Bob began his career as a casualty underwriter for Pacific Indemnity Company (Chubb) and later for US Fire and Fireman’s Fund. Bob also served as chief executive officer of the well-known Anderson & Anderson Insurance Brokers. Over nearly 30 years, he built Anderson & Anderson from a four-person company into the fifth-largest brokerage firm in California before its sale to AON Corporation. At Aon, Bob was the president of the Aon Advantage Group, which advised 20 industry practice leaders, such as the Hospitality Group, which insured Hotels, Resorts, and Casinos. Bob attended the Harvard Business School’s OPM program, which is similar to its MBA program. He earned his CPCU (Chartered Property Casualty Underwriter) designation in 1970 from the American Institute for Property and Liability Underwriters, Inc.  Bob co-founded four Insurtech companies, interests in three were sold, and the remaining is TaylorWell, a small group employer platform in Seattle.