Richard Orlando

Richard J. Orlando, Legacy: The Hidden Keys to Optimizing Your Family Wealth Decisions
(Legacy Capitals Press, 2014)

LEGACY_COVERBuy It on Amazon

Buy It on Kindle

Buy It on Barnes & Noble

Buy It on Indie Bound:


icon-subscribeListen to Richard on ‘The Sessions’ Podcast



Your legacy is how you live, not just what you leave.

Family wealth is often emotionally charged, whether you have a small nest egg or financial abundance. Wealth creates unique opportunities and challenges. The greatest challenge is the least discussed: the place where money, values, and family intersect. As the level of our wealth increases, our decisions become more complex and sophisticated.

In Legacy, Dr. Richard Orlando explores the five most important family wealth decisions that directly impact us, our families, and our legacies. Orlando offers wisdom, stories, and step-by-step advice for optimizing these decisions by aligning them with our values, purpose, and faith, in essence, our spiritual capital. These questions involve leading a happy and fulfilled life, the ability to transfer wealth, preparing the next generation for the opportunities and responsibilities of wealth, and so on. If you are concerned about one or more of these issues, or if you are a professional advisor who has tried to help your clients with these issues, this book is a must-read.


“In this insightful and much-needed book, Richard Orlando, trusted advisor to many of the world’s wealthiest families, shares the essential strategies he uses to help his clients make value-driven decisions about managing their wealth and establishing a meaningful multigenerational legacy.”

Chip Conley, New York Times bestselling author of Emotional Equations

“Richard Orlando’s financial management advice shows we can live a connected, service-oriented life in touch with our values while building an enduring family legacy of success. Orlando provides critical guidance for navigating major life decisions to make sure they strengthen relationships rather than driving families apart.”

Keith Ferrazzi, New York Times bestselling author of Who’s Got Your Back and Never Eat Alone

“I’ve long been an admirer of Dr. Orlando’s groundbreaking work helping families integrate their spiritual and financial ideals. His book is an excellent resource for those who still feel there is something important lacking in the wealth management experience.”

Hannah Shaw Grove, author of The Family Office

“Richard Orlando’s new book, Legacy brings into our consciousness the fundamental role of spiritual capital in a family’s flourishing and in the happiness of its individual members. Richard teaches us that when a family’s human, intellectual, social, and financial capitals are joined with its spiritual capital it stands a strong chance of avoiding the universal cultural proverb ‘short sleeves to shirt sleeves in three generations’ and the suffering it defines. My reading of Richard’s book affirms my strong belief in his conclusion and its message offers great value to families everywhere and their advisors.”

James E. Hughes, Jr., author of Family Wealth and Family, and coauthor of The Cycle of the Gift

“Richard’s book brings a new and challenging perspective to the estate planning profession. Legacy is filled with stories, principles, and a framework for those of us who want to expand our value to our clients. In particular, the chapters on wealth transfer and preparing the next generation make a compelling case to factor the next generation into the planning process. I would recommend this book to every advisor and family who is ready to look beyond conventional wisdom as they plan for their legacy.”

David A. Stein, partner and head of U.S. Wealth Planning, Withers Bergman, LLP

“Given the uncertainty and volatility of the financial markets, Richard Orlando’s book is a beacon of wisdom, savvy, and experience for legacy and investment managers. It is the ultimate wealth preservation and growth book for all to savor or aspire to. I recommend it highly.”

Ernest D. Chu, author of Soul Currency former Wall Street Journal staff writer, former member of the New York Stock Exchange

“I have had the privilege over my professional career of advising many families on their wealth transfer decisions. It is always very complex, as no two family situations are the same and there are seen and unseen dynamics at play. Dr. Orlando approaches this topic with wisdom and principles based on considerable experience. This book should be a very valuable resource both for professionals and anyone with wealth transfer opportunities and issues. I recommend this book with enthusiasm.”

Ron Blue, founder of Kingdom Advisors and Ronald Blue & Company

“A MUST-read. It will forever change the way you think about your family and estate.”

