[2] In 1959, along with poets Allen Ginsberg, John Kelly, A. D. Winans, and William Margolis, he was one of the founders of Beatitude poetry magazine, where he also worked as an editor.

During Kaufman's time at The New School and in New York, he found inspiration in the writings of Herman Melville, Walt Whitman, Arthur Rimbaud, Guillaume Apollinaire, Federico García Lorca, Hart Crane, Gertrude Stein, Langston Hughes, Frantz Fanon, Aimé Césaire, and Nicolás Guillén.

[7] City Lights published several books of Kaufman's poems during his lifetime, however, including Abomunist Manifesto, Second April in 1959, and Does the Secret Mind Whisper in 1960.

[8] "Sitting here writing things on paper Instead of sticking the pencil into the air" From "Jail Poems" Although he was baptized at age 35 while in the Merchant Marines (Cherkovski, xxxiii), like many beat writers, Kaufman became a Buddhist.

On his release, Kaufman lived in the same building as Allen Ginsberg, where he met Timothy Leary in January 1961, and took psilocybin along with Jack Kerouac, apparently for the first time.

[13] In 1963 when he was to depart New York, he was summarily arrested for walking on the grass of Washington Square Park and incarcerated on Rikers Island, then sent as a "behavioral problem" to Bellevue Psychiatric Hospital where he underwent electro-shock treatments, which greatly affected his already bleak outlook on society.

[14][15][16] In an interview, Ken Kesey described seeing Bob Kaufman on the streets of San Francisco's North Beach during a visit to that city with his family in the 1950s: His poetry made use of jazz syncopation and meter.

The critic Raymond Foye wrote about him, "Adapting the harmonic complexities and spontaneous invention of bebop to poetic euphony and meter, he became the quintessential jazz poet.

His technique resembled that of the surreal school of poets, ranging from a powerful, visionary lyricism of satirical, near dadaistic leanings, to the more prophetic tone that can be found in his political poems.