Faking it in the Valley, Part III

The single, most critical, most supremely important, most life-defining day

This is a three-part story about fundraising in Silicon Valley as a sensitive woman, and I’m excited to finally tell it to you. Check out Part I and Part II, which people are calling “edge of the seat stuff,” “fascinating,” and “a wild ride!” and get ready to squirm with me as I try to make it to Y Combinator Demo Day.

“We are what we pretend to be, so we must be careful about what we pretend to be.” — Kurt Vonnegut

Illustrated by Stephanie Davidson, written by Rae Katz

PART III: The Finale

The days leading up to Demo Day included long hours at YC headquarters in Mountain View, practicing and editing and re-practicing our pitch, tweaking and re-tweaking minimalist slides, getting on long waitlists to try it out in front of the YC partners, getting feedback, and repeating. Two days before Demo Day I spiked a fever and developed sharp abdominal cramps, but I would not give up our place in line to practice pitching. So, head hot and with a sharp pain in my side, I got up on stage in front of two men reclining in plastic chairs and began with our slimmed down introduction to our company:

“We enable doctors to report on quality metrics so that they can get paid for keeping patients healthy.”

I continued through the blue and white slides, each proclaiming one large phrase or one large number, TED style. Founders milled around in the background, clustered in groups, mouthing pitches, stressed. Seven minutes later, when I had finished, one of the partners said,

“I still don’t get it.” This had been a theme. “Why is this important? Why does it matter?”

I tried to describe it again, differently, and the two men gave suggestions.

“Simplify the introduction,” one of them said, “like, you get doctors paid for keeping patients healthy, right? Say that.”

And so our already simple pitch was further simplified:

We get doctors paid for keeping patients healthy.

The reductiveness of the YC pitch formula is widely mocked among the Demo Day crowd: all the pitches end up sounding molded and formulaic, like someone took the same cookie cutter to all of the companies and out they came rendered in the same shape. But the formula nonetheless carried an important lesson: in this world, being specific and accurate was not rewarded.

Discouraged and sick, I retreated to my car with Steve. I reclined the driver’s seat of the beige 2004 Toyota Corolla that had previously belonged to my mom, and curled up there on my side. Being in that car, which drove me places in high school, was a small comfort. I lay there in pain, totally determined: I would do this damn pitch, and I would do it well; everything depended on it.

And on cue my body was responding: you won’t do this pitch, you won’t do it well, you will be hindered by your unfortunate physicality. 

But there was no question that I would push through. As we rested in the car, my abdominal pain hit a local maximum and I sat up and doubled over. It felt like something sharp had gotten stuck in my intestines, or like an organ was twisted. Steve suggested it might be gas. It was hard to believe, but I hoped. The wave of pain peaked and subsided, and I lay back again. We agreed I would stay there and lie down for a bit. Steve went back into the building to work on the slides.

We must interact with power carefully and with extreme humility, knowing we don’t have so much control over what we want.

The idea that I would skip Demo Day for a fever and mysterious abdominal pain sounds crazy to me even now. That is the weight this day carried. A founder is extraordinarily lucky to have chance at Demo Day, and you only get one seven-minute shot, and this lesson had already been so deeply instilled in me that I can barely imagine a scenario in which I would have missed it. That there may have been any other option—for our slot to get switched to the second day of the two-day event, for Steve to do the pitch—did not cross my mind. The night before our pitch, we stayed in an AirBnB in Mountain View, where I went to bed at 8 pm and lay on my back with my knees to my chest trying to pass gas. 

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On Demo Day, I woke and dressed in my black jeans and button-down. It wasn’t the standard YC Demo Day uniform—a hoodie or T-shirt with your company’s logo on it—but in an environment where I felt constantly tiny and insignificant, I felt I couldn’t afford to look young or sloppy. I blow-dried my hair and applied my makeup. We drove to the technology museum where the event would take place, and parked alongside hundreds of cars in a vast parking lot. Driverless golf carts scooted around the perimeter, demonstrating the technology from one of the companies in our batch.

Inside the large, bright entryway, the air buzzed with anticipation. Steve and I picked up our badges, and made our way into the dining area where two hundred founders were corralled, trying to distract themselves with conversation or standing in a corner nervously whispering pitches once more time.