Visa Hacking Your Way Across the US Border

I’m truly fortunate to have been able to travel extensively for work in the US and abroad. As a Canadian, you’d think it would be easy to go across borders freely with a simple smile and a thank you. No, dear readers – its not. Although, the US and Canada have an extensive border, its like going through a straight out interrogation every time (of course this makes sense post 9/11). The US does not want Canadians to work there. It’s not impossible though, you just need to jump through a bunch of hoops of fire. First, you need a US company to hire you because of your extraordinary and unique skills that they can’t find in the US. Then, the company has to fork out a hefty amount of cash and paperwork for your VISA to the government which then awaits approval. Finally, with VISA in hand and all your life’s possessions, you cross the border and hope that you don’t get a border protection guy/gal who is having a bad day and rejects the VISA. I had a friend who went through this process so I am all too familiar with the stress and frustration it caused her.

But, what if you’re an entrepreneur and your clients or potential clients exist in the US? Try explaining that to the Border Protection agent, you might as well say you’re carrying drugs.

Imagine trying to explain a South Asian dating site called TwoMangoes to a border protection agent.

Purpose of the trip? To do promotions as a club. (um, FML).

Then there were the t-shirts and gum packets to explain. You mean these were exported into Canada from the US and you’re bringing them back in to give out for free?! It was a disaster from beginning to end. However, after a year of this back and forth by plane, car and bus, I learned quite a lot. Here are some general pointers:

  • At the border, you need to be clear and confident about what you’re saying, while making direct eye contact. Do not hesitate or cower. If you do, you will be stopped and questioned even if you’re just going for a vacation. Then, it just becomes a waste of time at the border as you sit in a room full of foreigners to await further questioning.
  • It’s never advisable to lie. Especially if you’re carrying items that you are planning to leave in the States (in our case, t-shirts and gum). If you lie badly and they search your bags, then they will not let you pass.
  • If you’re going across the border and you tell them its for business reasons and you don’t have a VISA to support that, you will be stopped and questioned. This is not a bad thing. They just want to know everything about the nature of your business from A to Z including when you will return, what items you’re carrying, what you’re leaving in the States and even check your business website to verify. Apparently, you may have to pay a tax based on what you’re carrying. Other times, you may need letters of invitation. It’s all very convoluted and unclear.
  • The easiest way to go across the border is via bus. When you get to the border, everyone must exit with their luggage and go through customs. Since there are usually 60 people on the bus and there is a schedule, no one usually stays behind to get questioned or is stopped completely. It’s a rare occurrence as the agents are slightly more lenient. (What business person would take a bus anyway?) But, as an entrepreneur, the overnight bus is the most economical means of transportation). I have never had an issue going through customs on a bus probably because you usually hit the border in the middle of the night. (But I’m not saying it can’t happen).
  • As a Canadian, the longest you can stay in the US is 3 months with no VISA.
  • Besides carrying items, the other consideration is your return (ticket) or date. You must have one. If you don’t have one, this is another indication that you’re shady and shouldn’t be let into the country.

So these are all straight forward rules, but as entrepreneurs, you have to bend the rules a bit, let’s call it visa hacking. Please note: I have never done anything illegal. I also have never had any intent to sell anything in the States (like importing or working). I am talking only about that grey area; meetings, conferences, accelerator programs, events and promotions.

  • If you are not carrying business items, this is when its a bit easier to cross the border. The go-to advice is to say you’re visiting family. If you say you’re visiting friends and appear “shady” looking – they will dig deeper and ask how you met those friends. Unfortunately, saying you met them through twitter won’t fly #truestory. Again though, be clear about your return date. In some cases, its advisable to get a return flight even if you don’t intend to return on that date just to cover your basis. When I went to SF for 500 Startups, I bought a direct flight to SF with a return ticket 3 weeks later. I obviously didn’t take that flight. I stayed for my allotted 3 months, flew to NYC and took a bus to Toronto.
  • So you’re innocently carrying just your clothes, some cash and have a return date. More than 95% of the time, they will ask you your occupation. It’s standard, especially if you’re saying you’ll be in the US for more than 2 weeks. What job allows that much vacation? My response is that I am a freelance tax consultant (kind of true) or I say freelance social media/marketing consultant. The tax consultant works brilliantly right after April, since that’s when tax season is over. For all other times of the year, I just say marketing. You never want to say entrepreneur or self-employed – this leads to visions of you taking over jobs in the US and more probing into the nature of your business, regardless of if you say you’re “visiting family”.
  • So what do you do when you re-enter Canada after 3 months of being away? I didn’t lie about it, I said I was away for 3 months because there is a clear stamp in my passport of when I entered the US. When there is evidence, you should never lie, even if the agent will most likely not check. Upon hearing I was gone for 3 months, the agent understandably looked surprised for 2 normal reasons. One, I didn’t buy anything? No, I spent it on cabs and food. Two, what were you doing there for 3 months? Traveling the west coast, and finding myself/quarter life crisis. I used the latter one coming back from a 6 month stint in India, worked perfectly.
we made it through customs!
we made it through customs!

I’ve been in every situation imaginable or my colleagues have, so I am well versed in crossing the border and all that is has to offer. The trickiest border by far for me has been the US border for obvious reasons. All others are easy, although India makes a big fuss about staying even one day over your VISA time.

The best thing to do is be confident, have a clear story as in knowing the purpose of your visit, return date and occupation. Of course you could get a business VISA, but as an entrepreneur, I don’t have the time or money to do that. 😉

Have you encountered visa issues? Do you have any tips?

4 thoughts on “Visa Hacking Your Way Across the US Border

  1. interesting post , having been to over 25+ countries , I have found its sometimes difficult to leave a country then entering !!

  2. haha well, you just need to have a convincing story and be up front with what you’re taking out..its all about being prepared. Thanks for reading!

  3. After 3 months in the US, how soon can you come back? What do you say when asked why are you back again?

  4. Good question – actually not sure how soon you can come back. After my 3 month trip, I didn’t go back till more than a year later…

    Because I had gone from SF to NYC, then took a bus to Toronto, I had minimal questions.. they tend to ask less questions when you take a bus across the border, although its such a hassle.

    I usually say I visited family and traveled, spent money on food and cabs.

    Thanks for reading, good luck!

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