For Somesh Dash, a venture capitalist in Silicon Valley, it was the time a good friend, an Israeli immigrant and entrepreneur, got booted out of the country and had to run his start-up from Vancouver.
Richard McNeel, the chairman of a chemicals business in North Carolina, remembers how a talented employee was obliged to make repeated trips to Canada to renew his U.S. visa, keeping him away from the office for months.
Ask nearly any U.S. business executive about the country's immigration system and the response is often a personal experience that demonstrates their dissatisfaction with a process they consider either creaky or broken.
Now, for the first time in decades, there is a unique chance to enact a substantive overhaul of that system – and businesses are determined not to let the opportunity slide. They're mobilizing to influence lawmakers and sway public opinion, making them a key force in what promises to be a delicate debate.
Next month, U.S. lawmakers are expected to start considering a bipartisan plan to tackle several major priorities – better border security, more visas for skilled workers, and a path to legal status for an estimated 11 million people who are living in the country illegally.
Interestingly, Canada is considered a counterpoint in the discussion, say executives and advocates, who cite it as a country that is getting immigration policy right.
"Canada is invoked a lot in this debate," said Peter Muller, director of government relations at Intel Corp. in Washington. "The people that we educate and then kick out of our country – Canada is ready and willing and interested in accepting them."
For different reasons, both of the two major U.S. political parties are keen to show progress on immigration: Democrats have long promised reform but never delivered, while Republicans want to repair their standing with Hispanic voters. Still, the path ahead is fraught with difficulty.
Among the groups agitating for broad reform is the Partnership for a New American Economy, which was founded three years ago by New York Mayor Michael Bloomberg and counts the chief executive officers of such firms as News Corp., Boeing Co., and Microsoft Corp. among its co-chairs. More than 500 CEOs and mayors from across the country have signed on to the campaign.
"When we started, we were nervous," said Jeremy Robbins, the director of the group. The worry was that only some industries – technology and agriculture, for instance – would get on board. That proved unfounded. "The reality is that it's such an enormous problem all over the spectrum," Mr. Robbins said.
The group moved quickly to showcase the economic benefits of immigration in tangible ways: one report it sponsored last year found that 40 per cent of U.S. Fortune 500 companies were founded by immigrants or their children.
The United States had better move fast to upgrade its system, Mr. Robbins added, citing Canada's recent move to introduce a visa aimed squarely at the founders of start-ups. "You're doing it in a very aggressive way to compete against America," he said. "And we see it and we know it."
The cause has gathered together executives from diverse geographies, industries and political persuasions, among them Mr. Dash in California and Mr. McNeel in North Carolina.
Mr. McNeel is the chairman of Lord Corp., a private business with more than $800-million (U.S.) in revenue that makes adhesives and mechanical parts used in aeronautics.
He describes himself as a fairly conservative Republican and began speaking out about immigration through his local chamber of commerce. He says he favours reforms not only for high-skilled workers like the kind employed by his company, but also for undocumented workers.
"It has to be addressed together," he said. "I'm hopeful. I think the Republicans got a strong message in the election."
For Mr. Dash, a principal at Institutional Venture Partners in California, the motivation to get involved in the debate was both personal and professional. His parents emigrated from India to the United States – stopping first in Canada to acquire advanced degrees – and went on to careers at technology companies.
In 2010, he had a jarring experience. Amit Aharoni, a friend and fellow graduate of Stanford University's business school, had founded an online start-up that already had 13 employees. But Mr. Aharoni's request for a new visa was rejected by U.S. authorities and he was ordered to leave the country. He went to Vancouver to stay with a friend. When the U.S. media publicized the story, the government immediately reversed its decision.
"These people are the best and the brightest," Mr. Dash said. "Rather than welcoming them and saying, 'You should stay and create jobs,' they're being tortured by the immigration system and kicked out in a few extreme cases."
Now Mr. Dash is working with the Partnership for a New American Economy to rally his fellow technology executives behind comprehensive reform. Next month they plan to inundate lawmakers with messages of support in a "virtual march" on the nation's capital.
Immigration advocates say that businesses are much more outspoken about the need for change than they've been in the past, which at times makes for some strange bedfellows.
"What we find is whether you hold a bible, you wear a badge, or you own a business, you want a common-sense solution to the immigration [issue]," said Ali Noorani, executive director at the National Immigration Forum.
Mr. Noorani spoke with The Globe and Mail by phone from a conference of venture capitalists in Boston. In such gatherings, "There's always an undercurrent of, 'Well, I can take my business to Canada, where it's a lot easier,'" he said. "It's amazing. It's in Canada's interest for America not to have a functioning immigration system."