DonorsChoose Founder Charles Best On The Art Of Asking For Money

Asking for money doesn’t have to be painful. Donors Choose founder Charles Best boils it down to three principles.

DonorsChoose Founder Charles Best On The Art Of Asking For Money
[Image: Flickr user Marshall Astor]

Whether it’s a big donation to a nonprofit or a business-boosting investment, asking for money can be tough. It’s all sweaty palms and dry throats as we build ourselves up to seem worthy enough for the money source to fork over some dough.


But Charles Best doesn’t see it that way. Best is a former Bronx high school history teacher and founder of, a New York City-based nonprofit that helps school teachers find funding for their classroom projects. The organization has helped more than 178,000 teachers raise more than $227 million for projects ranging from trips and musical instruments to science projects and technology upgrades. Oh, and he’s successfully asked folks like renowned investor Fred Wilson, MSNBC anchor Jonathan Alter, and late night talk show host Stephen Colbert to sit on his board of directors.

The way Best sees it, there are three key principles to asking for money in a way that makes the process easier–and even fun. Together, this triad makes the ask feel more like the thrill of the chase than going hat-in-hand and ingratiating yourself to someone, he says.

Offer a platform rather than a prescription.

Too often, people looking for money feel like they need to present themselves as if they have all the answers, Best says. They sit down, all full of bravado and say they have discovered the best solution, product or service, trying to impress the investor. That’s risky, especially if the money source doesn’t see it that way.

A platform approach, on the other hand, first requires some homework to find out what’s important to the person handing over the cash. What’s important to him or her? What are that person’s objectives? Then, present yourself as a solution to address those priorities and reach those goals.

This was the approach Best and his team took when trying to attract Stephen Colbert to the organization. Best and his team came up with an idea for a “philanthropic straw poll” on where donors could “vote” for their favorite Presidential candidate by making donations to schools. At the time, Colbert was making a satirical run for the top spot on the Democrat ticket and wanted fans of his show to have a way to show their support.

“He had all these members of Colbert Nation wanting to open up their wallets and purses to support him as he agitated to run in the Democrat primary,” Best recalls.


Yet Colbert didn’t want people to send money to a campaign that wasn’t a serious run for office. The straw poll solved his concern about people sending money directly to him. Instead, they could show their support by funding classroom projects. Colbert has been involved with since the idea was pitched to him by board member Craig Newmark, founder of online

Ask personal questions.

In order to find out more about what really gets prospective donors and investors excited, you have to ask them–and then listen to the answers, Best says. He recalls a meeting with HP’s chief marketing officer which had been set up by the company’s PR agency. Fifteen minutes into the meeting, Best saw the exec was “bored out of his mind and did not want to be there.” So, Best stopped his briefing and started asking questions about what the visitor had done that morning. He found out his prospective investor was an avid swimmer. With a few clicks, Best pulled up projects related to swimming. The top two projects were from special education teachers who wanted their physically handicapped students to be able to participate in the schools’ swimming classes.

“This CMO from HP went from being bored out of his mind to deciding that HP would give a million dollars to projects on in two seconds,” he says.

Exude infectious enthusiasm.

Go ahead: get excited, Best advises. If you’re not psyched about helping people use your organization as a platform, why will they be? This doesn’t mean you have to be a gregarious extrovert, Best, a self-described introvert, says. But he cares deeply about and it shows in everything he does from hiring employees to building relationships with contacts. Changed jobs or noted an anniversary on LinkedIn? Expect a note from Best if you’re connected to him. People are also in a more giving mood after they’ve received an award or promotion, he says. That’s a good time to plan your ask.

“You should probably put a bigger priority on making your excitement about your offerings tangible and that being a priority more than coming across as buttoned up and business-like,” he says.

About the author

Gwen Moran writes about business, money and assorted other topics for leading publications and web sites. She was named a Small Business Influencer Awards Top 100 Champion in 2015, 2014, and 2012 and is the co-author of The Complete Idiot's Guide to Business Plans (Alpha, 2010), and several other books.