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Kimberly is one of the founders of Free Press, which is currently celebrating its 20th anniversary. I caught up with my colleague to reflect on her crucial role in launching the organization — and on the two decades she’s spent shaping it.

Getting Free Press off the ground

How did you first get involved with Free Press?

I was working in a consulting capacity with the Media Education Foundation in Northampton, helping them do some business planning and some facilities planning. And [MEF founder] Sut Jhally is a communications professor at UMass and a contemporary of Bob McChesney. Sut asked me to sit in on a couple of meetings where the idea of Free Press was being discussed.

Bob McChesney, John Nichols and Josh Silver were the initial folks who were batting around the idea of a new national media-reform organization. Josh was beginning to read Bob and John’s books and began to internalize the theme that the media system is so integral to everything about a thriving democracy. And, indeed, our nation was founded on the notion of a free press and a diverse press.

So my role was in kicking the tires of their business proposal and their idea of starting a new organization. I also worked with Sut as his adviser to help him determine whether it was a good idea to have Free Press be a sponsored project of the Media Education Foundation. So that’s kind of the origin story.

I hadn’t really worked in the media and tech or democracy space before, but we were in the run-up to the invasion of Iraq and Afghanistan, and my one and only sibling was in the Air Force and being deployed. I was becoming aware and concerned about the falsehoods that then-President George W. Bush was spreading through our airwaves around the weapons [of mass destruction]. And I had a sense that, wow, here’s something tangible I can do to combat something that’s impacting my brother and my family.

I imagine that having that kind of deep personal investment must have made it feel all the more crucial to get involved.

Yes, and I was able to apply my suite of skills around business planning and financial planning. But each time I read a round of ideas and proposals, I kept coming back to how this was impacting our entire nation. And many, many families and individuals who care about peace and world security and who care about truth and the institution of the presidency. How important that is to all of us.

What did you need to do to turn the concept of Free Press into a reality?

There was a lot of what we call field-landscape analysis, like who’s doing what, all of the layers of activism, institutional work, funding possibilities. So it was analysis of: If this idea of Free Press as an organization can get some traction, what would we work on? Who else is doing that? How would we relate to them? Who could fund us? What is the possibility for fundraising? What should the structure be? Where should the structure be? Do we need a physical location? Can we be remote? Would it be wise to stay inside the Media Education Foundation’s container?

We did become a sponsored project for about nine months before we incorporated and launched. It was really a lot of business planning and financial-analysis work at the same time. As you can imagine, those three founders, Josh, Bob and John, were overloaded with ideas. And the first National Conference for Media Reform was already in their brains and taking shape. Before we even incorporated, we had a date, we had a location, we were gonna offer a national conference, none of us had ever done that before.

There was a lot of learning on the go and harnessing that startup energy and making sense out of it. It was taking concepts and putting them into plans and also beginning the case for support, doing the things that would attract other employees.

At that point, it was just Josh and me as staff. And then we slowly started adding people. Ben Byrne became our web person. Russ Newman became a research person. We hired Yolanda Hippensteele for the conference. All of us were consultants because we didn’t have an employer until we incorporated on Aug. 14, 2003.

Did you and the other founders always know that you wanted Free Press to have a nonpartisan focus?

Yes, that was very much part of the DNA. We knew the problems with the media were not a left or right issue. This is not a party issue. This is about the health of a civic society — a flourishing and diverse media system that serves everyday people is essential to the functioning of democracy. So yeah, it was never a political or partisan concept.

What were some of the earliest challenges that you had to face once Free Press incorporated and became an independent organization?

Well, our brand was an issue: While our name was Free Press, our URL was And we worked on so many issues. I think our first website covered 95 issues. And we had a tome about each of them, looking at what was wrong, what the diagnosis was, what people could do.

The real challenge was harnessing all of this, and understanding how many things were broken in our media system, and figuring out what the priority was to fix them. And we were working inside the constellation of staying national, with a domestic focus.

We were going from an unincorporated group of well-intended people to building a structure that employs people and has personnel policies. We had an office for the first time. It was an apartment above the Iron Horse on Center Street in Northampton. Someone’s office was in a bedroom, someone’s office was in the living room. We had a kitchen, which was nice. We could make lunch. But it was a little ragtag.

