Sep 4, 2025
By Florida Business Journals staff
Florida is in the midst of one of the largest intergenerational wealth transfers in the country, reshaping not only family legacies but also the financial services sector that supports them.
From established firms managing billions in assets to new ventures harnessing technology and innovation, the state’s wealth managers and financial leaders are redefining how capital is grown, protected and given back. Their expertise spans private wealth, philanthropy, fintech and multigenerational planning — reflecting both the complexity and opportunity in Florida’s evolving economy.
Meet the people shaping the future of finance across the Sunshine State in this year’s People to Know.
Marianela Collado
Co-owner and CEO, Tobias Financial Advisors
Years in the role: 8
Previous role: Principal, Bessemer Trust
Collado began her career in New York, working in wealth and tax advisory services, before joining Tobias Financial Advisors in Fort Lauderdale in 2015. Two year’s later, she became CEO, and one of her most impactful moves has been investing in team development by fostering a supportive, growth-focused culture. That approach has boosted retention and directly elevated the client experience, she said. Tobias helps high-net-worth clients, particularly business owners, navigate financial complexity with its tax-savvy, fully integrated approach. As a fee-only fiduciary, the firm provides conflict-free advice and works closely with clients’ attorneys and CPAs. Multigenerational planning is also a key focus, backed by a collaborative team structure and smart use of technology.
Donald Kress
CEO, Coral Gables Trust
Years in the role: 2
Previous role: Board director and member of the Executive Committee, Coral Gables Trust
Since taking the helm of Coral Gables Trust in 2023, Kress has led a period of strong growth, including an expansion of the firm’s Boca Raton office to meet rising demand in the high-net-worth market. By the end of 2024, Coral Gables Trust reported a 21% spike in assets under administration and management. The company focuses on trust, estate and investment services, and prides itself on offering fiduciary advice with no proprietary products. The firm also handles complex, often illiquid, assets that many competitors shy away from. To take its service a step further, Kress said, Coral Gables Trust recently brought in a consulting group to help identify ways to use artificial intelligence, aiming to improve efficiency while keeping its highly personal approach intact.
Jay Pelham
President, Kaufman Rossin Wealth and Kaufman Rossin Insurance Services
Years in the role: 7
Previous role: President, TotalBank
Jay Pelham joined Miami-based Kaufman Rossin Group in 2018, and a year later led the launch of Kaufman Rossin Wealth. A former bank executive with nearly 30 years of experience in the financial services industry, Pelham helped shape the firm’s approach to serving high-net-worth clients by emphasizing alternative investments, particularly private credit. He said Kaufman Rossin Wealth benefits from KR’s long-standing reputation in tax, estate and advisory services, offering clients a comprehensive suite that includes financial planning, investment strategy and insurance solutions. The firm focuses on clients experiencing major life events, such as business sales or inheritances, where its integrated services can add value. Advisers also use advanced software and reporting tools to streamline tax planning, monitor performance and provide clients with a consolidated view of their finances.
Annie DeStefano
Founder of Ann DeStefano Advisory
Time in role: Less than one year
Previous role: FIS Vice President of Strategic Partnerships
With the backing of a 12-year-long career in banking and finance, DeStefano is operating at the cutting edge of wealth management with her consulting group. Especially in a rapidly digitizing world, DeStefano aims to assist financial technology companies in how to handle their digital assets. “There’s just a whole different kind of calculus that these personas need to think about in the world of finance,” she said. The launch of DeStefano’s company aligns with broader city-wide efforts to double down on Jacksonville gradually becoming a hub for financial services, including companies like FIS.
Daniel Gilham
Managing Director of Farther
Time in role: 4 years
Previous role: VP and PIM Portfolio Manager of Wells Fargo Advisors
Gilham leads a national team focused on bringing business owners and institutions comprehensive, objective financial advice with Farther — a venture-backed wealthtech firm — from where he’s based on the First Coast. He worked as a systems engineer and product manager at AOL through the tech crunch of the late 90’s and early 2000’s. That early experience drove Gilham to take a more objective approach to financial planning, inspired his doctoral research and brought him to Farther. The organization operates at the intersection of technology innovation and generational wealth transition, he said: “By combining intelligent technology with expert advice, we give our advisors the tools to deliver truly comprehensive, objective guidance — without sacrificing time with clients.”
