We have about 400,000 people that have signed up for Perfectly Imperfect, and we fully intend to hit hundreds of millions of users within the next few years.
If you could name three or four significant milestone guests over the lifetime of the project. Charli XCX. That was, like, a real moment of, "Oh, shit. We're like-- We're starting to make it." This is how you grow.
You feature a person, they share it, those people sign up. That's definitely how the growth engine works. We can feature Francis Burk Copeland, then The Rizzler, and then some random podcaster, and it, like, all works.
The internet I remember. That seems to be your value statement. I don't wanna watch a fucking AI Netflix show. I don't wanna listen to a song made on Suno.
I want to interact with real humans and engage with human art and build a platform where you can connect with other humans.
There's hundreds of millions of people that are gonna really want a pure place to hang out, really have a place to be expressive and connect with real people. Welcome back to the Creator Spotlight podcast.
My name is Francis Zehrer, and today we're speaking with Tyler Bainbridge, co-founder of Perfectly Imperfect. This is a pretty unique story among our guests.
PI started as a newsletter on Substack in 2020 and then left the platform about four years later, still with an editorial arm, but they built their own app and platform, which now has hundreds of thousands of users.
So this is a pretty special story about what a for-fun creator project can become. Enjoy. [upbeat music] So what is Perfectly Imperfect today in practical terms?
By which I mean it's an app, it's a newsletter, it's an Instagram account, it's an events platform, and it's a company with multiple full-time employees. Am I missing anything there? No. That, that's it.
I mean, we call it a social magazine. You know, that's, that's something that's new after we created the platform around it. Hmm. Um, you know, it's just...
It's a place to share your taste and discover new things that are, you know, not fed to you by algorithms. That's, you know, that's why we started Perfectly Imperfect in 2020, and that's why we're still doing it today.
Yeah. What does that term social magazine mean? You, you, you only started using that after you launched the app and website? It's been something I'm playing with.
It-- You know, I think as we've added the app and kind of the social platform to what Perfectly Imperfect does, it, you know, it becomes increasingly difficult to explain what it is.
I'm not sure if social magazine is any more clear. But, you know, we've evolved from a newsletter to something that does, you know, a lot more. We do events. We do a lot of different types of content now.
And, you know, I kinda started to shift more towards calling us a magazine than just a simple newsletter.
And the social element is because we, you know, we view everyone's profile and what they post on Perfectly Imperfect as part of the overall experience.
And, you know, it's, it's not just a couple writers that are building Perfectly Imperfect. It's hundreds of thousands of people that are sharing their taste on the platform. It's the guests that we feature.
It's the internal staff. It's, it's really... it's everyone who's involved. Yeah. So that's why we call it a social magazine. Yeah.
Magazine here, like removing the social part, magazine sort of being defined as like, like traditionally a magazine is a condensed package with like a, a specific point of view, a specific taste- Yeah...
bringing in contributors, right? So like this is sort of a... Social magazine here would mean like a scaled, packaged taste product. [chuckles] Yeah, exactly.
I mean, Perfectly Imper- like, we get like six recommendations a second on our site right now, and so it's, it's, like, you know, the volume of content is far beyond something like a traditional magazine.
But we still, you know, maintain our own editorial point of view with the people that we choose to feature on our newsletter and, you know, our Instagram- Yeah... presence and all that stuff.
So, you know, it's, it's curated by the staff, but it's always evolving and, you know, morphing from the users on our site. Yeah. Uh, I wanna give a quick timeline here for anybody who isn't familiar with PI.
So my basic understanding, you can fill this out, is that it starts as a newsletter in summer 2020 on Substack. You launch the Instagram account, I think, at the same time. Um, you turn on paid subscriptions in 2023.
Maybe that's when it functionally becomes a business. The website and app launch in October '24, and you've launched a few features since.
But that being like the barest of bones of the timeline, can you give your version of the timeline? Yeah. So summer 2020, I spent,
you know, my years after college kind of bouncing around a couple different startups, and I ended up working at this, this company called CarGurus in Boston, um, which was never exciting to me.
And when COVID hit, I was looking for, you know, to kinda scale up what I was doing, uh, you know, on the coding side of things.
And I ended up getting a job at Facebook that summer of 2020, and that first week at Facebook, I was already kind of feeling this, like, suffocation of, you know, working at this company.
[chuckles] And, uh, I really needed something to spend all my free time on.
I've always been someone who's like, even when I was working at different companies in the past, I always had some project that I was working on that was, uh, you know, taking up my free time and letting me be creative and build something.
So that kind of, like, coincided with the, the newsletter trend starting.
You know, there were people like Blackbird Spy Plane and some other newsletters that were taking off on Substack, and I was paying attention to that stuff.
And I thought it would be really interesting to build, you know, uh, my own version of that. Uh, at the time, like, I had no editorial, uh, experience, or I had zero connections in the media world.
Like, I was literally just a, you know, an engineer starting, like, a fun newsletter with my friend Alex and our friend Sarai. Um, and the goal from the very beginning has always been the same.
If you go, like, way back in the archive, which is kinda hard to find now, you know, we talk about how it's, it's built to help people escape their algorithm, and that's, like, remained true.
It's always been a talking point about why we started Perfectly Imperfect. You know, the guests were quite a bit smaller back then.
Uh, at first it was really just, like, my close friends that I'm like, "Hey, do you wanna, like, do an interview for this newsletter that I'm starting? You just have to write a couple...
you know, write about what you're into right now."And s- you know, step by step we got people like Emily Sundberg or, uh, you know, eventually like people like Chris Black. Mm-hmm.
Uh, and s- just like podcasters and writers and, uh, just people doing cool things that were cor- sort of within my reach at the time. Yeah.
And it kept evolving and evolving and evolving until we started getting bigger and bigger names.
Um, I think like the- Well just really, wait, really quick for, uh, like the early content, and this is still what's at the core of it, but I w- I don't know how many times you were saying the newsletter, how many times per week, but basically it's like here's a person, here's a quick, quick bio, and th- then here's five things they're into, which could be traditional like, oh, a movie, a song, but also could be like an activity or it could be like going to this specific barber in this specific neighborhood or it could be, you know, going on a walk without your phone.
Yes. This kind of thing. Yeah. So when we started it was definitely a l- like more structured. Like the early- Yeah...
interviews were a lot more about like, like specific movies or specific albums or like a, you know, a pair of jeans.
