Let’s rewind the clock.

It’s 1975. 
Two guys – Bill Gates and Paul Allen – decide that writing code for the Altair 8800 is worth quitting Harvard over. 
That decision gave birth to Microsoft.

Their vision? “A computer on every desk and in every home.”

At the time, that was laughable.
Now… look around (in your pocket!).
For 50 years, Microsoft has somehow been everywhere and nowhere. 
The most valuable company that rarely feels like the coolest one. 
The brand that powers the back office, not the front row. 
The workhorse. 
The spreadsheet. 
The PowerPointer.
Still here. Still thriving.

A company of eras (with apologies to the Swifties)

We’ve seen Microsoft grow in arcs.  
There was the DOS-to-Windows rise – a rocket ship powered by licensing deals, bundled software and a point-and-click way for everyone to use a computer.  
Then came the Office revolution and the Windows 95 moment that turned computing into culture (remember the midnight lineups?).  
We endured what some have called the “Lost Years” – a time when Vista, Zune, and a mobile strategy didn’t click and nearly tanked the ship (not to mention ghosting social media).  

Then came the Satya Nadella reboot.  

Quiet. Focused. Cloud-first.  
And the rebound? Impressive. From a $269 billion company in 2014 to nearly $3 trillion today. 
That’s not a pivot – that’s resurrection.

What’s fascinating is how Microsoft has remained relevant – not by being first, but by being big and patient.

The browser? They didn’t invent it. But Internet Explorer crushed Netscape.
Gaming? Xbox was late to the party. Still here.
Cloud? Amazon won the first round. Microsoft came back swinging with Azure and Microsoft 365.
AI? Well… we’ll see… but it’s looking vibrant.
The future is being framed around Copilot – Microsoft’s AI push that touches everything from Word to Windows to cybersecurity.

Microsoft is betting $80 billion this year alone on building AI infrastructure. 

Add in its multi-billion-dollar stake in OpenAI and its ability to get Copilot embedded everywhere, and you start to see a familiar strategy: don’t own the future – license it… connect it.
The thing about Microsoft is this: They’ve always been a utility brand trying to act like a lifestyle brand. 

But the world runs on Microsoft (sorry Dunkin Donuts).

Banks. Hospitals. Governments. Enterprises.
And with tools like Teams, Office, and Azure deeply entrenched, they don’t need to “delight” consumers in the way Apple or Google does. 
They just need to be indispensable.

And – with all of their stumbles – they’ve made it to 50.

Like some of the great entrepreneurs and businesses of our time… risk is everywhere and always… failure is always an option.
So, here we are.
Fifty years in, and Microsoft is still trying to prove they’re relevant – not just reliable. 
Still trying to make “enterprise” feel exciting. 

If Microsoft’s history has taught us anything, it’s this: Never bet against the company that made Excel addictive.

This is what Elias Makos and I discussed on CJAD 800 AM. Listen in right here.

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