Alesandra Dubin is a freelance travel writer who has appeared in Good Housekeeping, Insider, Travel + Leisure, AFAR, Glamour, Esquire, and more. 

During the episode, Alesandra talks about the process for working on articles from various outlets, the benefit of pitching her evergreen stories, her HARO-alternative substack newsletter, and more. 

Follow her on Substack, Twitter, and LinkedIn.

Click below to listen to the full conversation and read below for highlights from the interview:

Effective Product Pitching 

[00:07:12]: BB: Good to know. Ooh, we have a listener question, Alice, that comes from Viviana Wiewall from Eventbrite. And Viviana has asked, what's the best pitch you've seen recently, and what about it captured your attention?

[00:07:28] AD: Okay, so I searched my inbox in preparation for our talk today, and I saw subject lines that I thought were sort of relevant to the discussion. It's not that any of these subject lines individually is an absolute winner every time. It's just more sort of thematically why they work.

[00:07:46] BB: Okay.

[00:07:46] AD: One of those, I guess, angles for a subject line is when you're pitching products, which, again, I do write a lot of commerce-driven stories, product roundup, gift guides, so forth. A lot of times, people are pitching things that are just in such crowded categories. It's like, I don't know, a lip gloss, a piece of carry-on luggage, something that there's just – a water bottle. It's really hard to differentiate in those categories. So I find that what works and what cuts through the clutter is if you can kind of position the product as a dupe, that is something that really sells a reader in a headline. So here are some examples.

[00:08:25] BB: Yeah, what do you mean?

[00:08:25] AD: Tell us the ultimate dupe travel destination to visit this season. So for an example that might be like, the dupe might be, oh, if you really want to visit the snowy Alps and have that sort of like european dreamy Christmas markets, whatever, here's the equivalent in the US for which you don't need a passport and it's cheaper. And blah, blah, blah. Get these high top sneaker dupes at this mass market retailer, okay?

[00:08:52] BB: Dupes are in.

[00:08:54] AD: Dupes are in; these skincare dupes that you need this summer are all under $15. So I think that basically readers love the sort of insider advantage of a headline that promises to help get this coveted.

[00:09:07] BB: That's the thing that they want at.

[00:09:09] AD: A cheaper price or more accessible way. Positioning as a dupe is kind of like a little bit of an insider angle. And then of course, editors love the engagement and the clicks and the revenue that, that reader enthusiasm, of course.

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Leverage Journalist Newsletters

[00:12:31] BB: Yes. Okay, good to demystify that. How can people build a relationship with you, Alice? Or frankly, do you even want to build a relationship with any publicists?

[00:12:41] AD: 100% I do.

[00:12:43] BB: Okay, tell us more.

[00:12:45] AD: As I said, it's just such a relationship driven business, and there are a zillion publicists out there. There are a zillion writers out there, but it's the ones that I know I can depend on that are responsive, that are smart, that follow through, that are giving me, connecting me with brands or experts that are really going to be useful to me and are worth knowing. That's what it's all about. And those are the ones that mind. Those are the ones that I remember. So I absolutely want to build those relationships and I also want to know that they're not transactional. So I love a quick little holiday note or a little. I saw on Instagram that your son is a championship soccer player or whatever. I just love one offs that suggest.

[00:13:25] BB: So you do like the little personal flair then, just like. So it's not like, here, cover this.

[00:13:30] AD: I do, and I like that. I mean, I like them to be sincere and you know the difference.

[00:13:34] BB: Yeah.

[00:13:35] AD: You know, the way that people can build relationships with me is really, it starts through my Substack. So I launched my Substack originally. Like, I think many other writers who launched Substack, it was as an alternative to HARO, really.

[00:13:52] BB: Yes.

[00:13:53] AD: Platforms which are so familiar and so filled with crap these days and they're so anonymous. You never know what you're getting, if it's plagiarism. 

[00:13:59] BB: It's the wild, wild west on that. Yeah. You don't know.

[00:14:05] AD: So this was a way for me to call for pitches in a way that felt more sort of like one on one. They're going to a more targeted list of publicists who signed up versus God knows what. And I'm receiving pitches from individuals rather than who knows what spam thought is behind those on HARO or whatever else. So I put all my calls for pitches there. I also put kind of like personal anecdotes, industry musings, and I do make it a bit of a personal. It's a space that, of course, is a professional space first and foremost. And my readers are almost entirely publicists. But it also shares a little insight about what's going on with me and contextualizes me in the world. So it definitely sets up to have a personal relationship with me if people want to respond in kind.