And that, you know, it was interesting to watch that play out where people started to kinda take the general framework of what a recommendation could be and- Mm-hmm... you know, adapt it.
Like I feel like Emily Sundberg pretty early like recommended dyeing your hair different colors, and I feel like that was one of the, the first kinda deviations from like- Hmm...
it not being about a specific thing and just being about kinda like a, a vibe or just something that- Yeah... you know, someone wants to express that you should try too. Not a product. Mm. Exactly, yeah.
So that, that was cool to play out and it, I think it's, uh, honestly shaped a lot of the Perfectly Imperfect DNA over the years, where people, you know, are just looking to express something that made them happy. Yeah.
And, you know, they wanna share that love with other people. Fast-forwarding a bit, you leave Substack in 2024, October 2024, when you build your own app and site. Um, I want to talk about the audience size for a second.
So at the time you left, how many subscribers did you have on the newsletter? In 2023, I started to have these early ideas that we should build a social platform, which is important to know for why we left Substack.
I was scribbling down all these notes in my phone and just, you know, I'd observe that a lot of our readers were creating fan-made graphics.
And for context for the listeners, like we have a, we had a very distinct graphic style at the time.
It was like internet blue, big, bright yellow stars, kinda chaotic collage, a selfie, and most notably a lot of Comic Sans.
And I noticed that a lot of our readers were creating these fan-made graphics and writing about their recommendations and sharing them on Instagram. And I started to...
You know, a light bulb went off and I started to think about what this recommendation format could look like as a platform where people could share all the different aspects of their taste, because I've always been frustrated that, you know, to be a multifaceted individual with lots of interests you have to have Letterboxd and Goodreads and Belly and all these apps for like different parts of your taste, and I really was interested in building kinda this home base for taste.
So I was already taking these notes and I was thinking deeply about this. And then in May 2023, I was laid off from Meta when they were doing these like mass layoffs.
And as part of that, you know, I got [chuckles] I got a nice cozy severance from Facebook, and I was- The seed funding for Perfectly Imperfect we might call it. Exactly.
I was like, "I have this six months of, uh, severance." Like I... "This is the perfect time for me to just go all in on this project and f- figure out how I can, you know, make it a sustainable business."
And that's when we launched paid. It was literally the day [chuckles] after I got laid off.
I was like, "Shit, okay, I need to make some kind of money here," 'cause the newsletter had been completely free before just because I've always loved kind of this, you know,
democratation, d- just democratizing like, uh, access to taste and culture and like not having anything be gatekept. So the... Wait, to, to clarify too, there was no ads or anything. There was no... You weren't...
There was no way it was bringing in any money until 2023 when you got laid off. Yeah, exactly. So for the first three years almost. Yeah, yeah.
We had thrown a couple events at that point, um, all of which like either lost money or barely broke even. I've always just done events more just as something fun to do.
Um, but yeah, we had not made a single dollar, uh, on Perfectly Imperfect for those first three years. Mm-hmm.
So okay, so then you start planning for the platform, the website, build your own platform, leave Substack around that time, around the time you start turning it on paid and start thinking about this more as like something that you're actually doing as a business.
Exactly, yeah. The day I got laid off from f- Facebook, I... It was a massive moment of change in my life- Mm-hmm...
um, just like embarking on this new part of my journey, and I was just like walking around and I got this like really kind of psychedelic phone call. This guy on Instagram, his name's Robbie Barnett. He's a filmmaker.
I didn't know him at the time, but I got a DM from him that was like, "Hey, do you wanna hop on a call tomorrow?" And I was like, "Okay, sure. I'd like to-" [chuckles] "... hop on a call with this guy."
And he calls me and he's like, "Have you ever thought about building like an app around Perfectly Imperfect-" Mm. "... where you can share recommendations?"
And it was like the most like goosebump-inducing moment of my life.
I was like, "I'm sitting in the park right now like writing down notes about my future, and someone just called me proposing this, someone I don't even know, that has no idea that I'm going through this moment of change in my life."
And honestly, that was like a big like, I don't know, it was like cosmic shit. I- Yeah. [chuckles] It was kind of... It was a mi- it was a- [chuckles] Alignment. It, it was alignment, yeah.
It was just one of those cosmic moments. And yeah, that, that was kind of an interesting [chuckles] part of the story. But yeah, I spent the next, uh, f- three or four months building Perfectly Imperfect.
Uh, I spent the whole summer of 2023 building it, and we launched the kinda closed beta October 2023- Mm...
and started to invite people and really let people start trying this product, and then we launched it to the full public January 2024.Um, with this, with a really lovely profile in The New York Times. Mm.
And that, that was kind of an explosive moment that we weren't prepared for. We got, like, 20,000 users in the first couple days, and it was, um, it, like, was...
The, the site was so slow and it was, like, crashing all our servers. And that was really exciting. I was like, "Holy shit." I remember exactly where I was when all those users were starting to come in.
Um, and that was really cool, I, you know, to get... see people actually, you know, at scale start to use this thing that I've been building in a vacuum for months. Yeah. Uh, okay.
B- back to the practical bit of, of the s- the scale of the audience and the users.
So when you made that switch, maybe, like, right, right before The New York Times article, which I'm sure brings a lot of people in, how large was the audience?
Um, you can include Instagram and newsletter or separately, whichever makes the most sense to you. I don't remember how many people we had on Instagram at the time.
I w- I wanna say, like, maybe 20 or 30,000 followers, and we had about 30,000 subscribers- Mm... on the newsletter. So not massive.
The, the biggest moment of ex- uh, signups before that was when we did the show with, with Dacre. Mm-hmm. Um, uh, this was, like, our two-year anniversary party. It was our first ever event.
And I had met Harrison through the music scene, and he was... This was kinda during this era where, like, I was meeting all these musicians, and there was like...
Everyone was talking about this MP3 for a song called Girls. And eventually I met Harrison, and he s- he texted me the song, and I was like, "This is a hit right here. Like, this is-" Yeah... "special."
And we were talking about doing a show together, and we kinda threw one of his... He had a, a smaller show before that. Um, but we threw, like, kind of his first- [inaudible] Yeah. Mm.
This was, like, at an art gallery, like, when Girls first came out, and it hadn't went viral yet. I was there, yeah. Yeah. [laughs] It's, it was an amazing moment.
