Academy Team

Richard Orlando, Founder & Instructor

For the past twenty-five years, Dr. Orlando has sat at boardroom tables and kitchen tables alike, advising high and ultra-high net worth client-families—many at the helm of a family enterprise—as well as training thousands of advisors to build upon financial advising to include the qualitative, multigenerational planning needs of their client-families.

Prior to founding Legacy Capitals, Dr. Orlando led Merrill Lynch’s Global Practice Management Consulting Group for fifteen years and served in Merrill’s Family Office. He has been referenced in numerous publications, including The New York Times, Bloomberg Business, and The Wall Street Journal online, among others.

His interdisciplinary background includes computer science, business, and psychology. After earning a Bachelor of Science in computer science and business from St. John’s University, he pursued a career on Wall Street, earning his Series 7 and 63 licenses. Returning to school, he received a master’s degree in counseling/theology from Trinity International University, then a doctorate in family systems from Seton Hall University with a dissertation on wealth management family teams.

Dr. Orlando is an approved instructor for IMCA’s Certified Private Wealth Advisor Certification Program, holds a certificate in family wealth advising from the Family Firm Institute, and is certified as a professional coach from the International Coach Federation’s accredited program.

Additionally, he is the author of Legacy: The Hidden Keys to Optimizing Your Family Wealth Decisions and Love Your Clients: the tale of the Whole Family Advisor®. Dr. Orlando sits on the board of directors for Urban Hope in Staten Island. Born and raised in New York City, he resides in Bucks County, Pennsylvania, with his wife and children.

Kristen Heaney, Lead Consultant & Instructor

Kristen Heaney is a Wealth Legacy Coach and Consultant serving successful families and their advisors. Her passion for this work is colored by her own experience of being a young and unprepared inheritor after her father’s early death. Kristen’s training includes a Masters in Social Work from the University of Michigan, a Board Certified Coaching credential, and a certificate in Family Wealth Advising from the Family Firm Institute.

Her book, In Three Generations: A Story About Family, Wealth, and Beating the Odd is a fictional family leadership story, offering a great starting point for those considering a more purposeful approach to handling family wealth. She has been a featured thought leader for the Purposeful Planning Institute, Family Firm Institute, as well as legal, financial, and philanthropic firms across the United States and Canada, focused on topics including rising generation preparation, effective family meetings, wealthism, entitlement, and more. Kristen was born and raised in the Metro Detroit area, and currently lives with her husband and two sons in South Florida.

Kaley Hudson, Associate Consultant & Membership Coordinator

Kaley Hudson leads Operations & Membership at Legacy Capitals. In her role, Kaley manages the Academy Membership, oversees internal operations, drives the team’s creative initiatives, and supports all client engagements. Additionally, Kaley is an associate consultant and individual coach, specializing in personal finance coaching.

Kaley Hudson graduated from the University of Florida where she earned her Bachelor’s degree in Business Management with a minor in Communication Studies. Since then, she has continued her education outside of the classroom setting, completing a Personal & Family Financial Planning certificate program through University of Florida, an extensive coach training program through the CoActive Training Institute, and a Personal Finance Coaching certification through the Financial Coach Academy.

Hallie Gaudio, Internal Operations

Hallie Gaudio works with the Legacy Capitals team on administrative operations, membership development, and special projects. Hallie has a background in program management and marketing and enjoys using these skills to support the mission of Legacy Capitals.

Hallie graduated from Florida State University where she earned her Bachelor’s degree in Business Management. Currently, Hallie is continuing her education at Florida State University and working towards her Master’s degree in Business Administration with a specialization in Marketing.

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