The Jentry Podcast

Jonathan Mason

The Jentry Podcast highlights government leaders who are pioneering innovative solutions in jobs, affordable housing, childcare, workforce development, and local investment—transforming urban, suburban, and rural communities across America. A new generation is coming of age. Millennial and Gen Z community stakeholders and leaders are redefining civic engagement and community ownership. The New Jentry is not about displacement—it’s about ownership. It’s a generation committed to investing in and strengthening their communities for the long term. By demystifying local government, we’re making it more accessible ensuring that the next generation is informed, engaged, and empowered to shape the places they call home. We spotlight the changemakers shaping the future of our communities—and discover how each person can take action where they live. The Jentry Podcast is hosted by Jentry & Co. Founder, Jonathan Mason.

  1. Ep. 67 - Small Borough, Big Infrastructure: Leading Souderton Forward (with Sara Jarrett Eaton)

    4D AGO

    Ep. 67 - Small Borough, Big Infrastructure: Leading Souderton Forward (with Sara Jarrett Eaton)

    In this episode of The Jentry Podcast, Jonathan Mason sits down with Sara Jarrett Eaton, Borough Manager of Souderton Borough, Pennsylvania, for a conversation about public service, infrastructure, and what it really takes to run a small municipality. Sara comes from a family rooted in local government and public service, with her grandfather, father, and uncle all serving in municipal leadership roles. Her own path took her from a small borough office where she handled nearly everything, to a larger municipality, and eventually to Souderton, where she quickly stepped into the borough manager role. The conversation explores aging infrastructure, wastewater challenges, affordable housing constraints, police hiring, recreation, libraries, and the reality of wearing many hats in local government. Sara also shares how Souderton is finding creative ways to stretch limited resources, including partnering with a local prison work release program to support public works projects. At its core, this episode is about the unglamorous but essential work of local government and why small communities need leaders who can balance service, creativity, and long-term responsibility. Takeaways Public Service Runs Deep: Sara’s path into local government was shaped by generations of public servants in her family, as well as a broader commitment to community impact. Small Boroughs Require Big Range: In a small municipality, leaders often handle everything from finance and zoning to recreation, infrastructure, staffing, and resident concerns. Infrastructure Is the Long Game: Souderton’s wastewater plant, roads, parks, and public facilities all reflect the same challenge facing communities nationwide: aging infrastructure that is expensive and slow to fix. Creativity Can Stretch a Budget: By partnering with a local prison work release program, Souderton saved significant landscaping costs while creating a meaningful community service opportunity. Housing Is Limited by Space: Souderton is in an expensive county and has very little vacant land, which makes housing affordability and new development especially difficult. Chapters 00:00 Introduction and Souderton’s people-first identity 02:59 A family rooted in public service 04:45 Sara’s path into municipal management 07:28 Trial by fire in the borough manager role 11:17 Aging infrastructure and wastewater priorities 13:34 Doing more with less 13:53 Prison work release partnership 18:31 Technology and budgeting tools 20:30 Wearing multiple hats in local government 21:20 Planning versus recreation 23:21 Housing affordability in Souderton 25:54 Education, libraries, and community support 28:58 Last chance questions begin 30:00 Police civil service hiring challenges 32:55 The need for parks and recreation capacity 34:14 Explaining the true cost of local government 37:34 Resource allocation decisions 39:39 The wastewater plant as the major long-term challenge 41:16 Final reflections on Souderton Keywords #SaraJarrettEaton #Souderton #Pennsylvania #LocalGovernment #BoroughManagement #Infrastructure #Wastewater #HousingAffordability #PublicWorks #ParksAndRecreation #MunicipalLeadership #CommunityDevelopment

    43 min
  2. Ep. 66 – Housing Is a Lifecycle: Planning Growth in Caledonia (with Todd Willis)

    MAY 12

    Ep. 66 – Housing Is a Lifecycle: Planning Growth in Caledonia (with Todd Willis)

