6 things that killed Waifmail

With all the success stories about Expat Software and Blogabond that I've been telling lately, you might get the impression that it's all blue skies every day here. I thought it would be good for balance if I told the story of one of our spectacular failures.

Back in 2004, Waifmail was positioned to be the great Outlook killer. A web based mail client from which you could read all your email from all your myriad accounts, all in one place. All on one screen. It was pretty cool.

Waifmail died before it got off the ground for a number of reasons that are too complex to go into here but… Nah, screw that. it died for 6 specific reasons that I'll outline below. In actuality, it died for one single reason: GMail. But it sounds more interesting if I break it up into a bunch of bullet points instead.

6. Small target audience

As you might know if you've been reading this blog, I travel a lot. As a result, I often find myself in some sweaty little internet café in rural Laos, waiting 20 minutes for Hotmail to load up the "Hey, you have some mail" screen. Followed by another 20 minutes to load the screen where it actually shows you that mail. I have 4 email addresses that I like to keep up with, so every visit to the internet café involves a dozen Internet Explorer sessions open at any given time, all fighting for bandwidth over the single shared AOL connection that the café is using.

My first big mistake was assuming that there was at least one other human being on the planet with my same problem. To be fair, there were probably a few. But they were stuck in some dingy Cambodian internet café, and not likely to find this thing. Especially true due to our...

5. Really sad marketing

To be honest, I can't even remember what our marketing strategy was for this thing. Something along the lines of "Put a link on the Expat Software site and let Google find it." I might have mentioned the site in a few posts to the Usenet, but we never really seriously marketed the thing and certainly never paid for any advertisement. I think it was the classic case of the geek in the basement (or jungle as the case may be) writing his perfect app and then sitting back waiting for the world to find it.

Nobody did.

4. Poor technology choice

I know it's lame to blame your crappy software product on a crappy development platform, but I think we were really hampered by our decision to go with the LAMP stack for this thing. Specifically, PHP.

I'd done a fair amount of PHP development by this point, and had built a set of tools that let me work pretty well from a public internet terminal. My little DHTML IDE and file management utilities worked so well that when I took off on my 9 month road trip, I left the laptop at home.

I did some research before starting development on Waifmail, and it seemed like PHP had a pretty decent mail library built in, and another beefier one waiting to go in PEAR. I come from a Microsoft background, and you can say what you want about Microsoft, but their development tools and libraries are rock solid. If they have a library called System.Web.Mail, you can rest assured that it will actually send emails when you ask it to. Unfortunately, this is not the case with PHP.

First off, the IMAP_whatever functions in PHP simply do not work. It's incredible that there are four separate ways of opening a mailbox and none of them will actually open a mailbox. Check out the documentation over at php.net. It's unmitigated comedy, as dozens of developers hand out advice in an attempt to get the library to function at all.

Next up was PEAR, which is at least capable of sending an email message. Too bad it doesn't offer much help in connecting to a mail server and reading your mail. Looking around the PEAR site today, it seems that people have at least been adding to it, so it's possible that there is a functional library in there somewhere. Though in standard PHP fashion, you get multiple semi-redundant libraries piled on top of one-another with no naming standards.

So, as a last resort, I wrote my own IMAP and POP clients in PHP. Not any fun to do, and certainly an unwelcome piece of work since it was the one thing I figured I'd get for free from the platform.

3. Reliance on shared hosting

This was another visionary move that turned disastrous in a hurry. The plan was to rely on constellations of cheap $5/month shared boxes, easily adding more capacity as demand increased. Seeing as how we've gotten about 40 signups in 3 years, we never needed to put this grand scaling vision into place, but it woulda' been cool I tells ya!

The problem with this scheme is that we lost control of the environment. MySql would put out a release, our host would upgrade the servers, and something at Waifmail would randomly break. New versions of PHP would come and go, with different global settings in place, and suddenly we'd be living in the world of "Magic_Quotes_Runtime" and everybody's mail would have slashes all over the place. We'd wake up to find the site on another box that didn't have the PEAR libraries installed, and suddenly mail would stop sending. It became a lot of work just keeping track of this stuff.

Eventually, the whole hosting company got sold and the site ended up on another box with a different configuration. That's about when I gave up paying attention. I'd be surprised it Waifmail were even functional today.

2. Impossible to gain users' trust

This one stopped us dead in our tracks. Try it out some time. Put up a new website and ask people to type in their email address and password! That's really the only way we can log into your mail server to show you your email, but really, who in their right mind would give out this information? Maybe if you're Google you could pull this off, but for an unknown site just starting out, this simply killed us.

I knew it wasn't gonna work the day I tried to demo the site to my sister. I showed here the signup page and told her to put in her email address and password.

Lisa: "My Email address? My company doesn't really like me to give that out."

Me: "But you're not giving it out. You're just using it to read your mail."

Lisa: "Yeah, but still… If they found out I think they'd be mad."

There you have it. We're fucked.


This all happened in the winter of 2004. Now sometime around April of that year, this company Google put out their own email service called Gmail. Perhaps you've heard of it.

Gmail did roughly everything that Waifmail had set out to do with the sole exception of letting you read your Yahoo, Hotmail, and work accounts through their reader. But you knew that was coming soon. And when it did, any little company trying to do the same thing would be out of luck.

Fortunately for us, we had already thrown in the towel.

Jason Kester

I run a little company called Expat Software. Right now, the most interesting things we're doing are related to Cloud Storage Analytics, Online Classrooms, and Customer Lifecycle Metrics for SaaS Businesses. I'll leave it to you to figure out how those things tie together.

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