Jessica DeFino is a freelance beauty journalist living in Los Angeles, California. For the past seven years Jessica has been writing, researching, editing, and publishing about the beauty and wellness industry. Her work has appeared in Vogue, The Cut, Fashionista.com, Cosmopolitan, Marie Claire, Business Insider, SELF, HelloGiggles, Harper's Bazaar, and more.

Before starting her career as a freelance journalist, Jessica worked as a beauty writer for The Zoe Report. She was Director of Communications at Fame and Partners, and worked as a ghostwriter for Khloé Kardashian and Kendall Jenner.

Jessica earned her bachelor’s degree in Music/Business Songwriting from the Berklee College of Music. Jessica’s music degree brings a unique perspective to her writing. It infuses each piece with lyrical qualities of storytelling, flow, and connection to her audience.

Jessica also publishes a bi-monthly beauty newsletter called The Unpublishable, where she shares “What the beauty industry won’t tell you — from a reporter on a mission to reform it.”

In this episode, you’ll learn about:

Making lasting connections with your audience
Why understanding music and rhythm makes your writing better
Capturing and keeping your readers’ attention right from the outset
The dangers of cross-posting your content across social media

Links & Resources

Jessica DeFino’s Links

Follow Jessica on Twitter
The Unpublishable
Jessica’s Instagram

Episode Transcript

[00:00:00] Jessica:
I started writing as a songwriter. The musicality of something is very important to me. So I’ll read my own stuff out loud sometimes. I feel when people can read something and there’s a clear flow and rhythm to it, and the words melt into each other sound nice next to each other, it locks them into the content early on. You want to keep reading because if you stop reading it’s like you’re breaking this rhythm that you’ve started.

[00:00:34] Nathan:
In this episode I talk to Jessica DeFino. She’s a journalist covering the beauty industry, but she tends to take an approach that’s not as popular with sponsors and publishers, because she’s anti a lot of their products and a lot of the nonsense that is put into the products and the marketing behind it.

She’s taking a critical angle and she’s well loved by her readers because of it, but maybe not so loved by the big brands. We talk about how that came about. We talk about her writing style, her approach of using her background in song writing and going to school for songwriting to have a better, more interesting writing style.

She gives some tips along that angle, talking about how she launched a newsletter last year and growing that to 9,000 subscribers. How that is a backbone for the rest of her work she does in journalism.

It’s a great conversation. So, let’s dive in.

Jessica, welcome to the show.

[00:01:28] Jessica:
Thank you so much for having me.

[00:01:29] Nathan:
We’ll jump around a whole bunch, but I want to start on the launching of your newsletter. What was the moment when you started to think, okay, I want to actually run a newsletter and start to control my own audience?

[00:01:44] Jessica:
I had been toying with the idea for a while, and then I think it was, April, 2020, right after the pandemic, where I had gotten into a situation where—I’m a freelance reporter—I had four freelance stories out when March happened, and Coronavirus lockdowns happened and everything was up in the air.

The company severed ties with all of their freelancers and basically gave these four unpublished stories back to me, and gave me a kill fee. So it was like I had reported out these whole stories. I had spent months on them, and now I had nowhere to put them, and I gave it about a month of pitching it out to other alums.

There weren’t any takers because media was in such a precarious position at the time. Finally I was like, maybe this is the opportunity I’ve been waiting for to launch a newsletter. and I decided to call it The Unpublishable because I couldn’t get anyone to publish this. And yeah, it’s been going, almost like every other week.

[00:02:50] Nathan:
Nice. Yeah. It’s interesting how these unfortunate moments result in something that’s like, okay, this is actually either a good thing now, or hopefully going to be a good thing soon, but it starts with difficult times.

[00:03:05] Jessica:
Yeah, exactly. I wanted these pieces to be big. They were stories that I thought were important to tell, and I really wanted them to be in a major outlet. Sometimes with media, you can’t sit on things for very long. It was like, I maybe have two more weeks before they stopped becoming relevant.

[00:03:23] Nathan:
Yeah. So for context, for anyone listening, what were some of those stories as an example?

[00:03:27] Jessica:
The first story I published with a piece called “Where are All the Brown Hands?” It was a look into the overwhelming whiteness of the top nailcare companies in beauty. If you would look at their Instagrams or if you would look at their websites, everything was modeled on white hands.

As a beauty reporter, when I have to source images for the stories, I don’t want to just be showing white hands. If I’m writing about nail trends or whatever, and it would take me hours every week to comb through places and try to find the trend I was speaking to on a person of color. At one point, I was like, why is this happening and how come it’s so hard?

This should not be hard. So, I wanted to do an investigation into it, and just like that the whole process had already taken six months. I was like, you don’t know what’s going to happen in this story. It might be scooped. It might be written by somebody else. It might be irrelevant in another month or so.

So, I really wanted to get that out there, and that started it.

[00:04:31] Nathan:
When you publish a story like that, and you’re used to publishing for a major beauty publication, but you’re publishing it for yourself. What did that look like? What was the process of saying, I have this story that I’ve worked on for a long time, and I have a brand new newsletter and all at once.

How did you bring that to life and pull the audience together?

[00:04:52] Jessica:
Well, luckily at that point I had a mask, a little bit of a social media following just from my work on work, like major publications. Like I had been writing for Vogue and allure. Harper’s bizarre. And I had been pretty diligent about building up a social media audience. So I had a pretty sizable, amount of readers just from Instagram.

And a couple of years prior, I had like tried starting my own beauty content platform, but I never really had the time to dedicate to it. But I had a small email list from that, from when I was still doing it. So I kind of like funneled all of that together under this new umbrella of this is going to be like my personal reporting newsletter and I kind of got the word out on Instagram.

So it ended up reaching like a surprisingly large audience for something that was like a first-time newsletter.

[00:05:44] Nathan:
Yeah. So if you don’t mind sharing how many subscribers were like to that first article?

[00:05:49] Jessica:
I think that first article probably went out to like 1500 subscribers

[00:05:53] Nathan:
Okay. Yeah, but that’s you’re right. That, that is a surprisingly of like, here’s the first thing that we’re doing.

