Calimesa Insider

In this episode of the Calimesa Insider Podcast, City Manager Will Kolbow pulls back the curtain on a question many residents ask but few fully understand: What does a City Manager actually do?Instead of describing the role in theory, this episode walks through a real-world breakdown of the first two months of 2026. Listeners get a behind-the-scenes look at the wide range of responsibilities that come with managing a city—from infrastructure planning and regional coordination to budget oversight, development discussions, and public safety collaboration.The episode highlights how city management requires constant problem-solving and coordination across departments, agencies, and community partners. Topics include major infrastructure projects like the Cherry Valley Boulevard interchange, development planning such as Mesa Verde and Oak Valley Town Center, regional transportation coordination, budget management, and the day-to-day realities of leading a municipal organization.Subscribe to the Calimesa Insider Podcast for regular updates on development, infrastructure, city government, and community events in Calimesa.#LocalGovernment#CityManager#Calimesa#MunicipalGovernment#CityPlanning#PublicAdministration#Infrastructure#EconomicDevelopment

When a City Manager attends a conference, some residents immediately wonder: is it professional development… or a taxpayer-funded junket?In this episode of Calimesa Insider, City Manager Will Kolbow pulls back the curtain on what actually happens inside a statewide City Manager conference. From state budget deficit warnings and housing mandates to artificial intelligence policy discussions and infrastructure funding shifts, this episode explains how those conversations directly impact Calimesa.He walks through:• State fiscal uncertainty and revenue protection• Housing and homelessness funding trends• Infrastructure funding implications• Why Calimesa is ahead on AI policy• Strategic planning implementation and the March 21 public workshop• Leadership resilience and the council-manager form of governmentThis is not a highlight reel. It’s a behind-the-scenes look at how local government anticipates risk, protects taxpayer dollars, and strengthens institutional stability.🎙 Calimesa Insider is hosted by the City Manager and designed to bring transparency to how local government actually works.#LocalGovernment #CityManagement #Calimesa #PublicService #MunicipalLeadership #StrategicPlanning #ArtificialIntelligence #PublicSafety #CityCouncil #GovernmentTransparency00:00 Conference ‘Junket’ vs. Reality: What City Managers Actually Do00:43 Podcast Intro + Personal Note (A Proud Dad Moment)01:49 Why Napa, and Why Conferences Matter for Stewardship03:34 Conferences as Early-Warning Systems (Risk, Networks, Realism)10:06 Theme 1: State Fiscal & Policy Uncertainty—What It Means for Calimesa14:21 Housing, Homelessness & Public Safety Funding Pressures17:40 Strategic Alignment as a Budget Tool (Priorities Drive Decisions)19:05 Theme 2: AI in City Hall—Innovation with Guardrails & Transparency23:05 Governing in the Digital/Social Media Era: Trust, Facts, and Discipline27:49 Theme 3: Strategic Planning That ‘Sticks’ + Calimesa’s March 21 Workshop30:46 Leadership Resilience, Culture, and the Council-Manager Model33:29 Wrap-Up: Why This Was Stewardship (Not a Junket) + Subscribe

In this episode of Calimesa Insider, viewers get to know Edgar Garcia beyond the dais.Councilmember Garcia shares his personal journey as a husband and father of three, including raising a child with Down syndrome, and how those experiences have shaped his perspective on service, leadership, and community. He talks about why he and his family chose to make Calimesa their home, what stood out to them when they first arrived, and how living here influenced his desire to serve.The conversation also explores his professional background in education and family support, lessons learned from working with students and families, and why empathy, listening, and trust are essential in public service.This episode is part of the City’s ongoing effort to help residents better understand the people who serve their community — not in a political or campaign context, but as neighbors, parents, and public servants.📍 Learn more about the podcast: calimesa.gov/podcast

Most people encounter development at the very end — when a project reaches a public hearing or construction begins.This episode of the Calimesa Insider podcast explains what happens long before that moment.City Manager Will Kolbow walks through how development actually works from a developer’s perspective, including land assembly, financing, entitlement, infrastructure timing, City Council discretion, and the risks faced by both cities and investors.The episode explains why development decisions are rarely simple, why both approvals and denials carry consequences, and why understanding the full process matters.🎧 Listen now at calimesa.gov/podcast#LocalGovernment #CityPlanning #UrbanPlanning#CivicEducation #PublicPolicy #CommunityDevelopment#Infrastructure #LandUse #MunicipalGovernment

