The cyclist was in the bicycle lane when he was struck, KCAL-TV reported, citing investigators. He landed on the windshield, shattering the glass before rolling off the cruiser to the street.
The deputy, who was not named, was taken to a hospital for treatment of cuts and bruises.
The cause of the crash was under investigation.
In addition to once serving as a top executive for Napster, the 65-year-old Olin was a prominent entertainment attorney for Altschul & Olin LLP, which he co-founded, the Los Angeles Times reported.
Prior to Napster, Olin worked for Firstlook.com, an start-up that offered previews of movies, music and games, and for A&M Records as vice president of business development and was responsible for signing artists and acquiring music rights.
Napster was a pioneer in online music sharing, leading to lawsuits by Metallica and other acts in 2000. The suits eventually forced a settlement that required Napster to evolve into a pay-for-use service that became something of a model for today's streaming companies.