On March 31, 2009, the Chicago Sun-Times declared bankruptcy, and some ideas I’d been floating about the future of news caught the attention of a few producers. As a result, I was invited to appear on WTTW’s Chicago Tonight and ABC 7 News to discuss my thinking. I believed the traditional news sector was deeply in peril, and that journalism as we knew it was transforming into a “constellation” of digital newsrooms. Financially energizing that start-up news sector, I believed, would be program-related investments from foundations—made easier to deploy by a new legal structure called the L3C newsroom.
I was half right. Read on to learn more about that.
As a result, for nearly two decades, my mission has been reducing noise, increasing credible sources of information, and adding value to our professional and community lives through digital newsrooms.
Here’s how I found that mission.
Chicago City Hall culture change is harder than it looks
I left business journalism in the ’90s to go into Chicago city government—my reasoning was mission-based: why write about good government when I could help create it? But it’s no surprise that the mission turned out to be more complex than I’d anticipated.
After serving in the offices of Mayor Richard M. Daley and CPS CEO Paul Vallas, I left public service with a hard-won understanding of the difficulties of culture change — and a front-row view of how the rapid shrinkage of newspaper newsrooms was already undermining the public’s access to vital information.
Along the way, through several projects I had worked on – including establishing the Children First Fund: the Chicago Public Schools Foundation – I had also developed a top-level perspective on philanthropy, the way foundations operate and how they carry out their commitments to their missions and social change. And I was deeply passionate about developing new tools on the Web.
Journalism and NPO status seemed a bad fit
That path led me into mission-based community engagement and fundraising. That work left me genuinely uncertain whether journalists were cut out for the non-profit world and its relentless cycles of fundraising. I also thought it was important that newsrooms be able to take a stand on candidates in elections. NPO newsrooms cannot.
That question was weighing heavily when the Sun-Times laid me off in 2008. For years I had worked with web entrepreneurs and mission-based businesses and nonprofits to build the social web. My journalism background seemed a good fit for the crusade to save it.
When I learned about the L3C — an investment vehicle that promised to be designed to encourage foundations to make program-related investments in mission-based businesses — I connected the dots between news and mission and found a cause I could fully get behind. I plugged into a colleague running the now defunct HuffPost Chicago, who gave me a column.
I began writing about what I called the L3C Newsroom and regularly delivering information on this, PRIs and other emerging ideas to foundation executives and others working in the digital newsroom space. I built a robust social media presence on the topic of emerging business models for news and was among the first journalists on LinkedIn to actively work that professional network on the business of civic and local digital news.
In 2010, I recorded this video on the idea of an L3C Newsroom — similar to a crowdfunded newsroom, with a community foundation leading the way for smaller family foundations to provide core investment for local independent newsrooms. The video was for a very early and unsuccessful kickstarter.
A video I recorded in 2010 on the idea of an L3C Newsroom, similar to the idea of a crowdfunded newsroom with a community foundation leading the way for smaller family foundations to provide core investments for local independent newsrooms.
Self-sustenance through newsroom fundraising and experimentation
During this time, I also consulted with clients such as the Better Government Association, as an organizational development and fundraising consultant, raising hundreds of thousands of dollars for its new team and operations. Understanding the vast news and information deserts in Chicago — from my time working in newsrooms and in Chicago city government — I took on multimedia consulting and project management with LISC Chicago, bringing neighborhood voices into the mix through a series of mobile neighborhood tours. As a community service, I produced a companion Twitter feed and Facebook page. Other clients from those years include the Chicago Tribune’s social media boutique 435 Digital (Facebook artifact here) the Block by Block Community News Network (TimeMachine here)and Knight Digital Media Center.
I carved out a small but passionate niche as an advocate for sustainable local media. The L3C idea fell more rapidly into the past as I followed Chicago’s diminishing news streams more closely and observed innovative ideas here and nationwide. Over the years, that concept had long ceased to be my catalyst, but I still believe that journalism and news need to be self-supporting businesses.