But we had been kind of, like, scheming doing a show together. Uh, and it lined up with our big event. And then we got The New York Times coverage. Uh, and that was, like, the first real moment of virality.
I think we had maybe 14,000 subscribers at the time, and we got, like, 10,000 subscribers in two days. Well, so this... Wait. I, I wanna say something here. So this speaks to, like... This is how you grow.
So, like, for the listener who may not know who Dacre is, right, like, he had... He, he was un- working under another name previously. Summer of 2022 he releases the song Girls. He blows up quite quickly.
A friend of mine, I was watching his Instagram, like, go up, right? And so that was crazy to see that. But then you also experienced the effects of that.
And to be clear, like, Perfectly Imperfect features famous people, not famous people, people in the middle, and I'm assuming that's been, like, 100%...
Not, maybe not 100, I'm exaggerating, but, like, 80% of your audience growth, um, maybe up until the app. The app is still probably part of that.
But, uh, probably a- about 80% of your growth has been from you feature a person, they share it to their own- Yeah... audience on social media, those people sign up. Like, that's how this audience has grown. Yeah.
That's definitely how the growth, uh, the growth engine works is, you know, Perfectly Imperfect has an, a reputation as being this kinda, like, cool, authentic thing to do, um, which is great because, you know, 9 times out of 10 the people we feature will accept the collaborator request and really push it on their stories, and they wanna, you know, they wanna show that they were a part of this thing, and that's been a big part of how we've grown.
Uh, how large is the audience today? I know the Instagram is at 188,000 as of this recording. The total audience? We have about 400,000 people that have signed up for Perfectly Imperfect. Nice.
So quite a, quite a bit larger than when we launched with the app. And the app's been a great way to grow the newsletter as well. They feed each other. Tell me about that flywheel between the app and the editorial. Yeah.
No matter how you enter the world of Perfectly Imperfect now, you're, you know, you can come in through an article, you can come in through, like, the newsletter landing page or someone's user profile or the home screen.
You, you go through the same experience of kind of setting up your profile. Mm. You're subscribing, you're joining, you're adding a photo, you're theming your profile and sharing your first recommendation.
So it's all the same to us, that, you know, you're coming in through this, you know, we feature someone interesting like Elle Fanning or whoever, and now you're getting exposed to this, like, social platform where people are sharing recommendations the same way that the people we feature on the newsletter are sharing recommendations.
And it's all the same funnel. Yeah. Uh, y- you just mentioned Elle Fanning. One more question about the guests.
I imagine that there's probably a lot of these, but m- probably a handful of, like, milestone guests that marked, like, a new
high point in your, like, cultural sway, your ability to attract exciting names, um, probably that als- you, you mentioned all the signups you got after having Dacre on, probably people that also, you know, brought in a lot of new audience.
If you could name, I don't know, three or four significant milestone guests over the lifetime of the project, who are they? So very early on we featured, [laughs] uh, Caroline Calloway. Mm.
And, uh, that was kinda the first, like, big bump we'd seen from a guest.
You know, we got, like, maybe 1,000 new subscribers just from Caroline, and that was like the, the- Who for, for the, for the listener who might not know, she's this sort of niche micro-celebrity, celebrity in New York, the source of controversy, like- [laughs] Yeah, yeah...
It was, it was a while ago, like five years ago now. I don't even know. Yeah. Yeah. It, you know, she...
We ended up featuring her, and it was a really fun one, and she's one of the few guests that we've featured twice just because she's become a friend over the years.
Um, but that was the first, like, moment of some, you know, really seeing a lot of growth from- Like, here's somebody that you know, and, like, wow, now they're in your thing. Exactly, yeah.
And the next one, when I started Perfectly Imperfect, there, there were obviously, like, certain people that I had looked up to for years that I was always pushing for. One of those was Charli XCX.
And the way that one happened is after The New York Times article came out about the Dacre show and all that stuff, I opened my phone the next day and I had a wave emoji from Charli in the PI- Mm...
DMs, and that was, like, a real moment ofOh shit, we're like, we're starting to make it. I'm starting to get my GOATs that I've looked up to for years Yeah And that one was huge. I would say the next one...
This one didn't bring in a lot of subscribers, but like the idea that we had Francis Ford Coppola on Perfectly Imperfect- Yeah...
was just like baffling to me that this is like this like generational legend, and also [laughs] someone that my parents actually know who it is.
But the fact that like just picturing Francis Ford Coppola writing recommendations for Perfectly Imperfect was like pretty mind-blowing to me. That's awesome. Yeah.
And then we followed that up like a week later with The Rizzler [laughs] Which has always been kind of a, you know, part of the Perfectly Imperfect DNA is like, you know- Yeah...
we can feature Francis Ford Coppola and then The Rizzler and then some random podcaster, and it like all works because it's the same format and, you know, taste is, uh, universal.
But those are some of the y- milestone moments. To me too, like the, the, the reason it works is like because it started, there was like...
for so long it was just you and your friends, and like slowly people came into that. So there was this very clear and coherent, like shared culture that you established that other people then like...
That, that's, that's legible to other people. So then a- Francis Ford Coppola can come in, and there's this like legibility of like, "Oh, here's what I'm supposed to give these [laughs] people." You know? Yeah, yeah.
I think that's why it works. I'm sure someone had to explain it to him, but he- [laughs]... he, uh, he definitely like got it. Like his recom- Yeah...
like he had like wearing fun shirts, playing with my kids, and there was a dessert item that I'm forgetting the name of right now that he recommended, but like he, he understood the vibe. Yeah.
I don't know who explained it to him so well, or maybe he was- He's got-... already hip to it. But- He's got hip adult children, m- maybe one of them, or a grandchild. Anyways- Yeah, yeah...
let's, let's talk about the, the business of it for a second, nuts and bolts of how you actually make money. So I know that it's primarily split between paid subscriptions, which are $6 a month, $64 a year.
This is for the editorial and the app. So paid subscriptions, and then limited brand partnerships. Are those the only two ways you are making money? Yeah, those are the only two ways we're making money.
Uh, the brand partnerships actually makes up most of our revenue. Uh, we've done them with Hinge, Arc'teryx, uh, A24. We're about to do one with Ace Hotels. We've done it with Patreon. Mm. Uh, and that's...