And I guess it goes to show from right. Spending a whole career being known and, and building it in this space. And then, you know, you’re not starting from scratch when you funnel entity.

[00:06:10] Jessica:
Yeah, it, it had always been important to me to, not as important, but it was something I thought about to collect email addresses and to get social media followers, because my goal had always been to write a book. And I know that when publishers are looking at whether to buy a book from you, it matters what kind of audience you have and how many people you have on an email list.

So even though I wasn’t sending things out prior to finally launching the newsletter, Collecting emails here and there. Just, just to have for the, for the book pitch one day.

[00:06:42] Nathan:
Yes. That’s something that I’ve always heard is, you know, from agents and friends who are authors and all of that, as they talked about the, the email as being the thing that the publisher is looking for, they’re like, Yeah, that sounds good. First question.

[00:06:57] Jessica:
Yeah.

[00:06:57] Nathan:
I mean, they use it as a proxy for how many copies can you sell?

[00:07:01] Jessica:
Exactly. Yeah. When I was pitching out my book, it was all about, Instagram. I, this was probably like two years ago now. and I couldn’t get an agent to talk to me until I had 10,000 Instagram followers. So that’s like, all I cared about for maybe a year, I was like, I don’t care. I’m not going to put effort into anything else.

I just need these Instagram followers.

[00:07:23] Nathan:
Yeah. So you have 35,000 followers on Instagram now. what were the things that worked for you as far as growing that, that audience on it?

[00:07:32] Jessica:
Honestly, in the beginning, when I was like, I need to get to 10,000 followers, I was a little scammy about it. I did a lot of the like follow unfollow. So I followed a ton of people who were following accounts that were similar to mine.

And kind of, and what you do with that is like, they see that you followed them, they check out your page.

Hopefully they follow you back. If they don’t follow you back, you can like unfollow that person to keep your ratio looking good.

[00:08:00] Nathan:
So is that like going through and following like 50 people a day kind of thing or hundreds

[00:08:05] Jessica:
Yeah. I mean probably 50 to 200 people. Like I would spend probably an hour or two hours a day just doing. Stupid stuff like that, but I didn’t really care about, but I was like, I’ll do anything to get a book deal. If it’s following 200 people a day, that doesn’t bother me. And if at the end of the day, they’re looking at my profile and saying, Hey, this is somebody whose content I care about.

I’m going to follow them. It doesn’t feel like bad or wrong to me. So I just did a lot of that

[00:08:34] Nathan:
Yeah, it’s a very small way, like small and non-intrusive way to be like, Hey. Do you want to pay? Like, you’re just sort of raising your hand and people either go like no, or they go, oh yeah, I’ll look at that for a second.

What’s interesting is I think that a lot of creators started in that way, but probably now when they tell their story, they’re like, yeah. You know, I just, I just put out good content and then the content itself. And before you know it, I was, you know, internet famous, you know,

[00:09:01] Jessica:
I think that worked, it worked like 10 years ago, maybe even five years ago, but right now there’s just so much content out there on every platform. And I don’t think it’s fair to say that if you have great content, you will be successful on that alone. Like, I think you need more than that today.

[00:09:18] Nathan:
Yeah. So, so the following, people in the space, which we’d recommend, you know, regardless, what are some of the other things, on that quest to 10, that will.

[00:09:27] Jessica:
Yeah, I was falling up a storm.

I was liking a ton of stuff cause that’s kind of the same strategy. Like sometimes Instagram too will phrase your account. If you like too many things or you. follow too many people. So I was getting into that. I did a ton of hashtagging at the time. luckily the, the area that I write to to beauty has like a very big and dedicated community on Instagram.

So there are a ton of like beauty community hashtags out there that I was following and getting involved in and commenting and just really making my presence known in this community while at the same time posting my own content. That I thought had a very different point of view that would be intriguing to people.

So once they saw that I was engaged, they were like, who is this person? And there was, you know, a lot of content there for them to, to delve into.

[00:10:18] Nathan:
Yeah, that’s good. In the last, episode of this show, I had a YouTuber on his name’s Ali doll and he’s got, you know, he’s built up to 2 million subscribers on YouTube, but he talked about that like back catalog that you have of when someone comes across your work for the first time, like seeing the back catalog and seeing it have a unique point of view.

And I feel like. That would be the experience, you know, when you pop up in some little way. Okay. Another, you know, beauty, Instagram account, and then you come in like, oh, this is actually different. Has a unique point of view. So, I’d love for you to share. I don’t know what the, the short version of like the different perspective that you’re bringing to the beauty industry and what someone would notice when they come to your Instagram or your, newsletter.

And they’re like, this is different. This is a, you know,

[00:11:08] Jessica:
Yeah.

[00:11:09] Nathan:
Challenging.

[00:11:10] Jessica:
I think the easiest way to put it that most beauty content out there is very fluffy. and very positive and very product heavy. and my stance is very beauty industry critical. and I, I say that I’m pro skin anti product. So I’m much more interested in how beauty applies to like your actual skin and your actual body and like the human itself, rather than this external product, you can apply some very focused on the science of how human beings work rather than the science of like a skincare and.

[00:11:44] Nathan:
Right. Okay. Is there an example that comes to mind of something where you’re like, do this? Not that.

[00:11:50] Jessica:
Yeah. I mean, probably the biggest example is just, I mostly tell people to stop using skincare, you know, period. End of story. Just, you don’t have to, our skin does all of that for us. You know, humans have survived millennia without pre bottled products, and there’s no reason why. In the past 30 years, our skin has suddenly evolved to need a 10 step routine.

It doesn’t so, yeah, I just tell people, stop using it. And they’re shocked at the results all the time.

[00:12:20] Nathan:
I like that. I could see a conflict in. Message and business model in the industry. and your interaction in this. there’s a lot of money in the industry of obviously selling, I mean, any product, but especially a product that you need to buy every month or every three months or something like that.

Like that’s a very good business. So have you had any, any conflict of publications not wanting to pick up your stories or any of those things as the publication is. You tell your people to not buy our sponsor’s products, you know, or something like that.

