When Brett Barakett, HBA ’88, founder and CEO of Tremblant Capital, spoke to Ivey’s MBA and HBA students about a pivotal decision at his firm, he didn’t sugarcoat the realities of leadership.
Using one of his favourite analogies – hockey – he explained that resilience is about how you respond after setbacks.
“If you’re not making mistakes, you’re not trying hard enough,” he said. “When you get knocked down on the ice, do you sit there crying, or do you get up? What you do next is everything. You’re either winning or you’re learning."
That perspective reflects Barakett’s broader life philosophy: the real measure of success isn’t just in outcomes, but in fully engaging with the challenges along the way. He told the students that each day he wakes up determined to make it the best day of his life.
“Life is an adventure, and the journey is the reward,” he said.
Barakett’s presentation marked the opening session of Navigating Change: Lessons from CEOs on Managing Strategic Transformation, a new elective course introduced this fall by Ivey Dean Julian Birkinshaw and Lecturer Doug Murphy, HBA ’85, former CEO of Corus Entertainment. The course pairs case discussion with the lived experience of top executives – all Ivey or Western alumni.
Cases brought to life
Each class begins with a traditional case debate on a high-stakes decision. In the second half, the CEO from the case joins to share unfiltered reflections.
For the inaugural session, students analyzed whether Tremblant should launch an exchange-traded fund (ETF) – a move raising questions of cannibalization, brand dilution, and risk.
“You’ve always got somebody screaming at you that this new technology is going to change everything and that you need to go all in,” Birkinshaw told the class. “And then you’ve got a lot of other people who have a huge stake in essentially maintaining the status quo. That’s the dilemma CEOs face every day.”
After the debate, Barakett – the case protagonist – described how he decided to launch an ETF called TOGA.
“I didn’t do a survey. I didn’t ask a bunch of people. I called each client individually and said, ‘This is what we are doing, and this is why we are doing it,’” he said.
Embracing risk
Throughout the session, Barakett returned to hockey.
“What if I gave you three hockey games to play in tomorrow. The first one, you’re going to lose by 10 goals. The second one, you’re going to win by 10 goals. Neither one is much fun, right? The third one is going to be a one-goal game, maybe into overtime, and you may win or lose. Which game do you want to play in?” he asked. “All day long, I want to play the third game. I live for a good battle. Every single day I get up, I want something hard to do … I am just wired that way."
Barakett said that mindset has guided him through defining moments such as 9/11, the 2008 financial crisis, and COVID-19.
He also challenged the idea that success always goes to first movers.
“It’s always cool to be the first mover,” he said. “But in some ways, the smart thing to do is to let somebody else make the mistakes and be the fast second into the market.”
Spotting consequential change
Barakett credited Tremblant’s success to identifying companies or industries that are likely to be beneficiaries of "consequential change," whether in consumer behaviour, company strategy, regulatory environment, or a number of other dynamics, and then acting quickly but thoughtfully. This focus on disruption or substantive shifts in free cash flow generation potential led to early investments in such companies as Amazon, DoorDash, Spotify, and Uber.
“Our secret sauce is an experienced founder, good people with deep industry expertise, investment in data analytics, and serious analysis of consequential change,” he said. “Then we invest in only the most compelling ideas.”
Culture and character
Barakett also emphasized leadership qualities that sustain performance.
He recalled a compliment from a trader who said, “When I see you walking across the floor, I can’t tell from your face if you’re making or losing money.”
The lesson: emotional control matters.
“If I’m going to raise my voice or pound the table, I’m doing it on purpose, for a reason. It’s not because I’m emotional. It’s theatre,” he said.
Equally important, he added, is fostering a culture of open debate.
“You’ve got a bunch of really smart people – how do you create a culture where they can openly debate?” he asked. “What you don’t want is people leaving the room whispering, ‘You were wrong.’ That’s not healthy. You’ve got to argue it out in the open.”
Staying ahead of change
Barakett reflected on the many pivots in his career – from Procter & Gamble to Reebok to Wall Street and finally to launching Tremblant – and underscored the importance of embracing change. He described always pushing himself forward, never settling for what he had. At one point, he gave up the certainty of a seven-figure income as a ranked sell-side analyst to join a hedge fund offering a substantially smaller salary and no guarantees. Years later, as the case discussion showed, he would again embrace risk by launching TOGA. Each leap carried risk, but also opportunity.
“Change is constant. You have to adapt to it, embrace it, and take risks. And when it comes to cannibalization, strategy 101 is this: if you don’t cannibalize yourself, somebody else will. So you’ve got to keep going,” he said.
When asked whether he would have done anything differently, he offered a forward-looking philosophy.
“I try not to live with regret. That’s always helped me. I think about my life in its entirety – I always have,” he said. “Even back in the ’80s, when I was making career decisions, I’d ask myself, ‘When I’m 90 years old in a rocking chair, looking back on my life, would I regret not making this decision?’”
That sense of perspective also came through when he reminded students that there is rarely only one route to success.
“There are many paths to the waterfall,” he said.
The key is not whether you take the shortest or the most direct route, but whether you keep moving forward and stay true to your values.
Taking risks and embracing change, he suggested, is also the key to finding fulfillment beyond business.
“I’m the happiest guy on the planet. How do you live your life that way? By knowing you gave it your all in every shift, whether you won or lost,” he said.
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