The Hack Hustle: The Inspiring Story of the Slacker Behind the Woot-Off

Illustration for article titled The Hack Hustle: The Inspiring Story of the Slacker Behind the Woot-Off

You've certainly read Jason Toon's work: he's head writer for But you might not have thought about the staggering amount of copy he has to write. And the first time he did a Woot-Off, neither did he.

"Sounds like a great job, but is there enough work to keep you busy?"

This is what a friend asked me when I was hired as's full-time copywriter in 2005. I had to admit, I wasn't sure. Even by the variable standards of the copywriting field, it's an unorthodox job. Woot is an online store—you give us money, we send you stuff—but that's where any similarity to, say, Amazon ends. Instead of trying to sell all things to all people at all times, Woot sells exactly one product per day. The most succinct metaphor I've ever heard to describe Woot is "like the Home Shoping Channel in slow motion." One product per day means one product description per day—essentially nothing compared to the grind-'em-out catalog writing I had been doing before Woot hired me. On those jobs, writing a mere 15 product blurbs in a day would have been tantamount to calling in sick.


That workload disparity wasn't quite as yawning as it sounds, because Woot product descriptions are supposed to be free of cliche, jargon, and puffery, the three legs of the traditional copywriter's stool. The very first freelance assignment I did for Woot, before I was even hired, was returned by the CEO with orders to make the piece weirder, more negative, and above all, funnier. That's when I knew I'd found the job I was born to do. But just as in Tolstoy's line about how every unhappy family is unhappy in its own way, every crappy product is crappy in its own way. I learned fast that I couldn't just blow some marketing smoke, crib a few bullet points, and shoehorn in a few search-engine optimized key phrases and call it a day. Not at Woot, anyway.

But still. I'm not going to pretend it took me a solid eight hours to write every one of those caustic little mini-essays. Or any one of them, really. So at first, my boss found me various odd jobs to do to fill the time I was on the clock: writing auxiliary stuff like our FAQ, of course, but also moderating our discussion forums, or testing new site features, or monitoring the web for mentions of our company. I even dimly recall an agonizing period, shrouded in horror and shame, where I tried to sell ads on the site. That's when I knew I'd found the exact opposite of the job I was born to do.

In short, it looked like there wasn't enough work to keep me busy. The stretches of busywork gave me plenty of time to calculate how much less sense it made to the company to have me on the payroll instead of paying my freelance rate. If I had figured that out, how long would it take my superiors to reach the same conclusion?

But the pink slip never came. Instead, someone at Woot came up with an idea that would keep me busier than I ever thought I could physically endure: the Woot-Off.


* * *

The big problem with our one-deal-per-day model was, how can you grow from there? If you start adding other products, you lose the very thing that made you unique. You're just another second-rate online store. But if you don't start selling other products, you're locked into essentially the same revenue forever. The Woot-Off was one way out of this Chinese finger trap we'd gotten ourselves into.


Instead of selling one product per day, we'd switch to a one-thing-after-another model for a couple of days. There'd still only be one item for sale at any given moment, but as soon it sold out, it would be replaced by another one. No need to wait until the next day to see the next item. More germanely, no need to wait until the next day to buy the new item.

And even more germane to me personally was this brutal calculus: instead of one product description for that day, we'd need 50, or 75, or 100. Even with some help from our sometime second writer, it seemed impossible.


See, I'd never been what you'd call a highly-motivated, results-oriented, high-achieving type. I knew this. I knew I could never sustain the kind of workload that got you somewhere in life, not when I had the option of doing just enough to not get in trouble. And there was just no way I could write all that copy for the Woot-Off. This wasn't just a feeling I had, or a gnawing fear; I knew I couldn't do it, the same way I know my eyes are green and I get dizzy easily.

But I had a wife and (at the time) two kids depending on me. And I'd gotten the job through connections with some old friends, including Dave Rutledge, our Creative Director and the brother of Woot's CEO. These friends might never forgive me if I spazzed into purplish flames the first time my job asked more of me than a couple of languidly composed paragraphs a day. So I resolved to write until I collapsed.


Despite my low energy and general apathy toward the pursuit of excellence, I learned in Little League that "hustle" was the one quality you could will yourself to display, whether you really felt it or not. So I ran to first base on walks and ran out to my position at shortstop every inning and ran out even the most hopeless ground balls. I had to—I was a mediocre fielder, a terrible hitter, and my throws typically needed a hop or two to reach the first baseman. But at least I hustled. So my coaches were usually charitable enough to find a place for me in the lineup, talent be damned.

That was the only thing I could do for this Woot-Off. Hustle. When the ump called me out at first, as I knew he would, at least I'd still have my honor.


That morning would have looked like any other to you. Me, at my desk, pondering the minutiae of some hard drive or LCD monitor or robotic vacuum cleaner. You wouldn't have seen the crushing weight of the 25 product descriptions I had to write before I could claim my next sleep. I felt like I could barely breathe. I tried to commit every detail of my comfortable desk to memory, to savor during the unbearable hours at whatever my next job would be. I started typing, a doomed man, my doomed fingers dancing a macabre funeral march on the keyboard.

Run hard until the ump calls you out.

16 hours later, I still hadn't heard that call. I'd done it. I'd written every piece I was assigned to write that day, to my utter disbelief. It took every idea I had (and a bunch of ideas swiped from other people). It took every nanovolt of emotional and creative energy I possessed. It took, as I said, 16 hours. But I had done it. I had done the thing that I knew, knew, I couldn't do.


Along the way, I'd gained an enormous respect for hacks and hackery (in the old sense of cranking out anonymous creative work by rote, not in the computer-age sense). I'd always flattered myself with the self-designation of an "idea man", a superior intellect whose brilliant visions were too valuable to waste his time actually carrying them out. But as I pounded out those two dozen joked-up pieces of marketing ephemera, my awe only grew at the comic-book illustrators and pulp novella writers and dance-craze tunesmiths who just got the job done, in the days when their professions earned them no respect and not much more money.

Maybe these guys (and the occasional gal) fussed over their artistic integrity and stroked their bruised egos just as much as any other frustrated Stendhal or Gershwin. But if so, they didn't let it keep them from getting the job done. And judging by the results, we're just as likely now to hail the beauty and insight they brought to their work as we are to remember the names of their more pretentious, self-consciously artistic peers.


Before my first Woot-Off, I'd dismissed hacks as mere craftsmen at best. Now I hoped that one day I could legitimately claim to be one of them. If you think being a hack is easy, try it sometime.

* * *

If you've got even a little bit of aptitude for whatever you're trying – like maybe I do for writing and definitely do not for baseball—a conspicuous display of hustle isn't faking anything. Hustle is the thing itself. There's no such thing as fake hustle. Hustle is something you do, not something you feel. Whether you're doing it because you always have or to keep a job or catch the coach's eye, the effect is the same.


I've come through many more Woot-Offs since then. Always bleary-eyed and slap-happy and brain-dead, but I come through every time. Woot has spun off several other deal-a-day sites (another way for the company to grow without losing its deal-a-day soul). We've added a few more writers, and I now spend more time editing and assigning than I do writing.

But the Woot-Offs are still when I feel the most vital, the least replaceable. I still pull long, long days to get them done. And when that long list of products is finally all written up, I still feel the giddy, exhausted pride of the hustling hack.


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I sometimes feel bad for NOT reading the descriptions. In fact, I can't really remember ever reading a description save for the Adventure Crap one they had on 4/1 so that I could get my BOC. I've had good luck with them, but as of late, I have to admit they are starting to get actually crappy, mostly because they have like three in two months, so not a lot of crap builds up at their warehouse.