How a Food Editor Created a National Travel Media Platform with Amy Cavanaugh

Whitney Lee: Hey friends, welcome back. We have such an awesome interview for you today. I'm really excited to hear the story myself because I wanna know kind of what brought this all to be. So I wanna introduce you to our guest, Amy Cavanaugh is the editor at American Weekender.

Hey Amy, welcome to the show. Amy: Thanks for having me. Whitney Lee: Well, I like to kick these off and instead of reading your bio, I'm like, let's let them tell it themselves. I'm sure there's always, I love hearing people's of how, where they got to where they are today and how this came to be.

For everybody listening, I'll give you a little backstory. I stumbled upon American Weekender and obviously in the agency, we work so heavily in the hospitality space and I started reading the Substack every week and I was like, who is behind this? This is awesome. I should reach out to them.

So literally I'm hearing it for the first time as well. ⁓ So yeah, Amy, I wanna give you the floor and let you tell us a little bit about you and kind of how this whole American Weekender got started. Amy: Yeah, absolutely. So I have always worked in media.

I started my career in Washington, D.C., really kind of doing a mix of features, arts, food, travel, things like that. And then I moved to Chicago in 2010.

And once I got here, the city has an incredible food scene. So I really shifted my focus fully to food once I moved here. I've worked at a number of different publications around town, Time Out Chicago. Plate Magazine was a industry food magazine that recently folded and then I landed at Chicago Magazine in the fall of 2010.

I'm sorry the fall of 2019. So working at Chicago Magazine covering the city's food scene is my day job. But I've always, you know, done some freelance on the side written for places like Conde Nast Traveler, for Punch, for Eater, places like that. And then the pandemic happened.

And you know, we were sitting at home, my partner and I, Kenny, he and I are partners in life and business. And we felt the wanderlust that I think everyone kind of felt when we were trapped in our apartments for months on end. So we've always been avid travelers and both of us have always really enjoyed like getting in the car and going to small towns. We both love food and you know, we really felt as we traveled the country.

there is really great food everywhere. Big cities, small towns, college towns are a particular favorite of ours. So we really spent a couple of years, you know, kind of doing a lot of deep research on this. And we also realized that there was no travel publication focused exclusively on America and no publication that focused exclusively on American food.

And so we're like, all right, this is our way in, this is gonna be our thing. And so we created these field guides. as like the first step. And so that was where we began.

These digital downloads, you know, day by day itinerary to where to eat and drink in a city. And so we started there and then we were talking to a friend who works in media and he's like, these are great, but you need to get them to people. You need to get on people's radar. And he's like, what about a newsletter?

And this was kind of when Substack was taking off. This was, you know, 2022. and we had a couple of friends who had started their own newsletters and were publishing via Substack and we're like, all right, let's try this. So we launched our newsletter July, 2023, and we've been doing it ever since we published every single Friday.

We disseminate our field guides that way to our paid subscribers. You can also purchase them on our website, but every Friday we cover, you know, something from the road. We do big weekend getaway features that are everywhere we love to eat and drink in a place. We do overnight stays, which are just like quick hits, breakfast, lunch, dinner, and drinks, if you're in a place for a shorter period of time.

We do interviews with chefs and bartenders and other people who we think are notable in a food scene. And then we do other guides. We'll do a list of our favorite seafood checks in Maine or a guide to regional chili dogs or things like that. So we're really covering the breadth of American food through our trips and through the places that we really feel like say something about a place.

And we think everyone should know about them. Whitney Lee: I love it. So how do you guys pick a destination? it something that are obviously probably now people are finding you and pitching you.

But before were you guys just like these are our little bucket list stops? Amy: Yeah, so I'm from Massachusetts. I also lived in DC. Kenny is from outside Chicago, but he's also lived in Virginia and Indiana and California.

And so like we already have our places that we we really love and we go back to with some regularity. So we get out to New England, you know, quite a bit because I'm from there, but I also grew up going to Maine every summer. So we've done a lot of Maine coverage. We go out to California every couple of years or so.

So it's like we've done San Jose, San Francisco. We have a big wine country guide coming out soon. So we started kind of with the places that we really know well. And then being based in Chicago is incredible.

Being in the center of everything, there's so much within a driving radius. We regularly go to Michigan, to Wisconsin. We've been to Minnesota. We've been to Iowa and Indiana and so there's a lot that like we can get to like immediately surrounding us and Then we want to you know fill in the map with other places.

