Succeeding When You’re Small: Lessons Learned from

Learning from the experience of those who started a nonprofit out of their basement and grew to be nationally recognized leaders.

Succeeding When You’re Small: Lessons Learned from
7 mins read

How one nonprofit successfully found a way to connect with people who wanted to help.

Although the Blue Avocado audience consists of community-based organizations, we can still learn from the experience of those who started a nonprofit out of their basement and grew to be nationally recognized leaders in the field. is one such organization. Started by Charles Best in 2000, it’s a crowdfunding platform for public school teachers. The nonprofit was started in his own Bronx classroom when Charles needed resources for his students, and he found a way to connect people who want to help.

Today they’ve become hugely successful: 78% of all public schools in the country have at least one teacher who has created a project on the platform. This school year they raised more than $140 million dollars and now have 100 staff, and enlisting the help of Oprah and Stephen Colbert helped make all that possible.

What can startup nonprofits and grassroots efforts learn from this success story? I spoke with Charles, who shared three insightful, possibly counterintuitive tips for scoring celebrity support in the early years, landing media hits, and strategic planning—let’s get into it:

Tip #1: Catch a Colbert

Stephen Colbert, the host of “The Late Show with Stephen Colbert” is on the board of How did they land him, and what can you learn from their experience?

Stephen Colbert was running for President in the South Carolina Democratic Primary in late 2007. Here’s how Charles tells the story:

We first engaged Stephen because we sensed he faced a problem: how to give his followers, the Colbert Nation, a way to support Colbert’s run for president financially, when (we thought) surely he did not want his fans parting with their hard-earned money on something that was satire. So we came up with the idea for a philanthropic presidential straw poll where people could donate to a classroom project in honor of their favorite candidate, which pushed that candidate higher up in what we called ‘a straw poll that makes a difference.’ Basically, we created a philanthropic contest to see whose candidate’s supporters could do the most for the kids and public schools.

We got it to Colbert through a board member who had a connection to the show and by way of Craig Newmark (founder of craigslist), who generously spent half his interview on the Colbert Report talking about and the poll. Colbert seized on it and promoted it, to the point that he won the contest and raised tons of money for South Carolina classroom projects. That started what has become an ongoing and incredible relationship.”

Key Takeaway:

Don’t approach celebs saying, “Hey, we’re a great cause and that’s why you ought to support us!” Instead, identify a challenge they face and find a way your organization can help solve it. In the process, of course the celebrity will find out how great your cause is.

Tip #2: PR Punch

Getting the word out about your cause is key to success and public relations can provide a huge boost to any organization. Charles shared his straightforward approach and the incredible results that followed:

“We cold called a lot of media outlets. We worked the phones like shameless hustlers, smiling and dialing a lot of reporters. We got hung up on 99% of the time, but one in a hundred calls resulted in a story. We were lucky: one of Oprah’s producers read one of those stories and they aired a piece on us. At the time, I was still teaching full-time and my students were our staff.

Early on, I used the fact that we were operating out of my classroom and my students were staff members to generate interest, and I think we had credibility just by virtue of being born out of a classroom. Today, we just try really hard to read the reporter’s previous articles and then in the first sentence or two say, ‘I’m reaching out to you because I’ve read your writing and here is a particular article you wrote that leads us to believe you’d be interested in this story.’”

Key Takeaways:

Media coverage is valuable; even if you don’t end up on Oprah, you never know who may read a story. To help your chances, identify the story that will be of interest to the public, versus just promoting your cause. Also, do your research on reporters and only approach those who cover related stories, and when you do reach out, link your story to their past work and interests, or to their current beat.

Tip #3: Forget Strategic Planning!

Conventional nonprofit wisdom says the road to success includes a mandatory stop mapping out your next few years. Is that the only option? Charles clearly believes the answer is “no” and takes a page from the Lean Startup philosophy that now permeates the business world, which is all about small, fast changes and learning as you go:

“Most of what we’ve done is learn from mistakes and iterate and improve as much as we can, rather than rely on major inflection points or strategic decisions. In fact, even now we don’t have a two- or three-year strategic plan. We just look out a year ahead at most. We try and set ambitious goals and figure out how to hit those each year, but we don’t do long term planning. I think the key is having as few existential, major decisions as possible and many more small improvements, so that it feels like a gradual evolution.”

Key Takeaway:

Instead of struggling to divine the future, focus on your goals for the year and plan what you need to do to hit those goals. Take a page out of Eric Ries’ book Lean Startup and learn from everything you do, iterating quickly so your organization is more adept at responding to inevitable changes, instead of committing yourself to a strategy that may quickly become outdated.

Well, there you have it. Charles’ tips may fly in the face of some of the things you’ve heard and thought, but it’s tough to argue with results. And while may be a huge organization by the standard of most of our readers, they started out small just like many of us, and the lessons they learned on the way to becoming a national force for good apply to organizations both large and small.

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