Dating ring ceo So Dating Ring launched in Her cofounder Emma Tessler on the other hand was new to entrepreneurship but loved matchmaking. Nailing their pitch on stage in front of a roomful of investors. Emma was watching from the side as Lauren delivered that pitch. There is going to be a billion dollar company that provides on demand dates. And Dating Ring is going to be that company. And Lauren killed it. Hearing the pitch was like looking up from all my work and like seeing this like beautiful thing that we'd built. After the pitch, Emma and Lauren and their third co-founder Katie filed out of the auditorium to have a drink and mingle with investors.

And this is a big moment.

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

They had spent months preparing their pitch and now they were in this room schmoozing with some of the most powerful investors in Silicon Valley. It was a unique opportunity for a new start up like Dating Ring to come away with a lot of money. Emma ran into an investor she had met earlier in the day and they started talking.

Somehow it came out that he was New York-based and he was like oh when we got back to New York we have to go out for drinks.

But he's an investor and maybe people have investor meetings at bars over drinks and I'm sure if I was a man I would be like. Of course yeah we got to get drinks. So I was like yes totally like we should meet up for drinks. And he put his arm around me and and his arm landed on my boob. On my side boob. And it stayed there. He just sat there kind of like holding me and while he was holding me he's like you know what I'm going to invest in you girls 50K. I'll give you 50K to start and we will have a great relationship.

And like this is going to be awesome. And like you and I can keep meeting up in New York since we're both in New York and we're like this will be great. And the whole time he's standing there with his hand there. I knew that I was definitely really uncomfortable. I was doing what I think a lot of women do which is convincing myself that it wasn't a big deal.

I was like oh it was my side boob that's only side inappropriate. And I was like I don't know maybe it's not a big deal. Like maybe that's like a part of the body people touch accidentally a lot. Emma didn't exactly know what to think but she knew she wanted to get away. She found her two co-founders who were standing in another part of the room. I went up to Lauren and Katie and I was like oh my God you'll never believe what happened. And it's interesting hearing because I told it to them and they were sending me to guy friends But I don't know it's not that big of a deal.

But it was amazing how long it took us to decide. I mean days we struggled with should we take his money should we not. This wasn't just 50,, right? This was their first 50, So on the one hand having money minutes off the YC stage would send a powerful message to other investors that you better get in on this opportunity fast. But on the other hand: And eventually we figured.

The Dating Ring Crowdtilt Campaign: Help Us Fund Cross Country Love

It's not worth it. So, we didn't take it. And in many ways things just got more complicated after that. There weren't any more handsy investors. But asking people for money can make you feel bad about yourself in so many different ways and it can raise questions you never thought you ask yourself.

Her first meeting was with an investor named Ben Boyer. And after a few minutes of casual conversation he got right to the point. But I love to write a check. And it was the best feeling ever. I mean it's so high and it's so addicting to be handed that kind of money and validated by someone who knows what they're doing.

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An early investor in Uber threw in 50 grand. A few more angels came in as well. At this point Dating Ring was following the script perfectly. Conventional wisdom is that YC is a big stamp of approval. Investors behave with something of a herd mentality and so coming out of Y Combinator that can act in your favor. You get momentum and you can raise all the money you need And so if you can just ride that wave, like, you can ride it to a million or more.

But a week after demo day even if you're not on that wave anymore, you're just crashing and crashing and crashing and then you're done. There is a moment when you're not sure if you're still on the wave or not. But pretty quickly Lauren realized she had slid off the back. In just a few weeks, everything was different. Her investor meetings changed dramatically.

Matchmaking as a service

Umm from I guess an angel smaller investment standpoint. There were a lot of people who who were criticizing me for not having done more. And then there's this one. And eventually we figured. I feel really stupid about it.

Nice to meet you. This is Emma and Lauren meeting an investor named Somak Chattopadhyay. And he's pretty emblematic of a classic off-the-wave pitch meeting. They start the same way as when you're on the wave. Friendly chit chat and small talk. But then after 15 minutes, instead of the classic on-the-wave move of taking out a checkbook Somak started asking some tough questions.

I mean, what is like Umm, that is something that we should be looking at. That is just one thing that Somak wanted to know. He also asked about their technology; their future hires; how they plan to acquire users. And these kinds of questions started happening all the time with lots of investors. When you're working out what's your average cost per match? What are you burning right now? Have you launched any type of user acquisition campaigns through Facebook? Can you explain what part of the matchmaking process is technology enabled? You know, is it scalable when you have matchmakers?

How many part-time matchmakers do you have? I mean do you see this as a business where there would be an exit? And these off-the-wave meetings, they ended all the time in rejections. Let me think about it. It's not quite set up to be a mass kind of volume business. I think the valuation cap is high.

Umm from I guess an angel smaller investment standpoint. So let me look at the deck. You could send it to me.

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I should probably be on probably the C list. Lauren keeps a spreadsheet with the names of all the investors who said no. So how many people are in this spreadsheet? These are only people of like rejected me to my face. Giant waste of time, kept saying he'd invest and never did.

Dating Ring

And then there's this one. I heard all the time when I was pitching my own company, Gimlet Media, the producer of this podcast. You can hear all about it in Season 1 of Startup. And the A pass is when an investor says I'm not investing now but come back and talk to me when you're doing your Series A. Series A is what they call the next round of fundraising after you raise your first initial seed round. A lot of companies don't even get to a Series A, they fail before that.

And so Lauren had the same feeling I did when I first heard that line. And he just like he is he's just we're just a little too early for him. You just got the A pass. And one of the more frustrating things to Lauren about all this rejection was that it felt sort of self-fulfilling.

A lot of the stuff investors claimed to want to see was stuff that Lauren could only build if she had money. Take for example this exchange between Emma and Lauren and the investor Somak Chattopadhyay.

How to listen:

Who's overseeing marketing user acquisition analytics? Do you all own a piece of that or is there someone dedicated to that function? Somak is asking about marketing. Who's going to be doing it for Dating Ring. And Lauren explains that there's a person she's planning to bring on board, a friend of hers from college. And this leads to a somewhat revealing misunderstanding. She's looking at your data like your usage data and doing analytics, like doing statistical analysis stuff like that or Yea, she probably will be.

I mean she could probably do anything. Right now what is she going to be doing? This director of marketing—Dating Ring was not able to bring her on board because they didn't have enough money. Some matchmakers and a marketing person to help them acquire new users. And they had raised less than half that. Before they slid off the wave. And what made all this worse was that the shift was so sudden and seemingly so arbitrary.

In those first couple of days of fundraising investors had barely asked any questions at all. They just wrote the checks. But then after everything flipped there were no checks just lots of hard questions and often Lauren couldn't even get to a meeting. She got rejected before the meeting even happened, over email. For Lauren it was hard not to wonder why. You're in high school.

And everyone's talking about you behind your back because all the investors talk and you don't know why anyone is saying no. And you don't know what they think of you. And why they don't like you. And you just start thinking all of the worst things about why it might be. I must be doing this wrong, I'm not confident enough or I'm not good at pitching my company. 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. 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.

Not surprisingly, the trip got a lot of press —not all of it positive. While much of the coverage was biting, Kay says she still sees the Cross-Country Love trip as a success. Fortune plans to follow up with Kay and Tessler once the season is underway.