In episode 152, Garrett sits down with Tampa City Council District 5 candidates Naya Young and Thomas Scott for a special election debate ahead of the October 28 runoff election. They tackle the biggest issues shaping District 5 and Tampa as a whole, including affordable housing, gentrification, diversity across neighborhoods, the importance of four votes on City Council for approval, and historic preservation. Whether you live in East Tampa, Sulphur Springs, Channel District, or Water Street, this conversation breaks down what’s at stake and how each candidate plans to address the future of Tampa.

0:00:00 - Introduction

0:03:09 - Affordable Housing

0:07:15 - Candidates

0:11:56 - Affordable Housing Continued

0:19:30 - Gentrification

0:43:31 - Diversity of District

51:24:10 - 4 Votes for Approval

1:34:18 - Historic Preservation

In episode 151, Garrett sits down with Walt Chancey of Chancey Architecture and Interior Design to explore the evolution of senior living from traditional nursing homes to lifestyle-driven communities that feel more like resorts. They discuss the demand surge known as the “Silver Tsunami,” the challenges of zoning and financing, and why Florida is at the center of this transformation. From pickleball courts and restaurants to affordable housing models, Walt explains how developers can meet the needs of an aging population while creating vibrant, multi-generational communities.

0:00:00 - Introduction

0:02:24 - New Era of Senior Living

0:11:39 - Demand

0:21:06 - Underwriting

0:38:13 - Water Color Place

0:44:47 - Urban and Suburban Growth

0:50:07 - Senior Housing Incentives

1:05:32 - Urban Neighbors

Episode 150 of the TBD POD dives into Tampa’s recent issues: the City Council’s $6 million streetcar expansion study, the debate over parking minimums in Ybor, and how micro retail like Casa Azul shapes small business success. Garrett and David break down the city’s $1.9 billion budget and cover the high-stakes District 5 special election. They also explore how social media is reshaping politics, why Tampa is now the least affordable city in Florida, and what national housing trends could mean for the city’s future.

0:00:00 - Streetcar Extension

0:01:56 - Casa Azul

0:05:35 - Streetcar Extension PT.2

0:10:54 - Parking Minimums

0:33:07 - City of Tampa Budget

0:46:21 - District 5 Special Election

0:59:03 - Zohran Mamdani

1:09:24 - Least Affordable City Article

1:10:03 - Political Priorities 

In episode 149, Garrett sits down with Greg Holland, President and CEO of the Straz Center, to unpack the $100M Boundless Campaign reshaping Tampa’s Riverwalk arts district. They cover the Veil canopy, a rooftop bar, two new restaurants, a donor club, and a 30% expansion of education spaces with new studios and rehearsal rooms. Greg explains how outdoor stages and free performances will activate the campus and how funding and community support are driving the vision, while also sharing why live performance is surging in Tampa, what the fall 2027 target means for the rollout, and how Opera Tampa, veterans and arts-in-healing programs, and future plans like a public boat dock fit into the bigger picture.

In this episode, Garrett sits down with Johnny Wong, Executive Director of the Hillsborough Transportation Planning Organization, to break down Tampa Bay’s future. They cover why public demand for rail keeps colliding with political realities, the $29 billion funding gap in Hillsborough’s long-range plan, how suburban sprawl drives congestion, and what projects like the TECO Streetcar extension, Brightline, and airport-to-downtown transit could mean for the region. From smart traffic signals to bold ideas like highway removals, this conversation explores the tough choices that will shape Tampa’s next 25 years.

00:00:00 - Introduction

00:05:00 - Autonomous Vehicles

00:15:00 - Urban vs. Suburban

00:20:00 - Job Centers

00:25:00 - Cultural Shift

00:39:30 - Access 2050 Plan

00:47:00 - State and Federal Funding

00:53:00 - Individual Priorities and Lifestyles

01:09:24 - A grant to improve public engagement

01:17:18 - TECO Streetcar

01:28:34 - The Regional Infrastructure Accelerator Grant

In episode 147, Garrett sits down with Max Herman to explore how Tampa became a cigar-fueled boomtown that drew immigrants from Cuba, Spain, Sicily, Germany, and Romania. From Henry Plant’s grand hotel to Vicente Ybor’s vision, they trace how prosperity, culture, and politics converged in Ybor City, where Jose Martí rallied support for Cuban independence and Paulina Pedroso became a symbol of solidarity. The discussion covers the rise of cigar workers as America’s first immigrant middle class, food traditions like the Cuban sandwich and deviled crab, the artistry of cigar labels, and how highways and urban renewal reshaped neighborhoods. This conversation reveals the stories that still define Tampa’s identity today.

