Early career After his freshman year, 19-year-old Glass looked around Baltimore for work in television, radio, and advertising without success; After someone at the local rock station recommended that he seek out Jay Kernis at National Public Radio's headquarters in
Washington, D.C., Talbot brought Glass with him to New York between 1986-87 as an intern on
Kids America produced at
WNYC. In Glass' half-hour weekly segments, he took the on-air persona of "Bob" and asked opinion poll style questions. Glass returned to DC and worked at NPR for 17 years, where he eventually graduated to being a tape-cutter, before becoming a reporter and host on several NPR programs, including
Morning Edition,
All Things Considered, and
Talk of the Nation. In an interview, Glass recalled that his first show was with NPR's
Joe Frank, and says the experience influenced him in a "huge way", adding: "Before I saw Joe put together a show, I had never thought about radio as a place where you could tell a certain kind of story." He has also said that editing for
Noah Adams, an early host of
All Things Considered, taught him how "to step back from the action and move to some bigger thought and then return to the plot", a technique that he still uses to structure
This American Life. During this time, he dated a lawyer for seven years who, according to him, made him feel terrible and did not take his work seriously or love him. He says that while she was away working in Texas, he felt his writing improved in her absence, and their relationship ended by the end of the summer. In 1989, Glass followed his then-girlfriend, cartoonist
Lynda Barry, to Chicago and settled into the
Lakeview neighborhood. During this time they spent two years reporting on the
Chicago Public Schools—one year at a high school, and another at an elementary school. The largest finding of their investigations was that smaller class sizes would contribute to more success in impoverished, inner-city schools. Glass eventually tired of "free-form radio" and, looking at other opportunities, began sending grant proposals to the
Corporation for Public Broadcasting. The show—then called
Your Radio Playhouse—first aired on November 17, 1995; the episode was titled "New Beginnings". It included interviews with talk-show host
Joe Franklin and Shirley Glass—who maintained her position that her son should consider work in television because of his resemblance to
Hugh Grant—as well as stories by
Kevin Kelly (the founding editor of
Wired) and performance artist
Lawrence Steger. and was syndicated nationally in June 1996 by
Public Radio International after NPR passed on it. Glass devoted himself to the effort by making the daily commute from his
North Side apartment and spending 70 to 80 hours per week in the offices on the
Navy Pier. The show aired for thirteen episodes over two seasons before ending in 2009 because of the heavy workload needed to produce it. Chicago Public Media announced it would begin self-distribution of
This American Life starting on July 1, 2014, through
Public Radio Exchange (PRX). By 2020,
This American Life reached more than 4.7 million listeners each week. For the 2013 fiscal year, the WBEZ board voted to raise Glass's salary from $170,000 annually to $278,000. However, he requested that it be lowered to $146,000 the following year, and has since asked for it be lowered again, calling the original sum "unseemly". He supplements his income with speaking engagements, which earn him "five figures per talk".
Other works Outside of radio, Glass has also worked as a print author. In September 1999, he collaborated on a comic book,
Radio: An Illustrated Guide, with
Jessica Abel. The book describes how
This American Life is produced and instructs the reader into building their own radio program. In October 2007, he published the anthology
The New Kings of Nonfiction. Glass has collaborated on several feature films. In the show's contract with
Warner Bros.,
This American Life has first pick options on any films that emerge from stories of that program. By extension, Glass goes to Warner Bros. with any movie idea he may have. In 2006, he was an executive producer of the feature film
Unaccompanied Minors, which is based on the true story of what happened to
This American Life contributing editor Susan Burton and her sister Betsy at an airport one day before Christmas. Burton had already produced a segment on
This American Life about the same experience before the story was adapted to film. In 2007, he and
Dylan Kidd wrote a screenplay based on the nonfiction book
Urban Tribes about a man who must choose between his friends and his girlfriend. Glass also produced the 2018 Netflix movie
Come Sunday. Glass regularly collaborates with comedian
Mike Birbiglia. In 2012, Glass co-wrote and produced Birbiglia's film
Sleepwalk with Me and they both went on a country-wide promotional tour for the film to give interviews and visit theaters to introduce the film. On September 17, 2012, Glass made a special voice appearance on
The Colbert Report with
Stephen Colbert to promote
Sleepwalk with Me and invite Colbert to participate in a
This American Life episode. Glass was credited as a co-producer in Birbiglia's 2016 film ''
Don't Think Twice'', alongside Miranda Bailey and Amanda Marshall. Glass is also the producer for Birbiglia's 2018 one-man
Broadway show
The New One. In 2013, Glass partnered with Monica Bill Barnes & Company to produce
Three Acts, Two Dancers, One Radio Host and worked alongside Monica Bill Barnes and Anna Bass. Glass toured Google's headquarters in November 2013 and met the
Google Doodle team, who collectively agreed to collaborate with
This American Life. Glass suggested that for
Valentine's Day 2014 they interview "random" people about their experiences with love. Users in the American market could click on a
candy heart that corresponded to each letter in "Google" and listen to a different story of unusual love in the same style as the radio program. ==Tours==