In January 1993, an episode of The Simpsons aired in which a smooth-talking stranger in a straw hat, Lyle Lanley, arrived in Springfield with a song. The town had just come into a windfall of $3 million from a fine levied against the local nuclear plant, and the citizens were debating, at a town hall meeting, what to do with the money. Marge Simpson stood up to suggest they fix the cracked and crumbling Main Street. The crowd was unconvinced. Then Lanley took the stage and launched into a Broadway-style musical about how Springfield needed a monorail. Lanley promised modernity, glamour, and a place for the town in the ranks of Brockway, Ogdenville, and North Haverbrook as one of the great monorail towns of the American republic. The crowd, hypnotized, voted to give Lanley the money. The monorail was built but turned out to be a deathtrap, and Lanley fled to Tahiti with a suitcase full of cash. The episode became one of the most quoted in the entire run of the series, and in certain corners of the policy world it has lived on as a stand-in for any too-good-to-be-true infrastructure pitch sold to a gullible government by a charismatic outsider.

John did not understand, in 1993, why this episode mattered. But it later became an episode that reflected his purpose in life.

Childhood

John Ruffolo’s father came from southern Italy. He had grown up on a watermelon farm and was destined, if he stayed, to spend his life on that farm. His mother came from central Italy. They both left as teenagers, in the great post-war migration that brought hundreds of thousands of Italians to the cities of southern Ontario in the 1950s and 1960s, and they met not in Italy but in Toronto, in the streets of the original Little Italy. They married, and moved into the working-class suburbs absorbing the Italian community as it grew, ending up in the corridor between Jane and Sheppard and Jane and Finch. They had three children. The eldest was a brother who would eventually work for the Toronto Transit Commission; the middle was a sister who would eventually work in retail; and John, the youngest, would eventually become the outlier.

The neighbourhood was an outpost of southern and central Italy transplanted onto the Canadian Shield. The gardens in every backyard grew tomatoes, zucchini, peppers and basil. The fences between properties had small gates cut into them so that neighbours could move freely from one yard to another and trade what they had grown, one family taking the tomatoes and another the peppers. The men worked construction or in the trades. No Canadian employer in those years would hire an Italian for anything else. Many of the women never learned English, because the world they needed to survive inside a few square blocks. When John was small, he believed he lived in Italy. It took him until he was 5 to figure out he did not.

The family was of modest means. Money came in on Friday and was gone by Wednesday. They ate what they grew. They drank wine they had crushed themselves in the basement, the kids pulled in to help with the crushing, their fingers stained purple for a week afterwards in a colour that would not wash off no matter how hard it was scrubbed. In September, when the tomatoes came in, every family on the block mobilized for the great annual canning of the sauce, and John would arrive at school the next morning with tomato seeds clinging to his hair, sleeves, and collar, and the seeds would still be there a week later, dropping off one by one. He found the seeds humiliating, but the wine fingers were worse. He spent his entire childhood trying to get out from under both.

He had a vast extended family of cousins, aunts and uncles arrayed around him on every side, and within that extended family, which he describes as enormous, he was the first person ever to attend post-secondary school. The rest of the family had gone into the trades. They were tile setters, cement workers, painters, and small entrepreneurs running floor businesses or grocery stores. They were entrepreneurs not because they had chosen entrepreneurship but because the doors to salaried employment had been closed to them. From this, his parents drew the opposite lesson: do not become an entrepreneur. Do not work with your hands, do not run your own business unless you are forced to, become a professional and wear a suit and earn a salary, become a lawyer or an accountant or an engineer or a doctor. The professions, in their reading of the Canadian economy, were the only category of work that came with the credentialed legitimacy that no amount of prejudice could override. John absorbed this and accepted it.

By the time he was 6 he was reading Martin’s Criminal Code, the standard Canadian legal reference, in his bedroom, having decided he was going to be a lawyer and that the law was therefore something he should probably understand.

His father, when John would later ask him as an adult why he had left Italy if he loved Italy so much, would yell at him. “You think you would be doing what you’re doing now, enjoying your life, if I stayed there? You would have been working with me on the farm!” John would concede that this was a reasonable answer.

His earliest hero, oddly, was Pope John Paul II, not because the family was particularly devout, although they were Roman Catholic, but because the man on television was the first Pope in living memory to leave the Vatican and walk among the people, and the small boy watching from his living room recognized in this figure something he could not yet name. He would later be drawn to the Dalai Lama for the same reason. To Nelson Mandela, who walked out of 27 years in prison and refused to grow visibly angry. To Muhammad Ali, who had no formal education, became one of the great communicators of the 20th century anyway, absorbed beating after beating in the ring and beating after beating in his political life, and refused to blink. The pattern running through every figure John found himself idolizing was the pattern of the maverick, the non-conformist, the person who had been told the thing they were trying to do was impossible and went ahead and did it anyway.

The Bank at Jane and Finch

When he was 16, John got a job as a teller at the Bank of Montreal branch on the corner of Jane and Sheppard. He took it for the money and the chance to wear a tie. Within a year he had been promoted to manager, on Thursdays, Fridays and Saturdays, of the Bank of Montreal branch at Jane and Finch.

The branch at Jane and Finch was famous in Canadian banking for two superlatives, both unwanted. It had the highest number of daily transactions of any branch in the entire Bank of Montreal system, because it served a community of working-class immigrants and pensioners who came in person every day to deposit their cheques, pay their bills and send money home. It had, by a wide margin, the lowest average dollar value per transaction of any branch in the entire system, for the same reason. The neighbourhood was rough in a way that Toronto polite society did not like to acknowledge. Anyone with half a brain and any career to protect had said no when offered the job of running it, and the bank had eventually worked its way down the list to a 17 year old high school student in a borrowed suit. He said yes immediately. He did not understand he was supposed to say no. “Of course I’m going to do that,” he said years later. “I’m the naive guy.”

What he learned in that branch, in the long Saturday shifts when he was the senior person in the room and entire families would come in to argue with him in three different languages about a hold on a cheque or a bounced money order, was the entire architecture of finance from the inside out. He learned what cash flow meant when it belonged to people with no margin for error. He learned what a default looked like in person, sitting across a desk from someone whose face you knew from the church on Sunday. He learned that finance was not, fundamentally, about numbers. The numbers were trace evidence left behind by human decisions made under pressure. The way to be good at finance was to understand the people first and the numbers second. By the time he finished Grade 12, the lawyer ambition was gone, replaced by something he did not yet have a name for but that pointed in the direction of Bay Street.

He went to the Schulich School of Business at York University, which in those years was the natural destination for ambitious working-class kids from the Toronto suburbs who could not afford to look further afield. In his third year summer he was wrestling between two offers. The first was from Bank of Montreal, in what was then called corporate and government banking, the predecessor of investment banking. The second was from the Toronto office of Arthur Andersen, the great accounting and consulting firm. He could not pick. So, with the unreasonable energy of 20-year-olds, he simply did both jobs, 80 hours a week for four months, and let the firms compete for him in real time. The decision came down to a single conversation. The senior banker told him that if he stuck with the program and worked hard for twenty years he might one day occupy a position similar to the vice president’s. Twenty years sounded like the entire span of his life again. The Andersen partner, asked the same question, said the firm would let him move as fast as he wanted. There was no ceiling and no schedule, only the speed at which he himself was willing to run.

“Oh,” John thought. “I will take that.”

Arthur Andersen

What awaited him on Bay Street was a culture shock Schulich had not prepared him for. Arthur Andersen in the late 1980s was the most prestigious of the Big Five accounting firms, and its Toronto office was populated by graduates from premier private schools of the Canadian establishment, whose families had been on Bay Street for generations and knew each other already from sailing camps in Muskoka. He had never met any of these people. He had a chip on his shoulder, an Italian surname and a hairy chest. Within his first weeks at the firm a colleague walked into the men’s locker room while he was changing for a sports league and said that he must have big feet too, using a slur for Italians we will not reproduce here. In any other context John would have punched the man in the face. Instead he filed it away. He understood the kind of room he had walked into.

He moved from audit, where he had started, into tax, because tax was where the deals happened. He had developed, in his short time on Bay Street, a deep affection for the choreography of mergers and acquisitions and IPOs. By 1992, at 25, he had not yet made partner. The country was in the depths of a recession. He was bored, trained as an international tax expert, but with no transactions to do international tax on. The clients he was being handed were giving him their tax problems, and the part of the work he loved was not the tax. It was sitting across from the founders and asking them to explain how their businesses actually worked. He could do that for hours. He noticed, with some surprise, that almost no other tax person on Bay Street did it at all.

He went to the partners and asked permission to build a new practice within the firm dedicated to serving Canadian companies in a particular industry. He had thought about which industry. The banks, manufacturers, and the resource companies were obvious candidates, but the people running them were a generation older than he was, and his odds of getting a meeting with a 55-year-old CEO as a 25-year-old manager were close to zero. The technology industry, by contrast, had founders close to his own age. They would not, he reasoned, treat him like a piece of crap simply because he was 25. This turned out to be exactly correct, but the bet took years to pay off. The senior partners, who did not particularly care about technology one way or the other and who had no expectation that someone John’s age could realistically build a practice from scratch, gave him their blessing the way they gave blessings to children who want to dig for gold in the backyard. “Knock yourself out,” they said.

He had been handed two technology clients early on, Oracle and Microsoft, and from those two relationships he started knocking on the doors of every founder in Toronto who would meet with him. Total revenues for the technology practice, Year one: $0. Year two: $0. Year three: $0. He was, all the while, doing his full tax workload on top, billing the same 60 hours a week he had been billing before, because if the technology practice continued to bill nothing his only insurance against being fired was the tax revenue he kept generating on the side. He was running two careers in parallel, and he was tired.

The break came in late 1994, from an unexpected direction. A team of engineers at the National Center for Supercomputing Applications in Illinois, including a young man named Marc Andreessen, released the Mosaic browser, which they spun out into a startup called Netscape. The browser made the consumer internet visible, for the first time, to ordinary people. Within months every major company in North America was scrambling to figure out what its internet strategy was going to be. Within a year the entire landscape of business had been reorganized around a category of company that, six months earlier, had not existed. John, who had spent three years building a practice nobody at his firm believed in, was suddenly one of the only senior people at the only major accounting firm in Toronto with deep relationships across the technology industry, just as the technology industry was about to become the industry. The fees, for years a flat zero, started arriving in the millions. He was on fire and his career took off.

He remembers a partner walking up to him in this period and said, in a tone of weary congratulation, that “it must be pretty lucky how the technology thing had worked out.” He looked at the partner and thought, “Are you kidding me?! You threw me to the dogs for three years and now I’m making more money than you are and you call it luck?” Obviously, he did not say it out loud.

Partnership Shmartnership

By the autumn of 2001 he had been promoted into the global partnership of Arthur Andersen, the small inner sanctum of the firm whose members held an interest in the worldwide partnership in Switzerland, not merely in their local national practices. He was the youngest partner at the time of his elevation. There was a small administrative matter to attend to before he could take up his new seat. Becoming a global partner at Andersen required a capital contribution. Specifically, it required a personal cheque for $1 million.

The son of an Italian house painter from Jane and Finch did not have anything close to a million dollars in 2001 currency. The firm had a standing arrangement with a group of friendly lenders who would loan a new partner the buy-in amount against the security of the partnership interest itself, and so John borrowed the full seven-figures, signed it over, and walked back to his desk a global partner. Three weeks later, the news broke about a small accounting irregularity at one of Arthur Andersen’s largest clients, an energy trading company in Houston called Enron.

What followed has been chronicled in books, films and graduate school case studies. What is harder to convey is what it felt like to be a brand new global partner at the firm whose name was on top of the disaster. The Enron lawsuit was filed in the United States, where the audit work had been done, but because John had just bought into the global partnership his interest was directly exposed to the U.S. firm’s liability. There were no limited liability protections in place at the time for partnerships of this kind. If the U.S. firm was found liable for the multi-billion-dollar damages being claimed, the global partners around the world were on the hook personally, with no cap. John faced the loss of every dollar he had ever earned, the forced sale of his house, and personal bankruptcy. Bankruptcy carried with it, under the rules of the Chartered Accountants of Ontario, the automatic loss of his CPA license. Inside of nine weeks he had borrowed a million dollars he did not have, lost it on paper, and discovered he was on track to lose his career as well.