You know, we don't do a ton of them. Um, we do maybe one a month. Um, but yeah, the...
we have the brand partnership side of what we do, which is sometimes like, you know, doing a, a, a piece of content with them and then an event or a video, and just letting them have access to our worlds and, you know, building something cool- Yeah...
for them. Um, but yeah, we have subscriptions as well, where a lot of people do it just to support Perfectly Imperfect. But you also get extra theming capabilities on your profile and some power user features.
We're actually about to kind of evolve what subscriptions look like on platform. But those are- Mm... the two ways we make money, yeah.
Can you walk me through like a specific brand partnership, one that happened recently that you thought went really well and like that the audience responded well to?
What's like the, the soup to nuts on how it came to be and what the execution was? Yeah. Hinge, I think Hinge is probably the best case study.
They came to us, and they were, uh, they were interested in confronting the Gen Z loneliness epidemic. Mm. So we came up with this idea of doing a couple... We have this feature on our a- our, our site called an Ask.
It's kinda like Quora where you can ask for a recommendation. So we asked questions to our audience that were like, "How do you get over an awkward situation?" Or like, "What's an interest that led to something new?"
And we got hundreds and hundreds of responses from our community, people telling their stories, paragraphs of, uh, you know, storytelling.
And we packaged that together for a big guide to awkwardness that we did with Hinge, and they did a bunch of out-of-home marketing for it.
And then we did this, um, this video with Rachel Koster, uh, that was kinda like the guide coming to life, and she goes out and actually tries some of the recommendations from the guide.
And then we did this big bowling tournament, which was really cool. Uh, it was at Melody Lanes in Sunset Park, and people came, and we paired them randomly with other people so they could make new friends.
And what was special about that partnership is I went to the, that, that bowling alley about four months later, and just by pure chance, I happened to be next to two people that were wearing the, the bowling jerseys we created for the event.
Wow. And they met at the event. And I was like, "Wow, that, that's like actually amazing that these people [laughs]..." That's the case study, like right there. That's the case study. Exactly.
It's just, you know, helping you form those human connections in a way that, you know, feels true to Perfectly Imperfect and also the brand we're working with.
So I think that's, that's the best case study of a, of a brand partnership. It's kind of the- Yeah... gold standard. On, so on the...
Before we get back to the subscriptions, that is such a good example of what, how I like to define community.
I wrote a piece for Creator Spotlight about like community and events in the creator media world a few months ago, and I used Perfectly Imperfect as an example. But the, like, my conclusion was basically that, you know,
community is this buzzword and brands wanna s- make it, whatever that means. But what it is is like a brand or a publication or a creator, whatever, somebody can throw a party.
But community is when those people come back the next time and then hang out not attached to that party, when they make those connections and like, and then those form. Like, and I think that's why...
That's like a big part of what you've been able to accomplish. But I'd love for you... Maybe I already defined it there, but what does community mean to you in this marketing, media, business, buzzwordy sense? Yeah.
I think there's a lot of different kind of aspects of the Perfectly Imperfect community. There's the social platform- Mm-hmm...
where like people have made like legitimately like amazing friendships just through reading each other's recommendations and bonding on our platform.
So there's, you know, thousands and thousands of people that have formed communities on, on our website and really just become like actual friends, even if they live on the other side of the world from each other.
So that's, that's part of the community.
And then we obviously have like our New York community where we've thrown so many events over the years and, you know, we've built a reputation around specifically our music events, um, where people will just come to them just 'cause, you know, we're throwing them, even if the artist is like relatively unknown.And, you know, those are important parts of communities, and I...
You know, I'll go to these events, and I'll see lots of familiar faces, uh- Mm-hmm... you know, people featured on the newsletter, people that I've met, you know, just through, through these events.
And, you know, I, I think that kind of community's really special, where people, you know, can go to an event and know they'll have some f- friendly faces there, maybe meet someone interesting. Yeah.
So o- on the New York of it all, this is a very New York-centric product. You live in New York. The events are thrown in New York. Now there's, you know, the, the events tool. There's the app.
People are attached to this in various ways all over the world, but I still see this as an aggregator and exporter of a particular brand of, you know, we, we could say Downtown, North Brooklyn, New York culture, right?
This is the DNA, and this is part of why it's successful. You know, you're not the first, uh, publication or brand to, to package and export this. You won't be the last. It's a long lineage.
Um, having said all that- Export sounds too sinister. [laughs] Well, you know, uh, may- maybe it's a bit cynical, but that is what you do. That... I think of- Yeah...
like something like Vice before you, a very different product, but, like, as somebody who grew up in rural Northern California and moved here, like I was a consumer of exported New York culture, and that's why I [chuckles] wanted to move here, right?
Like, it's maybe a bit cynical, but, um, that's what you do. You could say broadcast is maybe a friendlier term. Yeah.
Uh, but, but d- all that being said, besides like people in New York, like more broadly, how do you describe the PI audience today? It's, it's about 70% 18 to 35.
About a couple years ago, we were definitely a lot more New York-centric. Mm-hmm. Probably 50% to 60% of our audience.
Now New York is about 30% of our audience, just because so many people have found us through this app.
And we've started to feature more global, uh, you know, personalities as well, and that's really just expanded the, the vibe of... or just like who is in our world.
When we launched our events feature, we threw 50 meetups on the same day. Yeah.
I basically reached out to the top users in each city that I was interested in, and I said, "Listen, would you like to throw an event for Perfectly Imperfect?"
And every single person I reached out to was like, "Yes, I'd love to." And we had events in Mumbai, Mexico City, São Paulo, London, Berlin, the... Auckland, New Zealand. Like, we really...
It was the first time I was like, "Holy shit," like, "People are sending me photos from across the world of them connecting through Perfectly Imperfect." Mm.
And that was really like a, you know, a moment where I was like, "This is no longer this, like, you know, purely niche New York thing." [laughs] Um, but that... You know, that's definitely a big part of it.
And when we featured all those kind of downtown personalities a few years ago, we still do a lot of that. Um, you know, I was doing it because I thought it was interesting to be a little bit of a portal to- Yeah...
a specific scene. You know, I grew up, uh, about 30, 40 minutes north of Boston in Massachusetts, and I didn't really have a ton of friends who had the same taste as me.
Like, I spent a lot of time online, like reading blogs and, you know, finding forums and, you know, expanding my, my view and my own taste. And I wanted to be...
