The Last Word on Datapimp

datapimp, often imitated, never duplicated

Almost a year and a half ago I wrote up a little summary of datapimp, the weird email and website hosting business that I ran for nine years.

I recently found a history that I’d posted (on June 3rd, 2007) while datapimp hosting was still active, and it’s much more ridiculous, offensive, and misguided than what I wrote here. (At first, I typed “youthfully misguided,” but I was hardly a youth at the time, so I can’t blame that.)

But since it was ridiculous, offensive, and misguided, naturally, I thought it was worth archiving. Though “archiving” sounds kind of fancy and academic for something that sprang from the gutters of Los Angeles the way datapimp did.

The article reminds me that at our peak, we managed half a million free email addresses! For some reason, I’ve always remembered that as a quarter million. And it’s absolutely true that two agents from Scotland Yard came all the way to Pasadena to talk to me. I handled all those kinds of things for datapimp, so I was on a first-name basis with a few local FBI agents.

As an added bonus, the article characterizes the man who hired me for my current job as, “a mad bastard,” “tireless and effective, like a shark who will die if he ever stops moving forward,” and, “ambitious and insane.”

I wouldn’t necessarily take any of that back 😉, but that should give you some idea of the tone of the article.

This 2,000-word-long block of text was originally broken up with distinctive old datapimp images, none of which I have anymore. Sorry.

A brief history of the majesty that is datapimp

In which our heroes admit failure and defeat much more frequently than glorious triumph.

In April of 1999 I registered the domain after seeing attached to a customer’s account at the hosting joint I worked for. Yes, the datapimp name was pilfered. Don’t act so surprised. Mediocre artists borrow, great artists steal. Everyone knows that.

Where were we? Ah, yes, we were sitting in shitty chairs at shitty desks in a shitty afterthought of a building above an auto repair business, working for Affinity Hosting in glamorous Gardena, California.

It may shock and sadden you to know that here were no “on campus” cafes, swimming pools, fleets of Segways or company masseuses in the early days of web hosting. The industry became very rich very quickly (through investments for the most part, not actual selling of services) and became a comically bloated self-parody, but early on many of us worked in virtual sweatshops for half-mad bastards who thought nothing of firing you if you objected to working 21 consecutive 16 hour days.

A few months passed while I wondered on and off what to do with Then one day a genuine twentieth century miracle occurred. The sun shined down through a crack in the clouds and new domain registrars were born.

Why is that important? Because in the dark ages before registrar competition, there was only one registrar of .com, .net and .org domains, Network Solutions, and they prevented the registration of any interesting domain names.

The morning the new registrars came on line I found the cheapest one ( and tried to register In what seemed like a terrible mistake on their part, the registration went through (they emailed me a few hours later saying that someone else beat me to it by a few seconds, so it was not destined to be ours).

The handsome young Steve D. was sitting a few feet to my left, and I said to him, “Hey, I just registered!” Flush with the excitement of newfound digital freedom we registered a few more domains, including and, just because we could.

Once it became known that slimy miscreants such as ourselves were registering these domains, a minor flap ensued, and some members of the “community” argued against allowing the registrations. To their credit, the geeks at said, “Screw you!” Or rather, “If it’s all the same to you, we’re going to allow freedom of speech as far as our business is concerned.”

The hubbub eventually rose up through the organization that oversaw the new registrars, and they ruled that censorship, or the lack thereof, was up to the individual registrar.

So there we sat with the new domains, wondering what the hell to do with them. After a particularly long three margarita lunch one Friday, the idea to use some freebie Affinity accounts to sell email addresses surfaced, and being idiots, we considered it to be a genius idea. After all, we had the perfect umbrella name to sell them under:

On closer inspection, without the aid of powerful Mexican liquor, it was clear that using Affinity accounts wasn’t going to cut it (in those days a “premium” account had a 50 megabyte storage limit, and cost $50 a month). We wanted to do the email hosting right, so we “borrowed” an unused Cobalt RAQ server from Affinity and set the clunky fucker up to handle our new email business.

