PathBreakers

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/

About Outlier: https://outliermedia.org/

Detroit Documentors: https://outliermedia.org/detroit-documenters/

TXT Outlier: https://outliermedia.org/txt-outlier/

The Speculators of Detroit: 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.

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:

Preview all of Season 2

*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)

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

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 

Read Rip’s book, Drawn to Challenge 

See Rip Rapson’s Drawings: Visual Maps to Change

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

Learn more about Baby Bonds

Dr. Beverly Wright has been working in climate and environmental justice since before the movement had a name. After 30+ years of leading groundbreaking community-based participatory research in her hometown of New Orleans, Dr. Wright is a celebrated pioneer of the field. Since 1992 she has been the visionary executive director of the Deep South Center for Environmental Justice, the organization which she also founded. 

In this episode, Dr. Wright reflects on a post-Katrina New Orleans and her journey from sociologist to movement leader. She also discusses the “communiversity” learning model that she developed for the Deep South Center and the ways they are cultivating the next generation of climate leaders. 

Learn more about The Deep South Center for Environmental Justice

After a challenging experience of her own as a low-income, first-gen college student, Dr. Bridget Burns understood that higher education was not “user-friendly” for everyone. And from that, her career mission became clear: transform colleges and universities into places where low-income, first-generation and students of color could not just navigate, but thrive.

Dr. Bridget Burns is the CEO of the University Innovation Alliance, a multi-campus laboratory for student success innovation. In this episode, Dr. Burns shares her approach to fostering trust and openness in a competitive community and discusses how empathy is the first step in design. She discusses the UIA Listening Lab model for collecting student feedback and

also reflects how the principles of improv theater inform her approach to problem-solving. 

Read more about the University Innovation Alliance

Find free resources from the UIA

Watch the documentary Unlikely featuring Dr. Burns

Cardell Orrin spent years as a high-level IT strategist and engineer. Now, as the executive director of Stand for Children Tennessee, he is “debugging” the processes by which parents and community members in Tennessee engage with their local school boards and state representatives. It’s a debugging that’s needed across America’s school systems. 

In this conversation, Cardell reflects on a childhood of being “dragged around to school board meetings” by his mother, and the “cynical optimist” problem-solving mindset it helped him develop. Cardell also discusses the specific ways Stand for Children Tennessee helps connect the dots for citizens who want to get involved in education advocacy, and what is at risk when a state proposes taking over a local school district. 

Read more about Stand for Children Tennessee 

Learn more about the 901 Moral Budget Coalition

The natural topography and the social geography of Springfield, Massachusetts make it a place especially vulnerable to climate change. Samantha Hamilton is bringing Springfield residents together to develop climate solutions for their city. 

Samantha Hamilton is the Director of Coalition Building and Community Engagement at the Public Health Institute of Western Massachusetts in Springfield, MA. In this episode she explains how diverse coalitions – including a broad spectrum of residents, nonprofits, and municipal organizations – are best equipped to tackle complex and interconnected issues like air quality, housing, education, and health disparities. She also talks about her strategies for cultivating commitment in community participation, and how resident-guided problem solving can inform and impact local and state policy.

Quetzal Flores is a Grammy-winning musician who combines his immense creative skillset and his deep knowledge of cultural traditions to ignite community participation in resistance and resilience.  

In this conversation, Quetzal recounts growing up “in movement” with parents who were deeply involved in the civil rights organizing of the Chicano Movement. He describes East LA's historical significance, its current cultural landscape, and what's at stake in the neighborhood today. Quetzal also reflects on the musical and cultural experiences that have shaped his approach to community powerbuilding. 

Learn more about the Community Power Collective

Hear music from the band Quetzal

Watch some beautiful music videos from Quetzal and his band