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

In this episode, Garrett sits down with David and Stephanie Bailey, co-founders of Nimble Retail, a Tampa-based company reimagining what retail space can look like. They share how their micro-shop model helps small businesses thrive in high-traffic areas without the need for traditional buildings or long-term leases. From forming creative partnerships with cities and landlords to solving permitting challenges and scaling their footprint across Florida and beyond, this conversation dives deep into how Nimble is making retail more flexible, affordable, and local. Whether you're in real estate, retail, or just love creative business models, this episode will get you thinking differently about space.

0:00:00 - Introduction

0:11:08 - Nimble Retail

1:12:19 - Car Reliance

1:16:21 - Retail in creative places

1:26:55 - Franklin Street Plan

In episode 141, Garrett sits down with Karen Kress, Director of Transportation and Planning at the Tampa Downtown Partnership, for a deep dive into how Tampa’s urban core is evolving. From expanding the Riverwalk and redesigning Bayshore Boulevard to making streets safer for bikes, e-scooters, and pedestrians, Karen shares the bold ideas and behind-the-scenes efforts shaping the city’s future. They explore why historic preservation matters, how parking policies can spark development, and what it will take to create a truly vibrant, connected downtown. Whether you care about transportation, public spaces, or Tampa’s growth, this conversation is packed with insights you won’t want to miss.

0:00:00 - Introduction

0:03:06 - Harbor Island People Mover

0:05:16 - Downtown Tampa in the 90’s

0:07:14 - Tampa Downtown Partnership

0:21:37 - Streetcar Extension

0:34:55 - North Downtown Vision Framework

0:52:35 - Parking Minimums 

1:09:15 - Franklin Street

1:20:09 - Dash Tampa

1:32:53 - South Downtown Vision

1:42:46 - Bike Transportation

1:52:56 - West River Walk

2:08:47 - Marion Transit Pkwy

2:22:44 - Yellow Brick Row

In episode 140, Garrett sits down with Harry Cohen, Hillsborough County Commissioner, for a candid conversation about Tampa Bay’s future. They unpack why the region’s explosive growth is outpacing infrastructure, how the collapse of the All for Transportation tax initiative set the area back a generation, and what it will take to build a transit system that actually works. From the political tug-of-war between urban and suburban priorities to the struggle over funding ferries, roads, and rail, Cohen offers an insider’s perspective on why big solutions keep slipping away and where hope still lies for progress. Whether you care about traffic, development, or the future of the city you call home, this discussion will give you plenty to think about.

0:00:00 - Introduction

0:14:22 - Hillsborough County Growth

0:28:32 - Why Transportation Initiatives Are Stalling

0:39:57 - Sunshine Law

0:47:34 - Transportation Continued

1:11:15 - Sports Stadiums

1:18:13 - Being a Politician

1:24:05 - Airport and Transportation

1:39:36 - Incorporation

In episode 139, Garrett sits down with Joe Citro for an unfiltered conversation about Tampa’s future and the forces shaping it. They unpack why affordable housing is nearly impossible without reliable public transit, explore the tension between regional collaboration and protecting Tampa’s voice, and share candid stories about the pressures facing city staff. From the decline of neighborhood trust to the debate over property taxes and the revival of streetcars, this episode connects past and present to imagine what it will take to build a healthier, more connected city. Whether you care about housing, transportation, or civic culture, you’ll find plenty to think about.

0:00:00 - Introduction

0:02:50 - Why Tampa is great

0:12:54 - Using the CSX railroad

0:20:51 - The future of transit in Tampa

0:46:12 - Parking Issues

0:53:51 - Hillsborough County Politics 

1:10:15 - Gasworx

1:29:31 - Ashley Drive Redevelopment 

1:43:00 - Ybor Harbor

2:00:11 - What would Joe change in Tampa?

2:16:38 - Insurance 

In episode 138, Garrett sits down with Donald Phillips, real estate developer and the founder of Woody’s Wash Shack, to unpack the life experiences that shaped him as a person and an entrepreneur. Donald opens up about losing his father in a plane crash at age 14, the lessons he learned watching his mother hold the family together, and the mindset he developed to never work for anyone else again. From building his first companies to launching Woody’s Wash Shack as a family-driven, community-oriented brand, this conversation is about more than business. It’s about values, identity, and building something meaningful that lasts. Whether you’re an entrepreneur, a parent, or just someone trying to find purpose, this one hits deep.

0:00:00 - Introduction 

0:18:38 - Why Start Woodies?

0:25:00 - Importance of Branding

0:39:36 - Confronting Opposition 

0:53:37 - Selfless Service 

1:07:46 - The Woodie Wagon

1:16:58 - Customer Experience 

1:39:33 - Hiring Employees 

In episode 137, Garrett sits down with Michael Joyce, the founder of Emoto Supply Co., to talk about the future of mobility in Tampa. From acquiring the U.S. assets of Swedish e-bike brand Cake to launching a new kind of retail hub for electric bikes and mopeds, Michael shares how Emoto is reshaping transportation in the city. They dive into Tampa’s bike infrastructure problems, the changing regulations, and what it will take to make alternative transit a real option in Florida’s car-centric culture. This is a conversation about innovation, risk, and what it means to bet on a better way to move.

0:00:00 - Introduction

0:15:03 - Bike Infrastructure

0:34:34 - Buying an E-Bike0:39:42 - Regulations

0:58:13 - Saving Time with an E-Bike

1:17:22 - Spoke Stories Podcast

In episode 136, Garrett sits down with Florida State Senator Jay Collins, a decorated U.S. Army Green Beret and Purple Heart recipient who served over two decades in Special Forces, including five years after losing his leg in combat. Jay shares the harrowing story of nearly dying in Afghanistan, the resilience that led him back to active duty, and how his experiences on the battlefield shaped his mission to serve in public office. From leading troops in war zones to leading legislative efforts in Florida, Jay discusses the values that drive him, the lessons learned through adversity, and why he believes real leadership means putting others first. This is a powerful conversation about courage, service, and the fight to make a difference at home.

0:00:00 - Introduction

0:05:49 - Losing your leg

0:18:17 - Operation BBQ Relief

0:23:44 - Becoming a politician

1:08:46 - Transportation

1:43:14 - Property Tax

In episode 135, Garrett sits down with Ron Weaver, a legend in Tampa’s legal and development world, to unpack his 50-year career in land use law. They discuss the evolution of Tampa’s skyline, the laws that shaped it, and the massive opportunities still ahead. From fast-tracked skyscrapers to missed chances at a Central Park-style green space, Ron shares insider stories and bold ideas for what Tampa needs next. They also explore how AI, public-private partnerships, and walkable urban design could define the city’s next chapter. This episode is a must-watch for anyone invested in Tampa’s growth.

0:00:00 - Introduction

0:04:45 - Gen Z

0:07:03 - U.S. Politics

0:08:44 - Ron Weaver Background

0:18:50 - Technology and Human Connection

0:32:35 - Tampa Land Use in the 80’s

0:38:20 - Land Use Law Today

0:43:35 - Regions Building

0:46:45 - Future Downtown Tampa Planning

0:50:33 - The Importance of City Owned Land

0:54:28 - How to build a vibrant urban core