The Making of MainStreet.com

While the Writer’s Guild of America strike dealt a blow to the television medium this past winter, most agreed the Web benefited (though they didn’t agree how much) from an influx of actors, directors and others who avoided TV out of solidarity.

One digital property that found itself on the receiving end of all that idle talent was MainStreet.com, the new pop culture-inspired personal finance site from TheStreet.com. Were it not for that gloomy winter of writers’ discontent, the somewhat goofy destination might never have attracted the likes of late night talk icon Joe Franklin, The Wire’s John Doman, or the slew of comedy TV writers who gathered to create its promotional video project.

The broadcast refugees created a series of quick-bite videos focused on topics such as tax audits, bankruptcy, and inheritance to promote the site. These clips feel more like branding interludes commonly seen on channels like Viacom’s MTV, VH1 or The N than they do standard online video fare.

But MainStreet is distinguished by more than its high-quality video promos. The overall approach is fresh, from brand concept to SEO-driven content development.

A Bid to Capture New Advertisers and Search Traffic
Launched in February, the site was partly designed as a venue for advertisers that aren’t quite right for TheStreet.com, its more staid counterpart. TheStreet is Wall Street — all stock quotes and market data all the time. But MainStreet is, well, what the name suggests. It does deal with money, but in a roundabout way. First comes the gossip hook: Heath Ledger’s supposed love child, in one instance. Then comes the reel-in: “The fact that the late actor left a will, as opposed to a trust, exposes his assets to more potential claims, experts say.” Practical information on establishing a will and trust follows.

So while TheStreet.com attracts advertisers like EverBank, a foreign currency institution, luxury auto brands such as Porsche, and brokerage Charles Schwab, MainStreet is home to ads for Toyota Corolla and Charles Schwab’s “Talk to Chuck” long-term investment pitch. Ad products available on the site include standard display units, pre-roll video and exclusive sponsorships of specific topic areas.

“The perception of TheStreet was that we reached an affluent self-directed investment audience,” said Tom O’Reagan, SVP advertising sales for TheStreet.com. “MainStreet is getting the TheStreet.com brand and properties in front of an audience that is less sophisticated.” (TheStreet also publishes stock ideas site StockPickr and bank rate comparison site BankingMyWay.)

“We absolutely thought that with a new audience we’d have new ad opportunities,” he added.

Today’s MainStreet content is centered mostly on celebrity tidbits, but the goal is to branch out to other timely content categories. “We’ll try to tie in the aspect of money with everything and anything in the news,” said O’Reagan, adding the celebrity angle acts “as kind of a hook to bring them in.”

MainStreet hopes the strategy will help it capture search traffic. The names of movie and TV stars are ready-made search engine optimizers for the site’s stories because they’re always among the top queried terms. “We were thinking about ways we could get after a different audience leveraging an SEO strategy based on the news of the day,” O’Reagan said.

Joe Franklin’s Racecar Bed
“We want to take a kind of entertaining spin on real world challenges,” said O’Reagan. The promotional shorts do so by visualizing or even personifying financial concepts. Take “Fraud,” a video that’s set to go live on MainStreet soon. In the clip, a disheveled dude in a ratty housecoat, à la Jeff Bridges in “The Big Lebowski,” stumbles into his kitchen, and plucks a cold slice of pizza from the fridge. The doorbell rings. Annoyed, he shuffles over to it.

His visitor? In essence, it is Fraud. Late night TV legend Joe Franklin, a much older man, stands at the door, asks his name, and whether he may have dated a nice young lady in the recent past. Satisfied, Franklin’s character declares, “I am your son. Daddy, Daddy, Daddy. I’m your son, Daddy… All I want is a nice racecar bed, and we must discuss my back allowance. That’s very, very important.” Later, a big band tune blares from inside “Joe’s Room.” The unwitting new father bangs on the door, which is adorned with kids’ room-style cutout photos of old timers like Friars Club regular Don Rickles and musical entertainer Carol Channing.

