John Osterlind was born on March 10, 1967, in Norwalk, Connecticut. In 1985, he received his diploma from Roger Ludlowe High School in Fairfield, Connecticut. In 1987, he graduated from Dean Jr. College in Franklin, Massachusetts, where he worked as a DJ for their campus radio station, 88.3 FM WGAO.
From 1987 to 1988, He broadcast overnights on 103.7 FM WWRX, a classic rock station in Providence, Rhode Island.
He broadcast in the afternoons and evenings on the rock station WCCC-FM in Hartford, Connecticut, from 1989 to 1992.
He also broadcast in the evenings on the rock station WAAF FM in Boston, Massachusetts. From 1992 to 1994, and from 1994 to 2001. On WAAF, he was the midday jock and music director.
From 2001 to 2003, he co-hosted the morning show on WRKO AM in Boston with former Massachusetts congressman Peter Blute.
He was the popular evening talk host on WRNO FM in New Orleans, Louisiana. Until the evening of January 7, 2015.
The bogus non-profit “Pencils for Poor People,” which Osterlind and his producer James Parker invented as one of the many running jokes on The John Osterlind Show. Served as the inspiration for the protest Osterlind’s New Orleans supporters staged against WRNO after his firing.
After leaving WGSO on November 2, 2015. Osterlind hosted the morning drive-time show on 95.7 FM BAYOU before being eventually replaced by a syndicated program The WISE Guys. Osterlind then started broadcasting middays on WGSO 990 AM in New Orleans.