Why Yahoo! mail sucks

One of my pet peeves is why companies who have been around a long time are still unable to get the basics right. A great example is Yahoo! mail that,  even after 11 years of being in existence, can’t distinguish between legitimate emails and spam. It’s annoying enough when tons of junk mail gets routed to your inbox but the last straw is when legitimate emails get sent to your spam folder.

This interview with Mark Risher, anti-abuse product manager for Yahoo Mail in Network World on introduction of DomainKeys Internet Mail, as the standard for authentication, back in February makes it sound like the greatest invention since sliced bread. I found that there’s more truth in the comments than in the interview itself. 

This technology is something we felt would be very helpful for receivers so we can confer special privileges to a message. For this other message that lacks a signature, we can penalize it. We can treat it with more suspicion and run it through additional filters.

Yes, authentication of emails sound great in theory, the assumption being that Yahoo! system can identify the authentified piece of mail. But when their own mail system can’t distinguish between authentified mail and spam, what’s the point?

The incident that inspired my post today was an email I received from another Yahoo! mail user, a friend of mine who was responding to my previous email, and guess what?! His email was DomainKeys authentified and yet, it ended up in the spam folder. If I hadn’t checked my spam folder I would have missed the email with his flight details and would have left him stranded at the airport.

That’s why theory doesn’t always add up to reality and that’s where Gmail atleast has its basics right. Gmail system is smart enough to identify and compile emails in the same thread so subsequent emails in the same thread don’t get blocked. I mean, the fact that I’ve responded to a given email address multiple times should render it kosher.

That being said, how much can one expect from a free mail service but wait a minute…Gmail’s free and it’s not even out of Beta yet (which is curious, why is it still in Beta?). From what I’ve heard, the paid business mail hosted by Yahoo! has even worse spam filters, resulting in more spam than the free account, so much for paying for better service.

And as if it couldn’t get any worse, for the last few months, it’s been nearly impossible to log in to the mail account. You keep trying and trying, and you can see your emails in the tiny box on My Yahoo page but you can’t get to them. Yahoo! mail is supposed to be the third-most popular site according to Hitwise, a number which is no doubt helped by frustrated users who have to keep visiting the site multiple times because it’s so friggin darn impossible to get in.

Twitter and the conundrum of ‘free’ (social sites)

After a couple of highly frenetic work weeks and several crazy road trips later, I am finally back in the blogging scene.

Given the recent uproar over Twitter outages, the question begs to be asked (and answered), if you aren’t willing to pay for a service, should you be whining when it doesn’t deliver? What, if any, should your expectations be from a free service? Conversely, if you are a free site/platform, how do you justify additional investment in your company, if you don’t have any means of generating revenue?

This is a huge challenge for free social sites like Twitter. Good news is that you have millions of users, bad news is you have millions of users but no revenue. And if there’s no revenue, it’s heck of a lot more daunting to keep scaling to meet the needs of your burgeoning user base.

There’s where the venture funding helps, but sooner or later, Twitter (and free social sites like Facebook, Orkut, Friendster, and others) will have to figure out a way to make money. I think it’s quite dicey when the valuation of these social sites is based on freeloading users who don’t want to pay to use the site. Given that none of these sites like Twitter, Facebook have figured out a way to monetize this freeloading user base, the popular option seems to be advertising.

I have my own doubts about advertising as a sustainable revenue model for social sites. Especially, if the intent of any social site is to entertain and engage the user, driving them off the site with links to another site seems highly counterintuitive.

Therein lies the biggest challenge for these free sites, it’s all fine and dandy as long as the venture funds keep flowing in, all the site has to do is focus on getting more users (and of course, make sure the site doesn’t crash under all the traffic). Acquiring users for a free service is the easy part, but this story will get much more interesting when these free sites are forced to support themselves like some of the other ‘growed up’ social sites like LinkedIn.

Om Malik of GigaOM suggests charging power users like Robert Scoble, who according to Malik overwhelm the microblogging site. I think that’s a great idea, but how long do you think users will stick around if they have to pay for what they are used to getting for free?