Every January 1, hundreds of new California laws quietly take effect. Some change daily life for residents and businesses. Others reshape how cities are required to operate — even if the public never sees those changes directly.In the first episode of the Calimesa Insider Podcast for 2026, City Manager Will Kolbow breaks down a focused list of new and newly operative state laws that will have the biggest real-world impacts this year.This episode covers:Minimum wage changes and how they ripple through the local economyNew rental housing habitability requirementsConsumer protections affecting food delivery, banking fees, and AI transparencyHousing and CEQA changes that affect how quickly projects move forwardState laws that limit local zoning discretionAnd a deeper dive into SB 707, a major update to the Brown Act that will change how public meetings work across CaliforniaThis is not a political discussion. These laws are already passed. The goal is to explain what actually changes in 2026, what residents may notice, and how cities like Calimesa are required to implement state law.If you have questions about a specific state law not covered in this episode, feel free to reach out via Instagram or email at calimesainsider@gmail.com.Thanks for listening, and thanks for staying informed.

This episode of the Calimesa Insider Podcast is a little different—and intentionally so.Rather than a highlight reel or a list of complaints, this is a candid year-in-review of what really happened in Calimesa in 2025: the moments that brought the community together, the behind-the-scenes work residents don’t always see, the challenges that tested us, and the progress that quietly moved the city forward.In this episode, we reflect on:Community events and why connection mattersThe people behind city services and organizational culturePublic safety milestones, including an ISO Class 2 ratingFiscal responsibility, balanced budgets, and long-term stabilityInfrastructure realities, including County Line RoadModernization efforts like online permittingStatewide advocacy for seniors through AB 1476Development updates and realistic timelinesWhat’s ahead for Calimesa in 2026 and beyondCalimesa is 35 years old—and still growing into the city it wants to become. This episode is about transparency, context, and informed conversation—because good governance starts with shared understanding.Whether you’ve followed the podcast all year or you’re listening for the first time, this episode is a meaningful place to start.🎧 New episode available now.

In this special Town Hall edition of the Calimesa Insider Podcast, City Manager Will Kolbow is joined by City Engineer Mike Thornton and Transportation Project Manager Brandon Reyes to explain the long-awaited reconstruction of the Cherry Valley Boulevard Interchange.This episode answers the questions residents ask most:Why the interchange has taken years to reach constructionHow Caltrans approvals and environmental review affect timelinesWhat a Diverging Diamond Interchange (DDI) is and why it was selectedHow construction will be phased to maintain access and emergency responseWhy developers can’t simply build a $70 million interchangeHow the City is pursuing state and federal transportation fundingIf you commute through Cherry Valley Blvd. or want a clear, factual explanation of how major infrastructure projects actually happen in California, this episode provides the full context — without speculation.More information and referenced episodes: Calimesa.gov/podcast00:00 Introduction to the Cherry Valley Boulevard Interchange Project00:42 Welcome to the Calimesa Insider Podcast01:13 Town Hall Meeting Overview04:47 Panelist Introductions and Project History09:07 Challenges and Frustrations with Caltrans13:14 Funding and Financial Overview16:33 Plan Specifications and Estimates (PSE) Phase21:39 Diverging Diamond Interchange Design Explained28:06 Singleton Road Access and Missing Ramps29:21 Calimesa Boulevard Realignment and Singleton Interchange31:04 Roberts Road Connection Issues35:30 Construction Phases and Traffic Management42:01 Funding Challenges and Grant Programs49:36 Q&A and Development Updates58:59 Closing Remarks and Contact Information

In this special episode of the Calimesa Insider podcast, City Manager Will Kolbow sits down with Councilmember Eric Cundieff for an in-depth, non-political conversation about his life, his service, and his path to the Calimesa City Council.Eric shares stories from growing up in the Yucaipa–Calimesa area, what inspired him to join the U.S. Navy, and a few memorable moments from his time at sea. He also talks about his years as a San Bernardino County Deputy Sheriff, how he became involved in the Calimesa Planning Commission, and what eventually led him to run for City Council.We also explore what he’s learned along the way, the surprises of serving in local government, and his reflections on community, leadership, and public service.Topics in this episode include: • Growing up in the Yucaipa–Calimesa community • Influences and early experiences that shaped his path • Joining the U.S. Navy and stories from his time in service • A career with the San Bernardino County Sheriff’s Department • How he became a Planning Commissioner • What inspired him to run for City Council • Lessons learned about public service and community leadership Whether you’re a longtime resident or new to Calimesa, this episode offers a warm, personal look at one of your Councilmembers and the experiences that shaped him.🎧 Listen to more episodes of the Calimesa Insider: https://calimesa.gov/podcast📅 Watch City Council meetings live or on demand: https://calimesa.gov/youtube00:00 Introduction to Today's Episode01:40 Upcoming Community Events04:01 Interview with Councilmember Eric Cundieff04:47 Eric Cundieff's Early Life and Influences09:55 Joining the US Navy12:08 Life in the Navy14:57 Stories from the White House26:21 Transition to Law Enforcement30:21 Entering Local Politics38:55 Balancing Development and Community Benefits40:15 Lessons from the Planning Commission41:47 Decision to Run for City Council44:10 Campaign Challenges and Surprises44:24 Public Safety and Budget Realities48:17 Running for Office: Experiences and Reflections54:27 Council Dynamics and Responsibilities58:06 Future Plans and Community Engagement01:13:52 Advice for Aspiring Public Servants01:16:12 Conclusion and Upcoming Events

