From Tribulations to Triumph: The Inspiring Success Story of Richard Dolan

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Richard Dolan is a self-proclaimed “financial leadership guy,” but he is so much more than that. This seven-figure-earning coach, mentor, author, and public speaker has helped guide entrepreneurs, investors, workplace leaders, and global brands to success. Even as the Business Coaching industry’s revenue hit a 7.5% decline in 2020, according to IBISWorld, Dolan remains optimistic about his impressive goal to “create 1,000 NEW millionaires in five years.” Although he’s a highly successful coach and businessman today, life hasn’t always been easy for Dolan. Here, he talks about his past, some of the challenges he’s faced, and how he overcame them to become the leader he is today.

Humble Beginnings

Dolan was an inner-city kid who grew up in a lower-middle-class family. He recognized early on the importance of escaping the predictable path of street living, drugs, and crime if he didn’t want to follow the usual course for young people in that environment. Luckily for him, he fell in love with the idea of what wealth could do for him, his life, and those he loved. However, he lacked the financial security and bandwidth to establish a business framework and foundation. With no safety net, no plan B, and no help, Dolan put all his cards on the table and became an entrepreneur at just 16 years old.

Powerful Inspirations

Gordon Gecko, a fictional character played by Michael Douglas in Oliver Stone’s 1987 film Wall Street, was a big inspiration to Dolan. The movie aggressively encapsulated the stock market’s spirit and fervor, and Richard Dolan related to that as the sort of life he wanted to experience.

Fast-forward to 2011, Richard met Juwan Howard, a member of the NBA team, the Miami Heat. This meeting was a turning point for Richard as Juwan introduced him to the world of professional sports and high-powered celebrity athletes, including fellow teammates Lebron James, Chris Bosh, and Dwayne Wade. These introductions 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. Soon, Richard was given two NBA championship rings by Juwan during the Miami Heat’s back-to-back wins in 2012 and 2013 for his role as an advisor during that time.

Today’s Leader for Tomorrow’s LEGACY

Over the years, Dolan has been a founding member of various businesses in the wealth management and investment banking sectors. He’s served hundreds of clients and overseen the management of nearly $10 billion in client assets before migrating to the world of real estate investing. Dolan served as president and partner to one of North America’s longest-running private real estate investment network groups, measuring over $5 billion in value. In 2019, after eight years in the business, he sold his share for an undisclosed amount.

Today, Dolan heads up a privately held boutique firm called LEGACY, specializing in getting people’s relationships right with money, wealth, and worth. He achieves this through coaching, education, mentorship, and advisory services. He and his team work with clients seeking to learn and live a financial life by design and professionals seeking competitive immunity, such as financial planners, investment advisors, wealth managers, and insurance professionals.

Richard Dolan believes that all people can live, lead, and leave a financial legacy with power, grace, and ease.


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