I wanted Perfectly Imperfect to be that same portal for- Yeah...
for people around the world to kind of get, you know, a look at an emerging scene and what that kind of looks like and feels like in its early days, and I think we did a pretty good job at that. Yeah.
Uh, one thing I, I just realized we never made it back to talking about, um, the health of the paid subscription business today.
You said that the, um, the, the brand partnerships are the majority of your revenue right now, but I know that Business Insider reported in August 2025 that PI had around 2,000 paying subscribers as of July 2025.
Are you able to share a more recent number? Yeah. You know, in 2025 I, I made it so you could bypass our paywall by, uh, re- referring a couple of your friends- Ah... to get more people in the mix.
So, you know, it's, it's grown. Um, but, you know, we've just been trying to get more people on the platform and really have it be this like,
you know, really poppin' place to discover new things with lots of activity, and that requires getting lots of people on the platform. So we spent like the last six months growing rapidly, and- Mm...
we've been, you know, growing 55% month over month. The user growth graph is going straight up. And now we're pivoting back to subscriptions and getting people to, you know, invest in the community- Conversion...
and conversion, et cetera, and really just optimizing all the different parts of that, uh, that flow and just making sure that when you go paid on Perfectly Imperfect, like it's because you want your profile to look sick.
You want it to be this like amazing, uh, you know, online presence, a corner of the internet that feels exactly like you. And that's, that's coming very soon. We just relaunched our app with like...
We built it from the ground up. It's way faster. Wow. It's way smoother. And as part of this, we're gonna have more, uh, you know, power user paywall features. Yeah.
Uh, so there's a lot I still want to get to about the, the, the app and newer editorial, but I want to spend a second on like PI as a business. So right now I know you have a few full-time staff, a few contractors.
How big is the team right now? How many people are full-time, including yourself, and how many other like part-time contractors do you have? [lips smack] Yeah.
We have four full-time, uh, myself, my co-founder, Alex, uh, and we hired one of our best friends from college, TJ, so it's r- it's a really, uh, friend-focused engineering team.
And we also have Lindsay, who handles mot- most of our media operations, uh, with scheduling and booking and outreach and all that stuff. And we also have Vivi Hayes, who's also great.
She does most of our intros and our graphics. And we have Bar, who does brands, uh, brand partnerships and helps with growth. Uh, we... And we have, uh, Kate Weimer, who's our product designer. She's amazing.
And we have several other people that help out in, you know, varying degrees, uh- Mm-hmm... that are more kind of like contracted part-time vibes. But yeah, it's a great team.
Everyone's like super excited about this mission to work on something that feels like, you know, genuinely good in the world in technology, which is like so filled with, at least in my point of view, a bit of doom about-You know, just how inhuman so many products are getting.
What's, like, what's your week-to-week, day-to-day in your current... the current status of your role? I still code a lot. Uh, I, I enjoy programming. Mm-hmm.
It's, it's fun, and I like to, like, have an idea, and actually just, like, hit the keyboard and just, like, make it real.
Um, but you know, it's split between kind of business administrative tasks and, you know, sourcing more brand partnerships, you know, leading our product roadmap, and I'm still the one at the end of the day who's saying yes or no to every Perfectly Imperfect guest.
Yeah. And I've retained that level of curation. Uh, most of it's inbound now. We get, like, 50 or 60 pitches a week. Um- Jeez...
s- so, l- you know, there's a lot of yes, no, and ju- you know, decision-making and scheming, but yeah, that, that's kinda how my week's split up. How far out are you booked? Generally, like, two months, uh- [laughs]...
which is [laughs] it's a lot. We- we're actually about to pivot to being a little bit more selective, um- Hmm...
and running, like, less newsletters just to, you know, retain that, that quality and that kinda stamp of being on Perfectly Imperfect. Yeah.
Uh, so leaving Substack to make your own platform, I'm sure that was really hard. It...
I think you said it was about a year from when you made the decision that, hey, this is something I wanna do, to then actually doing it.
Not to go, like, super in the weeds, but a little bit in the weeds, can you tell me a bit of the- Yeah... I don't know, the grind, blood, sweat, tears of preparing for that?
We were hitting a lot of friction with, like, figuring out how to have monetization on Substack and then also our app and have that be one experience where you can pay and get content, but also app features.
And that was becoming challenging with the, you know, the, the, the split of being on Substack and also having this app. So I was also interested in just having more control of our community and, like, being able to...
You know, like, we, we show content from our social app dynamically onto the newsletter that you receive every day, and doing something like that with Substack was just honestly impossible. Hmm.
And I was also just a little bit frustrated with Substack's lack of, like, distinct, uh, community tools. Y- you have, you basically have one chat box to interface with all of your readers.
I mean, a- admittedly, it's been about a year and a half since we left Substack, so they could have changed that by now.
But I wanted to just build something that, you know, a very distinct way of having our community involved with what we were doing and just kinda owning all that email infrastructure and connecting the dots on subscriptions and, uh, just having it all be one place rather than split between the app and Substack.
So that's, that's how we decided to do it. So there's something here where, you know, you...
part of, part of why you had to leave Substack is 'cause your ambitions and goals outgrew the ambitions and goals of Substack as an app, right?
This relationship between you as a user and this platform, but then you go and you create your own platform, and so now you're no longer just a, a publisher. You, you, you are a platform. Yeah. I'm curious how the...
your sense of responsibility to your public, if you will, changed or didn't change as your public shifted from just readers to not just readers, but also platform users.
Yeah, I think, you know, the relationship definitely changes. The... You know, your, your, your users aren't communicating to you by replying to your n- newsletter and writing you a email.
Y- you know, now our users have a bit of a megaphone, and they have- [laughs]...
like, a real voice, and, you know, they can help us kind of make the community better, the content better, or, like, provide their input on the world that we're building. And I think that part's really cool.
And, you know, since we own this email infrastructure now, we're... Sorry, we're not, we're not using Beehiiv, and we're not using- No, that's okay... Substack or Mailchimp.
We have, like, our own full end-to-end email infrastructure, and we do intend to open that up and let people share list of recommendations to their own audience.
Uh, and that's part of our kinda, like, you know, creator economy play that we're gonna invest- Hmm... in this year, is we already have all this email stuff that we're already using for our guests.
