What do Bill Clinton, Mike Tyson and Oprah Winfrey have in common? Enter Richard “Richie” Dolan — a financial guru with a 30-year tenure in the private wealth and real estate industries, who raised over $7 billion in assets, and is now hell-bent on mentoring others to secure a better financial future.

Dolan is currently the head of a boutique firm named Legacy, specializing in improving people’s relationships with money, wealth, and worth. However, he has one passion he is fanatical about; Richie wants to create one million, millionaires, by 2030 — read that again — which he believes is achievable through transforming our relationship with money, wealth and worth through assessment, education, planning and action.

Richie has toured the globe with four United States presidents and shared a stage with Oprah Winfrey, Michelle Obama, and Ellen Degeneres. He’s provided invaluable strategic intelligence to the likes of Mike Tyson, and Steve Aoki, and worked with corporate monoliths like Google, Bentley Motors, Chanel, and Pagani Automobili.

Richard has been a founding member of various businesses in the wealth management and investment banking business. He’s served hundreds of clients and oversaw the management of nearly $10B in client assets before migrating to the world of real estate investing. Richard served as President and partner to one of North America’s longest-running private real estate investment network group representing over 35,000 doors owned measuring over $15B in value. He sold his share in the business after eight years in 2019 for an undisclosed amount.

In 2011 Richard met Juwan Howard, a member (and later coach) of the Miami Heat. This was a turning point, as Juwan introduced him to the world of professional sports and high-powered celebrity athletes including then fellow teammates, Lebron James, Chris Bosh and Dwayne Wade. This led to the launch of a private pension plan with Juwan Howard for fellow NBA players, specializing in real estate investments in pre-construction properties across North America. Juwan gifted Richie his two NBA championship rings he won with the Heat for his role as advisor during that time.

His focus now is to take this experience and share it through his education, programs, advisory services, and coaching. As the chief architect of an academic certificate program, “The Financial Life Professional,” Richie leads through lectures, coaching, and mentorship to show how to live a prosperous financial life. Drawing from research areas such as financial psychology, behavioral finance, investor resilience, and the “economics of happiness,” giving rise to his very own “urban financial philosophy.” A few stand out pieces of advice; when asked how he builds his teams, he replied it is best to “look for people that think and act like owners and are willing to stand for success over self-significance” — how to scale a business? Try “hiring people smarter than yourself.”

Richie grew up in a mixed (South American mother and Eastern European father) lower middle-class family and lacked the financial bandwidth to establish the framework to start the life of an entrepreneur. Despite this, with no safety net, no plan B, and no assistance - Richard willed himself to become an entrepreneur at the age of 16 and he never looked back. In his belief, if he did it, you can do it too. Of course, assuming you have the right discipline and financial education.

“I was inspired by the drive of a fictional character named Gordon Gecko, played by Michael Douglas in the movie Wall Street. To me, he exuded confidence and, notwithstanding his moral compass, I was drawn in by the endless possibilities the world of stocks, bonds, mutual funds, and real estate represented, which lit the flame within me to pursue my ninth zero unapologetically.”

However, unlike Gecko, to Richie integrity is paramount. He has rejected offers during his career, primarily due to the other party lacking integrity and commitment, two of his own personal core values. “If I have fundamental disagreements with someone on our set of values, I simply can’t make myself work with them. The beauty of being an entrepreneur, actually, is that I don’t have to. I have all the freedom of choosing my partners and projects,” says Dolan.

A self-described “financial leadership guy” with a desire to teach people the fundamentals of finance, blessed with unbridled business acumen, maybe his dream to create one million, millionaires, by 2030, isn't so outlandish after all.