I mean Charleston, South Carolina is an eternal favorite of ours and so We love it so much and so we'll often go and then okay. Well, we're there We'll go down to Savannah or we'll go out to the islands and just kind of you know spreading ourselves as much as a rock Whitney Lee: Mm-hmm. Amy: Spreading ourselves around as much as we can. Whitney Lee: Yeah, we gotta get you further in the south.

I am from a college town in the south. So I'm like, and there's really good eats there. I understand why it's hard to stay thin in the south, you know? I grew up in Hattiesburg, Mississippi.

So for anybody listening, have you heard of Hattiesburg? ⁓ wow, okay. So I mean, Hattiesburg is not like one horse town. When I tell people I'm from Mississippi, people are like, Amy: Where are from?

Okay. I've heard of Hattiesburg, yep. Whitney Lee: Wow, did you have a red light in your city? And I'm like, okay.

It's not that, mean, the metro area is probably like 120,000 people, something like that, 100,000 people. But Southern Miss is there. So our claim to fame is Brett Favre was our quarterback and Jimmy Buffett went to Southern Miss. So, ⁓ and then of course Whitney Lee, know, add that to the list of stars that went to Southern Miss.

Amy: Okay. Yep. Whitney Lee: ⁓ But I love that you do the college town angle. ⁓ I think that that's always, you know, not just looking for fine dining, you know, I think it's like looking for the quirky stuff.

And I think a lot of college towns is where you find that probably. Amy: Absolutely, yeah. We have covered, actually, Oxford, Mississippi, where Ole Miss is, which we're huge fans of. ⁓ Charlottesville is another one.

Madison, Wisconsin. ⁓ I think that college town's just really like, you know, have often a very international population, so that kind of plays into it. You have people coming through, you know, fresh people every year starting school. Whitney Lee: Yeah, ⁓ yeah.

Just, yeah. Yeah. Amy: ⁓ who are exploring it for the first time. And so, you know, when we were recently in Bloomington, Indiana, and so we talked to some alums of Indiana University and we're like, all right, what were the places that you loved when you were going to school here?

And so many of them are still there. So you find like this longevity that really means a lot to people who spent some time there. So huge, huge fans. Whitney Lee: Yes.

I was just about to say the same thing. Yeah, I was about to say the same thing. It's like, have this, that is such a, if you had the traditional college experience, that's such a piece of your life that is like so memorable for a lot of people. So it's like, and the food is a big part of that.

So, okay, let's back up for a sec because I know a lot of PR people listen to this, so they 1,000 % know what substack is, but maybe for our hospitality people listening in, share a little bit about what substack is and kinda how that works. Amy: Yeah, so Substack is a newsletter platform and it has since evolved and now there's like a social component. It's kind of similar to like a Twitter or a threads. There's, you you can do video, you can do podcasts through that.

We really are using it, you know, to send out our newsletter and it is, you know, a super easy platform to use in terms of, you know, the technical aspects of it. But it really took off in the past few years. think really kind of, it predates the pandemic, but I think it really kind of took off around then where you build your own audience. And so you can charge for subscriptions.

I don't know if most people do or not, but we have a paid level and we have a free level where we send a mix of free and paid newsletters every month. So it's really, really taken off with a lot of... writers, especially in the food space, since that's what I'm so involved in, I'm seeing people join every day, honestly. And so there's Substack, there's also a few other competitors that have come up.

Beehive and Ghost are kind two of the big ones. But really the important thing about it is it's coming from the people, it's coming from us, it's a way for us to build our own audience, especially as social, the algorithms make it, you don't know. how many people you're gonna reach. And sometimes I feel like, you know, I'll post an important update on my Instagram and I'm like, hardly anyone saw this.

Whereas with, you know, our sub stack newsletter, I know exactly how many people are getting that every Friday when we send it. So it's really, you know, that ownership is such an important element. I think that's, you know, emerging in media today. Whitney Lee: Oh, for sure.

And we preach that to our clients too. We're like, if social media disappeared tomorrow, which obviously it's probably not going to, but I mean, think about it. They have ultimate control over such a valuable database, if you will, a following. They have so much control over that.