    In this episode of The Jentry Podcast, Jonathan Mason sits down with Todd Willis, Village Administrator of Caledonia, Wisconsin, for a conversation about growth, housing, and the long-term planning challenges facing communities across the country. Located along Lake Michigan, Caledonia blends urban, suburban, and rural character all within one community. That creates opportunity, but it also creates tension around density, development, infrastructure, and housing expectations. Todd shares how Caledonia is approaching these challenges through comprehensive planning, community engagement, and a lifecycle housing strategy designed to support residents at every stage of life. The conversation explores zoning, development incentives, TID districts, employer needs, transportation access, and the hidden realities behind housing development. At its core, this episode is about balancing community character with future growth while making sure residents can continue to live, work, and age within the same community. Takeaways Housing Is a Lifecycle Communities need housing options for every stage of life from apartments and starter homes to family housing and senior-friendly living. Growth Requires Balance Caledonia’s blend of urban and rural character creates ongoing tension around density, open space, and development expectations. Development Is More Complex Than People Realize Projects involve years of negotiations, infrastructure planning, financing discussions, and public process long before residents ever see a proposal. Communication Shapes Trust Todd emphasizes accessibility, transparency, and listening as critical parts of local government leadership. Economic Development and Housing Are Connected Housing shortages directly affect workforce availability, business retention, transportation systems, and long-term economic growth. Chapters 00:00 Introduction and Wisconsin life 02:31 What makes Caledonia unique 03:43 Todd Willis’ journey into public service 06:30 Comprehensive planning and community engagement 10:03 Bridging the disconnect between government and residents 13:29 Housing shortages and regional planning 18:38 Development incentives and conservation subdivisions 20:45 Housing as a lifecycle strategy 22:51 Explaining TID districts 26:05 Public land and development opportunities 31:06 Last chance questions begin 32:04 AI and ordinance drafting 35:37 The human side of development 36:59 Tradeoffs and development timelines 39:03 Hidden constraints to development 40:40 Long-term risks beyond election cycles 41:31 Free money and community investments 43:44 Final reflections Keywords #ToddWillis #Caledonia #Wisconsin #Housing #EconomicDevelopment #UrbanPlanning #LocalGovernment #LifecycleHousing #CommunityPlanning #TID

    45 min
  3. Ep. 65 – Growth Without Losing Identity: A Mayor’s Plan for Burgaw (with Olivia Dawson)

    MAY 3

    Ep. 65 – Growth Without Losing Identity: A Mayor’s Plan for Burgaw (with Olivia Dawson)

    In this episode of The Jentry Podcast, Jonathan Mason sits down with Mayor Olivia Dawson of Burgaw, North Carolina, a hands-on leader navigating one of the toughest balancing acts in local government growth versus identity. Burgaw is a small-town community just outside Wilmington, known for its courthouse square, tight-knit culture, and deep local roots. But like many communities across the country, growth is coming, bringing pressure on infrastructure, housing, and long-term planning. Mayor Dawson shares how Burgaw is preparing through strategic planning, infrastructure investment, and a more intentional approach to housing. The goal is not just growth but the right kind of growth. The conversation explores housing attainability, the need for diverse housing options, infrastructure constraints, and the reality that communities must evolve to survive. At its core, this episode is about protecting what makes a place special while making sure the next generation has a reason to stay. Takeaways Growth Is Coming Ready or Not Burgaw has held back growth for years, but its proximity to Wilmington and regional demand mean expansion is inevitable. The focus now is managing that growth intentionally. You Cannot Grow Without Rooftops New businesses, restaurants, and amenities do not come without population growth. Housing is the foundation for everything else a community wants to build. Attainability Matters as Much as Affordability It is not just about lower cost housing. Communities need a full range of options including apartments, townhomes, and next-step housing so residents can stay as their lives evolve. Infrastructure Is the Bottleneck Water, sewer, and utilities are the biggest constraints to growth. Without infrastructure, development cannot move forward. Communities Must Evolve to Survive If towns do not create opportunities for the next generation, they risk losing them to other places that do. Chapters 00:00 Introduction and Burgaw’s identity 01:39 The Hallmark feel of Burgaw 02:58 Mayor Dawson’s path to leadership 03:40 Strategic priorities and growth planning 05:39 Why Burgaw is positioned for growth 07:02 Infrastructure planning and challenges 09:03 Housing gaps and missing middle 11:48 Keeping the next generation in town 13:13 Zoning, permitting, and development 16:13 Doing more with less in small towns 18:46 Technology and efficiency in government 21:55 Education, childcare, and community needs 25:58 Last chance questions 30:52 Long-term infrastructure challenges 32:14 The real housing bottleneck 33:46 Resource allocation decisions 37:03 Final reflections Keywords #OliviaDawson #Burgaw #NorthCarolina #SmallTownGrowth #Housing #Infrastructure #EconomicDevelopment #LocalGovernment #CommunityPlanning #RuralDevelopment

