After arriving in San Francisco and working as a bike messenger, Whitaker became involved with the city's Beat and later hippie cultural scenes in both
North Beach and the
Haight-Ashbury District. He spent time among writers and artists connected to the Beat movement and later participated in political and artistic networks associated with the city's counterculture including involvement with the
Rainbow Family,
the Diggers, and the Black Man's Free Store in the
Fillmore District. He met
Lawrence Ferlinghetti,
Jack Kerouac,
Neal Cassady,
Richard Brautigan,
Ken Kesey, and "Father of the Beats"
Kenneth Rexroth. "Diamond Dave" traveled to Paris and met French thinkers like
Cornelius Castoriadis, witnessed
Dr. Martin Luther King Jr.'s "
I Have A Dream" speech in
Washington, D.C. in 1963, rode the
Furthur bus to the
Human Be-In in 1967, and attended the 'Death of the Hippies' funeral during the
Summer of Love. Whitaker was also known for organizing inclusive poetry readings and public cultural events including
Poetry Under the Dome, San Francisco's largest open-mic poetry gathering which was held at
San Francisco City Hall from its beginning in 2005; "Diamond Dave" participated until 2025.
John Avalos,
Aaron Peskin and
David Campos made appearances at these events.
Community radio Whitaker was involved in community
broadcasting for many years as one of the first hosts and organizers of independent Bay Area station
KPOO 98.5 serving low-income communities. He co-hosted the weekly three-hour
open-mic radio program Common Thread Collective, which aired from San Francisco's
Mission District. The show featured
spoken-word poetry,
music,
political expression, and discussions with local and international artists and activists. The program originally aired on Pirate Cat Radio, a community-run
pirate radio station, and later continued on Mutiny Radio after Pirate Cat ceased terrestrial broadcasting. Along with fellow DJs, Whitaker participated in and reported on the
Occupy Wall Street and other protest movements, even camping at
Embarcadero Plaza. His eccentric style of verbal delivery consisted of improvisational
stream-of-consciousness rhyming poetry and he was known for
catchphrases such as "don't panic, keep it
organic", "history, herstory, and hipstory", "doing more together than any of us can do on our own", "strangers become friends, friends become family, family becomes community", and "cast a wide net and find the common thread."
Education and civic engagement Whitaker maintained an active presence at
City College of San Francisco, where he took regular classes and participated in
student government activities. He served several terms as the oldest senator in the Associated Student Council and helped organize student protests in defense of the college during the accreditation crisis in 2012. == Later life and death ==