We're gonna give access to our users to also kind of form those communities and have that same email relationship with their readers. Okay, so there's this play to become yet more of a platform. Yeah, definitely.
You know, we wanna keep building. You know, we fully intend to be, like, [laughs] uh, you know, just an, uh, a combination of everything that I've enjoyed on the internet over the last 15 years.
There's elements of Reddit. There's elements of MySpace. There's elements of Tumblr. There's elements of Substack. There's really, you know... I'm trying to build the platform that I've always wanted, and so- Yeah...
I think it, you know, reflects in our users. They're enjoying kinda having this new place that's changing and evolving and shaping...
you know, shifting, but the goals have always been the same, you know, highlighting human tastes and interests.
I don't know if this is still the, the headline when you go on the site, but I know it was a few months ago, to quote, um, "Do you miss the old internet before AI, soulless algo curation, psychopathic CEOs, and slob content took over?
You came to the right place." [laughs] Which is all to say, like, what you're describing in the ambition, there's some tension where the DNA of Perfectly Imperfect is subcultural, which is, like...
You know, you can have a scaled subculture, but there's a limit. So how do you scale it and grow without losing that core subcultural appeal? Cool is extremely subjective, you know?
Like, there will be people who land on the Perfectly Imperfect Instagram page, and they have no idea who any of these people are, and they don't- Yeah. [laughs]... give a shit. And, [laughs]
you know, the editorial side is where we put our... a stake in the ground, and we say, like, "This is the shit we think is cool."
And I think it's cool for a platform to have an editorial voice and, like, a real purpose and, like, be able to platform people that we think are doing cool shit.
But at the end of the day, taste is so subjective, and we built the platform because we wanna help you find tastemakers or interesting people that, you know, match your own individual taste. Mm-hmm.
And allowing, you know, many different Perfectly Imperfects to form on our platform, where people can interview friends or, like, bring them onto the platform, and they can share recommendations.
And then it becomes, like... You know, there's a, there's a PI for everyone on our site.And that's what I've been interested in solving.
I did an interview back in 2022 where someone was like, "Where's your ambitions with all this?" And I said, [chuckles]
I was hinting that Social Platform hadn't existed yet, but I, my- I said my ambitions was to have everyone on... everyone in the entire world to have a Perfectly Imperfect interview. [chuckles] Yeah.
And that's our goal with the, with the platform, is to really just let everyone express their taste and, you know, have that feel, you know, respected and admired by other people. Yeah.
This brings me to something about the Scenes feature. You mentioned that earlier. This is the newest feature. Came out in January. And a line from your release notes here that struck me, I'm gonna read it.
There are no mods on Pi, FYI, but there are editors, and here's the quote, "Editors curate what's worth your time and remove what isn't. They send newsletters soon, write lists soon, host events. They protect the vibe."
So this is, like, a really... This is a real articulation of your platform ambitions. Yeah. Tell me more about this Pi editor user role. [lips smack] Yeah.
We imagine Scenes evolving to a place where there's several editors, and you can interview people, bring them onto the...
You know, like, if you're really interested in, uh, recipes, let's say, and you run the Recipe scene, you can bring someone onto the site to interview them and share a couple recipes and send that out to the scene.
We also have this concept of editor picks where editors can hand-select the best content. Mm-hmm.
We're kind of building this, like, at-scale, human-curated algorithm where all these editors are curating the best content and telling you what to pay attention to and really just owning the vibe of their, their world.
And yeah, that- that's, that's our platform ambitions, is to basically have a million [chuckles] Perfectly Imperfects functioning on the site run by users and editors and curators. Yeah.
It strikes me that, like, the true indicator of your success as a platform, there's like, you know, the proverbial, like, son killing the father to become a man type of thing.
It's, like, what you did in leaving Substack. So, like, what will mark Perfectly Imperfect's suc- success is when somebody, like, builds a platform like that on [chuckles] Perfectly Imperfect- [laughs]...
and then has to leave to start their own. Yeah. [laughs] Like, that will be the sign that you've made it, right? Yeah, I suppose, in a way. Yeah. It's, you know... I, I...
Well, I'll, I'll probably champion that 'cause I did the same thing. You know, but we wanna build...
Like, we're always listening to our users and, like, you know, if people wanna build a specific community on Perfectly Imperfect and monetize that and really have the right community features, we'll build them, whether those are, you know, chat rooms, more embedded events, or just different ways to monetize your content natively on-platform.
We're gonna build the best feature set for you to share recommendations at scale to an audience. Yeah. Uh, you've previously spoken against adding ads to the social app because they could diminish the user experience.
My understanding is that it's quite difficult to maintain a scaled social app without pulling that lever, right?
Do you see this becoming a more difficult decision, or is it that, you know, with some of these platform features you're describing, maybe that's replaced by SaaS revenue?
Yeah, I think there'll be, there'll be elements of SaaS revenue. There'll be elements of creator economy, uh, people monetizing their own audience on-platform, and maybe Pi takes a very small cut of that.
And, uh, you know, I think at scale we'll probably have some version of advertising on Pi that feels native and feels new and different.
But right now we're just really focused on building this out to be a place that is different than the other surfaces on the internet, where everything you're seeing is ultimately just human content and something that someone took the time out of their day to tell you about and share that love.
So you know, I think as we scale, there'll be more ingredients of our revenue from subscriptions, creator economy, uh, affiliate, uh, advertising.
But right now we're focused on the brand partnerships just because they're...
You know, it's a bigger chunk of cash, and we can do something really unique and bespoke that feels true to our world, and it's not super obtrusive to users. They can...
You know, they read the guide, and they actually enjoy it because there's other users' content on that guide. So that's kind of how we're thinking about monetization moving into 2026. That makes sense.
Uh, I'm curious about, like, your set of values, in as much as you can articulate them, and, like, the values that guide everything Perfectly Imperfect puts out.
But the, the best articulation I've been able to find so far is this proper noun phrase I've seen across a few of your personal posts on various social apps, including Pi, which is just, "The internet I remember."
[chuckles] That seems to be your value statement. Yeah. Yeah, I've went between the internet you remember or the internet we were promised. Mm. Which I think the latter is more accurate. Uh, that...
I think we're moving... You know, you spend 10 minutes on Twitter, and you just can feel- [laughs]... uh, the world sh- shape... It's just shifting rapidly, where, like, I don't wanna watch a fucking AI Netflix show.