[00:12:55] Jessica:
Oh yeah. I mean, there’s been a ton of pushback and depending on what platform I’m writing for, I. See my work being edited in a certain way or softened in a certain way or a brand name being taken out. I’ve had articles be published and then the platform takes them down almost immediately because an advertiser has complained.

I’ve had legal action threatened against me while I’m reporting for a story just for asking questions. yeah. Yeah. It’s that kind of stuff happens all the time because in beauty journalism, there is a huge. Conflict between what you’re supposed to be writing about and who’s footing the bill for that content, which is products and advertisers.

And I think in the beauty industry in particular, there’s this extreme lack of objectivity where, you know, editors and journalists and influencers are all gifted product or taken on press trips. And. And given money to review products in a way that in any other industry, you wouldn’t be able to call that journalism.

You know, there’s always gotta be some sort of separation there. Like a typical journalist is not allowed to accept gifts in the beauty industry. It’s the complete opposite. It’s like, well, how can you write about our product if we don’t gift it to you? So it’s, it’s a very weird space that is very reliant on gifts and money and advertising.

[00:14:18] Nathan:
So how has that changed as well as you’ve launched your own newsletter? I imagine you’re still doing plenty of freelance writing. Is that.

[00:14:27] Jessica:
Yeah. Yeah. I’m still, my, my thing is, is I try if I have a story I want to tell, I obviously want to tell it to the biggest platform possible. And then if I can’t get the story placed somewhere else, I will, I will tackle it for the news.

[00:14:43] Nathan:
Okay. So yeah. How has like, has the news that are helped? Like, for example, you’re trying to get us started placed and they’re like, sure, we’ll place it. But could we do this version of it instead? And, and you know, maybe you’re saying that like, no that’s okay. Whereas before the paycheck might’ve mattered more or how’s That. relationship?

[00:15:01] Jessica:
Yeah, that’s pretty much spot on. I, I didn’t really push back too much before, but now that I have. platform that like actually brings in, okay. Money for me. It’s not like if I say no, I don’t want that story published this way. It’s really not like I’m losing out on a paycheck anymore because I will make that up from my own subscribers.

So, I think since I’ve launched the newsletter, there have been two instances of that where I’ve written a story for a platform have been uncomfortable with the edits and actually. And was like, no, I don’t, I don’t want to publish it this way. And that feels really good to have a little bit more control over, over what I want to say and the information I want to put out there.

[00:15:45] Nathan:
Yeah. I mean, you have even more, I mean, you, you always had agency, right. But now it’s like, you have an alternative instead of like, I’ll keep pitching it to someone else who might have the same objections or, or that kind of thing. On the business side what’s well, actually, maybe if we dive into the newsletter today, right?

So that we talked about where I was at a year ago when we launched to, I just said, we, when you launched, I had nothing to do with my launch. There’s no Royal we in that are taking credit later. when you launched, you know, a year and a half ago, there was at 1500 subscribers. where’s it at today,

[00:16:24] Jessica:
I’m at 9,000 subscribers now.

[00:16:26] Nathan:
Right?

[00:16:28] Jessica:
But, I mean, I have a model where some of it is free and some of it is paid, so there are like different cohorts within the subscriber-based too. But like, I’m, I’m pretty happy with how it’s grown on the free side so far.

[00:16:41] Nathan:
Yeah. And so on the paid side, you’re charging $7 a month, or 77 a year. What was the thinking on the pricing there? Was that something that you like agonized over a lot or was that a, like, we’ll just go with something and see how it works.

[00:16:54] Jessica:
Yeah, I didn’t agonize over it too much. I started out at $5 a month and, after I got maybe my first hundred or 200 paid subscribers and I felt really good about like, wow, that feels like a lot. That’s like a good chunk of change I didn’t have before. And then when I was looking into the fees that were taken from like Stripe processing, from sub staff, I was taking home like closer to $3 per subscriber.

And I was like for the time and attention that I want to give this project, I’m just not going to be making it. At $5 a month until I hit a certain number of paid subscribers. so I decided to bump it up to seven, just to sort of motivate myself to put the time and attention into it that I wanted to give it because if I wasn’t going to be bringing in like, actually $5 to me, it didn’t feel worth it.

So by pricing it at seven, I get more like $5, which felt like a, okay, I’m happy with that number. now that I do have more paid subscribers, I am toying with the idea of, of lowering it because I feel like I feel like from, at least from my perspective, when I am subscribing to a newsletter,

I subscribe to a ton of them.

I’m much more interested to click. I’m much more likely to click pay and subscribe if it’s $5.

And if it’s like six or seven or eight,

[00:18:21] Nathan:
You think about

[00:18:22] Jessica:
Eh, that’s kind of a lot. Do I care enough about this content to pay that much? But personally for me, $5 is like a whatever I’ll I’ll subscribe kind of thing. So I, I think I’m getting closer to the point where I feel like I have enough of a base that I can do that and hopefully reach more people.

[00:18:42] Nathan:
Right. Okay. I have so many questions here, but diving into the psychology side of when you’re deciding to subscribe to something, right? Cause everyone listening is Ryan newsletter and asking these same questions. Like, should it be $5? Should it be $20? Should it be free? Shouldn’t be $2. You know, like any of these things.

And then they’re analyzing their own buying habits. And they’re like, but what if it’s a business versus a fitness versus, you know, any of these, like what category I’m in and what are those other things that you notice beyond price? When you as a newsletter consumer, I go to like instant subscribe versus like, well, think about this.

How many articles have I enjoyed from the recent layer? Like that, tips it over to the other side.

[00:19:25] Jessica:
Right. Oh, I don’t know that there are that, like my personal revelations will be. relevant to people. I personally, just because I run a newsletter, I love to support. So if it’s anything that I’m like vaguely interested in and it’s like $5 a month or less, I don’t know why $5 is my cutoff, but also subscribe.

And I’ll just see what it’s like for a couple of months. And if I don’t like it, Whatever I can always unsubscribe, but I just really love the idea of putting that abundance out there into the universe and just being like, I’m a little bit interested in this and I want to support this creator because I know what a, like a hustle it is.

