Trust Me That It Matters When A Female Entrepreneur Wears A Low-Cut Top


“I’m looking for an investment in my world-changing business idea. A $10 million investment now could be worth $1 billion in five years.”

“You’re very pretty. Here’s a giant bag of cash.”

Okay, it doesn’t really happen exactly like that, but most female startup founders I admire can tell stories of variations on that dialogue. I know it all too well myself. No matter how severe and professional a woman entrepreneur dresses and behaves, those who get complimented on their looks are the ones who so often seem to rocket to success.

The divide in how entrepreneurs are often treated by investors based on gender and physical appearance isn’t a new revelation. The relative lack of women investors and a certain old-fashioned (meaning sexist and crude) attitude among many male investors creates a vicious cycle.

Arguments over whether this is something that women can control is really beside the point. Whether or not the charisma a woman exudes causes a man to picture a huge payout or to picture her naked, she still has to prove that her company is worthy of the investment. The most optimistic view might be that those investors should really study more of the humanities in business school if only to have the vocabulary to compliment a female professional without relying on complimenting her looks.

The pressures women entrepreneurs face because of how they are treated makes the already high-stakes investor meeting even more stressful. We have to constantly evaluate whether an investor is just friendly, or if he’s shifted to being flirty. Does he want to mentor us, or date us. What does he think that check is getting him?

Female entrepreneurs in Washington D.C. all too quickly learn some of the key codes to decipher this riddle. If the investor tries to set a one-on-one “meeting” at the high-end Quill bar in the Jefferson Hotel at nine p.m., he doesn’t want to see your profit projections. And it’s universally acknowledged that “let’s get coffee and discuss the future,” is how investors say “Netflix and chill.”

I’ve been tricked more than once myself. Invited to pitch an investor at his New York City office, I blew a huge chunk of my rent check on the next train from D.C., feverishly running the numbers in my pitch deck as I went. When I arrived at his office, I was told that the venue was changed to a members-only club. I gathered my optimism and went, but instead of complimenting my business plan and offering advice and investment, he spent the night telling me he thought I was beautiful and offering me drugs.

Alright, I was naive, but there’s sometimes no way of telling beforehand if you’re talking to a potential investor or just another self-indulgent business tycoon wanna-be who doesn’t understand the idea of commerce with women that don’t include sex. Maybe that’s a class they should add to Harvard Business School and Wharton.

“Cleavage Equity” and “Series C-Cup Funding.” No, they aren’t titles for Silicon Valley-based porn movies. They’re real terms I’ve heard thrown around in the venture capital world. A rational investor does invest in an entrepreneur that he or she believes has an excellent idea and knows what how to build a company. But rationality is not that common, and plenty of investors simply hop on a trend’s bandwagon or pick someone they like without thinking about the numbers. Finding the balance between being yourself and not letting investors see you as “the woman” is hard. You have to be mindful of appearance and think long-term.

You can’t change the system overnight but you can be part of the effort of change by calling it out when it happens and not keeping it a secret. I tell other women which men to avoid in business and the experiences that I’ve had so that the douchebags can’t get new vics. Keep your wits about you and focus on the beauty of the company. And a can of mace is always a comfort.