VANCOUVER – I’m awoken by two distinct sensations.
Stu’s sandpaper tongue, scraping across my right forearm, and the haptic alarm of my Apple Watch buzzing against my left wrist.
It’s 5:15 a.m. and I am starting today the way I have started almost every day since New Year’s. Tired and anxious, but also excited.
I roll out of bed and quietly follow Stu into the hall. Behind a curtain, I can see blue blots of daylight slowly flooding the eastern sky. I tiptoe to the kitchen and grab a spoon out of the cutlery drawer. Stu merps with excitement. I open the fridge and retrieve his half-eaten can of Rabbit Au Jus. I plop the brown meat into his silver dish and leave the dirty spoon on the counter. A soiled reminder to myself that, yes, he has eaten and, no, don’t let him fool you.
As he tears into his breakfast I fill the kettle with water and place it on the back left burner. I turn the knob and the stovetop bursts to life, its blue flame kissing the kettle, slightly blackening its metal base.
I’m not a natural morning person. My circadian rhythm has always marched to the beat of its drum. It would let me sleep until 11 a.m. if it could. But there is life to be lived and work to be done. Between my real job and real commitments, early mornings are the best time I’ve found to write. And so I trade my warm bed and Goop eye mask for a dark living room and a blank page. I trade comfort for these so-called Human Pursuits.
In the three years since I launched the ‘sletter, I’ve learned that every successful side gig runs on self-confidence and self-delusion. Confidence kickstarts the project and convinces you that you have something to offer the world, while delusion cheers you on quietly from the sidelines, telling you things are going well, even when they aren’t. It’s a complex psychological cocktail to nurse by yourself, which is why I’m excited, this morning, to chat with Tyler Bainbridge.
Once called the “Tom from MySpace” of this generation, Tyler is building an entire universe around his popular newsletter, Perfectly Imperfect, which taps notable names, as well as total unknowns, for recommendations like Zicam nasal swabs (The Bear’s Ayo Edebiri), raw milk (Bandsplain’s Yasi Salek), giving blood (Jack Corbe from NPR) and Laneige Lip Sleeping Mask (Charli XCX). The short, digestible format is so popular that Tyler has recently launched P.I.FYI, an app and website where anyone can share their interests. Awash in style and sincerity, it has become my favourite place to hang online.
Our interview is scheduled for a couple of hours from now, which still gives me plenty of time to get to work. A corollary to these early mornings is that I can no longer do late nights. Leah’s also trying to get more sleep this year, so we’ve instituted a family bedtime: 9:30 p.m.
The scene is Modern Dickensian. We both received these small book lights for Christmas that cast our bedroom in an amber LED glow. She reads Dune and I read Scar Tissue by Anthony Kiedis. By 10:30 p.m. I’m usually out cold.
I call it “candlelight hours.” I cannot recommend it enough.
ES: I get the impression you’re quite busy at the moment.
TB: Yeah, it’s an interesting period in the newsletter. It’s in flux between what it is and what it can be.
ES: Can you tell me more?
TB: Now that I’ve introduced the app I think there’s an opportunity to become something bigger than just a newsletter. To have things more fleshed out on the editorial side, and integrated with the app in some interesting ways. I’m trying to be the change that I've always wanted to see in this stuff, which sounds like such a bullshit tech thing to say, but I think that it’s possible.
ES: I was reading some of your old interviews and you were hinting at all of this, even as far back as a couple of years ago. It feels like you’re a mastermind with it.
TB: Laughs. Yeah, there was one interview I remember doing – it’s probably the one you’re talking about – where I said everyone could do a Perfectly Imperfect (P.I.) someday. I had the idea for a long time. Once layoffs started happening at Meta, my former employer, I had my fingers crossed that I would be among those affected, which is a crazy thing to say. But the severance allowed me to pursue this idea I’ve always wanted to do without going broke.
ES: There isn’t much optimism around tech or social media these days but P.I.’s community is so bubbly and inviting. It’s a really nice corner of the internet to hang out in compared to, like, Facebook.
