Kyle Cain serves as Chief Investment Officer of Freedom Family Office, where he leads the firm’s investment research, asset allocation, portfolio construction, security and manager selection, trading, rebalancing, tax-aware implementation, and risk management. He works closely with the advisory and tax teams to ensure investment decisions are designed around each family’s broader financial plan, tax position, liquidity needs, and long-term objectives.
Kyle began his financial career as a trader with Fidelity Investments in 2007, just before the Global Financial Crisis. That experience reinforced a principle that continues to shape his investment philosophy today: a portfolio should not be managed in isolation from the financial plan it is meant to support. Over the course of his career, Kyle has advised hundreds of clients and has been responsible for managing more than half a billion dollars in client assets.
Prior to joining Freedom Family Office, Kyle spent several years with J.P. Morgan serving ultra-high-net-worth clients in Palm Beach. His experience across trading, portfolio management, and private wealth management gives him a perspective that combines institutional investment discipline with the highly individualized needs of affluent families.
Kyle holds the CERTIFIED FINANCIAL PLANNER™ certification, the Certified Investment Management Analyst® certification, and the Accredited Portfolio Management Advisor™ designation. He is also a published author and former adjunct professor teaching financial planning.
Outside of work, Kyle enjoys spending time with his two children, fitness, reading, and following University of Florida football.
With over 25 years of experience in wealth management, Peter is responsible for building a custom wealth plan for each client. He begins with a detailed review of their current asset allocation, fees and performance, which culminates in a tailored strategy that realizes their goals and values. With experience in estate planning and facilitating family meetings, his presence among our firm is appreciated by all who work with him.
After graduating from Yale University and the University of Connecticut School of Law, Peter practiced law in New York City and Connecticut for 12 years. His law practice led him into the wealth management field, where he represented trust companies and other financial institutions. He then served as Co-Founder and President of Sachem Trust, located in Greenwich, CT and later as President of State Street Bank and Trust Company of CT. For 14 years, he served as Senior Wealth Director at BNY Mellon in New York City.
Peter’s passion is working directly with individuals and families to reach their personal and financial goals. He offers his clients deep experience in all facets of wealth management: financial and estate planning, investments and insurance, family dynamics and wealth transfer. To this technical expertise, he adds the ability to see the big picture and to integrate all the components into a cohesive plan. To both clients and other advisors, Peter is known as optimistic, an excellent listener and extremely responsive. Peter is an active member on our investment committee.
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Sameer leverages his passion for mentorship, education, and client engagement to drive strategic growth at Freedom Family Office. His journey began with the realization of the importance of asking pertinent questions, listening, and delving deeper into understanding prospects and clients while hosting a prominent mentorship podcast. Through his podcast, "The More We Know," Sameer has had the privilege of interviewing esteemed individuals such as the founder of Reebok, the former CO-CEO of Chipotle, the former CEO of P.F. Chang's, and the Mayor of Miami. This commitment to mentorship laid the groundwork for Sameer's career, emphasizing the creation of exceptional client experiences and his role in spearheading go-to-market strategies. Sameer has a passion for truly understanding each client's challenges in efforts to identify the ultimate solution for them and help cultivate being part of building a world class culture at Freedom Family Office. Sameer is an active member on our investment committee. Sameer is also responsible for helping evaluate and implement new technology to enhance our reporting, client experience, and overall firm efficiency.
Before assuming his current role at Freedom Family Office, Sameer served as a Vice President, Investor Relations at Chicago Atlantic, a $1.2 billion alternative investment manager headquartered in Chicago and Miami. In this capacity, he collaborated closely with RIAs, family offices, and high-net-worth individuals. His professional journey commenced at UPM, a publicly traded European company, where he began as the first US-based sales trainee. Later, Sameer transitioned to Enfusion, a fintech company catering to hedge funds. Sameer was able to be a part of a growing business development team that saw Enfusion go from high growth startup to IPO. He then went on to become a regional director at Vise, helping manage roughly $500 million in AUM. Here, he focused on managing existing relationships with advisors, adding more AUM, and bringing new RIAs on the platform. Sameer worked closely with client services, investment team, product/ engineering team, and leadership to provide an exceptional experience for clients and help contribute to the long-term growth of the firm and its technology.
Sameer holds a bachelor’s degree in business management from Loyola University Chicago and has completed coursework at the University of Chicago Booth School of Business. Continuously pursuing further education, he has engaged in leadership and fellowship programs, including a fellowship with Transform VC, an early-stage venture capital firm based in San Francisco. Transform VC specializes in investing in deep tech, aiming to revolutionize traditional industries. During his tenure with Transform VC, Sameer conducted founder interviews, assessed investment opportunities, and deepened his passion for entrepreneurship and supporting innovators. Outside of work, Sameer loves spending time with his family, playing basketball, and pursuing his passion for fitness. He's shed over 100 pounds and is currently working on hitting his final target weight goal.
