Use an emdash

In which I nervously wade into Emdash Discourse and say goodbye to Substack

May 09, 2025

I am extrovert-low-neuroticism-presenting, but it is probably no surprise to most close friends that I am a deeply melodramatic person. Many many years ago, I wrote my University Valedictorian speech while listening to Lorde’s “Melodrama” top to bottom over and over again. Two weeks ago, I posted a video of me learning “Liability” by Lorde on the piano, and tweeted something like “I can’t enter a new phase of life until Lorde drops a new album”. She apparently wants my body really badly, and a few days later she dropped “What Was That”, her first song in four years, a reflection on her early twenties, and presumably an attempt to call my bluff.

Since then, in the last two weeks, I: turned 30, quit my job, got hospitalized, threw the greatest party of my life, pulled an all nighter at the aforementioned party and then got straight on to a plane to SF, immediately flew to Mexico for a weeklong bachelor party after that, and now I’m here. Baby, truly, what was that? After fourteen days in a stupor, I wrote this goodbye essay to the Substack internal company blog in an attempt to unpack my last five years, in which I also happened to be in a stupor. I mostly could not have written a more perfect job for the Shaiyan I was five years ago—spending my days working with creatives of all stripes, building a social network from scratch, learning from some of the sharpest media minds in the world.

But: Muss es sein? Es muss sein.

I joined Substack almost five years ago—and then we immediately had our first PR crisis.

Before we were accused of being Nazis, before we were bad for democracy, we tiptoed into the pisswarm waters of controversy with something far more insidious: using the CC field instead of the BCC field for a mass email blast.

My first few weeks here were hazy. It was the first Summer of COVID, everyone was either social distancing or becoming irreversibly radicalized in a hundred different ways, and while the entire company was in SF I was the sole remote Substacker out of a Canadian village called Toronto. There was no such concept of “training” or “HR”, and within a few hours of getting a company email address I was off to the races emailing writers to try their luck at a paid newsletter.

Not pictured: me wondering why no one else was on the company Zoom meeting

It was weird. I insisted on coming onboard part-time because I wanted space to work on something of my own (lol), but very quickly realized this was the sort of once in a lifetime place that I just had to go all-in on. And all-in indeed I went. I remember being surprised at the lack of oversight, and in the absence of any rules, as I tend to, just defaulting to all the most insane things I could: planting reply-Tweets from my burner accounts (“Have you heard of this Substack thing?”) and then slamming writers inboxes with my real name a week later (“what a synchronicity…”), scraping lists of folks who had been cancelled so we could house them from the hordes, and generally reaching out to whoever I pleased (sorry for the templated emails, Obama).

And then, suddenly and hilariously, we were an email company in the middle of our first controversy about incorrectly sending emails.

I remember getting an email from Hamish, one of the cofounders—I wasn’t even a part of our Slack at the time, I don’t think!—urgently asking to see the copy that I had been sending out to writers. I thought my email was pretty good; I had already gotten replies from public figures like Robert Reich, and in my hubris I thought he was trying to get inspiration from my email templates as the company’s one “sales guy”. My outreach began with something like: “I’m a writer and an early member of the team at a startup called Substack - we make it simple to start a paid newsletter”. But Hamish, my Sun, and I, his Prince with wax wings, were not on the same page.

“If we’re going to call ourselves writers, we need to show that it is true. Fix your punctuation. Don’t use a hyphen where you should be using an emdash.”

I genuinely and viscerally remember thinking that this was loser behaviour. I truly had never heard of an emdash, and frankly would love one of you to edit this post because I mostly still don’t know how to use one. At the time I was cranking out something like 40 cold outbound emails a day, and I remember being frustrated at how often I had to use a keyboard shortcut to access this new punctuation mark, this hyphen that he had stretched out and nonconsensually tied around my ankles. I wanted speed, and he wanted precision.

I’m chuckling as I write this, because it was truly nothing more than offhand feedback and he almost certainly doesn’t remember the interaction. But it’s jarring how often I think about it. It felt like a good encapsulation of a lot of feelings I had at the time, and many feelings I’ve had since: feeling out of place at a company so clearly destined for greatness, feeling self conscious to be around such incomprehensibly brilliant thinkers and writers, and discomfort around an almost righteous obsession with building things the right way.

But there are emdashes everywhere for those with eyes to see.