In this episode of the Calimesa Insider podcast, we’re breaking down one of the most confusing—and most important—documents every homeowner receives: your annual property tax bill. Whether you pay it directly or through an impound account with your mortgage, the numbers on that bill can vary dramatically from one home to the next, even on the same street. Today, we explain why.City Manager Will Kolbow walks through each section of the Riverside County tax bill, explains how Proposition 13 and Mello-Roos (CFDs) shape what you pay, and uses real Calimesa examples—from long-time homeowners to the newest Summerwind Trails residents—to show how assessed value, voter-approved bonds, and development-specific special taxes all add up. By the end of the episode, you’ll understand why your bill looks the way it does, why your neighbor’s might look completely different, and where every dollar actually goes.We also preview this Monday’s City Council meeting, including:• Inclusionary Housing Ordinance Update (Ordinance 418) – adding an in-lieu fee option to support affordable housing.• County Line Road Corridor Project Close-Out – a formal administrative step after years of delays, frustration, and construction impacts.Finally, Will provides a detailed update on the Oak Valley Town Center bond lawsuit, including the recent federal court order granting an interlocutory appeal and what that means for the timing of the case.Chapters:00:00 Introduction to Property Tax Season00:36 Welcome to Calimesa Insider Podcast01:26 City Council Meeting Preview02:43 County Line Road Project Closure04:06 Oak Valley Town Center Bond Lawsuit Update07:13 Understanding Your Property Tax Bill08:15 Proposition 13 and Melrose Act Explained11:37 Reading a Property Tax Bill: Real Examples28:46 Summary and Key Takeaways29:52 Closing Remarks and Upcoming EventsIf you’d like help interpreting your own property tax bill, you’re welcome to send in a redacted copy for a future episode.👉 Watch City Council live or on demand: calimesa.gov/youtube👉 Subscribe to the podcast: calimesa.gov/podcastAvailable on YouTube, Spotify, Apple Podcasts, and more.Thanks for tuning in, and have a wonderful Thanksgiving!#CalimesaInsider #Calimesa #PropertyTax #CaliforniaTaxes #Prop13 #MelloRoos #LocalGovernment

In this Halloween edition of the Calimesa Insider, City Manager Will Kolbow breaks down how Calimesa’s Mobile Home Rent Stabilization Ordinance actually works: why it exists, what it covers, where the City’s authority begins and ends, and how petitions (like capital improvements or “fair return”) are reviewed by an independent Hearing Officer. If you’ve ever wondered, “Can the City just deny a rent increase?”—this episode explains the legal framework and due-process steps that guide every decision.We also preview Monday night’s City Council meeting (Nov 3, 6 PM) including a presentation from the Blue Zones Project and consideration of a Strategic Plan update with Jacob Green & Associates.00:00 Introduction to Calimesa's Mobile Home Rent Regulation01:27 Upcoming City Council Meeting and Blue Zones Project02:41 Understanding Calimesa's Mobile Home Rent Stabilization Ordinance03:32 Historical Context and Evolution of the Ordinance05:36 Key Features and Provisions of the Ordinance09:55 Petition Types and Procedures16:09 Hearing Officer System and Fairness in the Process19:19 Clarifying Misconceptions and Legal Safeguards25:25 Conclusion and Final Thoughts

Join City Manager Will Kolbow in this episode of the Calimesa Insider Podcast as he unpacks the complexities of economic development in Calimesa. Addressing common questions from residents about the city's infrastructure and planning decisions, Will explains the factors influencing retail and industrial growth. Topics include funding challenges, the impact of consumer behavior on development, and the realities of attracting businesses in a competitive market. Additionally, updates are provided on the city's upcoming projects and council meetings. Tune in to gain a deeper understanding of how your city government works to balance growth and maintain community values.00:00 Introduction and Viewer Questions01:20 City Council Meeting Announcements02:32 Addressing Viewer Comments03:14 Road Maintenance and Funding Challenges06:55 Homelessness in Calimesa11:57 Economic Development Overview13:28 Retail Trends and Market Realities15:01 Warehouse Demand and Land Use24:10 Infrastructure and Economic Strategy29:01 City's Role in Retail Development39:18 Conclusion and Contact Information

