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A Skype retrospective was called for once I read that the service was being closed by April 2025.

Skype retrospective origins.

Skype was a thing right from the get-go when it launched in August 2003. There had been voice-over-IP (VoIP) services before Skype. Full disclosure, I worked on Deltathree; an Israeli predecessor of Skype.

About this time, if you needed to make cheap overseas call, you would dial in to a special service and then dial the overseas number. This would relay your call via VoIP. These calls were also facilitated direct from a PC as well using VoIP.

Previously, telephone calls were charged per voice minute. The further away the call was, the more expensive it was. VoIP disrupted the telecoms cost model.

Enabling technologies.

As broadband networks became more prevalent and Wi-Fi meant that you were no longer tethered to the ethernet connection of your router. At the time homes had an area delegated for internet access. Laptops were much less commonplace.

The original iMac was a success because it was a plug-in and play solution for internet access. It’s iconic ‘candy design’ helped differentiate it from the competitors beige PC.

By the time Skype was released I had an Apple iBook, a consumer laptop that pioneered the adoption of Wi-Fi, back in 1999, but my first broadband router at home didn’t support Wi-Fi. Broadband, Wi-Fi and 3G networks facilitated the start of Skype. Those networks provided the always-on connectivity to get the most out of the app.

Low-key start.

If there was any ‘thought leader’ on VoIP at the time, it would have been Jeff Pulver. Pulver didn’t bother discussing Skype at the time. Instead he was focused on expected government regulation, Vonage, PC VoIP software X-Lite and Windows Messenger.

Skype first appeared on Pulver’s radar in December 2003, after Red Herring announced that they had secured a first round of venture funding. Pulver praised their ‘viral marketing’.

It wasn’t obvious that Skype would be a winner.

Messaging at the time.

The primary messaging platform at the time in Europe was SMS. Instant messaging was starting to be used informally in workplaces. It was as much about the community norm as anything else. I started off using ICQ with Israeli clients, then Yahoo! Messenger, AIM (AOL Instant Messenger) and MSN Messenger. It was all a bit messy, so I pulled all my accounts together using Adium.

Take-off.

Skype quickly took its place on my laptop when it released its first Mac client in March 2004. By the summer, one of my clients at the time got rid of their desk phones when they moved office and had employees do internal and office-to-office calls via Skype-to-Skype instead. Giving someone your Skype ID became as common as giving out your email.

At the time Skype offered encrypted voice calls held over a peer-to-peer network. The encryption was contentious as it something of Skype’s own design and wasn’t audited.

In 2005, Skype was sold to eBay. The synergy between them wasn’t clear.

Joost

A year later, the Skype founders left and founded The Venice Project aka Joost – a peer to peer video platform. It was a photo-streaming platform. I liked Joost for its sub-Amazon Prime Video film library including obscure 1970s English language overdubbed martial arts films. But there was also Viacom content available.

Meanwhile under eBay’s ownership, Skype incorporated video calls into its offering. I ended up in a long distance relationship with a Hong Kong-based fellow Mac user and we ended up talking every day via Skype. It even worked when she visited across the border in Shenzhen.

Mobile impact

You can’t write a Skype retrospective without talking about its role on mobile.

Hutchison 3G (known as Three), was a cellular carrier brand put together by CK Hutchison to build a global 3G network in Asia and Europe. In 2007, Three launched Skypephone with Skype. The key part of this as an unremarkable looking candy bar handset.

The Skype phone allowed you to see the status of your Skype contacts on the phone, allowing for presence on the go, in real time (network permitting) which was revolutionary. But we take it for granted on WhatsApp now. There was a couple of forums that gave out widely copied workarounds for the clunky implementation of Skype.

For some reason Hong Kong always got the best features. You could have two numbers on your phone there. The first number was your proper mobile phone number that worked like you would expect it to. The second was your ‘SkypeIn’ number – a soft telephone service.

I had worked on pioneer mobile app Yahoo!Go previously, which only allowed email and no VoIP calls. The Skype phone was a major leap forward because it allowed synchronous communications when connected to a network.

There would have been no WhatsApp, Viber, WeChat or LINE without Skype leading the way.

A nerdier fact was that the Skype phone ran on the BREW application development platform by Qualcomm. It allowed Java apps to be downloaded directly from early app stores before the iPhone. At the time I was side loading apps from my Mac on to my Palm and Symbian phones.

Beginning of the end.

The peak of my Skype use was keeping in touch with my parents when I was working in Hong Kong. Video calling made the world feel closer and they got to see some of Hong Kong with me because of its higher quality 3G network.

Soon after I got back, we switched to FaceTime. This was for a couple of reasons. Skype had an increasing number of spam accounts and phishing attacks. Secondly, FaceTime had an easier to use interface.

This is the point in the Skype retrospective when I think that the rot started to set in.

From a software point of view a big decline occurred in 2016, Microsoft had settled into their purchase of Skype and decided to re-architect the system. Out went the peer-to-peer connections and the system moved onto Microsoft servers to mediate Skype-to-Skype calls.

The irony of it all is that the distributed web is now the technology du jour.

Microsoft messed with the user experience and I distinctly remember moving from one version to another and hated the new layout. From then on, it didn’t improve. Skype’s ability to dial out to international numbers was still something that I put to good use, pretty much up to the time of writing. But like an old cheque book, I came to use it less-and less often; knowing that I could still use the service, allowed Skype to be a back-up to a back-up of a back-up.

At the time I was also using Skype for Business in the office where I worked. It was shambolic with each call timing out around the 30-minute mark.

Om Malik had a similar experience.

Skype, was once a beloved product, one that I loved using every day. It was a product I wrote about long before it was trendy. I sent the team feedback. Like all tiny apps that are good at what they do, it became popular and grew really fast. It was sold to eBay, and then re-sold to Microsoft. And that’s when the magic disappeared. Through series of mergers and managers, Skype became an exact opposite of what I loved about it — independent outsider which was great at — chat, messaging and phone calls. It had just enough features, and its desktop client was minimal in its perfection.  Now, as I tweeted in the past, it is “a turd of the highest quality.”

The final bow

A Skype retrospective would be remiss, if we didn’t cover the impact that the service has had. While Skype has struggled with scammers and Microsoft’s sub-optimal operation, its legacy lives on.

The culture of desktop video calls started with Skype. Microsoft Teams, Zoom and Slack are its spiritual successors. A combination of software capability, hot-desking, hybrid working and COVID resulted in long term business behaviour change.

As I write this, IAG – owners of British Airways, Aer Lingus and Iberia admitted that “business travel had settled into a ‘new normal’ that involved fewer one-day trips with flights, in part because of video meetings.”

Skype had some current cultural relevance, particularly on TV where presenters would interview someone from outside the studio, for instance an expert calling in from home, Skype would still be the client used.

At the time of writing, I am looking at Rakuten Viber to substitute my need for a ‘SkypeOut’ analogue.