Faking it in the Valley

A highly sensitive pessimist tries to raise millions in Silicon Valley

Welcome to a three-part story about fundraising in Silicon Valley as a sensitive woman. Watch for Part II next week!

Before we start, I want to introduce an important character (and real person!), Steve, who was my co-founder and partner in the trenches. You can read Steve’s imaginative, captivating and eclectic writing over on Medium. Don’t worry, you will not find ten tips on running a successful startup 🙂

Illustrated by Stephanie Davidson, written by Rae Katz

PART I

When the startup was five months old we decided to raise two million dollars. We came up with this number through the rigorous and time-tested Silicon Valley approach of…sensing the market vibes. Right then in the Valley, the vibes were good for infant companies raising money on an idea, if you had the right ingredients. The founders mattered a lot, the potential market size mattered a lot, the content of the idea mattered somewhat, and what actually had been built to date mattered very little indeed. It goes without saying, but whether the company would ultimately help or hurt individual people did not matter at all.

Because the founders themselves mattered so much, we were, in many ways, selling ourselves. The best founders had already started and exited a successful company–“exit” being the Silicon Valley word for cashing in via acquisition or IPO. Neither Steve nor I had done that, but even at the age of twenty-seven, we had the professional swag to craft a pretty legit-looking founder bio slide (and the slide, really, was the thing). We had graduated from Brown. Steve had worked at IBM Watson and then helped start IBM Design, a massive corporate initiative to bring design to IBM’s software. I had won a Fulbright and worked at McKinsey. These things were largely irrelevant to what we were actually trying to do, which was starting a healthcare technology company, but we were going to throw all the glitter in their eyes to help them forget that. Don’t get me wrong, we did have certain skills, gumption and a proven ability to win highly exclusive spots in the world. But we had not done anything similar at all to building a healthcare technology company, nor did we have experience with almost any of the component parts of that effort: Marketing a healthcare product, doing marketing at all, selling to healthcare executives, doing sales at all, working with lawyers, managing contracts, hiring people, managing people…I mean, you get the picture.

I am tempted to portray this as a negative thing: look at these little asshats going out for two million dollars to do something they have no experience doing and haven’t even started actually doing yet. Look at them getting money thrown at their feet because of their immensely privileged station in the world. (This would be my preferred telling, as I am a hardened Silicon Valley cynic.)

But also, the belief in this crazy place that a person can do anything he puts his mind to does bestow a sort of superpower. Imagine you wanted to become a Christmas tree farmer, or a chemist, or that you wanted to start a commune. Now imagine that, regardless of having absolutely no experience whatsoever in your chosen field, you really believed you could do it. What kinds of things would you try?

I knew a bit about this superpower from observing Steve throughout our college years and into adulthood. He was someone who I had long admired for his ability to put his mind to something crazy and do it, more than anyone else I knew. In college, Steve started a conference for designers and engineers to collaborate on social impact projects. After college, while working full-time at IBM, Steve started the magazine Makeshift, soliciting articles from global contributors about people innovating in resource-constrained areas. My impression is that his power to just do things was partly innate and partly formed through early experiences of taking creative risks and seeing success. When Steve was in middle school, he started a Family Guy fan website and grew it to be the number two Family Guy fanpage on the internet. He is, and seems to have long been, an entrepreneur in the truest sense: someone who has wild ideas about what he wants to see in the world, and who makes them happen. The belief in the Valley, I’ve come to see, is that people like this can in fact start a company where they don’t know shit about shit, can learn quickly and adapt and bring new creative ideas to the endeavor, and, once in a while, they can be very successful at it.

I was not one of these people. I was very good at applying to highly selective organizations, and I was very good at doing homework, and I was very good at exams. I was highly practical in my evaluation of what is possible in the world, I was somewhat risk averse, and I leaned pessimistic. In this way, Steve and I complemented each other well, him pushing us outward into the world of wild ideas, and me pulling us back into the world of real constraints, meeting somewhere in the healthy middle. We both credit our success to this pairing. And yet, my role was not fun. I hated my role. Surrounded on all sides by people who seemed to just think big and feel inspired and believe, I plodded along saying, “no, well, we can’t…” and “I don’t think that’s realistic…” and “that growth seems unachievable…”

Steve and I did, eventually, both have to learn the ways of the other in order to make the thing work. At some point Steve got so far into the details of our product that he was the one warning me about what was unrealistic. And eventually I did learn, in the great meat grinder of Silicon Valley, how to believe I could do things I had never done with no real evidence to back up that belief. But that would not come for a long time.

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So we were going to raise two million dollars. It was early June, and we had heard that VCs vacation in August, so the clock was ticking. Our effort began with outreach to everyone we knew who knew people, asking to be connected to the kings with the cash. Because we did have our diamond-studded corporate track records, we were able to get to the VCs within two degrees of separation.