I was focused on bringing order to the chaos of ideas and on figuring out our resources and hiring people. We had some good early success with fundraising, which is part of why we hatched out of the Media Education Foundation. It was clear pretty early on that our annual fundraising would probably eclipse MEF’s budgets. We knew that would pull them off their game, and they needed to stay focused on what they do and what they do well. That’s why we hatched, just to be very disciplined about our purpose.

It took a good couple of years to get in a rhythm. And I would say the first eight years were just rapid growth: We went from zero people to 20. That’s a lot of change.

Rejecting corporate money

Free Press doesn’t take money from business, government or political parties. How did you develop a funding policy and decide which funders and philanthropists you were initially going to reach out to?

We didn’t clarify our mature fundraising policy until year five or six. But from the start we didn’t take money from corporations. We were very pure about that. We knew we wanted to get funded by public charities, private foundations and individuals. We did not want to chase corporate dollars, even for the conference, which is a typical way to fund a conference.

But our formal articulation of our fundraising values didn’t emerge till a little later. The conference was like our fundraising strategy. We had a big tent where we brought in all the players who had been working longer and differently than our little fledgling startup. And the conference itself, that first event in Madison, Wisconsin, really was our first year and a half of fundraising. And through that conference, we got on the map. We thought maybe 300 or 400 people would show up and 1,500 people came. It was amazing.

We then had to think about how to get funding for general support and program work and campaign work. We needed funding for our research agenda and an organizing campaign. This was the era where Commissioner Copps and Commissioner Adelstein were the minority members of the [Republican-led] FCC. We took the [two of them] to cities across the nation and talked about the problems of the media and the consolidation of media ownership. We were organizing communities across the nation, and turning people out to testify publicly about how their media was helping or harming them.

That was a very vibrant era, too. And it got us the attention of some institutional funders that only recognized us when we were on their turf.

You mentioned that we never took corporate money. Did we at any point take money from government or political parties?

No. We understood that money is power. And we wanted to be unfettered.

That kind of pure focus really distinguishes us from so many organizations.

Yes, which is not to say that people cannot do good work and ethical work and independent work when there’s government or business money in the mix. But you have to look at the predominance of it.

From a tiny apartment to a force in the field

You mentioned the Center Street apartment in Northampton, Massachusetts. Did we also always have a D.C. presence?

We did not have D.C. staff for at least two years, so there were lots of trips to D.C. I think our first physical presence [there] was a sublet of a space inside an allied organization.

How did you determine how to grow the staff in those early years?

Part of it was based on the work plan. Research and organizing and popular education and communications were all clearly important needs. … I have a sensibility around building things that you need to invest in equally — like if you’re going to build something stable, you need to have the externally facing stuff. But you also need to build the backbone of the organization with finance and fundraising.

It was like a circle: If we added to our program staff, then I needed to hire an office manager. It was just like a spiral growing out.

Aside from the early years, what is the biggest challenge that you’ve ever faced as our orgitect?

One of the hardest challenges I faced, which was a beauty and a beast, was the impact of the conference on our DNA. We were known and supported for creating that big space and that big event. But it took 18 months to pull off each of those events, and a good portion of the organization was consumed by conference planning. Then the conference would be over and we’d all take a breath. And then we’d have to think, well, what are we working on now?

There was a little core sort of discord between steady building of a campaign plan to inspire the hearts and minds of people to care about democracy and media transformation while this big event was happening every cycle. The hardest challenge for me was to do the analysis of, is this the right thing to invest this much time and money in? And [after six conferences] I concluded the answer was no, I don't think we should do this anymore. We need to find a different way because it’s all consuming and it’s creating a cycle that is limiting.

The other big challenge is just riding the waves of human and financial support, which ebb and flow and go in cycles. We’ve had really strong success in the diversity and size and continuity of our funders. But those dip and go up and down and not necessarily predictably. So being able to surf the wave and give good advice when we’re in a rainmaking year. We always want to be careful because the next year could be a drought. Everything is about making educated guesses.

Weve shifted from having a staff based primarily in two physical offices to a staff that is now majority remote. Could you talk about that evolution?

We were among the early adopters of the concept of remote. The Massachusetts physical presence was near and dear to my heart. It’s my home turf. My husband designed our office. It was a beautiful space and an affordable place. For many years, as you know, our D.C. crew came up to our environment for our staff retreats. There was a mission value in showing, we are not of the D.C. Beltway; we are outside of it, as most people in the world are.

