The Stewart

This is the story of how The Stewart came to be, though I’ll admit up front some of the exact details are fuzzy, as I was enjoying myself at the XOXO conference this last September amid extreme temperatures.

It all started with this photo that my old friend Paul Bausch took of Stewart Butterfield:

Paul was leaving the conference early, saw Stewart outside the center, and Stewart waved him over. Stewart filmed this Vine video of Paul and he asked Stewart to pose for a photo after. For some reason, Stewart struck this crazy pose, Paul took a single photo, and later posted it online. It was utterly amazing and ridiculous and I instantly fell in love with the shot.

I remember running into Stewart the next day and asking him where one would obtain some Slack socks. He told me to attend their company bar meetup/party the next day and I made a mental note to do just that. I also mentioned Paul’s totally epic photo of him that was so good I might have it framed or painted or something. Stewart gave me a weird “um, ok” which is the correct response when someone says they might do something like that.

During the XOXO fest, I visited the Panic Software offices, which features “The Founders’ Room” with an over-the-top oil portrait of Cabel and Steven done by Chinese artists that they found online. I also remembered a recent Medium piece by Rex Sorgatz about him getting a Vermeer recreated by these same online Chinese artists. By the end of the weekend I knew what I had to do next.

The Painters

I literally just googled “Chinese art painting from photo” when the conference was over and found http://www.chinaoilpaintinggallery.com/ as the first result. I looked around the site, and noticed the pricing for a 20" x 24" painting was around $200, so I emailed (they only operate via email) asking how much The Stewart would run and if they could paint it. They said they could, and it’d take 2–3 weeks and cost $215 US with shipping. I said “let’s do this” and the person I’d been interacting with, Shi XiuMei, asked me to send the money via PayPal upfront.

That last bit took a small leap of faith. I was sending $215 to someone on the other side of the globe and who knows what they might do with it. But their site looked legit, so I put my trust in my new unknown email pal and sent the funds.

A couple days later, they emailed back, asking what I’d like the background of the painting to be? Would I want it to be faithful to the photo, or something else? I did a quick Google Image search and sent them a GIF of the Slack logo, asking if they could somehow make it the background, with muted colors so it looked right.

Shi XiuMei emailed back this mockup, and I knew right then and there that I put my trust in the correct random internet painter strangers because that image looks even better than the already amazing original.

A few weeks went by, and I started to get a little nervous about ever seeing a painting, until one day I woke up to an email with the image at the top of this page, asking if I thought it was OK, and if so, they would soon ship it my way. I said it was fantastic, thanked them profusely, then waited on international DHL and customs to do the rest.

A couple weeks later the painting arrived at my doorstep in a rolled up canvas, which I then took to a local frame store to finish up. I admired the Panic Founders’ Room painting and noticed they had a nice big gaudy frame on theirs. I quickly found out those are quite expensive (on the order of ~$500 for this size painting), and when I explained to the framers this whole painting was kind of a silly joke made for a friend, they went about finding the best, most regal, most gaudy frame possible for the least amount of money. In the end, we found a cheap wood frame on sale and put a gold small frame inside it.

The Unveiling

There were grand plans at first, where I’d drive down from Portland, Oregon, meet up with Cal Henderson from Slack, and in the wee hours of the night, we’d hang the painting covertly for Stewart to discover the next day. It all became rather complicated with Stewart’s crazy schedule and in the end, I couldn’t make the trip and instead ended up shipping it direct to Cal, which was way cheaper than I thought (only ~$35 via Fedex).

The painting was set to arrive last Friday, the same day Slack announced new funding and their billion dollar valuation, which would have been perfect serendipity, but Fedex arrived too late on Halloween to an empty office and it didn’t get there until Monday. Yesterday, Cal hung the painting, along with signs telling employees not to tweet it or post it to Slack, to let Stewart find it on his own the next day.

And today was that day, and that’s the story of how The Stewart came to be.

So if you ever find yourself at the San Francisco headquarters of Slack, be sure to check it out in person. And try out Slack if you’re not already using it, it’s really amazing software.