Before his hand would land on her, Emma Tessler was already silencing the alarm bells going off in her head.
They thought it had gone great: their app could take on the dating industry by doing the work of matching for you, instead of the constant swiping left and right, messaging and then hopefully a date.
After their pitch came the mingling and the small talk — and hopefully, the checks.
Tessler, the company’s co-founder and COO, approached an investor whom she had met earlier in the day. He was also from New York so he suggested that they go out for drinks when they were both back in the city. To a woman, that normally means a date, but Tessler quieted the alarm bells.
“I tried to pretend I was a man and think if I was a guy founder, I would probably think ‘Oh great. That’s an opportunity to talk to an investor more,'” Tessler said in an interview with Business Insider.
He put his arm around her, but she chalked it up to him being a friendly investor. But his one-handed hug had landed his hand on the side of her breast — right as he offered $US50,000 to invest in Dating Ring.
“There it was. The first offer I had gotten, and his hand was on my sideboob,” Tessler described in a company blog post on the subject this week. “For those of you playing along at home, that’s a man in a position of power, wielding his power by offering me money, and touching my breast.”
The struggle with sexism
The incident underscores the kind of thorny situations that many women in Silicon Valley’s booming tech industry face.
With start-ups raising vast sums of money at ever-increasing valuations, Silicon Valley is considered America’s capital of opportunity, a place where smart ideas and an entrepreneurial spirit can be the ticket to success. But for female founders pursuing the tech dream, the landscape can be fraught with troubling interactions that challenge easy definitions of sexism and lead to constant self-doubt.
The subtleties are hard to pick up on, and even harder to prove. Venture capitalist, now interim CEO of Reddit, Ellen Pao very publicly lost her gender discrimination trial in March after a jury ruled against her. While there is increased awareness about the challenges facing females in tech, progress can be difficult to gauge. A lot comes down to the grey area, the indecision and the questioning that a lot of females face.
Tessler and Kay, for example, are speaking to Business Insider and also published blog posts detailing their journey fundraising as females. Their startup is also the feature of a podcast. However, neither are naming investor names out of fear of labelling someone.
Self-doubt and guilt
On Dating Ring’s Demo Day, Tessler wasn’t sure what to do. People she confided in had the same “that’s messed-up” reaction, but she faced doubt and fears of over-reacting, she said.
“Whoa is his hand on my boob? What the hell? Oh Jesus it’s still there. He must not realise how far he’s wrapped his arm around. Yeah. What an awkward mistake to make,” she remembered thinking at the time of the incident.
“It was just a constant back and forth. I think it’s what a lot of women experience with a myriad of events,” Tessler said about her thoughts in the moment. “They think maybe this is normal behaviour. Maybe I’m being overly sensitive.”
Tessler, Kay, and another founder took a couple days to decide what to do before ultimately writing back to turn down the money. They said they were being strategic about which investors they were choosing to partner with.
That decision was not easy and led to a lot of self-doubt and worries that they may have deprived the young company of important momentum.
“I felt a lot of guilt about the idea of not taking the money because I felt this thing that happened to me is going to negatively affect the company, my cofounders and my employees,” Tessler said. “I felt like ‘oh what if I had walked away a little bit sooner, we wouldn’t be in this situation. I wouldn’t be in this position of denying my company money that would really help us.'”
The “easy to spot” actions vs. the subtle
After Demo Day, Kay took on the majority of fundraising work as CEO and started lining up calls with investors.
The result was only so-so. The company raised only $US455,000 in March and May 2014, and haven’t raised any money since. (Of that, $US100,000 was from Y Combinator and another $US100,000 had to be given back to an investor.)
“I had 40 fundraising meetings, I sent over 300 emails requesting meetings, and tried to get in touch with another 500 investors,” Kay spelled out in her blog post called “Fundraising While Female“.
“While it’s hard to ever know exactly why you’re being rejected by an investor — and while I didn’t want to blame any of it on my gender — by the end, I knew it had played a role.”
Kay has a few specific examples of being treated differently during the fundraising process: VC’s who invited her to events as personal invites, investors who described her as “beautiful” with “beautiful” cofounders. But to her the more pervasive problem is the subtlety of it all.
“It’s hard. I’m talking about a problem without a solution,” Kay said to Business Insider. “For me, the solution is so far away. This shouldn’t be something we still debate whether or not it exists.”
It’s not an excuse, just a problem
To be clear, Kay and Tessler do not blame their inability to raise more money on their gender.
Companies with female founders get funded all the time. Many companies with female founders also crash and burn not because of sexist actions, but because of bad ideas, bad execution, bad luck, or any of the other factors that can sink a company.
Tessler was concerned about Kay writing her blog post on fundraising while female and going public with their story because she didn’t want it to come across as reading like an excuse, she said on Startup podcast (the episode on fundraising below). After all, they can’t change the fact that they are female, so they couldn’t change anything about the amount they raised.
Kay, though, was realistic about Dating Ring in conversation. It wasn’t perfect. They, like many startups, needed investors to take a leap of faith. And that’s where they saw maybe men have it easier.
“There are so few female investors and there are very few that are doing risky early stage,” Kay said.
The co-founders are speaking publicly about it now because their company is stable and getting by on cash flow with no plans to raise again in the near future. Not all female founders can speak out about what they face though, and it’s a business decision that Tessler knows not everyone can make.
You might alienate potential investors while your company is too fragile to stand on its own, or get backlash from some members of the tech community itself, who continue to debate whether this is a problem at all.
“We’re not exactly a perfect company,” Kay said. “There’s just so many ways to turn the topic around and attack us.”
For that, Tessler said, remember there is a world outside of the Valley: “It feels like you’re going to get slammed, but the rest of the world will be behind you and you’re going to get more support than you think.”