『Harder Than It Looks: Parking Uncovered』のカバーアート

Harder Than It Looks: Parking Uncovered

Harder Than It Looks: Parking Uncovered

著者: Parker Technology
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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.

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  • EP 57: 850 Square Miles: How Peter Sherwill Runs Parking for the Biggest City in America
    2026/08/12
    In this episode of Harder Than It Looks, host Brian Wolff is joined by Peter Sherwill, Chief Public Parking Officer for the City of Jacksonville, the largest city by land area in the contiguous United States. Peter brings more than two decades of parking and mobility experience spanning valet, event parking, municipal operations, and private sector contracts, and now oversees a system of garages, surface lots, on-street parking, and enforcement across 850 square miles.Peter walks Brian through his winding path into parking, starting as a high school valet attendant and working his way through event parking at venues like Red Rocks Ampitheatre, municipal operations in Denver, and a private sector stop in Fort Myers before landing in Jacksonville. Brian and Peter dig into how Peter keeps a lean 40-person team motivated without a formal appreciation budget, how the department earned a seat at the table for major city projects, and how Jacksonville is modernizing decades-old technology while preserving the ambassador-like role of enforcement staff. They close with a look at the next big challenges facing curb management as downtown Jacksonville grows.Key Takeaways1. Motivation doesn't require a big budget. Without funds for employee perks, small gestures, such as dedicated a employee break room, new uniforms, "Win Wednesday" recognition meetings, have transformed a once-fragmented enforcement team into one that has each other's backs.2. If you want a seat at the table, you have to take initiative. Parking teams are often the last to know about city projects that affect the curb. Peter changed that in Jacksonville by proactively reaching out to other departments and showing up as a problem solver, not an afterthought.3. Modern technology should remove friction, not remove people. Jacksonville is rolling out multi-space meters, online permitting, and updated LPR systems, while intentionally keeping staff visible and approachable so automation doesn't replace the human side of the customer experience. 4. The Curb is everchanging. As downtown Jacksonville adds housing, a rebuilt stadium, and more nightlife, the parking team expects to expand enforcement hours, add residential permit programs, and manage rising demand from rideshare and delivery traffic. Episode Highlights[02:00] Introducing Peter Sherwill and his origin story.[04:00] Learning municipal parking in Denver and expanding paid parking in Fort Myers, Florida.[06:00] The surprise twist that turned a different job interview into an offer for Chief Public Parking Officer.[12:00] Keeping a lean team motivated without an appreciation budget - break rooms, new uniforms, and "Win Wednesday".[17:00] A technology rundown: multi-space meters, online permitting, new LPR systems, and upgraded garage equipment.[19:00] Stakeholder stories: booting a city council member's car and creative curb solutions for a century-old downtown business.[30:00] Cross-departmental collaboration on downtown revitalization, the new Jaguars stadium, and micro-mobility expansion.[36:00] How Peter earned parking a seat at the table early in major city projects.[38:00] Balancing automation with a human touch by turning enforcement staff into downtown ambassadors.[43:00] Looking ahead: curb demand from deliveries and rideshare, micro mobility, and expanding enforcement hours.[48:00] Lightning round: Peter's go-to phrase, hardest career challenge, and what he's most proud of.Notable Quotes"It's just parking, it's not rocket science. We can figure anything out." - Peter Sherwill"I will carry the baton for whatever project it is as far as I must, to hand it off to the next person. I don't just wait for that baton to come back - I take the next one." - Peter Sherwill"If you need something to be successful at your job, let us know what it is. As long as it's reasonable, we're going to get it for you. I don't think I've said no once." - Peter SherwillAbout the GuestPeter Sherwill is the Chief Public Parking Officer for the City of Jacksonville, overseeing a comprehensive system of parking garages, surface lots, on-street parking, and enforcement across 850 square miles - the largest city by land area in the contiguous United States.Peter has more than 20 years of experience in municipal and private sector parking operations, including event parking for sports and entertainment venues, short-term garage and valet operations at Denver International Airport, and municipal parking leadership in Denver and Fort Myers. He is recognized for optimizing revenue, developing high-performing teams, enhancing the customer experience, and advancing smart mobility technologies.Additionally, Peter currently serves as Secretary for the Florida Parking and Transportation Association.