I’m sure the average, like newsletter consumer doesn’t really doesn’t really think that way. but for me, I don’t know. I love a good headline if it’s like a good quippy, funny headline, like I want to be reading. fun, critical content. There’s a lot of like heavy, critical content out there. and I love something that’s like fun and critical, so that’ll get my

[00:20:27] Nathan:
Yeah. There are things wrong with the world and we could get depressed about them, but that doesn’t

[00:20:32] Jessica:
Yeah,

[00:20:34] Nathan:
About fixing the things that are wrong with the world,

[00:20:36] Jessica:
yeah, exactly. Like turn it into a little bit of a, like the state of the world I feel is so bizarre.

[00:20:43] Nathan:
Right.

[00:20:44] Jessica:
Just so wild that we have set up the world the way we’ve set it up. Like everything that, that exists is just something that like some guy made up one day and we were like, okay, we’re going to go along with it.

And I feel like there is a lot of humor in that. so yeah, I, I love looking at the depressing state of the world for like a bit of a jokey lens. So if I find anything like that, I’m like immediate.

[00:21:09] Nathan:
Yeah, that makes sense. And I think that’s where for anyone writing their content, like having that voice really matters. So it’s not just, you know, this is what you’re teaching or this is, the educational side. Or present the entertaining side. It’s like, okay. But how can you, how are you gonna make me feel as I read and consume this.

[00:21:29] Jessica:
That’s a great way to think about it. I think the difference, when I’m consuming like a newsletter versus the news is I don’t really know. I don’t concern myself with like tone or voice when I’m reading an article from like the New York times or the Washington post. but a newsletter is so much more personal.

It’s like you’re getting into people’s personal inbox, it’s more of a one-on-one relationship. and I think it’s a great opportunity to play with your voice in a way that you really sometimes can not when you’re writing for a media plan.

[00:22:04] Nathan:
Yeah. So what are the things that you’ve done to practice that obviously you’ve had a whole career as a writer. And so, you know, as you’ve found your voice and the things that you play with, are there yeah. Little exercises or things that you play with or try on, or anything like that? Any, any tips for someone who’s also looking to like craft their own way?

[00:22:26] Jessica:
It’s as much of a tip, but I started writing as a songwriter. I went to school for songwriting. So I feel like a lot of my writing takes that into account. Like that’s the musicality of something is very important to me. So I’ll like read my own stuff out loud. Sometimes like flow of a sentence is very important to me, the rhythm of a sentence, the like intonation, the, Continence and assonance and all of that alliteration, I, I feel like when people can read something and there’s a clear flow and rhythm to it, and the words like melt into each other sound nice next to each other.

I personally feel like it locks them into the content early on. Like you want to keep reading because if you stop reading, it’s like you’re breaking this rhythm that you’ve started. So, yeah, I would say rhythm is very important to me and reading things out loud helps me make sure that what I’ve written is what I’d like envisioned and felt

[00:23:35] Nathan:
Yeah.

[00:23:36] Jessica:
Mind and my heart when I was conceptualizing the thing.

[00:23:39] Nathan:
Yeah, reading out loud is a really good tip because there’s so many things where I’ll find myself starting to read what I wrote and then like finishing it in a much more like in my head in a much more conversational way, and then realizing the sentences or the following sentences that I had. We’re not conversational.

They were like stilted. The version that I wanted to auto finish in my head is like, oh, that’s better. Let’s let’s say that instead.

[00:24:05] Jessica:
I love that. And I think, I think newsletter subscribers are like ready for more. Conversational writing. Like I don’t, I think you can be like professional and say something that has weight and has merit and has value and still be kind of, you know, casual about it.

[00:24:23] Nathan:
Yeah.

[00:24:23] Jessica:
As a strategy to connect with people.

[00:24:26] Nathan:
Is there a poster or a piece that you’ve written that you felt like. Maybe you struggled to find that balance of like, it was a, maybe a weighty piece or something like that. And you’re like, oh, maybe this one I shouldn’t be playful with or, you know, finding

[00:24:41] Jessica:
Yeah, there are definitely times when I take a break from the jokey conversationality I think the last big piece that I wrote, was about, anti-Asian racism when like all the news came out that like anti-Asian hate crimes were at an all time high. there’s a lot of the beauty industry tends to take a lot of its concepts from Eastern culture, from Asian cultures.

So, there was a lot to say there about racism within the beauty industry that, you know, happens in ways that you may not even realize. So for a piece like that, I think there were some moments of, of humor within it, like a dark humor within it, but for the most part, for, for things like that, I take that very seriously.

I think my readers take that very seriously and I. It’s less conversational then, because it’s like, no, I have something that’s like very important and clear that I want to get through to you. And I don’t want it to be muddled with any sort of, uh jokingness.

[00:25:46] Nathan:
Yeah, that makes sense. So let’s say you were a writing coach, coaching someone,

Ryan newsletter, that sort of thing. You don’t have to become a writing coach after this. Just.

[00:25:59] Jessica:
Thank God.

[00:26:00] Nathan:
But like, you know, you have a friend, maybe they’re writing the newsletter, they’ve got a couple of thousand subscribers they’re getting going in.

And they’re saying like, you know, they, they hear what you’re talking about of the, the musicality and the, the flow of, of writing. And they’re like, okay. Short of going to songwriting school, like, what’s the, what, you know, is there, a book or another thing that you would recommend of where to start to, to sort of dive into the flow of what you write?

[00:26:29] Jessica:
There is a great essay, by Ursula K Le, is that how you say her last name?

[00:26:37] Nathan:
I’m not sure.

[00:26:37] Jessica:
Read it and I’ve never said it out loud before.

[00:26:41] Nathan:
Yep. I have so many things like that in my life where I’m like, I don’t know how to pronounce this word.

[00:26:46] Jessica:
It’s so embarrassing writing about skincare, because there are these huge, like long skincare ingredients that I write all the time. I can spell them for you off the top of my head, but then I tried to like say them out loud on a podcast, for example. And I’m like, I don’t know how to say this at all. I’m looking for this, this essay it’s from her book.

