Sidney Calloway, Managing Partner of the Fort Lauderdale office & Co-Chair of the Government Law Practice Group, Shutts & Bowen LLP

May 2026 — Invest: spoke with Sidney Calloway, managing partner of the Fort Lauderdale office for Shutts & Bowen LLP, about how AI is reshaping legal practice and how Florida’s land use changes are influencing development. “Regulatory change is rarely static in Florida, so developers and investors will continue to watch how state policy, local implementation, and court guidance evolve, especially around housing, infrastructure procurement, and emerging tech,” Calloway said.

How has the Florida legal and regulatory environment changed over the past year, and how is it influencing business confidence and investment across South Florida?

One of the biggest shifts has been the legal industry’s rapid adoption of AI across practice areas. Law firms are getting more comfortable with the use of AI platforms. At the same time, the profession is working through how that use aligns with the rules and expectations that govern lawyers in Florida.

The conversation quickly moves past efficiency and into responsibility. Firms are building safeguards around confidentiality, accuracy, and fairness, and they are thinking through how AI-generated outputs fit within Florida Bar rules and courtroom practices. Early hesitation was often tied to those guardrails, particularly when lawyers were unsure how to protect privileged information, verify outputs, and avoid over-reliance on tools that can hallucinate or reflect bias. The pace has picked up as firms develop clearer standards for responsible use, including internal policies on what can be uploaded, how results are validated, and how AI use is supervised like any other work product.

How are issues like land use, zoning, and permitting impacting your clients, and how are you helping them navigate the intersection of development and legal expertise?

Two factors are shaping the environment. First, state action aimed at housing affordability has changed the development playbook. The Live Local Act, in particular, has become a meaningful tool for projects that include affordable housing. It can reduce the time and cost associated with local entitlements that, historically, required significant capital and patience to navigate.

As a result, developers are placing more emphasis on projects that can move forward under that framework, including mixed-use concepts and conversions of commercial or industrial sites. Our role is to help clients understand what the law allows, where local processes still matter, and how to structure projects to minimize risk while staying on schedule.

Second, we are also seeing stronger activity beyond housing. Since the second and third quarters of last year, work has been more robust across South Florida, including office development and continued momentum in the condominium market.

How are public-private partnerships penciling out as capital markets fluctuate and underwriting standards tighten, and how is your firm helping clients manage risk?

Public-private partnerships continue to be a practical way to advance infrastructure and development priorities, especially at the local level. We see them most clearly around public infrastructure, from roads and bridges to public facilities, and in more specialized contexts tied to ports and airports.

In Broward County, the focus is connectivity and competitiveness: moving people efficiently while also supporting the movement of goods and services that drive import, export, and regional growth. Marine-related opportunities are also rising, and that growth will require coordinated infrastructure investment, from waterfront access and freight movement to resilience planning that protects assets over time. We also see more partnership conversations tied to the workforce, including pathways for high-school students who want to enter the job market directly. Aligning education, training, and employer needs is becoming part of the regional competitiveness equation.

As underwriting tightens, the legal work becomes more sensitive to allocation of risk, timelines, performance requirements, and regulatory compliance. We help clients structure agreements that align incentives between public and private partners and anticipate friction points before they slow a project down.

In what ways are infrastructure planning and transportation funding decisions influencing development strategy and regional competitiveness?

The port and the airport are central to the region’s long-term strategy. The airport’s growth over the last decade reflects planning decisions made many years earlier, and that is the lesson for today’s infrastructure choices: capacity and connectivity have to be built ahead of demand.

Florida’s population growth remains a major pressure point. That means infrastructure must support quality of life and workforce access, while also ensuring industries can move products, goods, and services. The encouraging part is the level of coordination. County leadership, business groups, port stakeholders, and tourism interests are increasingly aligned in planning and resource decisions.

How is Shutts & Bowen positioning itself to serve as a strategic business adviser while also delivering complex litigation and regulatory counsel in a rapidly changing market?

A core part of the firm’s identity is community engagement and market knowledge. We are a statewide firm, and that presence helps us understand how local needs connect to state-level processes and regulatory realities. That perspective matters when clients are moving projects through approvals, negotiating with public entities, or navigating complex transactions.

We also emphasize practical problem-solving. Clients want counsel that can anticipate where a process will stall and help them keep momentum. That combination of regulatory experience and real familiarity with Florida markets is a key reason we can operate as both legal counsel and business adviser.

From a talent perspective, how are you balancing lateral growth with the development and retention of attorneys?

Quality of life has become a major driver in recruiting and retention, particularly for younger partners and associates building families and community ties. We offer lateral attorneys a platform to grow business, supported by collaboration across the firm and strong internal resources.

Retention also depends on communication. Younger lawyers have pushed firms to listen more closely and communicate more clearly, and that feedback is valuable. When attorneys feel supported, trained, and heard, it strengthens long-term commitment and, ultimately, client service.

Which industries are driving the most legal activity for your firm, and how do you see that mix evolving?

The mix is dynamic because we are a full-service firm. Real estate remains a cornerstone, and we continue to see strong activity in financial transactions, creditors’ rights, and bankruptcy, along with commercial work that supports business growth. Litigation remains steady because disputes are an inevitable part of business activity.

We also see opportunities in niche areas that reflect Florida’s changing demographics and economy, including probate and estates as population patterns shift, and maritime-related work as the marine industry expands alongside tourism.

Looking ahead three to five years, how do you expect legal and regulatory trends to influence investment, infrastructure, and economic development in the region?

AI will keep reshaping expectations around cost, speed, and value. Firms will need to deliver more focused, sophisticated counsel efficiently, while also demonstrating why judgment and experience still matter when risk is high. Regulatory change is rarely static in Florida, so developers and investors will continue to watch how state policy, local implementation, and court guidance evolve, especially around housing, infrastructure procurement, and emerging tech.

Businesses are already using AI internally for certain tasks, so outside counsel will have to be proficient with the technology and clear about the value proposition. Over time, the firms that combine responsible AI use, strong talent, and practical solutions will be best positioned to support investment decisions, infrastructure projects, and continued economic development across South Florida.