Angela Stefano Interview (The Boot)
Angela Stefano is editor-in-chief of The Boot and senior writer at Taste of Country. She started working at The Boot in 2014 after a series of jobs in the media industry, and has since been focused almost exclusively on country music.
How did you get to where you are today, professionally?
Not to be the cliche music journalist of a certain age, but at least a bit of me getting to this point has to do with when my dad sat me down and made me watch Almost Famous with him. I was either a freshman or sophomore in high school, and my AIM screen name pretty quickly became pennilane988 (the only reason I didn't use that as my Twitter and Instagram handles is because it was already taken!).
By that time, I was writing for NeXt, the teen-written section of The Buffalo News (R.I.P.; they published once a week when I was in high school and college, then cut it back, then finally folded it a few years ago). My mom had pushed me to apply to write for them when I started high school thanks to my affinity for writing terrible poetry and plays in grammar school (cringe!). I was accepted the first time I applied, and then they couldn't get rid of me! Seriously, I wrote for them every chance I got, and I came back during college to do some summertime assignments, too; in particular, I remember an eventful Warped Tour in 2007 or 2008.
I could write volumes about the work I did for NeXt, but the main thing to know is that they published some of my earliest concert reviews and interviews—none of which I'd recommend reading, but the first of which was with Robby Takac of the Goo Goo Dolls, an interview I pursued and arranged entirely by myself. I was only 14 at that point, and it was 2003, so I had to do a lot more internet digging than I might have these days; if I remember right, they even sent me the press kit by snail mail! I think my editor was kind of shocked when I just turned up with the pitch, interview already set up.
I started at Boston University, majoring in journalism, in the fall of 2006 (NYU was my dream until I realized they didn't have a comms school, only a major in their liberal arts program; there's also a funny story about how I applied to the wrong school at Northwestern, but that's for another time). They sat us all in our first journalism class—the whole freshman class in the College of Communication takes COM 101 together—and told us that by the time we graduated, we'd all have great jobs lined up. Do I even need to explain that that didn't happen?
If I'm being honest, I didn't love college. It's fair to say that my classes taught me to write better, and I had some fun hosting shows on the college radio station, but most of the skills I use today, I taught myself or picked up through an internship (more on that in a second) or by freelancing—but it was a weird time, and journalism and technology were changing so much and so quickly, so I wouldn't take that as a critique of my alma mater or professors. However, I did bolt out of there in three years (thanks, AP credits from high school!).
Where I learned the most in college was, without a doubt, my internship with the Boston Bruins. I worked with their communications team—specifically the guy who ran the blog on the team's official website and, when it became a thing, their social media pages—and I loved every second of it. I got to write for the website and do transcription work; in fact, I was a super-fast transcriptionist and got a reputation for knocking out coach press conference transcripts quickly. I stuck around for three semesters (I only left because I was graduating!), and as a bonus, when I moved back to Boston briefly in 2011-2012, I was lucky enough to join their game night staff team.
After graduation in 2009, I moved back to Buffalo, N.Y. (my hometown since I was almost six, until my husband and I moved to Nashville in 2020) and ... worked at the watch kiosk in the mall that I'd been working at during college breaks. So much for a journalism job immediately after graduation! That fall, I landed a receptionist job at ITT Tech (for-profit colleges: do not recommend!), then in the spring of 2010, I found my way to Citi, working as an editor in their research department. That paid well, but was fairly soul-sucking; when they started suggesting that I take the exams to be licensed to write research, I knew it was time to seriously figure out how to get out.
This whole time, I'd been freelancing—largely unpaid, which I obviously wouldn't recommend—and one of those gigs, with a website called the Next Great Generation (a lifestyle site for millennials, the project of a marketing agency), was launching a blog in partnership with Boston.com (the website of The Boston Globe) ... so, when I was offered the job, I decided to pack up and move to Boston, which I thought would be permanent. (Funny enough, I made the decision to accept that job on a flight from Buffalo to Nashville for a family vacation—foreshadowing?)
Long story short: It wasn't permanent, and after quickly making the move in the fall of 2011, I needed to find my way back to Buffalo in the spring of 2012. That's when I wound up getting a job with Townsquare Media, running the websites for their four radio stations in the city. It was music, it was in my hometown, and it was a new-ish company and a role I'd be the first person in, so I'd get to make it my own—I was sold.
