Sam Wachs (@schmoomer on IG)
Tyler Bainbridge and I are sitting outside the New York City TikTok hotspot Fanelli’s on a muggy September afternoon, joking about being play-pretend downtown scenesters taking up the corner of a busy SoHo intersection. It’s actually pretty funny, given the former Facebook software engineer is the main person behind Perfectly Imperfect, the 84,000 subscriber-strong Substack that’s made him a semi-reluctant authority on NYC cool — not that he’s really complaining. His only gripe is with the sheer amount of shameless self-promotion that’s currently taking up a large part of his inbox.
Originally started in 2020 by Bainbridge and college friends Alex Cushing and Serey Morm (the latter of whom is no longer involved), Perfectly Imperfect is a biweekly email newsletter sharing recommendations — as specific as books to as general as “walks in the cemetery” — from a rotating roster of buzzy A-listers, influential creatives, and emerging artists alike. Spread across disciplines as varied as songwriting, meme-making, and scamming, its guests have included pop star Charli XCX and experimental producers Body Meat; indie sleaze icon Meg Superstar Princess alongside The Bear’s Ayo Edebiri; and rising indie rocker MJ Lenderman a few scrolls away from Red Scare podcast host Dasha Nekrasova.
It isn’t uncommon to also spot a playlist or a handful of recommendations from Bainbridge himself, a self-proclaimed “music nerd” who’s thrown shows for NYC dance trio Fcukers, gassed up Chanel Beads, and sent out a Snow Strippers-curated newsletter. Because cool stuff is meant to be shared, for the Perfectly Imperfect founder, it’s all about using his seal of approval to bring attention to some of his favorite new musicians — just don’t call him a “tastemaker.”
Going from a software engineer at Facebook to running a viral newsletter like Perfectly Imperfect is quite the career transition. How does that even happen?
It kind of started as a little project to do on the side while working my boring tech job during peak COVID. I was getting fed up with how algorithmic and homogenized everyone’s taste and curation was getting, and I thought it would be interesting to start something that brought it back to a more human level and what a certain individual likes.
For the first few years the formula stayed the same, which was just asking people for five recommendations. It never had to be a product or [piece of] media; it could be anything. So people would talk about parts of their routine and share little bits about themselves, which painted a nice picture of who they are. Then, slowly, it grew this pretty large, organic following.
Who’s the quintessential Perfectly Imperfect subscriber?
A lot of people think [our subscriber base] is very New York-centric, but it’s really people from all over the world who are interested in learning from others. I also think there’s the meta-recommendation of who we decide to have on Perfectly Imperfect. You may think everyone already knows who someone is, but the truth is that a lot of people don’t. They want to check out their music and their recommendations, and we’re kind of co-signing these people that we think you should check out.
So you’re kind of the ultimate curator of influential cultural figures? The tastemaker of tastemakers?
I hate the word tastemaker but, unfortunately… I don’t know. I’m really just a music nerd and a fan of culture that now has a seat at the table to contribute [to the discourse].
[The newsletter is] not really about being top-down; it’s a nice snapshot of who someone is. People do a bunch of profiles on a press tour, but a lot of them tend to hit the same notes, so I imagine it gets a little boring for the person who’s doing the interviews. I think people just like that they can come on Perfectly Imperfect to talk about five random things, and, as a reader, you learn about a different side of them.
Sam Wachs (@schmoomer on IG)
Right, you get to learn some more fun tidbits about these people. It’s less stiff than a prepped PR statement.
I think we’ve been able to capture that vibe in a way that hasn’t really been tainted yet, because it’s a genuine reflection of what someone likes. I think the idea of like “five albums that influenced your upcoming album” is kind of tired, and people don’t always want to answer those questions. It’s like, they want to talk about where they get a sandwich every couple days, right?
That reminds me, I noticed that you’ve done a bunch of newsletters with rising artists like Chanel Beads and Body Meat. Are you trying to concentrate more on the underground music space?
Well, we’re trying to be what we don’t see in music journalism now. There’s this opportunity with Pitchfork semi-kicking the bucket, but I also don’t just want to feature musicians. We are thinking about doing some new stuff with them though, like that old Talkhouse article where Lou Reed is reviewing Yeezus and articulating his thoughts on why it’s great. I’m trying to put together more moments where you get someone legendary and interesting to review a new artist.
Like DJ Michael Imperioli.
Yeah! Get him to review someone’s film or something. That’d be so cool.
At what point were you like, “Holy shit, this is actually huge” in terms of Perfectly Imperfect?
After that first party we threw with The Dare, we got a big write-up in The New York Times, and it was the biggest jump in subscribers we’ve ever had. I don’t particularly like that piece [“What the ‘Cool Kids’ of Perfectly Imperfect Are Super Into”]. I mean, it was catnip for Twitter haters. Like, I would just go on Twitter and see, like, a tweet that’s like, “These aren’t the fucking cool kids” or whatever with 10,000 likes.
I didn’t realize you guys did live events.
Yeah, the flyers get slightly lost in the mix, but we threw the party where the “Girls” music video was filmed. We also did a lot of the early shows for Fcukers and, the year before that, we had Snow Strippers, who were new at the time, and The Hellp.
We’ve also thrown so many shows, and it’s the only real-life part of what we do. We did two South by Southwest showcases in the spring. One was headlined by Fcukers and the other by Chanel Beads.
How often do they happen?
We throw shows every month or two, so pretty frequently, but I’m taking a slight step back from that. I love doing it, and watching a show we had a hand in throwing is one of my favorite parts of doing Perfectly Imperfect. But it’s a ton of work — booking, having to delicately balance a lot of people’s egos, monitoring ticket sales. And, the truth is, there aren’t that many venues and DIY spaces you can play in Manhattan these days. We’ve thrown shows in the basement of Italian restaurants and weird places like that, but it’s pretty hard to find something that isn’t a larger venue.
Yeah, booking talent in particular is rough. I’m assuming it was kind of the same for the newsletter at the beginning?
At the beginning it was really hard. You send a ton of emails and you get a lot of “no thanks,” but eventually, some of those turn to a “yes.” And when you get the right “yes” or have grown enough, people take us more seriously. A lot of publicists now read Perfectly Imperfect, which is a huge benefit compared to 2020, when I was just sending cold emails as some random guy.
Now we have a lot of people begging to be in it. There are a lot of publicists, people asking their friends to text me, and it’s hard to navigate. I never want to start featuring people that I didn’t actually want to feature, but they got pitched. Then, you’re suddenly losing the charm you had initially.
How do you decide who gets one now?
We still try to strike a balance of having really famous people and some random writer that I think is small and deserves the same spotlight. I think that balance is really important to what we do. I don’t see that going anywhere.
But I also realized that we shouldn’t restrict all this recommendation stuff and tastemaking to just celebrities and people that I deem “important” enough to feature in the newsletter. We all send albums and articles or whatever to each other in group chats anyways, so I built a whole social media platform where now you can make recommendations, bookmark [cool things], and add it to a list to read later. We should let anyone make recommendations — democratize it.
This interview has been lightly edited and condensed for clarity.
