(MONEY Magazine) – When I was 12, my dad gave me 10 shares of IBM. Pointing to the columns of tiny numbers in the business section of the Sacramento Bee, he explained that at $66 a share, the total cash value of my "portfolio," were I to sell, was $660. As in six hundred and sixty dollars. Cash money. Mine. All mine. I was giddy, my orthodontia flashing for the world to see. The potential impact on my Hot Wheels collection was not to be underestimated. I was, in the parlance of the day, hella rich.

But I never sold, and thanks to 20 years of stock splits and dividend reinvestment, my stake in Big Blue (as I'm now fond of calling it) is valued at nearly $10,000. Not too shabby, right? Then in February of this year, I was talking to my 16-year-old cousin Jack, who told me about his first stock market experience at the comparatively old age of 14. Last year, Jack told his dad--my uncle--that he wanted to invest in a company called GeoCities when it went public, largely because Jack had built his Web page using GeoCities and thought it was a really cool company. How cute is that? Jack suggested that they take the $7,000 they were saving for his first car and buy the stock. After some discussion, his dad agreed. Six months later, without the benefit of any stock splits or dividend reinvestment, Jack's stake in GeoCities hit $21,000. He sold the stock and bought a Ford Explorer. A real one. He paid cash.

I was still absorbing this a few days later when my editor called to tell me about another 16-year-old, a kid named Joseph Shaposhnik in Northridge, Calif., who not only has a pretty impressive portfolio but also founded the Chatsworth High School investment club at the age of 15.

Now the fact that teenagers are getting into the stock market isn't the newest news in the world; I wrote a piece about it in these pages in 1998, profiling young investors from 23 years old down to nine. (The nine-year-old was also an avid Beanie Baby trader. "I bought Princess for $6," she told me. "It's worth, like, $70 now.") With Joseph, however, a few initial phone conversations convinced me he was no ordinary teen investor. What's more, most of the 40-odd students in his weekly investment club, despite having dozens of school clubs to choose from, keep sacrificing their Friday lunch breaks to hear Joseph talk about price/earnings ratios, balance sheets and, yes, fundamentals. From what I'd been told, a little local press coverage had sent attendance soaring, with up to 60 students crammed into a classroom, including athletes, cheerleaders and other members of the school's popular crowd.

Most of the teen investors I've talked to approach investing like a video game--Ameritrade custodial accounts as the Sega Dreamcasts of the moneyed high school set. For a lot of them, it's cool to flip tech stocks, churning and burning like young Bud Fox knockoffs. But Joseph and the students who flock to his investment club (at least most of them) sounded like a strange new hybrid of teenage investor: cool and conservative.

I was thinking about this as I was driving north on the Ronald Reagan freeway through the San Fernando Valley, birthplace of Fast Times at Ridgemont High. I was on my way to one of the weekly lunchtime meetings where, for 30 minutes, students ask about timely business issues and listen to Joseph talk about stocks and tenets of investing.

After meeting Joseph, I quickly realized he's the kind of kid I hated in high school: likable, honor-roll smart, athletic, charming, funny, and friends with both the cheerleaders and the computer guys who ogle them. His teachers gush. His parents beam with pride. The local radio, TV and newspapers love him. And girls dig him. He has the confidence of Tony Robbins and the financial passion of Jim Cramer. And as of Feb. 9, he has his driver's license. He is, quite clearly, a force to be reckoned with.

When Joseph was 12, he convinced his father, a Russian emigre, to buy into Microsoft. He then recommended Turner Broadcasting before it merged with Time Warner, which is now merging with America Online. Not a bad start. When Joseph turned 13, he put all $3,000 of his bar mitzvah money into the market. All of it. And to this day, more than three years later, he hasn't taken any out, and says his money has increased more than four times since, with very few transactions. "If you pick four or five great stocks and forget about them," he says, matter-of-factly, "you'll be in great shape."

It's that philosophy that he preaches to the students at the club meetings. When I tell him I met a girl in the hallway--not a club member--who says she's made thousands of dollars on penny stocks but can't remember their names, Joseph shakes his head. "You can't plan your future on penny stocks," he sighs disapprovingly.

And then it comes time for the weekly meeting. The school bell rings, and Joseph struggles with the overhead projector as the students wander in with their lunches. It strikes me how young they are when one girl sets down her big yellow Po-kemon keychain while she unwraps a sandwich. Joseph hooks up an MP3 player to a speaker for a little ambient music. As he begins to pull up stock charts on the overhead projector, Tupac Shakur and Dr. Dre sing "California Love": We in that sunshine state with a bomb ass hemp beat/the state where ya never find a dance floor empty/And pimps be on a mission for them greens/lean mean money-makin'-machines servin' fiends.

