The Longest Shortest Time(s)
Hillary Frank launched her podcast The Longest Shortest Time twice during two very different eras of podcasting’s evolution. We talk about what’s the same and what's different.
Welcome to Dispatch #85 of The Audio Insurgent.
Most of us have moments where we wonder what would happen if we got another shot at something. Sometimes the first attempt went well and we imagine repeating or improving on it. Other times it went badly and we replay it in our heads, convinced we’d do it differently now. In theory, experience is supposed to be useful that way. In practice, though, very few people actually get the chance to try the same thing again.
I recently had a conversation with Hillary Frank, host and creator of The Longest Shortest Time, a podcast about parenthood and reproductive health that she first launched in 2010 and relaunched at the beginning of 2025. I wanted to talk to her because she’s done something that very few podcasters have done: she’s launched the same show twice, in two very different eras of podcasting.
Let’s get to it…
[THE LONGEST SHORTEST TIME(S)] The first time Hillary Frank launched her podcast, very few people even knew what a podcast was. It was the early 2010s during podcasting’s frontier days—when Roman Mars was Kickstarting 99% Invisible and the medium felt wide open. Lots of people saw the possibility, but very few people were actually trying to make it happen. The show had a great run during those years (gathering a significant following while paying for itself), but then Hillary put the show on pause. Last year, long after the venture capital gold rush, the consolidation, the layoffs, and what many are calling the podcasting recession, she relaunched the show a second time.
When she announced she was bringing it back, my first thought was “I wonder how it is the same or different?” So I asked.
Hillary’s experience illustrates something I think is essential for everyone in our industry to understand: how fundamentally the business of making podcasts has changed, even when the creative work remains largely the same.
Hillary started The Longest Shortest Time completely on her own in 2010. She’d been freelancing in public radio for a decade, had just had a baby, and wanted to keep her foot in the door professionally. But it was also personal.
“I had had a really rough childbirth and recovery and wanted to be connected with other people who were willing to talk about early parenthood in a real way,” she told me. “So I started making episodes. I did it in a way that nobody would advise me to do now, which was I put them out whenever I could. I didn’t have a cadence. So over the first three years I put out 20 episodes and I made them while my daughter was napping, basically.”
Three years in, she decided to either make it her job or set it aside. And like so many well and ill-intentioned people do, many discouraged her. She launched a Kickstarter with a goal of $25,000. Many told her she wouldn’t be able to do it—including, as she put it, “people who are like, from our world, who should be supportive of independent people like me.”
Despite the skepticism, she raised $35,000, combining listener contributions with matching grants from brands like Medela and diapers.com. That success led to a partnership with WNYC, which gave Hillary her first producer and some marketing support. A year and a half later, she moved the show.
And that’s when things really changed.
“The last time I was in regular production, I was in partnership with Stitcher,” Hillary explained. “I had really all the support I needed, financially, to pay me a decent salary and to cover a small staff: primarily a full-time producer that was employed by Stitcher. I was independent. But I had engineering support. I had marketing support, I had a story editor. All of that was covered by Stitcher. So I had not only financial support, but I also had institutional support.”
Her ad inventory was consistently sold out. And despite people in the industry telling her she’d never be financially successful with a show about parenthood, she proved them wrong. “I was like, ‘Well, but aren’t moms the most coveted audience for sponsors?’ And that turned out to be true. And so the show was one of the first self-sustaining shows in podcasting. And I’m really proud of that.”
She saw the show through a few evolutionary steps, then put it on pause in 2019.
Fast forward to early 2025. Hillary decided to bring the show back. She’d been consulting and working on some other projects for a few years, but projects kept disappearing due to layoffs, and the work felt unstable. She also felt called back to the subject matter. Her daughter was now a teen—and there were important conversations around reproductive health that needed to happen.
“I will bring it back and I will have a slightly renewed focus for the show and it’ll be great.”
Despite all the pull backs in podcasting, she was pleasantly surprised that she had her pick of companies that wanted to partner with her. But what they were offering was completely different.
“What people were offering was really ad sales deals. So, you know, a revenue share split,” she said. “I had a minimum guarantee before. So I got money up front, and regular, monthly income that could support me. And now the situation is, people are offering revenue shares.”
Despite the financial struggles, the show is STILL sold out. She’s just making far less for it now. And her income is based entirely on ad sales, so the amount fluctuates.
As Hillary adds, “Advertising rates are lower than they were before. What counted as a download is not what counts as a download anymore. So the amount that I can make per episode is very different. And I’m getting no production support. And so if I want to have production support, I need to pay somebody out of pocket.”
She paused. “And I don’t have enough yet to even support me.”