Join City Manager Will Kolbow for a special edition of the Calimesa Insider Podcast, where we discuss the 2025 State of the City. Learn about exciting new projects, modernized permits, public safety, and future plans. Discover the details behind our latest pavement work, the new Calimesa Library, and enhancements in energy efficiency. We’ll also cover updates on the Cherry Valley Boulevard interchange, and encourage community involvement in our strategic plan. Tune in to stay informed about your city’s progress and how you can contribute!00:00 Welcome to the Calimesa Insider Podcast00:50 Special Edition: 2025 State of the City Address02:21 City Growth and Development Updates03:39 Infrastructure Improvements: Roads and Library05:54 Energy Efficiency Initiatives06:45 Modernizing Permits and Big Developments08:25 Public Safety: Police, Fire, and Public Works10:14 Parks and Recreation Projects11:05 Cherry Valley Boulevard Interchange12:19 Financial Health and Strategic Planning13:02 Community Engagement and Final Thoughts15:08 Conclusion and Upcoming Events

Welcome to the Calimesa Insider Podcast! In this episode, City Manager Will Kolbow hosts an engaging discussion with Calimesa’s Public Works Director, Mari Shakir, and Public Works Superintendent, Kyle Coney. They delve into their professional backgrounds, career journeys, and the vital role of the Public Works department in maintaining city infrastructure. The conversation covers various challenges faced due to limited staffing, the importance of public safety, and how the department prioritizes its time and resources. Additionally, the episode touches on critical compliance programs like NPDS for stormwater management and SB 1383 for waste diversion. Don't miss this insightful episode to understand what goes on behind the scenes to keep Calimesa running smoothly!00:00 Welcome to Calimesa Insider Podcast00:15 Meet the Public Works Team04:16 Challenges of Managing Public Works in a Small City07:20 Public Perception and Communication13:22 Behind the Scenes: Compliance and Regulations21:29 Future Opportunities and Challenges25:04 Closing Remarks and Upcoming Events

In this episode, we cover a wide range of updates onthe City's capital and development projects. Key capital projects discussed include the Cherry Valley Boulevard Interchange and Singleton Road Interchange, and updates on major development projects like Summerwind Commons, Mesa Verde, and Oak Valley Town Center. Additionally, don't miss critical announcements about the upcoming City Council meeting and the 2025 State of the City event.Tune in to stay informed about the latest happenings within Calimesa's city government and community development efforts.00:00 Welcome to the Calimesa Insider Podcast00:54 Upcoming City Council Meeting01:41 Cherry Valley Boulevard Interchange Update07:00 Singleton Road and County Line Road Interchanges09:10 County Line Road and Pavement Management14:19 Calimesa Library and Park Expansion15:53 Development Projects Overview16:21 Summerwind Commons and Stearns Property19:50 Mesa Verde Specific Plan Amendment24:24 Oak Valley Town Center Legal Battle30:39 Conclusion and Upcoming Events

In this episode of Calimesa Insider, host and City Manager Will Kolbow explores the complex history and current state of highway funding, with a focus on California. From the golden age of gas taxes to the rise of toll roads, this episode delves into the evolution of road funding mechanisms and the factors driving the resurgence of tolls. Learn about the fiscal challenges, political decisions, and innovative solutions shaping our roads today. Whether you're a daily commuter or just curious about infrastructure, this comprehensive look at toll roads will provide valuable insights.00:00 Introduction to Toll Roads00:17 Historical Context of Road Funding03:41 California's Unique Approach12:42 The Decline of Gas Tax Revenue22:51 Challenges in Modern Road Construction31:05 Development Impact Fees: Funding New Infrastructure31:44 Limitations and Legal Constraints of Impact Fees32:59 Case Study: Orange County Toll Roads35:09 Challenges in Funding Road Expansion37:36 California's Shift in Transportation Policy41:07 The Role of Tolls in Modern Road Funding47:11 Toll Roads Across the United States48:59 Public Perception and Political Challenges of Tolls56:07 Conclusion: The Future of Road Funding57:17 Community Announcements and Events

