What do you think?
Rate this book
How We Can Win: And What Happens to Us and Our Country If We Don't
Our kids are smart, our banks are sound, our health care system is humane, our democracy is stable—but technological change is about to disrupt our economy and threaten our way of life. Canadians aren’t ready for the race to the future. Can we still catch up—or even win?Yes, says Anthony Lacavera, one of Canada’s most successful entrepreneurs and venture capitalists. But we need to change the way we think and talk about our own abilities—dream bigger, aim higher and go for gold, not bronze. We also need to change the way we do business. Our dominant business culture, Lacavera believes, is fundamentally traditional, backward-looking, insular, timid, greedy, unoriginal—everything that Canadians themselves are not. And that unCanadian business culture, protected by outmoded regulations and government policies, is stifling our economic growth. It dumps roadblocks in the path of entrepreneurs who want to build the kind of powerhouse businesses that will create jobs and fuel our economy. Anthony Lacavera faced those roadblocks himself, when he was building WIND—an epic battle against the big three telecommunications giants in Canada. But he’s certain we have the talent and the brains to tear those roadblocks down. He gives us vivid portraits of some of Canada’s most important natural our talented, innovative entrepreneurs, who want to change the world for the better (and, yes, make money while they’re at it). But we are shipping far too many of them to the United States, gift-wrapped in our tax dollars. They don’t want to leave—they’re forced out because it’s just too difficult to build big, bold businesses in Canada. How We Can Win explains what we need to do to keep them here, and what all Canadians must do to ensure our future prosperity. Our biggest problem is not that we are a small country, but that we think too small. We can be a nation of big dreamers and bigger doers. Not by aping Silicon Valley, but by focusing on uniquely Canadian strengths and then doubling down on them. If we bet aggressively on ourselves, and our future, rather than clinging to the status quo, we will create a new, more solid economic foundation—one that allows us to win the race to the future without leaving home.
- GenresBusiness
274 pages, Kindle Edition
Published October 3, 2017
8 people are currently reading
79 people want to read
Ratings & Reviews
Friends & Following
Create a free account to discover what your friends think of this book!
Community Reviews
Displaying 1 - 7 of 7 reviews
December 28, 2025
Great book to be read by every Canadian entrepreneur and policy maker, even going on 9 years after publishing. IMO the cultural arguments are what are most important here, and they're timeless. It's also a powerful "you can do it" and "we have to do it" book which is motivating.
It was also interesting to note some of the dated arguments in this book which AL is undoubtedly completely aware of. Quick (imperfect) Gemini summary of some of these points:
***
Anthony Lacavera’s How We Can Win (2017) argues that Canada struggles to commercialize its innovations, often selling startups to foreign buyers too early ("branch plant" mentality) and failing to protect intellectual property (IP).
While his central thesis remains relevant, the explosion of Large Language Models (LLMs) and Generative AI (2022–2025) has "dated" specific pillars of his argument in three critical ways:
1. The Shift from "Venture Capital" to "Sovereign Capital"
Lacavera’s 2017 argument focused on the "scale-up gap"—the lack of Series B/C venture capital in Canada to turn $10 million companies into $1 billion companies.
How it is dated: The economics of LLMs have made this gap irrelevant by making it insurmountable for any traditional VC ecosystem. Building a frontier model (like GPT-5 or Claude) now requires tens of billions of dollars in compute infrastructure (GPUs/Data Centers).
The Reality: The game is no longer about "growing a startup"; it is about nation-state level industrial policy. The "winning" strategy Lacavera proposed (better VC incentives) is mathematically insufficient for the AI era, where only hyperscalers (Microsoft, Google) or sovereign funds can afford the entry ticket.
2. The "Data Colony" Problem replaced the "Brain Drain"
Lacavera worried about Canada exporting talent (engineers moving to Silicon Valley) and IP (patents sold to US firms).
How it is dated: LLMs have automated the extraction of value. Canada no longer just loses people; it loses its digital history. US-owned models (OpenAI, Anthropic) have scraped Canadian media, literature, and government data to train their models, effectively colonizing the country's informational heritage without hiring a single Canadian.
