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Melinda Gates on ‘the hardest thing' she's ever had to do

JP Mangalindan
Chief Tech Correspondent
Businesswoman and philanthropist Melinda Gates recalled on Wednesday the “hardest experience” of her life while onstage at the annual Grace Hopper Conference for Women in Computing, held in Orlando, Florida, this year.

It hasn’t always been smooth sailing for businesswoman and philanthropist Melinda Gates.

At this year’s Grace Hopper Celebration for Women in Computing conference on Wednesday, the 53-year-old Gates, a former Microsoft employee, explained that the road to success is almost certainly paved with a few failures along the way.

“Any time that you’re dreaming big, you’re also going to have spectacular failures,” she said. “Have you ever heard of Microsoft Bob? Well, if not, I’m actually not surprised.”

Launched in March 1995, Microsoft Bob was a software product intended to supplement Windows 3.1 to make it easier to use by reimagining the interface as a virtual home filled with clickable objects placed in different rooms. Clicking the clock, for instance, brought up a calendar; clicking the pen-and-paper icon opened the word processor.

Microsoft Bob turned your computer into a virtual home.

Microsoft (MSFT) made a huge promotional push for Bob at the time, supplying flights to Las Vegas for that year’s Consumer Electronics Show with Bob-themed napkins and having senior citizens don Bob sandwich boards and walk up and down the Vegas Strip.

One of the ‘worst inventions ever’

All those dollars, however, were for naught. Critics lambasted Bob for its steep hardware requirements, cutesy art and $99 price tag, on the pricier side for software at the time.

A younger Melinda Gates poses with Microsoft Bob software in February 1995.

Gates, who helped lead the development of Bob, says the hardest moment in her life was giving the first public demo of Bob in 1995 after the negative reviews had landed.

“I knew I was going to get killed,” she recalled. “So I walked out onto the stage with a t-shirt that had Microsoft Bob’s face on the front. I turned around, and on the back, I put a big bullseye. Now, it got some laughs at the demo, but more importantly, it was a reminder to myself that I signed up for this, that the chance to take big risks is exactly what I love about tech.”

And even though Bob continues to make tech media lists for being one of the “ worst inventions ever” long after it was discontinued in 1996, Gates cautions people that even the best innovators can be surprised by what succeeds with consumers.

To wit, while Bob is a thing of the past, there’s one unique software feature Bob introduced that still lives on in other Microsoft software: the Comic Sans typeface.

“Sometimes, you just don’t know what’s going to work,” Gates added with a grin.

JP Mangalindan is a senior correspondent for Yahoo Finance covering the intersection of tech and business. Email story tips and musings to jpm@oath.com. Follow him on Twitter or Facebook.  

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