The payment terms are also different. “The way you get paid is at best 60 days after your episode airs and that’s like the best case scenario. Often it’s four months after.”
And she’s doing almost everything herself now—booking, cutting tape, marketing, uploading episodes. The only support she has is a friend doing mixing at a reduced rate and someone who volunteers a couple hours a week to cut ads and narration, and QC episodes.
“It’s a struggle.”
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“It’s really hard to get noticed if you’re not a celebrity and it’s hard to make money if you’re not a celebrity.”
Beyond the economics of the second launch of the show, there are structural challenges that weren’t there before, too.
“It’s harder to develop audience than it was last time around,” Hillary told me. “There’s a lot more podcasts, but what they’re doing is very different than what I do. Most of them, especially in the parenting space, are chat shows either unedited or very lightly edited. So they’re like chat shows that come out more than once a week and I can’t keep up with that pace if I’m going to keep the show what it is and what I think people love about it.”
One thing I was surprised to hear from her: Hillary thinks, despite the changes in podcasting’s profile and expansion of who listens, the audience for her show seems largely unchanged—very similar people, still engaged, still valuing the stories. But one thing that has changed: Hillary’s relationship with that audience.
The show has less direct contact now. During her first run, she had a producer who managed a lot of this and ran Hillary’s social channels. Today, on her own, the limited amount of time she has is mostly focused on interacting with paid members on SupportingCast rather than through open social media and website comments.
I asked her if that was good or bad.
“It’s like good and bad,” she said. “I think I’m shielding myself from toxic messaging. If I’m making the show by myself, I have to preserve my mental health and my energy. And so by shielding myself, I’m also shielding myself from a lot of the great interactions too.”
I asked Hillary if, given the challenges of this year, she could go back in a time machine to right when she was about to make the decision to bring the show back, would she advise herself to do it or not?
“I would say go for it, but I would also say it’s not gonna be the same as it was, and it’s not gonna be easy.”
“I’m glad I brought the show back,” she said. “I am really proud of the episodes I’ve been doing, and I think that I’m contributing to conversations around reproductive health that really need to be had. And I have a platform to do that and I’m really happy to be doing that. I don’t know how sustainable this is, and I am giving it a go to see.”
I asked if she still feels hopeful.
“I don’t feel as hopeful as I did when I was starting back up. It’s just harder to see the path forward.”
But she also said, she’s been at this junction before. “Do you remember back in like 2007? 2006? When [public radio] shows were shutting down like Weekend America and Day to Day. I had been making my living freelancing for shows like that. I was actually a contract editor at Weekend America when it got shut down and it was devastating. And I was like, ‘Alright, well. I’m not gonna have a future in audio.’ So I started looking for jobs in advertising. And then podcasting showed up and it offered me a new way forward. And so, in a lot of ways, things are feeling not very hopeful, but I keep wondering, is there gonna be a new way forward?”
While I first wanted to chat with Hillary because I thought it would illustrate how different things were, I didn’t expect to walk away with such a clear-eyed summation of where podcasting is right now: the easy money and institutions with money to spend that emerged during podcasting’s growth years (along with the guaranteed salaries, the production teams, the marketing departments, the story editors)--that’s gone. What’s replaced it is a return to DIY production, but with the added challenge of competing in an exponentially more crowded landscape where the economic incentives favor high-frequency, low-production-value content.
Hillary is still making the show. She’s still reaching people. She’s still doing important work. But her story is also about what sustainability looks like in podcasting when the “dumb money” era is over, when contraction has stripped away infrastructure, and when the “build it and they will come” optimism of podcasting’s early days runs headfirst into the reality of a spreadsheet.
And here’s something really important to take away from Hillary’s experience: she’s proven people wrong before. Multiple times. She was told she couldn’t raise money on Kickstarter. She did. She was told a parenting podcast couldn’t be financially successful. It was. She built something from nothing, twice.
So one lesson from this: don’t listen to people telling you what you can’t do. 😉
But that aside, it’s telling that even someone with that track record is finding the current landscape punishing in ways that have nothing to do with the quality of the work or the connection with an audience.
Since we spoke late last year, Hillary has continued to experience some headache-inducing setbacks (a bot locked her out of her social channels for discussing reproductive health)–and scored some wins. She’s earning a bit more now, and is channeling that into hiring some very part time help (she’s taking applications if you are interested).
HIllary’s experience reveals what “sustainability” actually looks like in this new era. And in figuring out how to make it work this time, she’s probably showing the rest of us what podcasting looks like on the other side of all this.
Okay, that’s it for today.
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Make great things. I’ll be listening.
--Eric