He currently hosts a morning radio program on KOCI 101.5 FM, a station located in south Orange County, California.

[citation needed] Under "The Poorman" moniker, Trenton wrote and self-published two guidebooks about dining in the Los Angeles area on a budget.

It began as a serious "public service" segment hosted by Mason, but Trenton revamped the format to a hybrid of advice and comedy.

[citation needed] As Trenton found himself unable to answer serious medical questions related to sexual issues, he added a segment called "Ask a Surgeon," and later "On Call with Dr. Drew," hosted by his friend Drew Pinsky, who at the time, was a fourth-year medical student at the University of Southern California.

In response, Trenton organized approximately 500 listeners to gather on the front lawn of Bean's house at midnight, to have their own celebration.

In late 2010, Trenton began one of various stints on the pay-your-own-way broadcast station KCAA, based out of San Bernardino, California.

[11] The show "Poorman's Radio Invasion", ended after about a year, at which point he moved to New York to prepare for his new syndicated program.

[12] Despite originally being promoted as a live call-in show, Poorman's Nation instead consisted solely of taped interviews from Occupy Wall Street.

Trenton conducted his on-the-street interviews while wearing only a Depression-era-style barrel, which earned him some degree of media attention, including an appearance on The Young Turks.

While working at KROQ in the mid-1980s, local Orange County TV station KDOC had a program called Adventures with the Poorman hosted by Trenton.

[citation needed] In 1994 Trenton launched a live, late-night call-in TV advice show called The Love Channel on KDOC.

[20] Trenton worked as a field reporter on KTTV's Good Day LA and the Los Angeles UPN station's news program.

Trenton has also appeared in four films, including the 1987 B movie North Shore as the opening surf contest announcer, the 1988 hit Heathers (as the 'Hot Probs' D.J.)