I don't wanna listen to a song made on Suno. I want to interact with real humans and engage with human art and build a platform where you can connect with other humans. I don't wanna- Yeah...
like, spend time on Multbook or these other- [chuckles]... AI social platforms.
Like, we're quickly navigating to a world that's just, you know, inhuman in a lot of ways, and I do think there's hundreds of millions of people that are gonna really want, like, a, a pure place to hang out and customize their profile and really have a place to be expressive and connect with real people.
And you know, I think the state of the world is, is, you know, quite frankly, like, scary right now. [chuckles] Uh- Yeah...
and I think a lot of our, the big tech social platforms are gonna have a lot of trouble with all the slop content and bots, and they're, they're gonna be flooded with low-quality content, and they already are to a certain degree.
We're in this phase where, like, Brainrot's like, you know, it's kinda funny.
Like, I've obviously sent, like, a funny AI video to a friends, but, like, in two or three years, like, what does it mean when that's all we're interacting with is just, like, these, like... I don't know.
It's just n- It, it loses its footing a bit, uh, once we kind of go out into the, uh, out of the novelty phase and into it's all you see online anymore.
Yeah.This-- So this reminds me, like, I think you've explicitly stated in some interviews I've read that PI is explicitly anti-optimization and pro-friction, and it's kind of what you're describing right now. To me,
I, I think, like, friction is quite literally the source of all life. It's, it's-- everything comes from a f- a moment of friction, um, in a vulgar sense as well, honestly. Uh, th- [laughs] And, and there's like...
I don't know. Uh, maybe it's a difficulty of like, like the, the PI app website, it's dense. It can be hard to look at, it can be hard to use, and this is by design. This is the point.
But part of why the internet has become so optimized is because optimization is how you scale, right? And I'm sure this is something you think about all the time, um, whether or not, like, your stubborn- [laughs]...
lack of optimization. I'm sure there's some things you do optimize, right? Yeah.
But that your, your, your refusal to bend to the op- to, like, product optimization culture, let's say, that poses some barrier to the scale that you need to achieve, right?
Yeah, I think where, like, where I differ from, like, the traditional algorithm sense is that I don't wanna be connected to isolated nodes of content that I have no context on. Yeah.
Like, and I-- the way I've discovered everything and kind of shaped my own taste as an individual is by having certain figures in my life or certain tastemakers, or just interesting people in my world that I'm dynamically finding recommendations from.
You know, we all have people in our life that we share specific song recommendations to or, like, someone you hit up to say, like, "What's a restaurant I should try?"
And that's what we're interested in scaling is, like, helping you find more tastemakers and people like you and communities- Mm-hmm... that you can just, you know, spontaneously discover new things.
If you set yourself up right and you follow the right people, you'll have these kind of amazing aha moments where you'll see a recommendation that could change your life.
You might be exposed to, uh, a new song or a new band that ends up becoming your favorite artist for the next 10 years, and that could spawn from, like, a, a well-written recommendation on Perfectly Imperfect.
And I think that spontaneous discovery is more powerful than the algorithmic discovery of, you know, you're getting just, like, the endless feed of things that you probably will like. But- Yeah...
to really exit your taste bubble and discover something new, it needs to be a bit spontaneous and come from a, you know, a kind of chaotic individual. People have s- No one's taste is algorithmic.
We kind of, you know, we absorb life experience, and that, that shapes our taste. And that's what we're interested in scaling. Yeah, just to challenge us. Yeah. Yeah. I love that. Yeah.
If you listen to only indie rock music, Spotify's never just gonna randomly show you an Ethiopian jazz artist. Yeah. But that might be the genre you've always meant to, to love.
And I think that's kinda the core fault of these algorithms is, like, they're never gonna be too spontaneous because then they can't serve you the right advertisements and blah, blah, blah, blah, blah.
Like, so it's- Yeah... designed to keep you in a box and keep you as your current self. Mm-hmm. Um, okay, back to the editorial. Pivoting a bit here.
Uh, you were saying a little bit ago how, you know, you're, you're booked two months out. It's a little ridiculous. You're gonna get a little bit more picky in how you're choosing guests.
You wanna maintain that level of quality and make sure it still feels like a badge of honor to receive the PI star. Um,
y- in February, over the course of about three weeks, you launched six new columns by, each by a distinct writer. Tell me about this editorial push. Why this? Why these six new columns right now?
Y- We wanted to just offer, uh, you know, more unique voices that are consistent and part of- Mm-hmm... the PI world, people that have, you know, specific flavors of personality.
And I think it's, you know, it's, it's one s- one small step towards a bigger evolution of the editorial brand of Perfectly Imperfect.
Pretty soon we're gonna be launching, uh, digital cover stories where we're gonna do- Hmm... like, a proper photo shoot and a proper interview.
And there's a lot more that we wanna do to just, you know, that's obviously rooted in culture and taste and personality, but there's a lot of different ways to express that in an editorial sense, and some of that will be video, some of that will be adding more contributors who are known for gr- amazing furniture recommendations or skincare or whatever, and having them share on Perfectly Imperfect as well.
So yeah, we're, we're excited about where all this can go.
Uh, Vivi on the Perfectly Imperfect team picked all these editors, uh, kind of emerging writers in New York, and I think the content's been amazing, and they all have, you know, unique visual identity, and they feel very different from one another.
And we're probably gonna add more and more of these. Yeah. Something on the relationship between the app and the editorial here. I'm reminded of Pitchfork and, you know, after, what?
30 years, I think, they've been around. They've recently released this thing where, okay, now it's paywalled to, uh, read, to see the numbers on our reviews, right?
And you could-- If you pay, you can also write your own album reviews, and you can contribute to that culture. And there's a similarity here. They've gotten a lot of backlash around it.
I think for one reason it's because they are owned by a major media comp- company in Condé Nast. Uh, for another, I think that it's... They, they've been free for 30 years, so it's this huge change. And what you're doing
from a, you know, on, on a surface level at least, feels like a much more successful and accessible and palatable to the user base way of doing this. Like, partially because maybe Perfectly Imperfect is about...
could be about anyone. Anybody can be in Perfectly Imperfect, right? And so it's very easy. People... You said people started making their own graphics, and then the, the app is just a logical extension of that.
