In this episode of The Jentry Podcast, Jonathan Mason sits down with Will Kolbow, City Manager of Calimesa, California, for a conversation about growth, development, infrastructure, fiscal discipline, and the realities that sit behind local government decisions. Will shares his path from accounting and public agency finance to becoming a city manager. His background in finance gives him a unique lens on how cities grow, how public dollars are managed, and why long-term planning has to account for both community values and economic realities. The conversation explores Calimesa’s strategic priorities as a growing city, including open space preservation, public safety, economic development, retail shifts, industrial opportunity, housing, infrastructure, and the importance of balancing new development with the needs of existing residents. At its core, this episode is about the complexity behind the decisions people often assume should be simple. Will explains why infrastructure cannot always be built before development, why cities need a balanced tax base, why developers need predictability, and why local government will always require a human element that AI cannot replace. Takeaways There Is Always More Behind the Decision Will explains that residents often see the visible issue, but not the legal, financial, engineering, timing, liability, and risk management constraints behind it. Growth Has to Pay for Services Calimesa is thinking carefully about how residential, commercial, industrial, and experiential retail uses affect long-term tax revenue and public service costs. Development Requires Predictability For developers to invest millions before earning a dollar back, they need a process that is clear, stable, realistic, and rooted in communication. Infrastructure Timing Is Complicated While residents often want infrastructure built before homes or businesses, Will explains why upfront costs, state approvals, project phasing, and long timelines make that difficult in practice. Local Government Is Still a People Business AI can help with staff reports, research, and analysis, but it cannot replace empathy, trust, community relationships, council dynamics, or the human judgment required in public service. Chapters 00:00 E-commerce, Sears, Amazon, and operating in reality 01:05 Introduction to Will Kolbow 01:58 What makes Calimesa special 02:49 Will’s path from accounting to city management 05:00 Public finance, water districts, and bankruptcy experience 07:00 Becoming a city manager in Calimesa 08:43 The role of timing and fit in city manager hiring 09:46 Calimesa’s strategic planning process 11:00 Balancing growth, open space, and fiscal stability 13:49 Proposition 13, tax structure, and city finance 14:22 Retail shifts, e-commerce, and industrial opportunity 17:47 Why tax base diversity matters 18:58 Housing growth and development challenges 20:30 Market timing, public infrastructure, and past decisions 22:26 The city-developer partnership 23:24 Why developers need predictability 27:02 Communication, empathy, and public stewardship 28:07 Understanding the developer math 31:43 Last chance questions begin 33:05 Why infrastructure first is difficult in real life 36:20 The need for economic development capacity 38:26 AI and the limits of automation 42:02 Tradeoffs, risk, and what residents do not see 46:06 Ownership as a hidden development constraint 48:02 Why parks take longer than election cycles 50:08 Revitalizing downtown Calimesa 51:45 The Calimesa Insider podcast and local government education Keywords #WillKolbow #Calimesa #California #LocalGovernment #CityManagement #EconomicDevelopment #Infrastructure #StrategicPlanning #PublicFinance #Development #Housing #RetailDevelopment #IndustrialDevelopment #MunicipalLeadership #PublicService