His marriage was failing at the same time. The dot-com market, which had been the engine of his rise inside the firm, had begun its long collapse the previous year and was now, with the World Trade Center attacks layered on top, in something close to free fall. The global partners voluntarily cut their incomes by two-thirds overnight. On a personal balance sheet that was already underwater this was an act not of generosity but of grim necessity. He was finished.

Instead of breaking, he moved out of his marital house and rented a room on the top floor of a home elsewhere in his old neighbourhood, kept his bicycle, went to his favourite coffee shops and bars, and had pasta at his mother’s on Sundays. After a couple of months of this he sat down with himself, in one of those coffee shops, and ran the same logic he had run at Jane and Finch. What was true was that he was alive, that he was healthy, that he could still ride a bicycle, drink a cup of coffee, and be loved by his family. The amount of income he was earning, even on one third of his previous salary, was extraordinary by the standards of the world he had grown up in. He was experiencing a first-world problem. His parents, who had crossed an ocean with nothing in their pockets, would not have recognized it as a problem at all. “If this is the worst it becomes,” he said to himself, “this is no problem.” Hope, he later said, touches the same door as despair. He chose the door of hope.

The postscript nobody saw coming was that none of the threats came true. Arthur Andersen, in the global wreckage of Enron, was rolled into Deloitte in Canada. The merger was structured so that the global partners’ liability was fully contained and never crystallized. The capital contributions were fully refunded. He got his million dollars back, kept his CPA license, and avoided bankruptcy entirely. The merger with Deloitte, which had appeared in the moment to be an act of corporate humiliation, turned out to be the slingshot that launched the second phase of his career. He arrived at Deloitte in 2002 with the half-feral instincts of an Andersen survivor and the resources of the largest accounting firm in Canada at his disposal. He had been broken almost to the point of failure and what came out the other side was a man with the confidence of someone who had already lost everything once and watched the world keep turning anyway.

Pension Funds

The Deloitte years ran from 2002 to 2010. He took over the firm’s global leadership for technology, media and telecommunications, which gave him a perch from which to observe the entire arc of the industry on every continent. He served as the personal advisor to the CEOs of Rogers, BlackBerry, and Open Text. He sat on the board of Deloitte itself.

By around 2005 he had begun to develop a worry that no amount of personal success could quiet. The dot-com crash had not really receded. It had simply settled in. Venture capital in Canada, which had never been particularly robust, had hollowed out. The domestic venture firms of the 1990s had folded or were running out of money on their final funds. The pension funds, which in any other country would have been the natural source of replacement capital, had publicly declared themselves uninterested in the asset class and were diverting their allocations into infrastructure, real estate, and private equity buyouts of mature businesses. The kids coming out of the universities were leaving for Silicon Valley at a rate that was not sustainable for any country that hoped to compete in the digital economy. Canada was on track to lose an entire industrial generation.

He decided to put his shoulder against a problem that was not strictly his problem. He spent the next three years working on public policy, advising the federal and provincial governments on what could be done to revive the venture capital ecosystem. He ran the government relations committee at the Canadian Venture Capital Association. He wrote the first draft of what would eventually become the federal Venture Capital Action Plan. He gave speeches, wrote papers, and began to publicly attack the pension funds. He attacked them in private meetings with their CEOs and CIOs, and when those meetings produced nothing he attacked them in the financial press, in industry conferences, in op-eds. He proposed a 1% pension tax, a mandatory levy that would force the large funds to contribute to a domestic innovation pool whether they wanted to or not. The pension fund executives, who had not previously considered themselves the sort of people who got attacked publicly by Bay Street accountants, did not enjoy this. They responded badly, and he kept attacking.

In late 2010 the telephone rang in his office at Deloitte. It was Michael Nobrega, the chief executive of OMERS, the Ontario Municipal Employees Retirement System, one of the five largest pension funds in Canada. John knew Nobrega from a long way back. Nobrega had been a senior partner at Arthur Andersen during the summer when John had been a tax intern there, and the two had stayed in loose touch in the decades since. The call, John assumed, was going to be a polite invitation to stop attacking pension funds in print.

It was not. Nobrega told him OMERS was thinking about getting into innovation. He asked John whether he would consider serving as an advisor to help structure the program. “Oh my god,” John said. “That’s wonderful.” Three meetings later the request had escalated. Nobrega did not want him as an advisor. Nobrega wanted him to come over and build a venture fund. “We don’t know what to do,” Nobrega said. “You have been poking us. You think you’re so smart. Why don’t you do it?” John, who was a partner on Deloitte’s national board and was being seriously considered as a future leader of the practice, found himself trying to talk Nobrega out of the offer. He laid down conditions, asking for things he assumed OMERS could not deliver, but Nobrega kept saying yes. He had run out of obstacles. With one last bit of risk mitigation he asked Deloitte to insert a clause in his resignation papers stating that if he chose to return to the firm at any point in the future he would be deemed never to have left. Deloitte agreed.

He arrived at OMERS in January of 2011. On the 1st of December, 2010, less than a month before his start date, an opinion piece appeared in the Globe and Mail. It was written by a Canadian venture capitalist in the Valley, a “friend” of John, and it argued in not particularly veiled terms that OMERS had made a catastrophic mistake by hiring John. It pointed out he had never invested capital in his life and questioned whether an accountant from Bay Street could possibly build a venture capital firm. The piece was particularly galling because John had spent the previous five years at Deloitte advising essentially every venture capital firm in Canada and several in Silicon Valley, sending them deal flow, doing diligence work for them, and feeding the author of the article in particular more business than he had probably gotten from any single source. He found out later that the author had wanted the OMERS job himself. The Globe piece was the public expression of professional resentment. He read it, then received a call from Nobrega to which he said, “John, I’ve got your back.” The chip on the shoulder, quiet for some years, came roaring back. He was going to prove every one of them wrong, in public, with money that was not his.

OMERS

The first few years at OMERS Ventures were a period of intense and largely invisible work. John and his small team focused initially on the smallest stage of the market, on companies between $0 to $10 million of revenue, because that was the segment where the lack of domestic capital was most acute. The first investment they made was in a Toronto-based company called Wave Accounting, which had built a free online accounting platform for very small businesses. Over the following decade Wave would return roughly 100x the original capital. Anyone with the guts to write a cheque in 2011 and the patience to hold the position was going to make money. What was difficult was the guts and the patience.

By 2012, with the first wave of small investments out the door, he started seeing something else move through the market. A handful of his early portfolio companies were growing far faster than he had expected, blowing through the $10 million revenue mark inside of two years and arriving at a stage where they needed a much larger cheque to keep scaling. Nobody in Canada in those years could write that cheque. The entire growth-stage segment was a desert. American firms could fly in from Boston and Silicon Valley and write the cheque, but they would extract, as the price of the capital, a significant migration of the company’s center of gravity to the United States. This would be the inevitable consequence that the eventual exit and wealth creation would happen below the border. He decided to push OMERS Ventures up the stage curve.

In the summer of 2013 there was a coffee chat that turned into the defining transaction of his career.

The man on the other side of the table was a soft-spoken German immigrant named Tobias Lutke. Tobi had moved to Ottawa in pursuit of a Canadian woman he had fallen in love with. In Ottawa he had co-founded a small online snowboard shop called Snowdevil. While trying to build the website for the shop he had become so frustrated by the available e-commerce software that he had ended up writing his own platform from scratch, in a programming language called Ruby. His friends, who came in to buy snowboards, started asking where he had gotten the website software, because they wanted to use it for their own little online businesses. Tobi pivoted away from snowboards entirely and rebuilt the company around the platform itself, which he called Shopify. By 2013 the company was growing fast and looking to raise the largest financing round in Canadian technology history, $100M.

John walked into the meeting expecting to spend half an hour on the company’s financials, growth model and competitive position. What he got instead was a 2.5 hour conversation in which the topic of Shopify, in the narrow business sense, almost never came up. Lutke talked about artisans. He talked about small businesses, about the fundamental injustice of a world in which a cabinetmaker in a small town or a leather worker in a back-alley studio could not, simply because they did not have the technical skills to build their own e-commerce platform, sell their wares to the world. He talked about why he had moved to Canada, why he loved the country. The whole conversation came out of him with the undiluted conviction of a man who had identified one particular problem and decided it was the central project of his life.

By the end of the meeting John had decided, more or less without having looked at the company’s books, that he was going to write the cheque. He went back to his team and told them he had no idea whether the software actually worked but they had to back this founder. They put the deal together. OMERS led half of the $100M. Shopify went public 20 months later, at a valuation north of a billion dollars. It has since become the largest publicly-traded company in the history of Canada and the most important wealth creation event in a generation of Canadian technology.

The single most important thing about the Shopify investment was not the software. The software was good and the market was big, but neither of those things was what mattered; what mattered was the founder. “Don’t chase the money, don’t chase the glory, don’t chase the fame,” he says. “Chase the problem. The problem will get you around every obstacle.” He came to think of his work not as financial work but as pattern recognition work. The technology underneath any given company was going to change, sometimes within months, with the market shifting alongside it and the product shifting again on top of that. What did not change was the founder’s relationship to the problem. Whether they would still be obsessed with that problem ten years later, after they had become rich and famous and had every excuse to walk away, was the only question that mattered.

Around Shopify, the OMERS Ventures portfolio filled in. There was Hopper, the Montreal-based travel booking application that used machine learning to predict flight prices; Rover, the Seattle-based marketplace for dog walking and pet sitting; Wattpad, the Toronto-based storytelling platform that grew into one of the largest reading communities in the world; DuckDuckGo, the privacy-first search engine built as a deliberate alternative to Google; League, the Toronto-based digital health benefits platform; TouchBistro, the Toronto-based point-of-sale software for restaurants; and Xanadu Quantum Technologies, the Toronto-based pioneer in photonic quantum computing. By the time he finished his run at the firm, OMERS Ventures had deployed more than $500M across more than 40 companies. In parallel, almost by accident, he had opened a co-working space at 111 Richmond Street West that became the clubhouse of the new Toronto technology scene. Founders, operators and investors collided in the hallways. The room ran on what he calls coopetition. When founders raised money or had an exit, the rest of the community cheered. They were not pretending when they cheered, and the culture he had built around that fact was the rarest thing in Canadian business.

He has, over the years, been candid about the failures alongside the successes. The pattern in the ones that did not work, looking back, is consistent. Either he had misjudged the founder’s resilience, or he had failed to be honest about a follow-on. The first failure mode was about purpose. The founders who fold under stress are not the ones who fold loudly. They are the ones who, when things get difficult, quietly say “I’ll try something easier” and pivot away from the original problem. The founders who survive are the ones who refuse to pivot away from the problem because the problem is the reason they got out of bed in the first place. The second failure mode was about ego. Venture investors, in his experience, do a reasonably good job on their first cheque into a company and a terrible job on the follow-on. The follow-on is where the ego protects itself. Investors convince themselves that doubling down is loyalty when it is in fact denial. He instituted, both at OMERS and later at Maverix, a strict policy that every follow-on had to be evaluated as if it were a brand-new investment, with no credit given to the prior conviction.

The framework underneath all of this, the larger argument that would eventually subsume the venture capital work and reorganize the rest of his life, was still missing. It arrived in 2014, in a book.

Peter Zeihan

The book was The Accidental Superpower, by an American geopolitical analyst named Peter Zeihan. Zeihan had spent the early part of his career at Stratfor, the private intelligence firm, before going independent. His method, refined across what would become a series of four books, was to start from two variables that almost no other geopolitical thinker treated as primary: geography and demography. Everything else was downstream of those two.

