☕ Lattes with a Lawyer – March 2025 Recap
Date: March 27, 2025
Hosted by: The Law Firm of Douglas G. Jackson, P.A.
What Is Lattes with a Lawyer?
Lattes with a Lawyer is a monthly roundtable hosted by The Law Firm of Douglas G. Jackson, P.A., bringing together local leaders, business owners, and St. Petersburg residents. The series is designed to facilitate honest, solution-driven conversations around pressing local issues — building connection, courage, and actionable change through community dialogue.
Round 1: The Biggest Problems Facing Our Community
The session began with participants voicing the most pressing challenges they see in the St. Petersburg area today.
🔍 Key Themes Identified:
Market Instability: Business owners and residents are facing a lack of economic predictability, making long-term planning extremely difficult.
Lack of Central Communication: There’s no unified hub for residents or organizations to share important local information.
Cultural Disconnect: New developments often lack authentic ties to the St. Pete community, especially when led by outside interests.
Leadership Absence: Many attendees felt that local leadership is not deeply rooted in community life, creating a trust gap.
💬 Notable Quotes:
“Why aren’t we all on the same page as a community?”
“Where is the one place in St. Pete that shows all the organizations? There isn’t one.”
“Developers and realtors don’t introduce new people to the real community here — unless they live here themselves.”
“Leadership isn’t connected — they just aren’t involved.”
Round 2: Navigating Uncertainty & the Fear Around DEI
As the conversation deepened, the group explored the rise of uncertainty — not just economically, but culturally — especially around Diversity, Equity, and Inclusion (DEI).
🔍 Key Themes Identified:
Regulatory Red Tape: Permitting delays and unclear regulations are slowing progress for both residents and small businesses.
Economic Unrest: Tariffs and policy shifts are discouraging local investment.
Backlash Against DEI: Minority-owned businesses expressed fear that openly participating in DEI initiatives may invite political or social retaliation.
Fear-Based Silence: Many underrepresented business owners are rebranding or hiding parts of their identity just to avoid negative attention.
💬 Notable Quotes:
“Minorities aren’t even submitting for RFPs anymore — because they don’t think they’ll get approved. Especially if they’ve been outspoken.”
“Will people have to get back in the closet and rebrand just to feel safe?”
Reframing DEI as a Freedom Movement
Despite these concerns, the group collectively reframed DEI as something much larger than a corporate checkbox — it’s about freedom.
Freedom to own a business as your authentic self.
Freedom to express your identity without fear.
Freedom to feel like you belong in your own city.
🔑 Key Insight:
“DEI needs a new narrative. This is about the freedom to be who you are. The courage to show up fully. That’s not political — that’s human.”
The group emphasized that now is not the time to retreat in fear, but to lead with courage.
Round 3: The Future of the Rays & the Gas Plant Redevelopment
The final topic of discussion turned toward the future of the Tampa Bay Rays, Tropicana Field, and the Gas Plant District — and the community’s role in shaping what comes next.
🔍 Key Themes Identified:
Uncertainty Fatigue: Years of planning and replanning have left residents exhausted and cynical.
Desire for a Cultural Anchor: Whether or not the Rays stay, the city needs an anchor that reflects its identity.
Redefining Major League Identity: Some questioned whether being a “Major League City” means chasing big deals or prioritizing culture and creators.
Holistic Development Needed: Attendees called for integrated planning — transportation, housing, education, and preservation of Black history should all be part of the conversation.
💬 Notable Quotes:
“We are starting over — again. And we are tired.”
“Maybe we aren’t a Major League City — maybe we’re a Minor League City. Minor League is cooler anyway.”
“We need to be the people in the discussion.”
“We don’t want piecemeal construction — we need a system.”
Final Takeaways from This Session
🔑 What This Community Conversation Made Clear:
Uncertainty is the enemy of progress, and it’s as much emotional as it is financial.
DEI is not division — it’s the freedom to be visible and real.
True engagement must be built into the system, not treated as a PR checkbox.
St. Pete’s identity is being rewritten, and the people who already live here must hold the pen.
Closing Thought:
“People need to know who is on their side. And sometimes the most radical thing you can do is simply show up — fully, visibly, courageously — as yourself.”
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