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YC's Jessica Livingston Was Hit On by a VC on the Way to This Interview

"One patting on the butt is one too many."

Nellie Bowles

When Jessica Livingston, a co-founder of the influential startup accelerator Y Combinator, arrived at The Wine Room in Palo Alto, Calif., a little early for our meeting, a man who was also waiting outside the wine bar started to chat her up.

He asked what she was doing there all on her own, and whether she was there maybe for a date. Livingston said that she worked in tech, and was meeting a reporter. He said he was an investor. She said she was, too; that she co-founded Y Combinator. He asked if maybe she had some startups in her portfolio that other investors had overlooked, and asked for her contact to set something up.

She gave him the name of YC’s male president, and said to talk to him.

When I arrived, Livingston said she was shaken, and apologized to me. The Wine Room was closed anyway, so we walked to a different bar across the street.

“I’m not crazy, right?” she said. “He was hitting on me? He was offering to invest in our weaker companies as a way to get me on a date, right? Did that just happen? Today, of all days. I just can’t believe it would be today.”

Livingston said she wasn’t sure if this man was just flirting, actually attempting to talk investments, or offering venture funding for a date.

It was supposed to have been a relaxing Wednesday afternoon for Livingston, whose newest fleet of 25 companies had pitched before investors at the Y Combinator Demo Day just the day before. We were meeting for a lighthearted conversation for my Two Drinks With column, and I was thinking that I’d call the resulting feature “Demo Day Detox,” but it didn’t seem like a good time for that.

What happened to Livingston outside the bar is the latest in a series of stories to arise with a depressingly similar pattern: Venture capitalists sexually harassing female founders (the few that exist).

Though YC has its own spotty history with gender issues, Livingston has taken a strong stand this week, with a statement against sexual harassment. She wrote on the YC blog: “Y Combinator has a zero tolerance policy for inappropriate sexual or romantic behavior from investors toward founders. Don’t even think about doing it. I will find out.”

Obvious though her statement may have been, it was at least something.

Livingston and I headed to a large beer hall called The Old Pro. She ordered a Hefeweizen, and joked that she might need a pitcher after what had happened. The waitress said she was sorry, and asked if everything was okay.

“I think so,” Livingston said.

She was wearing makeup, which she said she rarely does, and she wondered about the impact of lipstick.

I asked whether a man had offered funding in exchange for a date to her before.

“No, absolutely not,” she replied. “That’s not the culture of YC. It’s not a pattern with us.”

Why had she written that blog post banning sexual harassment?

“There are so many new investors coming into the Valley from New York and everywhere else, and we just wanted to lay that out there,” Livingston said. “The overt sexual harassment you read about — the men who say they don’t invest in women — I can’t force them to invest in women, but I can say you can’t sexually harass our founders. And so that’s what I did.”

Very few female YC founders have reported harassment, but it has happened. An investor sexually harassed Jamie Wong, the co-founder of travel site Vayable; she spoke about the incident at a YC female founders event. He had put his hand on Wong’s butt, Livingston said.

“It doesn’t happen to every woman,” she said. “But one patting on the butt is one too many.”

Livingston will be launching a site in the next month to help draw attention to the female founders within YC. She started to describe it, and then paused.

“I’m sorry,” she said. “I’m just still really shaken up. That’s never happened to me before.”

I said she shouldn’t worry. I told her about the time I was groped while attempting to cover a charity gala. We laughed about it. We talked about other things. We finished our drinks.

“The way I can be most impactful is by setting an example as a female founder, and by highlighting others. The best thing I can do is to make it look possible,” she said. “But my real passion is advising the startups.”

Livingston, who has two children (a 2-year-old and a 5-year-old), is a pretty big defender of startup culture. I didn’t bring up the concept of “brogrammers,” but she did, preemptively.

“There’s this huge misperception that [YC is] this brogramming community,” she said. “Do we fund more men? Yes. Do we wish we funded more women? Yes, we do. I’d love it if more women applied.”

Right now, it seems, everyone wants to jump into seed investing, hoping to discover the next Dropbox, a YC alum. Livingston said the new energy in startups is largely positive.

“I’m high on startups right now — and it’s exciting that they’ve become so mainstream,” Livingston said. “Though it also means there are a lot of inexperienced investors.”

Is there any way to educate investors?

“We used to do this thing called AngelConf. We’d get a panel of seasoned investors, and invite people who’d done well, maybe at Google, and wanted to start investing, and we just taught them the basics of how it worked,” she said. “Maybe we can do that again?”

It seemed like it might be a good idea.

I asked who the investor who had harassed her earlier in the night had been. She didn’t want to share his name.


“What if he wasn’t hitting on me? What if I totally misunderstood?” she said.

This article originally appeared on

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