Where to begin. This is such a complicated topic, and I thought to myself: “Just don’t get involved. Just get on with your life. You are married. You are pregnant. You aren’t even a founder anymore — why post this?”
But the last week has been really triggering for me, and I need to write this for myself and for anyone else for whom it may resonate.
First, let me say that most people know me as an opinionated, outspoken, tough as nails, “I don’t give a f—-” kind of person. Some of what I’ll share in this post is nearly paralyzing to write down, let alone post on the internet, particularly when my “honest” blog posts have a tendency of going viral. Some of what I might say may also be unpopular or difficult to hear.
I want to say to anyone reading this that I really don’t have the emotional capacity right now to be bullied, so please be kind and compassionate when you respond.
‘When you see stories of women saying they met investors at hotel bars and late at night, this is why.’
In 2011 I cofounded Unroll.me in New York City. After we got the company off the ground and out into the world, I decided to move out to Silicon Valley solo to work on the startup that was my true passion, Archively. At the time, I had almost no connections in SV, and I had no idea what I was doing.
I had started Unroll.me with cofounders who had secured funding, so starting something alone was a wildly different experience. I had befriended a founder of a VC-backed startup who really believed in my vision, and he told me to go pitch VCs. No cofounder, no engineer, no product. Pure blue sky. He was convinced with the right introductions I could raise $2 million, sight unseen. Let me give you a minute to laugh.
So because I had zero — and I mean zero — idea what I was doing, I went with it.
He gave me books to read, helped me with my deck, and helped me practice my pitch, and then he made intros to VCs like Redpoint, Battery, Trinity, Kleiner, and Norwest. I will say this: To their credit, they all met with me on his recommendation. They were all incredibly respectful and genuinely engaged with me about what I envisioned.
I never felt any condescension. And there was certainly nothing said or done that was inappropriate. Now, clearly, I did not raise my $2 million on a blue-sky dream. Looking back, I am kind of embarrassed I even had those meetings, but what I learned over the next few years was that those meetings are incredibly hard to get. I was lucky, in a way.
So after I didn’t raise that money, I had to figure out how to do it on my own. I was super scrappy and bootstrapped for a year. I tried to network and figure out how I was going to raise money — if I even could — while also trying to build something as a nontechnical founder.
Having spent over a decade as a headhunter on Wall Street, I consider myself a professional networker, and I found networking in Silicon Valley very hard. There is no central place to meet people. It’s elusive. It’s all about the back-channel. You rely on founder friends and parties, which can be equally elusive, mostly to get access to investors and helpful people.
So when I happened to meet a well-known angel investor through a friend at a restaurant one night, I was super excited for this casual, warm intro. We exchanged numbers and texted back and forth trying to make plans to meet up for drinks. I spent my 20s in bars recruiting traders, so “bar business” was not new or intimidating to me.
I ended up meeting him at 10 p.m. one night. So when you see stories of women saying they met investors at hotel bars and late at night, this is why. It’s so hard to get meetings and raise money that you are willing to meet wherever and whenever to get some air time.
But here is where I have to be really honest with you and myself about what happened.
‘There was no “Yeah, come pitch me; I’m interested in your company.” I made that up in my head.’
I had an agenda, but it was not a shared agenda. I was the one who decided this was a business meeting. At this point, I still hadn’t raised any money, but I had a prototype, and I felt more confident pitching. Using femininity to get male attention in business was not new to me, and I had zero shame in using it. Shortly after sitting down, it became pretty obvious he was just hanging with me as a woman who happened to also have a company.
There was no “Yeah, come pitch me; I’m interested in your company.” I made that up in my head.
I still tried to talk business, but it was not a focused conversation, and more drinks were poured. Then he said, “I’m taking you home with me tonight.”
I think I laughed and said, “Oh, are you?!”
But after a few more drinks, I made a consensual choice. I said OK but followed it up with a clarification: “But then you can never invest in my company.”
I don’t think he really cared.
Honestly, I didn’t see as a big deal until now. Why not?
‘Culturally, we are taught as women that our main power is our looks and sexuality.’
When I started my career as a headhunter more than a decade earlier, cold-calling traders on Wall Street, I used to take them out for drinks. This was how I did my job. I was not naive or innocent. It was certainly not the first time a guy ever hit on me.
In the early part of my career, guys would say to me, “You have such an incredible voice on the phone that I had to meet you to see if you were hot.”
San Francisco. Robert Galbraith/Reuters
Wonderful. Eye…