October 11, 2015


I guess I could say my dad was a geek, but that’s not exactly true. When people think of geeky dads, they think of Gordon Clark from Halt and Catch Fire, or maybe Rick Moranis in Honey I Shrunk the Kids, but my dad was nothing like that.

My dad was a businessman, through and through. A friendly, suit and tie kind of guy, one who would take his clients to dinner and invite them to Blue Jays games.

The geeky part of my dad was that he just loved tech. He credited the Macintosh he bought with transforming the way his office did business, and was always keen on getting the latest versions of whatever OS and software he was using at the time. The guy was an excel wizard. Even today, fully equipped with a CS degree, I still don’t understand some of stuff he was pulling in his .xls files.

I clearly picked up his passion for technology and became his go-to guy for websites and technical advice. After first introducing him to Dropbox, I’d hear a yell from another room: “I put the files in the hotbox, did you get them??” Classic dad.

He took me to New York City when I was only 15 so we could attend MacWorld, where we woke up at 5 AM to line up outside the Javits Center, and later watched Steve Jobs announce the Power Mac G4 Cube. He’d eventually buy me another G4 that I’d learn to program on, starting my career as a software developer. (I’ve since grown up to realize how incredibly privileged I was to have had both the ability and the support to pursue a career in tech.)

He was so excited and so proud when I told him Apple gave me a job offer and I’d be moving to California to work there full time. While I figured he was sad to not have me nearby anymore, I knew he was more excited that his son would be taking part in what he viewed as a technological (and business) revolution, being on the forefront of the latest and greatest tech-y things. He was also probably pretty pumped to get that family discount.

Over the years he bought every iPhone and iPad that launched, even if he didn’t need it. He had more apps installed than anyone I knew. And he got such a kick out of all of it. I remember now when he would visit me in San Francisco, we’d be touring Apple or some other start up, and he’d get kinda quiet. At the time I worried he was mad or bored or something else, but I realize now he was probably just taking it all in. Savoring the moment in a quiet, private way that I’ve come to see other dads do.

My dad died last June at age 64. Kidney cancer, no symptoms until it was already way too late. Really shitty stuff.

In the time between then and now I’ve dealt with it pretty privately. It’s super sad to lose a parent, especially in such a quick and expected way, and I don’t like to bring others down. I think about him a lot, naturally, but the surprising thing, though perhaps it shouldn’t be, is how much I think about him around tech events.

It’s easy to forget just how relentless the tech industry is. Since he passed, Apple announced and shipped a watch, two iterations of the iPhone, and even showed off a big-ass iPad. At each one of these events, the thing I couldn’t get out of my head, and still drives me to tears, is the thought “Ugh. Dad would have loved this.”

This weekend I got to visit and help (a tiny bit) with my wife’s new office expansion and move at Square. It’s without a doubt the most beautiful workspace I’ve ever visited. And it’s also probably the most technologically advanced, not only in tools but in scale. iPads with beautifully designed custom software handling all the meeting room coordination, ubiquitous video conferencing, robots wheeling around with human faces on the eye-level screens – telepresence, man. And again, it hit me: dad would have loved this.

It’s bittersweet to say the least, but this pang has come to serve as helpful reminder.

Tech has a lot of problems: toxic work cultures, lack of diversity, unreliable software, privacy issues, to name a few. It’s easy to become jaded to the fact that we’re living in a future that is greater than most of our ancestors could have imagined. That’s not to say things couldn’t be better, or that we shouldn’t be trying harder on so many fronts. Despite these shortcomings, it’s critical, perhaps necessary, that we take moments to recognize how far we’ve come, and how truly magical our world is, and how important it is to keep working for positive change. Billions of people, my dad included, have lived and died before they were able to see the most magical things, which to us are always around the next corner.

My dad had a lot of skills, and one – that I’m apparently still learning – was to recognize the power and significance of the newness of things, as they keep happening to us, at us, over and over again.

Thanks dad, I miss you a lot.