I spent two years working with the four stations' DJs, live events staff and other employees to help them create content surrounding their shows and events. I had an awful lot of fun doing it (so. many. concerts.), but I didn't see a ton of room to grow—so when Townsquare bought some of AOL's music properties after AOL decided to shut them down and needed someone to run The Boot, I was game for the opportunity.
I started with The Boot in August of 2014 ... and, here I am. I've been that site's editor-in-chief since that time, but in recent years—and then, even more so when the pandemic started—I've worked more and more for our sister site, Taste of Country, too. Now, my official title is Country Team managing editor—meaning I'm The Boot's editor-in-chief and a senior writer/editor at ToC—and after a couple years of trying to find my way to Nashville, I made it down here to start 2020.
I think that probably sums it up!
Did you have any mentors along the way? What did they teach you?
Jean Westmoore, who has since retired but was the NeXt section editor at the time I was writing for them, played an integral role in turning the little nugget of this career that my parents and elementary school teachers fostered into that feeling of "Yes, this is what I want to do for the rest of my life," and I'm sure I'm just one of many former NeXt correspondents who feels that way. She encouraged my drive and rough pitches (I mean, truly, I was in high school and had no idea what I was doing), and offered me some truly incredible assignments (she even put me on the cover a couple times!). When I started high school, I still thought I might want to be a lawyer, and looking back, I'm positive she's the reason I picked this path despite loving mock trial.
John Bishop ("Bish"), my boss at my Bruins internship, also was (still is!) simply incredible, because he, like Jean, took me seriously, encouraged my ideas and made sure I was learning, but didn't feel like "just an intern." I'm not sure I can fully sum up how much he inspired me and how much those experiences, and his continued friendship, meant then and mean to me now. There is one easily quantifiable thing he did for me, though: He gave me my first experience writing on the web and for social media, which wasn't something I was really being taught in my college courses at that point (2008-2009 was an awkward time with all of that). That internship is, without a doubt, where I learned the most in college.
And while I wouldn't necessarily call them mentors (I think they'd think it was weird, too), I have a number of fellow journo pals who inspire me and offer friendship, guidance and opportunities to bounce around ideas and vent. I'd have gone crazy by now without them.
Walk me through a typical day-to-day.
Oh my, this answer would have been much different a year ago. The pandemic has meant I've gone from primarily assigning stories, planning an editorial calendar and editing, with a side of writing, to a much more even split—probably from 80/20 to 50/50, since I now have fewer freelancers and more help from the team at Taste of Country. If it's not news or something that needs doing immediately, I tend to save my major writing (features, interviews, etc.) for later in the day, or when I work Thursday nights, which is also when I stay up to catch new music coming out at midnight ET. Since we don't have as many events these days, each day is mostly a combination of all of those duties, with interviews and roundtables and such sprinkled in there.
What does your media diet look like?
Well, I definitely spend too much time on Twitter and Instagram (at least I'm not on Facebook much?). I have an RSS feed aggregator that contains both sites I follow for work and sites I follow for fun, some of which overlap quite a bit and are probably fairly obvious: Rolling Stone, Wide Open Country, CMT, Jezebel, BuzzFeed, Slate, Billboard, Pitchfork, etc. etc. I also try to scan the Buffalo News and Tennessean headlines once a day. I'm a sucker for advice columns—I love hearing people's problems, both the mundane and the insane—so I spend a lot of time among Slate's advice-givers, as well as on Captain Awkward and AskAManager.
I've also tried to spend less time watching TV and more time reading and listening to podcasts in 2021 (though I'm slowly working my way through Dawson's Creek, a show I never watched during its original run). I just started Rob Sheffield's Talking to Girls About Duran Duran (why I haven't read it 'til now, I don't know), but I was previously reading Peggy Orenstein's books (great if you're interested in studies of gender and sexuality, especially as they influence us from birth) and Irshad Manji's Don't Label Me. I'm also a sucker for oral histories of all sorts, and Garrett Graff's The Only Plane in the Sky, about 9/11, was phenomenal.
I feel like this sampling makes my media consumption sound really heavy, and that's not totally accurate! As a The Office fanatic, I'm devouring Angela Kinsey and Jenna Fisher's Office Ladies Podcast and Brian Baumgartner's The Office Deep Dive as they release new episodes each week. I also religiously listen to Billy Dukes' Country Music Media Podcast (full disclosure: he's a co-worker and friend, and I've been a guest), and am looking forward to Lorie Liebig (another friend)'s official launch of More Than a Cowgirl. I pick and choose episodes from some other pop culture/music-focused podcasts, too: On Wednesdays, We Wear Black, The Mortified Podcast, The Throwback Podcast and some others.
