Street by street, block by block

Back in the early days of grad school, when questions about the future of online advertising came up, I was bullish about the future of location-based mobile advertising that would by contextually relevant to the content you were viewing and the place you were sitting.

I was wrong about a big piece of how this would work: I envisioned free wireless access blanketing the world, so that you could be sitting on a bench in downtown Santa Cruz with your laptop and find out, while reading a story in the Santa Cruz Sentinel’s food section, that Lulu Carpenter’s had a deal on day-old pastries right now.

This was pre-iPhone, and the most “super” mobile device I had at hand was a bottom of the line half-sausage sized thing from Verizon.

Now, that next step for local advertisers looking to capture walk-in business from real live human beings in their neighborhood is becoming far more clear.

Foursquare and Gowalla, location-based services you should be well aware of by now, are already getting into this business, opening up the market.

Here’s the “anatomy of a Foursquare special” as broken down by Cory Bergman at Lost Remote:

“Clicking over to the special reveals a useful offer for a free drink with a $20 purchase — if you show that you’ve checked in from the restaurant.”

Keep in mind, a note about a “nearby special” shows up in Foursquare next to the name of the business when you’re casually browsing nearby places, or checking in at the competition across the street.

Over at VentureBeat, a look at iPromote, a company building a mobile ad network to allow local businesses to advertise to anyone who happens to walk by:

“For a minimum of $5 per day, iPromote will serve ads to mobile phones near an advertiser’s place of business. The company serves both display ads, for which clicks aren’t counted, and cost-per-click ads where the advertiser only pays when a user clicks through an ad to their site.”

Sounds like a healthy model.

Of course, there’s a disruptive elephant-sized gorilla in the room named Google.

Push a button on your phone and Google tells you what’s nearby. As in, local businesses, restaurants, etc. How long before they start selling featured listings based on geography? Want to be the featured one-dollar-sign, four-star restaurant within a fixed square mile? That’ll cost ya…

Here’s the short list of location-based mobile apps on my iPhone right now:

• Foursquare – Mostly using this these days when I’m at a restaurant or otherwise non-routine location. Especially useful when I was in New York City over New Year’s.
• Gowalla – Trying it out. It’s cuter than Foursquare, but I don’t see how it’s any more or less useful yet.
• Yelp – I still use Yelp on my phone whenever I’m in a strange city and just want to know where the nearest Thai, Vegetarian, or Burrito  joint can be found.
• UrbanSpoon – Cute slot machine interface, but nothing special.
• Brightkite – I used to check in here socially, as I way to declare when I arrived in a new town for a conference. More for social check-ins than local business action, and I haven’t checked it in months.
• EveryBlock – Might be fun to check the restaurant inspections, Flickr photos, or crime reports here while walking down a block, but I haven’t.
• Honorable mentions on my phone for Redfin and Zillow — both real estate apps extremely useful when househunting, especially when you just want to know what’s for sale near your current location, while you’re cruising around checking out neighborhoods.

Have any favorite location apps that I’m missing? Are any local news organizations selling their own location-based mobile ads, or just buying into larger networks?