No, no time to spare

[00:27:10] Nathan:
Okay.

[00:27:10] Jessica:
And there’s this. And she writes a lot about right. but she has this beautiful essay about rhythm, and how it’s different in poetry and how it’s different in pros and how to kind of like sort out the rhythm of your piece. and I would say that was hugely helpful to me when I, when I first read it.

So I would recommend doing that and. Yeah, I don’t know. I use things like, I mean, I, I use it the sores all the time, but I use rhyme zone a lot for like fun phrasing and plays on words. It’s just rhyme zone.com and you type in the word that you’re you’re playing with. And it’ll kind of like, you know,

[00:27:50] Nathan:
Oh, interesting. Yeah.

That’s exactly the kind of, kind of that’s good. Yeah. A lot of people, you know, they come to newsletters from kind of two different sides, either from the journalist, professional writer side or the, you know, hobbyist, maybe even, I never thought I’d be a writer, but I have this skill or something to teach or behind the scenes in this industry.

And like writing maybe as a slog or a chore. And so it was always interesting when these two worlds meet and either, you know, one group might be really good at marketing because they knew they came from that world and another group.

[00:28:27] Jessica:
Yeah.

[00:28:27] Nathan:
Really good at writing and they each hate the other’s job, but

[00:28:31] Jessica:
Yeah,

[00:28:31] Nathan:
Like they pick the job.

That’s the intersection of both of those worlds.

[00:28:35] Jessica:
Yeah, no, you’re so right. I think there is this like sort of misconception in the journalism and reporting space that any reporter who is on sub stack has decided to go in all in on the newsletter. Because there have been some very high profile journalists who are no longer writing for like the times or the posts and they’re just doing their newsletter.

But I think for the large majority of, of reporters and journalists who have, who have started newsletters as well, it’s like a both and kind of thing.

[00:29:06] Nathan:
Yeah.

[00:29:06] Jessica:
Sill freelancing and we have this, this sort of personal platform.

[00:29:11] Nathan:
Yeah. So how do you think about your career developing over the next couple of years? Is it, is there a specific milestone in mind, where you’re trying to grow the newsletter to, to do that full-time or is it always trying to place a piece to the biggest possible audience?

What’s that like?

[00:29:29] Jessica:
Yeah, I would say my goal, like I very much, this is kind of earnest and nerdy, but like, I very much want to change the beauty industry. I see so much that is wrong with it and I see how it like emotionally impacts people. in terms of anxiety, depression, mental disorders, eating disorders, like there’s a lot of heavy stuff that comes out of the beauty industry.

And I like, I’m very passionate about actually measurably changing it. So for me, the number one thing is always, I want to reach the largest audience possible with an unadulterated message. So if I can do that in a place like the New York times, of course, I’d rather place it there than my own news. if I can do that through a book, of course, I’d rather write it in a book then in my own newsletter.

So the newsletter has been sort of like a nice foundation for me to have and a nice fallback for me to have. And I, I truly love fostering it as its own little separate entity, but I would, I would say I almost try harder to place things elsewhere because I want

As many people as possible to be able to, to read the things that I’m writing. the newsletter I’m I am writing my first book right now, and it’s definitely been hard to juggle book writing with like reporting for other platforms and deadlines. So I will say like juggling a book and my own personal newsletter has been much easier than trying to juggle a book and reporting. So I think, I think there will be times in my writing career while I’ll lean a little bit more heavily on the newsletter.

And times where I’ll lighten up on the newsletter. I’m always seeing it as sort of like a supplemental tool to my like greater mission.

[00:31:13] Nathan:
I think, I don’t know what publication they were writing for. but someone was telling me about, was that in each of these publications, they’re watching the view counts, you know, for every story. And they had gotten the newsletter. I think they were maybe at 20, 25,000 subscribers. And they would, when they placed a piece with a fairly major publication, they would email it out.

And they, it was enough direct traffic to that individual piece that they could get it to move on. Some of these internally watched leaderboards and stuff like that. And so editors were paying attention to that of like, they didn’t necessarily know like making things up that, you know, Jessica was the one who drove a bunch of traffic to this, but they’re just like, wow, Jessica’s stories are consistently resonating.

And so they were wanting to pick up more pieces in that. and so I was always wondering about that, of how you can, it’s not gaming an algorithm or anything like that.

[00:32:08] Jessica:
Hmm.

[00:32:08] Nathan:
Just saying like, look, here’s my story. And I bring an audiences.

[00:32:12] Jessica:
Oh, I love that. I might try to do that. I always do. Like I do these little roundups every other week for my paid subscribers.

And if I have something that comes out, I’ll always put, drop the link in there, but I’ve never done like a strategized push like

[00:32:28] Nathan:
Right.

[00:32:29] Jessica:
Be interesting to experiment for sure.

[00:32:31] Nathan:
Well, cause it’s like, if someone is following you that they’re following you for. Your content and your ideas and your perspective. And they probably don’t really care if it’s, you know, in your sub stack, you know, on your Instagram or, you know,

[00:32:48] Jessica:
Right.

[00:32:48] Nathan:
Major publication, there’s like, look, I want to read your, your content.

And you’re like, oh, today’s article is

[00:32:54] Jessica:
Yeah.

[00:32:55] Nathan:
Here on Vogue. Or, you know,

[00:32:57] Jessica:
Kind of nice to hear, because I think that’s something that I do worry about pretty often with my newsletter is I feel like a ton of my newsletter readership has come from social media. And so I’m like very conscious of cross posting. Like I don’t, I don’t want someone to get my newsletter and say, I already saw this on your Instagram, so I don’t need to subscribe.

I don’t need another email in my inbox because I’m seeing it on Insta, you know? And I don’t know if that’s like a legitimate concern or how much people see when they subscribe to you on different platforms. but that has been. You know, something that I’m very mindful of, where if it’s like a meme that I’m posting on social media, or just like a one-off Instagram post, I’m probably not going to repeat that content, even if I think it’s good or important on the newsletter. Just because I don’t know, I’m aware of like how precious it is to allow someone into your email inbox, because at least for me, like email is very annoying. The worst part of my day is trying to like go through my inbox and file it away into folders. And I never want my newsletter to be like, oh, I’ve seen this already. I’ve seen something very similar from her already.

