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And then you start thinking "no one's ever going to like us or give us money. All this rejection— I know from personal experience—it can send you into this downward spiral. Pitching after all is all about confidence. And the more I would doubt myself or my idea or my pitching skills, the less confident I would appear and the more desperate. Investors like people everywhere can smell desperation. But amidst all those anxieties that all startup founders feel, Lauren had a question that was more specific to her. A thought she had dismissed up until then.

And once that question gets in your head it's very hard to ignore. Coming up we ponder that question and discover how risky just pondering that question can feel. And I'm Lisa Chow. And let's start the second half of this show with this. I have struggled with writing this blog post for months. Unless I have an absolutely perfect indefensible business—which I do not—I'm easily written off as someone blaming my failures on my gender.

This is Lauren reading a blog post she wrote after weeks of unsuccessful fundraising. One investor took me to lunch said he wasn't interested in investing and wanted to test the product out by going on a date with me. Another investor introduced me to a group of fellow investors as the beautiful CEO who has two other beautiful co-founders. Another investor met with my CTO, held off on investing, and then asked one of our matchmakers if he could be set up with our CTO or someone like her. For months Lauren had been struggling with this question—Am I failing to raise money because I'm a woman?

It was called Secret and it had essentially become a Silicon Valley gossip site. People posted anonymously on all sorts of things. How much money companies were making; who had hooked up with whom. And there were a lot of threads about fundraising specifically women and fundraising. And there were comments. Women are baby machines.

That one had likes. And then there's this one, which to read I have to use the F-word. Lauren told me she struggled with how to write the post in part because blatant sexism wasn't the worst of it. A lot of the sexism was harder to pin down. There was this idea called pattern matching—it comes from computer science.


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But the way people use it in this context, is this way: When investors look at successful founders they see a pattern. Most of them are men of a certain type, from a certain background.


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Do you look and sound like Mark Zuckerberg? And you're an investor, you don't have to invest, it's not a charity. And there is data that something like this is going on.

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In one study for example men and women delivered the identical pitch to a group of investors. The men were 40 percent more likely to receive funding. Another study showed that 85 percent of venture-backed companies do not have a single woman on the executive team. And less than three percent of venture backed companies have a woman CEO.

Some felt like Lauren. We should try and point it out. Call attention to it share experiences. In fact, one of the women I talked to in this camp, the opposite of Lauren camp, was Lauren's co-founder, Emma. She remembers Lauren's blog post.

Dating Ring Careers, Funding, and Management Team | AngelList

Yeah, I remember reading it and I was concerned about it -- it reading like an excuse. Even though a lot of these instances are like clearly sexist. And even though they're true. I don't think the reason we didn't raise is because we're women. And if it is because we're women, there is nothing we can do about it so it's not a helpful critique. And so I want to focus on that.


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But even Emma wasn't immune to the complicated emotional responses to being a woman in Silicon Valley. For example, a site called Gutsy Broads had put out a call for essays from women about a time that they did something gutsy. Lauren went to Emma and said you know we turned down that money from that guy the handsy investor— that was gutsy—why don't you write about that?

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Emma hesitated at first, but eventually she did. She read a section to the other Lisa It was a big decision to make and I couldn't stop questioning whether I was exaggerating what happened or being too sensitive. My co-founders immediately assured me that wasn't the case and though we could not take the money. They said it was ridiculously inappropriate that our relationship with him would only get worse and that we should hold out for better investors to partner with.

And so the next day I sat down and wrote the investor an email. I told him that while we appreciated the offer, we were being very strategic about which investors to partner with. It felt pretty gutsy at the time, but since time has passed I couldn't be more confident about the decision. Why did you just laugh? Well, because I am not so confident about the decision. I feel really stupid about it.

I feel really -- really embarrassed for not taking the money, like maybe I made too big a deal of it and maybe it wasn't an issue or maybe like this is just how the world works then I'm like being a baby about it. And I feel that. But but intellectually I know like if you told me that that happened to you I would be like, "What the fuck. Like we have to tell everyone he's a creep like, you did the right thing. What would happen next. What would the reaction be. You know they were mostly they were mostly really good.

