PathBreakers

Orlando Bailey's Newsroom is Accountable to its Readers

You can’t shape your neighborhood if you don’t know what’s happening to it.  In this episode, co-hosts Tracey Pearson and Jamie Bennett talk to Orlando Bailey about how he runs a newsroom to build infrastructure for neighborhood power. They discuss: *Outlier Media’s innovative reader engagement and lead generating strategies like TXT OUTLIER and Detroit Documenters. *How Outlier has created an information ecosystem where residents can access the facts they need to navigate complex systems — from property tax appeals to housing assistance to understanding what decisions are being made at City Council.  *How information becomes infrastructure, and that journalism designed to serve (rather than extract from) communities becomes a tool for neighborhood self-determination. Orlando Bailey is an Emmy Award-winning journalist and lifelong Detroiter raised on the city’s east side. Before joining Outlier, he served as Engagement Director at BridgeDetroit and as Chief Development Officer for the Eastside Community Network.  Learn more: About Kresge: https://kresge.org/pathbreakers-podcast/ [https://kresge.org/pathbreakers-podcast/] About Outlier: https://outliermedia.org/ [https://outliermedia.org/] Detroit Documentors: https://outliermedia.org/detroit-documenters/ [https://outliermedia.org/detroit-documenters/] TXT Outlier: https://outliermedia.org/txt-outlier/ [https://outliermedia.org/txt-outlier/] The Speculators of Detroit: https://outliermedia.org/detroit-speculators-property-speculation/ [https://outliermedia.org/detroit-speculators-property-speculation/] This episode is part of the Detroit arc of PathBreakers Season 2, “Building Neighborhoods of Opportunity.” The arc explores how Detroit neighborhoods are forging their own pathways to opportunity — through information access, place-based economic revitalization and community organizing.  Stay tuned for conversations with: * Caitlin Murphy, Live6 Alliance — place-based commercial corridor revitalization in Northwest Detroit * Simone Sagovac, Southwest Detroit Community Benefits Coalition — securing community benefits from a $6 billion international bridge CREDITS: Hosts: Tracey Pearson and Jamie Bennett Producer: Juliet Hinely Managing Editor: Krista Jahnke Show Art: Alejandro Herrera PathBreakers is produced by the Kresge Foundation, founded in 1924 with a mission to promote human progress.

Detroit Mayor Mary Sheffield is Tending to Every Neighborhood

Season 2 of PathBreakers opens in Detroit — Kresge's hometown and a city whose comeback story has been told for a decade. But as hosts Tracey Pearson and Jamie Bennett note, that story has largely been written through the lens of downtown. The real test of Detroit's revival is whether neighborhoods share in it. In November 2025, Detroit voters made a decisive choice: by the widest margin in the city's history, they elected Mary Sheffield mayor. The daughter of a civil rights leader, the youngest city council member in Detroit history at 26, and now the first woman to serve as Detroit's mayor, Sheffield didn't run on a downtown comeback story. She ran on neighborhoods first. In this episode, Kresge President & CEO Rip Rapson sits down with Mayor Sheffield on the Marygrove Conservancy campus — where Sheffield anchored her transition — for a wide-ranging conversation about what governing for neighborhoods actually looks like. They discuss: * Her "stabilize, support, grow" framework for neighborhood investment * Centering children and families — from Rx Kids cash prescriptions to bus passes for every Detroit public school student * The new Office of Poverty Elimination and the appointment of Dr. Luke Shaefer of U-M Poverty Solutions * Detroit's property tax burden — among the highest in the country — and what reform could mean for residents and development * How the city is navigating the loss of $800M+ in federal funds * What she'd ask of Detroit's philanthropic and corporate community Next week: we leave City Hall and head into the neighborhoods. Meet Orlando Bailey, Executive Director of Outlier Media — the newsroom built on the premise that journalism should serve the people who need information most. Learn more about Mayor Sheffield [https://detroitmi.gov/government/mayors-office/mayor]: Preview all of Season 2 [https://pathbreakers.kresge.org] *CREDITS* Host: Rip Rapson, President & CEO, Kresge Foundation Producer: Juliet Hinely Managing Editor: Krista Jahnke Production support: Jennifer Kulczycki and Tracey Pearson Video interview produced by Mark Marx Director of Photography: Rodney Johnson Audio Technician: Keith Schembri Associate Producer: Bria Brown Video Editor: Carmel Flanagan Logo animation: Collin Leix Special thanks: Wendy Lewis Jackson and Jonathan Hui (Kresge Detroit program)

Trailer: PathBreakers Season 2 Premieres May 13th!

Four American cities. Sixteen people working to improve where they live. One central question: Who has power to shape what happens in their city? In Detroit, New Orleans, Memphis, and Fresno, we talk with community leaders building neighborhoods of opportunity, reclaiming narrative power, and creating the conditions for families to thrive. And we sit down with city leaders to ask what it looks like from City Hall. Hosted by Tracey Pearson and Jamie Bennett, with mayoral episodes hosted by Kresge President & CEO Rip Rapson. Our first city series on Detroit premieres May 13th 2026. New episodes drop on Wednesdays.  Preview our whole season at pathbreakers.kresge.org [http://pathbreakers.kresge.org]

Rip Rapson is Leading Kresge into a New Chapter

In this special season finale episode, hosts Tracey Pearson and Jamie Bennet welcome Kresge Foundation President & CEO Rip Rapson back to reflect back on the stories heard throughout the series and to share an exciting announcement about the future of Kresge. In this conversation, Rip also looks back on his journey to Detroit, reflecting on formative experiences and the influences his architect father and librarian mother had on his development as a leader, thinker, and citizen. And Rip does not escape the PathBreakers “lightning round” tradition … Tracey and Jamie ask Rip 10 “hard-hitting” questions with surprising answers.  Read more about Kresge’s big news [https://kresge.og/hq]  Read Rip’s book, Drawn to Challenge [https://www.riprapson.com/work/books]  See Rip Rapson’s Drawings: Visual Maps to Change [https://kresge.org/resource/rips-drawings/]

Dr. Darrick Hamilton is Utilizing Academic Research for Social Action

What is the purpose of an economy? What if economies were centered on people instead of money? What if everyone had access to both income AND wealth? These are the questions Dr. Darrick Hamilton works to problem-solve at the Institute on Race, Power, And Political Economy – an academic center he founded and directs at the New School in New York City, where he and his colleagues work to create “knowledge for action.” In this episode, Dr. Hamilton delivers some “Political Economics 101” delving into inclusive economic rights, human-centered economies, and trust-based governance. He also explains how his Baby Bonds program is leveling the economic playing field for over 33,000 babies in Connecticut and how investing in low-income and low-wealth people leads to positive economic benefits for everyone. Learn more about the Institute on Race, Power, And Political Economy [https://racepowerpolicy.org/] Learn more about Baby Bonds [https://racepowerpolicy.org/baby-bonds/]