Harder Than It Looks: Parking Uncovered

In this episode, host Brian Wolff sits down with Jeff Siegler, author, urbanist, and founder of Revitalize or Die, for a candid conversation about civic pride, apathy, and how an overemphasis on parking might actually be holding our communities back. 

Jeff brings a unique perspective - challenging the idea that “more parking” equals “more progress.” He shares lessons from two decades helping towns revitalize, the emotional roots of civic decline, and why action is the antidote to apathy. 

The discussion touches on leadership, walkability, car culture, and how the health of a place directly impacts the health of its people. Whether you agree or disagree, this episode will make you rethink what really makes a city thrive. 

Key Takeaways: 
  • Apathy, not infrastructure, is often the real cause of civic decline. 
  • Parking is a utility, not a destination. Cities thrive when they build for people first, not cars. 
  • “Raise your standards” - better places begin with higher expectations from leaders and residents alike. 
  • Action cures apathy. Real progress starts with simple, visible change - planting flowers, picking up trash, cleaning sidewalks. 
  • Good design is good health. Where we live shapes our physical and mental well-being more than we realize. 
Main Topics & Timestamps: 
[3:30] Jeff's background growing up in a struggling rust belt town 
[8:45] Career path from Main Street director to revitalization consultant   
[12:20] Signs of community health vs. decline 
[16:15] Root causes: Apathy vs. technical problems 
[22:30] Breaking through apathy with small actions 
[28:45] The problem with obsessing over parking  
[35:20] Why great places don't need abundant parking 
[42:10] How cities should think about parking as a utility 
[48:30] New urbanism and walkable communities 
[52:15] Community transformation success stories 
[58:40] Design principles for parking in cities 
[64:20] What separates progressing vs. stuck communities 
[68:30] Hope for the future of towns and cities 
 
About Jeff Siegler: 
Jeff Siegler is an urbanist author and founder of Revitalize or Die; a consulting firm focused on helping revitalize struggling towns and cities. Jeff has been working in revitalization for the past two decades, including time serving as a Main Street as well as a statewide Main Street coordinator. He is also an elected commissioner in Pennsylvania, serving Pittsburgh proper. Jeff published his first book, “Your City is Sick” in 2023. 

What is Harder Than It Looks: Parking Uncovered?

We as parking professionals know that parking is hard. However, we make it look easy to those from the outside looking in. The myriad technologies, processes and people that a parking operator has to wrangle on any given day is mind-numbing, and every parking facility is unique. While certain verticals share similar pain points, we know better than many how nuanced every operation can be.


We created this podcast to facilitate connections and illuminate solutions to common problems within the parking and mobility industry. We aim to do so by highlighting the voices of experts in the space, discussing trends and forward-looking technological innovations, and providing professional food for thought. All in an effort to help one another get better at what we know is harder than it looks…parking a car.