They could literally tomorrow flip a switch and say every post costs $5,000. Well, that would put Amy: Yeah. Whitney Lee: basically every business out of the game or every small business out of the game, a $5,000 post, they can't do that, you know, or whatever they could, you know, it could fold, could merge. There's so many things that could happen.

It's like email is really the only way to like truly own your community, you know? And we love Substack because I feel like it's a little more personal. Amy: Thank Mm-hmm. Whitney Lee: ⁓ That's just my two cents.

We follow a ton of these writers, journalists and stuff like that. And it feels like an actual note from them rather than like, you know, we get email blasts from companies and corporations through constant contact or MailChimp and things like that. But something about Substack feels more like a, almost like a diary or something like that, like a journal entry. And, you know, we're just receiving the journal entry.

Amy: different. I know, I think that, you know, has been really an important element of it is, you know, if you're getting our newsletter, you are getting our take on everywhere we've been. And you know we've been to all the places you're right about, because that's our thing is like, you know, sometimes I'll read stuff and I'm like, I know you didn't go to everything, but like, you know, we really want it to be, we went, we had this, this is what we love, this is what you should got and here's where you should go.

And I think that, you know, it really is coming through in this newsletter format. Whitney Lee: For sure, I think the biggest question for a lot of people that, number one, I even thought to myself, how did I discover American Weekender? ⁓ That's the hardest part of growing a platform like this, right? Because on social, like you said, you're kind of.

If you're trying to go organic, good freaking luck. You know what I mean? Like the algorithm has got you by the throat. Good luck trying to grow organically.

You can put money behind it, which does help. ⁓ But with Substack, like what was your strategy on people discovering it? Amy: Mm-hmm. Yeah, honestly, that is the hard part, discoverability.

like, you know, we know there are more potential readers out there who are interested in what we're doing for sure. ⁓ And so, you know, every newsletter we do post on all the various social platforms. We have Instagram, we have Facebook, I post on LinkedIn, et cetera. And, you know, with each newsletter we do, we have the potential to reach a new audience.

So our latest field guide was for Knoxville, Tennessee. And so, you know, we covered a ton of places that we love there. And so whenever we're doing that, it's like, okay, now if we can get them to share, whether it's, you know, visit Knoxville or the wonderful restaurants we went there, that introduces us to a whole new audience. And so every interview we do and every, you know, place we cover the newsletters has potential to just reach a new audience and a new geography of people, which I think is important.

Whitney Lee: I love it. And also, you know, thinking about the places that you select and I mean, are they reaching out to you or are you reaching out to them when you pick a city? Amy: It's been a mix. We definitely have this whole list of folks who have reached out and we're like, ⁓ my God, if only we can travel full time, this would just be incredible.

⁓ So what we do a lot is we actually will like stack locations. We will be like, all right, you know, last summer we went to California, we're going to San Jose, we're going to San Francisco, then we're going up to Napa and Sonoma. One flight, we were able to, you know, really kind of bank a lot of good coverage for that. ⁓ This spring we hit the road, we went to Knoxville, Lexington, Kentucky, Bloomington, Indiana and Indianapolis.

And so we're rolling out a coverage from that. So because, you know, my partner and I both have full-time jobs, that has been a way that we've been able to really kind of like maximize our time. So, you know, as we're looking at potential trips coming up, you know, two kind of areas we're eyeing are, I'd love to get out to St. Louis and Kansas City.

I'm like, all right, we could do... both of those trips, you know, hit them both together, stop in Springfield, Illinois, along the way, pick up, you know, different places there. And then we want to do the Gulf Coast, you know, so we wanted that is very high on our list. So we're like, all right, how many different places along the coast, you know, could we hit on one trip?

So that's definitely been a way that we've been we've been doing it. And yeah, we have so many folks, you know, different, you know, PR. groups that have reached out that were like, ⁓ my God, we're dying to work with you. And if only we just had more time to be on the road constantly.

Whitney Lee: ⁓ if only you knew a PR person who started her business, Dustin, Florida, and might know some connections on the Gulf coast. mean, wouldn't that be interesting? No, could, we could totally. And actually they're, they're getting ready to go into their peak peak season.

So we should revisit that for post madness. You need to be there when it's not gangbusters a million people to like really get into it. But, ⁓ yeah, cause I was about to say on Substack, you Amy: Yeah. Thank That would be perfect.

