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How Hotmail changed Microsoft and email (arstechnica.com)
168 points by ohjeez on Dec 31, 2017 | hide | past | favorite | 39 comments

If you like history like this, you should also read “showstopper: the breakneck race to create Windows NT” (1). It profiles Cutler’s team as they go through the period described briefly in this article to make Windows NT an actual contender to the Unix-based OSes.

1- https://www.amazon.com/Show-Stopper-Breakneck-Generation-Mic...

Showstopper is one of my favorite product development accounts. The other classic is Soul of a New Machine, which has a hardware focus. I worked with many of the folks in that book, albeit a few years after the event chronicled.

Don't forget the OS/2 2.0 debacle, which is an important part of the story and is so bad it is one of my favorite topics.

Anyone interested in story behind Hotmail should checkout:

"PS: I Love You. Get Your Free Email at Hotmail"


and here is the story of how Microsoft acquired Hotmail:


Relatedly unrelatedly reminded me of the ILOVEYOU virus: https://en.wikipedia.org/wiki/ILOVEYOU

"P.S. I love you" could have been in the referral link at the bottom?

What a mistake that would have been, especially when people were new to email and online ads.

Reading this story I find a correlation between Hotmail and WhatsApp, a simple and free product that introduce to a massive audience a different way of communication (Hotmail = Email, WhatsApp = Messaging).

And seeing how Hotmail lost relevance and Gmail take his place few years ago, I'm wondering, is possible now that a massive product like WhatsApp can be replaced with other that do the same thing in the same way? Why Gmail won?, because the 1GB?, UI/UX?, Google marketing? Snapchat is losing to Instagram because Instagram was a established product that start to mimic Snapchat, but a new player that beat WhatsApp/Facebook Messenger? (not in China [1]).

Also, is WhatsApp/Messaging taking the place of email for younger audiences, casual chat, non-work related communications? Oh, I have an idea, I will love to have a "email" feature on Signal, move the asynchronous way of communication of email to the messaging apps will be awesome to avoid the attention economy / texting fatigue (and have encrypted email without the PGP complexity!). A nice feature to Signal to differentiate from the competition imo. I'm crazy?

[1] https://www.similarweb.com/blog/popular-messaging-apps-by-co...

Hotmail and WhatsApp are very different because the first is devoid of network effects, whilst the second isn’t. What I mean by this is that a Hotmail account can send and/or receive email from any other email account, and hence the relevant number for calculating utility is how many other people have email accounts. This means that an email user can migrate from their previous email provider (Hotmail?) to (say) Gmail and not experience any change in utility because they continue to be a part of the same network.

WhatsApp on the other hand only communicates with other users that have WhatsApp, so choosing to use another messaging service means you cease to be a member of your existing network and cannot automatically communicate with all your existing contacts unless they also switch networks (or add an app to their phone — I currently have no less than eight messaging apps to stay in contact with various people).

This means that transitions cannot be gradual and unilateral. This in turn means that incumbent Hotmail was more fragile vis-a-vis newcomers such as Gmail than WhatsApp is.

That can also have a downside. For e.g. younger crowd were migrating from WhatsApp because they already have their parents or older relatives there, making a privacy issue and also making it less exclusive.

And if you have full contact access, they you really don't loose much network, except the groups. Ya but it does need a strong motivation for a switch to happen immediately (With hotmail it was ofcourse the lack of usernames for new users + the 1GB tier in gmail). With WhatsApp there is no strong motivation but perhaps a slower shift due to fatigue/privacy mentioned above.

I agree that are very different, but in the technical part, for regular users (those who make massive this products), you just have a phone number (email address) and download the WhatsApp app / login to web.whatsapp.com (download Gmail app / login to gmail.com).

This let me think, what happens if you send a WhatsApp message to a phone number that is not registered on WhatsApp? Its saved till the user create an account with that number?

At least in my area, 3 things made Gmail win, and it's a strategy I don't think can win again.

1. Gmail was invite only. It was a badge of prestige, and invites were only handed over to close friends and suck-ups.

2. Deleting emails was a regular need, but Gmail increased your space every time you logged in.

3. Spam protection. Overnight your inbox no longer needed to be pruned for actual emails.

None of those three things is revolutionary anymore.

Spam protection is harder now, and spam senders are more intelligent.

Invite-only things are viewed with suspicion, not excitement.

Most messaging services have enough space per user that deleting messages isn't a concern anymore.

Maybe someone else can revolutionise, but it won't be based on those features. A new strategy will be needed.

I'm surprised you didn't list better search capabilities. GMail was the first email service I used that fundamentally changed the way I organize my email workflow.

That’s right. In fact to this day I remember how they prominently advised “search, don’t sort”, a true paradigm shift. Searching in my local drive could take minutes, while Gmail would take a few seconds.

None of these things were new, more inbox space and better spam protection were available for real email services. But the point of every other free email service at the time, including Hotmail post acquisition, was to upsell you their paid service.

They were therefore crippled in these ways, and purposefully limited to a storage space just large enough to be useful if you went to the trouble of cleaning out large emails regularly. They were also plastered in ads in every way imaginable.

