On a recent Friday afternoon 25-year-old Mike Salvatore was standing on the back porch of a Lincoln Park three-flat gripping the bottom of a 12-foot ladder leading to the roof. His friend Jordan Shea had just climbed up and was straddling the peak with a staple gun in hand. “Do me a favor,” Salvatore called up to him. “Don’t kill yourself, please.” Then a train roared by no more than four feet from the roof’s edge. “Shit,” Salvatore laughed nervously. “If that ladder slips, we’re screwed.”

Salvatore and Shea knew what they were doing was risky, but the roof was in full view of northbound trains on the Red, Purple, and Brown lines, and they were hanging a banner advertising Salvatore’s fledgling business. “AudioSnacks,” it read in large black letters. “MP3 Audio Tours for Travel, Museums and More! Help Spread the World!”

AudioSnacks offers downloadable audio tours of cities as far-flung as Paris, Cape Town, and Victoria, British Columbia. But unlike Walki-Talki, ARTineraries, Podguides.co.uk, and other similar ventures, it doesn’t produce its tours–it wants its users to. “You have these traditional tour guides who are happy to host, but they’re doing the same things you could get out of a book,” Salvatore says. “It’s the unique ones with the personal touch that I’m excited about.”

Salvatore got the idea for AudioSnacks in February 2005, a month after he quit his job trading at the Chicago Stock Exchange. “It wasn’t something I was passionate about,” he says. “I had high blood pressure. I was grouchy all the time.” He’d decided to do some traveling and was standing in the basement of a church in Florence puzzling over a plaque in Italian when he was struck by the potential of the iPod in his pocket. How great would it be, he thought, if his MP3 player could be his guide? He could listen to a tour without looking like a tourist or adhering to the schedule–and paying the cost–of a live one. Six months later he was back in Chicago formulating a business plan.

At first he intended to record all the tours himself and market them through electronic kiosks. “The original idea was immense,” he says. “I had electronic kiosks in every park where you could go and upload your tour. But each kiosk would have cost me $40,000 to $100,000, so it wasn’t going to work.”

Within months he was ready to throw in the towel. “People were telling me to get a job, my family didn’t get what I was doing, so I thought maybe I should give up,” he says. “I thought, someone’s going to do it anyway, with more money, and they’ll do it better than I can.”

In January 2006 Salvatore went back to work as an options trader at a small downtown investment firm. In the evenings and on the weekends, he dreamed about giving MP3 tours another shot. Four months later the solution came to him in the middle of the night: “I realized, who am I to try and give people advice when I’ve never been there, when there are locals who are passionate about this tour? I can go to the library and find facts and, yeah, you can regurgitate that, but do I want to listen to that?”

Salvatore says he was partly inspired by his great uncle John Laux, a photography hobbyist who traveled throughout the U.S., Europe, and South America. Several years earlier Salvatore had discovered Laux’s camera, prints, and negatives in his parents’ Edgewater basement and was moved by the intimacy of his work: “His images allow people today a glimpse of what one man saw.”

In April last year he quit his job and redoubled his efforts, this time envisioning a Web site to recruit guides and distribute the tours. He took a marketing class at DePaul, got involved with Chicago Beta, a club for Web startup entrepreneurs, and attended mixers like Tech Cocktail for local tech enthusiasts. He set up a MySpace page to befriend travel enthusiasts, blanketed Craigslist with ads for tour providers, and enlisted a college friend, Tom White, to build the site.

In June he found his first tour guide. Chicago freelance writer Philip Berger put together a 30-minute walking tour of the architecture of Dearborn Street and recorded it in Salvatore’s living room, using Salvatore’s brother’s eight-track recorder. Berger is an earnest, soft-spoken guide. “In many ways,” he says of the Marquette Building, “it is the archetypal Chicago-school building. But what’s really great about the building is the interior decoration in the lobby. You really have to go inside and take a look. . . .”

Salvatore launched the site in August selling Berger’s tour for $10. To beef up his roster he added some professional audio tours by the likes of Audissey Guides and Great Discoveries. He’s now got about 90 tours of more than 40 cities, ranging from 20 minutes to three hours and priced up to $19, although many are free. To encourage people to post original tours, he’s added a step-by-step tutorial including technical advice. “I think the more creative, the more personal you are, the better that tour’s gonna turn out,” he says. “Your voice projects your feelings about the tour to the audience.”

Anja HK is among the amateur guides. In German-accented English she offers a “Third Reich Tour” of Berlin, including stops at the Brandenburg Gate and the former site of the Fuhrerbunker: “Today we will give you some insight of the most horrifying era of Germany’s history that still causes puzzlement about how the so-called ‘little man’ was capable of crimes so cruel that you have to force yourself to read or hear about them,” she says.

Tour providers retain copyrights, set prices, and take home 80 percent of sales. (For the mike shy, AudioSnacks will record a prepared script for a fee.) Profits are paid quarterly by electronic check or deposited into an online account. Tour providers are required to sign a contract to protect against fraud and viruses, and Salvatore monitors the site closely. When someone attempted to upload and charge for an MP3 tour owned by the Boston Globe, he permanently deleted the user’s account.

Salvatore recently added a bulletin board where travelers can exchange tips, and he’s issued calls to college students to record tours of their campuses and to Chicago aldermen to offer tours of their wards. So far only four students have expressed interest, and there’s been no word from the aldermen. Salvatore hasn’t given up hope: “Who better to give tours of areas than the people who are chosen to govern them?”

So far the site is averaging five to six downloads a day and bringing in about $100 a month. Until things pick up, Salvatore has other means of support. An exhibition during Andersonville’s annual Arts Weekend last fall prompted some interest in his great uncle’s black-and-white travel photos. They’re selling at a rate of one or two a week for $500 to $1,000 apiece.

Thanks to this unexpected source of cash, Salvatore can focus on the tour business. “I quit a job and a career to do this,” he says. “I’m using my own money. I can’t think about the possibility of it failing.”

Art accompanying story in printed newspaper (not available in this archive): photo/Carlos J. Ortiz.