The #1 Mistake Business Owners Make

Asked whether Canadian caution is a weakness, Gary Vee says the U.S. objectively produces more large companies because its laws, scale, and culture encourage risk; Canada has roughly 36–38 million people, about one-tenth of the U.S. population. He still rejects the idea that geography limits excellent founders. Shopify and Spotify show that major companies can emerge elsewhere, and Gary recounts Garrett Camp, a Canadian, proposing Uber in a Paris apartment. Funding and execution may be harder outside America, he says, but “A-plus” entrepreneurs are not stopped by being in Quebec, Calgary, or Winnipeg.

Anton describes losing $11 million on Tech Deck Live and then grossing more than $12 billion with Paw Patrol. He says the setback taught him to stay calmer as problems intensify and look for either a message requiring course correction or an unexpected future gift. Gary gives his own painful example: he twice declined to invest $25,000 in Uber because buying his first Manhattan apartment left him illiquid, despite knowing Travis Kalanick and Garrett Camp. He estimates that the missed investment would have produced about $540 million at IPO, but jokes that perhaps the mistake kept him alive.

Gary says people who receive a bad hand often dwell, complain, and point fingers, none of which changes the result. He wishes entrepreneurs “practical optimism”: a willingness to move toward “maybe” with a swing toward yes, learn from adversity, and accept accountability. He also argues that self-awareness is widely overestimated—someone who claims to be an eight may actually be a six and a half or a four. Anton agrees that the worst moments can produce the best response. Gary’s goal is not merely financial success but removing stress and anxiety by focusing on what can be learned and changed.

Asked what Canadian owners should do amid tariff and trade uncertainty, Gary says the answer remains the same even if political policies change: stop spending money on “dumb shit.” He compares tariffs with AI, recalling emergency meetings at Vayner to identify work that could be commoditized before ChatGPT became widely popular. Entrepreneurs, he says, should assess whether people, U.S. marketing, or other expenses still make sense instead of mourning conditions they cannot control. A four-and-seven offsuit poker hand still has to be played. Tariffs may disappear, and companies that become sharper during the disruption could later benefit.

Lola, who worked at Twitter during its acquisition, says she “calls bullshit” on the idea that self-awareness and good intentions reliably overcome workplace barriers. An entrepreneur recently told her that, as a young Black woman, opportunities at smaller companies might go to the founder’s friends. Gary says the problem may be the environments she has chosen, but concedes that employees are ultimately dependent on leadership, reorganizations, company stages, and conscious or unconscious bias. He offers no simple fix: the controllable response is to create more “at-bats” and optionality through a strong résumé and multiple opportunities.

On AI making workers redundant, Gary says he is willing to earn less to retain loyal employees because people are why he is in business, though he admits he is unusually talented and can absorb the risk. Public companies have a legal fiduciary duty to shareholders and may have to cut staff. He disputes the assumption that AI simply means fewer people: his strategy is to make employees dramatically more productive, arguing that a company that reduces 2,000 people to 100 while a rival makes 2,000 people operate like 20,000 will lose. His advice to workers is to get trained because humans using AI will replace humans who do not.

Gary calls AI his generation’s electricity and compares its importance with the internet for people who lived before it. At the same time, he predicts a rise in analog experiences as technology becomes extreme: dumb phones, restaurants requiring phones in lockers, live events, CDs, experiential businesses, and a drive-in theater designed to block cell service. He says he is personally “all in” on AI, using a 30-person team and AI to publish about 900 pieces of content daily, while also pursuing offline businesses. People can resist ideologically, he says, but everyone will need to interact with AI at hyperscale within ten years.

Gary’s most important executive-hiring trait is humility, expressed as self-awareness: he can work with an executive who knows who they are, but delusion produces politics and damages culture. He says businesses can remain human-centered when founders retain control, whereas boards, stock prices, or EBITDA incentives push leaders toward profit. His hardest leadership lesson came from going too far with a warm culture: underperformers became entitled, strong employees became frustrated, and firings felt sudden because Gary had not given honest feedback. He now calls the replacement “kind candor,” which he says has changed his companies and their 4,000 employees.

Anton recalls a ninth-grade teacher telling his mother he would never get into university, a moment that made him feel underestimated. Gary distinguishes feeling underestimated from feeling insecure and says people must decide whether to believe authorities who judge them; he recalls a science teacher calling him a loser, then imagining that selling baseball cards disproved the verdict. Anton says he is not motivated by proving anyone wrong or by accolades. He plays for his parents’ pride and his own curiosity about how good he can become. Gary adds that earning money should not put anyone above others; how a person treats people matters more.

Asked about sustainable ambition for a lawyer, business owner, and mother, Gary answers “patience.” There is no universal work-life blueprint because people’s partners, children, careers, and life stages differ; someone whose children leave home at 45 may have another 20-year career window, while someone who has children later may face a different season. He says work can feel like a hobby when people love it, regardless of income. Financial pressure matters, but he contrasts happy friends living on $60,000–$80,000 with people earning $900,000 and remaining stressed through excessive spending. His family had little money but was happy, loving, and content.