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What’s the Technology Behind Ask Leo!?


I was just curious about your site and news letter. What type of hosting do you use? Did you “hand craft” your site or use a CMS like WordPress or SquareSpace? How do you create your news letter, such as what application do you use?

Can you give us some background information on “What goes on in Leo-ville?”

Keep up the good work. Always look forward to the Friday Facebooks and news letters.

Well, we have to start with being careful when you say “Leo-ville”. “” is actually the website of the “other” Leo, Leo Laporte of and other netcasting fame. We’re both in tech, we both try to help people with technology and we’re both named Leo, but we’re definitely not the same person.

With that out of the way, sure, let me give you a peek behind the curtains of Ask Leo! world headquarters.

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The Ask Leo! website (and and a number of other variants) are all hosted on a couple of virtual servers out at StormOnDemand, a service of LiquidWeb, a large hosting company. I’ve been very happy with Storm and LiquidWeb and have been there for several years now. The server is physically somewhere in Lansing, Michigan, I believe. The virtual servers are the equivalent of a complete PC that I manage and access remotely from wherever I happen to be.

Each server runs the CentOS operating system, one of the popular Linux distributions, in this case targeted specifically at server operations.

Ask Leo! on is running WordPress, while the older is running MovableType. Rather than transition everything at once – a massive undertaking – I elected to move to WordPress incrementally. Articles are slowly being moved from the old domain to the new. (This has been underway for about a year and a half now. I doubt that the old domain will ever go away completely.)

WordPress runs a custom theme – the “look and feel” – that I had developed for me. I’ve since tweaked the theme some, as well as written a few custom WordPress plugins to get things just the way I want. Naturally, like most WordPress sites, I run a variety of plugins to add or modify functionality on the site.

The Ask Leo! newsletter

The newsletter is where things get more handcrafted.

To begin with, I’ve written some custom PHP that my assistant or I runs usually a couple of days before the newsletter publication date. The PHP automatically picks up the approriate content from the website (or sites, since it also picks up from as well as, both also WordPress sites) adds a couple of items like the weekly advertisement or my additional comments, and then runs that against a template to create the final newsletter HTML.

That HTML is then simply copy-pasted into Aweber, my (highly recommended) newsletter sending service, where it’s scheduled to send every Tuesday at 8AM Pacific.

The Best Of Ask Leo! mailing

The Best Of Ask Leo! mailing list is a little different. It’s not truly a “newsletter”, but rather what’s called an “auto-responder”.

On the day you sign up you get issue #1. Then each week thereafter you get issue #2, #3 and so on. As I type, there are something like 130 issues in the Best Of sequence of emails. The trick is that it’s all based on when you sign up. People that signed up a year ago are getting issue #52 right about now. People that sign up today start at #1.

Everyone gets a hand-selected article from my archives; they’re just not all getting the same one at the same time.

The hand-selection works a lot like the newsletter. I manually choose (indeed, I do “hand select”) an article to be added to the sequence, perhaps update it a tad if needed, and then run another custom PHP script that runs it against a template to produce the HTML I can then copy/paste into Aweber.

Asking a question at Ask Leo!

As I’ve said many times, I get a lot of questions. So many that I have to put some structure around how they’re managed between myself and my assistants. Once upon a time I used a custom PHP interface that I’d written myself, but a couple of years ago I switched to a different service: ZenDesk.

You may have already used ZenDesk elsewhere and not known it. It’s a service that is specifically designed to handle customer support or “helpdesk” requests; specifically, when a customer contacts a company and a “ticket” is created that is then updated and communicated back and forth as the support request is handled.

It dawned on me that this ticketing is pretty much what happens to Ask Leo! questions. So now when you enter a question at it automatically creates a ticket that we then track as the question is processed by one of my assistants (filtered for spam and common answers) and eventually assigned to me for review.

Not to minimize what I do, but in a way Ask Leo! is really not much more than a help desk (i.e. the question submission form) and knowledgebase (the thousands and thousands of articles already published). It makes sense that a ticketing system would work well, and it has.

The View from Ask Leo! World HeadquartersA word about that “World Headquarters” thing

I love using the phrase “world headquarters” because it’s exceptionally ironic.

Ask Leo! absolutely serves the entire planet – I get visitors from every corner of the globe. And yet “world headquarters” is wherever I happen to be that has an internet connection.

Mostly, that means here in my home in Woodinville, Washington. Last week Ask Leo! World Headquarters was a travel trailer parked in a state park on the Washington Coast. Earlier this year “world headquarters” spent a few days in Maui, and later this year it’ll travel to Montana for a couple of days, as well as Palm Beach, Florida.

It’s yet another reason I love what I do. I can do it just about anywhere.

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Footnotes & references

PS: Yes, the beach and rainbow photo is one I took myself. It’s the view from Ask Leo! World Headquarters, while it was in Maui earlier this year. :-)

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