I’ve never spent anytime with the man behind Mahalo.com and Weblogs, Inc (That he sold to AOL.) but I wish I had. I really enjoyed what this web wizard had to say and how he said it. Yesterday at the Spring OMMA Global-Hollywood Conference and EXPO at Hollywood and Highland I ran into Keynote speaker and Internet Entrepreneur Jason Calacanis at a party and got his spin on Internet Advertising.
During Jason’s Keynote he spoke about how Social Media sites like Twitter, Facebook and MySpace are either reluctant to allow advertising on their platforms or they are not advertising in the correct way. Jason talked about how Social Media sites are parties and you can’t just walk into a party and start advertising. People want to party. They don’t want marketing at the party. He went on to give examples of how he thinks Facebook should use disruptive advertising to make people watch a movie trailer ad before they are let into their Facebook account and that Facebook should also offer a PRO version with no ads for those who are willing to pay for an ad free experience. Jason also gave away some business models for Twitter like how Starbucks could be using Twitter for advertising and showing how Twitter could have sponsored slots for companies that want to reach new Twitter sign ups. The way it would work is when a new person creates a Twitter account they would get 20 new friends at sign up and some of those “new friends” would be companies who paid to be there. Jason said he offered Twitter $250,000 for a two year deal to have one of his Twitter accounts: @answers be one of those sponsored accounts but Twitter wouldn’t take his money.
Jason had a really interesting breakdown that compared Super Bowl Advertising to this type of advertising and the take away was thought provoking. With a Super Bowl ad you spend millions and walk away with bragging rights. With a sponsored slot on Twitter you would spend much less and over a two year period you would walk away with a “mailing list” of people you could continue to interact and market to as long as you did it in the correct way.
I go to a lot of conferences and I’ve never hung out with Jason but I would really like to. I found Jason to be very funny, thought provoking and if you watch the above video you’ll see how generous he was in throwing out an idea about a comedy video series where women market products in a silly and sexy way. I think he’s on to something.