Um, long setup [laughs] though, uh, for to ask, like, about the im- like, the continued importance of the editorial.
It sounds like you're, you're investing only more in that, and that's only going to become more important, and it's not like you're just gonna shut that down and now we just do the app.
Tell me more about, like, the bets that you're taking and what you're really confident about with the editorial, why it's so important for the future of the company as a whole. Yeah. I, I...
Mean, you're, you're seeing more people talk about the importance of, uh, writers and curation- Mm-hmm... and taste-making as, as we kinda navigate into this, like, this slop future. And I think,
y- you know, the other side of that is that-Starting a new social platform from scratch and having no identity and no distribution is, uh... it's much more challenging. We have this...
I, I like the idea that Perfectly Imperfect has its own editorial voice, and y- you can have like a, a, a framework in your head going into the social platform of what a recommendation looks like and feels like, and kind of, you know, there's a, there's, there's a worldview that's already kind of baked into what we do, and I think that level is important.
And, you know, I also... like less of, you know, taking my business hat off, I just think it's, it's cool to build [laughs] like an a- like an amazing magazine that covers- Yeah...
like, uh, all different subcultures and is a portal into different worlds, and I just think it's fun. It's, you know, it's where we started.
It's a big part of what we do, and it's how a lo- how a lot of people discover the social platform.
And all these different things kind of play into each other in, in fun ways, and we're gonna continue investing in the different pillars of what makes PI a very unique type of business. Mm-hmm.
Uh, speaking of, you know, magazines, what publications, old and new, do you really idolize that are inspiration for the, uh, the current and future iterations of the PI editorial? I think Interview Magazine's a, a...
I think Interview Magazine's one of the, the few- Mm... publications that'll do the Francis Ford Coppola, uh, Rizzler back to back- That's true... type of like high and low.
Feel like they've s- had both of those guys in there. [laughs] Probably. Probably.
I, I think like that's an obvious inspiration, especially when it comes to just like the, the blend of high and low and, uh, you know, documenting interesting people at, in all different creative fields.
That's obviously a big inspiration. So is Pitchfork. I was an avid Pitchfork reader, uh, all through college. It's how I discovered a lot of music and kind of,
you know, went out of my like high school like indie rock stuff and really just built a lot of, uh, you know, just learned a lot more about music.
I didn't have like a cool older brother or anything, and Pitchfork in some ways was my cool older brother.
I've since evolved out of that a bit, and I have, you know, much more dynamic [laughs] taste than the Pitchfork core shit, but it was important to have in my life, and I, I think- Yeah...
that's, uh, you know, that's something that ins- has inspired PI. Also love The Face. The Face does a, you know, pretty similar culture coverage to what Perfectly Imperfect does.
So those are a couple that have, uh, kind of shaped me. Um, so as reported by Business Insider, you have previously raised capital to, I quote, "hire staff, expand into video, and grow the app."
You are starting to raise money for the next evolution of PI. Can you share what you plan to use any incoming capital for? Yeah. We, we need to hire more people. You know, we're a bit restrained on the content side.
We, you know... The... We wanna hire a head of product to really, you know, help refine the Perfectly Imperfect experience.
Right now, it's, it's quite literally just a reflection of my own kind of, uh, neurotic impulses to add a feature or change a button.
Uh, and we want someone to come in and like really help us chisel these ideas down into something that's very intuitive and friendly to use.
So we wanna hire just frankly more people, and, uh, both on the editorial side, but also on the engineering, go-to-market, brand partnerships.
Uh, we just wanna really tell the world about what we're building, and I think there's a huge opportunity here to build the next Tumblr that happens to have- Yeah...
uh, an amazing editorial voice as well, and we fully intend to hit hundreds of millions of users within the next few years. And this capital will help us get there. Yeah. Not to give me like the full...
not to give us the full pitch, but it sounds like that is at the core of the pitch you're bringing to investors, is this sort of to build the next Tumblr sort of platform play. Yeah. Uh, uh, [laughs]
uh, w- in some ways we're an investor's worst nightmare, we're- [laughs] Yeah... we're trying to build Tumblr that's also Vice, and, uh- Exactly... we're coming at it from a t- very different way foundationally.
But we are trying to build businesses of those scale- at those scales, uh, that live in the same ecosystem- Mm-hmm... which is definitely possible, and I believe people are yearning for it. Yeah. Uh, last thing.
You mentioned those, those, uh, digital covers earlier. Is there anything else, both on the editorial and product side, that is coming soon that you can tease?
We haven't locked down the right person yet, but we're, uh... For the digital cover stories, you know, we wanna swing big on the first one, and- Mm... we have...
I, I'm not gonna say names, but we have like a couple like very like iconic, uh, actors that might get involved with this. Um, but I can't, I can't say anything yet. It's, you know, it's not...
The photo shoot hasn't happened yet, and I don't wanna jinx it, but- Yeah... that's... You know, we wanna swing big on that. Um, on the product side, we just launched the new version of the app.
It's much faster, much more intuitive, and you- You said it was recoded from the ground up, right? Yeah. Quite literally over the last coup- two or three weeks. We did it pretty fast. Um, and...
But we still wanna keep refining that.
In terms of a feature, we're about to drop this thing called Taste Match that I think is really exciting, where you'll be able to see how similar your taste is to another person, whether that's your, your significant other or a friend.
You drop it in a group chat. And you'll also be able to see which celebrities we've featured have similar taste to you, so you can, uh, you can discover how compatible you are with, uh, Francis Ford Coppola.
[laughs] Uh, I think this will be fun. It's kinda like, uh, astrology quiz vibes. It's, it's the ingredients of, uh, BuzzFeed in there too. Uh, and just like...
Uh, people love to do quizzes and learn more about compatibility and just get, uh, interesting data points, and we're, we're about to drop that feature next week. Nice.
Uh, is there anything else you wanna bring up before we end it? No, just that I, I do believe that we can build a better internet. Like, I genuinely believe that there can be this amazing human place that...
And p- people really need this right now, and we intend to build that. That... I just hope that comes across in the overall podcast- Mm... is like I am hopeful about the future, even if- Nice...
right now it doesn't feel that way. [laughs] All right. Pi.fyi. Dig it. Pi.fyi. Thank you. Cool. Tyler, thank you. And listener, we will see you next week. [outro music] Hi there. My name's Tom.
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