Our latest On Target podcast guest Mark Canon has a unique way to describe his long tenure in the local/SMB space. “I have used more of other people’s money to learn things than pretty much anyone else.”

Canon is currently CEO of Boomtime, a New Mexico based company that sits in the “conversational marketing” space, with word of mouth optimized websites as a core offering. Canon describes the business this way:

“We manage conversations for small businesses. The people [SMBs] are trying to reach are so blasted with messages of one sort or another that it is difficult to get their message across…Basically what we do is amplify the signals that small businesses get from the people in their communities who recommend them.”

The main reason for the On Target conversation recorded with Canon over the weekend was to tap into his long experience building SMB software products. We wanted his take on the complexities and challenges of moving small businesses into the cloud.

Canon’s career has centered almost exclusively on selling digital advertising and marketing products to small businesses, dating back to the 1996 founding of Switchboard.com, one of the first Internet Yellow Pages products. Later stops, including AOL, Autobytel and hibu, where Canon was chief digital officer, rounded out his education.

Canon has an at times contrarian view of small business tech adoption, in particular the notion of building integrated full-stack solutions for SMBs. These are product suites that may combine CRM with email marketing, payments and point of sale, appointment booking and so on. Canon says two things are routinely underestimated — the small business’s risk aversion and the challenges involved in successfully integrating a complex suite of products.

“One of the central problems of this tech adoption curve is people have to have a mental model of how they are going to use this stuff [cloud software]. And they have to be able to integrate it into the workflow of their daily activities. And that is a challenging thing for small businesses,” Canon said.

Canon thinks a more realistic path for SMB cloud software companies is to win loyalty with one solution and gradually build from there, rather than go straight for the full stack.

“My personal belief is that you want to solve the biggest problem with one product. And then get them to adopt the next one. Because if you sell them a whole stack of products, what is going to happen is they (small businesses) are more likely to fail in a bunch of these because they can’t put in the time and energy to carry it through to the end,” Canon said.

We asked Canon for the best example of a company that has followed his suggested path of solving one problem exceedingly well and then adding services over a longer time horizon. He cited Quickbooks.

“You start with the basic and it takes about six months to figure it out, and after a year you are an expert. Then you might look at their payroll/HR solution,: Canon said. “But think about the amount of time this takes. These are high impact decisions.”

You can listen to the full podcast here:

Canon will be speaking at the LSA’s Tech Adoption Summit in San Francisco on November 7. Check out the Tech Adoption Index website for more information on attending, speaking at or sponsoring the Summit.