“They snatched defeat from the jaws of victory.”
That phrase echoes around footy grounds when a team, cruising to a win, suddenly collapses. The hunger fades. The cohesion cracks. The urgency evaporates.
Winners who stay winners do so because they never switch off. They stomp on a throat when they have the chance. And when they’re behind, they still believe they can come back.
Sporting analogies make great business metaphors. They’re colourful, visceral, and most of all, familiar.
Skype is a prime example of dropping the ball over the line.
Microsoft has been a cash machine for decades. Dominant, deep-pocketed, and ruthless when it suits. In short, they know how to win. But last month, they quietly walked off the field and took their former champion with them.
Skype was officially euthanised on May 5, 2025.
The original disruptor. The upstart that reinvented digital voice communication. The king of the mountain. Gone.
Skype began in 2003, the brainchild of two Estonians who wanted to reduce the cost of voice calls by using peer-to-peer protocols. The product exploded. eBay snapped it up in 2005 for $2.6 billion. Then in 2011, Microsoft bought it for $8.5 billion. It should have been a match made in heaven.
But inexplicably to me at the time, Microsoft launched Teams in 2017, and from then on, Skype looked like yesterday’s hero. Despite a global user base, a household brand, and a treasure trove of usage data, Skype was left to wither.
Why? Only insiders can say for sure, but from the outside, it looks like the classic case of a team where the halfback and five-eighth couldn’t agree on the game plan. Maybe one group wanted to modernise Skype. Another pushed all-in on Teams. The result? Strategic paralysis.
Then came COVID, and video conferencing exploded. Zoom turned from a quirky tool into a verb, others rushed to grab a piece of the expanding pie, and Skype appeared to be disinterested in even playing.
Microsoft had every advantage: distribution, brand, cash, data, development talent and loyal users by the millions, but they didn’t press the advantage. They coasted, and the game moved on.
So the final whistle has blown. Skype, once the dominant player, was taken off the field not by a better team, but by its own coach.
Small business owners: don’t assume past success guarantees future wins. Stay hungry. Stay alert. Don’t let a lazy midfield cost you the match.
