One might say that Hillary Frank took an unusual route in becoming a radio producer. The host and creator of the leading parenting podcast, “The Longest Shortest Time,” actually got her start using a cassette boombox and an answering machine. On episode 103 of “The Wolf Den,” Hillary told the story to host and Midroll CEO Adam Sachs.
After sending a series of rejected pitches to “This American Life,” she sent an email directly to creator Ira Glass, that got answered by an administrative assistant who told Hillary the upcoming themes for the show. One theme was “apocalypse,” so she produced a story about a friend that was obsessed with the end of the world, using just those aforementioned audio tools. Then she FedEx’d it to the senior producer.
The next day Hillary–who was then in graduate school for classical drawing–was in a seminar learning to draw an actual cadaver, when she got a phone message from Ira. “Who are you? How did you figure out how do something for our show?” he asked. “Let’s talk.”
She took a break from the seminar to call him back, and Ira encouraged her to keep pitching stories. They weren’t able to use that first “apocalypse” segment, but asked her to produce another one using the same analog style.
While Hillary has since graduated from tape recorders and microcassette answering machines, her unique introduction to radio informs her truly unconventional advice to aspiring podcasters.
“Listen to people’s rules about what you need to do in order to be sucessful, and then break them,” she said. “And then prove that they’re not true. Because I got on the radio with a boombox and an answering machine. And I got into podcasting on a schedule that makes no sense.”
Hillary continued, “I think you have to be creative about how you’re approaching people and approaching the medium, because the truth that nobody tells you about getting into a job in the media is that people are always always always looking for new talent… and they’re especially looking for diverse talent. And it’s much harder to find competent people than it seems.”
Even though there is a large pool of people wanting to get into the media, the number of individuals who are exceptional is actually quite tiny.
So, Hillary advised, “the way to prove that you are one of those people is to break the rules and show that you have creative smart interpretations of how to actually do this stuff.”
Listen to the whole episode to learn more about Hillary’s path from radio freelancer to podcast host, and how humor figures into a parenting show that’s for everyone.