Moving from Canada to the U.S.: What Entrepreneurs Should Think Through Before Taking the Leap

You can build a successful business and still feel that the life around it no longer fits. Perhaps you want access to different customers, a more active business community, or a place where you can spend more time outdoors. Then the practical questions arrive. What happens to your company? Can your family move with you? How much will the whole thing cost?

In this episode of the Founder2Founder podcast, Aaron Spivak speaks with immigration attorney Mena Maimone about Canadian entrepreneurs considering a move to the United States. Both have made that transition themselves, and neither hides their enthusiasm for Florida. Their conversation combines personal stories with questions about visas, family life, and building a business in a new country. The most useful lesson is to turn a large, intimidating decision into a series of specific questions you can answer.

Why the Conversation Goes Beyond Taxes

Spivak and Maimone describe frustration with the business environment they experienced in Canada. Taxes, public services, safety, and opportunities for growth all come up. Their comments are strongly shaped by their own experiences and the entrepreneurs around them. They are explaining why the move appealed to them, rather than offering a complete comparison of two countries. For a reader considering relocation, the useful question is which of those concerns actually applies to their own life.

Spivak makes a broader point about environment. He had long believed that surrounding himself with ambitious people mattered, but initially thought a small circle of good friends could provide that anywhere. Living in Miami changed how he understood the influence of his wider surroundings. He describes feeling more energised by the people, activities, and opportunities around him. The setting became part of how he wanted to live and work.

That is worth examining before looking at visa forms. A move should have a positive purpose beyond escaping frustration. Perhaps the goal is to serve an American market, build relationships in a particular industry, or create a different family routine. Naming that purpose helps you judge possible destinations. Otherwise, it is easy to compare your hardest ordinary day at home with somebody else’s best day abroad.

Maimone’s Own Move Started With a Café

Maimone was twenty-two when she bought a café in the United States. She wanted to leave Canada and was willing to learn the business as she went. Looking back, she acknowledges that the experience was challenging and that she did not arrive knowing how to run a café. She had to work things out gradually. That experience later influenced the way she approached clients facing a similar transition.

She eventually attended law school and found a professional focus in helping other people relocate. Her advice in the conversation is rooted partly in remembering her own uncertainty. She wishes she could have told her younger self that she did not need the entire future mapped out. She needed to understand the next step well enough to take it. There is a difference between accepting some uncertainty and proceeding without preparation.

Her story also brings the business itself back into focus. Buying a company to support a move means taking responsibility for an actual operation. Customers still need service, expenses still need paying, and the owner still needs to understand the work. The immigration objective does not replace those demands. A business that fits your abilities and interests deserves as much attention as the destination.

Replace General Fear With Specific Questions

Maimone says many consultations begin with anxious clients who do not know where to start. By the end, they often feel calmer because the process has become more concrete. Their circumstances have not magically changed during the call. What has changed is their understanding of the available options and the work involved. A sequence feels more manageable than a collection of unanswered worries.

For an established owner, the first discussion should connect the proposed move to the existing business. Will the Canadian operation continue? Is there already American revenue? Does the owner want to buy a company, establish a new one, or expand an existing service? These questions help explain what is being proposed before anyone starts treating one visa category as the obvious answer.

The family’s plans belong in that conversation too. A spouse’s work, children’s schooling, and the intended length of stay can materially affect the decision. So can the amount of capital available after allowing for living expenses. Maimone repeatedly returns to the value of having an appropriate team. The point is to understand how the different pieces fit before committing to an expensive sequence of steps.

Understand What the E-2 Route Actually Requires

The E-2 treaty investor visa receives considerable attention in the episode. It is a nonimmigrant category associated with developing and directing a qualifying U.S. enterprise. The investment must be substantial, and the business must be real and operating. Simply leaving money in an account is not the same as making a qualifying investment. The official requirements also address the enterprise’s economic contribution and the investor’s role.

Maimone frequently uses US$100,000 as a practical investment figure in her discussion. However, that is not a universal legal minimum or an amount that guarantees approval. U.S. Department of State guidance states that there is no fixed minimum investment amount for E-2 purposes. Substantiality is assessed in relation to the enterprise and its cost. That makes the proposed business important, not just the headline number.

The business plan deserves careful thought for another reason: the owner’s ambitions may evolve. Maimone recalls feeling restricted by the café business she initially chose. She now asks clients what related activities they may want to pursue. That is a useful planning conversation, but broad wording should not be treated as permission to undertake any future activity. Material changes need review against the applicable immigration requirements.

Existing Trade May Point to a Different Discussion

The episode also introduces the E-1 treaty trader category. For a company already doing business across the border, it may be worth discussing with counsel. Official guidance requires substantial international trade, with more than half of the relevant international trade occurring between the United States and the treaty country. Qualifying trade can include services as well as goods. The podcast’s revenue example should not be treated as a universal eligibility threshold.

