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The Inside Story Behind Simon Kent Fung and Tenderfoot TV's Now-Hit Podcast "Dear Alana"
PLUS: Layoffs at New York Public Radio
Hello, Squeeze People!
If you’ve ever wondered what it would be like to pitch your show to some of the leading podcast production studios, today’s interview with Dear Alana creator Simon Kent Fung is for you. Simon chose to work with Tenderfoot TV for production and distribution and when the show launched this past August, it hit number one on Apple Podcasts in the U.S. and Canada in its first week. A spokesperson for Tenderfoot TV says that the show “is closing in” on two million downloads.
Before we get to that, a few quick notes:
By now, you’re probably aware that I’ve paused payments from paid subscribers while I deal with a family situation. I hope to return to more regular programming in about a month, but it depends on factors that are out of my control. In the meantime, I’m squeezing work in when and where I can (see what I did there?).
I’m hosting an inaugural feedback session for paid members of The Squeeze on Tuesday, October 10th at 12:30pm PT / 3:30pm ET / 8:30 pm GMT+1 on Zoom. I will bring a list of story ideas for the group to consider. Because I’m not accepting any new paid subscribers right now, if you desperately want to attend this Zoom, hit reply on this email and we’ll work it out.
You may have heard that New York Public Radio has announced that the company will lay off 12% (40 members) of its workforce. I wasn’t shocked by this news, as NYPR CEO Oliver LaFontaine warned of cost-cutting back in June, but union leaders are doing whatever they can to fight it. This week organization’s members made a presentation to leadership suggesting alternatives, and launched a public petition. Godspeed.
I’ve heard rumblings for months now about trouble at Sweet Fish, a business-to-business podcast production company. Those rumblings seem to be growing louder lately. If you have any information about this company that you think I should know, please do reach out.
Finally, given all the layoffs, I’m considering adding a jobs section to this newsletter. If you’ve got an open position to share, send it my way and please include compensation and benefits. To kick things off, check out this description for a lead producer position that’s just come up at The Podglomerate.
Moving on to today’s main event:
The Inside Story Behind Simon Kent Fung and Tenderfoot TV's Now-Hit Podcast Dear Alana
I met first-time podcaster Simon Kent Fung at an industry mixer in June of 2022. In between bites of hummus and falafel, Simon revealed that he was on the brink of choosing between several offers from well known podcast production and distribution companies for a narrative podcast he’d been developing for nearly a year. Intrigued — both by what he told me about the show and the position he was now in — I asked him to get in touch if he ever felt ready to dish about the experience of pitching his show, and he said he would.
Lucky for me, he made good on his promise this past June. “Dear Skye,” his email began. “We met at the KQED podcast mingle last summer, and you asked me to follow up with you. I was the independent making a show on my experiences in conversion therapy… Well here I am, a year late! I went with Tenderfoot and the show is leading their slate this year…”
Since then, I’ve had the pleasure of chatting with Simon more than once and am excited to present an edited version of our conversations today. As a special bonus, in my next issue, I’ll publish excerpts of a conversation I had with Tenderfoot TV’s CEO Donald Albright, who was intimately involved with the making of Dear Alana, and Tenderfoot’s lead on operations and partnerships, Tracy Leeds Kaplan, who played a pivotal role in bringing Simon’s show to the attention of her employer.
To be clear, today’s interview is focused on Simon’s process of finding a studio partner for Dear Alana — but I also recommend that you check out the actual show! Over the course of eight episodes, Simon traces the brief life of a young woman grappling with issues of faith, sexual identity, and belonging — a struggle that is familiar to Simon. The nuance found in Simon’s storytelling and the note-perfect way in which he weaves his own story into its narrative, make Dear Alana exceptional (and not necessarily a show I would have expected from Tenderfoot TV —but we’ll get to that).
This has been edited for clarity and length.
Skye: What was the driving force behind partnering with a studio for this show?