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    55 分
  • EP 56: The Curb: Transportation's Toughest Puzzle with Benito Pèrez
    2026/07/29
    In this episode of Harder Than It Looks, host Brian Wolff sits down with Benito O. Pérez, AICP, CTP, CPM, PTMP, Section Chief for Transit Capital Statewide at the Illinois Department of Transportation.Benito’s career has moved through urban planning, civil engineering, transportation policy, curbside management, accessibility, and transit capital planning. But the common thread through all of it is connection: connecting planners and engineers, connecting agencies and advocates, connecting infrastructure decisions to real human experience, and connecting today’s transportation choices to the communities we want in the future.The conversation also gets into the curb: why it is one of the most contested and misunderstood spaces in transportation, how accessibility has to go beyond the parking space, and why public agencies need to think more intentionally about every user who interacts with streets, sidewalks, transit, bike lanes, parking, and the curb.Benito also shares what he’s working on now at IDOT, helping transit agencies across downstate Illinois access capital funding for buses, maintenance facilities, transfer centers, and long-term infrastructure needs. His advice is simple but important: don’t just plan for what you need today. Think about what your system needs to become.Key TakeawaysTransportation problems are rarely siloed. Parking, transit, biking, walking, land use, accessibility, and curbside management all intersect. The best solutions come when agencies and stakeholders stop treating them as separate conversations. The curb is where everything comes together. Benito describes the curb as a friction point where transportation systems meet land use, access, mobility, policy, and real-world user needs. Accessibility has to be built into the whole journey. Accessible parking matters, but the experience does not stop once someone gets out of the vehicle. Streetscapes, crossings, bike lanes, transit access, and signal timing all shape whether a place is truly accessible. Long-term planning requires more than today’s need. Benito encourages agencies to think about their 20-year buildout, especially when funding is available, so they do not solve today’s problem only to create tomorrow’s constraint. Public agencies and advocates need each other. Benito makes the case that advocates and practitioners are often working toward the same goals, but they need better communication, transparency, and trust to move things forward. Episode Highlights[02:00] Benito shares how growing up in a Navy family exposed him to transportation systems in Europe and shaped the way he thought about cities.[03:00] Why Benito first thought he wanted to be an architect, and how an advisor helped him realize he was more interested in the “architecture of space.”[06:00] A pivotal meeting with planners and engineers helped Benito realize he wanted to become a translator between disciplines.[09:00] Brian and Benito discuss why transportation, housing, land use, and parking have historically been siloed.[11:00] Benito explains how the rise of the car shaped zoning, street design, transportation policy, and the way communities developed.[20:00] Benito explains his current role at IDOT, overseeing transit capital funding outside of metro Chicago.[22:00] Why rural transit is often lifeline transportation for seniors, people with disabilities, and people accessing healthcare, food, and other essential services.[24:00] Benito explains why agencies should plan for their 20-year buildout, not just what they need right now.[30:00] Benito discusses the challenge of integrating ADA and accessibility into long-range transportation planning.[36:00] A powerful example of how flashing traffic signals can unintentionally create barriers for people with cognitive disabilities.[39:00] Where public sector leaders and operators should start if they want to do better around accessibility.[43:00] Why curbside management needs to be treated as a regional issue, not just a local one.[49:00] Lightning round: Benito’s go-to phrases, including “Curbside management is not a sprint, it’s a marathon.”Notable Quotes“Curbside management is not a sprint, it’s a marathon.” – Benito Pérez“It’s not a war on cars, it’s a war on the idea that car is the only option.” – Benito Pérez“We need to take a step back and think about both the infrastructure side of things and the operational side of things.” – Benito PérezAbout the GuestBenito O. Pérez, AICP, CTP, CPM, PTMP, is the Section Chief for Transit Capital Statewide at the Illinois Department of Transportation, where he helps oversee capital funding and support for transit agencies across Illinois outside of metro Chicago.His career has spanned urban planning, civil engineering, transportation policy, curbside management, accessibility, and multimodal transportation planning. Before joining IDOT, Benito served as Transportation Policy Director at ...
