Creating a City Guide from Scratch? Maybe if You’re a ‘Cool Kid’

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You probably are not cool enough for this site, so just move along. Then again, online city guides are not so cool any longer. So … welcome!

Surely I jest. Well, sort of. One can never look askance at optimistic youth unburdened by past realities and unrestricted by future hurdles they can’t possibly yet see.

So these are cool kids: Carlos Gutierrez and and Erika Leal, founding editors of, bootstrapping their way into building a city-guide-cum-entertainment-site for not only big metros but also for smaller, under-served towns (at least that’s the plan).

I asked Gutierrez, founder of the obvious question first: Why? So many have come and gone; others are moving along (Patch, Yelp, Zvents, Foursquare); still others (LivingSocial, etc.) are morphing toward city guides.

Why a city guide?
I feel that, while it’s becoming a crowded market, each city guide I’ve seen and used has had its limitations. Some only offer you things to do in the large cities like L.A. or New York, while others simply pull in information from around the web without without weeding out the bad places. With the Cool Kids Guide we provide users a curated experience where we research, discover, and only include locations and places we feel meet certain requirements. We want to offer users a way to discover places not only in large cities but also small towns and in and around their neighborhood and cities near by.

We make it easy to search for places and things to do while on a date, out with friends, or by yourself. For parents, The Cool Kids Guide lets you easily find places to go and things to do specifically with kids. Unlike some city guides, we plan to feature one-time only events, activities, and shows happening in your neighborhood such as art walks, pop-up shops, flea markets, shows, etc.

Why should consumers care?
The Cool Kids Guide will be a one-stop destination for people to discover what’s going on in their city on a particular weekday or weekend. It will be a way for people to find bars to take friends, or a romantic restaurant to take a date. It will be the place for parents to find places to take their kids, and for men and women to learn about the latest sample sale going on or new pop-up shop going up.

Is this for cool kids only or will my mom find cool things to do?
Despite the name, The Cool Kids Guide is aimed at everyone. We will feature not only places and activities for kids but also for adults such as bars, restaurants, and shops.

Scale… My experience has always been that scaling beyond DMAs into smaller towns is extremely hard. How are you doing it?
Covering smaller cities is definitely a challenge. So far we have had excellent results at covering the smaller cities and towns by working with freelance writers and photographers in and around cities we are covering. To know what to cover in each city, myself and my co-editor have been reaching out to locals in the area, researching locations online, and using other sources to find places that meet our requirements.

What about money? What’s the revenue plan?
It will be only advertising supported for now with plans to monetize further in the future as we get a better idea of what works and what doesn’t.

Are you working with our feeds or events listings providers?
Not at the moment.

So what’s is the rollout plan? How many cities, towns, burroughs are you planning year one?
At launch we plan to have five counties and several cities including Los Angeles County, Orange County, Clark County (Las Vegas), and San Diego county. We plan to slowly expand into three additional markets soon after launch with several more by the end of next year (2013).

How are you deciding which markets?
In addition to covering the big cities like Los Angeles, New York, and San Francisco we are also covering markets that have been, for the most part, ignored by other city guides and travel sites. We are covering places with large populations but a city that doesn’t tend to be a travel destination. Every city has cool places to eat, play, and hang out and we hope to discover every one.

Are you planning to be “mobile first” or a web destination with a mobile extension?
We will be web-first with plans for a stand-alone mobile app to follow soon after launch.

Speaking of which, when will we see a product launch?
We are set to launch in January.

Rick Robinson’s Turf Talk column, which had been on hiatus since December, is now again appearing regularly on Street Fight. Follow him at @wideopensea.