Jesse got his start in journalism as the news and features editor at Hunter College’s oldest newspaper, the Envoy. The following year, he won the Murray Kempton Award for Journalism in the category of news reporting for his expose on student activity funds entitled “The Green Initiative Referendum: Why You're Funding a Magazine That Doesn't Exist.”

In 2011, he graduated cum laude from Hunter with a B.A. in political science. That same year, Jesse was honored with the James Aronson Award for Social Justice Journalism for his reporting on homelessness and prostitution in the South Bronx, for the neighborhood newspaper the Hunts Point Express. He spent the next two years reporting on New York City crime, politics, housing and culture, first for the Bay Ridge-based newspapers the Home Reporter and the Brooklyn Spectator, then later for the citywide hyperlocal website DNAinfo. While covering breaking news for the latter publication, Jesse reported on such major events as Hurricane Sandy, the Occupy Wall Street protests and the 2012 presidential election.

His writing has been featured in the Huffington Post, the Queens Courier, the Wall Street Journal’s Financial Advisers blog, the websites Brooklyn Based and Evolved Employer and the magazines Restaurant Business and Periscope.

In late 2016, he became the host of the radio talk show TrumpWatch with Jesse Lent on WBAI New York 99.5FM. Guests included Robert Costa, David Cay Johnston and Alec Baldwin.

The following year, Jesse became the executive producer of Leonard Lopate at Large as the three-time James Beard Award winning broadcaster made the transition to WBAI. Assisting in all aspects of writing, booking and developing the direction of the show, he has even served as the occasional co-host. Guests during his time with the show have included Jesse Wegman of the New York Times editorial board, former Trump campaign staffer George Papadopoulos, activist Shaun King, actor Tim Robbins, Wayne Kramer of The MC5, trombonist Delfeayo Marsalis, presidential biographer Jon Meacham, Darrell Hammond of Saturday Night Live, choreographer Twyla Tharp, political commentator David Frum and novelist Ann Beattie.

In 2022 he began hosting the only show devoted to the Dutch music scene Streets of Fire with Jesse Lent on Broadcast Amsterdam (BRAM Radio).