We started by selling the addresses, and though it might seem unbelievable now, people actually bought them. A lot of people. POP accounts were $24.95 a year, forwarding accounts $14.95, and the orders came in steadily, all day long.

Which meant that we soon outgrew the piece of shit RAQ server and had to spring for some real hardware. It was around this time that we brought Brad S. into the fold, since he knew how to write the code needed to run the pimp and we didn’t really know how to do anything.

We bought a big new server and Brad set about improving the system. We also had help from Donald S., but he really doesn’t come into the story until a bit later. Let’s not get ahead of ourselves.

Here’s a big, fat mistake you can learn from:

If you plan to buy a .com domain from someone, don’t set up a business on the .net version first.

The kid who had the .com never did anything with it, but when I told him I wanted to buy it, suddenly there were “a few people” interested in it, and wouldn’t you know, they were always willing to pay a couple hundred bucks more than I offered. Funny how that happens.

I finally got the conniving little prick to part with it for a couple grand. You know you’ve reached a fair price when both parties are chuckling to themselves about how they just screwed each other over.

We continued to sell accounts for a while, registered the company as an LLC, and expanded into arcane services such as URL forwarding. For reasons which seemed sound at the time, we flip flopped between pay and free forwarding, pay and free webmail, and other things I can barely remember. Which leads to another lesson;

Make up your fucking mind, and stick to it.

People who use internet services generally dislike change. They dislike it the same way they dislike genital herpes, or income taxes. Stability of purpose is your friend. Dare to be stagnant!

Eventually, under the delusion that life and business consist of nothing but endless possibilities, we decided to give all the email services away for free, in order to accumulate a huge database of people we could sell other shit to.

What other shit, we weren’t exactly sure, but it would be cool, right? That’s how we found ourselves running a free service.

This is where things get a little weird. But remember what Hunter Thompson taught us;

“When the going gets weird, the weird turn pro.”

The system that ran the datapimp forwarding addresses was pretty simple, and account set up was automated, so after the last of the paid accounts died off, the pimp pretty much ran itself. At any given time there were 200,000 to 300,000 active accounts. The most we supported at one time was half a million.

Chicken feed to some, I know, but that’s a lot of email bouncing off the servers, and when you handle that much email there are problems. Spam problems that get your servers blacklisted, visits from the FBI and Scotland Yard (true) and other groovy adventures you never knew existed.

So for about a year the pimp just hummed along in the background, and we sort of ignored it. But it couldn’t just fade away like that. It was always in the back of my mind, tormenting me like a ghost in one of those stories they tell you as a kid to scare the shit out of you on a camping trip.

So in 2004 I contacted Donald S., who was the best UNIX guy I knew, and offered him a significant share of the company if he would develop a web hosting system we could charge people actual money to use. He said, “Hell yeah!” and datapimp hosting was born.

Sort of.

Lesson #1794: You can’t choose your family, but you can (and should) choose your friends – and business partners – carefully.

So began an almost three year nightmare of trying to convince my partners to commit to the datapimp way and make some things – or anything – happen.

A lot of things kind of happened, or almost happened, but never really fully happened. The web hosting system was always “almost finished,” while the big clock in the sky tick-tocked away and we all got older and less handsome.

During this time the email forwarding was still working, but it began to unravel. The system was old, we were constantly being blocked, technical changes in the way email works were starting to be adopted by the big boys…things were falling apart fast.

I tried to rally the troops, to get the partners to see that the pimp was circling the drain, and if we didn’t do something, it would spin down into the Los Angeles sewer, never to be seen again. But they had bigger fish to fry, apparently. They didn’t seem to have even a passing interest in doing anything with the pimp, which made for a bleak forecast.