    40 min
  4. Ep. 64 – Teamwork Built This: How Ashland Delivers More with Less (with Michael Herbert)

    APR 27

    Ep. 64 – Teamwork Built This: How Ashland Delivers More with Less (with Michael Herbert)

    In this episode of The Jentry Podcast, Jonathan Mason sits down with Michael Herbert, Town Manager of Ashland, Massachusetts, for a conversation that blends leadership, lived experience, and the real financial pressures shaping local government today. Ashland has delivered over $200 million in capital projects—from schools to public safety to downtown infrastructure—while operating with one of the lowest per capita budgets in its region. How? Michael says it comes down to one word: teamwork. But behind the results is a harder reality. Rising fixed costs, state-imposed tax caps, and increasing demand for services are forcing communities to make difficult trade-offs. Michael walks through the tension of potentially cutting staff, slowing projects, and asking residents to support tax overrides just to maintain core services. The conversation also dives into housing policy, state vs. local control, financing challenges, and why many well-intentioned policies fail in practice. At its core, this episode is about the complexity of governing—and the discipline required to lead through it. Takeaways Teamwork Is the Ultimate Force Multiplier Ashland’s ability to deliver major projects with limited resources comes from coordination across departments, strong volunteers, and a culture of collaboration—not siloed work. Doing More with Less Has a Breaking Point With property tax growth capped at 2.5% while costs rise much faster, municipalities are forced into tough decisions—cut staff, stop projects, or ask residents to pay more. You Can’t Run Government Like a Business Government is designed to move slower and more deliberately. It prioritizes stability and services over profit—which makes efficiency look very different than in the private sector. Housing Policy Is More Complicated Than It Looks State-level mandates can override local control, but the solutions don’t always match the problem—especially when affordability challenges are tied to single-family housing, not just apartments. Financing Is the Hidden Constraint Most people don’t see it, but projects often fail not because of zoning or land—but because the numbers simply don’t work due to interest rates, construction costs, and capital markets. Chapters 00:00 Introduction and Ashland overview 01:18 Budget pressures and tax constraints 06:14 Ashland’s “secret sauce”: teamwork 07:57 Michael Herbert’s personal journey 15:05 From recovery to leadership 18:17 Strategic priorities moving forward 21:19 Doing more with less in practice 23:51 Regionalization and efficiency 25:27 $200M in capital projects explained 26:48 Housing growth and controversy 30:34 State vs local housing policy 34:20 Development constraints and financing 40:23 Last chance questions 45:08 Why government moves slower 48:26 Financing as the real bottleneck 49:47 Culture takes time to build 50:44 Resource allocation scenarios 53:13 Final reflections Keywords Michael Herbert, Ashland Massachusetts, local government, economic development, housing policy, municipal finance, tax caps, public sector leadership, teamwork, infrastructure, capital projects, zoning, development financing

    55 min
  5. Ep. 63 – Economic Development Is a Long Game: Rebuilding Janesville (with Jimsi Kuborn)

