Schumacher upgraded to an enterprise agreement from a Select license three years ago. But Menefee says constant re-evaluation makes sense, due to Microsoft's constantly changing licensing and product release dates.

Schumacher's other main vendor is .

"We get a huge return on investment from Salesforce. It drives all of our systems," he said. "We don't have an on-premises ERP system, we just take Salesforce.com as far as it can go."

Indeed, half of the software Schumacher uses is delivered as a service. Because of that, Schumacher's vendor list includes many smaller startups. Menefee is taking a close look at the "depth and financial stability" of those vendors, especially "if there is a chance that their outside investment could be pulled," leaving Schumacher without vendor support.

Still, Menefee, who worked at a dot-com during that period's boom and bust, doesn't expect the same massacre. "I think the industry learned a lot of lessons during the dot-bomb era," he said.