BUYING TICKETS TO A SHOW or a sports event is easy. Just go to one of about a zillion Web sites, find the event you want, and plug in a credit card number. Reselling those tickets isn't much more complicated: Post them on eBay or craigslist and set a price. But trying to make a killing on those sales is about to kill me. I've spent the past three mornings tinkering with the price of a seat at Dodger Stadium in the heat of the pennant race. I can't figure out how to unload two tickets to Justin Timberlake's show in Sayreville, New Jersey. And I'm having panic attacks about the Cheetah Girls' ability to fill a 5,000-seat hall in Denver.

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It is day 16 of my 38-day attempt to conquer the secondary ticket market. I'm buying tickets to concerts and games and then, using a bunch of online tools, trying to sell them at a profit – it's kind of like daytrading. I coaxed my editors at Wired to give me $500 of seed money (initial suggestions of going to Vegas and putting it on black were met with skepticism), and I dove into the shadowy world of online scalping.

Where do tickets come from? There's the box office at the venue, obviously. There are the guys outside the stadium. There are the high-priced ticket brokers. And, of course, there's the $950 million-a-year, globe-spanning Ticketmaster. But new options have recently emerged to destabilize that ecosystem. StubHub, a Web site set up by two Stanford MBA students in 2000, lets individuals buy and sell tickets like brokers. Craigslist, eBay, RazorGator, and a host of other sites offer similar services. The global online aftermarket is estimated to be worth up to $3 billion.

And it's a market that anyone can play. It's a snap to buy four tickets to Paul McCartney at the nearest arena, sell two online for double the price, and treat your "Band on the Run"-loving significant other to a free night of silly love songs. But actually trying to make a living at ticket-trading is more complicated.

ON THE FIRST DAY, I CALL BRETT, a case manager for a Boston organization who runs Sitting Pretty Tickets on the side. He becomes my patient and insightful scalping adviser. Brett is 29, unmarried, and spends $20,000 to $30,000 a month buying tickets. ("I put those on credit cards to earn rewards points," he says. "It helps me make vacation plans.") Brett won't tell me how much he makes at this game. Futhermore, to avoid angering the teams he has season tickets to, he asks that his last name not be used. "Ninety percent of what I do makes money." He calls what we're doing "flipping."

There's nothing magical about the strategy: When the Kansas City Royals finish in last place four years in a row, demand for their games is low and prices drop. When metal supergroup Audioslave opens a tour in clubs instead of 15,000-seat arenas, supply is low and prices spike. Successful ticket traders have to do their research (did the Stones oversaturate the market last time around?) and fine-tune their instincts (can Tarzan possibly do as well on Broadway as The Lion King?). Do it with enough finesse, Brett says, and a daytrader can make a few thousand dollars a month. But every purchase ought to be based on a sound calculation of supply and demand. "Generally, you don't want to buy a ticket just to buy a ticket," Brett says.

Got it. Brett counsels me to buy Justin Timberlake, who's now selling out 1,000- to 3,000-capacity clubs and has an arena tour slated for early 2007. I check Ticketmaster.com. Timberlake tickets don't go on sale for another three days. I start clicking around. Ten minutes later I spot James Blunt, the British sensitive-guy singer-songwriter who had a hit in 2005 with "You're Beautiful." Can't miss. Plus, there's a secret presale you can access with a password hidden on Blunt's Web site. I find the password and score two tickets at the back of the floor, in front of the sound board. Just $56.90 each. I post them for sale on StubHub.

Next stop: sports. It's summer, so I use my baseball instincts – finely honed from playing the Dungeons & Dragons-meets-fantasy baseball game Strat-O-Matic in the '80s – to prognosticate the pennant races (badly, it turns out). Yankees and Red Sox are out – demand and prices are too high. But the Dodgers site shows field-level box seats for a home game against the Padres for $98.28 each. With no idea how much they're worth, I buy two.

I check in with Ram Silverman, VP of the 18-year-old ticket-reselling company Golden Tickets, in Plano, Texas. Silverman rips apart my tactics. Of Blunt, he says: "It's a toss-up – those types of seats don't typically sell that well because they're too far back on the floor." Of the Dodgers, he thinks I paid too much. "$100 apiece? That doesn't sound right. Face value on a baseball ticket shouldn't be $100, especially for that type of seat."

So will I make money on these? "No," he says, then pauses. "I could be wrong."

It is day 4, and I've decided to bank on Justin Timberlake to paper over my mistakes, just like he did for his bandmates in 'NSync. I have $189.64 left, and I hit Ticketmaster.com at precisely 8 am for the Roseland show in Manhattan. After half an hour of reloading the Look for Tickets page and plugging in various nonsensical security words – "ashler," "conics," "dogfox" – I give up. Later that day, Philadelphia goes on sale. Same result. But Sayreville comes through. Not one but two tickets come up, for the September 1 Starland Ballroom show, at a very reasonable total of $108.30.