Donald had a new job (where, in his online employee profile he claimed to have founded and single handedly run datapimp, which may have been funny except for the fact that it made me want to hunt him down and murder him in his sleep), and Steve and I had been at PowWeb hosting for a few years, at desks a few feet from each other, just like the old Affinity days.

But then PowWeb was sold and everyone with any sense was fleeing that sinking ship. Steve went to Dreamhost and once he was out of sight, he may as well have dropped off the face of the earth.

Both of my boys were incommunicado. It would take days or weeks to get a call or an email returned. But I continued to try to shore up the sagging pimp.

And then I gave up.

Which may be the first smart move since deciding to sell obscene email addresses to a young internet.

Well I didn’t give up, exactly. But I gave up trying to motivate my partners.

I moved the domains to another registrar, and all the site content to new servers, effectively breaking up the band. You would think that two guys who did all they could to avoid and ignore datapimp would be glad to be rid of it, but it didn’t quite go down that way.

They were angry. Steve wanted domains, Donald wanted domains, suddenly the pieces of datapimp were very interesting and valuable to them. It was an unpleasant divorce, and I think Steve still wants to castrate me with a rusty scissors and a melon-baller, but the core of datapimp remains as it is, intact and insane, pirate style!

In moving and breaking up the company the painful decision to pull the plug on free email forwarding had to be made. It lasted almost seven years – uninterrupted, baby! – and that’s pretty damn good in my book. Besides, we replaced it with something better, free datapimp blogs (and email forwarding is still available on the blog domains as part of premium forum membership).

But once the cord was cut, I really wanted to get web hosting off the ground to show those lazy pigfuckers how it’s done. So I needed someone who was the opposite of Donald and Steve, and that guy was Tom.

Tom also worked for PowWeb, but not in the Los Angeles office. I observed the mad bastard over a few years tackling project after project, tireless and effective, like a shark who will die if he ever stops moving forward.

So when I started to think of who I could bring on board that was ambitious and insane, it was a short list, and Tom was the only name on it.

We did some complex statistical analysis (fingers and toes) of what the most popular datapimp domain names were, and set up the lean, mean datapimp V2 that dazzles and mystifies the masses today.

So after years – literally – of trying to get the old guard up off their asses, within less than a month Tom and I had the first datapimp web hosting services up and running. Which leads us to;

Lesson #51936: Nothing is as difficult as they would have you believe.

Well, some things are still difficult, but believe me, if you’re motivated – by fear, death, entropy, dismemberment – choose your own terror – you can get shit done.

Which brings us to the present. The present being datapimp V3 looming on the horizon. It’s not a major change, still web site hosting (and ?), but we’re retooling and refocusing and aiming our death ray right in your direction Jack, so get ready to take out your wallet. We’re coming for all your gold, and we won’t rest until we get it.


There was a postscript to the article listing all 219 domains we offered as email address domains at datapimp (which had been pared down to about 19 by the time I wrote the article). I’ll spare you the wonder and joy of reading that.

Here are a few of the different looks the site sported over the years.


datapimp 2005


datapimp 2007

And the (broken) original blue monster, from 1999

It’s strange to see some of these domain names. My memory of early datapimp was that the domains were all (aside from the shock value “fuck” domains) clever or funny. Clearly my memory is a liar.

All I can say is I didn’t register all of these. I had partners. And we also registered user requests. So whatever stupid thing someone suggested, we’d say, “Why not?,” and offer it.

If we sold one POP account on a domain the domain was paid for, so I guess we figured,

datapimp 1999



  1. You had the best email addresses in history! I was so unhappy when they eventually got taken away. There is no service available anywhere on the internet anymore that does what you did.

    Here’s my favorite ones that I created:

    These email addresses were FANTASTIC to give out to people at bars & nightclubs.

    Girl: “What’s your email address?”
    Me: “Nice Tits @ Wanna Fuck .net”
    Girl: “What?!?”


    • There is no service available anywhere on the internet anymore that does what you did.

      Well, that’s for sure. 😉

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