Today I wanted to talk to you about pitching.

Pitching products, services, ideas and more generally how to tell people about things without them explicitly hating you afterward.

The inspiration for this post came, like most posts, from personal experience; this time that experience was my wild and wacky adventure to SXSW a few weeks back, where the fields have grown ripe with every variety of pitch that man kind has had the pleasure of producing. This guide will introduce you to some of the species and hopefully give you an idea of what seeds to sow when planting season comes a’calling.

The Party Pitch

Almost everyone is selling something at a conference, and the best place to find out in excruciating detail what that thing is, is to show up at a party. While most people are much more interested in making their way to the open bar or casual conversation at the open bar, there is a species of Pitcher who takes this time to spend anywhere between 30-40 regaling you about their product.

The problem with this sort of pitch is that it ignores the first rule of pitching, “Understand your Audience.” If you are standing in front of a guy who has had one too many Rum and Cokes and you’re trying to explain complex taxonomies and your freemium business model, you aren’t really getting anywhere. At best, he wakes up the next morning and finds your card stuffed in his pocket and hopes that he didn’t accidentally make fun of your hair plugs. This is a bad way to get your product idea across and a good way to lose a potential opportunity.

The “I’ve Got Stickers” Pitch

They might also have pamphlets, buttons, tee-shirts or any other kind of minor swag. These are the people you find prowling around conference halls looking for any and all opportunities to hand out their promotional junk in exchange for five minutes of your time.

This is not actually a terrible pitch style, if you understand what you are offering. Most people don’t really care about your buttons and stickers, if they stop at all it’s because they are vaguely interested in what you have to say. The only way you can make good on this unspoken deal is if you keep it short, punchy and do your best to follow rule number two of pitching, “Only Tell People What They Need To Know.” Take some time to look at the badge and try to get a feeling for who you are actually talking to and tailor your pitch accordingly.

Girls (and Boys) Just Want To Have Fun Pitch

The best thing I think I witnessed at SXSW was when I saw the Foursquare (a cool little app that lets you tell everyone in the world where you’re hanging out) team actually playing Foursquare outside of the conference hall. They weren’t just doing this to get an opportunity to transfer into an “I’ve Got Stickers” pitch, they were doing it presumably because they like Foursquare.

And it worked.

It drew a crowd, armed with iPhones, dreams and the desire to tell everyone they knew about what they were watching.

This is rule number three of pitching, “Stop Taking Yourself So Seriously.” Have a little more fun with your product. Sure, people want to see your passion, but they are also interested in seeing that you can laugh a little about how ridiculous it is that people actually buy your Beer Goggles iPhone App. Find something you enjoy, that other people can participate in and do it. Fame, fortune and blog posts may indeed follow.

The Weird Stunt Pitch

Stunts are cool, they can even be fun. SXSW is known for them. Take care though that you understand what kind of message your stunt is actually sending to your potential customer base.

One afternoon, I walked into a bathroom in the Austin Conference Center and I saw that the urinals had business cards on them. I was quite pre-occupied at the moment, so I didn’t bother to investigate but when I left I couldn’t help but wondering what this clever entrepreneur was hoping to accomplish. Sure, he would most certainly get a few people to stare at his website for longer than they might otherwise have but they would forever associate him with hastily relieving themselves. I’m no brand manager but I doubt this is what he was going for. That leads me to my next rule of pitching, “Understand What Message You Are Actually Conveying.”

The “Hey You Look Like Press!” Pitch

This particular brand of Pitch only happens if you are wearing a press pass, a camera or a recognizable face and it can be one of the most frustrating of the bunch. Yes I know as an entrepreneur you are always looking for chances to get mentioned in the press, but that doesn’t mean you need to circle reporters like a Twilight Vampire at a Junior Prom. First you need to know what the media person is actually there to report on, if it turns out he is there to write a scathing piece on bad Pitches you may want to back off a little. If, however, she is looking for startups to interview about the state of venture financing, you still might want to pause for a moment so you don’t spend 30 minutes talking about your most recent Social Media Campaign. The rule here is that before you start pitching you should always, “Pause And Reflect,” on what you are trying to say.

This is one of those Pitch styles that comes in a variety of sub-species, including the even more frustrating, “Hey You Like Like An Internet Celebrity!” version.

The Over-Pitch

For the last pitch I wanted to pick something that was not technically a pitching style. All of these other types of pitch can be appropriate given the right context and the right message. This, however, never is. Unfortunately, entrepreneurs who are new to interacting with human beings or just overly excited about the thing that they’ve put their sweat and blood into often shoot themselves in the foot by using this style of pitch once to often.

You must know when to stop pitching.

You need to get a sense for when people are saturated with information about your idea and are no longer listening. This needs to become second nature to you and you need to trust this sense explicitly. There is nothing in the world that ruins opportunities faster than spending an hour and a half waxing poetic about your startup when people are trying to raid the free food. If you find that your victim is nodding silently and looks increasingly glassy eyed and distracted, it’s time to start wrapping things up. It’s easy for a great idea to transform into an annoying experience when the Pitcher tries too hard to close the deal.

Remember, not everyone has a million dollars in their pocket and even those that do don’t often give it out on the first date. If your idea is good, relevant and useful to the person who you are pitching all you should do is make certain to exchange cards and send them a follow up email a few days after the event. All over-pitching is going to do is give them a funny story to tell later that night at the open bar.

There is no such thing as a perfect pitch. Different people respond to different things in different situations. However, there are good and bad pitches and the distinction between the two mostly involves how willing you are to recognize and respect people’s time, attention and intelligence. Remember, no one has to listen to your ideas and when they do you should be certain that they are rewarded for it.

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