Wealth On Main Street 270: U.S. Immigration Myth: It Isn’t as Hard as You Think
Relocating to the United States might seem like a dream buried under piles of paperwork, red tape, and uncertainty—but the reality might surprise you. In a recent episode of the Wealth On Main Street podcast, hosts Jayson Lowe and Richard Canfield spoke with Rocki Maimone and Filomena L. Maimone, a powerhouse mother-daughter team guiding Canadians through U.S. immigration with clarity and care.
This conversation tackles one of the most common beliefs that holds people back: that U.S. Immigration is nearly impossible.
In truth, with the right plan and team behind you, it can be smoother than you think. Legal pathways for Canadians are very much alive, with a variety of options to suit entrepreneurs, investors, professionals, and families.
Whether you're considering a temporary visa, a permanent green card, or a full lifestyle transition, here’s why the U.S. might be more accessible than you imagined.
Dispelling the Fear: U.S. Immigration Isn’t as Scary as It Seems
Many Canadians hesitate to consider immigration because of fear. They've heard stories of detentions at the border, rejections at customs, or harsh crackdowns on legal entries. But these narratives often stem from misunderstandings or misinformation, not reality.
“You're not going to be detained,” said Rocki, addressing a frequent concern among clients. “Americans still love Canadians. We haven’t seen any issues whatsoever when documents are in order.”
Filomena echoed this sentiment, noting that many people expect immigration to be a brutal process, only to be surprised at how fast and straightforward it can be. “There are a lot of visas out there, some specifically for Canadians, that are not hard to obtain, especially if you have the right team.“
What fuels the fear?
A lot of it comes from Canadian media. According to Rocki, some clients worry they’ll be denied or detained at the U.S. border due to what they see on the news. Yet in practice, properly prepared applicants rarely face issues.
Jayson emphasized the importance of going to the source. “My first question is, have you substantiated your concerns? Or are you relying on Uncle Google or ChatGPT?”
If your documents are complete and you follow the legal process, there’s no reason for fear to hold you back. Legal immigration pathways are open and active, especially for Canadian entrepreneurs and investors.
U.S. Immigration: Legal Pathways Are Wide Open—Especially for Entrepreneurs
The U.S. is still the land of opportunity, and that includes legal immigration options for Canadians. Rocki and Filomena shared that they’ve seen a 100% approval rate for their E-2 visa clients. This visa is designed for individuals who want to invest in or start a business in the United States.
“The E-2 has been around in some form for over 200 years,” said Rocki.
“Small business owners are the backbone of both America and Canada. If you're bringing in money, expertise, and jobs, the doors are wide open.”
Filomena added that even newer business owners or those just starting the journey can qualify, as long as they follow a proper plan. “With our legal team’s meticulous preparation, our clients know they’re set up for success. We even guarantee the application process to provide peace of mind.”
The E-2 visa is just one of several. Other pathways include:
- L-1 executive visa,
- EB-3 for employer sponsorship,
- EB-5 green card by investment.
Many clients begin by opening a subsidiary of their Canadian business in the U.S., then gradually shift operations.
The myth that U.S. immigration is closed for business? Totally false. In fact, business-minded Canadians are welcomed with open arms.
Beyond U.S. Immigration: Legal Support and Business Services Matter
Immigration is just one piece of the puzzle.
Once in the U.S., newcomers often face challenges around taxes, legal entity formation, estate planning, and asset protection.
Rocki and Filomena understand this firsthand, and that’s why their practice doesn’t stop at visa processing. They support clients with:
- Estate planning and trust formation
- Business closings and legal representation
- Health insurance and cross-border tax education
“When we got here, we didn’t know how anything worked,” Filomena said. “So we added services to make sure our clients don’t feel vulnerable or overwhelmed.”
They also partner with business law attorneys and brokers to assist with buying or investing in a business, a core requirement of the E-2 process.
Richard pointed out the value of their holistic approach. “You're not just getting paperwork filed. You're getting a roadmap.”
By offering these integrated services, Rocki and Filomena remove stress from what could otherwise be a complicated process, freeing their clients to focus on building a new life.
U.S. Immigration: Why More Canadians Are Making the Move
The numbers don’t lie: a growing wave of Canadians is actively exploring life across the border. According to Rocki, more people than ever are reaching out for guidance. Her Facebook group alone now exceeds 75,000 members and continues to grow with daily inquiries from families, professionals, retirees, and entrepreneurs all asking the same thing—”Can I really start over in the U.S.?“
The motivations behind the move are as diverse as the people themselves. Some cite frustrations with the rising cost of living, high tax burdens, or increased government control in Canada. Others feel disillusioned by limited business opportunities or concern over their children’s future. But the most common theme is a desire for more freedom, stability, and opportunity.
“I’ve talked to a lot of families where the parents are comfortable staying in Canada,” Rocki shared, “but they’re moving because they want a better life for their kids—better education, more opportunities, and a shot at home ownership.”
The U.S. appeals to entrepreneurs for its business-friendly policies, accessible capital, and growth-oriented mindset. Professionals and remote workers appreciate the freedom to scale careers or relocate without losing economic momentum. For students, American universities offer world-class programs, unique internships, and diverse scholarships not easily found back home.