Simon: I was prepared to make the show independently because I felt very protective over Alana’s story; telling it required a certain level of nuance and sensitivity. So I wasn’t going to work with someone who didn’t respect that part of it. At the same time, I wanted to set the show up to reach as wide an audience as possible — people who were part of this unique subculture of Catholicism that Alana and I were part of, but also people who were not religious at all; people who just wanted to hear a human story. I was under no illusions that I could do that singularly.
Skye: How did you start?
Simon: After my first trip to Denver to visit Alana’s mom, I collected enough tape to make a fairly polished pilot episode. I had worked briefly in film production and I am a designer by trade, so those things helped. From there, I made a pitch deck that included imagery I had collected in Colorado, show art, episode art, a sort of mind map of the different themes the show would explore, some target demos, that sort of thing. And then I just started reaching out to anyone who would give me the time of day.
Skye: What did that mean in practice?
Simon: It meant messaging my old coworkers on LinkedIn, and making a list of anyone who I thought might be potentially adjacent to the industry. One of the earliest people I spoke with was a former colleague of mine from my days at Patreon, Tracy Leeds Kaplan, who was now at Tenderfoot TV. We were both living in San Francisco, so she came over to my apartment and helped me sort through the podcast ecosystem. Her advice was to start figuring out where the gaps were in what I was doing. I had been prepared to keep making the show myself but she prompted me to realize that bringing on more help made sense. I started thinking about finding some people to help with editing or producing, and maybe someone who wasn’t religious and could provide an “outsider’s” perspective on the story.
I found all of those things in Laurie Polisky, who was introduced to me through another former colleague from my days at Patreon, podcast producer Emily Shaw. We connected right away and I actually ended up formally asking her to be part of the project before we even had a production or distribution deal. She took the risk with me.
Skye: Who else were you pitching at that point?
Simon: I went to Podcast Movement Evolutions in February of 2022 and I pitched people I met in the hallways, people I met in elevators. I was pitching anyone who made time for me. That was great because you can get a lot of subtle feedback from people’s reactions — when their eyes light up, that’s data that can inform you about what’s resonating with the listener and what’s not, how you might need to tweak things.
Skye: Tell me more about that.
Simon: I was very ambivalent about the degree to which my personal life would be a part of the story. Initially, I set out to tell Alana's story in a way that was sort of detached, where I wouldn't necessarily implicate myself. But as I was pitching, people were saying they wanted to understand my connection to the story — they were like, “we want to know more about you, because you are the one who’s alive to reflect on the themes of the show.” So it was through this process of pitching that it became clear to me that the story needed to be told in a way that was a slight departure from how I originally envisioned it. It was just a constant iteration, even as we started getting meetings with bigger entities.
Skye: What was the hardest thing about pitching all these various people and production companies?
Simon: There was so much that I wanted to get across, but I had to choose the most impactful things to say. You have to be really clear on like, the three main bullet points that this person needs to know. It was a lot of trial and error. My early pitches were very chronological, but it was taking too long, so I started jumping forward in the story and then going back a bit. It depended on someone’s time — I had a pitch for a situation where I had 30 seconds, and then I had pitches for hour-long meetings. You just start figuring it out.
Skye: Were you rejected?
Simon: I got many rejections. Sometimes it was just “your show doesn’t fit into our editorial vision for our upcoming slate of shows,” but other times it was more specific. One person told me that the story felt too depressing and would not reach a wide audience for that reason. I was like, okay, noted. I mean, that’s a very legitimate note.
Skye: I’m surprised you saw that as a legitimate note. Sad things happen in Alana’s story, but the show is about so much more than the sum of those things.
Simon: I guess what I mean by legitimate is that that person felt depressed by the story. I can’t argue with that. Their feelings are valid.
Skye: What else did you hear?
Simon: I was in a situation where someone suggested I pitch the story as a single episode of a larger show.
Skye: Did you consider that?
