The company was founded by his father and about 90% of his net worth is held in shares of the insurance company.
The "Forbes 400 Richest Americans" list for 2011 ranked Lewis at #365, estimating his net worth as $1.1 billion.
Lewis is a major donor to ballot initiatives that support the legalization of medical marijuana and marijuana in general. He is the chairman of the Board of Directors of the Marijuana Policy Project.
New Zealand arrest
Lewis was arrested in Auckland, New Zealand in 2000 for importing cannabis resin and leaf. He was visiting New Zealand in the summer of 2000 to watch the America's Cup when these events transpired. After pleading guilty to three counts and agreeing to give $53,000 to a drug rehabilitation center in Auckland, the Otahuhu District Court discharged him without conviction. His lawyer told the Otahuhu court that Lewis uses marijuana to cope with pain from a partial leg amputation. The partial amputation occurred in 1998.
Lewis joined Progressive Insurance in 1955 as an underwriting trainee and became the company's CEO in 1965. He stepped down from his position as CEO in 2000, following his arrest in New Zealand, but retained his position as chairman of the company.