It’s insane to think about some of the swings we’ve taken the last few years. Paying writers upfront with Pro deals so they could quit their jobs and go all-in on themselves, because we were so confident that they would be better off by going independent. Building a new social network from scratch because it didn’t sit right with us that creators had to drink from polluted water sources just to build an audience. Defending free speech before it was in vogue.

But we’re on a tightrope, and there’s a tenuous link holding this bad boy together. These writers and creators and podcasters and readers have something in common: they trust that we’re the Good Guys. That we’re morally and financially aligned to fix a media ecosystem that has been broken and toothless for as long as I can remember. That we’re one of them.

I’d like to say that by now we’ve earned their trust, but it’s really not enough. We have to remember that we're working with people that have readily given out this trust before, and they’ve been burnt time and time again. We have to win that trust again every single day. Every interaction—every support ticket, every late night call soothing a creator, every early morning oncall putting out a fire, every punctuation mark in an email—is a both a representation of and a vote towards the Substack universe that we want to build. Using their language matters—it’s why we don’t refer to people on Substack with the drug-addled colloquialism of “users”, and it’s why it took us so long to switch from using "publishers” to “creators”. Understanding their businesses matters—it’s why we were so meticulous about understanding RSS feeds and dynamic ads and baked-in ads and all the rest of the gnarly podcast world when we first stretched beyond writing. Understanding their personas matters—video is incredible for so many people and we’re doing an incredible job of building it, but some writers will just love to write and Substack should still feel like their home. It’s on us—or, perhaps more accurately, it’s on you, since it hasn’t yet hit me that I’ve so recently removed myself from this equation—to carry this weight in every single decision and indecision, and action and interaction, that happens here from here on out. It is no small game to build a new media ecosystem from scratch: there are livelihoods and mindviruses and romances and friendships all hanging in the balance of this tight rope we have so meticulously crafted together.

It is unfamothably heartbreaking to be leaving Substack, but I feel so lucky to have gone on this journey with friends. I can’t wait to see the universe you all will build together, emdash by emdash.

Thank you for humouring me with this navel gazing post. I will now subject you to gaze into my navel once more with a final trip down memory lane—here’s a smattering of random memories during my time here, in no particular order:

SALES AND WRITERS

I am forever grateful for Hamish and his Twitter fingers. I cold emailed him, we chatted back and forth for a few months, and eventually I came on board. I remember being so afraid that he would think that I was a “sales guy” that I showed up to our first call wearing a headband and frosted blonde tips so I would look “approachable” and “like I was from San Francisco”.

I’m sorry this is literally the only screenshot I have from this era of my life

SORRY I HAVE AN INCOMING CALL

I spent about a year working with a writer who I respect, an older gentleman who shall not be named, who just so happened to very clearly be in a romantic relationship with his assistant. They would always call in together from the most extravagant locations, always from the same Zoom device. One day we had a scheduled call to show him some new tools, and for the first time they appeared on different Zooms. I didn’t think much of it, aside from the fact that I knew he was terrible with technology and usually she was a huge help in getting him set up etc etc. We’re about five minutes into a thirty minute call, and I ask him to share his screen so I can show him exactly how to use the tool. He’s obviously struggling with it, but eventually gets his screen live. We’re poking around for a bit, and he suddenly clicks off screen. I gently ask him to flip back to the last screen we were on, but he accidentally clicks back to his WhatsApp Desktop screen instead of his Substack screen, where he has his conversation open with this woman, with full frontal nudes of each other. I immediately look down and say “I think I have an oncoming call”, while these two poor lovers try to slowly slide the browser tab away, because in the heat of the moment he can’t figure out how to shut off the screen share. I look back up after a few minutes, and we finished the next twenty minutes of the call without mentioning it.
HOT SINGLES TORONTO

February 2021 and the entire world was opening back up after COVID—except Canada. There was a hot new Substack called “Hot Singles NYC”, and I wanted to try a version for Toronto and kinda run a prank on a friend who had been single for a while. I whipped up Hot Singles Toronto in a day, made a profile for him and a few other friends to make it seem real, emailed a bunch of local publications, and went relatively viral. I thought nothing of it.

The next morning I wake up to an email from someone named “Randa Sakallah” accusing me of “plagiarizing”, which was “especially ridiculous” to see from a “Substack employee”. I freaked out, deleted the publication, apologized to her for her valid complaints, and, again, thought nothing of it.