Yeah. Whitney Lee: We use a lot of subtexts of hearing what journalists want to write about, you know, ⁓ and for us as a PR agency, I think it, it, I love being able to provide them and like actually be truly helpful to them where somebody's like, Hey, I'm writing a story on spicy cocktails. And we're like, ⁓ man, we have the ghosted with a popsicle, spicy popsicle sticking out of the top and a little, you know, and actually being like a resource rather than sometimes in pitching.

We, mean, we'll, Amy: in this. Mm-hmm. Whitney Lee: will cold pitch, hey, we dropped a new menu or this is coming up or it's this kind of month and we're doing something special for that. ⁓ But sometimes it can feel like we're being a nuisance, you know?

⁓ So I love a warm lead, you know, where we read she's looking for a spicy cocktail and we got exactly what she needs. We may not get the coverage. Maybe she gets 600 other spicy cocktails in her inbox, you know, but we try to explain to our clients, know, ads are what you pay for PR is what you pray for. You know, it's, it's not guaranteed.

um, one thing I would love to chat about too, in general in the hospitality space is Amy: Yep. Whitney Lee: educating our clients on what the difference is in hosting someone like you versus hosting an influencer. Because now, I feel like the lines are getting, not on our half, but on the client's half, the lines are getting so blurred on what to expect. when you drop into somewhere or they wanna host you, kinda tell me how you negotiate that and what...

⁓ I don't want to say what promises are made, but what does the relationship look like when someone's like, hey, we want to host you at ABC Diner? Amy: Yeah, it and I totally understand like where confusion comes from because media has just been changing so much so quickly that it's like kind of hard to know what everyone does and you know, everyone's role is within within the industry. ⁓ So we typically look for assistance with hotels. So when we, you know, go out to Portland, Oregon, the thing that we need most is hotel assistance.

And so we really have retained our itinerary. Food is our passion. so anytime I'm going somewhere, I'm like, all right, I have a list of 25 restaurants I want to go to. Here's what I'll often say to the publicist.

Here's what I mapped out. What do you think? Have I missed something that really speaks to your food scene? Are there any recommendations that are kind of the hot new thing that just hasn't crossed my radar yet?

And that's how we'll often find things that are like, you definitely, this new bakery is incredible. You have to go. And that's how we found this wonderful bakery in Buffalo, New York of just the publicist checked my itinerary. She's like, this looks great, but you gotta go to Butter Block.

So was like, okay. And so we really, you know, we certainly don't promise coverage. However, if we're taking a trip somewhere, we have to do it. We don't have the time to, you know, be like, well, we took this trip, there's nothing.

There's always something with our perspective and how we do it is that, you know, we know that there's good food everywhere. We know that any place we're going is a place that our readers would be interested in traveling because our readers are, you know, very interested in domestic travel. If they're not going on vacations, maybe they're going for work or for a wedding or something. And so we're always trying to point people to what the best places are.

And so the best way we do that is We come in, we eat and drink at as many places as we possibly can, and then we pick our favorites and write about them. Sometimes everything is a slam dunk. It absolutely has happened a lot where we go on a trip and we're like, everything has been fantastic. We include every place we go.

And other times we're like, ⁓ some of these, you know, maybe quite aren't up to our standards and so we won't include them in our piece. ⁓ yeah, we really, you know, for working with us, assistance with hotels is the big thing. And then, you we've worked with some other local visitors bureaus who've assisted with Uber codes and things like that, which also really makes our job easier too. So ⁓ I know that influencers or other journalists work different ways as well.

And I've done ⁓ more traditional press trips with my day job now and with the way we kind of work at American Weekender. Like a classic press trip doesn't work super well for me. ⁓ But we've been lucky to be able to work with some wonderful PR folks who've been able to assist us in other ways. Whitney Lee: And I've noticed in general, world of like, fans and press trips is also changing because I just feel like everything is so much more casual now.

You know, it used to be so buttoned up of like, here's the itinerary, everyone must be in attendance. And now like most of the fans or press trips that we host are so casual. We like let people go at their leisure. We don't force, like if we're doing a fam, we don't force everybody to eat together.

It's like, I want you to experience it the same way a guest would experience it. Amy: Yep. Whitney Lee: driving to sit across the table and have small talk. Not everybody's a PR person.