    APR 13

    Ep. 63 – Economic Development Is a Long Game: Rebuilding Janesville (with Jimsi Kuborn)

    In the Season 2 Premiere of The Jentry Podcast, Jonathan Mason sits down with Jimsi Kuborn, Economic Development Director of Janesville, Wisconsin, to explore what it really takes to rebuild a city after economic shock, and why true progress in local government is always a long game. Janesville faced a defining moment when the closure of a major General Motors plant wiped out millions of square feet of industrial space. Instead of folding, the city leaned into grit, partnerships, and long-term strategy to rebuild its economic foundation. Jimsi shares her unconventional path into economic development from retail and real estate to “selling cities”, and how that mindset shapes her work today. The conversation dives into industrial redevelopment, housing constraints, regional collaboration, and the reality of doing more with less inside local government. At its core, this episode is about patience, persistence, and the discipline required to build something that lasts not just for today, but for generations. Takeaways Economic Development Is a Long Game: Real change doesn’t happen in a year or an election cycle. Projects take years of planning, partnerships, and execution before results are visible and even longer before they’re fully felt. Grit and Community Pride Drive Comebacks: After losing a massive industrial base, Janesville rebuilt through resilience, strong public-private partnerships, and a community that refused to give up. You’re Not Creating Jobs, You’re Creating the Environment: Local government’s role isn’t to directly create jobs. It’s to build the conditions like land, infrastructure, incentives, so the private sector can. Housing Is the Constraint Everywhere: From Midwest cities to coastal markets, housing challenges are driven by the same forces: rising costs, infrastructure expenses, and difficulty making projects financially viable. Creativity Comes From Constraints: Whether it’s cutting a budget in half or structuring tax increment districts, the best solutions often come when resources are limited and priorities are forced into focus. Chapters 00:00 Introduction and Janesville’s story 01:52 What makes Janesville unique 03:24 From fashion to economic development 04:33 Why economic development matters 06:32 Rebuilding after GM closure 07:09 Doing more with less 09:29 Regional collaboration vs competition 13:17 Tools and incentives for growth 16:15 Housing challenges and costs 23:14 Unlocking land and development 24:57 Infrastructure strategy and TIF 29:46 Public investment driving private growth 30:50 Education and workforce pipeline 34:31 Last chance questions 41:35 Economic development is a long game 53:55 Final reflections Keywords Jimsi Kuborn, Janesville Wisconsin, economic development, industrial redevelopment, housing crisis, tax increment financing, public private partnerships, workforce development, regional collaboration, city planning, infrastructure, local government

    55 min
  6. Ep. 62 – Growth Without Displacement: Zebulon’s Plan for What Comes Next (with Shannon Johnson)

    MAR 24

    Ep. 62 – Growth Without Displacement: Zebulon’s Plan for What Comes Next (with Shannon Johnson)

