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Finding Financial Freedom With the Help of CEO Richard Dolan

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Richard Dolan is the CEO and founder of LEGACY, a Toronto-based privately held boutique firm specializing in providing resources to those looking to understand their finances better. 

He is a wealth merchant specializing in bringing financial life education, solutions and possibility to his clients with power, grace and ease. The company offers mentorship, advisory services, and coaching to its thousands of clients worldwide. With years of experience in the industry, Richard has perfected his strategies for helping others achieve financial freedom.

Having started as an understudy to financial global thought leaders, investment advisors, and institutions, Richard has come to obtain a great deal of knowledge about different aspects of the industry. He’s used it to help him create the best resources for every client who approaches his company for help, and it’s safe to say he’s found that winning approach.

Richard and his company have collaborated with a number of big brands in the finance industry, including ING, Trimark Mutual Funds, BNP Paribas, Societé Generale, Fidelity Investments, CIBC, TD Bank, Royal Bank (RBC), Scotiabank, and National Bank of Canada.

Within the last 30 years of his career, Richard has come a long way from where he started at the age of 16. Richard’s first introduction to wealth management was shortly after he was kicked out of his home and had to fend for himself. He found a job at a Bay Street firm, where he was tasked with cold calling clients all day, every day.

As Richard watched all the businessmen in the office, he knew that he wanted to reach the same level of success one day. None of them ever brought a lunch to work, always going out in their luxury cars, then coming back to talk about what they did at their summer homes. That wealth is what Richard set his sights on, and for the next few years, he worked hard until he co-founded his first asset management company at the age of 23.

After scaling his business for a few years and raising $1 billion in assets, Richard and his partner sold it for $144 million. This experience taught Richard a fair deal of essential things, like persistence and going for one’s goals. He went on to apply both of these to all future ventures, including when he obtained a position as the president and partner of one of North America’s longest-running private real estate investing network groups before selling his share in 2019.

Today, Richard focuses on LEGACY and helping others reach the heights he has. Public speaking has been an excellent tool for that. He’s even found himself on stage alongside Michelle Obama, Hillary Clinton, Oprah Winfrey, Ellen Degeneres, Sir Richard Branson, Deepak Chopra, and others. Richard has also toured with US presidents Bill Clinton, George W. Bush, Barack Obama, and Donald Trump.

Richard shares his experiences on his Instagram, @Richie_Dolan, and offers insight into his life. More information can be found on his website, RichardDolan.com.

The idea of Bigtime Daily landed this engineer cum journalist from a multi-national company to the digital avenue. Matthew brought life to this idea and rendered all that was necessary to create an interactive and attractive platform for the readers. Apart from managing the platform, he also contributes his expertise in business niche.

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Business

Private Listings by Harold X. Clarke: A New Approach to Fine Real Estate

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Photo credit: Private Listings by Harold X. Clarke.

Byline: Andi Stark

Private Listings by Harold X. Clarke, a real estate platform operating across Hawaii, is rewriting how properties are bought and sold in the region. Unlike larger firms reliant on public listings and mass marketing, Private Listings’ strategy prioritizes personalization, privacy, and meticulous curation of ultra-high-end, off-market properties, including oceanfront estates, gated community residences, and architectural masterpieces.

Harold Clarke, founder of Private Listings, describes their method as one that rejects “cookie-cutter solutions in favor of understanding the nuances of both buyers and sellers.” This approach has resonated with ultra-high-net-worth individuals (UHNWIs) seeking refined and discreet real estate transactions.

The Hawaiian real estate market remains a hub for global investors, with the median price for a single-family home in the state reaching $900,000 in 2024, according to the Hawaii Association of Realtors. Within this competitive landscape, Private Listings is building up to be a trusted name for properties that extend beyond luxury into generational investments.

Challenging the Industry Norms

Private Listings deliberately avoids the conventions of large-scale real estate firms. By focusing on fewer, higher-value properties, the company ensures that each transaction is treated with the same level of care and confidentiality.

Public listing platforms, while effective for broader markets, often expose sellers to unnecessary attention or unqualified inquiries. For Clarke, this model is misaligned with the needs of UHNWIs. “Privacy isn’t a luxury for our clients—it’s a necessity,” Clarke explains.

This philosophy has led Private Listings to handle some of Hawaii’s most significant real estate transactions, including off-market properties valued at over $40 million. Its success is not measured by the volume of listings but by the depth of trust built with clients, many of whom return for subsequent transactions.

Adapting to Changing Client Demands

While Private Listings maintains a foundation of traditional practices, the firm also recognizes the evolving needs of its clientele. The global real estate market is increasingly influenced by concerns over digital security, with a 15% rise in data breaches targeting high-net-worth individuals in the past three years, according to cybersecurity firm NortonLifeLock.

To address these risks, Private Listings employs rigorous screening for potential buyers and uses secure platforms for communication and transactions. The firm’s “by invitation only” model ensures that clients remain protected from the pitfalls of public exposure. Clarke notes, “Our goal is not just to sell homes but to create an environment where clients feel safe and confident during every step of the process.”

The Human Element in Real Estate Transactions

Despite advancements in technology, Private Listings firmly believes that real estate transactions cannot be reduced to algorithms or automation. Unlike firms that depend heavily on online data aggregation, Private Listings emphasizes human connection and insight.

The company’s sales strategy integrates personalized client interactions, in-depth market analysis, and years of experience navigating Hawaii’s unique real estate ecosystem. Clarke’s background in managing family assets and his global perspective is significant in shaping this essence.

Future Directions for Private Listings by Harold X. Clarke

As Hawaii continues to attract global attention, Private Listings aims to expand its influence within the state while maintaining its core principles. The company is currently developing a new platform to streamline services for UHNWIs, blending their demand for discretion with seamless access to Hawaii’s finest off-market properties.

Additionally, Private Listings is strengthening its ties with local communities, recognizing that sustainable growth benefits both the company and the islands’ ecosystems.

Private Listings by Harold X. Clarke has set itself apart in Hawaii’s real estate scene by moving away from the typical mass-market approach. Through a mix of traditional values and modern sensibilities, the firm continues to define what it means to transact ultra-high-value properties with integrity and care.

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