But as we started to really develop our street cred, if you will, and the respectability of our policy positions and acumen and leadership, we knew we needed a D.C. presence. In Free Press’ history, we have had three physical offices in each location before we settled into our homes. But I know that the pandemic really prompted many national organizations to consider remote. We were well ahead of that.

Tim [Karr] was our first remote person and our only remote person for so long. But the News Voices [journalism] program really demonstrated that if we’re going to work in communities, we have to be there. We realized the need to hire staff who weren’t attached to D.C. or Massachusetts.

We also realized the need to accommodate people whose lives were changing — if they needed to move, for example, or just didn’t like New England anymore. It made sense for us to accommodate that because these folks are important. They’re part of our family, and they’re doing good work. The News Voices experiment showed us what was possible, and then the desire to retain talent was the second reason.

And then it was, oh, we need new skill sets. We’re not actually attracting folks to come to Northampton to work for us. We need to get them where they are, and let them be where they are. So it was an evolution. But when I talk to counterparts at other national orgs, they’re still really grappling with should we have remote staff? Of course you should.

Look, it’s not easy to do. I will not sugarcoat it. It is really hard to keep up with employment laws in different states and rules and regulations and all kinds of stuff. I think we have 17 jurisdictions or something now. It’s very complicated. It’s not an easy thing to do but it’s the right thing to do.

How has the shift to primarily remote work connected to the mission of attracting a more diverse staff?

I wrote a case study about our journey to becoming majority people of color and how intentional we were about that. Our remote work was more about strategic geographic decisions of where we were organizing, who we were organizing with and for what. And then also attracting the top of the top. That — coupled with our intentional hiring, vision and goal setting, and practice changes — has transformed the organization.

Earlier you reflected on challenges in Free Press’ first 20 years. What aspects of your work have felt the most rewarding?

Developing leadership, and really mentoring folks who either want to be here [for the long term] as well as those who want to give us their all for a couple of years and hatch out. Look at all of the people who have grown on the job and matured on the job. It’s because we support leadership, and try to get people in their right lanes, but not limit them.

I’m female. And I will say that Free Press has always had many feminine qualities. I think that giving support to rising female-identifying leaders is a good thing to do in the world. I’ve been very intentional about that.

Free Press has such an incredible reputation both in the field and beyond. And so much of that has to do with your leadership. Now that we’re embarking on our third decade, what visions are you holding for the future?

I’ve been doing a lot of thinking about how in an ecosystem of any kind we need strong networks. The nonprofit public-interest sector in general — and the media-justice and media-reform communities in particular — need more investment and more intentionality on strengthening security.

You’re increasingly successful, and increasingly drawing the ire of your opponents. We are working in an environment where society has changed to be quite polarized, quite triggered and dangerous. Security, whether that be cybersecurity, physical security, we have a lack of capacity to handle the environment in which we’re working. And we’ve got to build that capacity as fast as we can. I think a lot about that. Not from a fear place, but from the perspective of org development and capacity building.

The other piece is a lot of leaders are aging, myself included, not just inside nonprofits but on the funding side as well. So just understanding that and mapping that out, thinking: What is the vision for financial support of our organization going to look like in five years? What will it look like in 10 years? How do we intentionally prevent a gap or a cliff or whatever?

Whether you’re the sole proprietor of a small business or a big org or a department inside an institution, running anything is about looking around the corners, and seeing what’s in the future, and trying to spend as much time on that as on doing what’s on your plate in the present.

One of your strengths as a leader is how proactive you are. And I can see that reflected in everything you just said.

It’s something I have to push myself to do. Because the load is always intense.

It has been such a joy to speak with you. Is there anything else you’d like to share about your work?

I mean, I’m amazed at how motivated I remain after 20 years. I like solving problems. Problem solving can be daunting, but we’ve got a good team of people in the organization to apply their viewpoints and suggest bold visions. And just reading about our work and hearing the stories from the field that you produce, it does fill up a well when the well gets dry. It’s motivating.

Help Free Press keep fighting for the next 20 years: Donate today.

Check out the other posts in our 20th-anniversary blog series.

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