I enjoy that, right? I'm pretty extroverted depending on what side of the bed I woke up on that morning, but I'm pretty extroverted, but I can understand that some people, that's like not the best way for them to experience a property or a restaurant. It's like forcing this fam environment where you all sit at the table together and have this uncomfortable small talk, you know? Amy: Mm-hmm.

Yeah, I think that, you know, that acknowledgement that everyone works in different ways. Everyone needs, you know, different things from a trip to, you know, be like, no one is really able to take a trip like purely for fun. Everyone's got to go and get at least a story or two out of it. So like really finding the ways to like ensure that everyone really gets what they need, I think is so important.

I mean, but I've also made friends on, you know, some press trips I've done in the past that I've, you know, still stayed in contact with, which has been great. But Whitney Lee: Yeah. Amy: Yeah, I kind of like the more casual nature of like, all right, this person needs this, this person needs this, you know, to make sure that everyone really gets what they need. Whitney Lee: Yeah, as long as they hit the restaurant, they hit this, they hit that, I don't care when they do it on their trip, you know, and letting them kind of enjoy it at their leisure.

Okay, so I have a question. pick a place, ⁓ let's say you're going to a city and you've decided I want to go to this ⁓ do you let them know you're coming or do you just drop in? Amy: can ⁓ Sometimes we do and sometimes we, you know, if we have a contact in a particular place and be like, hey, you know, we're coming in. ⁓ Do have any recommendations?

Could you provide any hotel assistance? We don't always, though, ⁓ just for, you know, ease of trip. Sometimes if like we are here for a very brief time, we need to, you know, kind of get in and get out. ⁓ But.

We've also had some folks reach out from the road, which I really applaud, where we were in Lexington and we're like, all right, we're here for one night. I posted one photo on social and then I got a whole list from Lexington's PR the next morning. It's like, hey, we saw you're in town. Here are some of our favorite places.

If you have time to go to them, great. If not, let us know next time. And I was like, that was excellent. like really like monitor, saw like one random photo that I posted and were on the wall.

Whitney Lee: when go into a restaurant, will you sometimes go eat and cover them and not ever even tell them and just post it? Amy: Yeah. Whitney Lee: Okay, I love that. ⁓ We've been working with, we have a client in Fort Lauderdale and ⁓ they have a publication down there, or a media outlet I would say, ⁓ called Infatuation.

And ⁓ his rule of thumb, and mad props to this guy, name's Ryan, I don't know him personally. ⁓ Amy: ⁓ yeah. Whitney Lee: They do not accept any hosted meals. They will never tell you they're coming or anything.

They like actually want to be undercover because they want to experience it just like everyone else does. ⁓ So I mean, I've tried to reach out and obviously I'm like, I respect how you work. I'm not trying to like pitch you on anything, but just FYI, this new restaurant's coming to town. But I mean, we love that.

We love the opportunity to work with somebody, but also if you You want to just come in and like, we're always going to be excited to see the press coverage, you know, to be like, ⁓ we had a writer that popped in, you know? But it also teaches a lot of these places of like, you never know who you're serving, right? Amy: Mm-hmm. Yeah.

Yes. Whitney Lee: ⁓ And so it's like being on top of your game all the time because the editor of a publication, food writer, a whatever could be dropping into your doorstep and going to write something on you ⁓ and you don't even know who you're serving. Amy: Yeah, absolutely. mean, in Chicago, I'm very much a known quantity since I've been covering food here for a long time.

But, you know, when I'm traveling, we'll go to some meals and, you know, immediately get a little something. like, ⁓ someone looked at their restaurant book. So someone looked at their reservation book and kind of looked us up and saw what we do. ⁓ You know, which is always, you know, you've put that forth out.

You see that a lot in more like fine dining restaurants and things. But. Whitney Lee: Yeah. Yeah.

Amy: Yeah, I mean, we love also, you know, finding those places that maybe we're, we'll just stop in for a drink and, know, before dinner or something. And it winds up being our favorite thing of the whole trip. Like I think for us, like that really just like casual, oh, let's swing by and see can turn into actually we're going to have dinner here because this is great. Like we went to San Jose last summer and our favorite place wound up being this wine bar where we were like, oh, let's just, you know, go have a drink before our dinner reservation.

