Prior to Ensight, Bill was a leader in the San Diego venture capital (VC) community with Tech Coast Angels, acting as an investor, board member, and advisor for several businesses in the cyber security, consumer product, and communications technology sectors.

As CEO of Anonymizer (2000-2011), Bill led the firm in the cyber security sector, providing subscription services to the U.S. government and large enterprise customers for online covert communications and non-attribution/identity services for cyber operations against opponents such as foreign opponents, terrorists, and hackers.