For years, Charles Best knew he wanted to educate children.

Fresh out of college in 1999, he landed a teaching job at Wings Academy, a public high school in a poor section of the Bronx, one of the boroughs of New York City.

It was a rude awakening.

The stark realities of the job were surprising — namely a lack of funds.

Teachers cared about their students, but couldn't provide a first-rate education with bare-bones materials.

"We'd spend a lot of our own money on basic paper and pencils. But we'd be in the teachers' lunchroom talking about projects that would take our classes to the next level: books we wanted them to read, art supplies we needed, microscopes for a science experiment. For those resources, we just had to watch our students go without," he said. "These ideas that we had for innovative ways to teach . . . wouldn't go beyond the teachers' lunchroom because we didn't have an avenue for bringing them to life."

So just a few weeks into his new career, Best went to work on a solution: a new kind of charity that would eventually funnel millions to underfunded public schools.

He knew there were people willing to help who cared about education, but there was a vacuum of options to do so.

The primary method — writing a check to a school — worked in richer schools, but even then often left donors unable to see where the money really went. Plus, it left much of the job in the hands of parents who, in poorer schools, had little cash to spare.

Book It

The missing link, he figured, was a trusted way for anyone to contribute.

"If there was a way for people to choose an individual classroom project that spoke to them personally and see their impact, and hear back from the recipients . . . then we teachers would be able to get those books and go on that field trip," Best said.

So like other young entrepreneurs at the height of the tech boom, he turned to the Internet.

Like some of the Web's more revolutionary concepts, Best's idea was simple: He envisioned a Web site, DonorsChoose.org, that would let teachers post requests for funding for projects. Donors could browse requests, choose their favorite, fund the project and get a response from the students they were helping.

He envisioned an eBay-style online marketplace for philanthropy.

Like most new concepts, its potential wasn't immediately recognized.

He cajoled 10 teachers to submit the first proposals to the site. At the time, Best was living at home with his parents and earning around $30,000 a year.

He knew if those projects were funded, the organization would grow. He spent his own money — he estimates $3,500 — to secretly pay for all of the original proposals.

"That got it going," Best said.

Thanks to word of mouth, soon a solid base of teachers from local schools was submitting proposals.

The next, more difficult challenge would be finding donors.

"For the first couple of years, DonorsChoose was run out of my classroom and out of my parents' home." Best said. "Getting attention was all about cold-calling and hustling. You call 100 reporters trying to get them not to hang up on you. You send 200 letters to foundations that have never heard of you, and you're lucky if one of them responds. You're relentless and shameless and you hustle as best you can to bring people to the site."

It was a substantial challenge for Best, who grew up privileged as the son of a well-off Manhattan lawyer just a few miles — but a cultural world away — from the struggling schools helped by his innovation.

He attended St. Paul's School, an elite New Hampshire boarding school, and Yale University.

But his pedigree always included a healthy dose of responsibility and idealism.

"I knew since I was in high school that I wanted to be a teacher in a public school," he said. "I figured it would be important work and really challenging work. It was. And it is."

So he kept it up, teaching during the day and building DonorsChoose after school.

Without funds for a staff, Best enlisted his students to send thousands of hand-written letters to alumni from St. Paul's and Yale. His students generated the first $30,000 in donations to the site.

Though he lacked contacts with the media, his persistence finally yielded a column in Newsweek after one particularly lucky cold call to its editor.

National media attention followed, and Best became a spokesman for a new model of philanthropy. "It went from, 'Look at this little nonprofit experiment' . . . to trying to deliver on our potential," he said.

His little experiment grew to the point where Best, still in his 20s, realized he was out of his depth.

With no practical experience in business or finance, and only patchwork tech know-how — he is the first to admit he's no hard-core programmer — Best sought help.

Instead of looking to traditional charities for support, he held fast to the startup model, bringing in tech-leaning businesspeople to push DonorsChoose to the next level.

Peter Bloom, a successful venture capitalist at General Atlantic, heard about the program and funded several projects. After meeting Best, Bloom wound up as the organization's chairman. Why join? Bloom liked Best's response to his offer of a five-figure donation.

"Charles said, 'I want to give six inner-city kids the money and let them choose the proposal.' They self-organized," Bloom said.

That belief — that the best way to improve schooling comes from listening to the people in need — sold him on Best and DonorsChoose.

"The guy is the best listener I've met in my life," Bloom said. "He knows he has a lot to learn, but he's incredibly hungry."

The results have been impressive.

DonorsChoose has raised nearly $10 million for over 575,000 students (the tally rises in a counter on the site's home page) and pays for 30 full-time employees and a no-frills office in New York City.

The eBay Way

Best also helped wrangle a sizeable grant from the Omidyar Network, the pioneering investment arm of eBay founder Pierre Omidyar designed to fund citizen-driven solutions to social problems.

Yahoo, Time Warner, Lehman Bros. and Bank of America have offered up cash and accolades as well.

In total, nearly 36,000 individual proposals have been funded, and current requests on the site range from puppets for a Burgaw, N.C., kindergarten class ($155) to a digital camera-printer-scanner for Biloxi, Miss., sixth-graders ($1,037).

Best still says he'd like to return to teaching at some point (he wants to coach wrestling), but he plans to stick with DonorsChoose for at least a few more years.

Bloom considers a return to teaching a possibility for his protege, but places his bets elsewhere. "I think he's such an inspirational leader that that will be his calling," he said.

BY KIRK SHINKLE