The year was 2020.
… and you know what happened.
What you may not know as well is that for 2.5 years I’d been working in paradise. Not only at the fast-growing, highly profitable Shopify which had a remarkable bent toward “over-optimizing the employee experience,” as I once heard CEO Tobi Lütke say, but at the very best office in this fast-growing, highly-profitable, employee-experience-over-optimized business.
That’s right. In a converted whiskey distillery (2010s tech office, obvs) in Waterloo, Canada, we had the best of it all. As you just read in that last sentence: a converted whiskey distillery. While that did not mean whiskey abounded, it did mean we ate lunch in a room latticed with the most stunning wood structure that once held casks of whiskey. Oh yes, and as you just read in the last sentence: we ate lunch in this space because we were given lunch to eat in this space. And that really just scratches the surface.
Above all, there was a magical dynamic in that office that had to do with its size (~175 ppl) and the generally relaxed & unpretentious attitude of people living in Kitchener-Waterloo. The result is much like in Cheers, it was a place where everybody knew your name.
This came to a crashing halt when that thing happened in 2020 that forced us all into hermitage (other than those brave souls who it didn’t force into hermitage, but hey, our work involved typing and talking into screens. Activities well suited for hermitage). Major parts of our lives were turned upside down, and in this case, the work community we had at Shopify – and particularly in Waterloo – was something I wanted to save.
Act 1: Enter Pirate Radio
The first eerie Monday after we’d been ordered to home-from-work I spun up a Zoom call with an idea that I wasn’t sure anyone would care for, and with the hope that nobody would unmute and just start talking in the middle: I’d play music.
And it was a hit.
In fact, here’s the Spotify list with the very first episode, dated March 16, 2020.
It was a crazy idea and its success tells the story of the company at the time: a fabulous, connected culture, a good sense of humour, care, connection. I focused on playing requests from other times in peoples’ lives as way to create some comfort during a disorienting moment.
At its peak, there were ~150 people tuning in each day (that’s right, I did this daily) including President Harley Finkelstein and then-Chief Talent Officer Britt Forsyth, and let’s get off the celebrity bandwagon here – a ton of cool people were tuning in constantly and their DMs expressing deep gratitude kept filling my tank with very real fuel.
As I mentioned, I was doing this every eastern-time-zone-morning and then transitioning into the rest of my job. Despite the gratitude-fuel, it became exhausting. After six weeks I was feeling drained and it also seemed that communities had started to (re-)establish themselves. After the episode on April 10th, 2020 – 31 episodes in – and playing a key role during a hard transition, Pirate Radio took its first hiatus.
Let’s pause the tale here because in this first meander of Pirate Radio grandeur, there are some important lessons to glean, and you probably have work to do anyway, and want to get to the end of this damn blog post.
Lesson 1: The Connective Voice
Radio has this strange power. Apparently video killed its star, but the thing is still going. Streaming seems like it should have killed it again, but the thing is still going. Spotify has started experimenting with this DJ feature which uses a synthesized voice to be your own AI-DJ, which I find kind of strange and have been trying to delete but Spotify conveniently doesn’t let you do that with their new, experimental feature.
Anyway, where was I. Ah yes, the power of radio. There’s something strange and magical about turning this thing on, and there’s a voice (or likely an ad for mattress discounts) that’s been there the whole time, and you’re getting to listen to, along with a whole bunch of other people you can’t see.
I don’t know where its magic lies, but my banter on Pirate Radio provided something crucial and human, at a time when we’d all been pulled apart. Actually, for the first few episodes I didn’t say anything. I didn’t think people wanted to hear me talking over the music especially if it was a background to their work, and it made me a little bit nervous. It requires a person to speak compellingly while facing a wall, knowing some uncertain number of people are out there listening, not able to read reactions or feel any energetic feedback … the whole thing is strange.
Strange, but powerful.
Speaking to a group all at once isn’t just powerful because of the content being communicated. That’s probably a distant second, and my tendency to ramble on 7th-order tangents clearly demonstrate that what’s being said isn’t all that important. What really counts is that people know that people like them are listening to the same thing right now, and in some magical, invisible way, we’re connected.
It might not be enough to keep a person warm on a cold night, but it’s something. Vote for synchronicity.
Lesson 2: Rapid Prototyping
As you’ll discover in the next part of this series, Pirate Radio turned into quite a respectable production. If I’d had a glimpse of what this show would become in COVID-March 2020, I would have been overwhelmed at even imagining pulling something like that off. I don’t think I ever would have begun.
Yet, in the thick of it, this quite-respectable production was almost an afterthought. I could get the whole show going in about 15 minutes of setup, and was broadcasting HD video and hi-res audio with two cameras, coloured lights, and the ability to do my own scene changes. Where it began and where it ended up were quite a distance apart, and it got started because I had this strange idea of playing music from Spotify to people I cared about, over a Zoom call every morning.
Despite seeing the wisdom of rapid prototyping on display here, I forget it all the time. All-the-time. An idea comes to me and instead of then figuring out the simplest possible way to test it, I get hamstrung on executing some pretty elaborate details on something that may be so fundamentally flawed that nobody cares about it.
Pirate Radio ended up becoming an end-of-week, Friday afternoon experience. It began as an early-morning thing. This was entirely based on listener feedback and finding a spot in their day that could most support 90 minutes of beats and banter from the high seas of the Internet waves.
Have an idea? Make a really, really, really simple version of it. All the magic happens in evolution, right Darwin?
Lesson 3: The ∞ Power of Music
This is the first and certainly not the last time you’ll read me writing about this theme. National anthems, college fight songs, and pop hits all show this so clearly.
The fact that we were in a global health crisis and our lives were being upended created a massive amount of stress, fear, uncertainty, and a whack of other states that some poor lab rats have objectively demonstrated take years off your life if you spend too long in them. Basically, we were freaking out.
One activity I love running with a group is asking every member to submit two songs they could imagine as their walkup tune (think WWE/UFC down to the ring/octagon, MLB-at-bat…). I play the songs randomly and have people guess who it belongs to. The thing that always gives me a kick is asking people for a story connected with the song. Try it the next time you discover a tune someone loves. Even if people say, Oh, I just like this song, there’s no story… push them. There’s always a story. Ask them the first time they ever heard it. Or if they were on a trip. Or with someone they loved. You’ll see the lights come on, about 5 cm behind their eyes, and something remarkable will come out.
I was pulling on this in the earliest days of Pirate Radio. I asked people for songs from earlier times in their lives, when they felt secure, when they felt comfortable. We’d listen to Bran Van 3000 and Blink-182 and people would share these moments from high school or when they took a first trip to Europe with friends. We exited the COVID crisis together for a brief moment, and traveled to a safer, more certain time, and we did that together.
And we did that with music.
Too often, music is seen as an accessory to support some other experience, but when you’re trying to bring a group together in a meaningful way, explore what you can do with playing music to all of them at once just because. Or better yet, find someone who doesn’t normally have a loud voice, and prop them up to do it. Real connection will ensue.
This is the first instalment of the tale of Pirate Radio. Stay tuned for how our adventure develops: coming out of retirement, hosting Shopify summit, getting ERGs on the air, and voyaging to YouTube.
All this and more, in Lessons from a Pirate.