Simon: I didn’t, actually. I felt that Alana’s story needed the spaciousness of a number of episodes to be told in the right way. And there were enough other people saying that they also envisioned it as an entire show, that I felt my instincts were right about that. There were also people who didn’t move forward with me because their approach was focused on just monetization, and while that was certainly a factor for me, making a compelling story was much higher on my list.
Skye: When did things really start heating up?
Simon: We started getting serious interest from studios around April or May of 2022.
Skye: Can you talk some of the deal elements that came up in your discussions with these studios that didn’t appeal to you?
Simon: There were situations where I was offered a whole team of people to write the show for me, which felt really intimidating, especially as I was probably going to be mining a lot of personal material. I also had to think logistically about how I would build trust with a room full of people. So that didn’t end up being a fit, but it gave me insights into the mechanics of how a schedule works with some of these organizations. Other entities that didn’t feel right for the show were driven by a subscription or paywalled approach and as I’ve mentioned, I really wanted this to be accessible to a large audience.
Skye: How did you decide to work with Tenderfoot TV?
Simon: Tracy had seen some of the material I was developing along the way. She felt it was compelling and spoke about it with Tenderfoot’s CEO Donald Albright. Shortly after that, Donald called me directly to say that he hoped Tenderfoot would be included in the mix when I started figuring out who to work with. He was persistent and that ultimately made a real difference to me.
Skye: What was your first meeting with Donald like?
Simon: I could immediately tell that he trusted me as a storyteller. Part of that was our mutual connection to Tracy, but I also think he trusted my voice based on listening to the materials I had sent them. He got the importance of approaching the story from multiple dimensions — growing up as a teenager, or wrestling with one’s faith or sense of belonging. The team at Tenderfoot understood the show’s themes on a level where I actually didn't have to pitch that hard. Whereas in other cases, I felt like I was going to have to fight for my vision.
It was also clear that he understood the value of bringing Dear Alana to a wider audience. He recognized the show’s potential for bringing more diverse audiences to the medium as a whole, not just for Tenderfoot’s channel. It was a good sign to me that they were thinking about the show as a longer-term bet for the industry.
Tenderfoot’s small company size also felt very much in line with what I wanted [Tenderfoot TV tells me that they employ “about 20” people — SP]. I think my intuition that we didn’t need a big group of people to work on this show really panned out. Donald himself was intimately involved in the story editing and the marketing of the show. He was very hands-on. He, Laurie, and I would meet several times a week on Zoom and stay up really late talking through cuts. That’s basically how the show was made.
Skye: Did Tenderfoot’s reputation in the industry as a maker of true crime shows give you any pause during the decision-making process?
Simon: Initially, I was unsure of how the show would fit, given Tenderfoot's prior dominance in the true crime space. But the more I talked with Donald and Tracy, the more I could see that they trusted me to define the vision for the show, including its genre. Our alignment on doing absolutely everything the story required, along with their broad expertise in serialized storytelling, made me feel confident in my decision.
Skye: Do you own your IP?
Simon: I can’t talk about the terms of the deal but there were things that I had to make sacrifices on in order to gain the things that I felt were most important for the show. Unless you’re a mega celebrity, you're gonna have to make some trade-offs. It's about weighing what your objectives are for your show and deciding if they’re worth it.
Skye: Do you stand to make more money because the show is doing so well?
Simon: I do get a percentage of ad revenue but it’s too early to do that math.
Skye: How are you feeling about the level of response?
Simon: I’m almost in disbelief. The fact that it's reached people at this pace is incredible. I hoped people would find the show, but it’s spreading very quickly. I’m hearing from youth ministers, college students, school teachers, therapists, counselors, parents, clergy, former classmates of Alana's, LGBTQ folks, agnostics, atheists, nuns who've connected to the story and found it immensely cathartic and resonant. I've been most speechless after hearing from those who've been through similar experiences and never knew anyone else who could relate. They somehow found the show and felt seen in it. Those conversations have been really special.
That’s it for this week!
Next time: Donald Albright and Tracy Leeds Kaplan.
Postscript: Always read the credits!