The argument of the book was that the United States was not a great power because of its political system, military, or culture, but because of its geography. The country sat on the largest contiguous stretch of arable temperate farmland on the planet, irrigated by the most extensive and navigable internal river system in the world. It had two ocean moats protecting it from the great powers of Eurasia, friendly neighbours to the north and south, deepwater ports on both coasts, and abundant domestic energy. The post-1945 global order had not been an act of generous statesmanship by the Americans, but a strategic bribe. The U.S. Navy would guarantee the freedom of the seas for everybody, friend or foe. The American consumer market would be opened to allied exports on extraordinarily generous terms. The U.S. dollar would become the world’s reserve currency. In exchange, the allies would line up against the Soviet Union and accept American leadership of the Western alliance. The German export miracle, the Japanese industrial revival, the rise of the Asian tigers, the Chinese manufacturing boom, all of it had been made possible by the American naval umbrella and the American consumer market. None of it would survive the unwinding of the deal, which was already underway. The Soviet Union had collapsed in 1991. There was no longer a strategic reason to bribe the rest of the world. The shale revolution, which had begun in the late 2000s, made the United States energy-independent, which meant the Americans no longer needed Middle Eastern oil. American manufacturing had been hollowed out by the very globalization Bretton Woods had made possible. The political coalition that sustained the order had collapsed at home. What was coming was a great unwinding. Long supply chains across multiple oceans only worked if somebody policed the oceans for free. Just-in-time manufacturing across continents only worked if shipping was cheap and predictable. Without the American naval umbrella, all of it would fragment. Energy markets would regionalize. Trade routes would become contested. The countries that depended on imported food and imported energy, which was most of the developed world outside North America, would find themselves vulnerable in ways they had not been since 1945.

John read the book in 2014 and something clicked. He gives, as an example, the question of which Canadian technology has produced the greatest global disorder of the 21st century. The answer, almost nobody guesses, is fracking. Fracking was developed in Canada, but was not patented or systematically commercialized. The Americans took the technology, built an entire industry around it, and used it to convert themselves from a net importer of Middle Eastern oil into a net global energy exporter, which gave them the ability to tell the rest of the world to fend for itself. One Canadian technology, never properly captured, reordered the global balance of power.

The Zeihan framework gave John a vocabulary that connected the things he had been working on as discrete problems for a decade. Capital, talent, trade rules, data, intellectual property, energy, food, and defense were not separate problems but the same problem viewed from different angles, all expressions of a single underlying question, whether a country controlled the conditions of its own economic and physical existence or had outsourced those conditions to somebody else. The word for the answer to that question was “sovereignty”. Zeihan, alongside Ian Bremmer at the Eurasia Group, whose Monday morning newsletter John’s entire team waits for and reads in full, has become 1 of 2 intellectual architects of the way the firm sees the world.

The Council

In October 2015, John and Jim Balsillie founded the Council of Canadian Innovators.

Jim, the former co-CEO of BlackBerry, had spent the years since the collapse of his company’s competitive position learning how American technology firms actually compete internationally. The lesson he came away with, and that he delivered in a speech at one of John’s CEO roundtables in 2015 that John remembers as the most important speech he ever heard, was this. When a Canadian technology company competes against an American technology company, the Canadian company is not actually competing against the American company. The Canadian company is competing against the entire United States government. American technology firms, especially the largest ones, have spent decades building lobbying and government relations infrastructure that allows them to shape the rules of the game in their favour. Trade treaties, tax legislation, intellectual property frameworks, regulatory standards, procurement policies, and antitrust enforcement. All of it is influenced, in ways that are usually invisible, by the industries it affects. The Americans do this masterfully, but the Canadians do not do it at all. Worse, the Canadian elite has developed a kind of moral self-flattery around its refusal to play this game. Canadians like to tell themselves they are above lobbying, above industrial policy, above the grubby work of writing rules in their own interest. They prefer to think of themselves as Boy Scouts in a world of free and open commerce that does not exist. They were written by American industries and American lawyers in American interests, and Canadian companies trying to scale globally are running into walls they do not even know are there.

By the time Jim finished speaking, the room of CEOs was depressed. John pulled him aside and asked what they could possibly do about it. Jim’s answer was that no individual Canadian technology company could afford the kind of government relations infrastructure American companies took for granted. A serious lobby shop costs millions a year and requires expertise Canadian founders, busy running their companies, do not have. But if the resources of 50 or 100 Canadian technology CEOs were pooled together, then it could be afforded. A single organization could be built that handled the government relations function for all of them, focused only on issues where their interests aligned, and gave them, for the first time, real political weight in Ottawa.

That was the founding insight. The Council of Canadian Innovators, with Benjamin Bergen as its first president, was built to be the shared lobbying arm of Canadian technology scale-ups, paid for entirely by member companies and answerable only to them. The membership criteria were narrow and deliberate. To join, a member had to be Canadian-headquartered, in the technology sector broadly defined, and generating meaningful revenue, and the narrowness of those criteria was the point. Jim and John did not want a generic business association diluted by the priorities of the banks and the telcos. They wanted a focused organization representing the specific interests of the people building the next generation of Canadian technology companies, because those interests were systematically underrepresented in Ottawa.

The substantive policy agenda has clustered around three themes John summarizes as access to capital, access to talent, and access to markets and customers. On capital, the Council has spent a decade hammering on the same point John was making in 2010, that Canadian pension funds and Canadian banks systematically underinvest in Canadian innovation. On talent, the Council has been deeply involved in immigration policy, particularly in pushing for fast-tracked visas for highly skilled technology workers; the federal Global Talent Stream programme, one of the rare unambiguous successes of recent Canadian industrial policy, was shaped in significant part by Council advocacy. On markets, the Council has fought a long and largely losing battle against Canadian government procurement practices that systematically favour American technology vendors over Canadian ones. The federal government, despite years of nominal commitments to “buying Canadian,” continues to spend the vast majority of its technology budget with American hyperscalers and American software vendors. The Council has argued, with John as one of its most public voices, that this is a sovereignty issue as well as an industrial policy one. Canadian government data sitting on American cloud infrastructure is subject to the U.S. CLOUD Act, which gives American courts the right to subpoena it without notifying the Canadian government. The Council has been making this argument since before most Canadian politicians had heard of the CLOUD Act, and it kept making it through every data sovereignty fight of the last decade.

What makes the Council distinctive, and what John keeps emphasizing, is its operating posture. Most Canadian business associations approach Ottawa as adversaries, criticizing government from outside and demanding things. The Council, by design, embedded itself inside the policy process. Its staff includes former civil servants and former political staffers from multiple parties. Its members brief Ministers and Deputy Ministers regularly. When the federal government needs to understand a technical issue affecting the technology sector, the Council is often the first call. When Silicon Valley Bank collapsed in March 2023 and threatened the cash positions of dozens of Canadian technology companies overnight, the Council was already advising the federal Department of Finance and the deputy prime minister’s office before most other industry groups had figured out what was happening. John tells this story with measured pride. Being inside the room, having earned access through 10 years of consistent technically credible engagement, is more valuable than being outside the room complaining.

Two years after the Council’s founding, the test case arrived. It came dressed as Lyle Lanley’s song.

Sidewalk Labs

In 2017 Waterfront Toronto, a tri-government agency representing the federal, provincial, and municipal governments, announced that a subsidiary of Google called Sidewalk Labs had won a competition to develop a 12-acre site on Toronto’s eastern waterfront called Quayside. Sidewalk Labs was run by Dan Doctoroff, the former deputy mayor of New York under Bloomberg, and was sold to the public as a kind of urban innovation laboratory. The vision, as marketed, was the world’s first truly smart city neighbourhood, built from the internet up. Sensors everywhere, adaptive traffic signals, heated sidewalks, modular buildings, autonomous vehicles, pneumatic waste collection. A digital layer running underneath the physical one, capturing data on every movement and interaction in the neighbourhood and using that data to optimize services in real time. The pitch promised hundreds of millions of dollars of investment, thousands of jobs, and a showcase development that would put Toronto on the map alongside Singapore and Songdo.

When John first read the proposal, he thought of The Simpsons. He thought of Lyle Lanley, his song, the moving sidewalks Sidewalk Labs had literally promised, and how Springfield’s monorail was going to be the talk of the country.

Jim had been seeing it longer than John, arguing for years that Google’s actual business model was not advertising. Google’s actual business model was the extraction of economic rents from any digital surface it could control. Search, email, mobile operating systems, app stores, mapping. In every domain Google entered, it positioned itself as the toll booth between the user and the service. Sidewalk Labs, in Jim’s reading, was an attempt to extend this model from the digital world into the physical one. Cities were the next surface. Whoever owned the data layer of a neighbourhood would own the neighbourhood. They would extract a toll on every movement, transaction, and interaction. They would capture the value of the autonomous vehicle revolution by owning the data on which autonomous vehicles depended. They would relegate Canadian innovators to the role of app developers in someone else’s app store, treading water on whatever crumbs were left over after the toll had been collected. The smart city, properly understood, was a platform owned by Google, and Canada was about to give them a Canadian neighbourhood as a free testbed for technology Google would then deploy globally.

John listened and ran the math. Through Maverix, he invested in a Kitchener-based intelligent traffic systems company called Miovision, which does exactly the kind of work Sidewalk Labs was proposing to capture. He understood, from Miovision’s perspective, what was at stake. Whoever owned the data on traffic flows in a city owned the foundation layer for autonomous vehicles. Whoever owned the foundation layer for autonomous vehicles owned a multi-trillion-dollar future industry. Sidewalk Labs was not asking for permission to build a neighbourhood. They were asking for permission to build the data platform on which the entire future of urban mobility would run, and they were asking for it, in exchange for a few hundred jobs and a press release, on the cheap.

John did something almost nobody else thought to do. He bid against them, putting together a competing proposal for the Quayside site, and came in as the runner-up. He had not actually expected to win; he was bidding to verify, from inside the process, whether Jim was right. From inside the process, he confirmed that Jim was indeed right. The deal as structured was a transfer of sovereignty over data, taxation, and regulatory authority from a Canadian government to an American corporation, dressed up as an investment.

He and Jim went to war. They wrote op-eds, briefed members of Parliament, and appeared on every panel and every podcast that would have them. The deal as proposed, they argued, would give Sidewalk Labs the right to capture portions of property tax revenue to fund its own infrastructure, which they called, accurately, privatized taxation. It would give Sidewalk Labs intellectual property rights over systems developed using Canadian public data. And it would let Sidewalk Labs design its own governance structures, granting the company quasi-governmental powers over a piece of Canadian sovereign territory, with limited accountability to elected officials. Sidewalk Labs and its allies fought back. They lobbied OMERS, where John was still working at the time, to pressure him into shutting up. He did not shut up.

At one point during this period, Eric Schmidt, the executive chairman of Google, flew to Toronto and asked for a meeting at John’s office. John remembers thinking, “Who am I? I am a nobody. Why is Eric Schmidt flying to Toronto to meet me for an hour?” Schmidt arrived. The meeting lasted for 57 minutes, and the two men had what John describes as a genuinely fascinating conversation about geopolitics, technology, and the long arc of where the world was heading. Schmidt was a brilliant man. They liked each other, and John was fairly impressed. In the last 3 minutes, Schmidt took out a business card, scratched out the corporate phone number, wrote his personal mobile on the back, slid the card across the desk, and said, “If you have any issue with Sidewalk Labs, I want you to call me. I’ll resolve it for you.’ Then Schmidt got up and left, and John sat at his desk holding the card. The card was not a gift but an instruction to stop. He doubled down.

The deal slowly fell apart over 2019 as the public scrutiny intensified. Sidewalk had to keep retreating from its initial proposals, with the footprint shrinking, the IP claims softening, and the governance structure repeatedly revised. Critics that John and Jim had emboldened, including the open government advocate Bianca Wylie and the former Information and Privacy Commissioner of Ontario, Ann Cavoukian, kept the pressure on. By early 2020 the project was on life support, and in May of 2020 Sidewalk Labs announced it was pulling out of Toronto entirely. They blamed Covid-19, but almost nobody believed them. The public opposition had made the original deal undeliverable, and the revised version was no longer interesting enough to Google to be worth the fight. A year later Google wound down Sidewalk Labs as a standalone company entirely.

John asks, in the years since, a single question of anyone who still thinks Sidewalk Labs was a good idea Toronto should have embraced. “How many other cities in the world are currently doing what Sidewalk Labs was proposing here? How many other cities partnered with them after Toronto turned them down? The answer is none. Zero.” San Francisco refused. New York refused. Hudson Yards, the original American testbed, refused. Every other city in the world had looked at the proposal and said no. Toronto, alone among the great cities of the developed world, had looked at it and said yes. “We were the only idiots,” he says, and he means it as a compliment to no one. The lesson is the lesson of the monorail. When the smooth-talking stranger arrives in town with a song and a straw hat, the question is not whether the song is catchy. The question is why no other town in the country has bought what he is selling. If you are the only buyer in the world for a deal that sounds too good to be true, you are not getting a deal. You are getting played. Canadians, in his reading, have been getting played for 70 years and have developed an emotional attachment to the experience that they are only now beginning to question.

