An email was sent to me today with a link going over the top 10 failures of Microsoft and one of my favorites on the list came in at number 2: Microsoft Bob. I remember wanting to own this program because I thought for some reason, it would make life easier. Let’s see why…

Back in 1995, Windows 95 was released as a follow-up to the ever-so-popular Windows 3.1. If you remember correctly, there wasn’t much in the way of operating systems before Windows and without it (let’s be honest), there wouldn’t be much of computer world today. What’s interesting is that Windows 95 was supposed to be the crown jewel of the industry—making computing far easier than it had even been and with a bit of flash too. So why then must Microsoft create another piece of software on top of Windows that’s supposed to make things easier??

Introducing Microsoft Bob

Bob was a house. A virtual house that contained a virtual dog and many different rooms of varying design and function. This is how it worked:

• You logged into Windows 95 – After realizing it was much too difficult to perform any tasks, you opened Bob.
• Bob launches – You’re presented with a door that allows you to sign in.
• You choose a room – Based on what tasks you want to do, you pick a room that has what you want inside.
• Open an app – Click on the applicable icon to open the app you want to use.
• Follow instructions – Now you get hand-walked through every single step of doing even the most mundane tasks.

For the best instructional walkthrough, you must watch this video:

I think what’s most disturbing about how Bob worked was just how much more difficult things seemed to get after using him. This is pure irony considering Bob was supposed to simplify things. Bill gates was even quoted as saying Bob was ahead of his time. I’m sure at that time, this seemed far-fetched, but if you really think about it, software interfaces have become more GUI-based and things are becoming much easier to do on computers than ever before.

$0.45 per email?!

As I was learning more about Bob, I found out that when he came out, the Internet was just starting to take off so Bob included an email app that would allow you to send up to 15 emails per month that were each limited to 5,000 characters. Beyond that, you would have to pay $0.45 per email sent! These emails were sent over the MCIMail service, which was essentially a dial-up email account.

Can you imagine having to pay to send emails? What a bargain—a stamp to mail a real letter cost $0.32 and an email cost $0.45. I guess things have really changed for the better. Now you can buy a stamp for $0.44 and send as many emails as you want for free. I wish we could still charge spammers though.