The Reality: We are no longer just a "branch plant" where Canadians work for US subsidiaries; we are a "data farm" where Canadian cultural output is harvested for free to improve American products.
3. Obsolescence of Specific Verticals
In How We Can Win, Lacavera placed heavy emphasis on telecommunications (5G) and blockchain as key battlegrounds for Canadian innovation, reflecting his background with Wind Mobile.
How it is dated: While connectivity is important, Generative AI has displaced 5G as the primary driver of economic productivity. The "pipes" (telecom) became commodities, while the "intelligence" (AI) became the value capturer. A strategy focused on "winning" in telecom infrastructure (his 2017 focus) misses the fact that the value has moved up the stack to the application and reasoning layer.
***
Commentary on AI and Sovereignty:
While he hasn't written a dedicated book on AI, his recent speaking engagements and short-form writing have touched on the "Data Colony" concept. He has argued that Canada is repeating its mistakes from the oil and telecom eras by failing to build sovereign AI infrastructure, allowing US giants to once again extract the value.
***
I was curious to see what an LLM would say about what AL's updated pitch would be in late 2025. Would be interesting to know if Anthony agrees:
***
Based on Anthony Lacavera’s recent activities—specifically his July 2025 acquisition of Wealth One Bank—and his established philosophy, his updated pitch to Canadians would shift from "How We Can Win" to "How We Can Survive."
The central argument would evolve from preventing a "Brain Drain" (losing people) to preventing a "Mind Drain" (losing the ability to think independently as a nation).
Here is the updated pitch, merging his 2017 concepts with the reality of the AI era.
The Core Thesis: "Stop Being a Landlord for American IP"
Lacavera would argue that Canada has misunderstood the AI revolution. We are currently positioning ourselves as a "server farm" for the US—using our clean energy and land to power American models (like OpenAI or Anthropic) that we then rent back at a premium. This creates a "Data Colony" where Canada provides the raw resources (energy, data, talent) while the US captures all the value.
Pillar 1: Competition (The "Oligopoly" is Now a Security Risk)
In 2017, he argued that the telecom oligopoly (Bell, Rogers, Telus) hurt consumers.
The 2025 Update: The oligopoly is now a national security threat.
* The Argument: A lack of competition in banking and telecom means Canada lacks the dynamic capital to fund AI infrastructure. The "Big Five" banks and "Big Three" telcos are dividend-dispensing machines, not innovation engines. They are too comfortable to take the risks required to build a sovereign AI ecosystem.
* The Proof: Lacavera is walking this walk by acquiring Wealth One Bank (completed July 2025) to disrupt the banking sector, arguing that we need "Challenger Banks" to fund "Challenger Tech."
Pillar 2: Scaling (Pension Funds Must Come Home)
In 2017, he argued against selling startups too early.
The 2025 Update: He would target the Canadian Pension Plan (CPP) and other major funds (Teachers', OMERS).
* The Argument: Canadian pension funds are among the largest pools of capital in the world, yet they invest heavily in US infrastructure and real estate. Lacavera would argue that this capital must be repatriated to fund Sovereign Compute.
* The Reality: We cannot rely on Venture Capital to build $10 billion data centers. That requires infrastructure money. The updated pitch would demand that Canadian pension dollars build Canadian GPU clusters, ensuring that Canadian startups have access to compute power without paying a "tax" to Microsoft or Amazon.
Pillar 3: Data Sovereignty (The "Epistemic" Crisis)
In 2017, the goal was to keep patents in Canada.
The 2025 Update: The goal is to keep decision-making in Canada.
* The Argument: If Canadian hospitals, banks, and government agencies rely on US-owned black-box models to make decisions, we have lost our sovereignty. We cannot audit the logic of a foreign model.
* The "Truth-First" Policy: Lacavera would likely advocate for a "Made-in-Canada" AI requirement for the public sector—not just "hosted" in Canada, but owned and explainable by Canadians. We need to own the "weights" of the model, not just the building the server sits in.