And then like, oh, the food looks excellent. So then we got like a couple of plates and I'm like, oh man, this is really good. We went back the next night to just try more things and it wound of being like the real highlight of our trip, even though it was like originally on our list of just to, let's just pop by for a glass of wine and then see. And then we did a whole story of them.

Whitney Lee: Don't you love a stumble in? I actually, so I had never been to New York City, which is ridiculous, until last year, 2020, what, yeah, 2025 was the first time I had ever been in New York City. I have been around the world and never made it to New York City, which is ridiculous, but everybody, when I planned the trip, everybody's like, ⁓ my God, you have to have all your reservations mapped out because New York is like so crowded and so stuffy and you won't get into anywhere and you'll never get a reservation and you'll, you have to get a reservation and have, Amy: Yeah.

Whitney Lee: everything mapped out before you went. So I did a little bit of that, but I also allowed. I was there for a whole week. I allowed myself to just drop in and I ended up loving the drop-ins, just wandering into somewhere that I was like, that place looks cool, and just wandering in and sitting down.

So I went back this year. I was speaking at New York Restaurant Week, or Restaurant Show, and I was like, I'm not gonna make a single reservation. I'm just gonna wing it, you know? And ended up having, well, and when you're flying.

Amy: Mm-hmm. This Whitney Lee: solo it's really easy to just like slide into the bar that's like totally my style ⁓ but those end up being the hidden gems sometimes Amy: Mm-hmm. They really do. mean, so we put together a very intense itinerary with, you know, we make it in our reservations that are like at our top spot.

So like, we know we can get into them, but we are also super flexible. So if we were really, we're constantly like looking at our itinerary, reassessing, moving things around, prioritizing stuff, you know, based on. this bartender like this and our server recommended this place. And so we're in real time changing things.

So we really go in with like this solid framework, but are very open to just, all right, everyone told us we have to go to dinner here. We heard that this other place was maybe not quite as good as it used to be. Let's completely change our plans and have dinner there instead. So we do that all the time.

And I think like that flexibility is really key. It's like, there's so many places that we find out about once we're in a destination that never came up in any of our research. And so it's like, think being open to changing your plans is where you'll find the best things. Whitney Lee: 1000 % and I always say ask the servers because the servers they know the food scene I was a server a bartender for all of college and grad school and all that and I always ask the server what's your favorite things on the menu or what is everybody's favorite thing on the menu and what else in town where else do I should I stumble into you know and I feel like that's where you find the real story you know Amy: I know.

It's me. Absolutely. Yeah, we try and go to what we think is going to be the best cocktail bar in town. Cocktails are a big part of our coverage at American Weekender.

So we're like, all right, what's the best place? We're to start there and say, who else do you think is doing cocktails at your level? And we'll often hear things that hadn't come up or we'll hear that, like, actually, this other place was great, but they just, you know, the whole staff turned over or something and like, all right, we can cross that off the list and then, you know, try these new recommendations. So really tap the people.

Whitney Lee: Yeah. Amy: who live there when you're traveling is such a good tip. Whitney Lee: Yeah, and a lot of the local small town mom and pops, like they have no knowledge of SEO. They have no knowledge of websites.

They have no knowledge about, and they can't afford an agency. And so they, they are literally fully driven off of stumble in or personal recommendation. ⁓ and also if I can get a little geeky for a hot second, the amount of our clients that use pop websites, they're like, but it's free with our, with our POS system. We get a free website.

Amy: Yeah. Whitney Lee: And I'm like, yeah, but Newsflash, that free website, you are now invisible to Google. Like, it's literally a placeholder. Like, no one is going to be able to search and find you with a pop website.

invest, I mean, heck, now AI can build your website for you in like 10 seconds, but you know, the times they are a-changing for sure. ⁓ How do you manage if you have a really, okay, like let's say you negotiated, ⁓ for someone to treat you and you're gonna come in and experience the restaurant or the hotel or whatever and you have a really negative experience. How do you handle that if they feel like they're, they feel like they're guaranteed coverage but the guaranteed coverage they're gonna get isn't gonna be the best reflection, you know?

Amy: I mean, thankfully that is not something I have had to experience very often, which is great. But I feel like when we've worked with like publicists, you know, to assist with like hotel accommodations. We've really worked with publicists who understand us and how we work and what's important to us. And they really point us to the place that seems to make the most sense for us.

