Why raising capital is exactly like dating

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I had the pure privilege of spending the late afternoon and evening with a dear friend and colleague, Fred Becker, board member of  GGM Capital. We went to a number of events in the Tel Aviv DLD conference, and I had the unique experience of  seeing through the venture capitalist’s eyes.

A while ago, I wrote a post on why a job interview is not like a first date, but from the perspective of a single lady, pitching your startup looked a lot like dating. Here’s how.

You know it when you see it.

People with funds know what they are looking for, just like you know what you are looking for in a partner. When an investor says it doesn’t matter what industry he invests in, that’s equivalent to saying you don’t care what height or color your date is. You still have a very long list of things you want and an even longer list of all the things you won’t tolerate in a partner.

The list of what you want isn’t necessarily what you’ll end up with, and it isn’t necessarily comprehensive. Most of the attributes aren’t even fully articulated. But you know it when you see it.

An introduction is just an introduction.

I was in the mode of thinking about dating, because earlier this week I had asked a friend to let another friend know that I was interested him. There was a high likelihood I would run into the target guy at one of the events this evening.

At the same time, I know that dropping that hint means only one thing. It means that if that guy either didn’t know I was single or was too shy to ask me out, he now had an opening. If the guy had noticed me in the past and was not interested, it would make absolutely no difference.

When I made introductions between Fred and startups, all I was doing was bringing potential to his attention.

I made an effort to read Fred’s level of interest during the conversation so I could improve the introductions over time. I did a fairly poor job it, because he is a real pro. He was supremely gracious and professional with everyone, asked relevant questions, looked them in the eye, and stood so that nobody could interrupt the conversation (very annoying to me when I was trying to get him to move on to the next introduction. When I work a room, I work a room. I suspect he was more intent on making sure that he wasn’t missing something so he knows for sure whether it’s worth the meeting.)

Despite his poise in every situation, when he was really interested I knew. You know how I knew? He said the words “this is something we would be interested in” or something of that kind. He said those words in fewer than 10 percent of the cases.

No, really. You know it when you see it.

One of the entrepreneurs was really a good salesperson. Sharp, responsive, human, polite, properly dressed, and just the right level of pushy and just the right level of fun and friendly. If I didn’t know this person beforehand, I would have fallen in love on the spot.

But I knew it wasn’t something Fred was interested in, because he didn’t’ say those special words. Oh, and he talked with me about the startup afterwards. Just like in dating. As soon as you leave the pub with your buddy, you rehash and rate everyone who came on to you, and let one another know which ones you think are worth an hour of your time later on.

Within minutes, the investor knows if they want to take it to the next stage. It really doesn’t matter how amazing your pitch is after that. I’m telling you, if I were looking to hire, I would have hired this entrepreneur immediately. Probably my friend would have too.

But it didn’t matter. Because there were some attributes that didn’t match. Just like in dating. You just know.

If the other side isn’t interested, move on. No charm, convincing or manipulation will change the fact that you don’t fit into this person’s list of criteria.  Remember that list of attributes you don’t want? It’s longer than the ones you do want.

You still have to look hot.

I was wearing a red dress. I was wearing a red dress because I thought there was a good chance that I might run into the aforementioned guy. It can’t hurt. I mean, if he was considering the opportunity and ran into me, and I was dressed like one of the guys and shook his hand (which frequently happens during office hours)… well let’s just say it’s not the same as the red dress/ big hug combo.

I was also wearing a red dress because it is always a great feeling to be the person whose friends look fab. If I’m going out to a party with a friend I love, I am going to look my fabbest so my friend looks like he has fab friends. I mean, I’m still a geek and a weightlifter, so there’s only just so fab I can look, but I did my best.

Even if your startup is the right match for the financer, you still have to look the part and go through the motions. It’s part of being a professional. If you don’t dress and behave appropriately, everything else can be perfect, but the courting won’t go on for long.

I kid you not; I was once talking to a founder who told me that he didn’t think it was necessary for him to practice his presentation, because it is, in fact, the VC’s job to understand what he does and select his startup based on merit. Dude, that’s a great philosophy.

The truth is that showing up for a meeting without practicing your presentation is like saying “I don’t care about presentation, and I don’t care enough about your time to come prepared.” If you don’t dress and act like a professional, you aren’t one. I don’t care how brilliant the idea is, how great the technology, or how big the market. If you can’t care enough about how you look to an investor, you won’t care about a customer either, and you won’t sell.

You can get away with it once in a while, but if you consistently show you don’t care, there’s no relationship. Not a business relationship, not a personal relationship.

A coffee is just a coffee.

Each stage of a relationship is just that. A stage of a relationship. If you have a first meeting, it means that the other person was willing to spend an hour or two with you. It doesn’t mean they are sure there will be a long-term relationship. It just means that for them, that time isn’t a waste of time.

For a date, it could mean just checking someone out or not having anything better to do on a Saturday night. I guess a lot of gyms are closed on Saturday night.

In an investor relationship, it really could mean anything, from we are interested to we are interested in the competition, to we are just kind of learning about new technology. It’s just a meeting. But it’s your time. Make the most of it.

Well, it’s not really like dating.

If you’re an investor, the only way in which the investment process is like dating is how I imagine dating would be for Natalie Portman. Unfortunately, most of us aren’t Harvard graduates who are also gorgeous, rich and fluent in 6 languages.

So you can imagine why some investors are not gracious and friendly at all times. I feel blessed that I get to spend my time with people who are.

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Rebecca Rachmany



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