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Grow: How Perfectly Imperfect’s snowball growth started with word of mouth
The Grow interview series is designed to share the nuts and bolts of how writers have gone independent and grown their audiences on Substack. It has been lightly edited for length and clarity.
We invited, the co-founder and writer of , to offer his insights on reinventing the recommendations profile, the subscribe factor of Comic Sans, and going viral after being featured in the New York Times.
Tyler juggles running Perfectly Imperfect with his day job as a software engineer, along with his editor and co-founder,. He says they had no credentials or contacts before starting the passion project during the 2020 Covid lockdown, but, by featuring the tastes of “if you know, you know” creatives in New York City, they’ve built a community of tens of thousands.
What’s your Substack about in one sentence? is a newsletter that shares “a taste of someone’s taste” a few times a week.
Who reads your publication?
People searching for what’s next and what they may have missed. People interested in culture, eclectic personalities, art, and downtown New York City. People craving discovery.
What do you uniquely offer readers?
We do recommendations a bit differently at Perfectly Imperfect. Rather than being a vessel for online shopping and media consumption, I like to think of our format as an unconventional profile that offers an intimate glimpse at what someone is like and what someone likes. We feature up-and-coming creatives as well as people like Charli XCX, Michael Imperioli, Lena Dunham, Mac DeMarco, Bowen Yang, and Mel Ottenberg.
What’s your content strategy?
Schedule: Ideally we’d just post every Tuesday and Thursday, but I’m not perfect and occasionally book too many guests, so some weeks have posts on Monday, Wednesday, and Friday.
Social media: Each post goes out on Substack around 10 a.m., and after that we promptly share a custom graphic on our Instagram page.
Format: Most of our posts are formatted exactly the same and contain a brief intro, a banner graphic, and 5 to 10 recommendations. Any post that’s not the standard guest format is probably promoting an upcoming party, recapping a previous party, or sharing other miscellaneous pieces of content, like playlists and merch.
Growth by the numbers:
Started Substack: September 2020
Total subscribers: Over 30,000
We had absolutely zero industry credentials or online presence. The newsletter’s early guests were all close friends of mine, and over two and a half years it’s snowballed into booking guests, getting profiled in the New York Times, and throwing official music showcases at SXSW. Still hard to believe.
We had absolutely zero industry credentials or online presence. The newsletter’s early guests were all close friends of mine, and over two and a half years it’s snowballed.
Meaningful growth moments
Getting started: It was peak Covid, and I was longing for an exciting side project to sink my teeth into. Around that time, I discoveredthrough some fashion communities I was lurking in, and it inspired me to start a Substack of my own. Our format has remained virtually unchanged since day one, but the vision and scope of the project has morphed a bit.
By this point, Perfectly Imperfect was starting to grow beyond friends of mine and we were starting to tap into some New York City characters such as Chris Black, Rachel Seville Tashjian, The Ion Pack, Lauren Servideo, and The Drunken Canal. However, our first big guest was Caroline Calloway, and her feature got us nearly 500 subscribers in a single day.
In January 2022 we were profiled in Vanity Fair, which really legitimized our whole operation and brought us nearly 800 new subscribers. It was a lovely piece, and I’m really happy with how it came out. I felt that Delia [Cai] perfectly distilled what makes our newsletter special and not just your average recommendation vehicle.
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, A. 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, haha. However, all press is good press, because we got over 10,000 subscribers in a single day.
Today: My main goal is to keep exploring what Perfectly Imperfect can be. We’re throwing an official showcase at SXSW, planning more events/parties this spring, potentially starting a record label, and trying to keep booking cool guests.
How does your Substack fit into the rest of your professional lives?
Not well, haha. Admittedly, it’s becoming increasingly difficult to balance the huge workload of this newsletter with my actual full-time day job as a software engineer. However, I’ve been able to merge the two skill sets by building this recommendation search tool and a Discord bot (both are currently broken…).
Do you have plans to go paid?
Maybe someday. Coordinating two to three guests a week and planning events/parties is a crazy amount of work, and it’s by far the thing I’m most passionate about, so it’d be great to make it my full-time gig someday.