Maverix

By 2017, John could see that the problem he had originally come to OMERS to solve had been only partially addressed. He had built a firm capable of getting Canadian companies from $0 to $10 million of revenue. He had built a firm capable of getting them from $10 million to $100 million. But the third problem, the one that was now staring him in the face as Shopify and its peers approached the next stage of scale, was the problem of getting Canadian technology companies from a $100 million of revenue to $1 billion and beyond. There was, again, no one in Canada writing the cheques required to do that work. Whatever was going to fill the gap was going to need to be built from scratch.

He went to OMERS leadership and proposed building exactly that, a growth private equity practice within the OMERS umbrella that would write $100 million cheques into Canadian technology companies at the late growth stage. He got approval, and started hiring a team. And then, almost immediately, the institutional politics that he had managed to avoid for the better part of a decade began to bite. The traditional private equity team at OMERS started asking why he was building something so close to its territory. The venture team, which had been his own creation, started asking why he was scaling above his lane. He found himself squeezed between two larger and more entrenched groups inside the same institution, and as 2018 wore on it became increasingly clear to him that the political ceiling he was operating under was not going to lift. The firm he was trying to build inside OMERS was, in essence, the firm he wanted to build period. At the end of 2018 he left.

In a single week in early January of 2019 he wrote the white paper that would become the founding document of Maverix Private Equity. The thesis was Zeihan-shaped from beginning to end. The world was about to enter a great unwinding. Globalization, as it had existed since 1945, would fragment. The countries that controlled the conditions of their own existence would do well; the countries that had outsourced those conditions to others would not. Maverix would invest in the industries Canada needed to control, defined as health and wellness, financial services, transportation and logistics, live-work-play-and-learn, and retail. Technology was no longer a sector. Technology was something every traditional industry was about to be either rebuilt around or replaced by. The right play was not to invest in technology companies. The right play was to invest in the operators of traditional industries who understood how to weaponize technology against incumbents. Viral Nation, the Toronto-based social media influencer platform that became the firm’s first investment, was the proof point. Marketing business at the core, technology business in the architecture, growing globally, headquartered in Canada.

The name of the firm came from a small accident of the early days of the fundraise. The first three people who returned his calls after he announced his departure from OMERS each asked, in slightly different ways, how he had managed to last inside such a large institution. They asked it in a tone that suggested they were surprised he had stayed 8 years. By the third call he had figured out what they were getting at. He was, in their telling, a maverick, and mavericks did not last inside large institutions. He hung up the phone, looked across the room at the lawyer he was working with on the fund’s incorporation, and told her they had just figured out the name of the firm.

He went out to fundraise in early 2019 with a target of US$500M. He landed it within three months. Three months later, the lead investor reneged on his commitment for reasons that John found infuriating and that he was never quite able to forgive. He had to start the second half of the raise from scratch. By October of 2019 he had two new co-leads in place and a closing date set for the spring of 2020. The closing date was March of 2020. The pandemic shut down the process the same week. He waited. He waited some more. The pension fund partners began to come back to the table in late summer of 2020. They set a new closing date for October. He breathed, and went back to his bicycle.

Pickering Town Line

The bicycle, for John, was both a hobby and a refuge. He had been a serious cyclist for most of a decade, riding several days a week, training his upper body in a way that most cyclists do not because he liked to climb hills and he wanted the power. He did not, as a general rule, like to ride inside the city of Toronto. He thought Toronto was a dangerous city for cyclists, and he had long ago developed a route that allowed him to slip out of the urban core as efficiently as possible and into the safer roads of York Region. During the pandemic, with the rest of his social life on hold and his fundraising in suspended animation, the cycling had grown into a kind of midweek meditation. He was in the best physical shape of his life. He weighed about 200 pounds. He had powerful legs and an unusually strong upper body. He rode 4 or 5 days a week. The route from his house in the Beaches to the small town of Stouffville, north-east of the city, was about a 100 kilometres in a loop, and on Wednesdays in the summer of 2020 he was riding it almost without fail.

On Wednesday, the second of September, 2020, it was a beautiful day. He left his house in the late morning. He felt, by his own account, on top of the world. The fund was about to close. The political winds were shifting in his favour. The investors were lined up. He pedaled north out of the city along his usual back-road route, came out into the country, and turned east on Pickering Town Line, a quiet two-lane road that ran straight through the farmland a few kilometres south of Stouffville. He had ridden this stretch a hundred times. He was about 45 kilometres into the ride, 5 kilometres from his customary coffee stop in the small downtown of Stouffville.

What he heard, very clearly, with no warning, was the squealing of air brakes from a tractor-trailer directly behind his left ear.

His first reaction, in the half-second that he had to react, was anger. He assumed, on the basis of a hundred prior incidents, that some idiot truck driver was riding right on his back tire to scare him, and he was preparing to get off the bike and confront the man. But, he did not have time to confront anyone. The truck, a flatbed eighteen-wheeler whose driver had apparently been looking at his phone, hit him in the back at roughly 90 kilometres an hour. The bike was destroyed instantly. Two metal road signs anchored in concrete six feet off the road were taken cleanly out of the ground by the trailer as it jackknifed. He flew through the air, landing on the right side of his body. He did not break a single bone in his arms or in his legs, but broke, in multiple places, every single rib on the right side of his chest, in a pattern that doctors call a flail, in which a section of the rib cage separates from the rest of the chest and moves in the opposite direction during breathing, which is supposed to make survival, on its own, almost impossible. He shattered his pelvis into six pieces in what is called an open book fracture. He shattered the T12 vertebra in his lower spine, severing the connection to the lower half of his body. He tore his liver and his spleen, devascularised one of his kidneys, with both of his lungs collapsing. He lost approximately 50% of the blood in his body onto the asphalt.

He should have died on impact. Every doctor who later read his file said the same thing. He should have died on impact, and if he had not died on impact he should have died of suffocation in the first few minutes from the flail chest, and if he had somehow survived that he should have died of blood loss before any ambulance could possibly reach him. None of these things happened. He woke up on the road, two minutes after the collision, with traffic stopped around him and bystanders certain that he was already dead, and the first thing he did, with the practiced reflex of a man who had been in cycling accidents before, was to wiggle his fingers and his toes. The fingers worked, but the toes did not. He understood, in that moment, that he was paralysed. The second thing that came into his mind was that his life, in the broader sense, had been a good one, and that it would be acceptable to die on this road, in the country, doing something he loved. The third thing that came into his mind was the faces of his two children. His son was 14, and his daughter 11. He thought, “there is no way I am going to let my kids find out their dad died like this.” He tried to push himself up.

The ambulance ride to Sunnybrook Hospital in north Toronto took about 25 minutes. The paramedics could not airlift him because they had less than an hour to get him to a trauma surgeon and ground transport was, perversely, faster. He was conscious for the entire ride, on a stretcher that was not designed to be a bed, with his back broken and his spinal cord exposed, feeling every single bump in the pavement. He apologised in advance to the paramedic riding with him for the language he was about to use. The paramedic told him to swear away. He swore through the entire ride. The last thing he saw, as they wheeled him through the doors of the Sunnybrook emergency department, was the sign for the trauma unit. Then they put a mask on him and he was gone.

The surgery that followed took 15 hours and could not be performed for the first 36 hours after his arrival, because the doctors believed that a third major trauma on top of the injuries he had sustained on the road and on impact would kill him on the operating table. They waited, and told his wife, Carryn, that they wanted him to die peacefully if he was going to die. He did not die, and after 36 hours they took him into the operating theatre and worked on him through the night, rotating his body on a kind of surgical rotisserie to repair the front and back of his pelvis with screws and titanium rods and to fuse the lower part of his spine to his pelvis. He was in a medically induced coma for 6 days afterwards.

While he was in the coma the strangest thing in this entire story happened. Carryn had brought a pair of headphones to the hospital and was playing recordings into his ears, on the theory that some part of him might hear and might find the sound comforting. The recordings included Andrea Bocelli, the great Italian tenor whose voice, in the world of John’s parents, was the closest thing to a national treasure. John, lucid in some half-conscious way that has never been fully understood, heard the music. He saw white light, the way people in near-death experiences are reported to see white light. He saw, in the white light, what he understood to be a stage, and he heard Bocelli singing and an audience clapping. He understood that he was being welcomed into heaven by the angels, that the angels were Italian, and that they were applauding their countryman. The boy from Jane and Sheppard was getting a fitting send-off. He was sad about leaving his children. He was at peace about everything else. When he woke from the coma several days later and told his wife about the vision, half-laughing at himself, she stared at him and told him about the headphones.

Eight days after the accident, when the breathing tube had been removed and he could speak, the doctors came in to deliver the formal diagnosis. ASIAA Complete. The most severe category of spinal cord injury. He would never walk again. He cried for somewhere between 15 to 20 seconds, then stopped crying, and looked at the doctors and at his wife and said, in the single most characteristic sentence of his entire life, that they were not going to tell him what he was or was not going to do. He was going to walk again, and would not be told otherwise.

Six weeks into his four-month stay at the rehabilitation hospital, lying flat on his back, John picked up a telephone and resumed his fundraising for Maverix. He called the pension funds, family offices, and the institutional investors who had been on track to close the fund in October. They picked up the phone, in many cases, having not yet heard about what had happened to him, and they would chat for 10 or 15 minutes about the markets and the deal pipeline before some of them would pause and ask, with a confused tone, where exactly he was calling from. He would tell them. They would ask if he was on his back in a hospital bed. He would say yes. They would tell him to please, please, take care of his health, and that they were not going anywhere, and that the fund would be there when he was ready. Every single one of them honoured that commitment. The fund closed in April of 2021, at $500M, the largest first-time fund ever raised in Canadian history, raised in significant part from a hospital bed by a man who had been declared dead at the scene of his accident.

He went home for Christmas that year, on December 23rd of 2020, against the advice of his doctors. He sat at his kitchen table with his wife and his two children and explained to them, gently, that their father had nearly died, that the doctors had not expected him to survive, and that there was a version of the story in which he was not there for that dinner. The children, who had lived through a long parade of his prior cycling accidents and had become casually accustomed to their father bouncing back from catastrophe, looked at him and said that they had never thought he was going to die. They had seen him through too many incidents already. He was the cockroach. “Could someone,” his son asked, “pass the potatoes.”

In the years since, he has put in 20 hours a week of physiotherapy, every week, without exception, for 5 consecutive years and counting. He has cycled more than 3,000 kilometres a year on a recumbent bicycle that allows him to clip his feet into the pedals. He has walked, with a walker and then with two poles, distances that the original team of doctors at Sunnybrook believed were medically impossible and have, since seeing him do it, openly admitted they do not understand. He has raised, through his cycling team Les Domestique, more than $25 million for spinal cord and brain injury research. He has joined the board of a Canadian biotechnology company called NervGen Pharma, currently in late-stage human trials of what may turn out to be one of the most significant treatments for spinal cord injury, multiple sclerosis, and several other diseases of the central nervous system in the modern history of medicine.

Today

It is 2026. He is close to 40 years in this work, and he is not getting younger. Maverix has made its first investments and is doing exactly what he built it to do, writing large cheques into operators of traditional industries who understand technology, in the sectors he believes Canada most urgently needs to control. The thesis he started writing in 2019 has, in the years since, been violently confirmed. Globalization is fragmenting, supply chains are shortening, and energy markets are regionalizing. The American posture toward Canada has, against every expectation of every Canadian politician of the post-1945 era, turned actively hostile. The Trump administration is treating Canada not as a partner inside the fortress but as a potential vassal outside of it. The Fortress North America scenario John and Zeihan had originally expected, in which Canada would be the junior partner inside the American security and economic perimeter, is no longer the base case. The base case is something more dangerous, and the timeline for building Canadian sovereign capability across food, energy, defence, money, and data has compressed from decades to years.

He has views on what should be done. He has them in detail and he will share them at length to anyone who asks. The pension funds, which he has been hammering for 20 years, remain his single biggest target. Their argument that they should invest globally rather than domestically is, in his reading, a category error. The whole reason they exist on the favourable taxation terms they enjoy is that they are creatures of Canadian public policy, sustained by tax expenditures borne by Canadian taxpayers. Their refusal to allocate even a small fraction of their assets to Canadian risk-based investment, while they happily fund SpaceX and pass on Kepler, is not just bad investing. It is a betrayal of the institutional logic that allowed them to exist in the first place.