Filomena added, “Once they see our life, they realize it’s not a fantasy—it’s doable. And we’re here to walk them through every step.”
This is a movement driven by families taking charge of their future. For those who’ve felt stuck or uncertain, stories like these offer a roadmap and a reminder: the U.S. is still open, still thriving, and still full of opportunity for those ready to leap.
What Makes a Successful U.S. Immigration Strategy
Moving to a new country is never just about paperwork. It’s about planning, mindset, and having the right team in place. Rocki and Filomena emphasized that the most successful clients don’t just focus on getting the visa—they focus on building a foundation.
It starts with clarity. Why are you moving? What are your personal and professional goals? For some, it’s owning a business. For others, it’s setting up their kids for success.
Knowing your “WHY” will help guide every step of your strategy.
Next, it’s about alignment. That means working with experienced immigration professionals who understand not just U.S. law but the Canadian context too.
The Maimone team doesn’t just fill out forms—they create a path forward. That includes forming legal entities, connecting with business brokers, and planning for taxes and healthcare.
It’s also important to treat the immigration journey like a business plan. You wouldn’t open a company without forecasting and structure, so don’t move without the same due diligence.
Rocki put it simply: “This isn’t about winging it. The more prepared you are, the smoother the process.”
If you treat your U.S. move as a well-managed transition rather than a leap of faith, the odds of success increase dramatically.
How U.S. Immigration Opens Doors to Wealth and Freedom
When most people think about immigration, they focus on lifestyle. But as Rocki and Filomena explained, it’s also a financial strategy.
The U.S. offers an environment that favors business ownership, tax planning, and wealth creation. With a strong dollar, lower business taxes in many states, and access to funding, your income has more room to grow—and so does your legacy.
“A lot of our clients are building generational wealth now because they made the move,” Rocki noted.
“They’re able to buy homes, invest in property, and structure their business in a way that maximizes cash flow.”
This is especially true for investors and entrepreneurs. The E-2 visa, for instance, allows Canadians to operate U.S. businesses while living in the country. With the right setup, they can pay themselves a salary, reinvest profits, and plan for retirement—all from inside a system that supports growth.
There are also estate planning advantages. Filomena helps clients:
- Create trusts and other legal frameworks that protect assets
- Reduce tax liability
- Ensure wealth is passed down efficiently
If financial freedom is part of your dream, moving to the U.S. could be a powerful part of your wealth-building journey. The tools are available—you just need to take the first step.
Real Clients, Real Rewards: Why They Do What They Do
What makes this work so rewarding for Rocki and Filomena? It’s the transformation they get to witness.
“For me,” Filomena said, “it’s seeing someone who’s scared and unsure become confident and successful. Getting that visa approval—it’s just such a moment of joy.”
Rocki echoed the sentiment, adding that she loves being a part of family transitions. “I want kids to say, ‘Thank God my parents moved because of Rocki.’ That’s what drives me.”
Their clients aren’t just case numbers. They’ve developed deep friendships, celebrated over dinners, and even received heartfelt gifts. This isn’t just legal support—it’s personal.
Jayson summarized it perfectly:
“You’ve filled a gap that people didn’t even know they needed. You’ve been through the experience yourself, and now you’re guiding others with heart and wisdom.”
Conclusion
U.S. immigration doesn’t have to be complicated, intimidating, or filled with uncertainty. The truth is, the path is often much clearer than you think, especially when you work with the right guides who’ve not only helped others but walked the journey themselves.
Rocki and Filomena Maimone are living proof that the American dream is still alive for Canadians—and accessible for those willing to take the first step. From navigating visas to helping you open a business, plan your taxes, and protect your legacy, they’re the team that turns overwhelming into achievable.
If you're sitting on the fence, wondering whether it’s possible, take this as your sign. You have options. You have support. And most importantly, you have a future that could start with one decision.
Tune in to the full episode of Wealth On Main Street and hear why this could be the most life-changing conversation you’ll have all year.
For more information, watch the full episode here and grab a copy of Don’t Spread the Wealth. Discover how to make the infinite banking concept work for you.
Rocki Maimone is a seasoned Canadian businesswoman with over 30 years of experience in marketing, senior housing, and real estate. At Maimone Legal PLLC, Rocki’s commitment to delivering exceptional results makes her an invaluable asset to both the firm and its clients.
Website: https://www.maimonelegal.com/
Instagram: https://www.instagram.com/maimone_legal/
Facebook: https://www.facebook.com/maimonelegal
LinkedIn: https://www.linkedin.com/company/maimone-legal/
YouTube: https://www.youtube.com/@MaimoneLegalPLLC
Filomena L. Maimone is a dedicated Immigration Attorney with a strong passion for assisting individuals in navigating the complexities of the immigration system. As an immigrant herself, she brings a unique understanding and empathetic approach to her practice. Filomena earned her Bachelor of Arts Degree at York University in Toronto, Canada, and went on to obtain her Juris Doctor (J.D.) from Nova Southeastern University, Shepard Broad College of Law. As an immigration attorney, Filomena is dedicated to helping clients achieve their immigration goals and build a brighter future in the United States.
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