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.
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. 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. 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 labeling someone. Ellen Pao was the most recent high-profile case of gender discrimination in Silicon Valley. She lost her trial on March 27, People she confided in had the same "that's messed-up" reaction, but she faced doubt and fears of over-reacting, she said. Oh Jesus it's still there. He must not realize how far he's wrapped his arm around. What an awkward mistake to make," she remembered thinking at the time of the incident.
I think it's what a lot of women experience with a myriad of events," Tessler said about her thoughts in the moment. Maybe I'm being overly sensitive. The three 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 wouldn't be in this position of denying my company money that would really help us. The result was only so-so. 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. I'm talking about a problem without a solution," Kay said to Business Insider. This shouldn't be something we still debate whether or not it exists.
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. They, like many startups, needed investors to take a leap of faith. And that's where they saw maybe men have it easier. 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.