Academy Team

Richard Orlando 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 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 Fennell ASSOCIATE

Kaley Fennell graduated in May 2018 from the University of Florida where she earned her Bachelors degree in Business Management and a minor in Communication Studies. Her most meaningful experience in college was through the Heavener Leadership Challenge, a business organization which seeks to demonstrate to students that leadership is a learnable skill.

Currently, Kaley is in an associate role with Legacy Capitals. Within this role, she assists in client engagements and project work as well as manages the logistics of the Academy courses.

Since July 2020, she has been working towards achieving her Professional Coach Certification through the Co-Active Training Institute’s Coach Training and Certification courses.