On making the internet fun again

How did Perfectly Imperfect start?

I started the newsletter back in September 2020 around the time Substack was starting to get a lot more attention. I was starting to see a lot of cool newsletters popping up and it seemed like an interesting way to share taste and perspectives from people. I was fed up with algorithms. Especially during COVID, there was a lot less opportunity to have organic conversations with people about what albums they’ve been listening to or movies they’ve been watching or restaurants they’ve been going to.

I started the newsletter as a way to share some of my own taste. Eventually, we started inviting some friends on, and it snowballed from there. But the goal’s always been to share “a taste of someone’s taste.” We don’t restrain you to media or just products. We look at it as a character portrait where people are sharing little bits of advice or something they found funny or a random link to a website or whatever that might be. It’s very dynamic. It’s a good way to understand someone through a couple of things that make them happy.

There’s something similar in the way that Perfectly Imperfect and The Creative Independent feature people across the board and how every TCI interview ends with five recommendations.

I’m a huge fan of The Creative Independent. I’m interested in this wave of design that is nostalgic, reminiscent of the early web, but looking forward, where it feels fresh and new.

We try to feature a good mix of people across the board, whether it’s a small underground artist or someone super famous like Charli XCX or someone legendary like Francis Ford Coppola. Anyone who moves culture in some way, and culture can be shifted and moved from small underground scenes almost as much as it can be from the most famous people in the world.

What’s your process of getting these people from the big and the small?

At first, it was just sending cold DMs. I had no experience in the media world going into this. I was quite literally just a random guy in Boston. I had no connections to the industry or anything like that, so it took a long time to build up relationships with publicists and build enough of a reputation where we could get access to some of the people we really liked.

When we threw our first big party in New York and we had The Dare perform. He performed “Girls” for the first time to a big crowd. We got written about in The New York Times and it was a pretty viral article. The title was “What the Cool Kids are Into,” so it went negative for bad ways, but also, all press is good press.

The next day, I got a DM from Charli — just a wave emoji. That was pretty incredible. I’ve been a fan of Charli forever and she was one of those Mount Rushmore guests for us when we started the newsletter. Now, it’s a lot of inbounds but it’s still a rough reflection of my taste. We have a couple other people on the team these days but ultimately I’m the one who still says yes or no to who we have on.

Is it you speaking with these guests or do you have a team?

We decided early to do our interviews completely over email. For the photos, we didn’t have money or resources, and since it was during the pandemic, so we couldn’t schedule photo shoots. We thought it’d be fun to just do a selfie, and that’s become the iconic part of Perfectly Imperfect’s graphics style. It’s always funny when you get a real selfie from someone like Francis Ford Coppola where they just propped up their phone. It’s probably the first selfie they’ve taken in years, but it’s cool [and] it feels intimate that way.

It goes back to you saying that it’s reminiscent of the early web—very simple and uncurated. Now, everyone is funneled into a particular algorithm. How are you building a new sort of social media platform through Perfectly Imperfect? I can imagine your relationship with social media being pretty love-hate.

Yeah, it is. The ultimate way I stay tapped in is on social media. So unfortunately, it would be pretty difficult for me to ever delete Instagram, as much as I’d like to.

With the social app, the idea formed from the newsletter format itself. There’s something really special about having those extra layers of customization to express yourself. There’s also something really powerful about the prompt, “What are you into?” It creates this really positive space on our social site where everyone is just sharing things they love and that’s a very unique experience on the internet. We’ve had over 300,000 recommendations shared on the site and I’ve had to take down very little. It’s basically self-moderating where it’s really hard to abuse the format for the wrong reasons.

Every time you visit the site, you might be discovering something new, from someone who’s very passionate about what they like. It’s one of the most positive places on the internet right now.

We need more of those.

The community’s great. People can customize their profiles too, which goes back to what we were talking about, just the early web. Every social site these days just looks the same and there’s very little personalization. We allow you to fully theme your profile. You can add background images, change all the colors, et cetera. People have fun with it. Something that’s a little bit lost on the internet these days is how fun and personalized it used to be.

I remember learning basic HTML through customizing my Neopets profile in the early aughts. What has been the response so far of having the space, people discovering things? Are there social connections happening from this?

Definitely. A lot of people have started dating through the site, which is pretty cool.

It makes sense where you go to someone’s profile and it’s a big picture of them and a bunch of things they like. It’s a great way to get a quick read on someone and start to understand who they are as an individual. A lot of people have become friends through the site. We just launched this Events feature, which is similar to what Facebook Events were in my youth, where you could see a really sick DIY show in the same place that you can see your friend’s birthday party.

To launch Events, we threw about 50 meetups on one day in all different cities across the globe. It’s been cool to see everyone come together and actually become friends and meet in a real space. Ultimately, we use social networks to enrich our real life, whether that’s through recommendations or discovering new things or building new friendships and relationships. That’s the ultimate goal and it’s been really cool to see that come to life through our users.

I feel like PI has an aura of being very New York, so it’s interesting that you’ve been taking it elsewhere.

I just got sent a bunch of photos from the Auckland, New Zealand meetup, which was also cool to see. It looked like a lot of people went to that one, and they booked DJs and had their own cool meetup party that was completely out of our hands. We just let the users organize them and do whatever they’d like.