Anthony Culotta brings more than 32 years of seasoned experience in the financial services industry to his role as a Wealth Advisor at Freedom Family Office. Before joining Freedom, he built his career at several respected firms, including Charles Schwab, and most recently served clients at Baird. He is a CERTIFIED FINANCIAL PLANNER™ professional and holds FINRA Series 7, 63, 65, 9, and 10 licenses, reflecting his deep commitment to professional excellence and fiduciary‑minded guidance.
Anthony’s work is driven by a deep interest in investment management and holistic financial planning. He partners with clients to design intentional strategies that reflect their goals, values, and long‑term vision. His approach blends thorough analysis with an understanding of each client’s distinct circumstances, helping them make well‑grounded choices throughout life.
He believes meaningful financial planning goes beyond numbers. For Anthony, it’s rooted in reliability, openness, and steadfast guidance. He takes pride in being a consistent partner and advocate as clients’ lives and priorities evolve.
On a personal note, Anthony is a proud stepfather and is married to his wife, Stacy. A devoted dog enthusiast, he’s rarely without his four‑legged companions. A lifelong sports fan and self‑professed baseball geek who loves the analytical side of the game, he also enjoys movies, travel, spirited conversations about life’s big questions, and the occasional pursuit of boredom.
Jenna has dedicated her entire career to going above and beyond for clients and creating exceptional experiences for them. She is Freedom’s Chief Experience Officer (CxO) and a licensed Wealth Advisor. Jenna gets a thrill creating exciting and memorable experiences for Freedom’s diverse clientele as she helps them achieve their own version of success.
Prior to Freedom, Jenna worked at Goldman Sachs where she helped manage over $500 million in AUM. Before that, she led the 19-person frontline team of Customer Experience Associates at the largest hedge fund in the world, Bridgewater Associates, with over $140 billion in AUM.
After graduating with a B.A. from Quinnipiac University, Jenna began her business career at the Greater New Haven Chamber of Commerce, where she led Membership Services and served as the Executive Director of the young professional's organization, serving over 2,000 members spread across the south-central Connecticut region.
Jenna spent 15 years training as a competitive figure skater and traveling internationally, where she learned key values such as determination, perseverance, and flexibility in the face of adversity. As she leveraged her skating career into a successful coaching business, she developed a passion for both deeply understanding people and figuring out how to motivate them to achieve greatness.
Stacy Culotta brings over 22 years of experience in the financial services industry to her role as a Wealth Advisor at Freedom Family Office. Known for delivering white-glove, concierge-level service, Stacy is deeply committed to building lasting relationships and guiding clients through every stage of their financial journey with care, clarity, and compassion.
Stacy holds a Master’s degree in Personal Financial Planning, is a CERTIFIED FINANCIAL PLANNER™ professional, and earned a graduate certificate in Financial Counseling. She has extensive experience across all aspects of wealth planning, including investment planning, retirement planning, and tax planning—with a specialization in estate planning. Her approach is both comprehensive and highly personalized, helping clients align their wealth with their values and long-term goals. Stacy is an active member on our investment committee.
Stacy’s passion for estate planning is deeply personal. Years ago, she was named Healthcare Power of Attorney for her terminally ill father—a role she wasn’t emotionally prepared for. The absence of a clear estate plan placed an immense burden on her during an already heartbreaking time. That experience sparked her commitment to ensuring her clients have the right plans—and the right people—in place, so their loved ones are never left unprepared.
Outside of work, Stacy is a proud wife and mom to a married son and an adult daughter. She shares her home with three beloved dogs and is a self-proclaimed dog lover. She enjoys Barre classes to stay active, cherishes a great cup of coffee, and finds joy in spending quality time with her husband, family, and close friends.
Ron Rosenfarb is the Founder and Chief Operating Officer for Freedom Internet Group, Inc. (FIGI) and Freedom adVentures, Inc., which provides services to Freedom's portfolio of companies. He is responsible for all operations, including managing and coordinating daily activities of our teams. Ron is an active member on our investment committee.
Prior to partnering with his brother Noah, Ron was a partner at the Rosenfarb Law Firm and also worked at Rosenfarb LLC, a forensic accounting firm founded by his father, Sam. Ron specialized in case strategy, research, and legal consultation. He worked with clients to address complex litigation issues in the areas of business, forensic accounting, fraud assessment, expert testimony, due diligence, and business valuation. He is the author of the book Winning with Financial Damages Experts: A Guide for Litigators.
After graduating from Syracuse University and Rutgers School of Law, he passed both the State of New York and the State of New Jersey Bar Examinations. However, Ron pursued a career in independent film. He produced an award winning feature film which was seen and applauded in film festivals throughout the United States, Mexico, and South America.
After his career as an independent film producer, Mr. Rosenfarb spent nearly a decade working as assistant corporation counsel and ran operations for a marketing and communication firm in downtown New York City. While there, Ron negotiated contract terms with top name musicians, comedians, and professional athletes, who would be presenters, speakers, and entertainers for his clients.