What's the best way to pitch you on doing a story?
Please, please, pretty please, do not try it via social media (my personal accounts or my sites' accounts) or my personal email address—or, oh my god, via text! I am hyper-organized (#TooVirgoToFunction), and if it's not bookmarked in my work inbox to look over, it's not going to happen. Plus, those other places get filled up with too much spam, and your pitch is likely to get caught in there. (I'm not saying I don't get a TON of work emails every day, some of which are spam, but at least there, I know to look over everything carefully.)
If you're coming to me, make your subject line clear and concise, and make sure your ask is right at the top. Of course, I understand that people send out lightly personalized pitches to a large number of people in addition to very specific asks, but I've mistaken the latter for the former so many times because the ask is so far down or the subject line is so broad. Those are, more often than not, the pitches I miss the first time around, and then someone has to follow up with me, and then I feel a little bit bad about it.
Again, if you're coming to me with one of those lightly personalized pitches, tell me what's possible and what you're after! I love brainstorming ideas, and I'm more than happy to be the one to start an ask for an interview or a premiere or whatever, but if you're coming to me, it's frustrating to receive a pitch with a whole bunch of info about an artist/project and the ask "Can we do something about X?", then I'll reply with some ideas and get back, "Oh, that won't be possible." It feels like a waste of time.
Last thing: Please don't be afraid to follow up with me (again, email is much, much preferred here—it's just how I stay organized). We're all inundated with emails, and I try my best to reply to every specific ask I get, but they slip through the cracks, especially when it's a busy week.
(PS: If my work is relevant to you and you don't have my email address, it's angela@theboot.com.)
What's the most gratifying part of the job?
Internally: Getting the story just right—getting that lede perfect, or finding that absolutely killer end quote. It's so stinkin' satisfying, it helps me feel like I'm doing the interview subject/feature's focus/news item justice, and it's also a little bit of personal validation that, yeah, I know what I'm doing.
Externally: Hearing someone praise one of my stories or my work as an editor, or having an interview subject compliment a question or my interview. I know this is a job, but I try every day and every assignment to put my best into what I'm doing so it means a LOT to know people like it, especially when they're people I admire. I recently spoke to Loretta Lynn's daughter Patsy for a feature on Loretta's newest album, and she ended the interview by telling me she was so thrilled to speak with me because they love The Boot, and that she will sit with her mom and read our stories to her. I legitimately cried after I got off the phone with her.
How has your approach to your work changed over the past few years?
I know I just gushed about how I throw myself into my work, but I've tried to get better at disconnecting and remembering that this is my job, not my whole personality, especially since the pandemic started. I always want to do my best and create important, well-written work, and be a good boss and co-worker, but I am a perfectionist by nature, and one with a lot of insecurities and anxieties at that, so it's really important to remind myself that this is music journalism, not the nuclear codes, you know?
A typo or an error might happen from time to time, because I'm human; hell, I might have a really off day and mess up a bunch. That happens to everyone, at work and in life, but it just so happens that my work mistakes are sometimes public. (I think that's also a good reminder to the people who email to rudely tell me that they can't believe I said Carrie Underwood's Cry Pretty came out in 2017 when it really came out in 2018 and god, you must be so stupid and bad at your job to have gotten that wrong ... er, *ahem*.)
I've also tried to be more intentional about the stories I choose to tell and creating space for those on the fringes. When I started at The Boot in 2014, that was as easy as starting to cover newer/smaller artists and more Americana/folk/bluegrass/alt-country, rather than just looking at mainstream country, but I know those early efforts weren't always enough. For example, I wasn't always focused on making sure lists and other features that included multiple artists offered a range of genders, races, etc., because I thought, "I should be judging based on the music, not their gender, race, etc." Now I understand that's far too idealistic and that, although my intentions (to put forward the best music possible) were good, the implementation was misguided, partially because of outside factors that elevate younger, straight, white, able-bodied, generally male artists more often and more broadly. I know I'm not always (ever?) getting it perfect even now, but I'm definitely more on the right path.
Where do you see yourself in five years?
