Cover photo

Picture Jennifer Aniston teaching you how to use Windows

Diving into the launch of the biggest tech launch of the 90s: Windows 95

gm creators!

I hope everyone had a great labor day weekend 😎

Over the weekend, I got a last minute day pass for the US Open on Monday and had an absolute blast. I grew up playing tennis and watching the legends on screen, so finally being able to see the action live was unreal.

I ended up coming back to my apartment super late so wasn't able to get a post in last night, but going to make sure I cover an extra post in this week to make up for it 💪

Over the weekend, I wrote a post on how Jeff Bezos was convinced that he had to drop everything and go "work for" the internet. was a newsletter ;)

You can read the full piece here!

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Today at a Glance 👓

Picture Jay Leno and Bill Gates on stage together with The Rolling Stones song "Start me up" playing in the background.

No, they're not performing at a comedy show but rather launching one of the biggest tech products of the 90s...

Windows 95 Launch 20 Years Ago

Microsoft's Windows 95 was a huge milestone for the tech community. Not because of the software itself but rather for the company's over the top marketing campaign. Regardless of what you think of Windows itself, there's no doubting that the launch of the new OS was one of the most hyped up, talked about events in tech at the time.

In today's post, I cover 3 takeaways after spending some time researching the Windows 95 launch.

  1. Keep it simple stupid - less about novelty, more about simplicity

  2. A CMO's Disneyland - a look into Microsoft's $300 million marketing campaign

  3. Sprinkle in the Internet - gn Netscape, gm MSN

Let's dive in 🚀

1) Keep it simple stupid

After several delays, the Microsoft team was finally able to ship Windows 95 to the public. The team had been working on the product for over three years, and it was a huge moment for the company. To put it simply, Gates needed a big win and everyone knew it.

Considering the amount of time that went into developing Windows 95, it's worth noting that technically speaking, many of the new features advertised were not necessarily novel. Either Apple or previous versions of Windows already had them. However, Windows 95 was able to take those features and present them in a way that made sense for non-tech users. A better hood for the engine.

Here are the main features that came out of the launch:

The "Start" button!

Apple had previously introduced the 'Finder' feature, represented by the Apple logo on the top left corner of the screen. However many people claimed that they just thought it was a logo. Windows decided to make their version bright and flashy; it was crystal clear to anyone that they should "Start" there. Users could instantly access all their applications without the need to manually add them from a directory. This was game changer - from the minute you got Windows 95 set up, you could immediately get started.

Windows 95 to Windows 10: How the Start Menu has evolved | Trusted Reviews


Previously, users primarily used the Program Manager, an interface where running applications were represented by icons inside the Program Manager window. It's sort of like going to the app store every time you want to use an app or go back and forth between tasks. This method eventually became cluttered and confusing. The taskbar streamlined this by providing a central location at the bottom of the screen where each running application was represented by a button and made for efficient task switching.

Windows 95

Plug & Play

Before Windows95, adding any external hardware such as a mouse and keyboard was apparently a nightmare. You had to get into the weeds of the settings, do manual configuration, etc. The new OS made it super easy to simply "plug" in your hardware and start using it immediately! Windows would detect the hardware, auto configure the settings, and have the new device functional without the need for a restart.

What's interesting to me of the above features is seeing how revolutionary these simple ideas were for the time. Today, we're at a point where even the idea of plugging in your mouse seems ancient.

This makes me think about what the "Start" button for crypto will be. Which product feature will just make sense to millions of people around the world?

Comment below if you have a strong opinion here! Would love to hear.

Of course, I think it's unfair to say that the end users of Windows 95 just got it on the first try with just their product. There's pretty much a 100% chance that most people wouldn't care for the launch of this new OS if not for Microsoft's marketing campaign.

2) A CMO's Disneyland

The most interesting part of researching the Windows 95 launch was learning that Gates and team had spent over $300 million marketing it. Remember...this is 1995! That was unheard of in the tech industry for the time.

The only other example that I can compare this to is AOL's trial CD carpet bombing strategy led by Jan Brandt. If you want to learn more about how she took AOL from third in market share to industry leader, check this post out!

In fact, Microsoft even took a page out of AOL's playbook - they sent thousands of trial versions of Windows 95 to US/UK users.

But the real magic of the marketing was, in my opinion, the partnerships with key culture icons of the time.

They were able to get the Friends actors Jennifer Aniston and Matthew Perry to record a user guide on how to use the new software. At that time, these actors had unmatched influence in American entertainment - everyone knew who they were. If "Rachel" and "Chandler" were talking about something, there's a good chance people will watch.

It's an hour long...if you're interested check this video out.

Other strategies that Microsoft included:

  • Windows 95 Sapporo Beer cans

  • Lighting up the Empire State Building with Windows 95 colors

  • Inviting Jay Leno to host the launch event

  • Making complement marketing in other countries/languages such as Spain & Japan

On the night of August 24th, at midnight, there were literally Black Friday type lines around Best Buys all across the nation! Here's a picture taken by Rick Maiman of a New York store.

Rick Maiman

Though many people in the tech community who were already Mac Maxis looked down on the whole marketing event, the reality is that it worked for Microsoft. The company sold millions of copies within just a few weeks of the launch. By the end of the first year, there were about ~40 million copies sold!

3) Sprinkle in the Internet

One quick point I wanted to mention was something I learned from reading chapter 2 of How the internet happened.

Gates was notoriously late at realizing the internet was going to the next "information superhighway", not TVs. He didn't realize the internet had gone through a complete revamp and was still operating with the late 80s mindset that the internet was a niche toy. And eventually, as Netscape start gaining traction and publicity, he realized that the internet had to be Microsoft's #1 priority.

He tried reaching out to the Netscape team to partner but was rudely rejected. And a few months before, AOL had acquired Book Link (another browser of the time).

But of course, Gates was not going to go down without a fight - he had the money, distribution, and power to do what he wanted.

So what did he do?

He signed a $2 million licensing agreement with Spyglass - the same company that had the rights to the Mosaic web browser.

Irony of ironies, the code that would be the basis for Microsoft's web browser (and the weapon Microsoft would yield against Netscape) was a descendant of the same code written by Marc Andreessen and Eric Bina" - How the Internet Happened

In the weeks leading up the Windows 95 launch, he had a six person team work around the clock to hack together a v1 of the Internet Explorer. It didn't have to be perfect or as good as Netscape, just good enough to work. They would improve on it later.

And just like that, Microsoft had entered the browser wars. All of a sudden, millions of people now assumed that to access the internet, they needed to use Windows! The words became interchangeable for them.

Moral of the story: don't mess with the guy who has distribution 😂

By learning tech history, it's easier to identify tricks & techniques that can help founders approach the idea maze even today.

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