How To Build Company After Company Brian Will is a serial entrepreneur who has created or co-created six very successful companies in four different industries over the last thirty-five years. His first foray into owning his own business was a 10-year stint in the landscaping industry that he started when he was twenty years old. This was followed by three online internet companies during the dot.com boom of the late nineties and early 2000s. The first was an online health insurance website and call centre that was eventually sold to a venture capital company in Silicon Valley and today is one of the largest online Medicare insurance platforms in the US. The second was an online “lead generation” company in the subprime credit space that was sold to a private equity firm out of Chicago. The third was another online health insurance website and call centre that was sold to another venture capital company in Silicon Valley and today is one of the largest individual state health insurance exchange platforms.