With origins in private equity, fund management and leveraged buyouts, in the early 2000’s he operated Internet Real Estate Group, a Web 2.0 studio in Boston which successfully developed businesses including Creditcards.com; Phone.com; Luggage.com; Jeans.com and a dozen other early primary domain businesses.

There, his pioneering team of engineers created some of the earliest successful affiliate marketing and advertising platforms on the Internet, and were early experts in search engine optimization.