The Realistic Path: A 3-Step Execution Plan
If Lacavera were to present a roadmap to Ottawa today, it would likely look like this:
* Mandate Open Banking (Immediately):
* Break the data monopoly of the Big Five banks. Allow fintechs and challenger banks (like his own Wealth One) to access consumer data (with permission) to offer better lending rates to entrepreneurs. This unlocks capital for the middle class.
* The "Sovereign Cloud" Tax Credit:
* Instead of subsidizing foreign EV battery plants, redirect that money to subsidize Canadian-owned compute infrastructure. Offer massive tax breaks only if the IP and the hardware are 51% Canadian-owned.
* Weaponize Immigration for AI:
* Wealth One Bank targets newcomers specifically.
Lacavera would argue that Canada’s only advantage over the US is our ability to attract high-skill immigrants. We should offer immediate permanent residency to AI researchers on the condition that they work for Canadian-controlled firms for 3 years, preventing them from using Canada as a waiting room for a US Green Card.
The Bottom Line: The updated pitch is that Canada is currently on track to become a "digital vassal state." The only way to win is to stop renting the future from America and start building the physical and financial infrastructure to own it ourselves.
***
The above are not necessarily AL's position but an attempt to summarize what they might be.
Either way, I recommend the book as a foundational must-read for those wanting to build a better future for Canada.
Happy 2026!
It was also interesting to note some of the dated arguments in this book which AL is undoubtedly completely aware of. Quick (imperfect) Gemini summary of some of these points:
***
Anthony Lacavera’s How We Can Win (2017) argues that Canada struggles to commercialize its innovations, often selling startups to foreign buyers too early ("branch plant" mentality) and failing to protect intellectual property (IP).
While his central thesis remains relevant, the explosion of Large Language Models (LLMs) and Generative AI (2022–2025) has "dated" specific pillars of his argument in three critical ways:
1. The Shift from "Venture Capital" to "Sovereign Capital"
Lacavera’s 2017 argument focused on the "scale-up gap"—the lack of Series B/C venture capital in Canada to turn $10 million companies into $1 billion companies.
How it is dated: The economics of LLMs have made this gap irrelevant by making it insurmountable for any traditional VC ecosystem. Building a frontier model (like GPT-5 or Claude) now requires tens of billions of dollars in compute infrastructure (GPUs/Data Centers).
The Reality: The game is no longer about "growing a startup"; it is about nation-state level industrial policy. The "winning" strategy Lacavera proposed (better VC incentives) is mathematically insufficient for the AI era, where only hyperscalers (Microsoft, Google) or sovereign funds can afford the entry ticket.
2. The "Data Colony" Problem replaced the "Brain Drain"
Lacavera worried about Canada exporting talent (engineers moving to Silicon Valley) and IP (patents sold to US firms).
How it is dated: LLMs have automated the extraction of value. Canada no longer just loses people; it loses its digital history. US-owned models (OpenAI, Anthropic) have scraped Canadian media, literature, and government data to train their models, effectively colonizing the country's informational heritage without hiring a single Canadian.
The Reality: We are no longer just a "branch plant" where Canadians work for US subsidiaries; we are a "data farm" where Canadian cultural output is harvested for free to improve American products.
3. Obsolescence of Specific Verticals
In How We Can Win, Lacavera placed heavy emphasis on telecommunications (5G) and blockchain as key battlegrounds for Canadian innovation, reflecting his background with Wind Mobile.
How it is dated: While connectivity is important, Generative AI has displaced 5G as the primary driver of economic productivity. The "pipes" (telecom) became commodities, while the "intelligence" (AI) became the value capturer. A strategy focused on "winning" in telecom infrastructure (his 2017 focus) misses the fact that the value has moved up the stack to the application and reasoning layer.
***
Commentary on AI and Sovereignty:
While he hasn't written a dedicated book on AI, his recent speaking engagements and short-form writing have touched on the "Data Colony" concept. He has argued that Canada is repeating its mistakes from the oil and telecom eras by failing to build sovereign AI infrastructure, allowing US giants to once again extract the value.