I categorically hate this question, because where I am now is pretty much as big as my dreams got (Okay, technically, the dream was writing for Rolling Stone, but journalism has changed so much that I'd call this pretty damn close). Generally speaking, I hope I've continued to get better at my work and tell important stories. I have some podcast and book ideas saved in my phone notes that I'd love to work toward, but in the interest of work-life balance, I'm not at the point of deciding to pursue them yet—but maybe by five years from now.
I hope I'm someone you'll see moderating panels, or being on panels, or being a guest commentator on music industry matters—not because I want the recognition (honestly, I hate being the center of attention—it's taken me a long time to complete this questionnaire because I want it to be perfect and want to not sound like an idiot!), but because that will mean I'm writing about people and ideas worth elevating.
Where do you see music journalism, in general, headed?
I really don't mean to sound "back in my day ..."-y or "the internet is ruining everything!"-y, but ... there's less room for experimentation and the publication of meaningful stories that may not be instant pageview-getters, at least in some spheres. Not everything should have to be instantly grabby or appeal to the masses or get tons of traffic; some things need to exist because they're good, meaningful ideas, and I'm grateful to smaller outlets and self-publishing and places that are willing to take chances or serve a very specific niche for that reason.
I'm not sure if that's a good answer, or if I have a good answer to this. I do think, though, that we've learned in the last year, and even in recent years, that you don't need a major platform to start finding an audience, which has both its pros and cons.
What would you like to see more of in music journalism right now?
Personally, I'd love to be able to commission more longform pieces (op-eds, thinkpieces, feature interviews—whatever) from freelancers. I'm not saying that's not happening in music journalism more widely—I love Elamin Abdelmahmoud's work on BuzzFeed, and Jon Freeman has done some stellar pieces for Rolling Stone Country recently—but they're both on staff at those outlets, and unfortunately, I think because of the pandemic and budget cuts, those pieces are falling to staffers more frequently. I'm excited to get to take interviews more often for The Boot, but I have some great freelancers I work with (hi, Carena Liptak, Marcus K. Dowling and Annie Zaleski, just to name three of them) who are so knowledgeable when writing those sorts of stories, in a way that I don't necessarily have the brain capacity to be while I'm trying to run the site.
TL;DR: More smart, unique voices, please and thank you.
What would you like to see less of in music journalism right now?
I don't necessarily want to say I want FEWER podcasts, but it does feel like EVERYONE is launching one lately, and some have been great—but others have just been okay. So, maybe I want fewer podcasts that lack a more coherent, overarching angle across the series.
Also, less not-properly-labeled sponcon! That's just not cool.
What's one tip that you'd give a music journalist (or editor) starting out right now?
Listen. To discourse and to music. You don't have to agree with or like everything you hear, but the more you absorb, the broader your list of sources, analogies and potential stories becomes.
What artist or trend are you most interested in right now?
I feel particularly energized by the artists who are emerging right now. I've heard some particularly strong debuts and early-career work recently. I couldn't turn Morgan Wade's debut album, Reckless, off for like a week after I first got it, and I'm similarly obsessed with Amythyst Kiah's solo version of "Black Myself" and Lily Rose's single "Villain," and I can't wait to hear more from them. I also think Breland's promotion of his single "Cross Country," with all of the video elements, is brilliant; I'm always here for a "genres are silly and unnecessarily limiting" argument!
I'm sure there are others, especially not in country and its related genres, but I'm never great about being put on the spot for new music recommendations.
What was the best track / video or film / book you've consumed in the past 12 months?
I am terrible at picking favorites, so this is a next-to-impossible question for me. I did devour Brandi Carlile's memoir very quickly, and it made me completely reexamine the way I see her as an artist, in a good way.
Anything you want to plug?
Hmmm... I'm really proud of a recent feature I did on a newer country artist, Hannah Dasher (it was one of those times where I just knew, instantly, that I had the perfect lede), and I'm equally thrilled with how a feature on Loretta Lynn's new album turned out, because it's from the point of view of co-producers Patsy Lynn Russell and John Carter Cash; I didn't get to speak with Loretta for the story, but I think not having it include her point of view makes it a bit unique, and stronger than it would have been as an artist interview. I was also recently on Billy Dukes' Country Music Media Podcast talking about the ACM Awards—you can listen here.
Otherwise, I'm only moderately on social media, but you can find me on Twitter and Instagram.
Oh, one more thing: I'm not at all related to these outlets, but I'm so impressed by the work Holler Country and Country Queer are doing. Please go check them out.