Lessons from A Pirate (Radio), Vol. 2

Video kills the radio star, every time.

In the first volume of this series I wrote about Pirate Radio’s opening act – 31 episodes over the first six weeks of COVID, which connected a tight and wonderful culture that had been dispersed by the upheaval that dispersed and upheaved everything in the world. In Volume 2, we track Pirate Radio’s return after hiatus, in the full splendour of audio and video.

Act 2: BFCM & Beyond

Shopify, being the giant it is in all commerce concerns, has its Superbowl weekend during the retail-resuscitation known as Black Friday and Cyber Monday. Or, as they’re affectionately known inside a company that internally professes an allergy to acronyms, “BFCM”.

BFCM is a massive stress-test of the entire Shopify platform, welcoming a colossal traffic spike during these few days. During the 2023 campaign the platform hit a peak of $4.2M in sales per minute. Shopify basically self-inflicts a DDOS on the entire system, and revels in it. As you might imagine, BFCM was an exciting time inside the company, the way a car race is exciting. You want to see high performance and competition and all those things, but in the dark recesses of your mind a little gremlin is sitting on a fold-out lawn chair with a bag of peanuts and a few cans of flavourless beer. That little gremlin wouldn’t be entirely upset if a car spins out in turn 3 and hits the wall. Nobody wants to see this happen of course … but the possibility of disaster invites drama, and even the most drama-free of us is all about the drama.

And so Shopify would hold this special weekend with tickers measuring sales spinning so quickly you can only manage to count the ten-thousand-dollars column flying by like milliseconds. There are war rooms with arcane graphs and red telephones and stressed-out production engineers with their noses buried in their laptops, not having seen natural light since Thursday afternoon.

It was a real hoot. But the hoot was then, and this was now. Well, this was also then, but a later then. Once work went remote, it was hard to get a feel for that sort of action anymore. The peanut-shucking, beer-guzzling gremlin really didn’t have much to get excited about.

As the first BFCM of COVID rolled around, Pirate Radio had been enjoying a sun-filled summer sojourn, and as November 2020 approached a friend and co-conspirator proposed the idea of an internal radio show for BFCM so I joined her for it.

On Friday, November 27, 2020, Pirate Radio emerged from hiatus like Willy Wonka reopening the gates to his chocolate factory. Instead of being an audio-only stream through a janky Zoom call, there was video. This required many new things of me (including wearing pants) and instead of clicking through Spotify playlists I was properly DJing again. It had been half a year since I’d done the show and as me and my BFCM Radio co-host revelled in Randomness for an hour, I remembered how fun it all was. I was hooked, again.

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Interlude: Inches with Inch

Possibly the greatest part of the entire Pirate Radio experience was a 2-minute segment that aired each episode, with my legendary friend who shares a last name with a very common, non-metric unit of measurement.

Each week, he would measure something. That was it. One thing, in inches.

His cup. A banana. A shoe. The amount his beard grew since last week’s episode.

It was really the moment we all waited for, me especially. If this doesn’t convey the quality of Pirate Radio programming, I don’t know what else possibly could.

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This was the moment I should have had my agent start shopping around for sponsorship deals because the Pirate Radio tide was high. Instead of having an endless supply of AG1 and offering you a discount code at checkout, I ended up becoming Shopify’s DJ for our array of internal events, the pinnacle of which was the company-wide summit in early 2021. With thousands of people around the globe tuning into my set during the pregame show, we nearly took down Slack with a flurry of emojis, GIFs, and every other novel form of expression you see on the internet.

I didn’t realize this at the time, but this moment would be regarded by the employee experience team as a rationalization of steering even harder into all-digital experiences, suggesting that a “Slack dance party” proved that remote work really worked. Drawing this conclusion made me seriously wonder about a number of things, including the fun these folks had ever actually had at a dance party, and how 45 dancing parrots per second flying past a messaging window resembled anything like it.

Well, the remote bookings kept coming in and I kept playing them, somehow also having an entirely other job at the company. In the span of that first year back, I was the hired entertainment at no less than 8 organization-wide remote events. But worry you not; I was never deluded by my brandy glasses filled with green M&Ms and platters of St. Viateur Bagels that I demanded in my performance riders. I always remembered that this insane internal radio enterprise was about creating more connection, and that’s what it remained about.

Being the first at anything rarely means you’re so brilliant and unusual that nobody else would do the thing – it usually just means you were quicker than the other people who were thinking the same thing. Launching an internal radio show at a company wasn’t my idea, it was a just a good idea, and others had their own things afoot. While the opportunity was there to compete like the cutthroat pirate my show suggested I was, the burgeoning new shows actually thrilled me.

And so it was at this point I used my influence to launch and scale the Shopify Radio Network.

Radio Latinx was an opportunity for the Latinx Employee Resource Group to have some fun con sazón and grace us all with much cooler music than we were likely listening to. Bouillabass emerged as a vinyl-and-beer show from a guy who once worked on Shopify’s internal culinary team (yes) and used COVID as a launchpad into a new career inside the company (not DJing, to be clear. Though he does that very well).

A long time ago in a galaxy far, far away, a German immigrant came to Canada and built a snowboard shop on the internet. The tools at the time sucked, and he happened to know how to code, so he built his store from scratch. It turned out that store-building software was more lucrative than selling snowboards, and Shopify was born, facilitating the same commercial experience for others. Both Shopify and myself are – and have always been – facilitators. Developing an internal Shopify Radio Network may not have been quite as profitable as turning an online commerce engine into a publicly traded company, but it got to the heart of what this is all about: creating a platform where more people can express themselves. Facilitating connection.

While dancing around in my basement with loud sound and occasionally having my kids do a little Pirate-Radio-arrrgggghhh sound bite, I had taken a seat at the vanguard of an internal communications empire that our internal communications team had no part in. It was raw, unfiltered, and uncut. Knowing how drama-hungry we all are, I’d like to tell you that this all came to an end when our UFO-sighting show host went insane on the air and started talking about capitalist conspiracies and the secret information embedded in certain Slack channels if you only looked at the first letter of messages sent on odd-numbered minutes and put them together to spell complete words. But this never happened. (There also was no UFO-sighting show on the Shopify Radio Network.) We were a loosely affiliated group with no oversight, massive reach, and did a really good job of fulfilling our mission to connect others through the power and our love of music.

This was the golden era of Pirate Radio. Regularly ending my (and hundreds or thousands) of others’ weeks with a Friday afternoon broadcast of the finest beats and banter on the internet waves.

And then the world started opening back up.

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In the third and final chapter of this tale, I’ll conclude the Pirate Radio saga with a host of lessons that running an unlicensed radio show at a profitable tech company taught me about belonging and connection.

For now: Keep Calm, and Pirate On.