Easier Said Than Done: Reflecting on Gumroad’s Largest Partner To-Date
If you follow Gumroad, me, or another member of the Gumroad team on Twitter, you’ll know that we had some pretty exciting news this week. Getting Wiz Khalifa on the Gumroad platform was anything but easy. It took numerous emails and calls, multiple in-person meetings with his team at Rostrum Records, even a last-second redeye. Not to mention the hours of preparation, follow-up, and hard work. And even then, the first night’s video release caught a snag when we were overwhelmed by the amount of traffic that an artist with 7 million Twitter followers pushes at 1:36am ET. Fortunately, our team was able to get things under control that night and made some significant infrastructural improvements so when he Tweeted a video again on Saturday night, Gumroad withstood the barrage of Wiz fans without a problem.
The point of the above paragraph, however, isn’t to explain how the Gumroad team busted its collective ass to get one of the most popular artists on our site (which we did). But rather, it is to underscore just how hard this “shit” (read: cold emails, business development, the music industry, startup-big business relations, technological scaling, etc) is. Last week, Bijan Sabet (very appropriately) Tweeted how people outside of startups don’t realize the rollercoaster ride of emotions that teams endure. And frankly, despite my obsession with tech / startups / VC, I hadn’t realized it either until beginning to work with Gumroad back in April. This past Thursday was a lifetime of morale highs and lows in and of itself, let alone the aftermath on Friday and the build up to Wiz’ second Gumroad Tweet on Saturday.
Reflecting though, the experience was fun as hell - there’s nothing quite like the satisfaction of working hard / frantically / maniacally to accomplish something great at a young company. And all the ups and downs were and will continue to be learning opportunities for our team and each one of us individually, as we strive towards building something great.