[00:34:09] Nathan:
Right. Yeah. I don’t know that I have a perspective on that. I’m just thinking about it. I don’t have the same concern. but I don’t know that. You know whether I should or not. I think probably my approach would be that if you’ve already seen something, let’s say there’s five or six things in the newsletter and I’ve already seen one of them on Instagram, but I just skipped past that one.

[00:34:30] Jessica:
Yeah.

[00:34:31] Nathan:
And so my focus would be on making sure that everything is high quality, more than making sure that everything is, completely a unique

[00:34:40] Jessica:
Yeah. That’s I mean, that’s encouraging to hear, and I think that that might, change how I approach my like every other week

[00:34:49] Nathan:
Yeah,

[00:34:49] Jessica:
Maybe I’ll experiment and I’ll see, I’ll see if people are like, Hey,

I saw that.

[00:34:54] Nathan:
The other thing that I would do is I would ask, one of my favorite things to do is to ask for replies to my newsletter, which has a downside of that you get a whole bunch of emails, but they can often be really fun cause they’re, No, the people who are reading every day and like they’re following your stuff.

And, and so they’re usually not pitching you things. They’re just saying, like, here’s the thing that I, and so in that case, just say, Hey, you know, if I share something on Instagram, would you also like it here? Or do you feel like, keep those worlds more separate? Like don’t I want everything to be unique.

And then I would just like, say hit reply and let me know.

[00:35:34] Jessica:
Yeah.

[00:35:34] Nathan:
And it’s. Yeah, but you know, out of 9,000 subscribers, I’d bet you’d get at least, I dunno, 20, 30, 40 replies or something.

[00:35:42] Jessica:
Yeah, that’s a good point. Okay. Oh, you’re inspiring me. I have so many ideas now.

[00:35:48] Nathan:
Perfect. I love it. okay. One thing that I want to know more about is growing that. That newsletter from the pieces that you’re, I assume subscribers are coming from Instagram. And then also from the pieces that you’re publishing,

[00:36:04] Jessica:
Yeah.

[00:36:04] Nathan:
Seen like spikes? when it came from an Instagram post that did really well or some other promotion to drive subscribers,

[00:36:13] Jessica:
I mean, I definitely get new subscribers every time I post about it on Instagram or Instagram stories. So I would say that’s been like a main driver for me, but my two biggest, like surges of subscribers came from, All of the newsletter press that’s been happening lately. Cause you know, like the newsletter revolution is here.

So, I got a little write up in New York magazine and then one in the UK Sunday style magazine and both of those were amazing and totally unexpected. I had no idea they were coming. so now I’m like, damn, how do I, how do I facilitate some more press for myself? Because this is where that.

[00:36:55] Nathan:
Like what would a spike like that look like? Cause that a couple of hundred subscribers, 500 a thousand from one of those

[00:37:01] Jessica:
I would say from New York magazine, it was probably close to a thousand. And then from the UK, Sunday times was probably between like 500, 600.

[00:37:11] Nathan:
Yeah. That that’s substantial.

[00:37:14] Jessica:
Yeah. It was, it was really exciting. and it definitely goes to show like the power that these publications have. It’s interesting to see that power as applied to like inherently, anti large publication platform, like a personal newsletter, you know?

[00:37:35] Nathan:
Yeah. So how do you, how do you think about it when it’s like. More press would be nice. You’re like, Hey, this, this is a big boost, you know? I’d 10% lift in total subscribers or something from a single thing. And then knowing what you know about journalism and being in the space, like, is that something that you craft a strategy around and say, okay, I’m going to intentionally pursue, placements in these publication.

[00:38:02] Jessica:
No, in terms of just the newsletter, I, I don’t think I’ll ever like strategize and try to do that. I think, I mean, the, the reason that I got those two placements is just because I. In the beauty space, my newsletter does offer something that’s really different that you’re not getting anywhere else. and so it becomes inherently interesting to write about or call out because this is the only place you can get that kind of thing if that’s what you’re looking for.

So I think it’s just more of like striving to figure out, like, how can I create more, very original content that actually. Gives value to the reader in a way that’s going to create that kind of buzz. I don’t want to like manufacture the buzz so much as I want. Like my condoms would be good enough for people to actually talk about it.

But that being said, when my book comes out eventually like, hell yes, I plan to like strategize and try to get the shit written about me everywhere, which will hopefully we get to the newsletter as well. But yeah, I feel like I’m going to save all of that, like smarmy, you know, networking for book launch.

[00:39:14] Nathan:
Yeah, that makes sense to me. I want to push back on it a little bit, because so much of the success of the book is going to be dependent on a lot on a lot of things, but a big factor is going to be the size of your platform. When that book comes out.

[00:39:29] Jessica:
Yeah.

[00:39:29] Nathan:
And so if you wait to be self promotional until the book comes out, then like, that’ll get this far, but let’s say you were self promotional in a tasteful way.

We’re going to be tasteful about all of this. you know, but along the way, and that 9,000 subscribers turned into 25,000.

Right. And it’s that much bigger of a platform to launch from. So I’ll say that with the caveat that I think the same thing.

[00:39:51] Jessica:
Yeah.

[00:39:52] Nathan:
We have, I’ve lots of friends who have big platforms and I’m like, oh, I could guest post on them.

You know, with them, or like ask, Hey, can I come on your podcast or something like that? And I’m like 90% sure that they would say yes, but then I think, oh, I should save that for when my book comes out. Right.

Cause you know, you have that, maybe that, just that one ask.

So I think it’s something that a lot of creators struggle with of like when to promote.

And so intellectually I’m like promote early enough.

[00:40:21] Jessica:
Yeah.

[00:40:22] Nathan:
And then emotionally, what I’m actually doing is I think exactly what you’re doing, but I’ll save that for when I really need it.

