Josh Domingues had accomplished what countless young entrepreneurs long to achieve: founding a promising company that aspires to make the world a tangibly better place. Shocked to learn that international food waste cumulatively amounted to the world's third largest contributor to greenhouse gas emissions, he founded Flashfood in April of 2016 as part of a mission to drastically reduce food waste. A once-aspiring professional hockey player with no direct industry or technical experience, Domingues was hardly the top pick to solve the crisis. Nevertheless, he set his sights on grocery stores, figuring them as not only substantial contributors to the food waste epidemic, but also practical sites to produce value for consumers, particularly those most in need. His vision driving him relentlessly onward, by November of that year, he had a working app and had secured a pilot with a specialty grocer in Canada. By mid-November, however, the dream quickly seemed to be slipping into a nightmare. Only partway through the pilot, everything was already in chaos. A lack of in-store coordination, a yet-clunky app, and an increasingly irritated district manager spelled growing disaster for Domingues. Did he pull the trigger too early in launching this venture? Maybe he should have built a more solid financial nest egg? Should he really have done this alone, or was entrepreneurship more of a team sport? To make matters more complicated, Domingues was beginning to see interest-and actual financial investment-from other sectors. Maybe he should switch to the restaurant industry, or even partner with a farmer in developing a direct-to-consumer model, and jettison grocery altogether? Despite his inspirational vision, the road that lay ahead of Domingues remained fraught with uncertainty, if only his commitment could see him through.

For more than fifteen years, successful Canadian entrepreneur and investor Kevin O'Leary had developed his brand into a global powerhouse. Since his first appearance on the Canadian television program Dragons' Den in 2006 and his meteoric rise to stardom through the hit show and cultural phenomenon Shark Tank, O'Leary had become synonymous with his penchant for telling the "cold hard truth," just as much as his investing savvy. A natural storyteller, O'Leary had long recognized the value of a powerful narrative. Now bolstered by network deals and a growing social media presence, the balding businessman had cultivated an audience of millions who eagerly await his advice on personal finance, just as much as they rely on him for entertainment. At the same time, active investments, speaking engagements, book deals, and a foray into politics bolstered his image as a formidable businessperson and thought leader. Within a decade, he had come to realize the vast potential of the virtuous cycle that underlies a successful personal brand. On November 11, 2022, news broke that could spell the end for Mr. Wonderful: FTX, a prominent cryptocurrency exchange firm that O'Leary had supported as an investor and paid spokesperson, declared bankruptcy amid reports of mismanagement of customer funds and a potential investigation by the US government. Sitting in Boston Logan Airport and watching his multimillion-dollar investment drop to zero, his phone suddenly rings: CNBC is running a national story on FTX and O'Leary's involvement, and if he wants to tell his side of the story, he has to go live on air in ten minutes. For O'Leary, the decision is more than whether to face the media. He must decide how to protect his personal brand, defined by honesty and credibility, from associations with potentially massive fraud. How should O'Leary respond? And what direction should he take his brand in the face of potential crisis?

The Canada Pension Plan Investment Board (CPPIB) is one of the largest pools of investment capital in the world and follows a rigorous "Total Portfolio Framework" in its approach to investment management. In April of 2021, John Graham was just two months into his role as Chief Executive Officer, and he must decide how to lead the organization to outperform the increasingly competitive market. CPPIB had several structural and developed competitive advantages, but with assets under management projected to grow to C$1 trillion by 2030, Graham faced the challenge of scaling the organization's investment strategy for the future. As Graham settled into the chief executive's role, would he be able to lead CPPIB to meet its strategic goals?

Wes Hall founded Kingsdale Advisors and built it into one of Canada's leading shareholder services and advisory firms. Influenced by the Black Lives Matter (BLM) movement and a series of social injustices-specifically the death of George Floyd in police custody-Hall had an idea to use his privilege, power, and position to make a social impact. He decided to risk his financial security and potentially jeopardize his reputation to launch a new venture, BlackNorth Initiative (BNI), to combat systemic racism. After an initial burst of positive reactions to the BNI, Hall was left with the questions that confront every entrepreneur: What problem am I addressing? What solution should I pursue? Am I the right person to take on this challenge? Who do I need on my team? Hall wants BlackNorth Initiative to have lasting impact after the momentum of the BLM fades. Just two months after launching BNI, Hall faced a dilemma: a leading Canadian businessman and philanthropist offered to donate $1,000,000 to the BNI if they would establish a cultural center for Black Canadians. As Founder and Chairman of the BlackNorth Initiative, Hall had a decision: should he accept the funds and build the center? Could a cultural center help dismantle anti-Black systemic barriers from the bottom up and help legitimize BNI with community activist groups? Or would the costs of establishing and running a center ultimately dilute his focus and diffuse the power of his initial idea?