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Work · September 22, 2011

CO

Check out my (sort of) weekend project...

Check out my (sort-of) weekend project . . . And by weekend project, I mean something that I thought sounded like a small idea that I could throw together over one or two weekends, but ended up taking over six months. This is a bit of a long submission, but after lurking on HN for the last few years, I thought this might be a chance to contribute something back. I’m just going to briefly discuss why my “weekend project” took so long, and how I got where I am. The url is http://dudmail.com - it's a disposable email site. Similar in intention/scope to the many existing ones out there, but…

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In the maker’s words, at launch

Check out my (sort-of) weekend project . . . And by weekend project, I mean something that I thought sounded like a small idea that I could throw together over one or two weekends, but ended up taking over six months. This is a bit of a long submission, but after lurking on HN for the last few years, I thought this might be a chance to contribute something back. I’m just going to briefly discuss why my “weekend project” took so long, and how I got where I am. The url is http://dudmail.com - it's a disposable email site. Similar in intention/scope to the many existing ones out there, but hopefully differentiated a bit based on how long we keep the mail (two weeks), and by accepting attachments and optionally forwarding the email onto a personnel email address. (And of course, by being mine =) After being inspired by all of you that seem to be actually getting ideas off the ground, over the last couple of years I had tried (and failed) to get two or three other application ideas to succeed. One reason they failed was that my ideas were far too ambitious for me to pull off. Their scope was so large that I could never finish them off, and I never felt they were ready to be released. It took a year or so (or more) before I was ready to give up on each idea, so this was a huge waste of time for me in terms of not failing often/early. Identifying this large scope issue as a failing, I thought that a disposable email site was such a simple concept with a single well defined focus (ie email) that I should be able to knock something together quickly and actually get something released... Why did it take so long? There were a few reasons... The guts of the site were actually thrown together pretty quickly - not much longer than my naive ‘weekend or two estimate’. The bits that let me down were: - learning how to render a million different types of email sanely (still in progress). - trying to learn how to bend postfix to my will (achieved) - learning how to make a site design that didn’t suck (sort of achieved) - trying to work out why my application keep falling over (problem avoided) - fear of actually releasing it / considering it finished. The site was created using Ruby on Rails - it has a really simple database schema and it was all pretty straight forward. The biggest problem was rendering email - this turned out to be far more complicated than I expected. Plain text email is simple, but then you have to handle html mail, multi-part mail (text and html parts!), base64 encoded mail, mail in any one of a million different character sets, email with attachments etc etc. For html mail, you need to be able to render it within the css hierarchy on your page, without impacting adversely how the email was meant to be display. For emails in a odd unicode character set, you need to ensure you’re handling and storing it correctly for every step of the process, or the end result will not be pretty. Rendering email correctly was one of the hardest parts of this site, and I’m still finding types of mail that I’ve not yet encountered and haven’t handled yet. Postfix was a real problem as well - I’d never really dealt with it before, and what I was asking it to do was pretty far out of the ordinary. I wanted any email, coming to any email address, on any subdomain, on any valid domain to be forwarded to my Rails instance for processing. This was strange enough that fine folks in #postfix were hesitant to help me because of the 'overwhelming amount of spam' I could expect to receive. I was expecting 99.999% of emails to be spam, so this was cool. In the end after many many hours, I was able to make it do what I wanted using virtual_alias_maps and some very generous regular expressions. Any email coming in gets forwarded to an alias, which then pumps it directly into the rails webserver as a POST request (to avoid firing up a rails instance for each email) The next issue was that of design - I’ve never been competent in this area. Initially I…

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