Bye Skype

You were the cutest 🥰

Microsoft is turning off Skype in May and that’s ok. In the world of tech, 22 years is a really good run.

I bleed nostalgia all over this bloody blog yet I don’t feel the same retro love for Skype - but plenty of people do. Nostalgia is baked in experiences - the younger the better - and I just didn’t use Skype much in my personal life. My love needs a deep fryer.

Skype was beloved for more than the yum of deep fried dough. The people who loved it had friends or lovers in faraway places and Skype let them talk (and see!) them, skirting long distance calling. When Microsoft bought Skype in 2008, their marketing head gave us a talk about how beloved the app was - people got married on it and apparently still do. Skype was masterful at harnessing that love, sharing those stories, and incorporating that sense of connectedness into their branding and user experiences with clouds and bubbles and the most amazing set of Emojis ever.

Skype was disruptive before that was even a thing, smashing through the status quo of squalid corporate tech, shaking the very foundations of venerable monolithic institutions like AT&T. Ok, AT&T’s monopoly was busted long before, but all the baby bells were built atop the same stuff. Skype was the first to poke at the core of the empire Alexander Graham Bell started building with his first phone call 150 years ago.

When my group acquired Skype it was a big freaking deal and it cost $8 Billion dollars; I would soon get to know Skype very well.

Skype has an amazing origin story. Genius engineers from faraway lands build new stuff, improve and combine existing stuff and then knit it all together in a fun and FREE service that makes phone and video calls all over the Planet. Skype growth skyrocketed, amassing over half a billion users at its peak in 2010.

Revolutions start with the people - Skype made it easy and amazing to talk to your gramma. Business took note.

Did I mention the emojis were amazing?

A couple of years after founding Skype, the core crew cashed out and sold it to eBay for some billions. All the founders and all the employees made money, as they should, but alas when you cash out you are now at the mercy of some odd number of overlords.

So it went, and Skype got schlepped from eBay - which never figured out how to integrate Skype into it’s business - to a private equity firm called Silver Lake, then after another five or so years, to Microsoft for more billions.

When Microsoft acquired Skype they’d reached tech apogee. Social networks and mobile were coming on fast, changing the game. Still, Skype was an amazing brand with a massive and sticky base of devoted users.

Integrating Skype into Microsoft’s products took some doing. The no-brainer was incorporating Microsoft’s consumer messaging app then called MSN Messenger into the more popular and way cooler Skype.

But no-brainers on paper don’t necessarily play out when tech is involved. Without getting pedantic, the problem was the way users identified or authenticated themselves. Y’know - sign-in. This was in the early days of cloud identity, and it was a chaotic world. Skype had a way, Microsoft had a way (called MSA or Microsoft account) but we never could work out a way to combine the two without a bunch of hassle for the user. That resulted in a ton of friction moving Messenger users over to Skype, and in a world with new and cool options (WhatsApp for example), that meant we lost users.

Honestly, that didn’t really bother me - I worked on the business or enterprise side. But there’s an interesting co-dependency between consumer customers and business customers. You make your money (most of it) from business, but having great consumer products feeds your business offerings. The two are symbiotic.

Enter our next big idea. Maybe not a no-brainer, but at the surface it made sense - why not leverage the cool factor and ease-of-use of Skype into our corporate offerings? Users always complained about the learning curve of our products.

So we created a Skype ‘skin’ over our client which at the time was called Lync. A lot of my corporate clients - especially the big banks on Wall Street - took this as an affront to their dignity. Skype had no place in a serious institution. Man they were mad. The changes to the client were also, well painful at first, breaking some features they used and had even built internal systems on.

They got so angry with us that I had to fly a bunch of our execs out to NYC so these guys could vent in an exhausting all day affair about client and server technologies and roadmaps, muffins, cold coffee and apologies. Yet, we stayed the course and soon we completely rebranded the client from Lync to Skype-for-Business or SfB.

Then came the cloud. Microsoft needed to get Office on the cloud and SfB became part of our cloud offering. A lot of great tech was built to support this transition and some of it came over from legacy Skype. One example is Skype’s magic codec, called SILK which we brought over to our media stack to improve the quality of our calls.

Gurdeep Pall ran my group for most of this time and earlier this week he posted highlights of the massive engineering effort we took on to rebuild Skype in the cloud. MS Teams then used this same backend and it was it’s ability to scale that got us through the massive run up in usage during the pandemic.

Skype consumer ran on a peer-to-peer architecture which basically means clients talked directly to one another. But to enable scenarios like conference calls (3 or more people), it all had to be rewritten. Lync/SfB had conferencing capabilities (MCUs) but everything had to be re-built for the Cloud. As with any big lift like this, eggs were broken and my teams job was to make sure customers transitioned with us through all the bumps. It got pretty bumpy.

Sometimes you just need to start fresh. There’s a term called ‘technical debt’ when systems are built up over time and you make compromises to accommodate older components or clients, knitting old code together with new. At some point, performance and scale suffers. Teams was our do-over, cloud native from the start.

In May, Skype will prance over the horizon on a unicorn while Teams climbs higher in its rocket. Skype users will move over to the consumer version of Teams. I hear it works well and Teams is pretty cute too.