TB: There’s probably a bit of this in everybody who starts something. Like, I’m sure that Mark Zuckerberg’s intentions out of the gate probably weren’t evil. Maybe they were, I don’t know. But over time, the industry forces you to compromise, and things change slowly until, eventually, it’s different than what you imagined it to be. That’s something that I’m cautious of. I think that’s what ultimately makes a lot of these places become toxic, or money pits for advertisers. It’s something that weighs heavy on me and is a big concern. It’s a big responsibility to try to build a community like this and to do it right.
ES: Do you feel like a leader? It seems like you’re thinking about this in a way that opposes the sort of run-and-gun, über-disruptor mindset we’ve seen for so long.
TB: Part of that is because P.I. has grown organically. It’s precious to me. I feel connected to the people who connect with the newsletter. I heard someone describe my presence on the app as a “small-town mayor” which I think is really nice. I hope that feeling can scale as the user base grows.
ES: One P.I. user recently shared that they’ve “broken free” of Twitter, and I noticed you re-recommended it. It had me picturing you throwing darts at a picture of Elon Musk’s face.
TB: Laughs. I’ve seen people compare what we’re doing to Bluesky and these other Twitter alternatives, which are just a copy and paste of something else. Those sites are different communities in different places, but ultimately they are the same thing. When I see people use the P.I. app as a place for internet jokes or memes, it feels wrong, and I felt I had to say something because I saw that behaviour percolating, you know? It’s okay in small doses but I don’t see P.I. as a haven for people who are done with X (formerly known as Twitter).
ES: It’s funny, even as we were setting up this interview I had a voice in my head asking “Do you want to share P.I. more widely?” Because I’ve had such a good time using it. I want to protect that fun sensation a little bit. I don’t want to invite everyone to use this thing, which is perhaps selfish.
TB: I think there are a few things that play into that. I think people are sometimes shy to share what they like if there are a lot of people they know in the space. If it’s friends or people you’re close with, of course, you feel comfortable, but there’s a reason why we aren’t all going on Instagram and shouting about the movie we just watched. I think people like the app’s semi-anonymous nature, and that might change as it becomes as ubiquitous as Facebook.
I have mixed feelings about P.I. scaling. It’s not something that I want to keep small, because keeping things small intentionally feels forced. Everything we look back on that remained cool or niche wasn’t necessarily by choice… Also, this app would only get more helpful with scale, being able to seek out recommendations from people and stumble upon things… It feels like something anybody can use. My mom uses the app, and she’ll recommend something like shepherd’s pie and it feels normal, compared to someone talking about the new Bladee single. It isn’t meant for hyper online Gen-Z kids or downtown artists, or whatever. I believe anyone would find it fun.
ES: What’s your mom’s username? I want to follow her.
TB: It’s @tylersmom. Laughs.
ES: Amazing. But it’s interesting hearing you say all that because I’m realizing that, if the app was relegated to downtown NYC, I wouldn’t be part of it since I live on the other side of the continent.
TB: Growing up, I didn’t have a cool older brother or someone to learn about music or film from. I had to learn about it backward, going from being a Call Of Duty teenager to discovering bands and other things. It was something that felt intentional and almost academic for me, and I wanted the newsletter to be a similar portal for people. I don’t want it to feel like an insular thing. If some kid is reading P.I. and learns about the band Voyeur from me talking about it, that is cool to me.
ES: I think the spirit of our two projects is pretty similar. My newsletter also wants to turn people onto new stuff but in a longer, haters-would-say-more-bloated, fashion. Like, here’s a 20-minute read on this thing or person you’ve never even heard of before because I think you’ll like it.
TB: I think they’re both character portraits, and that’s something I didn’t realize until much later running the P.I. newsletter. At first, it was born out of this malaise from everyone talking about the same things, and having the same taste. I thought starting the newsletter to get away from an algorithm and to learn new things from other people would be interesting, and a way to get back to human curation. As time went on, I realized it’s what you’re talking about. It’s a capsule of an individual, what they were like at that time, what they were working on. P.I. gives you some of that from the intro, and through the recommendations. You learn not just what a person’s taste sensibilities are, but why they decided to share certain things.