Videos like this one help users quickly grasp MainStreet’s sensibility, and they’re helping O’Reagan position the site to agencies and advertisers. “I think the videos are a nice way to describe and really show how MainStreet is going to be different from TheStreet,” he said. The promos can be seen in the site’s video section, along other clips featuring things like man-on-the-street reactions to New York Governor Elliot Spitzer’s involvement with a prostitution ring, and Bear Sterns corporate paraphernalia for sale on eBay. They’ve also been distributed on sites like YouTube and AOL, which has a distribution deal with TheStreet.com.

Writers Strike Sends Bored Comedians to MainStreet
It’s no coincidence the TV-quality videos resemble fun vignettes on shows like VH1’s “Best Week Ever,” Comedy Central’s Daily Show or station IDs used to brand channels like MTV, or its teen channel The N. “A lot of us came out of the MTV and VH1 World; we all had that same sensibility,” said MainStreet Managing Editor Caroline Waxler, regarding the team who created the promo clips. Waxler worked as a writer for Best Week Ever, a weekly celebrity gossip recap show featuring countless standup comics, and also wrote a book on investing in vice-based stocks like alcohol, tobacco, firearms and coffee companies. Waxler oversaw production on the videos.

“I went back to the people I trusted and liked,” said Waxler. “I think we couldn’t have gotten all these people together if the strike hadn’t been on.” Early this year, when the strike was in full force, many TV comedy writers, actors and producers were pent up with ideas and looking for ways to pass the time. Waxler’s video project gave them something to do. Some of the people involved in the project are in the Writers Guild, while some aren’t, according to Waxler.

A slew of comedy writers and stand-ups, some from shows such as NBC’s “Late Night with Conan O’Brien,” “The Daily Show” and CBS’s “Late Night with David Letterman,” including Eric Drysdale, Seth Herzog, Meredith Scardino, and Dave Hill (the housecoat guy from “Fraud”), came together to write and star in the mini flicks. Head Writer Scardino also served as co-executive producer along with Ben Tishler. “I can’t believe other companies didn’t search these people out,” said Waxler.

No More Web Video for The Wire’s Doman
It just so happened actor John Doman, a regular on NBC’s “Law & Order” and “ER,” and HBO’s “The Wire,” where he played Major William Rawls, also had some time off. The star of MainStreet’s promo short “Mob Tactics,” Doman is no stranger to TV dramas, films or commercials. Yet even though he’s been seen in more than 50 TV spots, he has a lesser-known connection to the ad world. Before becoming a professional actor, he had a 14-year stint at TBWA Worldwide, where he worked on accounts such as Evian and Bombay Sapphire, along with computer and cosmetics products. Before jumping full force into acting, “I was sort of leading a secret double life,” said Doman.

His TV ad experiences typically have been quite different from the hour or two he spent shooting the one-minute MainStreet video. The script was “very loose” and the camera handheld, according to Doman, who told ClickZ the production was much smaller than the typical TV ad shoot. In Mob Tactics, his character is a gruff fellow not unlike the one he played on The Wire. He sits in a dank office cubicle sifting through notices referring to his poor credit score and tax debt, an unlit cigarette perched in his mouth.

“No, no, no,” he sneers, smacking his face in frustration. “This is not the way this is gonna happen.” Then the strong-arming ensues. He proceeds to taunt and threaten the paperwork as though it’s a thug cornered in an alley. He slaps it, spits on it, lights it on fire, and then submerges it in a vase filled with water, obviously a temporary relief presaging more torture. “What works in the movies won’t work for your bills,” declares a voiceover, suggesting better financial ideas can be found at MainStreet.com.

“It was kind of fun spoofing my character,” said Doman. Still, don’t expect him to be in any other Web-only productions anytime soon. “It was kind of a one-off,” he said. Until the Screen Actors Guild determines a compensation structure for content distributed online, as the Writers Guild did recently, “I wouldn’t do anything significant that’s shot for the Web,” he continued. SAG aims to avoid a strike and has scheduled contract talks with film and TV firms to start April 15.

Added Doman, “It’s definitely something important for SAG to settle on because more and more stuff will be shot exclusively for the Web.”