So when we went to Portland last summer and we worked with VisitPort or Travel Portland and they're like, what hotels in town sounds good? And they were like, these are some that we recommend. we were like, well, really kind of the most important thing for us is these all sound great, but like, geography, where can we walk to restaurants, where can we walk to bars? And they kind of helped us find like, this is going to be the one that's right for you.

So thankfully, we have not had to deal with that. I am sure that, you know, folks who've done more, you know, more hosted trips and things than us have had to deal with that. ⁓ But as with all things, I think communication is very key. You know, really being kind of upfront about like what you do, what you're what you're helping to get out of the trip, I think is huge.

And so, you know, with us, it's like if we're coming somewhere, we want to get, you know, a field guide, which is our, you know, digital downloadable guides. We want to get at least a couple of newsletters. We want to get, you know, a weekend getaway with hear all the things that we loved in a place. We're also looking for, you know, could we do a feature on what your signature local dishes, you know, whatever that may be, whether it's, you know, the Delta tamales in the Mississippi Delta or something like that, like we want to find out what is the stuff we should be covering.

And so once we're there, we're making sure to hit all those places. And we really, I think we've really kind of gotten across what we covered so far, but we love the lowbrow, we love your taco joints, we love your burger trucks, we love hot dogs. And we go to fine dining and tasty menus. We really like span the gamut.

And we also love, you know, newer places. Like what are kind of the places that are getting the buzz, getting the attention? And then your hundred year old plus restaurants. What are, what are like the signature like classics that like make a place a place?

And so I think, you know, being upfront about like, this is the kind of experience we're looking to have. And here's what we're hoping to get out of it is the best way to like upfront approach. this is what it's going be and here are some ways that maybe we could work together on that. Whitney Lee: Definitely, and I've been so grateful because the media and some of the influencers that we worked with, they've given us the opportunity before they have a negative experience or before anything goes awry of shooting us a message and being like, hey, I was expecting this and this isn't really happening, rather than, some of the writers these days are, back in the day were savage.

It was like, Amy: Mm-hmm. Whitney Lee: sorry, you missed it, I'm gonna write 100 % everything that happened. And I think that's like people's fear, but thankfully we've had such good relationships that, know, for me it's more working with the writer and the media is the easy part, right? Like we know how this works and we can make it happen overnight.

It's the client and the hotel's expectations and the restaurant's expectations, you know, of teaching them, especially now influencers like, Amy: Mm-hmm. Whitney Lee: we were talking about, influencers are so common. And we negotiate that of you get this and we get this. You know, we give you a $250 tab.

You are going to post a real five stories. have to tag us, location tags, blah, blah, blah. ⁓ And our clients can grab their heads around like that confirmed deliverable. But with a media guest, like they don't, it's hard for them to understand.

like, you're gonna tell me that we're gonna put them up all weekend and they may or may not even write about us. Amy: Mm-hmm. Whitney Lee: And I'm like, yeah, that's how it works. Even with awards, we had a client that was up for a really big top tier publications award.

And they had to come for the weekend and experience the property to make sure everything we found in the application was true and all that. And we didn't end up getting the award. And the client just crucified us over that. And I was like, this is how it works.

Amy: Mm-hmm. Okay. Is that? Whitney Lee: This is what I told you from the get-go.

is nothing is guaranteed. PR is what you pray for, you know? But now this world of influencer and new media has really evolved everybody's expectations, I think. So.

Amy: Yeah, that's super interesting to, you know, just kind of think about how it's all changing like so, so, so fast and just, you know, knowing everyone's, you know, what everyone kind of brings to the table is is so interesting. Whitney Lee: You know what I love is that I'm speaking with a real human right now because in our space, people are getting eliminated from their jobs left and right. You know, we had a client that said, how do you guys work in a city where you don't live?

And I'm like, well, because we, most of the writers in the media that we deal with don't live in your city either. You know, like everything has become so centralized or people are losing jobs left and right and, and that kind of thing that finding Amy: Right. Whitney Lee: I'm just really grateful for the real human relationships that we still have because everything, feel like everyone's becoming freelance, everyone is shifting and you know, a PR person's value used to be who do you know and what writers do you know and now I'm like, good luck if that's what you're hanging your hat on.