ES: It’s a study of how people are crafting their identities.
TB: In a way. In the purest sense, it would be great if people only shared exactly what they like for no other reason, but that’s not real life. We choose to share different things with different audiences. Like, you’ll tell your friends about different bands than what you recommend to your parents.
ES: You’ve mentioned in other interviews that your life is sort of being funded by your Meta severance. What’s going on there?
TB: That severance wasn’t forever, I’ll put it that way.
ES: Laughs.
TB: I’m diving into my life savings to try and make this project real. There’s some income coming in from the newsletter, the paid subscribers, and the app has a paid tier, which helps but it’s not enough to pay rent and live comfortably. I’m trying to figure out how to get P.I. to the point that it’s my career, and sustains my life. It needs to grow at a certain rate. I don’t think it can go back to being a pet project. Even when I was working full-time and doing the newsletter for the past few years, my free time was very limited. Trying to run two or three features a week, booking guests, and putting everything together, on top of a full-time job, was already a lot. If I go backward and try to get a full-time job now, it won’t work.
It would be great if people only shared exactly what they like for no other reason, but that’s not real life. We choose to share different things with different audiences.
ES: That sounds a little stressful.
TB: I’m definitely stressed. There are certain options and avenues that can change the future of P.I. that I’ve been thinking about a lot, whether it’s taking outside money or bringing in advertisers. Things that may be, potentially morally compromising to me but ultimately the only solution forward.
ES: You’ve talked a lot about profit and scale. Basically, I guess I’m wondering, are you a capitalist? Laughs.
TB: I mean, I’m a capitalist in that I’m not making this app for free. I coded it non-stop for four months of my life. January especially was a blip. I’d code from 8 a.m. to 11 p.m., which made me insane. Every day was exactly the same, blending into the other.
I think people, especially on the internet, expect a lot of charity. People expect things to be free. That’s especially true of apps. It’s weird to think that something exists out of nothing and should always be that way. I don’t know. I hope people will understand that P.I. ultimately needs to make money, and I need to be pure and honest with how I go about that, and not compromise the app itself. I’d rather see everything fade away than make it so that every three recommendations you see an ad for drop-shipping, you know?
ES: Maybe we should organize a PBS-style fundraiser for P.I. Get Charli XCX and Big Bird working the phones. It’d be pretty cool.
TB: Yeah, a little money ticker counting up. Everyone calling in with donations.
ES: I think our generation still has some hang-ups when it comes to discussing money. Like, it’s never been cooler to complain about billionaires online but for anyone who is a working-class creative, it feels like there’s a hesitancy or shame. Maybe it’s because everyone is so self-aware of their own privilege that they feel like their struggle isn’t legitimate…
TB: There’s a weird balance you have to have. I tend to have a Gen-X mindset on selling out. I don’t know, maybe it’s bullshit… Frost Children, a band I’m friends with, has this song called “Bob Dylan” where Angel, the singer, ruminates on this idea of what’s punk and transgressive. She has this funny line where she says maybe the most punk person on the block is Jack Harlow smiling with a Sweet Green bowl on the billboard. Since the 2000s it’s become more acceptable to do a Sprite ad to pay your bills. People aren’t going broke to be cool or punk.
ES: I always think there are people I’d rather see getting money than Jack Harlow. Like, some people are not necessarily good for the spirit of society, whereas someone like you, who seems to grapple with it all, is at least more interesting or more relatable.
Unrelated, but you’re a DJ right?
TB: Yeah, like everyone else. I got asked to DJ a book release party and learned very quickly. It’s fun, I enjoy it, but I haven’t done it in a while because I’ve become a bit of a hermit.
ES: It doesn’t help that Charli is taking all the gigs, man.
TB: I know, it was between me and her for Boiler Room.