At the same time, the federal government continues to spend the vast majority of its technology budget with American hyperscalers, on infrastructure subject to the U.S. CLOUD Act, which means the United States government can compel the disclosure of Canadian government data without notifying the Canadian government. He warned about this for years before any politician understood what he was talking about. In June of 2025 the president of Microsoft, Brad Smith, said publicly in France that Microsoft would sue the U.S. government if it tried to compel data of European customers under the Act. Smith confirmed, in effect, that the Act worked the way John had been saying it worked. John forwarded the clip to every Canadian official he had ever briefed. They had not believed him before, but had to believe him now.

Currently. the artificial intelligence question is the sovereignty question of the moment. In the rule-of-three logic he believes governs the digital economy, three players will eventually capture most of the value in any given category. There will be three foundational large language model providers, three hyperscaler clouds and three dominant chipmakers. The Canadian question is not whether to regulate artificial intelligence, but whether to be a price taker on infrastructure provided by foreign incumbents, or to identify the choke points in the AI supply chain where Canada has genuine native capability and to invest aggressively in those choke points. Photonics is one such choke point. Canada is one of three countries in the world capable of producing the photonic chipsets that drive the next generation of high-throughput computing and satellite data transmission. The other two are Taiwan and the Netherlands. Most Canadians, including most of the Canadian government, do not know this and he is trying to fix that. Quantum computing, in the photonic variant pioneered by Xanadu, is another choke point. Defence technologies, where Maverix has been building a thesis around dual-use capability, is a third. Energy, where Canada’s geographic endowment is unmatched and where the country has spent 50 years systematically refusing to capture the value of its own resources, is a fourth. The list is short, the time is short, and the political will is, for the first time in his career, beginning to materialize in pieces. Mark Carney’s senior team, he allows, is starting to understand the problem. There is, he says, 99% more to go.

What he does not allow, in any conversation, is the line that Canadian sovereignty is somehow incompatible with foreign investment, or that the argument is protectionist. Foreign capital is welcome, with the condition that the rules of engagement are written by Canadians for Canadian benefit, and that the structures of the investments preserve, rather than transfer, the ownership of intellectual property. The battery plant deal that committed $13 billion of Canadian taxpayer subsidy to a foreign-owned facility in exchange for a thousand jobs is, in his reading, exactly the wrong template. Such an amount deployed into Canadian-owned innovation, even at the very high failure rates of venture capital, would create perpetual wealth creation machines, but deploying into a foreign-owned battery plant creates a thousand jobs and a press release. The choice between the two templates is the choice between sovereignty and dependence. Canadians have been choosing dependence on autopilot for half a century, and he is trying, with the time he has left, to persuade them to make a different choice.

He worries, more than he ever expected to worry, about his own children. They are 17 and 20 now. They are starting to talk, the way ambitious young Canadians have been talking for two generations, about going to the United States. He does not want to stop them. He wants them to see the world, study where they want to study. What he wants is for them to come back. He has never, until recently, worried that they would not. He worries now.

He has been knighted by the President of Italy, and holds the title Cavaliere. He has one foot in Italy, and is connected enough to its institutions that he could, if he chose, build a life there. He does not choose to. He was born in Canada, and he will die in Canada. The argument he has been making for 34 years is, in the end, an argument about whether the country he was born in will still exist, in any meaningful sense, when his children’s children are old enough to have the conversation about whether to stay.

His extended Italian family went into the trades because every other door was closed. They built businesses because they had no choice. They lived in a cocoon at Jane and Sheppard because the cocoon was the only place that was safe. Every generation since has had more options than the last, and the boy who once spent his entire adolescence trying to escape the cocoon is now, 60, trying to build a national version of it, a structure of capital and rules and institutions that gives Canadian founders the same protected ground his parents’ generation gave him without ever knowing they were giving it. He would not call it that. He would call it sovereignty. They would have called it home.

The Lyle Lanleys keep arriving in Springfield with their songs and their straw hats. Most of the time they win. Sometimes, when somebody in the crowd is paying close enough attention to see the thing for what it is and is willing to take the personal cost of standing up and saying so, they lose.

He intends to be in the room when they come.

He is, as he was always going to be, a maverick.

In the late 1990s, in a French-language elementary school on the western edge of the Montérégie, Andrew Lockhead was a gangly boy who never seemed to know where to put his hands. In a classroom full of Tremblays and Bélangers, his name didn’t even sound like a name. He was the mid-year transfer kid with hair pressed flat and glasses so thick they magnified his eyes into wide, unblinking saucers. Fond de bouteille, he’d call them later, coke-bottle lenses. In his first months at the school, he broke them so often that his mother kept a spare pair in the glove compartment, a permanent fixture for the drives she made every few days to the optician.

But before that, there had been Montreal, where Andrew was born in 1987. His father, Pierre Lockhead, held two jobs. One was as a cashier at the Montreal Blue Bonnets Raceway, a horse racing track, where he sat behind the glass of a betting window for full shifts while men pushed 20 cents under the slot, asking for tickets on horses they had picked out of dog-eared programs. His second job was as a mechanic on the floor of a car shop somewhere else in the city, working for someone else. His mother also worked, which meant the daycare Andrew shared with his younger brother sat in the basement of a Catholic church.

The decision to leave Montreal came from both parents, but for different reasons. His mother had begun to worry about her sons’ French. The elementary school they attended in their Montreal neighbourhood had only two children in Andrew’s class who spoke French at home. While she liked the exposure to other languages, she decided her boys were not going to grow up in a Quebec where they could not hold a conversation in their mother tongue. His father had decided that the racetrack window and the back room of someone else’s garage were the last jobs he was going to work for a boss. He had been thinking about it for years. He and a partner bought into a franchise of a Quebec car window repair chain, signed the paperwork on a unit in the West Island, and packed up the apartment. The family moved to Pincourt in the autumn of 1993.

Window Repair Shop

Montreal to Pincourt is a short 20-minute drive on the highway if traffic is moving. In the early ‘90s, it was suburban, quiet, and still small enough that the new subdivisions ended in farm fields and the elementary schools sat on lots big enough to play soccer behind. Andrew’s father opened the first garage and it did really well. Within a few years, he had opened a second one, then a third, then a fourth, scattered across the West Island and the eastern side of the island of Montreal.

The family’s life began to change in ways that were measurable at the level of materialism. Andrew’s younger brother went to private school, his father bought a car that started on the first turn of the key, and they began going on vacation. His mother stopped working outside the home and became the headhome, the role of a Quebec stay-at-home mother who had effectively been promoted into the operations manager of the household. She drove the boys to school in the mornings, packed their snacks, made dinner, and drove Andrew, every two or three days, to the optician.

The trips to the optician started almost as soon as Andrew arrived at the new school. The pair of glasses he was wearing the day he started would rarely be the pair he was wearing the next week. The frame would come back bent at an angle his father could not straighten by hand, with a lens cracked, or with the bridge snapped clean in half. His mother kept a spare pair of glasses in the glove compartment of her car for the inevitable moment, which arrived several times a week, when she had to drive him from school back to the strip mall off the main road. The optician there had come to know the family by name. He performed the repairs, usually temporary ones that would hold the frames together until Thursday or Friday, at which point Andrew would be back in the chair waiting for the next adjustment.

The protector in the family was Andrew’s brother, who was two years younger and built closer to the ground. He could absorb a hit and keep walking in a way Andrew never could. When Andrew was 9 and coming home with broken glasses every other day, his brother was 7, and he was usually the one who stepped in and stopped the fights before Andrew even had to be in them. He is a firefighter in Montreal today, continuing to protect the innocent.

The fights eased toward the end of Andrew’s second year at the new school, and the easing happened without any single triggering event Andrew can remember. There is no scene in his telling where he stood up to the lead bully, won a fight, or said the right thing at the right moment. The fights simply slowed down as other targets emerged in the schoolyard. His glasses would still break and his mother still drove him to the optician, but the frequency went from several times a week to several times a month, which was by the standards of the household at that point, an enormous improvement.

He was around 10 when his father first brought him out to the garage to work on a Saturday morning. His brother came along too. The Saturday-morning trips would continue, in one form or another, for most of the next decade of Andrew’s childhood. However, there was no pay attached. His father had decided early on that a trade was not something to be learned for a wage. The boys were there to learn, and the money, if it came, would come later. They were not paid for the first four years.

The garage itself was a single-story franchise unit on the edge of a service road off Highways 20 and 40, with two service bays at the back and a small customer waiting area at the front. The smell of the place, the same in every garage Andrew’s father would later open, was the smell of motor oil, burnt drip-coffee, and the rubber of new tires waiting in the corner. There was a counter at the front, and behind that was a glass partition through which the customer could see the bays where the cars sat on the lifts. Andrew and his brother spent most of their Saturdays in the front. They stood behind the counter, handling customers, taking phone calls, writing up estimates, and walking buyers through the catalog of windshields and radios.

The back part of the garage, unfortunately, was something his father could not seem to master. The mechanics his father employed in those years were, by Andrew’s account, poorly paid and poorly trained. He had pieced together this picture from what his father said about them at home and from what he could see on Saturday mornings, when the previous day’s unfinished work was still sitting in the bays. They would routinely fail to show up on Fridays after spending Thursday night drinking the previous week’s wages, shouting at customers when his father stepped away from the front counter, and taking longer on simple repairs than the work actually required.

The lesson Andrew took from those Saturdays was that the front and the back of a small business were not the same operation. The front was where leadership lived and where outcomes could be shaped. The back was where culture either worked for the owner or against, and in his father’s particular industry, the back was a labour pool his father could not change no matter what he did at the counter. By the time he was a teenager, he had decided that whatever business he eventually built would not have a back like that.

StudentSphere

The decision to leave the French school system for an English-language CEGEP was made in a series of conversations with his parents and a career counselor over the months before he turned 18. His father wanted him to come into the family business once he finished school. The counselor told him that the best thing he could do before joining anything was to get a credential that would not close any doors for him later. His father agreed. The question then became which institution to attend, and Andrew chose John Abbott College, the English-language CEGEP in the West Island. The practical reason was that he could not speak English and was going to need it for any business career the counselor wanted him to keep the door open for. The less practical reason was that John Abbott was a place where almost nobody he had grown up with would be enrolled. Out of his entire French high school, only one other student had decided to go. The idea of arriving somewhere where nobody knew him was the kind of fresh start his elementary-school self would have wept with relief to see coming.

The glasses came off the summer before he started at John Abbott. The standard medical advice for laser-correction surgery in those years was to wait until the patient was at least in his 20s, but Andrew’s prescription was bad enough that the surgeon was willing to take him on early, and his father had a contact through the garage who could get him into a private clinic. His father wrote a check for $12,000 and told his son to be at the clinic in the morning. The procedure worked. Andrew arrived at John Abbott orientation a few weeks later without the glasses, presenting a face that the kids he had grown up with would not have immediately recognized at a distance.

His first English class was humanities. He sat down at his desk. The teacher began to speak, and Andrew, who had not spoken English to anyone in his life beyond a few phrases of broken classroom translation, watched the teacher’s mouth move and understood almost nothing. The other students were opening their textbooks and writing notes, but he had no idea what they were writing. He sat through the rest of the class with his hands flat on the desk in front of him and asked himself, in French, what he had just done to his own life.

He waited for the bell to ring and the room to empty, then walked up to the teacher and explained, in French, that he could not follow. The teacher did not speak French. They communicated through hand gestures and broken phrases, eventually arriving at an arrangement: Andrew would come find the professor before every exam and during office hours to work through the material together, line by line, until he understood enough of it to write the test. He did this with every class he took for the first semester, and eventually graduated on the dean’s list.

He applied to every business school in Montreal after John Abbott. McGill rejected him. The John Molson School of Business at Concordia rejected him. HEC rejected him. The only school that accepted his application was ESG-UQAM, the management school at the Université du Québec à Montréal. Andrew was missing a math credit from his time at John Abbott, and ESG-UQAM was the only school willing to admit him, on the condition that he take the missing course as a remedial requirement during his first year. He took the offer. The commute from his parents’ house in Pincourt to the downtown UQAM campus was a 1.5 hours each way on the highway and the metro, which meant that on days he had a full class load, he was on the road for three hours and in the classroom for three more. He kept his grades up. He also began looking with an intensity for something to do with the hours he was spending in the city that were not the hours he was spending in the classroom.