News needed patient capital from foundations; not a new legal structure
So, yes, it turns out I was wrong about the L3C. The L3C label obscured my basic premise: the need for long-term investments such as PRIs by foundations. The L3C label provides no shortcut or safe harbor. It has taken time, emotional healing and distance, and new research tools to clarify my view and remove those clouds. Mea culpa.
In 2016, I conducted a research project on Chicagos Independent News ecosystem. Sadly, that project was cut short when I experienced a family emergency. I became my father’s caregiver when he began failing in 2016; he died in 2017. Shortly afterward, in 2018, my life partner unexpectedly died on the day I moved into the house I and my brother and sister had inherited from my father. It has taken me eight years to be capable of writing that previous sentence.
I was very grateful for the paid work outside this sphere that came my way shortly after these sad events. It was difficult to think about the sustainable news work I had done previously. I had witnessed the suffering of many good-hearted people trying to keep their local news streams alive. Their suffering moved me to tears. The break down of civic fibers leading to Democracy was becoming more and more evident.
My heart was broken into shattered shards of work and love, and life purpose.
That said, I am grateful for the many opportunities that have come my way since 2018 to participate in the journalism world here in Chicago. When I enter these rooms, I feel like I am home. There appears to be an openness that did not exist in the past.
Meanwhile, an entire new ecosystem of integrated editorial platforms like Substack has emerged, as has the concept of Catalytic Capital. A mind-boggling array of associations, projects, audience development tools, funding mechanisms have emerged in what was at one time a sleepy fringe ecosystem.
Catalytic Capital: Long term patient capital for news
The emergence of Catalytic Capital for news makes clear that my advocacy for long-term patient capital from foundations was correct. AI-tool Claude tells me that catalytic capital is the broad umbrella concept for any capital that’s more patient, risk-tolerant, or subordinate than the market rate. This patient capital unlocks other investments, much like the tranches in what I called the L3C newsroom. PRIs are a specific legal tool that foundations use to deploy catalytic capital while satisfying IRS payout rules.
Separately, Tracy Baim, among others, have taken the lead on the newsroom sustainability front here in Chicago.
Through Press Forward, a coalition of 130 funders is investing more than $500 million over five years to revitalize local news; as of 2026 the initiative has disbursed more than $400 million through 46 local chapters nationwide. The two largest funders are the MacArthur Foundation — $175 million committed, including $48 million in initial grants and a further $20 million in December 2024 — and the Knight Foundation — a $150 million anchor investment. Other founding partners include the Carnegie Corporation at $5 million, the Hewlett Foundation at $10 million, Ford Foundation, Democracy Fund, Heising-Simons Foundation, Henry Luce Foundation, Joyce Foundation, McKnight Foundation, Lumina Foundation, Alfred P. Sloan Foundation, Robert Wood Johnson Foundation, the Lenfest Institute, and the Archewell Foundation, among others.
Press Forward Chicago (cct.org), the local chapter housed at the Chicago Community Trust and led by Tracy Baim, has a $20 million five-year goal and has disbursed more than $4.3 million to 37 local news organizations as of 2026.
Separately, a group of Chicago-focused funders — The McCormick Foundation, Driehaus Foundation, Chicago Community Trust, Field Foundation, Polk Brothers Foundation and the Democracy Fund, have created the Chicago Independent Media Alliance (CIMA). I have been happy to attend a few of their meetings.
Chicago Community Showcase for LISC Chicago.
This playlist is a series of audio slide shows I produced with community leaders to be delivered through an early Smartphone app. It is the core content of the Chicago Community Showcase YouTube channel. I ran a Facebook community and Twitter feed for several years as a public service but they are now dormant.

Some audience engagement tools to check out. Could any of them be useful to you?
Thank you for hosting a conversation May 10 as part of the Independent Media Circle for the Chicago Community Trust’s On The Table 2016.
What are the criteria to be considered independent media for On the Table 2016? 