Paul A. Pagnato, managing director and partner, Pagnato-Karp Group, a Barron’s 2013 top 100 financial advisor

“Richard Orlando provides practical wisdom and excellent insight into the complex set of subjects surrounding legacy planning. He expertly argues the what, how, and why questions, pointing out that optimizing these decisions is about intellectual, social, human, and spiritual capital, not just financial capital. Recommended reading for anyone serious about the subject of legacy.”

Bob Doll, chief equity strategist and senior portfolio manager, Nuveen Asset Management

“Richard’s passion for helping people navigate the increasingly complex world of financial choices is laudable. His approach demystifies and simplifies, giving investors the peace of mind they deserve.”

Elliot Weissbluth, CEO of HighTower

“Dr. Richard Orlando’s book, Legacy, provides the necessary guidance to help families optimize their family wealth decisions and prepare their family for the wealth. In particular, his focus on next-generation preparation does an excellent job of pointing out what wealthy families need to provide to their children. Following Dr. Richard Orlando’s ‘Ten Principles and Practices for Parents to Raise Their Children’s Life IQs’ is a great place for parents to begin this process.”

Rowland M. Smith III, C.P.A., CSEP, M.S.T., tax partner at ParenteBeard LLC

“As CEO of an international company, I have read many books on leadership, wealth, and success. Of these, Dr. Orlando’s book is in a class by itself. Legacy provides principles and insights that can assist business owners and entrepreneurs in their pursuit to prepare themselves and their children for the opportunities and responsibilities that come with success. This book is a must-read for anyone interested in creating a positive legacy through their company and family.”

John Rakolta, Jr., CEO of Walbridge

“After playing basketball in the NBA for the past twelve years and now planning for the next stage of my life, I couldn’t have read a better book. It is filled with practical wisdom that’s guiding me and my family from success to significance. I wish this book would have been available earlier in my career. I strongly recommend it to professionals who want to make the best possible decisions regarding their wealth, success, and family.”

Michael Redd, former NBA player (2000–2012) and member of the USA National Men’s Basketball Team (gold medal winner, 2008 Summer Olympic Games)


For the past quarter century, Richard Orlando, Ph.D., founder and CEO of Legacy Capitals LLC, has worked globally with individuals, such as executives, entrepreneurs, professional athletes, and entertainers, as well as families, work teams, and organizations, who strive for success or have already reached significant levels of success.

More specifically, Dr. Orlando serves as a trusted advisor, consultant, and coach to some of the world’s wealthiest families—some of which lead very successful family businesses. In addition, he has worked with Barron’s Top 100 Financial Advisors, as well as leaders and high-performing teams nationally and internationally.

Dr. Orlando has an interdisciplinary background, holding degrees in computer science, business, and psychology. After earning a Bachelor of Science degree in computer science and business from St. John’s University, he pursued a career on Wall Street and earned his Series 7 and 63 licenses. Returning to school, he received a master’s degree in counseling/theology from Trinity International University. Continuing his education, he earned a doctorate in family systems from Seton Hall University, during which time he interned with the New York Giants football team. His dissertation research focused on wealth management family teams. Dr. Orlando also earned a certificate in family wealth advising from the Family Firm Institute and holds a certified professional coach designation from an International Coach Federation accredited program.

Dr. Orlando has been featured in numerous publications such as the New York Times, Wall Street Journal online, Private Wealth Magazine, CFA Magazine, Merrill Lynch Advisor, Research, Bloomberg Wealth Manager, On Wall Street, and Registered Rep. He has conducted hundreds of presentations to various groups and organizations, among them Merrill Lynch, U.S. Trust, HighTower, Dynasty Financial Partners, Janney Montgomery Scott, Young Presidents Organization, and Vistage International. He’s also spoken at the conferences of Barron’s, Securities Industry Institute, and Investment Management Consultants Association.

Dr. Orlando is on the board of director’s of Urban Hope in Staten Island, New York. He was born and raised in New York City, and currently resides in Bucks County, Pennsylvania, with his wife and their children.