The first day of his first frosh week at UQAM, at a beach party the business student association had organized on an island in the Saint Lawrence, he saw a man standing at the grill flipping burgers with a walkie-talkie clipped to his belt, clearly the person in charge. Andrew watched the man for some time. Then he walked up to him, with a confidence that had not previously appeared in any other domain of his life, and told him plainly that he was going to do his job in two years.

Three years later, Andrew was the president of the student association of his faculty, an organization with roughly 12,000 members, a budget of $2.5 million, a coffee shop, a career center, and an annual calendar of events that included regularly booking Metropolis, a Montreal venue with a capacity of 2,500. He took over the events portfolio in his second year, before he took the presidency, and the first major event he ran almost broke him. A week before the show, which he had personally guaranteed against the association’s budget, they had sold almost no tickets. He went home on the Sunday night before the event certain that on Friday, he was going to be the youngest student association officer in the history of UQAM to bankrupt his union. Andrew worked 15+ hours every day of that week promoting the event, until he could sell every ticket he possibly had. The show went off as the biggest party UQAM ran that academic year. Andrew sat in the dressing room afterward with the production crew and understood for the first time what kind of work he wanted to spend his life doing.

He also got dragged through two strikes during his time at the association. The bigger of the two grew out of the 2012 Quebec tuition fight, in which the provincial government had proposed an increase to post-secondary fees and the Quebec federation of student unions, the FEUQ, had called the universities into the streets. The students Andrew represented at his business faculty were mostly opposed to the strike. They were going to pay their own way through school, so the increase did not register to them as an existential threat, and most preferred to keep going to class rather than spend a semester on the picket line. The other faculties at UQAM saw it differently. Strikers from sociology and political science came into the business school building and tried to disrupt classes. They formed lines outside the doors of his faculty’s lecture halls. The police got involved. Andrew, 24 years old, spent that semester in a series of negotiations he had not expected to be conducting, with student leaders from the other faculties, with the university administration, and with his own membership. He treats the experience now as the closest thing to running a real business that an unpaid undergraduate job could have given him. He had to manage stakeholders whose interests did not align. He had to figure out what each of them actually wanted, which was sometimes power, sometimes recognition, and sometimes a line on a resume they could use to apply for jobs later, and he had to lead them on that basis.

The pain point that produced his first real company was something he had been living with every week of his presidency. To sell tickets to events his association ran, he had to stand in the corridors of UQAM at 8 a.m. with a cash box, calling out to students walking past, taking bills, making change, and counting receipts at the end of the day. Ticketmaster did not serve the student market in 2012. Eventbrite had launched but had not made it deeply into Quebec. Andrew and a friend from university decided to build the platform themselves. They called it Sphère Étudiante, also known as StudentSphere. They put in $5,000 each and received a small grant from Fondation Montréal Inc, the foundation now known as Bonjour Startup Montréal. With the starting capital, they paid an outside Montreal development shop $40,000 to build the first version of the product.

Outsourcing the technology is the decision Andrew now points to as the most expensive learning of his early years. The platform shipped and worked, but when they wanted to add features the next year, the same shop quoted them $120,000. By the third year, the architecture they had paid an outside vendor to build had reached the point where it could no longer be extended. Whatever ambitions Andrew and his co-founders had for the company were constrained by a technology stack they had bought but did not own. StudentSphere continued for ten years as Andrew and his co-founders eventually moved themselves off the payroll, hired a General Manager, and reduced their own involvement to occasional board calls. The company was sold in 2022 to a UK firm that wanted the technology for a North American expansion, for an amount that came out to less than $100,000 for all the founders, on roughly a decade of work.

Stay22

In the summer of 2014, while continuing to work on StudentSphere, Andrew attended Startupfest, the annual conference held in the Old Port of Montreal where the Canadian early-stage technology ecosystem assembles for three days every July. Andrew was sitting in the audience watching a young engineer named Hamed pitch a B2C travel company. Hamed had been kicked out of Dawson College a few years earlier for hacking the school’s system, and he was building a product designed to take on Expedia, Booking, and Kayak directly. Andrew was impressed by Hamed, but he was unimpressed by the strategy. He introduced himself after the pitch and told him, to his face, that he was wrong about the whole premise of the company. Going B2C against the incumbents in travel, who spent more than $10 billion a year on marketing budgets between them, was not a winnable fight no matter how good the product was. The right way to compete in travel was to embed inside the distribution channels where people were already making travel-adjacent decisions, the platforms where they were already buying tickets to events.

They reconnected a few years later. They tested working together for a month, selling a few event integrations, and then applied to Travelport Labs, the corporate accelerator run by the global distribution system Travelport. Travelport accepts only five companies per year. They got in and moved to Denver for four months during the winter of 2016 into 2017. Andrew, who was so broke that he had convinced himself he hated traveling, got a crash course in an industry he had previously known nothing about. He learned the suppliers, the global distribution systems, the commission structures, and the way affiliate revenue flowed from a booking back through three or four layers of intermediaries. Travelport invested US$35,000 for 8% of the company. While that may seem expensive, the founders did not negotiate, as the education was worth more than the check.

The next accelerator they entered was FounderFuel, the Montreal-based program Andrew had previously applied to with StudentSphere and been rejected from. With Stay22, he and Hamed made it in. The terms were $200,000 for 5% of the company, paid in two tranches across a 12-week program. The team grew from two to six during the cohort, with two new hires from Hamed’s network and two of Andrew’s former UQAM classmates. Andrew paid everyone, including himself, $1,000 a month. He was 29 at the time. He owed his parents $10,000 from previous loans he had not been able to repay, and he was living on ramen and the half of the rent his girlfriend (now fiancée) was paying for him. Somewhere in the middle of that year, on the theory that if Stay22 failed he was going to need a stable career, he applied to become an air traffic controller, and washed out of the training program.

FounderFuel ended in the autumn of 2017 with a demo day pitched in front of an audience of 2,000 people. Andrew and Hamed had been told by a FounderFuel mentor named Isaac that a seed-stage startup raises money on one of three things. The first was a powerful vision the founder could articulate well enough that an investor would buy the story before the numbers existed, and Andrew was not, by his own admission, a strong vision storyteller. The second was pedigree, the kind of resume that read “Stanford” or “former Google engineer” across the top of the deck. Hamed had been kicked out of Dawson College before he finished his degree, and Andrew had only barely finished his own at UQAM, which meant the second door was closed to them as well. The third was traction, and that was the only path left. They were the first team in the building every morning and the last team to leave every night, every working day for the full duration of the program.

They closed a seed round on the strength of the demo day numbers: $750,000 at a valuation of $3.75 million. The lead investor was Seven Gates Ventures, a fund out of Vancouver that Andrew chose partly because the firm had the kind of West Coast network he and Hamed lacked. Real Ventures, the Montreal-based seed fund, also came in. So did several angel investors who had found their way to Stay22 through Anges Québec, including one who had moved to Montreal from Italy and had no obvious reason to be writing checks to a Canadian travel startup, but wrote one anyway.

Ides of March

By February of 2020, Stay22 was doing $110,000 USD in monthly recurring revenue and the team had grown to 24 people. A new financing round had been negotiated, term sheets were signed, and several investors had already wired their commitments. Andrew was 33 years old. He had spent more than a decade getting to the point where he was about to fundraise his way into the version of his career that other founders in his cohort had been living for some years.

The pandemic arrived in the second week of March. Stay22 sat at the intersection of travel and events, the two industries the global economy was about to close completely, and revenue fell 90% in a matter of weeks. The cash that was supposed to fund the next 18 months of operations had only partly landed in the company’s bank account. The investors who had committed but had not yet wired their tranches now made the calculation that the company was about to go bankrupt, deciding they would prefer to keep the money rather than send it.

Andrew called them. The first calls were polite, and the investors told him the money was coming next week. The next week came, but the money did not. His follow-up emails went unanswered, his calls began going to voicemail, and by April, he could no longer reach them at all. One of them, who was already on the cap table as an angel investor, told Andrew, when he finally got the man on the line, to sue him if he wanted to but that he was not sending the money. Another sent a paper check with written instructions not to deposit it on the grounds that there were no funds in the account it was drawn against. Andrew kept the check on his desk. He still has it, sitting next to his monitor as a daily reminder of never celebrating until the money hits the bank.

He had to take legal action against the investors who had signed and refused to wire. The lawsuit was not, in any meaningful sense, a recovery exercise. As a director of the company, he had a fiduciary obligation to the investors who had wired, the ones who had stood by him, to demonstrate that he had pursued every available legal remedy against the ones who had not. If he failed to do so, those supporting investors would have had grounds to sue him personally for the duty he had not discharged. After filing and opening up a case, he moved on to the question of whether the company would continue to exist.

He cut the team from 24 people to 8. The conversation he comes back to when he tells the story of that period was not with any of the laid-off employees, but with his accountant, a man named David at a Montreal firm called Finalytics. David had been billing the company close to five figures a month for the work he did on the books, tax filings, and regulatory paperwork. In the spring of 2020, Andrew and his COO, Simon, sat across from David and delivered the news that the company could no longer pay. Andrew had no idea when, if ever, he would be able to clear the debt, but the work still had to be done because the company had no operations team left to do it. David could have stood up, walked out of the meeting, and quit on the spot, and Andrew would have had no leverage to keep him. Instead, David agreed to keep working without compensation for an undefined period, on the strength of a relationship he and Andrew had built over several years. Six months later, when revenue had begun to return, Andrew started paying David again. Andrew believes that if David had walked out of that meeting and quit, Stay22 may not have survived. Without accounting and daily cash flow projections, Simon wouldn’t have a single hair left.

The remaining investors told him to keep going. He sat down with what was left of the team in the spring of 2020 and ran a two-week brainstorming sprint. They built three minimum viable products. The first one failed within days, and the team shut it down before they had spent any meaningful time on it. It was a map-based product for nurses and doctors who needed accommodation near hospitals they had been temporarily assigned to during the early months of the pandemic. The Quebec government, which they would have needed as a partner to make the product function at scale, did not move at the speed a startup needs from its partners, and the idea died.

The second was a cross-sell product for e-commerce stores on Shopify, which offered travel-adjacent services to customers who had just purchased something from a Quebec apparel brand or wellness company, like Prana, Ciele, Poches & Fils, or Café Liégeois. The product worked in the sense that it generated revenue, but the unit economics did not scale, and the team eventually let it go.

The pivot that worked emerged from a parallel set of conversations Andrew had been having with Quebec content creators who had stopped traveling internationally and had begun rediscovering their own province. The travel bloggers wrote about the rediscovery first, the Instagram accounts came after them, and the YouTube channels arrived last. Stay22 had a map-based product designed for events, but the bloggers did not want a map. Andrew sat down with them in workshops he ran personally over the course of two weeks, while Hamed coded in the evening what they had discussed in the afternoon. Every morning, Andrew presented the wireframes to the creators and noted their reactions, and they iterated again. By the end of the two weeks, the team had their third minimum viable product. By the end of the second month, they had product-market fit. The creators wanted a way to monetize the content they were already writing about travel through affiliate links to hotels, restaurants, and activities that appeared in the posts they were already publishing, and they were happy to give a software company access to their websites in exchange for a share of the revenue. This is the version of Stay22 that exists today.

Almost exactly one year later, in March 2021, Andrew learned that Airbnb was shutting down its affiliate program. He saw the news through industry channels before Airbnb officially called him, and for a few weeks, he allowed himself to believe that Stay22, given the depth of its integration with the platform, would be exempt. The phone call came in late March. The Airbnb relationship manager told him that Stay22 had been a great partner and that the team appreciated the work Andrew had done on the API, but that Airbnb’s strategic direction no longer accommodated affiliate partnerships. The company would have 60 days to wind down the integration. Airbnb represented 80% of Stay22’s bookings.

He called his mother, who was in Florida with his father at the time. He told her what had happened, that this was the third near-death event the company had faced in 18 months, and that perhaps the universe was trying to tell him something he had so far refused to hear. His mother told him that nothing happens for nothing in this life, that this was a sign he was supposed to keep going, and that there was a reason for it that he could not yet see.