How does it feel going from you starting this in 2020 as a newsletter and then seeing these photos from Auckland last week?

It’s crazy. Deep down, I believed in this idea since the very beginning, but to actually see it come together like this and have it be my job and have people really connect through it, it’s really special. We’ve been able to get really far while keeping the vision very much still intact. People were a little confused that a newsletter was starting a social network but I just had specific visions.

We’re not just a tech startup being like, “We’re going to build a social network.” There’s already all these newsletters and these events and these parties we’ve thrown and all these people we co-signed by interviewing them. There’s a little bit of an aura that you’re tapping into by going to the site. It already exists, and we have a perspective as the curators, and that creates a really unique community.

Community is something people have been craving because social networks are so antithetical to community. Places like Instagram, which may have started as community sites, have gone more towards selling things. How do you think about community and the importance of it?

The reason why community is so strong on our site is that people aren’t just sharing recommendations for a pair of sneakers or a new Netflix TV show or whatever that might be. People are sharing advice. They’re sharing really personal moments from their life. They’re sharing a distinct memory. They’re laying it out all out on the table. When you have a community of people that are so personal with each other, it forms really unique bonds. I was surprised to hear that a Discord had formed from the people that signed up around the same time on our social site. There’s a couple hundred people in there and they just talk all day. A lot of them live in different places all over the world but they bonded through their experience on this site.

Community can stay online and still be a very productive thing but what we’re trying to do with our Events feature and meetups is try to encourage that people get out and meet each other. One of our most famous users—her username is Taterhole—is the most popular user on the site by a landslide because she’s been such a prolific poster. She’s shared something like 5,000 recommendations.

We flew her out to New York to come to the New York meetup. She has such a great energy to her so it was cool to meet her and everyone. She was basically a celebrity on our site.

That’s such a trip. Has it been cool to see you creating this thing with not that many guardrails and seeing what people do with it and being surprised?

Yeah. There’s one person who wrote a style guide for how to post on PI, and they keep updating this style guide post with new quote, unquote, “rules” for what makes a good post. And some people started doing what’s called an anti-rec, our community’s way of saying, “Don’t try this thing. Don’t go to this restaurant or whatever. Don’t try this experience.” It’s been cool to see. You put this thing out and it’s a blank slate and just watch what people do with it. You watch certain patterns or posting styles or relationships forming in ways that you didn’t expect. When that happens, it’s cool to lean into that and have it be this evolving ecosystem that grows with its community.

You have this sort of shared language. People know what you mean when you say anti-rec.

Exactly. We’re about to lean a little bit more into this community’s angle with this new feature that we’re calling Scenes, which is like our version of Subreddits or Facebook groups where people can congregate around a shared topic. We have no algorithm. It’s just a chronological feed where you can see everything coming in real time. And our hope is that with these Scenes, it’ll be a little easier to find your people on the site and curate your own experience.

What else is in the future for PI?

Things like AMAs will create this fun play between the community and our editorial side of Perfectly Imperfect, where we have a guest come onto the site and answer questions relating to recommendations or advice or whatever that might be. AMAs are going to be really fun, especially where Reddit AMAs used to be this exciting cultural moment when they happen for certain celebrities, but has waned over the years. There’s an appetite for interacting with your favorite musicians or actors, whoever that might be.

We have a pretty small team. We have a couple engineers. We have a couple of people helping out on the newsletter. We newly have an office as of May, so it’s cool to see everyone cooking on all these different parts of what we do. We just started doing a lot more video content on Instagram.

PI is very much a passion project—self-directed, self-funded. What are your anxieties surrounding PI?

There’s always this question of how big can you get while still being, quote, unquote, “cool?” It’s a weird existential thing. It’s trying to stay true to what we believe while also trying to reach as many people as we can and keep things growing just because it’s important to keep the audience growing to keep the train moving with our subscriptions on the business model side of Perfectly Imperfect. It’s about balancing all of that and keep doing things like expanding in a video while still having it feel true to what we do with Perfectly Imperfect.

I’m obsessed with purity. I don’t want to see this thing become compromised or chiseled down to appeal to more people. I like trying to keep it a little weird.** **Our graphics are insane looking. A lot of what we do is maximal, and that’s not always going to appeal to everyone, but I’m hoping that if we keep it moving, then people will come around. It’ll be the PI vibe.

Do you have a sense if you would feel like, “Okay, I’m compromising”? Have you stepped away from anything because of that feeling?

For the first three years, Perfectly Imperfect was a completely free newsletter. We had no subscriptions. It was just something that Alex and I were doing out of a pure love of the game. We just were building this newsletter, putting out three to five a week, doing all these events and everything, just not making a single dime, but spending all this time on it. When we started doing subscriptions, I was worried. I like having things accessible to the most people possible. I was obsessed with keeping it free but when we did subscriptions, it didn’t compromise too much.

The other thing was brand partnerships. We started doing a couple of those. We just did a big one with Hinge. We found the right way to make it feel true to us where we did this guide with them where we asked a few questions to our community around awkwardness and social situations and how you overcome social anxiety or this fear of being awkward. We gathered all this advice from the community and then we compiled it into a guide to awkwardness. As we start doing more brand stuff, there’s a way to do it that’s thoughtful and feels true to us. That’s the mission: to always have it feel like it makes sense within the ecosystem of what we do.