Join us on the Calimesa Insider Podcast as we sit down with Deputy City Manager and City Clerk Darlene Gerdes. Darlene shares her nearly two decades of experience guiding Calimesa through significant growth, her pivotal role in the creation of the new library, and the importance of mobile home rent stabilization in the community. Gain insight into the inner workings of the city government and hear about Darlene's personal journey and dedication to public service. Don't miss this engaging episode live from the Calimesa Public Library!00:00 Introduction to the Calimesa Insider Podcast00:38 Meet Darlene Gerdes: Deputy City Manager and City Clerk00:58 Darlene's Journey in Local Government02:15 Changes in Calimesa Over the Years03:08 Challenges and Growth at City Hall04:18 Evolving Responsibilities and Roles05:32 The New Library: A Community Achievement08:02 Mobile Home Rent Stabilization Ordinance13:38 Community Misconceptions and Clarifications16:15 Motivation and Passion for Public Service18:40 Memorable Moments and Advice for Aspiring Public Servants24:03 Future Hopes for Calimesa25:55 Closing Remarks and Upcoming Events

Join host and City Manager Will Kolbow on the Calimesa Insider Podcast for an exciting update on the major expansion happening at Fourth Street Park, soon to be renamed Mountainview Park. Discover the details of this extensive project, including construction updates, new amenities like pickleball courts, and a brief history of the park. Additionally, learn all about pickleball—the fastest growing sport in America—with a comprehensive guide for beginners. This episode also highlights community feedback and the dedication of Calimesa’s Public Works team. Don't miss this episode for all the latest on your local parks and more!00:00 Big Changes at Fourth Street Park00:22 Introduction to the Calimesa Insider Podcast01:15 Community Appreciation and Public Works02:56 Overview of Calimesa Parks03:43 History and Expansion of Fourth Street Park08:40 Pickleball: The Fastest Growing Sport in America11:12 Pickleball Rules and Gameplay14:17 Pickleball Culture and Community15:25 Conclusion and Upcoming Events

Join us for a packed episode of the Calimesa Insider Podcast! In this episode, we cover the latest in the saga of the new signals at the County Line Road interchange, provide a sneak peek of two major public hearing items for the next City Council meeting, and take you behind the scenes of our recent advocacy trip to Washington D.C. We also discuss upcoming community events including the Friday Food Roundup and the grand opening of our new library. Stay informed on city government workings with host and City Manager, Will Kolbow.00:00 Introduction and Podcast Overview00:39 Podcast Philosophy and Approach03:10 Community Events and Announcements05:03 Traffic Signals at County Line Road Interchange09:31 Summerwind Trails Specific Plan Hearing Preview18:15 QR Bircher Logistics Center Development Agreement25:07 Advocacy Trip to Washington DC37:56 Conclusion and Upcoming Events

In this episode of the Calimesa Insider Podcast, City Manager Will Kolbow delves into the responsibilities and challenges of the City Manager role. The episode explores the unique structure and fiscal health of Calimesa, highlighting its balanced budget for the fiscal year 2025-2026, infrastructure investments, and public safety allocations. Will also shares personal anecdotes and addresses the importance of respectful public interactions. Stay informed on city governance, budget details, and community updates in this comprehensive episode.00:00 Introduction and Podcast Overview01:01 City Manager's Weekly Update02:28 Fireworks Safety Reminder03:27 Understanding the Role of a City Manager05:21 Challenges Facing California Cities07:32 Calimesa's Fiscal Year 2025-2026 Budget11:02 Future Growth and Infrastructure Plans12:13 The Unique Challenges of Being a City Manager14:31 Conclusion and Final Thoughts

Join us for the 50th episode of the Calimesa Insider Podcast. Host and City Manager Will Kolbow takes us on a historical journey, exploring Calimesa's evolution from indigenous roots through incorporation, the rise of master-planned communities, and how the modern economy has sparked a warehouse boom. Learn about the intricate history, key developments, and future plans for the city. We also provide updates on the upcoming City Council meeting, community events like Popsicles in the Park, and the Summer Lunch Program. Don't miss out on this comprehensive look at Calimesa's past, present, and future!00:00 Celebrating Episode 50 and 35 Years of Calimesa01:15 Upcoming City Council Meeting and Community Events03:49 A Listener's Request: The History of Calimesa04:03 Native American Roots and Early Settlers05:09 The Mexican Rancho Era and American Settlement06:15 The Birth of Calimesa: From Community to City09:26 The Push for Incorporation and Cityhood11:23 The Oak Valley Specific Plan and Development Disputes18:01 Modern Master Plan Communities: Summerwind Ranch and Mesa Verde23:05 Balancing Growth and Preservation in the 21st Century28:55 Conclusion and Future Outlook for Calimesa