He pivoted Stay22’s supply layer onto Trivago, the German meta-search engine, and the first month under the new arrangement was extraordinary. The company touched almost $500,000 in revenue in a single month, more than any month it had ever recorded. Andrew began to allow himself to believe that the Airbnb cut had been the best thing that had ever happened to the company. Then Trivago called with a correction to the numbers from that first month. The relationship manager explained that Trivago’s accounting had been overpaying Stay22 for clicks at an unsustainable rate, and that the rate would need to come down significantly.

Andrew was burning $200,000 a month against a runway of approximately three months, and the data did not support keeping the company open. The rational decision, by every framework he had taught himself to apply, was to wind it down and start something else. Andrew did not see the situation in those frameworks anymore. Raising more cash wasn’t on the table, not with a 90-day runway, and certainly not after getting burned by their last investor. He was done looking for a rescue party. Time was the only resource he could not replenish, and starting another company would burn years he could not recover. He was 34 years old, so starting over was no longer something he could treat as a free option. The creator base he and Hamed had spent the previous year building had 90 days to generate enough revenue to save the company. If it did not, he would close Stay22 at the end of the runway and move on.

It delivered. By the middle of 2022, the company was running at roughly $1.5 million in monthly revenue. By 2023, it was profitable, and it has been profitable every month since, doubling in revenue every year for the past five years. The team grew from the post-pandemic skeleton of eight to roughly 125 employees, tripling the team size within two years. Andrew personally conducted the final interview for every hire. He had learned, from an earlier batch-hiring spree that had broken the company’s culture in ways he had spent two years repairing, that hiring more than 15% of a team per quarter was the most reliable way to destroy a small company’s culture. The one-employee-a-week cadence was his answer to that mistake.

Every March since the pandemic, the company has faced some kind of existential threat. March 2020 was COVID. March 2021 was Airbnb. March 2024 was a brutal Google algorithm update that stripped Stay22’s independent content-creator partners of 40% of their search traffic, forcing the company to pivot hard toward major digital publishers who still held sway on the open web. By 2025, a second paradigm shift arrived: the rise of LLMs and AI search began draining traffic away from text-based Google results entirely, sparking a massive exodus toward YouTube, Instagram, and social platforms where creators could build un-scrapable, direct relationships with their audiences. Each March, the question has been the same, and the answer has been to keep going. There’s an opportunity in every crisis that is faced, and at all times, a deep dive should be done to find that opportunity.

Today

In February 2026, Stay22 announced a US$122M minority growth investment from Summit Partners, the Boston-based growth equity firm. The deal was the company’s first institutional capital event since the seed round Andrew and Hamed had closed in 2020. By the time it priced, Stay22 was processing more than US$1 billion in annual transactions and working with more than 5,500 creators. On the morning of March 11, 2021, Andrew had been sitting in his office reading an email from Airbnb and asking himself whether the universe was trying to tell him to fold.

He runs the company today on a set of operating principles that have hardened over time. He implemented the Entrepreneurial Operating System in 2019. He runs the executive team on the framework Patrick Lencioni laid out in Five Dysfunctions of a Team. He recommends Annie Duke’s Quit: The Power of Knowing When to Walk Away to other founders because he believes the harder problem in entrepreneurship is not perseverance but the discipline of knowing when to stop.

The conversation that reset his understanding of his own role as chief executive happened within the past year. He had been trying for two years to be the kind of CEO he believed the company needed at its new scale, a more delegating, bottom-up version of himself, a man who built management systems and trusted his executives to run them. Then, his COO, Simon, asked for a meeting. He told Andrew plainly that the experiment was not working. He explained that Andrew was a wartime founder who naturally belonged inside the details of the business, and that he had been operating against his own nature for two years. He was miserable in the process, and Simon told him to stop fooling himself. Andrew took the feedback, leaned back into the active work, and the company immediately started moving faster.

He lives now in Laval, the town next to the one he grew up in. His daughter will turn 3 and his son 6 this summer. He is home only one evening of the work week, and sometimes none at all. But he makes sure he is home every weekend without exception, and on those days, he does not look at his phone while the children are awake. His brother remains a firefighter in Montreal. His father retired at 53, after selling his chain of window repair shops and reaching financial independence. Today, his parents spend six months of every year in Florida among the other Quebec snowbirds.

Andrew turns 39 this summer. He previously said that he hoped to surpass his father’s success by the age his father retired. With the Summit Partners deal, he has already surpassed his father in raw dollar terms.

But the true difference between the two men is no longer the money. It is that his father retired the moment he had enough, and Andrew has not yet figured out what enough looks like. Maybe in the next few years he will reach the point his father reached. Maybe not. Who knows?

Welcome to the first edition of the Amiral newsletter.

We started Amiral to back founders who see what others miss and build where others won’t.

For our first issue, we’re starting with Patrick Murphy, founder of Maket. He’s making residential architecture accessible to anyone, no CAD, no $10K design retainer, just describe what you want. It’s a massive opportunity hiding inside one of the largest, most fragmented, and least digitized industries in the world.

Patrick is exactly the kind of founder we built Amiral for.

You’re receiving this because you’re part of the Amiral network. Not relevant? Unsubscribe here.

A warehouse on the outskirts of Montreal was the not the kind of place a father takes his 14-year old son.

Patrick Murphy sat in the passenger seat, watching the city’s polished neighbourhood dissolve into industrial grey, trying to keep his nerve. He asked for this trip himself, explained his idea with enough conviction that his father had listened, driven across town, and walked through a an industrial factory that looked like it was a hideout for criminal activity. Inside, among bolts of fabric and racks of blank shirts, Patrick picked out his production run while his father paid for it. The logo was already finished, as Patrick had built it himself, on Illustrator.

He called the brand Ambassador Apparel, because they would be ambassadors for Christ. Even at 14 he understood that a name should carry meaning and weight. He took the shirts to school and sold them in limited drops, manufacturing scarcity before he had a word for the strategy. He never lost money, but never really made any either. Each run broke more or less even.

This was Patrick’s first entrepreneurial experience, and although it was not a success story by any conventional measure, it proved something else. That he could originate an idea, build it into something physical, find the people who wanted it, and moved it from his hand to theirs.

Childhood

Otterburn Park sits on the South Shore of Montreal, a quiet city beside the hiking trails and rocky face of Mont-Saint-Hilaire, close enough to feel the mountains and far enough from downtown to breathe. Patrick was born there in 1994, the youngest of five children. In a large family, birth order shapes personality as surely as anything else does, and the youngest child often arrives already partially formed by the weight of the personalities stacked above them. In Patrick’s case, the defining characteristic of being last was that everyone left him alone.

“They always allowed me space to just be Patrick,” he said. “I was doing entrepreneurial stuff, I had a ton of ideas, and they were always really supportive.” He was not pushed toward medicine, law or any of the respectable professional tracks that families sometimes mistake for ambition. Whatever path opened in front of him, he would have to find it himself.

His father had grown up in California, studied theology in the United States, and then completed his PhD in Quebec, arriving in Francophone Canada in the 1980s to run a master’s-level training program for pastoral students. His father spoke no French. He was, Patrick would later say, about as locally intelligible as someone who had just landed in rural China. And yet he stayed, built a ministry, raised a family, and ran his life with the independence of a man who reports to no one. Patrick did not see the word “entrepreneur” written anywhere in his house growing up, but he was watching one in real time. His mother was an artist, moved by the Group of Seven deeply and permanently. She painted and created throughout Patrick’s childhood, and her aesthetic sensibility became something she passed on without trying.

Growing up in a house with five children on one salary and a mother working part-time as a teacher and artist, comfort was not the operative word. They never felt poor, however. The Lord always provided, as his father would say, and Patrick tends to agree. But there was not a lot of extra. There were five kids, one income, and a life in ministry that demands the soul in ways it does not always reward financially.

Patrick watched his father navigate this with the specific equanimity of someone who has made peace with uncertainty, and something about that lesson settled into him deeply. “The shared experience of an entrepreneur and a missionary is actually really close,” Patrick said. Both are trying to make something work with insufficient resources and an audience that isn’t always there. Both go through long stretches where nothing seems to be growing and where the natural response is to wonder whether they should have done something else entirely.

What Patrick discovered at 14, running Ambassador Apparel out of his school locker, was that he was a communicator and a salesman in the sense that he liked the work of persuading people, the social texture of it, the reading of what someone wanted and then offering it to them. He was not a scientist or a mathematician, and rather than spending years fighting against his nature, he leaned into it. He built the brand because he could build it. He sold the shirts because he was good at selling. He understood the mechanics of scarcity before he understood the term. And when each run broke even, he didn’t view this as failure. He viewed it as confirmation that the machinery worked, and that the next iteration would improve.

What also became clear, in those same years, was that his sense of design was not casual. He had built the Ambassador Apparel logo himself because it had not occurred to him to outsource it, and because he had opinions about fonts, spacing, and a hunch on what a good logo communicated versus what a sloppy one did. He was the kind of kid who cared about what things looked like, genuinely cared, the way his mother cared about her paintings.

University

After high school, rather than enrolling in a traditional university program, Patrick went to CEGEP for graphic design. He wanted the technical vocabulary of design so that he could do contracts, generate income, and develop skills that would make him useful rather than dependent. He was not interested in a degree for its own sake. He wanted tools.

The three-year program gave him those tools, and after CEGEP, he went to Concordia University for communications, specializing in sound production, rounding out a creative education that was broader than most people would have chosen.

During those years, while completing coursework, he was also working full-time at a performance marketing agency. He had come through an unexpected door, where Patrick had started a hockey blog called Hockey Busts, covering draft prospects with earnest obsessiveness. The agency needed someone to run a hockey blog for their clients. As matches go, it was almost embarrassingly convenient.

He joined as the one of the first employees. He was in his early twenties, recently out of design school, and knew very little about digital marketing. His boss, James, knew this and hired him anyway. Patrick would later describe this as the defining professional gift of his early career, a boss who extended responsibility before it had been earned, who let mistakes happen, who trusted Patrick with increasingly important pieces of the business and then stepped back to watch what happened.

“James just gave me a shot,” Patrick said. “I was just coming out of university. I did not know anything about anything when it came to digital marketing. And he allowed me to run a very important part of his business.” The lesson Patrick absorbed was less about marketing specifically and more about what good leadership looks like from the receiving end. A mentor who extends trust, even when the trust is not yet fully warranted, creates a different kind of professional than one who makes people earn every inch of responsibility.

At the agency, Patrick learned the mechanics of performance marketing in ways that would serve him a decade later, on how to drive inexpensive traffic, how to measure conversion, and how to think about customer acquisition costs in relation to customer value. He worked across clients in different industries, including a shoe company obsessing over return on ad spend, a solar company needing high-quality B2B leads, a fintech application fixated on cost per install. Each client was a case study in what a different kind of business needed to grow, and Patrick was taking notes on all of it. He also became certain that he did not want to be in the services business forever, and that he wanted to build something of his own.

COVID

The transition came through ThirdBridge, a software development shop with ambitions to build an office management platform. Patrick joined as head of commercialization, a role that suited his skills and gave him real exposure to the work of building software. He had ideas about products, always had, but he did not know what it cost to build them, how long it took, what testing looked like, what deployment meant, and how things broke when real customers got their hands on them. ThirdBridge gave him that education.

He worked closely with the company’s CEO, Pierre-Étienne Bousquet, who trusted Patrick with access to leadership conversations that a typical employee at his level would not have seen. Patrick was thinking alongside the founder, not just executing for him. He learned what it meant to make a product decision, commit to a technical direction, and discover mid-build that the thing you were building wasn’t quite right.

ThirdBridge’s platform was aimed at a problem that COVID rendered immediately irrelevant, the friction of office check-in solutions, conference room booking, and shared physical space. When the pandemic hit, the company cut the initiative. Patrick found himself, for the first time, genuinely unemployed and free.

There was someone he had been thinking about for a while. Years earlier, back when he was still at the performance marketing agency, a man named Stéphane had reached out to him. Stéphane had grown up in Montreal, moved in overlapping circles with Patrick without the two of them ever becoming close, and been running his own architectural design agency.

Stéphane had an idea for a SaaS platform and was looking for a co-founder. Patrick told him no, or something close to no. The timing was wrong, and Patrick needed more experience, learn more about software, and become more useful before he could be useful to someone else. They stayed loosely in touch. After ThirdBridge went quiet, Patrick called Stéphane.