***
I was curious to see what an LLM would say about what AL's updated pitch would be in late 2025. Would be interesting to know if Anthony agrees:
***
Based on Anthony Lacavera’s recent activities—specifically his July 2025 acquisition of Wealth One Bank—and his established philosophy, his updated pitch to Canadians would shift from "How We Can Win" to "How We Can Survive."
The central argument would evolve from preventing a "Brain Drain" (losing people) to preventing a "Mind Drain" (losing the ability to think independently as a nation).
Here is the updated pitch, merging his 2017 concepts with the reality of the AI era.
The Core Thesis: "Stop Being a Landlord for American IP"
Lacavera would argue that Canada has misunderstood the AI revolution. We are currently positioning ourselves as a "server farm" for the US—using our clean energy and land to power American models (like OpenAI or Anthropic) that we then rent back at a premium. This creates a "Data Colony" where Canada provides the raw resources (energy, data, talent) while the US captures all the value.
Pillar 1: Competition (The "Oligopoly" is Now a Security Risk)
In 2017, he argued that the telecom oligopoly (Bell, Rogers, Telus) hurt consumers.
The 2025 Update: The oligopoly is now a national security threat.
* The Argument: A lack of competition in banking and telecom means Canada lacks the dynamic capital to fund AI infrastructure. The "Big Five" banks and "Big Three" telcos are dividend-dispensing machines, not innovation engines. They are too comfortable to take the risks required to build a sovereign AI ecosystem.
* The Proof: Lacavera is walking this walk by acquiring Wealth One Bank (completed July 2025) to disrupt the banking sector, arguing that we need "Challenger Banks" to fund "Challenger Tech."
Pillar 2: Scaling (Pension Funds Must Come Home)
In 2017, he argued against selling startups too early.
The 2025 Update: He would target the Canadian Pension Plan (CPP) and other major funds (Teachers', OMERS).
* The Argument: Canadian pension funds are among the largest pools of capital in the world, yet they invest heavily in US infrastructure and real estate. Lacavera would argue that this capital must be repatriated to fund Sovereign Compute.
* The Reality: We cannot rely on Venture Capital to build $10 billion data centers. That requires infrastructure money. The updated pitch would demand that Canadian pension dollars build Canadian GPU clusters, ensuring that Canadian startups have access to compute power without paying a "tax" to Microsoft or Amazon.
Pillar 3: Data Sovereignty (The "Epistemic" Crisis)
In 2017, the goal was to keep patents in Canada.
The 2025 Update: The goal is to keep decision-making in Canada.
* The Argument: If Canadian hospitals, banks, and government agencies rely on US-owned black-box models to make decisions, we have lost our sovereignty. We cannot audit the logic of a foreign model.
* The "Truth-First" Policy: Lacavera would likely advocate for a "Made-in-Canada" AI requirement for the public sector—not just "hosted" in Canada, but owned and explainable by Canadians. We need to own the "weights" of the model, not just the building the server sits in.
The Realistic Path: A 3-Step Execution Plan
If Lacavera were to present a roadmap to Ottawa today, it would likely look like this:
* Mandate Open Banking (Immediately):
* Break the data monopoly of the Big Five banks. Allow fintechs and challenger banks (like his own Wealth One) to access consumer data (with permission) to offer better lending rates to entrepreneurs. This unlocks capital for the middle class.
* The "Sovereign Cloud" Tax Credit:
* Instead of subsidizing foreign EV battery plants, redirect that money to subsidize Canadian-owned compute infrastructure. Offer massive tax breaks only if the IP and the hardware are 51% Canadian-owned.
* Weaponize Immigration for AI:
* Wealth One Bank targets newcomers specifically.
Lacavera would argue that Canada’s only advantage over the US is our ability to attract high-skill immigrants. We should offer immediate permanent residency to AI researchers on the condition that they work for Canadian-controlled firms for 3 years, preventing them from using Canada as a waiting room for a US Green Card.
The Bottom Line: The updated pitch is that Canada is currently on track to become a "digital vassal state." The only way to win is to stop renting the future from America and start building the physical and financial infrastructure to own it ourselves.
***
The above are not necessarily AL's position but an attempt to summarize what they might be.
