What being hopelessly single taught me about pitching tech celebs

Thanks for the comment, Paul. Blog posts are funny, b/c you have to boil down a bunch of complex ideas into something people can grok while skimming. I actually don't like the word "pitch" or think of myself as someone who really pitches things very well at all. But it does describe sharing your ideas with other people, capturing it in a single word. A more accurate description would be "sharing your vision" or something similar.

If there's one thing I've learned over the years (whether meeting new startup people or trying to get a date) it's been the "don't be a douchebag" rule. Treat people like people. The best "pitch" is actually not a pitch. It's authentic, where you're talking to someone who you honestly believe will be interested in what you're doing, and you're sharing something you're sincerely excited about.

The last person you want to be is one of the "Jersey shore meatheads" trying to dry hump some poor woman out on the dance floor (to harken back to my earlier analogy). :)

Coming from the point of view of somebody who gets pitched daily...

I can barely distinguish them from each other.

Sure, I'll give you my card with contact info, but it doesn't mean I will be interested when I get the email.

Yes, you did more than most people and had the balls to approach me. Great. But that won't fix a mediocre product or a product I'm not interested in. I'll just end up ignoring your email.

I look for cues, such as who is funding you, your background and whether you got an introduction from somebody I trust. These things are my filters to finding the stories and startups that matter.

Beyond that, I agree with PG: I prefer ordinary conversations. Again, the people I know and find genuinely interesting are more likely to catch my attention when the time comes to pitch me.

It is actually how most of the world works: you tend to remember people you meet in person (versus those who cold email or call you), and as long as the pitch is not canned or scripted (people who do this well can be very conversational about how they describe it), it can lead to a follow-up meeting and further discussion.

My title is literally Chief Handshaker at FreshBooks. I wheel and deal for a living.

When walking up to people randomly, I find it is immensely helpful to be genuinely interested in people. They will often pay you back the favour by being genuinely interested in you afterwards.

To be honest, I do what I do because I love people. They are endlessly interesting. I don't do it to build my Twitter follower count.

If you walk up pitching they will just turtle and get rid of you. Have faith they will ask you about you in due course.

From the comments here, I infer, VCs probably don't like being pitched unsolicited. Girls don't like being hit on. I have never pitched a VC, so i am basically theorizing here. The trick is not in approaching them, but approaching them in a way which does not activate their natural defense mechanism. If you come across as interesting the girls will give you attention. Its better to lower their defenses with an approach that they don't expect.