Bill Gates reflects on the beginnings as Microsoft celebrates its 50th anniversary.

On the 50th anniversary of Microsoft, co-founder Bill Gates posted on Instagram, reminiscing about his initial experiences. In the video, he compiled several vintage pictures and added the following text, “Unfortunately, I’ll never feel cool again because this was me in the early Microsoft days.”

On the 50th anniversary of Microsoft, co-founder Bill Gates posted on Instagram, reminiscing about his initial experiences. In the video, he compiled several vintage pictures and added the following text,

“Happy 50th birthday, @microsoft. Thanks for the memories-and awkward photo shoots,” Gates wrote in his message for the company.

To celebrate Microsoft’s 50th anniversary, a whimsical and surprising element united three of the firm’s most legendary leaders—Bill Gates, Steve Ballmer, and present CEO Satya Nadella—for a fun dialogue with none other than Microsoft’s AI assistant, Copilot.

The gathering was more than a sentimental journey—it was a modern experience infused with humor at its core. In a video posted by Nadella on social media, the AI-driven exchange became entertaining when he asked, “wrap it up by asking or maybe roast giving us each an AI roast?” To which Copilot playfully replied, “Alright, Satya. Let’s spice it up.”

As the AI turned its attention to each of the three tech giants, Gates received a particularly cheeky jab: “Now, Bill, you’ve got that signature thoughtful gaze, but do you ever think the AI might feel intimidated by your intense-thinking face? I mean, it’s like it’s waiting for a blue screen moment.”

Gates responded in good humour, “I hope so. I mean, that’s all I’ve got left is these AIs get so damn intelligent. It’s just that gaze and my willingness to criticise that differentiates me.”

Copilot came back with a compliment, saying, “And it’s a formidable gaze indeed, Bill.”

Ballmer couldn’t resist jumping in with a witty remark of his own: “Copilot, would you ever be willing to criticise him?”

The exchange wrapped up on a charming note, with Copilot offering a toast: “Here’s to another 50 years of innovation and adventure. Cheers.”

Gates, never one to miss a beat, replied with a smile, “Whatever that means to an AI. Does it drink?”