Gmail was a long bet that Google could, with a bit of help from Moore's law, finance a premium email service using the same methods they financed their search engine.

This strategy could absolutely win again, in a market where crippled consumer tools exists for the upsell. For example entry level project tools could easily be something Google could integrate with their office tools. Or indeed if Google crippled their office tools in their ad financed version, someone else could use this strategy against them.

> None of these things were new, more inbox space and better spam protection were available for real email services. But the point of every other free email service at the time, including Hotmail post acquisition, was to upsell you their paid service.

Hotmail and the like required a US address and credit card for their premium service, though.

They weren't options where I was. And nor is it the norm anymore.

You were simply not part of their business model. The point is that their competitors were all freemium. It's not that their competitors were technically incompetent and didn't know how to buy storage or build spam filters but that they were crippled on purpose.

I think most people switch to Gmail mainly because

1. Its spam filter. Remember in the Hotmail days Spam was rampant, and desprite Microsoft best effort ( or not ) they couldn't make Hotmail close to Spam Free, not to mention lots of false positive.

Gmail was the only email services that filtered Spam good enough.

2. And more Importantly; Unlimited Space! Or at least the perception of it. You no longer had to delete email. For people here aren't old enough to know. We used to use Email actually for ALL communication instead of Whatsapp / MSN / ICQ / AIM or what other IM. And people dont want those personal conversation to be deleted. They treasure it.

Unfortunately Hotmail deleted all my old email because of some 6 or 12 months inactivity. I lost all my old record ( Love letter ) then.

WhatsApp and Wechat are now very widely used in all age levels for both work as non-work purposes. Not so much with Snapchat.

Telegram is catching up and I feel it is contesting the space. WhatsApp lacks mini games, channels and stickers.

Is your idea of email in app like a thread communication?

I'm not familiarized with "thread communication" term, I mean a carbon copy of email communication: subject, message, a UI/UX that give you peace to write without read checks, "Writing..." and "Online" statuses of the recipients.

An important factor is that email is a protocol, you could still email your pals on Hotmail after having switched to Gmail. It is way harder to sway a captive audience like WhatsApp's as a whole, now that most of the community is there in many countries.

How did WhatsApp introduce messaging? We already had messaging apps for years, including Skype, Facebook Messenger, iMessages, BBM and so on.

I think WhatsApp just made a rock-solid basic product that cost $1 a year after the first year, and that was its appeal.

No, it was universality. WhatsApp had apps for all type of phone platforms including symbian, blackberry and even Tizen. Your friends could be on it despite whatever phones they're using.

Slightly offtopic, but I was a beta steam tester and used my hotmail for it at the time in ~2002, and to this day my steam account name is still my hotmail address, though they send email to the right place. So everytime I launch steam I get a reminder of the hotmail days. I don't even own the address anymore, I hope they never try to send email there.

The article does a good job digging on the dev/it details of the story, as a designer, I will love to read about the UI/UX side, I think this field also have lot of impact on how Hotmail history unfolded.

I remember this nice UX case study of Windows 95 that I found here in Hacker News, it was gold https://news.ycombinator.com/item?id=12330899

Looking at that Hotmail login screen makes me think how much things have evolved since then. It also makes me think whether we we're just technically nascent during those days or if just severally limited.

I love the story behind the FreeBSD to NT switchover

if you think that one's good have a read about TradElect


a super high-profile project to show that Windows NT, SQL Server and .NET were ready to run a high-availability, high-throughput, low-latency critical system, which MS could then use as a case study for Windows replacing ancient unix systems

you can guess how it all ended

you won't find any mention of TradElect on the MS "get the facts" website these days...

I wonder how little that has to do with WinNT (which is actually a fabulous kernel), and how much has to do with Accenture. When I saw Accenture as the developer, alarm bells went off.

It was all the execution and who did it, than the tech.

Anyone that has dealt with any major consulting company with offshore offices, knows how these projects end, even before they are fully ramped up.

Is MS Hotmail the email service that modified every outgoing mail to have an advertisement for itself in each email? Kind of like a vastly more aggressive and earlier version of 'Sent from my iPhone'? I can't remember if it was Hotmail or Yahoo or both. But all the other advantages of Gmail aside, not modifying your outgoing mail to include advertisements is a big one.

In Hotmail's early days -- before the Microsoft acquisition -- that email tagline was the VC Tim Draper's idea:


Hotmail started it, Yahoomail (nee RocketMail) quickly followed, and Gmail had a more low-key viral roll-out without any ad footers on messages.

Yep just give everything to the Google machine. What could possibly go wrong?

IIRC Google used to scan your emails to serve personal ads.

> IIRC Google used to scan your emails to serve personal ads.

Oh I assumed they still do. Did they stop that practice?

Also I'm not suggesting that giving everything to The Google Machine is a good thing. I was just pointing out the super sleazy gross tactics.

I attach meta-tags about sex with cats to outgoing e-mails, so far none have figured out out, and 37 have been arrested for bestiality...

I hear a guy named Mike Meyers made a lot of it happen in practice!!!

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