it as if I felt this way. I spewed the required stories, but I didn’t believe any of it. I was doing this business because it seemed like a good business. And it, at least, did not seem harmful to the world. Full stop.

My writing partner, Alex Dobrenko of Both Are True hilarity, read a recent essay of mine and said, “why don’t you ever say what the startup did?” And I was like, “it’s a startup, who cares.” And he thought that was really funny. And I always feel great when Alex thinks something I said is funny, because he’s a comedian. But that’s beside the point. My response pretty much sums up my orientation towards the business: it was a business, who cares. It worked, in one sense, and it also ruined me, what more is there to say?

But to respond to Alex’s critique, here’s what we did: we built a software product for healthcare providers (like doctors and hospitals). They used the product to report data on healthcare quality to Medicare (the federal government). These quality reports are required, kind of like filing taxes, so you can think of our product like TurboTax for healthcare quality reporting (that really rolls off the tongue, I know).

You might wonder how I spun “TurboTax for healthcare quality reporting to Medicare” into a longstanding life dream, but I assure you it’s possible. My extensive experience with chronic disease led me to be deeply passionate about healthcare quality. I dreamt of being on the forefront of exciting new methods to improve the care given to patients. My mom is a doctor (yes, even my mom figured in somehow, please forgive me). The story was true-ish. I do care a lot about the quality of healthcare in our country. My mom is, indeed, a doctor, though I’m not sure exactly why that matters here. And my company was related to healthcare quality, technically.

But I never believed that my startup was really the best way for me to contribute to the project of healthcare quality, or even a very good way, if I really looked across the board at the options for contribution, if contribution to the cause was really my primary metric. My startup, in reality, was the best way for me to contribute to this project a little bit, while also starting a viable business in Silicon Valley and potentially making a lot of money, which quite narrows the scope of options.

I think this is important because it must be true of so many startup entrepreneurs, deep down. It just must be very rare to really find an overlap between one’s genuine dream and a genuine positive world impact and a great high-growth business. I think some founders are able to actually believe in their perfectly crafted founding story, but I wasn’t able to. And so rather than the story lending meaning to the work, the friction between what I was saying and what I believed created a world of pain. I have a sneaking feeling that this dynamic is probably at work in various ways for many knowledge workers in the burnout generation. Any article with a cover photo of me in said red jumpsuit would belie the reality that it all felt like an act.

This was more profound than imposter syndrome. This was not a situation where you fake it till you make it. This was a fundamental mismatch between what I was saying and what I was feeling. Leaning in to my CEO role, faking it more wholly—something I did for years—would only prove to make it feel all the more like a big lie. It is no wonder that this situation didn’t make me feel powerful. I rarely felt like a badass woman, and if I did, it was only in the pretend game way, the way you feel like a badass on halloween when you put on a full-body skin-tight black leather Catwoman jumpsuit (I would imagine, I have never done so). It’s not really you, but your costume lends you the feeling for a moment.

What would it be like if we could drop the save-the-world stories that businesses are required to tell these days? What if, even as we work to change the nature of business, we could be also more honest about what we are actually doing as workers at work? My guess is that even this shift in storytelling, though not nearly enough, would alleviate some of the generational weariness and moral injury that have consumed people like me.

Going forward, I will pay a lot of attention to the story I feel I am required to tell and whether it matches what I believe to be true.

—Rae