Why I moved from Gmail.com to Outlook.com

I recently moved my personal email from Gmail.com to Outlook.com. As most people know, moving email domains is a rather painful process and the last time I did that was about 8-10 years back when I moved from Yahoo.com => Gmail.com. So why did I do it?

The move was fueled by two factors

1. Poor experience on Google Apps leading to discovery of the awesome Outlook.com experience
2. Identity theft !! … or not?

Google apps 💔 startups

Google took a series of steps this year that were sort of startup unfriendly as part of their cleanup operations. That included shutting down Google Apps for Startups. It wasn’t an outright shutdown (that’s bad press right?). It was much a very sneaky move – they simply blocked any new ActiveSync devices from being added to a Google Apps Domain. So if you upgraded your phone like I did (iPhone 4 =>5), I was immediately cut out of my most important email mechanism. I understand the need to cover their costs, but I was seeing ads on my Google Apps Domain – so I presume they were monetizing my usage anyways. Even so, there could have been better ways to handle this transition (better alternatives, better customer communications etc).

So I was forced to look elsewhere and I noticed Microsoft’s Live Domains that offered hosted email (exchange servers) on a custom domain (eg: myname@mydomain.com). This is powered by the same technologies as Outlook.com. Note the “.com” at the end – Outlook.com the online service is like Gmail/Hotmail and has nothing to do with Outlook the Office desktop software.

Outcome? I migrated all our email domains to Live Domains and tasted Outlook.com. To my surprise it was really slick! This left a positive impression in my head. Add that to the good things Microsoft has been going within the startup ecosystem (Azure accelerator, BizSpark, BizSpark Plus, Startup meets etc), I was quickly getting impressed by Microsoft and weary of Google (though for search, I still prefer Google over Bing).

Identity theft (!)

Many of you know, my full legal name is “Siddharth Ravindra Shetye” and my gmail was “siddharth.shetye@gmail.com”. Over the last few weeks (or months?), random people started sending me accounting records, land deal records, purchase orders, tax returns etc. I would promptly delete all without opening to limit liability. Occasional I’d also email back asking them to stop mailing me. I even got some personal emails that appeared like conversations between me and my dad – conversations that never really took place between me and my father (I check with him too). But things started to get REALLY fishy when I started seeing purchase orders with what appeared to be my information (but not my my known credit cards). The physical address I saw for all deliveries was back in India (in my father’s home town) and by now I was pretty sure it was a scam.

First I wanted to limited my gmail exposure. Based on my previous Outlook.com experience (and Google’s sour taste) I wanted to host it on Outlook.com. And in the past, it’s been painful repeating my rather long email address verbally over phone or in person. So I knew it had to be short, leading me to pick “Sid314 (at) outlook.com”. Sid was unavailable so I added 314 (first 3 numbers of π or Pi, the irrational number).

Next I wanted to investigate this “scam”, so I asked “feet on the ground” to look into the address, physically, back in India. Turns out this is NOT a scam. In what must be the weirdest case of coincidence, here is the outcome of the investigation:

1. There is indeed a guy with the exact same legal name as me i.e. “Siddharth Shetye”. This is ok, I can understand that.
2. His father has the exact same name as my father.
3. His mother has the exact same name as my mother
4. They live in the same town as my father’s home town (Pune, next to Mumbai).
5. His email address is “siddharthRshetye@gmail.com” while mine is “siddharth.shetye@gmail.com”. If someone forgot the “R” in his address, I’d get it because gmail (stupidly) ignores “.”s
6. His father had an email address very very similar to my father’s.

I should have bought a lottery ticket that day. Anyway, the family was a well educated family and that Sid was a CPA helping businesses and individuals with taxes, deals and transactions. So at face value, there wasn’t a scam. Anti-climax, but one I’d prefer.

In Summary

Now that I’ve made the move, I’m actually very happy. Outlook.com is definitely faster than Gmail (custom domains or not) and to be honest, I needed a Microsoft Live ID  to manage several of our cloud resources hosted on Microsoft’s datacenter and also have one for my Windows 8 login. Anyway the move itself was painless and if you’re interested, it’s documented here.