Five Years of Perfectly Imperfect

On this day five years ago, we dropped the first Perfectly Imperfect post.

Truly crazy to think about. This is the longest I've stuck with any project or job, and it's gone way further than I could have ever dreamed. In that time I've moved cities, married the love of my life, got laid off, and met thousands of people.

To celebrate five years, I wanted to tell the story of PI.

How it started and where it's all going.

Perfectly Imperfect Newsletter (2020)

An old graphic describing PI (November 2020)

It was peak COVID Summer, I was living in Somerville Massachusetts, and Alex and I had boring 9-to-5 jobs. I was growing frustrated with algorithms starting to define everyone's tastes (mine included) and this feeling was only exacerbated by being cooped up at home during the pandemic.

The idea was a newsletter that championed human curation, and I'd had the name "Perfectly Imperfect" written down in my notes app for years. I've always enjoyed art that's rough around the edges, full of texture, and ambitious. Like The Microphone's 2001 album, The Glow Pt2, or Vincent Gallo's Buffalo 66. My favorite things are Perfectly Imperfect.

We described our simple format as "A Taste of Someone's Taste" and started interviewing friends while occasionally sharing some recs ourselves. It was different than most recommendation resources in that we didn't restrict people to just products or just media. People shared life tips, inside jokes, their favorite place to take a walk, etc. It was more of a character portrait than a purely practical list.

An early graphic ft Emily Sundberg's recommendations (October 2020)

That's basically how Perfectly Imperfect was born. Neither of us had any experience in the editorial world, zero design skills, and no industry connections to the people we wanted to feature. It was (and still is) a very scrappy lo-fi operation.

It took us almost a year to hit 1,000 subscribers, but we slowly started to build credibility and a dedicated audience who fucked with the vibe. The cold DMs increasingly got a "yes" response, eventually leading to guests like Charli XCX, John Cale, Olivia Rodrigo, and all-time favorites of mine such as Bill Callahan and Lorde.

Screenshot of our Instagram feed (September 2025)

On October 22, 2022, we threw a party at Baby’s All Right in Brooklyn to celebrate two years of Perfectly Imperfect. The party featured live performances from The Dare, Frost Children, and LUCY, and DJ sets from The Hellp, Umru, Harmony Tividad, Andrew Savage, and Julian Ribeiro.

Our party got covered by the New York Times in a piece that went semi-viral on Twitter (mostly because the title inspired a lot of … strong opinions). It was my first taste of that kind of attention, and I didn’t like it very much. However, all press is good press, because we got over 10,000 subscribers in a single day.

Eventually we left Substack to start our own website, but you can read more about that here.

Today, we have 150,000 subscribers, and we've shared over 600 interviews, thrown 50 events, expanded into other content styles, and most notably - built**** a social network.

PI.FYI (2023)

At some point I had a galaxy brain moment about our "recommendation" format.

The simplicity was powerful — an emoji, title, a few sentences, and maybe a link or image. It's the perfect posting format. Easy to skim while being dense with personal perspective.

I was interested in this idea that a magazine could also be social. Rather than always being curated from the top down by "tastemakers," this could be a place for everyone to share what they love. Right alongside our editorial content.

Early hand drawn mock-up for PI.fyi (June 2023)

So when I got laid off from my day job in May 2023, I set out to build a place for our readers to share their tastes with each other. Heavily inspired by the kind of websites I remember using growing up - places where the purpose wasn't clout or influence, where the whole point was connecting over your shared interests.

This concept became PI.FYI, and in January 2024 we released it to the public after 6 months of heads-down coding. Lots of oatmeal, coffee, and long days.

We worked with Special Offer on the design, and a year later they did Charli XCX's viral Brat album campaign. We wanted the site to feel reminiscent of the early web, but not overly nostalgic. Vibrant colors, customization options, squared off edges, bold uppercase text, and so on. It calls back to an era where algorithms didn't dominate your day-to-day experience on the Internet.

Screenshot of the Pi.FYI homepage (September 2025)

It's come a long way since 2024. It's much faster + less buggy, there are 80,517 users (growing 500+ a day), and we've launched a lot of new features.

We dropped our Events platform on PI.FYI back in August, and this weekend there'll be 50+ user organized meetups happening all over the world. We had the NYC meet-up last weekend and it was so lovely talking to everyone. A lot of new friendships were born in that room. You can see if there's one in your city here.

What's next?

Some of the team in the PI office (August 2025)

Things have changed a lot in some ways, and very little in others. The mission is still exactly the same - embrace curation and celebrate the people who shape culture.

We have a lot of fun things coming up that I wanted to tease : )

Fakemink live in NYC (9.13)

Unfortunately, this is a fully private event.

However...if you reply to this Ask on the site we might give you a free ticket.

We're cooking up a new feature for PI.FYI called "Scenes." You can think of it as somewhere between a Subreddit and FB Group. A place to find like-minded people and discover new things.

This is going to be a big one and it'll launch in October.

Soon you'll be able to run an AMA on the site. Any user can create one + we'll also be running live interviews with your favorites, where they'll answer your burning recommendation-adjacent questions.

We just started running a new video series called "Taste Test" where we hand curate "Asks" from our site and ask them to talent. It's a lot of fun and we kicked it off with Water From Your Eyes. In the next few weeks expect to see interviews with Frost Children, Bar Italia, and more.

Aftertaste

Our brand new party coverage column. Instead of generic photo coverage, we're also asking people for 3 recommendations. It's a cool way to capture the "feeling" of what it was like in the room. Who was there and what are they into.

Thanks for reading.

I'm so extremely thankful that you guys give a shit about Perfectly Imperfect. Stick with your idea and deeply believe in it. Everything will work out.

The next five years will be even better.

Tyler