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    1 時間 3 分
  • EP 55: EV Charging Is Harder Than It Looks with David Weber
    2026/06/17
    In this episode of Harder Than It Looks, host Brian Wolff is joined by David Weber, Head of National Business Development for Parking at SWTCH Energy. David brings more than two decades of experience across the parking industry, starting as a valet at a Las Vegas casino before moving into operations, digital parking, business development, and now EV charging infrastructure.David’s path through parking has taken him across the parking industry. Along the way, he learned how to handle people, solve operational challenges, say yes to new opportunities, and build a career in an industry that has a way of pulling people back in.Brian and David dig into what parking operators and asset owners need to understand about EV charging: the misconceptions, the real costs, the role of incentives, load management, uptime, and why chargers should be treated as part of the broader parking ecosystem.David also explains why EV charging is less about becoming a major revenue stream and more about serving tenants and customers, and preparing parking assets for the future of mobility, including fleets and autonomous vehicles. Key TakeawaysEV charging is not plug-and-play. Installing chargers requires understanding power availability, building infrastructure, load management, incentives, customer needs, and long-term operational goals.EV charging is an amenity and a competitive advantage. For garages, office buildings, multifamily properties, and urban parking assets, EV charging is increasingly becoming something customers expect.Operators need to cut through misinformation. David addresses common misconceptions around EV fires, vehicle weight, charger placement, and whether existing garages can support EV adoption.The real cost is often infrastructure, not the charger. Chargers themselves have become more affordable, but electrical work, conduit, transformers, and power capacity can drive the true project cost.Parking assets are well-positioned for the next wave of mobility With the growing trend of EV drivers, autonomous vehicles, and electric fleets, parking operators already control valuable real estate that could become essential charging and mobility hubs. Episode Highlights[02:00] David shares his career story, from growing up near Buffalo to starting as a valet at The Mirage in Las Vegas. [05:30] What David learned from working at the ground level of parking operations [11:00] Why EV charging is “much harder than it looks” and what parking operators often underestimate. [13:00] Brian and David discuss misinformation around EVs, including fires, vehicle weight, and garage placement. [20:00] The EV charging checklist: budget, incentives, site walks, electrical capacity, and load management. [25:00] The future opportunity around electric fleets, self-driving cars, and overnight charging. [30:00] What installing EV chargers really will cost operators.[34:00] David gives a snapshot of EV adoption in the United States and where he thinks the market is headed.Notable Quotes:“If you’re just getting started out in any business and it’s a little over your head, go for it.” – David Weber“EV charging is an amenity that has to be there now. If someone has an EV car, they aren’t even looking at an apartment or a complex that doesn’t have EV charging.” – David Weber“You could put four chargers in for under $10,000 and get them paid off in a couple years no problem.” – David WeberAbout the GuestDavid Weber is the Head of National Business Development for Parking at SWTCH Energy, where he helps parking operators and asset owners integrate EV charging into their facilities and broader parking ecosystems.David has spent more than 25 years in the parking industry, beginning his career as a valet before moving into supervisory, district management, operations, and business development roles. He has a practical understanding of how parking operations work on the ground, how technology gets adopted in the field, and what operators need from partners introducing new solutions.At SWTCH Energy, David focuses on educating the parking industry about EV charging infrastructure, incentives, uptime, load management, and the future role parking assets can play in EV development and mobility operations. Known for his operational background, direct communication style, and resilience, David brings a practical perspective to one of the industry’s fastest-evolving ...
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    45 分
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