This distinction matters because two owners with similar revenue may have very different cases. One may be investing in a new American enterprise, while another already has continuing trade between the two countries. Neither should select a route simply because a friend used it successfully. The existing ownership, transactions, and proposed activities need to be understood together. That is where a tailored assessment earns its value.

It is also important to distinguish permission to operate under a nonimmigrant category from permanent residence. An E visa is not itself a green card. The episode discusses possible future routes, but those involve separate requirements and decisions. A useful plan addresses both the immediate business objective and the owner’s longer ambitions. It does not assume that one approval automatically settles the other.

Departure Tax Deserves Its Own Planning Conversation

Spivak raises a concern many owners share: what happens to their Canadian assets when they leave? Maimone makes clear that taxation is outside her primary area of practice and describes involving a cross-border accountant. That division of responsibility is one of the stronger practical points in the interview. Immigration planning and tax planning are connected, but they are not interchangeable.

Canada does have departure-tax rules. The Canada Revenue Agency explains that leaving can trigger a deemed disposition of certain property at fair market value, potentially creating a taxable capital gain even without an actual sale. This does not mean every asset is taxed in the same way. Tax residency also involves residential ties and relevant treaty rules, rather than simply counting travel days.

For a business owner, the implication is to obtain an individual assessment before reorganising ownership or making relocation commitments. The company, personal assets, family circumstances, and timing may all need consideration. Spivak’s own ongoing tax work illustrates why the issue should not be reduced to a reassuring slogan. Clear advice is more useful than either assuming everything will be lost or assuming nothing needs to be done.

Compare the Life You Will Actually Be Living

Both speakers are enthusiastic about Florida’s weather and outdoor lifestyle. Spivak describes playing sport in the morning and walking to the beach near his home. Maimone talks about the opportunities her family found after moving. These details explain why relocation feels worthwhile to them. They also show that the decision is about ordinary routines as much as business performance.

Healthcare and education come up as areas where prospective movers often have concerns. The speakers share positive personal examples, but those examples do not establish what another household will pay or qualify for. A family needs its own information about coverage, schools, admissions, and any scholarship conditions. The useful comparison is between realistic options for that household. Broad national claims cannot do that work.

Spivak also describes a frightening home invasion in Toronto that influenced his decision to leave. His experience helps explain the emotional weight he gives personal safety. It should not be converted into a claim that every American neighbourhood is safer than every Canadian one. For someone planning a move, local research matters. The actual neighbourhood, commute, and daily routine are more useful units of comparison than a whole country.

Budget for More Than the Application

Asked about professional costs, Maimone mentions approximately US$10,000 for an average client arrangement in her practice. She describes a process that may involve months of support and related planning. That figure is her example from the conversation, not a quote for every reader. Before relying on it, a prospective client would need a written explanation of scope and exclusions. Investment capital and ongoing business expenses are separate considerations.

The wider budget also needs room for the household transition. Housing, moving, transport, professional advice, and the period before a business generates dependable income can all affect available cash. A plan that uses every dollar to establish the enterprise leaves little flexibility for surprises. The question is not only whether the family can afford to arrive. It is whether the business and household can function while the transition settles.

Spivak’s interview story adds another perspective. He recalls extensive preparation followed by a much shorter conversation than he expected. His experience helped make the process feel less intimidating, but he acknowledges that others may have different experiences. Preparation remains worthwhile even when the final exchange is brief. A calm interview is an outcome to appreciate, not a reason to skip the work behind it.

Building Trust Is Also a Business Strategy

One of the most engaging parts of the episode concerns Maimone’s business relationship with her mother. After law school, she wanted to build a firm with someone whose commercial judgement she trusted. They began in a room with their desks facing each other and no established client base. Their early focus was practical: answer questions, return calls, and treat people well. Over time, she says, the enquiries grew.

She credits their compatibility partly to agreement about how clients should be treated. Her mother brought years of business experience, while Maimone brought her legal training and determination to build the practice. The family connection mattered, but so did the shared approach to service. They could support each other because they understood what they were trying to create. That lesson extends beyond a family business.

Relocation clients are making decisions that affect their work, finances, and home life. Responsiveness therefore carries real weight. Maimone describes wanting clients to feel supported throughout the process, rather than merely handing them a list of documents. For founders listening, that is a reminder about their own customers. Clear communication can make a complicated service feel more manageable without pretending the work is effortless.

Make the Next Step an Informed One

The conversation is an enthusiastic case for considering life in the United States. Its most transferable lesson, however, is about replacing assumptions with a plan. Understand what you want from the move, how the business would operate, and what your family needs. Then assess the immigration and tax questions together with the appropriate professionals. You do not need certainty about every future detail, but you do need reliable information about the commitments ahead.

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