[00:40:28] Jessica:
Yeah, I think for me, there’s also this, this sort of inherent struggle with what I write about and getting press, because I am pretty critical of beauty media coverage. and I’m aware that I have made some enemies in the beauty media space. Like I’m not the most well-liked person, in some of these circles.

So I do feel like I only have like a certain amount of rope that I can, use up like a certain amount of leeway in these spaces. and then also I, yeah, I don’t know. I think it’s something I have not sat down to really work out my feelings about. But there is some sort of ethical dilemma there where if I’m critiquing the way a certain platform has covered this beauty trend or whatever it is, I’m critiquing.

And then I’m sort of like asking for press at the same time, like ethically, what does that say about me and my participation in these systems?

You

[00:41:30] Nathan:
Right.

[00:41:31] Jessica:
Which is a big question and not one that I’m going to be able to answer here.

[00:41:36] Nathan:
Yeah. Are there publications outside of the beauty space that would have less of the, maybe sponsored ties or other, you know, issues

[00:41:47] Jessica:
Yeah,

[00:41:48] Nathan:
The main publications might have, but that would find your story.

[00:41:52] Jessica:
I think so. I think the path that I am trying to follow in beauty coverage right now. the path of sustainable fashion coverage, like I feel like fashion and beauty have been so intertwined in their coverage and they’re, they’re both sort of seen as these like less serious pursuits. They’re both seen as like inherently female interests.

And they’ve struggled to be taken seriously, I think. but with like the push towards sustainability content and, you know, the inevitability of climate change, I think. Sustainability and fashion is getting a ton of like serious quality coverage all over the place, even from platforms that wouldn’t normally touch fashion.

And I see beauty as being very behind that. Like there are still these huge global issues in the beauty industry and beauty production and just the way that we consume and beauty, that hasn’t been touched. But I see it starting to be touched by these larger, serious. News organizations. And I feel like there’s such an opportunity there.

And that those are topics that I’m super passionate about and super interested in. So I’m, I’m trying to carve out a space for myself there to say, look, we’re taking fashion seriously for the impact that it has culturally societaly environmentally. Like we have to start taking beauty justice seriously because it’s just as big of a person.

[00:43:17] Nathan:
I like, I like that angle on that. That makes a lot of sense. And just seeing trends in a neighboring industry. I think you’re right. I hope that I hope that you’re right in, that plays out in there.

[00:43:28] Jessica:
Me too.

[00:43:29] Nathan:
One of the things that I’m curious about is kind of the rise of newsletters in the journalism space.

I don’t come from that world. I very much come from the newsletter world. And so seeing, you know, so many people either make the switch full-time, or get to the point where they’re like, Hey, I’ve been writing these pieces everywhere. And like, my byline has just directed people back to Twitter or Instagram or.

And now it’s directing people back to my own audience. What are you seeing in like in your friends and colleagues and all of that is, are a lot of people starting newsletters or is there this overwhelming trend of some are starting it, and maybe it’s getting hyped more than is actually happening.

[00:44:12] Jessica:
Yeah, I think that’s what I’ve noticed. I don’t think as many people within my like, sort of direct. Community of journalists and reporters are starting newsletters. And I think it’s gotten so hyped. Like we’re in such a moment of coverage right now that it almost like, seems like a little lame to start a newsletter now.

Cause like everyone’s doing.

But the reality of the situation is that everyone is not doing it. And I think there’s still a lot of opportunity and a lot of room to grow and to move into and to create your own kind of thing. like I mentioned, I think there is a big misconception that if you’re starting your newsletter, that means you’re done with journalism and you’re just doing this now.

It’s like, no, you can very much do both. And you can do your newsletter once a month. You can do it, you know, once a week you can do it. However, often you have time for it. Like you said you could use it as a tool just to send out your journalism, pursuits to a wider audience. but yeah, I think sort of the hype around newsletters has sort of, created this little, Ooh, I don’t know if I want to do a newsletter too.

Cause I might get to see them. Like, I’m just doing what everybody else is doing.

[00:45:23] Nathan:
Right. Yeah. The, the newsletter hipster trend is sort of passed and it’s gone mainstream. I can’t do it

[00:45:31] Jessica:
Exactly. I mean, for the record, I don’t believe that that’s true, I think that’s how people are perceiving.

[00:45:38] Nathan:
Well, it’s so funny to me because, I’ve been doing E you know, email and email newsletters and that kind of thing since I guess, 2013. and you know, very excited. They got into all of that. And I was telling people like, email is amazing and friends that have me, who’ve been doing it since like 2001 were like, yeah, like good job, discovering it.

Do you want to go and start? Like what a pat on the back, what are you hoping for here? And watching is, you know, these trends as they come, if you had a friend who, you know, is in the space who comes to you and says like, oh, I’m going to start a new. You know, what are the things, I don’t know, the three or four things that you would tell them right away of here’s what they should watch out for is strategies that they should employ any of those things.

[00:46:25] Jessica:
I mean, my number one piece of advice that seems really obvious. Isn’t always is just to find your niche. Like I would say hone in on something as specific as you possibly can, within your space so that people have a reason to subscribe. I would say to have, like, especially if you’re doing sub stack or a place where you can view past newsletters, like have a healthy backlog before you actually start soliciting people to sign up so that they can see what your content is like.

And then this is a big thing that I think is missing from a lot of the journalism to newsletter side, because like he said, there are people who are coming from marketing and people who have never done marketing in their life. something that I do is that when I’m sending something out to my paid subscribers, I send a shorter version out of it to my free subscribers.

Click to continue. And then it brings them to the paid subscriber thing. And I convert between 30 and 50 people every time.

And when I sign up for free newsletters, which I sign up for a ton of them, I have never once got in that. I’ve never once gotten an email. That’s like the intro of the article. And then it, you know, sort of leads me into that paid funnel.

And I used to work in marketing. I used to work in fashion marketing. That was just like a no, duh of course I would do that sort of thing. but I’ve never seen any other like journalists to newsletter convert, use that very easy tool. so I would say, take advantage of that for sure.

[00:48:07] Nathan:
Yeah, that’s interesting of the things that in one industry, like you’re right in the marketing industry, everyone’s like, obviously, you know, of course you would do that. And then you get into another space and it is this exciting, new thing. I started in, in design and, like user experience and interface design.