Isaiah Oliver
President of the Community Foundation of Northeast Florida
Time in role: 2 years
Previous role: President and CEO of the Community Foundation of Greater Flint
Working with some of the region’s wealthiest families and businesses, including 1,200 grantees in 2024, Oliver is uniquely positioned to follow the ongoing wealth transfer. The Community Foundation is home to more than 740 unique funds with more than
$700 million in assets. The organization represents a trusted relationship partner in the local philanthropic scene. For the past 25 years, the foundation has been focused on honing the next generation of donors. “The next generation of donors that have been innovative around creating financial opportunities for them and their families — they’re the ones that are actively engaged in giving real time, and so we’re both watching the transfer of wealth,” Oliver said. “But we’re also watching new wealth be developed in our community.”
Dale Crossley
Private wealth adviser, CrossleyShear Wealth Management
Years in the role: 27
Previous role: Financial planner, CrossleyShear
With offices from Heathrow to Merritt Island, Dale Crossley has provided wealth management services for over a quarter of a century with his colleague Evan Shear. Their team manages assets for families, executives, small busineses and even professional athletes. His entrepreneurial spirit attracted Crossley to wealth management, with entrepreneurship being something he sees is becoming more desired in heirs, but he finds they want the title without an understanding of the risk and fundamentals. In a world of meme stocks and other volatile assets, Crossley is interested in educating heirs early on in the financial planning process and building behavioral finance.
John and Brad Ledford
Titles: Founder/CEO; financial adviser, Fortress Wealth Group
Years in the role: Five
Previous roles: Financial adviser, managing director; financial adviser, Ameriprise Financial Services
This father-son duo’s firm manages hundreds of millions of dollars in assets, with a focus on business owners, retirees and high-net worth families. John Ledford had a real transformation in his life in 2016 when he survived a plane crash, reshaping his perspective about his work. They both work on multigenerational planning for clients and in the family. The firm releases economic reports quarterly that show consideration of the global economy in their planning, including geopolitical events, supply-chain issues and interest rates – an increasingly important strategy as uncertainty measurably impacts the intergenerational exchange due to market volatility.
Kevin Taylor
Title: Director and senior wealth adviser, Mariner Wealth Advisors
Years in the role: Four
Previous role: Principal, Vaughn Wealth
Sixth-generation Floridian Kevin Taylor has extensive experience on estate and asset protection planning for clients and families with a high net worth. As Florida continues to get older, there is an increasing need to focus on laws related to wealth management such as when retirees can start and stop making payments toward certain investments like IRAs. Taylor is looking into the Big Beautiful Bill, signed into law by President Trump in mid-2025, for the affects on the transfer and management of wealth. On top of the 225 clients and $600 million assets under management, Taylor’s ability to educate the community on changes to tax law and his experience with the Central Florida community make him a person to watch.
Tina Pepin
Executive Director, The Pepin Family Foundation
Years in role: 4
As Pepin guiding her family’s vast fortune into philanthropy, she aims to collaborate with other second- and third-generation Tampanians to boost local giving. Pepin is the daughter of Tampa alcohol magnate and former Pepin Distributing CEO Tom Pepin, who is among a growing number of local entrepreneurs to sell businesses that saw monumental success alongside the growth of the Tampa Bay region. She is defining the model of how next generations can use inherited wealth to reshape their family’s legacy. Pepin launched a family office earlier this year to grow the $350 million sum from the sale of Pepin Distributing in 2021, which will fuel the various philanthropic endeavors of the Pepin Family Foundation, from education to health care and law enforcement.
Shirl Penney
Founder, president and CEO, Dynasty Financial Partners
Years in role: 15
Previous role: Citigroup, director of executive financial services
Penney, a Wall Street veteran, is building a powerhouse platform for independent wealth advisers that is reshaping the business of money management. He has quickly ingrained himself in the who’s who of Tampa Bay’s financial circles since relocating the firm to St. Petersburg from New York five years ago. His network of ultra-high-net- worth clients is building Dynasty’s profile — and St. Pete’s — on a national stage. Dynasty has surpassed more than $115 billion in assets on its platform, inching closer to Penney’s $1 trillion goal in the next decade. Fifty-seven wealth management firms have transitioned to Dynasty’s network, representing a sum of wealth that spans prof essional athletes, female entrepreneurs and millennial clients.
Paul Shoukry
President and CEO, Raymond James Financial
Years in role: ~1
Previous role: CFO, Raymond James Financial
Shoukry leads one of Tampa Bay’s most iconic institutions and a giant in the wealth management industry. Raymond James’ private client platform spans more than 8,800 financial advisers and nearly $1.6 trillion in assets under administration. In one of his first acts after being appointed CEO earlier this year, Shoukry established a new C-suite role of chief artificial intelligence officer. The firm is pouring millions into investments in technology to build new tools for market analysis and client engagement on its wealth management platform. New applications are designed in collaboration with a technology advisory council of experienced financial advisers, ensuring the six-decade- old firm stays relevant as younger clients and advisers demand greater technological sophistication.