A month after he had stopped going into an office, ThirdBridge called Patrick back. They wanted him to return. He sat down with his wife, who had been with him since university and who understood, what kind of person she had married, and told her what he was thinking. He wanted to build a company, but he wasn’t sure it would work and if he was ready. She listened and then asked, “What’s the worst that happens? You try this and it doesn’t work, you can go do something else. And the best that happens is that you try this and it works and you’re really happy.”

He describes her as having kicked him off the ledge. He was standing at the edge of something, hesitating, and she pushed. He turned ThirdBridge down and called Stéphane back.

Maket.ai

They started the company during COVID, working remotely from the beginning. Neither of them was an engineer. They were two business-oriented founders with ideas, relationships and the ability to sell, but without someone on the team who could build the underlying technology. They were, in fact, constructing a pitch without the product to back it up. They got into NEXT AI, one of Quebec’s most prestigious startup accelerators, on the strength of a personal relationship Patrick had with the program director. By their own admission, they did not belong. “We had no idea what we were doing,” Patrick said. “We’re two founders. We’re not technical. You had to have a technical founder and a business founder to get in. We’re both business guys.” They got in anyway. The program introduced them to someone at Mattamy Homes, Canada’s largest home builder.

Mattamy had been thinking internally on whether AI could generate floor plans.

The question landed at a moment when Patrick and Stéphane were open to a new direction. Patrick looked around at the housing stock in Otterburn and told Stéphane, “Dude, everything is ugly. I hate these houses, they look terrible. Everybody’s living in terrible garbage boxes that all look the same. Why does this space around us not look nice?”

Mattamy’s suggestion aligned almost perfectly with that irritation. And yet the pivot was not easy. The technical challenge of using AI to generate floor plans was, as Patrick and Stéphane would quickly discover, much harder than it appeared. “Nobody’s doing this,” they had thought when Mattamy posed the question. “It must not be that hard.” It was, in fact, incredibly hard.

The argument over whether to make the pivot happened on a phone call while Stéphane was hiking up a mountain, the signal cutting in and out, both founders raising their voices across a dropping connection. Stéphane wanted to stay the course on their original thesis of an online home sales platform. Patrick wanted to go all in on generative architectural design, on the harder, stranger, more exciting path. You do not know who your business partner really is until you have disagreed with them about something that actually matters. They resolved it by following the money, or the prospect of it. Mattamy was willing to be their first paid pilot. A real first customer changes the economics of almost any argument. They took the generative design path, secured the contract, and used that traction to get into Techstars.

Distribution

What Patrick understood before Maket had a good product was that good products need customers to become good, and customers do not appear on their own. He had been watching this mechanic for years, at the agency, at ThirdBridge, in his own early ventures, and he had come to believe that distribution was not a problem you solved after the product was right. Distribution was something you built alongside the product, sometimes ahead of it, because without the signal that real users generate, you are building in the dark.

Rather than following the conventional early-stage advice of cold calls, warm introductions, and careful qualification of prospects, Patrick and Stéphane spent money on Facebook ads. They set up landing pages, tested messaging, drove traffic to a waitlist, and watched what happened. What happened was that people signed up. A lot of people. By the time the V1 of the product was mature enough to support real users, Maket was seeing roughly 1,000 sign-ups per day.

The aggregate spend over the course of a year came in part by a commercialization subsidy from the Quebec government that Patrick deployed. “The government is giving us free money,” he reasoned, “we’ll spend it on ads.” The marketing drove organic search, which drove more sign-ups, which made attribution complex, but it also generated data that would be more valuable than the numbers. Feedback forms, customer support logs, live chat transcripts, and churn exit surveys were the holy grail of the government money spent.

Olivia, who joined Maket before she had finished her university degree and would still be with the company three years later as she completed her final semester, managed the customer-facing edge of this feedback loop with the specific thick-skinned patience of someone who has absorbed a great deal of complaint on behalf of a product that was not yet what it needed to be. She knew the customer the way someone knows a difficult family member, deeply and sometimes painfully. What came out of all those complaints, feedback forms and support emails was a portrait of what the platform needed to become, a portrait that would eventually shape the architecture of V2 in ways that a hundred curated customer interviews could not have produced.

One of the key lessons Patrick absorbed at the performance marketing agency was less about marketing specifically and more about what good leadership looks like from the receiving end. A mentor like James who extends trust, even when the trust is not yet fully warranted, creates a different kind of professional than one who makes people earn every inch of responsibility. Patrick, now in the mentor seat, would extend that same trust to Olivia, building a knowledge base of the customer that made her indispensable.

Fundraising

The fundraising process lasted 14 months, produced 100+ rejections, and came within weeks of ending the company.

Patrick began preparing for the seed round in Q3 of 2024, at a point when Maket was on an upward trajectory but carrying a structural vulnerability that any experienced investor would identify immediately, that the product was not good. The V1 needed a lot of work, but the initial concept was presentable and functional. The team was two business-oriented co-founders without a strong technical leader, which meant that Maket had distribution and market validation but could not fully capitalize on either. Patrick understood this, but decided to run a process anyway for survival.

He compressed the meetings into the shortest window he could manage, stacking them back to back in August and stretching through November, creating the artificial urgency that a tight timeline produces in any serious negotiation. Inbound came from tier-1 investors. Conversations went deep, some progressing all the way to investment committee presentations. And then came the rejections, one after another, patient and varied in their specific wording but consistent in their underlying message: a product that wasn’t good enough and a founding team without a technical founder.

In July of 2024, a message arrived from someone Patrick had not been expecting to hear from. The man was a successful entrepreneur who had sold his company and was now looking to deploy capital into things he understood. He was interested in Maket, and they talked several times over the following weeks. The conversations went well, which is to say they went slowly, because the man seemed to move at his own pace and respond on his own schedule.

In August, Patrick was on a flight to Japan. He was taking a real break, the kind that founders rarely allow themselves and that Patrick had learned, partly through experience and watching his father manage exhaustion through decades of ministry, to actually take. The message came through during the flight and the investor was in. He would be the lead, the round would be anchored, and the long process would be over.

Patrick landed in Japan, spent the rest of the trip doing data room and term sheet work between stretches of rest. When he flew back to Montreal, he told his team they were good to go.

And then the man stopped responding.

Patrick followed up. He reached out to mutual contacts, people who knew the investor and had vouched for him. They described him as a great investor, someone who would be terrific on a board. He just wasn’t responding. A few weeks passed, then a month. It became clear, slowly and then all at once, in the way that a funding round falls apart, that the yes had been a no that hadn’t yet been delivered. Maket had been operating on the assumption that the round was closing while the round was, in fact, dissolving.

“We were about to shut down the company,” Patrick said, “because we almost ran up our runway.”

He met with Amiral in January of 2025. Patrick had first encountered Nectar about 2.5 years earlier at a mixer in Montreal’s startup ecosystem, when the fund was still in the process of being raised. He had stayed loosely in touch. Later, Fred had become a kind of informal mentor through a Quebec Tech program. Patrick met Fred for coffee and told him the truth, all of it, including the ghost investor, the near-shutdown, and what had gone wrong. At one point, Patrick told Fred directly not to invest. “I’m talking to you as someone I consider a close friend. I don’t think you guys should invest.”

Fred never forgot that. The honesty of it, the willingness to prioritize a relationship over an opportunity that might have closed a desperate gap, was the kind of signal that stood out as something durable. When Amiral was capitalized and the timing was right, that meeting was still sitting in the ledger of things Fred knew about Patrick.

The round eventually came together. Blitzscaling Ventures closed on their commitment in January of 2025, while Patrick was back in Japan, but this time closing their now largest customer. Their partners applied what Patrick described as a formula rather than a gut feeling, that the company had distribution, the ability to blitz a market, and disrupt technology within the space. Jeff, the partner who championed the deal from Blitzscaling’s side, had a single quality that Patrick would describe as the thing that mattered most after hundreds of rejections. He asked thoughtful questions and understood what he was hearing. The conversation that closed the round was, Patrick said, “very, very easy.” Amiral Ventures ultimately led the $3.7 million seed round alongside Blitzscaling, Hidden Layers, BYVP, StartUp in Residence, Spatial Capital, and others.

Bruno Morency, an advisor and investor through Techstars, had been with Patrick through much of the navigation, helping him think through the negotiations and the moments of uncertainty. “Bruno really, really helped me a lot during fundraising,” Patrick said. The visible part of fundraising is the pitch; the less visible part is the person in the corner helping you figure out what to do next, and Patrick is someone who is honest enough about what he doesn’t know to go find those people.

“It’s like a long sales cycle,” he said, “and you’re knocking on hundreds of doors and you just have to knock on one and find somebody who has conviction. It’s all like dating, right? You meet somebody for 15-30 minutes, and you know if they’re leaning in.”

Ski Crash

Three years before the seed round closed, in 2022, Patrick crashed on a ski slope and fractured his femur badly enough that paralysis seemed possible. He recovered. The bone healed, and continues to ski on the weekends.

But something recalibrated in the accident’s aftermath, in the weeks of recovery and the months that followed. Patrick had started Maket in 2020 and had been building it for two years when it happened. He was the same person after the crash that he had been before it, curious, optimistic and energized by design and by the problem he was trying to solve. But the crash gave him a counterweight to the ambition, a second truth to hold alongside the first. “Every day is like a plus-one bonus for me,” he said.

What he means by this, in the context of building a company, is nuanced enough to be worth unpacking. He is not saying that the accident made him less ambitious, or that the brush with paralysis made him indifferent to outcomes. He is saying that it forced him to hold two truths simultaneously, the truth that what he is building matters and demands everything he has, and the truth that no amount of what he has can guarantee the outcome, because the fragility of life does not negotiate with ambition. “No matter how hard you build,” he said, “there’s a certain element of just luck and right place, right time and blessing, whatever you want to call it, that determines some of the paths.”

His father’s advice during the dark periods of building Maket would draw directly from decades of ministry experience, to give yourself three-month marks. Set a start time, check in at three months, see where you are. If you still feel like quitting, allow the feeling but don’t act on it. Then do it again. “It would be the same thing of when he was in ministry,” Patrick said. “He would just always take a reassessment.” The advice sounds simple but it is structurally very good, because it takes the chaos of a difficult stretch and turns it into a data collection exercise. You are not deciding whether to quit; you are deciding whether the evidence at a specific checkpoint supports continuing. That reframe saved Patrick more than once.

Fun as a Moat

Patrick has been building Maket since 2020, which is a long time to be doing something that started, by his own admission, as a guess. The guess was that AI could do something for architecture, interior design and floor plan generation that had never been done before, that there was a market of homeowners, builders, real estate developers and agents who were underserved by existing tools, and that the combination of distribution and technology could unlock something large. Five years in, with a V2 about to launch, a seed round closed, 30,000 sign-ups per month, and 50,000+ users waiting for the next version of a product they were already using, the guess looks increasingly like a thesis.

His competitive advantage, as he sees it, is that he is having fun. He quoted a tweet to that effect, couldn’t remember exactly who wrote it, but felt it described him accurately enough to repeat. As competitors have multiplied in the generative design space, the fun has acquired a sharper edge. He is nice, he said, but also very competitive, and when he sees a competitor doing something, his instinct is to figure out how to counter it. The fun and the competitiveness are not in tension; they are the same thing, because he is playing a game he has chosen and cares about, rather than one he has been assigned.

He has resisted the pull of San Francisco, not without understanding what it offers, but with a specific argument against it that a mentor once made to him, that building in Montreal, with less access to capital and therefore a slower ramp, meant that when the technology matured enough to match the ambition, the company had not yet spent all its money chasing a vision the market wasn’t ready for. The slower ramp had been, in retrospect, a form of protection.

He believes Montreal is due for a rise on the global stage, that the concentration of AI talent and the quality of the institutions feeding it create the conditions for something significant.

His father lives nearby, and discovered recently, that AI can do extraordinary things. He uses Claude to write theology books, gets them approved through an e-publisher, creates songs with Suno, generates images. Patrick watches this with the specific delight of someone who has spent 6 years trying to build something what his father is now using, and who sees, in his father’s creativity finally flowing freely through the right tools, a version of what he is trying to give to everyone. “People who thought that they weren’t creative, now they can be creative.”

Maket is building the platform for generative architectural design. If you’re a homeowner, home builder, real estate developer, or agent who needs to create and modify floor plans, check out Maket.ai.

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