    In this Season 1 finale and one-year anniversary episode of The Jentry Podcast, Jonathan Mason sits down with Shannon Johnson, Community & Economic Development Director of Zebulon, North Carolina, for a conversation that captures the heart of what this podcast has been about from the beginning. Zebulon is at a turning point. Growth is accelerating. Investment is coming. Demand is rising. But Shannon is asking a different question than most: What happens to the people who were already here? Drawing from a career that spans federal work, entrepreneurship, and local government, Shannon explains why traditional economic development—focused only on jobs and tax revenue—is incomplete. Instead, she’s building a model that connects community, housing, infrastructure, and long-term outcomes into one strategy. The conversation explores gentrification, housing affordability, small business displacement, and the invisible work required to build a community that lasts. At its core, this episode is about doing the hard work early—so success doesn’t come at the cost of the people who made the place what it is. Takeaways Growth Without Intention Leads to Displacement: Zebulon’s affordability and proximity to Raleigh are driving rapid development. But without proactive planning, rising values and rents can push out residents and legacy businesses. Economic Development Must Be Redefined: Success isn’t just jobs or tax revenue. It’s whether a community remains stable, diverse, and livable over time. Shannon’s approach connects economic growth with real community outcomes. Small Town Growth Happens Fast—and Feels It Immediately: In a smaller town, it doesn’t take much to change everything. A few developments can reshape entire neighborhoods in months—not years. Entrepreneurship Builds Local Ownership: Through partnerships like Wake Tech’s Launch program, Zebulon is investing in local entrepreneurs to ensure growth includes people from the community—not just outside investors. The Most Important Work Is Invisible: Housing preservation, community land strategies, and long-term planning aren’t flashy—but they determine whether a community thrives or fractures over time. Chapters 00:00 Season 1 finale introduction 01:48 What makes Zebulon different 04:15 History, diversity, and identity 06:41 Why public input matters 09:05 Rethinking economic development 13:56 What “success” actually means 16:21 Growth, taxes, and infrastructure 23:20 Shannon’s career path 25:42 Strategic planning and priorities 30:30 Housing, gentrification, and displacement 35:14 Entrepreneurship and local business 42:04 Business retention challenges 47:39 The biggest challenge: preservation 54:22 What Zebulon looks like in 25 years 58:45 Advice for the next generation Keywords Shannon Johnson, Zebulon North Carolina, economic development, community development, housing affordability, gentrification, small town growth, Wake County, entrepreneurship, local government, civic leadership, urban planning, community preservation

    1 hr
  7. Ep. 61 – Doing Good vs Feeling Good: Leadership Lessons from Ohio (with Dani Isaacsohn)

    MAR 17

    Ep. 61 – Doing Good vs Feeling Good: Leadership Lessons from Ohio (with Dani Isaacsohn)

    In this episode of The Jentry Podcast, host Jonathan Mason sits down with Ohio State Representative Dani Isaacsohn, who serves as Minority Leader in the Ohio House of Representatives. The conversation explores Isaacsohn’s path to public service, the values that shaped his leadership, and the work being done to restore balance and opportunity across Ohio. Isaacsohn reflects on growing up in a family of immigrants who instilled in him the idea that being born in the United States is a gift and that the responsibility of that gift is service to others. That perspective led him from grassroots organizing during President Obama’s 2012 campaign to leadership in the Ohio legislature. The conversation dives into the major policy issues shaping communities across Ohio, including housing supply, education outcomes, bipartisan governance, and the realities of leading in the minority. Isaacsohn shares lessons from legislative negotiations, the importance of building relationships across the aisle, and why the most impactful decisions in public service are often the ones that prioritize doing good over simply feeling good. Takeaways Public Service Starts with Gratitude: Isaacsohn credits his upbringing to parents who emphasized that being born in the United States is a privilege. That perspective shaped his belief that public service is about paying that gift forward by improving communities and expanding opportunity. Doing Good Matters More Than Feeling Good: One of Isaacsohn’s defining leadership lessons is that policymakers often face a choice between symbolic victories and meaningful results. He shares how persistence and compromise helped deliver policy changes that provided free meals to thousands of Ohio students. Housing Requires Both Supply and Fair Markets: Ohio’s housing challenges reflect a complicated mix of limited supply, regulatory barriers, and market pressures. Isaacsohn explains that solving the housing crisis requires both increasing construction and ensuring that housing markets remain fair and competitive. Education Policy Has Generational Consequences: Decisions made in education policy can shape outcomes for decades. Isaacsohn warns that underinvestment in schools and lost learning time can create long-term setbacks that are difficult to reverse. Urban and Rural Communities Share the Same Struggles: Despite cultural differences, Isaacsohn believes many urban and Appalachian communities face remarkably similar challenges from healthcare access to economic opportunity. Bridging those communities, he argues, could unlock powerful solutions across the state. Chapters 00:00 Introduction and welcome 01:56 Ohio’s “secret sauce”: balance in opportunity and quality of life 03:40 Dani Isaacsohn’s upbringing and the values of service 06:17 Grassroots organizing and the path into politics 09:00 Becoming Minority Leader in the Ohio House 11:08 Strategic priorities for Ohio’s future 16:15 Understanding the complexity of the housing crisis 22:12 Housing supply and market competition 26:46 The “last chance” leadership questions 34:49 Doing good vs feeling good in public service 41:19 Why education policy shapes generations 45:13 Final reflections and optimism for Ohio’s future Keywords Dani Isaacsohn, Ohio House of Representatives, Ohio politics, housing policy, education policy, bipartisan leadership, public service, housing supply, urban rural divide, state government, civic leadership, Midwest politics, economic opportunity