ES: Were you at Boiler Room?
TB: I was, yeah.
ES: What did it smell like in there?
TB: Exactly how you would think. It was a bunch of sweaty Bushwick Charli fans. It was fun, though, really cool. The music was good, she brought a good energy.
ES: The P.I. guest list is pretty blue chip. Have you always felt comfortable moving in these spaces or do you feel like an outsider?
TB: When I started the newsletter, I wanted to work on something I could get excited about. I had zero connections in this world. I can’t even stress how little connections I had. I just wanted to make something for my friends. I was starting to ask them to do the newsletter and, at some point, I started taking bigger swings. And some of those people started saying yes, and then those yes’s started happening more often. It’s grown from nothing… From the outside, it may look like I’m an insider, but I still feel like an outsider. It’s an uphill battle, you know? You need to grit and push through it and not give up. That sounds very TedTalk but it’s real. There were so many points where there were lulls in subscriber growth or I couldn’t book someone I wanted, but eventually, the meter changed, and things started to move in th right direction.
ES: Man, I’ve had all of those same issues. I’ve also learned that bigger names don’t always spark the growth you imagine they will. And that’s not because of the person or their answers, it’s just that life is rarely that straightforward.
TB: Yeah I think the thing is slow, organic growth and having something sustainable. The big moments for us have been interesting press moments. We went through the wringer on the first one. We were in the New York Times and the headline read “What the ‘Cool Kids’ Are Super Into.” It was stupid. But it sparked this Twitter backlash. People were tweeting about us and getting 50,000 likes. Your brain isn’t meant to see that kind of thing. At the same time, the article resulted in 12,000 new subscribers in a day, which is huge. This most recent press cycle, too, was good for that. We got like 20,000 new subscribers in that first month which is great.
ES: The app has so far avoided integrating video. Is that a conscious decision?
TB: I don’t think every app needs a short-form video section. I already go on Instagram and have my senses assaulted whenever I’m listening to music. It takes over my audio and it pisses me off. It’s inescapable on most platforms. I think you have to have a certain degree of restraint when you're building something like this. There’s no reason to have videos attached to most of P.I.’s recommendations. I don’t think it’s important.
I think photos do help. If you’re recommending an item or food or something, the visual aspect is helpful to the person reading it. It’s not just an engagement metric… But I think there’s too much video now.
ES: What do you think of TikTok and its effect on the attention economy?
TB: I think there’s probably a lot I could learn from it. Our social game isn’t as good as it could be. I’m hesitant to change, and that style of content isn’t something I can see myself doing. But I think it can be helpful. Like, the fact Shoegaze is having a moment because Gen-Z is discovering it on TikTok is cool… Like, who gives a shit that this kid is finding My Bloody Valentine? Maybe he’ll start a good band.
ES: It seems like you’re pretty anti-gatekeeping.
TB: I am anti-gatekeeping. Some people are cool, but won’t use the P.I. app because they don’t want to give away their special sauce. I get that it’s part of their identity, but it’s stupid. It’s an ugly attribute in people, that you don’t want to share a band with people. I’m guilty of it too, to some extent. I stopped listening to Frank Ocean because the fandom bothered me. That’s a bad trait that I’m not proud of. But I think the urge to share is important.
We do a music column occasionally and I usually try to shout out bands that are smaller and don’t get coverage for whatever reason. I think using our platform for that is better than telling people the new boygenius album is awesome. That’s not helpful and it doesn’t really put anyone onto them. Using your platform to promote smaller artists makes a huge difference to them.
My mom uses the P.I. app, and she’ll recommend something like shepherd’s pie and it feels normal, compared to someone talking about the new Bladee single.
ES: The idea of not shouting out boygenius is so funny. Laughs. But we should talk about The American Analogue Set real quick. You’re one of the first people I’ve seen talking about that band online in a minute.