Either way, I recommend the book as a foundational must-read for those wanting to build a better future for Canada.
Happy 2026!
February 19, 2018
I’m a designer but I get more excited about being part of changing a system that will impact the 99% underserved by the latest innovation in juice pressers than I do about designing a connected blender, or whatever is at the bleeding edge of what has come to embody innovation.
I don’t think innovation is about the new. To borrow from Albert Szent-Gyorgyi, who received the Nobel Prize for discovering Vitamin C: Discovery is seeing what everybody else has seen and thinking what nobody else has thought.
That’s how I felt about Wind Mobile founder Anthony Lacavera’s How we can win: And what happens to us and our country if we don’t, a book that I expect will prove to be the most influential read of my 20s (although I recently discovered Esther Perel and her writing on human connection is blowing my mind).
Canada is a unique place to do business and we don’t hear much about that, which is actually one of the unique traits of doing business in Canada.
According to Lacavera, the problem with Canadian business is that entrenched organizations are slow to innovate and compete, and innovative start-ups are quick to sell to American companies. This is a problem because Canadian companies are increasingly facing foreign competition on our home turf, and the cost of losing is being passed down directly to the consumer.
But the really interesting stuff is about how we got here: why do we have this problem?
In short:
- Our risk-averse culture
- Our vast, sparsely-populated geography
- Our governmental and tax policies
- Our stable economy
- Our relationship with the U.S.
It’s that last point that pervades our culture and economy, and really makes the Canadian context unique amongst other stable, sparsely-populated peers. We are accustomed to being late adopters of American innovations.
In fact, Lacavera so captivated me with this problem statement that I am now dedicating my Master’s research to pinpointing the unique Canadian factors that can form the unique Canadian company that will embody our unique Canadian values. Any ideas?
I don’t think innovation is about the new. To borrow from Albert Szent-Gyorgyi, who received the Nobel Prize for discovering Vitamin C: Discovery is seeing what everybody else has seen and thinking what nobody else has thought.
That’s how I felt about Wind Mobile founder Anthony Lacavera’s How we can win: And what happens to us and our country if we don’t, a book that I expect will prove to be the most influential read of my 20s (although I recently discovered Esther Perel and her writing on human connection is blowing my mind).
Canada is a unique place to do business and we don’t hear much about that, which is actually one of the unique traits of doing business in Canada.
According to Lacavera, the problem with Canadian business is that entrenched organizations are slow to innovate and compete, and innovative start-ups are quick to sell to American companies. This is a problem because Canadian companies are increasingly facing foreign competition on our home turf, and the cost of losing is being passed down directly to the consumer.
But the really interesting stuff is about how we got here: why do we have this problem?
In short:
- Our risk-averse culture
- Our vast, sparsely-populated geography
- Our governmental and tax policies
- Our stable economy
- Our relationship with the U.S.
It’s that last point that pervades our culture and economy, and really makes the Canadian context unique amongst other stable, sparsely-populated peers. We are accustomed to being late adopters of American innovations.
In fact, Lacavera so captivated me with this problem statement that I am now dedicating my Master’s research to pinpointing the unique Canadian factors that can form the unique Canadian company that will embody our unique Canadian values. Any ideas?
October 30, 2017
I really enjoyed the author's perspective on how Canada can promote innovation and entrepreneurship in our country. That being said, he took a very narrow view of such concerns, following an incredibly Schumpeterian view of the world. This book is worth the read, but its content should be consumed with a healthy portion of salt to ensure that the reader recognises the author's rather limited outlook.
October 21, 2025
It's enlightening to read a book about Canadian business, even if the story is a bit disappointing: How Canadians have a surprisingly un-Canadian-like culture of not supporting business endeavours. The title is positive, but in the end, I didn't feel I got a clear answer from author Anthony Lacavera about "How We Can Win."
December 23, 2017
First-hand account on overcoming Canadian markets and what could and needs to be done in entrepreneurship
November 20, 2022
I like to read this book bcse the word on the story was great
Read
December 20, 2022Crystal pick
Displaying 1 - 7 of 7 reviews