[00:14:57] BB: Okay, so personal flair and attention, Alice. Now building on that further, is it like, yeah, if you're in LA, invite me to a coffee smoothie, something beach walk? Do you do you even like that?

[00:15:13] AD: I guess, I don't know if my earlier comments implied that I might, but I actually don't really have a lot of bandwidth for in person stuff.

[00:15:21] BB: Oh, okay. Good to know. Don't see you in person.

[00:15:23] AD: Yeah, I prefer digital communication, communication by email. When it comes to professional relationships, often, if I'm doing sort of personal or one-on-ones, that's often like a function of my consulting business. So if it's like, let me pick your brain for an hour over coffee, I do not. My consulting arm, yeah. So that's part of my business.

[00:15:47] BB: No, in person. Good.

[00:15:49] AD: Of course, if it's an event that's relevant, an event or a press trip or some opportunity for FaceTime, other than just like, I want to pick someone telling me that they want to pick my brain.

[00:16:04] BB: No, I hate that.

[00:16:05] AD: What's in it for me? Because I do that. I charge for that usually.

[00:16:09] BB: By the way, who is using that phrase anymore? It is kind of the equivalent of moist in a professional setting.

[00:16:18] AD: It doesn't work.

[00:16:19] BB: Right. It's like, you help me, I don't have any context, but just like, let me just. Oh, God, no. I just had to put it out there, Alice.

[00:16:27] AD: Not at this point as a sort of senior level person doing what I'm doing. If I was junior and it was different and I was looking for friends in a new city or something, but just sort of at that point, at this point in my career and no, you don't need more busy personal life as a working mom. It doesn't really intrigue me, that kind of thing.

Rapid Fire Pitching Preferences

[00:17:11] BB: Alice, we have a quick, rapid fire question sheet here, so I'm going to fire these off to you.

[00:17:14] AD: Here we go.

[00:17:15] BB: Video or phone interview?

[00:17:17] AD: Oh, my gosh. Phone, please. In most cases, there's just no need for video. If there is a need, there's some kind of like product demonstration or something. Sure, but that's very rare. I can't even think of an example of that.

[00:17:29] BB: Bullet points or paragraphs in your pitches?

[00:17:31] AD: Bullet points.

[00:17:33] BB: Short or long pitches?

[00:17:34] AD: Oh, short.

[00:17:36] BB: How short?

[00:17:37] AD: Bullet points. Big bullet. Bullet points.

[00:17:39] BB: Three. Five?

[00:17:40] AD: Yes, three to five. Embed a logo's image, if relevant. So I can just get a glance and link to more information. Tell me there's information. If this founder is a unique woman of color founder story, I'd love to tell you. Maybe give me that heads up and then I can pursue it if I want more.

[00:18:04] AD: That's it. Email or Twitter? Dm?

[00:18:06] AD: Oh, I'm not on Twitter. Right. Yeah, I just can't.

[00:18:14] BB: By the way, what do you think is going to happen with that? Is it the next MySpace?

[00:18:21] AD: Know? I don't know what's going to happen with it. I actually have a bigger problem with it right now with social media, which is that I've been off and on. I've actually installed and uninstalled various social media apps on my phone since October 7th Hamas attack because of the spike in anti semitism that is all over, social media has become a very inhospitable place in a lot of ways, just a very anti semitism rampant. So when it becomes too much for me and I uninstall some of these apps, you will have no use reaching me that way. So I always prefer email or communication.

[00:19:03] BB: Good to know. One follow up or multiple?

[00:19:07] AD: I honestly think multiple is fine.

[00:19:09]: BB: Really?

[00:19:11] AD: I think it's fine. Just space them out and don't be aggressive with language.

[00:19:14] BB: Yes, direct or creative subject lines. You already hinted at this, but just to nail it. Yes, direct and then press release or media kit?

[00:19:24] AD: I'm going to say press release usually, but with a live link to photos.

[00:19:30] BB: Oh, okay. Live links. We like that.

[00:19:32] BB: What time do you usually read pitches?

[00:19:36] AD: Whenever.

[00:19:36] BB: Literally all the time.

[00:19:38] AD: I don't think there's like a right time of day or week. There's no magic bullet there. We're all working when we're working at various different times, different time zones, when we have insomnia and so forth. So I'll read it when I read it and I don't think there's any wrong time to send it.

[00:19:51] BB: Perfect. Any sources you're particularly looking for right now?

[00:19:56] AD: My deadlines are usually so swift moving that I don't think there'll be anything by the time this comes.

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