And so I brought a lot of design ideas to marketing and then a lot of like direct response marketing ideas into the design world. And it needs to circle. Everyone was like, whoa, this is amazing and new.

[00:48:35] Jessica:
Yeah,

[00:48:36] Nathan:
You did it in the original circle, people are just like, obviously there’s nothing novel about it.

[00:48:41] Jessica:
Exactly. I think people really, underestimate. The skills they learn on the way to get to where they’ve, they’ve gotten to. Like, I never would have thought the job that I hated in fashion marketing would have served me in, in, any way. Cause I sort of wanted to get away from all of that. Like marketing bullshit, lack of a better word, because at least at the company that I was at, it mostly felt like lying and just like squeezing money out of people.

I think you can use those tools for good as well, which is what I’m trying to do.

[00:49:15] Nathan:
Yeah. So a lot of creators struggle with that transition where they feel like either from a past experience or something that they’ve seen where they’re like, oh, I can never ask for money for this or charge for it or, that kind of thing. Or they’re very, very hesitant to sell in any, anything. what would you say to them?

Or what’s your journey been like in saying like, no, this is what it costs. This is why you should subscribe.

[00:49:40] Jessica:
Yeah. I mean, I think it’s important to have, to have a reason, you know, make it very clear that it’s reader funded or user funded. for me, all of my content is very clear that I blame the media advertisement model for so much of the misinformation and bullshit that’s out there in beauty. So me saying that my newsletter and this content is completely user funded, so that I’m loyal to you.

The reader rather than an advertiser, is very like, you know, quote unquote on brand for me. And I think people who are interested in my content are more than happy to pay for it. It’s solving a problem that I am pointing out in my reporting, you know? and then I would just say also like allow yourself to be surprised at how much people want to support you.

I have been so pleasantly surprised by people who are just, they just liked my content and they’re happy to pay for it. And I think one of the, the biggest, the biggest ways that I’ve seen that happen is that, on substance. They let you do like the page, so you can do monthly or a yearly rate, or you can do something called a founding member, which is just somebody who pays a little bit more to support and they don’t really get any extra benefits at all.

And I am shocked at the amount of people who give me 50 more dollars than they need to, just to support, And that’s like, every time I get that email, that’s like someone signed up for the founding member level. It’s heartwarming because it’s like, there are a lot of people out there who want to support great creator, led content.

[00:51:23] Nathan:
Do you have a percentage or numbers on that? Like I’m curious, every time I see that I’m like how many people select that

[00:51:29] Jessica:
Yeah.

[00:51:29] Nathan:
Know from doing multiple prices or packages, that it’s one of the best ways to increase revenue is to just have a higher price option available.

[00:51:38] Jessica:
Yeah.

[00:51:38] Nathan:
confirming that, but I want to know any

[00:51:40] Jessica:
Yeah. I have not like crunched the numbers on anything, but just from, so I sent out a paid newsletter, on Thursday. So between Thursday and today from like my conversions of free

[00:51:55] Nathan:
Yep.

[00:51:56] Jessica:
Sign up, I’ve gotten, I think 56, new signups. I would say maybe 10 of them were the yearly membership and maybe five of them were the founding member.

[00:52:08] Nathan:
Okay. Wow. So half of the year, the ones being the like yeah. I’ll pay you $50 more just to support your work. Even

[00:52:17] Jessica:
Yeah,

[00:52:18] Nathan:
Because the yearly membership is supporting your work, but even just

[00:52:21] Jessica:
Yeah,

[00:52:21] Nathan:
Above and beyond.

[00:52:23] Jessica:
Yeah, exactly. I mean, that’s just what, roughly, from what I remember from the email. I’m not like super concerned with, with stats and strategizing right now. I’m just like ecstatic. Every time I get the ding on my phone that says somebody new signed up.

[00:52:39] Nathan:
Yeah. That’s super fun. So, what are the things that you’re thinking about next for the newsletter? Is it slow, steady, growth, and maintaining that while working on the book? Is there a big milestone that you’re working towards any of those things?

[00:52:52] Jessica:
There is not a huge milestone, but I think when I first started it, and this is, I think maybe just a personal hangup, but I was very conscious of not bothering people too much, like not being in their inbox constantly. So, it was like one big story a month, and then every other week for paid. Now I’m toying with the idea of doing more, short form content and where weekly content.

I’m going to be launching a new feature for paid subscribers that’s gonna be, like an advice column, but more like, how do I navigate the industry? How do I divest from these marketing tactics? How do I like stay smart and know what’s alive and what’s not?

So, I’m going to be launching that within the next month.

Then, for everybody, I’m going to be launching weekly or even twice a week, just like little, like a little tip newsletter. Because what I do in my newsletter a lot is critique the beauty, and point out what’s wrong with it.

People are always like, okay, sure, but how do I apply that to my own life? Like how do I get over the fact that I know it’s marketing, that I don’t need to have big lips to be beautiful, but how do I stop feeling that way?

So, it’s going to be more practical tips for, I guess, sort of healing from all of the beauty industry shit that they put us through, but it’s going to be very short, quick hits, like, you know, five sentences, a paragraph tops. So, I’m going to experiment with a couple of different, forms of writing and a couple of different frequencies and see, see what people.

[00:54:38] Nathan:
Yeah, that sounds good. Well, if anyone wants to go subscribe to that and follow you on Instagram and other things around the web, where should they go?

[00:54:46] Jessica:
My sub stack is JessicaDefino.substack.com, and you can sign up for The Unpublishable there. And then on Instagram, I’m @JessicaDeFino_.

[00:54:56] Nathan:
Sounds good. Well, thanks so much for coming on. This has been fun to

[00:54:59] Jessica:
Yeah.

[00:54:59] Nathan:
learn about a whole side of the newsletter industry that I’m less familiar with, and just hear your story, and your writing tips, and everything else.

[00:55:08] Jessica:
Yeah, thank you so much. I feel inspired. I’m going to go send more newsletters.

[00:55:13] Nathan:
Sounds good.

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