0:00:00 - Tampa Bay Hotel

0:09:16 - The Big Guava

0:12:49 - Seal of City of Tampa

0:15:16 - Plant vs. Flagler

0:17:55 - Vicente Martinez Ybor

0:23:37 - Ybor History

0:30:57 - Cigars

0:37:55 - Historical Ybor Lifestyle

0:45:36 - Cigars Continued

0:47:27 - Historical Figures

1:01:27 - JC Newman Development

1:05:00 - Germans in Ybor

1:08:10 - Romanian Jews in Ybor

1:10:27 - Chinese in Ybor

1:13:17 - Who started the Cuban sandwich?

1:14:57 - New Tampa Residents

1:23:27 - Ybor History Tours

In episode 146, Garrett sits down with Christine Acosta, founder of Pedal Power Promoters and co-founder of Walk Bike Tampa, to discuss the future of biking, walking, and safe mobility in Tampa. Christine shares how affordability, infrastructure, and design all intersect when it comes to transportation, why slowing down vehicle speeds matters, and how projects like Bayshore Boulevard and the Green Spine show both the promise and pitfalls of Tampa’s approach. From lessons learned abroad to the local fight for safer streets, this conversation breaks down what it will take to build a city that works for everyone, not just cars.

0:00:00 - Introduction

0:05:23 - Biking in Tampa

0:15:30 - Cultural Shift

0:20:19 - Flexible transportation

0:25:05 - Pedestrians and Cyclists

0:38:17 - Budgeting for new projects

0:47:17 - SeeClickFix

0:57:33 - Urbanism

1:02:40 - Desire Paths

1:12:40 - Less Car Parking

1:17:18 - The Street Car

1:23:31 - The "Green Artery" and "Green Spine"

On episode 145, Garrett sits down with Joshua Pardue, whose team is leading the retail curation for Gasworx, one of the most ambitious redevelopment projects in Tampa. With $182 million in construction funding secured and thousands of new residents moving in, national and boutique retailers are now seriously considering Ybor for the first time in years. Joshua shares how his team is shaping the district’s future while keeping it authentic to its history and building a walkable, design-forward neighborhood that feels genuine, not corporate.

0:00:00 - Introduction

0:06:31 - Gasworx Renderings

0:11:30 - Other Development Styles

0:17:00 - Retail Curation for Gasworx

0:32:27 - Out of State Tenants

0:40:09 - The Future of Ybor

0:46:56 - Rise of Demand for Tampa

0:53:40 - Vision for Gasworx

0:59:31 - Block E2 Leasing

1:14:47 - La Union and Block W2

1:16:33 - Block E1 Leasing

1:24:41 - Chipotle coming to Water Street

1:30:07 - Planning Development 100 Years Out

1:36:47 - Block E3 Leasing

1:54:49 - Update on Garrett’s Development Project

In this episode, Garrett sits down with Kevin Johnson and Dontavoius Pittman, two of the three co-founders of Shacres, an innovative Tampa-based development firm building beautiful, affordable housing. From high school architecture classes to working across urban planning, construction, and city government, Kevin and Dontavoius share their journey back to Tampa and how it led to launching Shacres. They break down the challenges of getting their first projects off the ground, what they learned working with the city and federal government, and how thoughtful design can still be affordable. If you care about housing, community, or building something real in your city, this one’s for you.

0:00:00 - Introduction

0:38:00 - Shacres Development

0:45:19 - Young People in Development

0:55:46 - 10 Unit Multi Family in Ybor

1:10:03 - Real Estate Constraints

1:45:53 - Casa Maceo

Andrew Wright, founder of Franklin Street, founder of Ally Capital Group, and co-founder of Next Level Brands, joins the podcast for a deep dive into building multiple successful businesses. From navigating the 2008 collapse with a newborn and major financial pressure to leading a $7 billion real estate firm, Andrew shares what it really takes to scale, pivot, and lead with purpose. He opens up about culture, crisis leadership, burnout, and why stepping away from his own company helped him realize what truly matters. Whether you're building a team or starting from zero, this conversation is a masterclass in perseverance, self-awareness, and sustainable growth.

0:00:00 - Introduction

0:10:54 - Starting Franklin Street

0:33:54 - The Importance of Company Culture

0:49:41 - Ally Capital

0:59:20 - The Sundial St. Pete

1:07:29 - Work/Life Balance

1:16:48 - Westshore

1:32:00 - Next Level Brands