The street pitch and the Web ad
The pitch of a street con can teach us plenty about advertising on the Web.
The street con
While walking to the train tonight, a woman approaches me and starts to tell me a story. She is pitching me. She’s trying to get money out of me.
This is very common in Chicago, and I assume elsewhere. Many of these folks are professionals. Perhaps a few are amateurs, but many have honed their pitches to perfection. They’ve had thousand of saps to experiments on, hundreds of days.
She has 50 feet to make her pitch. 15 seconds. 15 seconds between me and the entrance to the train. 15 seconds to make a connection. Time is precious—pitch carefully!
And you. You’re a Web advertiser or publisher of Web ads. You’re a pitcher, too. You don’t have 15 seconds to make an impression—you’ve got about 0.5 seconds. You’d better be good, or you won’t earn a dime.
Let’s learn from this woman, shall we?
The pitch
As follows:
- She greets me. She pitches without waiting for a greeting back.
- She shows me her product. Postcards. She has about 30 postcards with “Chicago” emblazoned across the front and a picture of the skyline or something. (It’s hard to make out, and I don’t really bother to look.)
- She asks me if I’m from Chicago. I respond that I am.
- She asks me if I know of a particular location in Chicago. I respond that I do, although I’m lying.
- She says that there is a homeless shelter there (implying that she is homeless).
- She says that the shelter, or an organization there (I don’t know which) has given her 72 hours to…
Her time is up. The 15 seconds are over. I give her the usual—”I’m sorry, I can’t help you. I’m sorry.”—and get on the train.
Principles of the pitch
The pitch failed. I did not give the woman money. However, they are some good lessons to learn here. The woman conveyed a lot of information in a short time, a lesson that transfers beautifully to advertising on the Web. Specifically, she attempted to:
- Make a connection
- Show the product
- Establish familiarity
- Establish credibility
- Convey a sense of immediacy to the offer
These are all vital things for the 50 foot, 15 second offer. But she couldn’t accomplish them all, and in the end, she got nothing. What could she have concentrated on?
I think she should have concentrated on establishing credibility. When a person approaches you on the street, you have no idea who they are. Similarly, when you view an ad on the Web, particularly for a brand you’ve never heard of, you have no reason to trust them. Goal #1: Establish trust.
In tangible terms, I see that as having ads that are:
- Relevant
- Placed on trustworthy sites
- Clearly marked in conventional ways as links and text
- Don’t interrupt the user experience too much
- Blend into the rest of the page so as to feel like part of the trustworthy site
The pitch’s failure
Notably, the women failed to:
- Establish credibility (I didn’t believe her.)
- Actually present an offer (she gave no price for her postcards)
The pitch as a blog ad
Here’s how I envision her pitch as a blog ad:

It’s okay, not great. Two things it could do better:
- Establish credibility
- Convey why this ad and not another. What’s special? Why now? Why here?
Here’s a shot at improving this “ad” by addressing the two points of failure above.

Conclusion
I didn’t give the woman money. If it had been a perfect pitch, I probably wouldn’t have given her my money—that’s just my policy with random people who approach me on the street. (Similarly, I never click on ads. Call me a hypocrite for running them.) But these people are professionals. Might as well learn from them.
April 19th, 2006 at 8:08 am
Very good thoughts here. Great post.