TB: Lindsey Jordan from Snail Mail recommended them when she did the newsletter. It was one of those moments. Like “How did I not know about this? How did this escape me?” I’m always seeking those out because there are a lot of them. You think you know everything and suddenly a band like that comes into your life. Like “How did I live without it?”
ES: That’s so cool. I found out about them in, like, 2009 because Mark Hoppus had a podcast where he talked about music and he shared “The Postman.” So shoutout to Blink-182.
TB: Woah, I would’ve never expected that. I also didn’t know he ever had a podcast.
ES: Yeah bro, he was on the front lines. You should get Blink to do P.I. Laughs.
TB: I would love that. I’m always trying to get old heads in the mix, or people who are legacy artists. A big one for me was when we got John Cale from The Velvet Underground to do it, or Will Oldham from Bonnie Prince Billy.
ES: Totally - but man, American Analogue Set is a special band. I find Know By Heart so relaxing. Put that shit on and go for a little bike ride? It’s beautiful.
TB: That record and the one before it are slightly different. One’s louder and one’s more quiet.
ES: The whole thing gives me a real wistfulness for Austin, TX in 2003. Like, Friday Night Lights, Explosions In The Sky, all that sort of ambient, cinematic stuff.
TB: That’s cool, I didn’t know there was a movement with a specific sound happening in Texas then.
ES: I don’t know if it’s a movement for anyone but myself. I probably discovered those two bands around the same time and started romanticizing the fact they’re both from Texas.
TB: Explosions In The Sky was an early one for me. It was one of the first 10 or 15 bands I learned about in high school that changed my taste. I never listen to them anymore, so I don’t know if it would hit the same, but it hit like crazy then.
ES: Buddy, The Earth Is Not A Cold Dead Place? Sheesh!
TB: It’s an all-timer.
ES: Three guitars and all of them are playing the best riff you’ve heard in your whole goddamn life.
TB: So sick. Another big one for me was The Shins. I’ve been revisiting them a lot recently. I feel like they haven’t had a proper revival, but Chutes Too Narrow and a lot of their albums are really fucking good.
ES: You’re also kind of an emo guy right? You like Cap’n Jazz?
TB: I’m not a hardcore emo guy, but I like the more raw side of things. Cap’n Jazz is more intense to me than American Football, but I like both bands a lot. Have you ever listened to Brave Little Abacus?
ES: No.
TB: They’re fascinating to me. I found out about them through RateYourMusic, which is a site that’s been around for like 30 years. If you go to its Midwest emo genre page, Brave Little Abacus is considered the top Midwest emo album of all time. It has a ton of reviews. But they’re from New Hampshire and they had a small run in the late 2000s. They made some incredible music, but the fact that they’re the best emo album of all time for this segment of people is fascinating.
ES: I’m working on a theory that emo is just the white boy blues. I know all rock music is derivative of the blues but I think emo is the whitest form of it. Like, you can trace the influence of the guys in these different bands, and the side projects that spin off. The genre has a fixation with lineage that feels similarly passionate to what I see from real blues brothers and sisters.
TB: That’s funny. People are still very influenced by that sound. You don’t hear it at all in New York, but especially in the parts of Massachusetts where I’m from, every band you see at a local show or bar is doing that.
ES: You mentioned on P.I. that you’re thinking about doing a bike trip from New York to Montreal. Tell me more.
TB: I got into cycling last year and it’s been a really good form of exercise for me. I like biking a long distance and sitting with myself for that time. Moving your body feels good after sitting in an office chair for three months.
But yeah, it’s a big goal. I’ve never done anything remotely close to that. I’ve hardly camped much in my life, but it would be cool to do. There’s an official trail connecting the two places called the Empire State Trail. It goes straight up the state. It’s ambitious but I want to do it. I have a friend of mine who’s willing to go with me.
ES: That feels like a movie.
TB: I know right? It’s something that I’m working on. I think it’s good to have goals that are less oriented around work. Like, I want to grow the newsletter and the app, but I need something to aspire to outside of that, too.
Tyler Bainbridge publishes and operates Perfectly Imperfect. He lives in New York.