There were a lot of people who who were criticizing me for not having done more. They said you have to name him. This isn't this is cowardly. You have to name him you have to protect other women from him. Why didn't you tell him why you didn't take the money. That's a really easy mistake to make. I'm sure I hug people and accidentally leave my hand somewhere and like I'm sure he didn't know and like that's ridiculous and He didn't really do anything wrong.

Although to be fair there were much fewer of those. Like fuck you if you ever touched a breast because you know when you're touching one. Did you feel glad you've spoken out? That made me feel like I did the right thing. Meanwhile Lauren, the one who pushed Emma to write about her feelings, never published her own post—the one she'd read earlier about whether sexism affected their fundraising.

Over the months that she'd been thinking about that post her attitude had started shifting and then she had this epiphany at an event for women in tech called the Female Founders Conference which was put on by Y Combinator. Wow, this is awesome. There are so many women in the audience and I am so happy to be here with you. This is Danielle Morill, the co-founder of Mattermark, a company that provides information about startups for investors. And she was one of a bunch of women founders and executives at this conference offering tips and support and encouragement for the audience.

Show Notes

And if you don't get an offer. Just keep assuming you're going to get an offer. Like, kind of stay a little bit entitled.

I mean we got nos way more then we got yeses. We just kept thinking—yep, well the next one could be a yes. Not all that was encouraging to Lauren. Some of their experiences were quite different from hers. I kind of love fundraising. We have raised one point seventy five million dollars to date. But mostly it was women on stage sharing stories of their struggles; their setbacks; sharing tips and hacks for how to sequence investor meetings; how to prepare for a pitch. And then there was one piece of advice that really stuck out for Lauren. It was sort of pivotal for her, actually.

Just to make sure that I say this. I think it's probably the most important thing I've learned about fundraising. Like all these other strategies and like hacks to X or Y or secondary entirely to just really fundamentally believing in what you were doing. Like knowing that it is good. You have to know that what you were doing is good in that it needs to exist in the world.

Because if you know that, then you are already setting yourself apart, because very few people actually know that what they're doing is great. I don't have a great product and you probably do. And then I was like sitting there googling Clara Labs and I was like so cool. But I was like you're right about that confidence. But I couldn't fake that. I didn't have a great product that everyone was raving about. And I was like fuck, you know that that also was a big part a big hurdle for us with fundraising. Our product wasn't at the stage that we really believed in it.

They still weren't growing.

Dating Ring 3: Another Side Of The Story (REBROADCAST)

They were burning through money. Lauren knew all that. But hearing Maran talk, it brought it all into clearer focus. And it made her realize something: The deck is stacked against women. But it's also true: So that was what Lauren decided to focus on. Making her company great. Thanks for listening to this rebroadcast from Season 2 of StartUp. To hear the rest of the episodes about Dating Ring, go to our feed in Apple Podcasts or check out the show at the Gimlet Media website, Gimlet Media dot com slash startup.

And so will her co-founder, Lauren. Mark Phillips wrote and performed our theme song. Build Buildings wrote and performed our special ad music. John DeLore mixed the episode. Season Two of startup featured original music written and performed by John DeLore and his band Hot moms dot gov. See you next week. January 16, New. January 15, New. Sarah Koenig is the host and co-creator of Serial, the show that made podcasts a cultural phenomenon. After three seasons of exhaustive reporting, January 14, New. ELT finds out where millions of pounds of pocketknives, sunscreen and snow globes end up.

Show Notes The Story. The Facts Our theme song was written and performed by. December 28, Success Academy 7: The High School by StartUp. December 21, Success Academy 6: The Fights by StartUp. The tape caught dozens of fraught exchanges between Blumberg and his wife, his partner, his investors and several of his overworked employees.

Kay and Tessler say they expect Dating Ring to get the same warts-and-all treatment. They are continuing to tape through June and will not hear any of the episodes before they air. What else will we hear this season? A partner leaves the company unexpectedly, say Kay and Tessler. They say the Startup staff has interviewed a number of people, including Y Combinator partners and the head of competitor Match.

Last year, Kay noticed a striking imbalance in the Dating Ring membership: In New York City, they had far more female clients, while their San Francisco database was dominated by men. So, the company cooked up a stunt: Cross-Country Love, a crowdfunded event where the company flew 16 single female New Yorkers out to the west coast for a long weekend of dates with Silicon Valley bachelors.



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