Now I have to figure out what to charge. This is complicated. I check StubHub, hoping to glean some kind of market report. No such luck – Timberlake prices are all over the place, from $63 to $207. Nobody's touching them on eBay. I list mine for $150 each.

On day 7, something wonderful happens. A kind soul in New Jersey buys my James Blunt tickets for $90 each. Minus StubHub selling fees, that's a total profit of $40. In your face, Ram Silverman!

But my Timberlake tickets aren't moving. I drop the price. I call Brett, who sheepishly acknowledges it's hard to peddle general-admission tickets. Inexperienced sellers online slash prices, skewing the market downward. Thanks, Brett. Another broker checks his national database for me and finds a very high number – he won't say how many – of Timberlake tickets available around the US. That's bad.

Then I act on a tip from another broker. A trip to Target nets me the new CD from teenybop sensations the Cheetah Girls. In the liner notes is the password to a presale; I buy two tickets to a show at the Colorado Convention Center for $102.25.

AS LITTLE AS SIX YEARS AGO, being a ticket-reselling professional was a lot less trouble. There was no StubHub, the eBay ticket market had yet to ignite, and brokers were the only people who could produce those front-row Britney seats you needed at the last minute. Pesky amateurs like me weren't part of the equation.

Of course, the best brokers have figured out how to take advantage of the new landscape. I've heard stories – perhaps apocryphal – about a computer program that automatically plugs the security word into Ticketmaster.com. "I know how to navigate the Ticketmaster Web page five times faster than you do," says David Burgess of Great Tickets in San Antonio, Texas. "You go there maybe once or twice a year. My people go there once or twice an hour."

In fact, reselling is so hot that the stigma is gone. Ticketmaster has deals with Madonna, Bon Jovi, and most sports teams to participate in online auctions. At least 17 states have laws limiting the profit you can make from reselling tickets, but none apply if you live out of state. And they're rarely enforced, whether you're a national brokerage or, um, me. Meanwhile, Ticketmaster, StubHub, and others are lobbying to make the whole thing legal nationwide.

And why not? The ticket aftermarket tells everyone – fans and promoters alike – the real-time value of an event, a layer of market transparency made possible by the Internet. Today, music pros gossip about artists who check their StubHub prices via wireless laptops on tour buses and demand of their managers and agents: Why can't we get some of that?

Day 19: I'm sitting in an airport, surfing the free Wi-Fi, when I learn that Justin Timberlake is the hottest thing in New Jersey. There are only two pairs of tickets left on StubHub, at more than $280 per ticket. My tickets are suddenly getting tons of action on eBay. Unfortunately, I've mistakenly listed them for sale twice. I can't figure out how to cancel an eBay auction, and I have to board, so I quickly bid up the lower auction using a second eBay account, thinking $110 should be enough to scare off any buyers. I forget about it and get on the plane.

Big mistake. Next thing I know, "doblefam" swoops into the $110 auction and purchases the tickets for $112.50, while the other auction is up to $152. I apologize to doblefam and explain how I mistakenly posted the tickets twice, and that I tried to make up for it by outbidding everyone. The response: doblefam's mother is a lawyer who will sue me. We exchange not-so-nice words, and there ensues a tense 12 or so hours. Later, I get a warning from eBay about "shill bidding." (Apparently, everyone but me knows that bidding up on your own auction is not kosher.) Fortunately, doblefam disappears and a nice woman named Christine wins the second auction for $177.50.

Not only that, but my other offerings are starting to move, too. A Denver mom snags my seventh-row Cheetah Girls tickets for $153.95. The Killers, appearing in Chicago, sold at $132.50. (I bought two for $84.88.) Now all I have to do is dump the Dodgers seats. Silverman was right – it's hard to make a profit off the cavernous Dodger Stadium. On day 37, somebody on eBay bites for $151.53. That's my only loss. After eBay fees, I'm left with $732.

Still, I feel kind of rotten about being a scalper. Morally, it's dubious. Last summer, Tom Petty's manager abruptly invalidated more than 1,200 tickets to upcoming shows in St. Paul and New York after he realized scalpers had infiltrated his fan club to get the presales. "I'd get rid of all scalpers," says Jerry Mickelson of Jam Productions, which promoted the Petty show. "That's fairest to the fans." But then there's Madonna and Barbra Streisand, whose official prices go sky-high as their secondary market heats up.

Looking for absolution, I ping one of my victims: "Christine" turns out to be Christine Hahn of Metuchen, New Jersey, a marketer for a mall and mother of a 21-year-old Justin fan. "They sold out in, like, a matter of minutes," she says. "I had no idea he was even going to be in the area. When I called in, it was impossible to get tickets." So she went to eBay and found me. "I don't think I would purchase off the street, but I guess I don't see eBay as being the same scalping-type thing." Hahn's daughter, Samantha, lined up for the show at 5 pm; Timberlake didn't hit the stage until 10. She had a great time.

One issue remains: What should I do with the $732? Part of me wants to reinvest for a big score. Broadway? Nascar? My editor suggests we donate the profits to charity. I don't tell him I have a better idea: Put it on black, baby.