    46 min
  8. Ep. 60 – The Next Generation of Public Service: The Jentry Future Leaders Panel

    MAR 10

    Ep. 60 – The Next Generation of Public Service: The Jentry Future Leaders Panel

    In this special episode of The Jentry Podcast, host Jonathan Mason shares the replay of the live Jentry Future Leaders Panel, a conversation designed to inspire the next generation of leaders to pursue careers in public service. The panel features Mayor Annette Blackwell of Maple Heights, Ohio, State Representative Christine Cockley of Ohio, and City Manager Rose Beverly of Paris, Texas. Together, they discuss their paths into leadership, the realities of governing at the local and state levels, and why young people should consider public service as a meaningful and impactful career. From city halls to state legislatures, the conversation explores how leadership develops, why representation matters, and how communities benefit when young people step forward to serve. The panelists share lessons from their own journeys and offer advice to aspiring leaders who want to make a difference in their communities. Takeaways Public Service Needs the Next Generation: Each panelist emphasizes that the future of communities depends on young people stepping into leadership roles. Cities and states need fresh perspectives, new energy, and leaders willing to solve complex problems. Representation Matters in Leadership: When leadership reflects the people it serves, communities are stronger. The panel highlights how representation builds trust, increases participation, and ensures policies reflect real community needs. Careers in Government Are Impactful: From managing cities to shaping state policy, public service offers the opportunity to directly improve people’s lives. The panelists share how their work influences housing, economic opportunity, and quality of life for thousands of residents. Leadership Is Built Through Service: None of the panelists began their careers expecting the exact roles they now hold. Their journeys demonstrate that leadership grows through community involvement, mentorship, and a willingness to step forward when opportunities arise. Young People Should Start Now: Getting involved early through internships, volunteering, or local civic engagement—can open doors to long-term leadership opportunities in government and community development. Chapters 00:00 Introduction to the Jentry Future Leaders Panel 01:06 Mayor Annette Blackwell introduces Maple Heights leadership journey 01:27 Representative Christine Cockley on engaging young leaders in public service 02:06 City Manager Rose Beverly on local government leadership 05:12 Why young people should pursue careers in public service 10:34 Representation and leadership in government 16:18 Career paths into local and state government 22:47 Mentorship and building leadership skills 28:41 Advice for the next generation of public servants 34:12 The future of leadership in communities 39:30 Closing reflections from the panel Keywords Jentry Future Leaders, public service careers, civic leadership, youth leadership, Mayor Annette Blackwell, Christine Cockley, Rose Beverly, local government careers, civic engagement, next generation leadership, city management, state government, community leadership

    1h 7m
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The Jentry Podcast highlights government leaders who are pioneering innovative solutions in jobs, affordable housing, childcare, workforce development, and local investment—transforming urban, suburban, and rural communities across America. A new generation is coming of age. Millennial and Gen Z community stakeholders and leaders are redefining civic engagement and community ownership. The New Jentry is not about displacement—it’s about ownership. It’s a generation committed to investing in and strengthening their communities for the long term. By demystifying local government, we’re making it more accessible ensuring that the next generation is informed, engaged, and empowered to shape the places they call home. We spotlight the changemakers shaping the future of our communities—and discover how each person can take action where they live. The Jentry Podcast is hosted by Jentry & Co. Founder, Jonathan Mason.

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