It's not exactly tea with the Beardstown Ladies.

One student shouts out in the darkness, over Tupac and Dre, "What happened to DoubleClick today?" Joseph turns to the student and says, "Aren't they getting probed by the SEC?" (Actually, it's the FTC.) Two Beavis and Butthead types off to the side titter: "He said probed."

But most of the students are serious about listening. Joseph decides to break down the stock Rambus Inc. for the students. He uses a laser pointer to illustrate what's happened to the stock over the past year, goes on to read from a company press release, and then discusses the potential implications to the stock price if the company wins a crucial lawsuit. When he mentions that a lot of people have been shorting the stock, the club sponsor, an accounting teacher named Gary Weissner, shouts from the back of the class, "Hey Joseph, why don't you explain to them what short-selling is?" Joseph replies, "That's what I'm about to do," and he does.

"Can you short a stock after hours?" asks one student. "If a company comes out with terrible earnings," the student continues, "like Legato, you could short it after hours and make a truckload off it." Joseph explains that by the time the student gets the news of the earnings, the market will have already reacted. Unfazed, the student responds, "But what if I'm looking at it in real time? When I'm not in school?"

The last order of business is the CNBC Student Stock Tournament, in which the club recently placed 22nd out of 3,508 student teams nationwide. CNBC has another round starting the following Tuesday and the Chatsworth High club needs to start thinking about its portfolio. "I think we definitely had the best risk-adjusted return of any of the teams in the competition [last time]," Joseph says. "Every team above us, all 21 teams, was invested in IPOS. Most of the stocks that we had had a market cap of $2 billion or more." This time, Joseph isn't content with a top 1% finish. So he's developed a new strategy: In addition to its big-stock portfolio, the club will enter another portfolio consisting solely of IPOs. Joseph knows the big-stock approach is the sensible one. But he also wants to win.

Success in the tournament has the faculty begging for stock tips. Joseph's Spanish teacher has asked for mutual fund recommendations; his counselor and math teacher have asked for suggestions as well. Even the class sponsor, Mr. Weissner, has sought their advice. In fact, Weissner has had so many colleagues asking for financial help that he's decided to form an investment club for the school's teachers, using real money. It's the latest twist on teensploitation. Says Weissner: "I'll start using the kids to do the research."

Curious about Joseph's stock-picking methods, I drive him home after school to check out his daily routine--whipping up a fruit shake, geting pumped up with the theme music to Rocky and then spending two hours on research for his own portfolio, his dad's and his stock club's. Once we arrive, we head into his room, where he fires up the digital music player on a computer that sits below two large posters of Michael Jordan. Then he begins surfing dozens of bookmarked sites like BigCharts.com and Yahoo! Quotes. On MoneyCentral.com, Joseph utilizes an elaborate screening filter to scan new stocks. He sets specifications for everything from projected earnings growth to how much the average employee of the company is paid relative to others in the sector. Citing examples of various companies, he enters ticker symbols without looking them up.

Naturally, he supplements his Internet research with some television, though his preferences have evolved over the years. Despite having flown to Las Vegas with his dad for a Louis Rukeyser conference, Joseph says he doesn't watch Wall Street Week much anymore. "He doesn't really impart all that much wisdom," Joseph says dismissively. "He basically just turns and says, 'So, Abby Cohen, which stocks should we buy?'" Joseph shrugs. "It's not really a very hip show." He prefers CNBC. "I want to hear something directly from the CEO's mouth," he explains. "That's useful information."

But in fact, Joseph has no aspirations to be a CEO himself someday, fielding questions from the Ron Insanas of the world. He has other plans. When a local anchorman has him on to talk stocks, he asks Joseph what he wants to be when he grows up. Sporting a fashionable blue shirt and tie, Joseph looks right at the camera and says without hesitation, "I want to be known as the best portfolio manager ever."

And he actually may have a shot--but first things first. Joseph is still 16. And aside from P/E ratios and annual reports, he clearly has another passion: girls. He hasn't been dating a lot lately, but recently a pretty blonde from class called him up at home, inquiring about the stock club. "Can you really make money in the stock market?" she wanted to know.

Can you really make money in the stock market? Could this be the newest high school pickup line of the 21st century? Seconds later they make Friday night plans at the cineplex. The movie? Boiler Room.

The hot date movie when I was 16? Risky Business.

Maybe things haven't changed that much after all.