The first time I ever pitched an investor, I chickened out when the time came to ask him for money. I was a brand new founder, the freshly-appointed head of a company that existed mostly as an idea in the minds of three 24-year-olds, and the investor was a well-known VC visiting Detroit’s nascent startup scene who, in retrospect, had probably only agreed to hear my pitch to humor his tour guides. I stammered through my half-baked explanation of what our company was going to do and then, nearing the end of the meeting, froze. What was I supposed to do now? Just come out and ask him for the money? I flashed back unwittingly to my first experiences with girls as an early teenager, to all the times I’d been with someone and understood that this was the kind of situation that could lead to us kissing, but had been at a total loss about how to actually get from here to there.
In the end I just thanked the investor for his time and then shuffled forlornly out the door. And I cursed myself in my head exactly the same way I’d cursed myself back when I’d been too shy to kiss Izzy and Allie and Leah.
I did eventually figure out how to ask for the money. Most founders eventually do to one degree or another. Of course, the true fundraising masters will tell you that you aren’t asking anyone for anything. You’re offering them the incredible opportunity to invest in your fledgling company, which is sure to be successful beyond what either of you can imagine. Whenever I was scared to approach an investor, I’d try to imagine a future where my company had succeeded beyond belief and everyone who’d gotten in early had become a kajillionaire. In that world, this person might actually be mad that I hadn’t asked them to invest. The logic of that made sense, but deep in my core it was impossible to believe, not when we were kids with no experience and no idea what we were doing. If the company did somehow end up wildly successful, I knew it would be as much or more thanks to sheer luck than because of anything we’d intentionally done.
Fundraising, like an actor’s audition, is brutal because it’s mostly an exercise in continuing on no matter how many times people tell you no. Insanity is doing the same thing over and over and expecting a different outcome, but that’s basically what you do when you’re raising money. This process tends to select for people with-than-average higher levels of pain tolerance, and of semi-delusional self-confidence. Another similarity with auditioning is that fundraising, at least in the early days, is largely a performance. A mature company will have a history of real-world results to point to, but a new one is mostly just pitching a story. And since the business itself barely exists yet, the story is mostly about you.
I learned, over time, to play the part, no matter how I actually felt inside: to ooze enthusiasm, to radiate confidence, to pretend I was an old hand at something I’d just barely figured out how to do. Sometimes, I would pretend I was an actor playing a character, one who was impossibly charismatic and destined for inevitable success. Like the time when, in the middle of raising our seed round, I went backpacking in the wrong socks and came home with an infected blister. After a trip to the ER and an antibiotic shot in the ass, I rushed off to an investor meeting and stumbled in on my crutches fifteen minutes late, hospital bracelet still wrapped around my wrist. I was worried I’d already blown it, but the VC I was meeting with ate it up—“Coming straight from the ER, now that’s persistence!” So I kept the bracelet and the crutches and showed up ten minutes late to all the other meetings I had that week, breathlessly explaining each time that I had just come from the hospital. It was close enough to the truth that I never felt bad about saying it. But I can also see how that kind of white lie can be the first step on a path that ends with you becoming Theranos.
The thing about pretending to be confident, though, is that eventually you lose track of where the pretending ends and the real you begins. “Fake it till you make it” has been used to excuse all sorts of bad behavior, but there’s a simple and very real truth at its core: our brains are justification machines, and they don’t like contradictions. If you act a certain way long enough, you will eventually feel that way as well, because your brain simply can’t handle the dissonance otherwise.
Getting a few wins under your belt helps too. When someone tells you they’ll invest millions of dollars in your idea, the elation feels better than almost all of the other highs I’ve tried. It feels so good that it usually makes up for the hundred people who said the opposite—or, worse, ignored you entirely—the day before.
When I first started out, I assumed that when fundraising was going well, it would feel better than when it was going poorly. And it does, to an extent. But one of the paradoxes of startups—really, I think, one of the paradoxes of life—is that the emotions that come with success are not necessarily better or easier than the emotions that come with failure. Although I was proud of myself for eventually becoming “good” at fundraising, there was still an underlying emotional dissonance there that unnerved me if I looked at it too closely. Was it actually a good thing that I could pitch my company confidently even if I’d been feeling despondent about our future just moments before I stepped through a VC’s office door? Was the ability to broadcast an emotional state totally different from the one truly present within me really a skill I wanted to keep getting better at?
I never got the chance to find out. The company failed, though not for lack of money; we lost faith before the investors did. Even in our dying days, I was still lining up new ones, ignoring my doubts and trying not to think about how unnerving it was that I was still able to raise money for a company I wasn’t even sure I believed in anymore. As a founder you’re constantly trying to evaluate your circumstances realistically, but you also know that your irrational belief in yourself and your company is one of the most valuable assets you have. Holding both of those things in your head at once is an impossible balancing act.
If you’d asked me a couple years ago if I had been good at raising money, I would have answered with an unqualified yes. And to a certain extent, I suppose I was. But as more and more time goes by, as the person I was back then becomes more and more of a stranger, I’ve started to wonder if maybe, just maybe, I was doing it all wrong.
Perhaps my conviction that I had to play a certain part to succeed was just my same old insecurities lying to me the way they always do—and perhaps every investor I ever met with saw right through my act anyway. Perhaps the solution to my inner conflict wasn’t to paper over it but to face it straight on, to dig in and address it at the root. Perhaps when I felt like a fraud in those pitch meetings it wasn’t just imposter syndrome but rather a sign that on some level, deep down, I knew this wasn’t what I was supposed to be doing with my life. Or perhaps that’s all just crazy bullshit I tell myself in an attempt to draw some deeper meaning from what was, in the end, just my having been a bit player in some rich people’s decisions about how to allocate their assets.
But I think about dating, and about how much I’ve changed the way I approach it in the past few years. These days, aside from standard-issue manners, I don’t really worry too much about making a good impression. Whether consciously or not, I used to think of dating as a game, where you “won” by getting the other person to like you. I eventually became quite good at that game, but it turned out that getting strangers to be superficially drawn to me didn’t actually help me find what I was really looking for. Now when I’m on a date, I more or less just throw my hands up and shrug. This is the deal, I say. Take it or leave it. And I’d like to think that if I ever find myself raising money for another company, I’ll do it much more like that.
Yours in wondering if maybe I shouldn’t have used the real names of those girls I was too shy to kiss in high school,