The next day I had a regularly scheduled 1:1 with Fiona, and a minute before we met, I saw Hamish get added to the invite. I remember my heart dropping before I popped into the Zoom. He was, rightfully, furious. “You’re so lucky we’re not firing you right now man”

Many years later when Randa joined the team, we were doing introductions in a team meeting and when I went up, she goes, “yeah man, we’ve already met”.

I’m still plagiarizing her to this day. What’re you gonna do Randa? Ask Hamish to fire me???

CHEST HAIR

For at least 2 years there was a running joke where Jairaj and I would get our shirts ripped off at company parties. Notice how he doesn’t wear button ups to company parties anymore…

SWEATY GANG

We all know that Sophia is a magician, and within 24 hours of joining Substack she was already on a call with Roxane Gay, convincing her to join Substack. What fewer people know is that Sophia is not good at Slack. She immediately posted a message in the #general channel, saying something like “oh my god fiona I’m so sweaty, I just got off the call with Roxane”. I messaged her immediately telling her it was the wrong channel, and that I also sweat profusely on writer calls. Our standing 1:1 was called “Sweaty Gang” for many years afterwards. When Zoe started interviewing here, our sweet sweaty angel, she and I joked about it on our very first call together, and so the Sweaty Gang became 3.
HELPFUL BROWN NAZI

BARPod calling me their “Helpful Brown Nazi” on a podcast once during a Substack free speech PR crisis
THANK YOU FOR HUBSPOT

I will always respect Hamish for many things, but I unironically especially respect his ability to show words of affirmation through thick and thin. I remember being shitfaced with him and a small late night crew at our first Summerfest, exploring SF looking for something to do, when the two of us got lost from the group and ended up in a random Karoake bar together. We’re singing and dancing and he turns to me with drunk words of affirmations: “It’s so fucking special what everyone is bringing to the team. Dan brought us Patti Smith. Sophia brought us Roxane Gay. And you brought us [stutters for a second, thinking] Hubspot”.

hubspot they’re gonna kill you when I’m gone :(
RAW

At a 2022 Summerfest, we all went to a Chinese restaurant for dinner, and then immediately to a bar. Zoe, never one to waste food, brought her leftovers with her. We were all many many drinks deep, as one tends to be at a Substack party, and Zoe ended up leaving her food at the bar. I brought the food home with me so I could chuck it in the fridge and give it to her the next day. But unfortunately I got home and went gremlin mode. I got hungry, and with no utensils in my hotel room and very little sobriety/morality left, I sat alone in my hotel room, lights off, eating Zoe’s noodles with my bare hands. I told her the story the next day, and I think I phrased it as “I rawdogged those noodles last night”, several years before the phrase was in vogue. Our sweet angel was appalled.
HALLOWEEN 2021 DRESSED AS THE FOUNDERS (WE WON THE COMPANY COSTUME COMPETITION)

BEFORE I WAS A SHITPOSTING ON NOTES I WOULD JUST SEND STUFF LIKE THIS IN SLACK DMs

(Found this from 2022 sorry this was too good to not post)

THIS RANDOM SCREENSHOT I FOUND IN MY “SUBSTACK MEMORIES” FOLDER FROM 2023 TITLED “THE KINDA LOOKS LIKE SACHIN”

KEV AND I UNSURPRISINGLY FINDING OUT WE WERE BOTH STUDENT COUNCIL KIDS / LIVED THE SAME CHILDHOOD

SEX RESEARCHER

We had just added our first (and only, so far), cohort of “A&D Associates” to our recruiting team—Bailey, Shenel, and Randa. We were going on our first retreat as a team together, and all wanted to be on our best behaviour to leave a good impression on the younguns. One night we’re hanging out on a rooftop after a long day of drinking and exploring Upstate NY, and one of the Associates asks about [SEX WRITER] I tried giving a gentle politically correct answer, something like “She’s a sex researcher”. Clyde immediately follows up with “Yeah, she’s a sex researcher in the same way I’m a masturbation researcher”
WHEN I COINED THE TERM “LINDAWG” (RIP)

SKRIV TEX HAR / MAGIC MIKE

Summer 2022, I think? Kerianne, Zoe, Katie, Mike, and I didn’t feel like going out with the company for drinks so we thought we would just have a chill glass of wine at the office and then head home. And then Mike started playing Magic Mike videos, and just took over the “dance floor” (All Hands Space). We drank so much wine that we had to take the bottles out at night, because we were embarassed that Chloe might find them and ask wtf we did that night. Mike was just recovering from a torn achilles and mf was throwing so much ass we unironically asked him to stop and take it easy
FEET