• by Karl Greenberg , March 15, 2011

Cadillac is showcasing American entrepreneurs who are "fearlessly individual, unfazed by risk," and "relentlessly optimistic," as part of a program developed with Time Warner and distributed through CNNMoney.com.

"Business Unusual" centers on a series of documentary-style Web videos that started on Feb. 28, featuring blogger, comedian and invention enthusiast Chris Hardwick, who takes a road trip to find stories of entrepreneurs: those who have taken a risk and turned an idea into a successful business. The underlying idea is that these people embody Cadillac's brand identity, and also the ideal Cadillac customer.

The video content is framed by Cadillac ads and product-focused videos, as well as companion pieces on entrepreneurial lessons for each episode. The microsite also has links to Cadillac brand destinations via ad units and hot-linked content, social media applications and links to Time articles. Cadillac and Time-Warner are launching new videos roughly every two weeks.

Sherrie Weitzman, Cadillac's national advertising manager, tells Marketing Daily that the joint initiative stems from work the media company did for Cadillac around the launch of the 2010 SRX crossover. "We briefed them on what we were trying to do in the broad sense. They came back with a couple of things that we merged to make this one. One was a road trip where driving sequences were the focus with points of interest less of a topic; then they also had the notion of exploring entrepreneurs, risk takers -- people who do things their own way. So this is not about Chris Hardwick taking a road trip, driving from place to place; it's a synergy, spirit, process and design story."

Weitzman says that the entrepreneurs are chosen based on how their business can be seen as a metaphor for Cadillac's own efforts. An upcoming episode features "Bike Monkey," about a man who left corporate America to start a bicycle racing performance-engineering firm. "The cool thing about it is that the basis of his interest in bicycle racing is engineering for performance, both in terms of individual racers and equipment. That's an aesthetic that is very similar to what we do at Cadillac," she says. "It is not only about the right demographic and business story, but something within the context of his or her business that is similar or in parallel to what we are doing."

Another episode focuses on "Fran's Chocolates," a company started by artisan chocolate maker Fran Bigelow in Seattle, whose products are distributed to stores like Zabar's in New York, and whose fans include President Obama. "Her attention to detail is very parallel to what we do in terms of interiors -- the double stitching, choice of woods, overall interior harmony. So you might wonder what chocolate and cars have to do with each other, but the parallel is artistry and craftsmanship."

Weitzman says there are six episodes in the can, "And we have six more we will film over the next couple of months." She says the videos will run through the second quarter, with CNNmoney.com the sole point of distribution. The initial episodes feature entrepreneurs in the northwest region of the U.S., and the next six will be in the southeast and New York areas.