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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

Scaling Success: Why Smart Habits Beat Growth Hacks in Modern eCommerce

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There’s a romanticized image of the eCommerce founder: a daring risk-taker chasing the next big idea, fueled by late-night caffeine and last-minute inspiration. But the reality behind scaled, sustainable brands tells a different story. Success in digital commerce doesn’t come from chaos or clever hacks. It comes from habits. Repetitive, structured, often unglamorous habits.

Change, a digital platform created by eCommerce strategist Ryan, builds its entire philosophy around this truth. Through education, mentorship, and infrastructure, Change helps founders shift from scrambling for quick wins to building strong systems that grow with them. The company doesn’t just offer software. It provides the foundation for digital trade, particularly for those in the B2B space.

The Habits That Build Momentum

At the heart of Change’s philosophy are five core habits Ryan considers non-negotiable. These aren’t buzzwords; they’re the foundation of sustainable growth.

First, obsess over data. Successful founders replace guesswork with metrics. They don’t rely on gut feelings. They measure performance and iterate.

Second, know your customer deeply. Not just what they buy, but why they buy. The most resilient brands build emotional loyalty, not just transactional volume.

Third, test fast. Algorithms shift. Consumer behavior changes. High-performing teams don’t resist this; they test weekly, sometimes daily, and adapt.

Fourth, manage time like a CEO. Every decision has a cost. Prioritizing high-impact actions isn’t optional; it’s survival.

Fifth, stay connected to mentorship and learning. The digital market moves quickly. The remaining founders are the ones who keep learning, never assuming they know it all. 

Turning Habits into Infrastructure

What begins as personal discipline must eventually evolve into a team structure. Change teaches founders how to scale their systems, not just their sales.

Tools are essential for starting, think Notion for documentation, Asana for project management, Mixpanel or PostHog for analytics, and Loom for async communication. But tools alone don’t create momentum.

Teams need Monday metric check-ins, weekly test cycles, customer insight reviews, just to name a few. Founders set the tone by modeling behavior. It’s the rituals that matter, then, they turn it into company culture.

Ryan puts it simply: “We’re not just building tools; we’re building infrastructure for digital trade.”

Avoiding the Common Traps

Even with structure, the path isn’t always smooth. Some founders over-focus on short-term results, chasing vanity metrics or shiny tactics that feel productive but don’t move the needle.

Others fall into micromanagement, drowning in dashboards instead of building intuition. Discipline should sharpen clarity, not create rigidity. Flexibility is part of the process. Knowing when to pivot is just as important as knowing when to persist.

Scaling Through Self-Replication

In the end, eCommerce scale isn’t just about growing a business. It’s about repeating successful systems at every level. When founders internalize high-performance habits, they turn them into processes, then culture, then legacy.

Growth doesn’t require more motivation. It requires more precision. More consistency. Your calendar, not your to-do list, is your business plan.

In a space dominated by noise and novelty, Change and its founder are quietly reshaping the conversation. They aren’t chasing trends but building resilience, one habit at a time.

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