Because writers are changing, writers are, you know, like everything is evolving so much that your Rolodex, you know, and your local connections doesn't get you what it used to get you, you know? Amy: Yeah, it's definitely, mean, so many times I'm looking for a contact for someone, I'm like, I don't think they're there anymore. seeing it in all aspects of this world of just, yes, I've seen more and more people kind of going off on their own and doing their own freelance and things like that.

Yeah. Whitney Lee: Well, and it used to be like we could pitch a story to a writer and think, I say like Sex and the City style, like Carrie, remember when Carrie would go into her editor and be like, hey, I have an idea for a story, here's the angle. Women who date, men that pick their nose or whatever, know, like whatever her story angle was. And ⁓ she had to convince the editor, like, this is a good idea, this is relevant, women want to read about this.

And the editor would say yes or no. Amy: Yeah. Whitney Lee: I try to teach our clients now that that game is basically almost over now. It's like a lot of the publications we deal with are like, hey, we did a Google search and here's what people are, or we're looking at the search keyword terms.

People are all searching about Bolly right now, so guess what, Amy, you're writing about Bolly. Amy: Mm-hmm. Whitney Lee: go write a story about Bali because that's what the Google search is saying. And it's all about web traffic now is determining the editorial.

I feel like the editorial calendar has just gone out the window. I don't know. From your perspective, I'd be interested to hear that. Amy: Mm-hmm.

Yeah, I feel like I'm in a very lucky position with ⁓ both my full-time job and American Weekender. When I was at Time Out Chicago, I got a list every week of like, here's your SEO terms for the week. it'd like, best French restaurants, best burger joints, whatever. And I had to like beat my quota of like SEO geared stories, which was...

Very draining. yeah, ⁓ you know, at Chicago Magazine, I really have the freedom to be like, these are the places that I think are cool right now. And these are the places that like, you know, I think are great or my writers think are great or, you know, even if it's a less than positive review, a place that we should be covering. And so it's very similar, you know, with American Weekender, we're really like allowed to just follow what we're interested in.

And we know that readers are too. Like, you know, it's... Every time we publish a new ⁓ piece, whether it's a list of our top burgers or something like that, but I always get responses from people of just like, I'm from there, I love this, or I'm going there next week and I can't wait to use this. And so it's like...

It's kind of sad how much of coverage is driven by the, have to follow what SEO is saying or what AI is saying we should be covering versus like, what's cool? What's out there? And so if these things that kind of feel hidden to us is really why we started doing this in the first place. Whitney Lee: Exactly, the human connection is just everything.

So when we discover it, like I discovered American Weekender, I was like, there's a real human behind this. This is not written by AI. Like can tell it's not written by AI. So kudos to y'all.

Okay, I want to wrap it up by saying what's the future for American Weekender? What's your vision of like, where is this going to go and where are you taking it? Amy: Mm-hmm. ⁓ my God, we have so many things that we want to do with it.

We'd love to do, you know, like a print magazine component someday. We would love to, you know, do trips, you know, take people along with us as we're eating our way through a place. So much that we can do, like covering American food means that like we will never run out of things to cover. Like truly, like I'm overwhelmed at like the number of places I want to go for it and the number of, you know, dishes I want to dig into and explore.

So, you know, for now, it's It's gonna be the Friday newsletter with our monthly field guides, but definitely in the future, something we wanna grow. Whitney Lee: Forget Rick Steves, like Amy and American Weekenders on the way. Amy: You Whitney Lee: Love it. Well, it's so fun following you.

I'm so glad we got to meet. What an awesome story of how all this came to be. And I'm so excited to see where all you're going to go. We will totally make.

If you want to do South Mississippi and if you want to do ⁓ Gulf Coast, those are my two homes from way back. So we can totally make that happen. But ⁓ this has been so amazing. If anybody wants to follow the Substack or if they want to connect with you, an American Weekender, tell them how they can find you.

Amy: Yeah, so if you go to AmericanWeekender.com, you can subscribe to our newsletter that way, and you can also find all of our field guides. Number 30 comes out this Friday, so we have a deep library of guides around the country. So all our details are there, social links are there as well.

Whitney Lee: Love it. All right, y'all go connect with Amy and her honey, right? Your husband's the other side of this too? Amy: It is a joint project and ⁓ it's been so fun to do it together.

Whitney Lee: Love it. Love a couple that works together. So, well, thank you so much for taking time to come on the show. All right, y'all.

We will see you on the next episode. Amy: Thanks so much for having me.