I guess I just like the idea that anyone can stumble upon our site and read it, free of charge. I feel like there used to be so many high-quality free blogs on the internet and they’ve all disappeared or are paywalled, but maybe we just look at that era with rose-colored glasses and they were actually making from the plethora of ugly ads. It’s hard to say. If (when) we inevitably go paid, I just don’t want it to feel different and limit too much access.
How do you see the newsletter working alongside other platforms, for example your Instagram, Discord, and in-person events?
Our Instagram is the primary portal to our world. Not only does it act as a gallery of who we’ve featured and allow people to easily share our posts, but most of our guests (such as Anthony Fantano and Debby Ryan) end up keeping our graphics in their own feeds. The thinking is that you’re probably going to hit subscribe if you see our blue background, yellow stars, and Comic Sans enough times.
Events have been a really fun addition to what we do. So far, we’ve built a great reputation for throwing raucous parties with epic live performances and killer DJ sets, so hundreds of people show up each time. The SXSW show is a glimpse at what the future of Perfectly Imperfect may look like: larger-scale curated showcases of the sounds of tomorrow.
How do you balance growth against remaining cool?
What makes Perfectly Imperfect special is that the vast majority of people we feature are smaller, “if you know, you know” creatives in New York City, so the larger we get, the more we can help give these people a larger platform. There’ll probably be a point in the next few years where it’ll no longer be “cool” to do a Perfectly Imperfect feature, but that’s okay because nothing lasts forever :)
What about algorithmically-driven recommendations?
I wanted Perfectly Imperfect to be an antidote to everything getting homogenized by Spotify playlists, Netflix suggestions, and social media, and help people discover new things outside of their bubble. I think there’s a real lack of pure and honest curation from regular human beings, not algorithms, referral-link-laced listicles, or “influencers.”
You told Vanity Fair you think of each post as a “character portrait.” How did you devise the format?
The first sentence of every post is “Cool people like cool things, which is why we asked __ to share a taste of their taste on Perfectly Imperfect,” and it’s remained unchanged since the very beginning. That’s because we strongly believe in handing over the microphone to other people. Sure, I think I have decent taste in music and some other stuff, but it wouldn’t be as fun if it was just me multiple times a week.
We strongly believe in handing over the microphone to other people. Sure, I think I have decent taste in music and some other stuff, but it wouldn’t be as fun if it was just me multiple times a week.
What is the sharpest piece of advice you can offer other writers about growing a Substack publication?
Never give up! Sure, I know that sounds a bit corny, but it’s true. For the first three months or so, we saw almost zero growth and had very few “wins” to celebrate. You have to have real grit to make it through the periods where you wonder if it’s even worth it.
It’s also really important to think deeply about how people will discover your publication. Are you, or others, sharing your posts outside of Substack? Or are other Substacks recommending yours? Those are the two main ways people will stumble upon your newsletter; otherwise no one is going to find what you’re working so hard on!
Who’s another Substack writer you’ve turned to for guidance or inspiration?
I’m a big fan of what my friendis doing with . I think we have similar goals, and I love his “boots on the ground” approach to music scene coverage. Go, Joe.
Stay true to your values: Tyler and his co-founder wanted to give over the mic to other people to share their recommendations. They’ve stayed true to this concept and format since the outset, as it became integral to the Perfectly Imperfect brand.
Think about discovery early: Perfectly Imperfect creates eye-catching graphics for Instagram as its main first-touch platform.
Don’t give up: Perfectly Imperfect started as friends sharing their cool taste with more friends. Keeping at it required “real grit” before they saw any growth. Then it skyrocketed.
What questions do you have for Tyler that we didn’t ask? Leave them in the comments!
To read more from this series on growing your publication, see our interviews with Melinda Wenner Moyer, Leslie Stephens, Becky Malinsky, Tim Casperson, Marlee Grace, Gergely Orosz, Anne Kadet, Category Pirates, BowTiedBull, Justin Gage, Noah Smith, Carissa Potter, Jørgen Veisdal, Anne Byrn, Nishant Jain, Michael Fritzell, Glenn Loury, Erik Hoel, Jessica DeFino, Mike Sowden, Elizabeth Held, Jonathan Nunn, Polina Pompliano, Michael Williams, Judd Legum, and Caroline Chambers.
If you’re inspired by Tyler and want to start your own Substack, you can get started here: