Dear Imaginary Jeff Skoll

An imagined conversation between me and one of my heroes.

Thanks, Imaginary Jeff Skoll, for sitting down and meeting me for coffee.

Imaginary Jeff Skoll: It’s my pleasure, Dance. I understand you have some questions about social entrepreneurship.

Jeff Skoll, philanthropist and entrepreneur

I do. 

IJS: How can I help you?

As you may know, I got my masters degree in social entrepreneurship and social change from Pepperdine University in 2012.

IJS: Why did you decide to get a masters degree in social entrepreneurship?

I chose that degree because I wanted to learn how to make a difference in a systemic, organized and effective way. I hated charity in the traditional sense: my grandma gives a few dollars to some fundraisers for holding up a photo of a sad baby, and then she doesn’t think about those dollars ever again. So grandma wouldn’t even know if the money she donated is actually doing any good, and I thought that was unfair to the donor and to the people at the other end of the donation who might be missing out on the services that those dollars could have purchased, if they weren’t being squandered by mismanagement.

IJS: So why social entrepreneurship?

I didn’t know on the day I started grad school if I would learn the solution to that problem. Traditional notions of giving still remain and social problems persist in spite of governmental and community efforts. But I learned that social entrepreneurs take the responsibility of managing those donations and good will by having a solution that addresses the root problem, innovates a scalable solution to that problem and resourcefully makes a measurable impact.

IJS: It sounds like you’ve got it figured out.

But I wasn’t able to become a social entrepreneur. I’m not a master. I couldn’t commit or agree on an idea for my own community service program. I was worried that I’d be homeless and poor if I tried to work for myself. So I left Los Angeles and moved to Guam to figure out how I could apply the degree I loved to my work. I became a reporter for the local newspaper on the island. But I wanted to ask you: was I wrong? Could I have made it as a social entrepreneur?

IJS: Let me ask you this—what do you really care about? What issues make you want to yell at your television set?

Human rights injustices. Poverty. Violence. Media partisanship. Lots of things.

IJS: OK, I’ll ask this in a different way—what makes you really excited?

Telling stories.

IJS: That’s something you and I have in common. I also love telling stories.

Mm Hmm…

IJS: What?

Don’t take this the wrong way or anything.

IJS: Lay it on me.

Imaginary Mr. Skoll… You have a great business sense, that’s clear. But. Your taste is questionable… There. I said it. 

IJS: That’s your opinion.

Technically, it’s the opinion of quite a number of people who have watched Participant Media films over the years. I mean, An Inconvenient Truth, The Cove and Goodnight and Good Luck were excellent choices. But The Help? Lincoln? The Fifth Estate? Anyway, I didn’t bring you here to disparage your taste, or the taste of the executives green lighting your movies, I want your advice as an entrepreneur.

IJS: You bring up an excellent point.

I do?

IJS: Do you think it stops me from making a movie I care about when someone criticizes another project of mine?

… No.

IJS: Does it stop you when someone criticizes you?

In my defense, I didn’t create Ebay, so I don’t have a buttload of Ebay stock to fall back on.

IJS: I might have more resources than the average Joe, but I have just as much pride. If you prick me, do I not bleed?


IJS: Look, we both love telling stories. We both want the world to be better. It’s safe to assume you and I both subscribe to the idea of meliorism. The idea that the world can be made better through human effort.

It’s in my bio, Imaginary Jeff Skoll.

IJS: OK, so what kind of effort are you putting into the world to make it better? How is that effort scalable? How is it sustainable? How is it replicable? How is what you’re doing revolutionizing a system that isn’t working so life will be better for human kind?

Well, I’m a reporter. I ensure the public is educated and informed about their government and the agencies that protect their health and well-being. I tell the stories of the underrepresented in the community, and the stories that impact our community whether the people living here like the news or not.

IJS: How is that scalable?

Well, the news industry is changing. I’m not sure how to scale my reporting in an industry that’s undergoing upheaval.

IJS: Remember your education, Dance. What did you study in grad school?

Well, social entrepreneurs, they… The revered craft of journalism is a public service, and it’s supported by ad dollars, which means… Sustainable streams of revenue have to come from… I don’t know anymore.

IJS: OK, I’ll spell it out for you.


IJS: What are you trying to do? With your career? As a reporter?

Ensuring the public remains informed and connected through the practice of storytelling.

IJS: What needs to change?

The way individual news companies are responding to a world that doesn’t consume news and information through print and television anymore.

IJS: So what do you do?

Meet the needs and desires of the readers. 

IJS: And then?

And then you put out a plate of freshly baked cookies next to every newsstand.


OK, not seriously. On Guam we put some good chesa out and call our primos for BBQ.

IJS: I don’t know what that means.

That’s because you haven’t been to Guam yet. Come on, Imaginary Jeff Skoll. Guamanians could really benefit from your perspective on innovation and sustainability. 

IJS: Are you buying my plane ticket?

With all of my imaginary money? Of course Imaginary Jeff Skoll!

IJS: *Sigh* I guess.

This has been brought to you by two glasses of red wine and lots of chocolate ice cream (I’m lactose intolerant).

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