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Esporte Interativo (EI) successfully launched and competed in the Brazilian sports television market for over 12 years. EI basically created the category (e.g., ESPN of Brazil) and came to prominence by televising the Champions League for European soccer, the National Basketball Association (NBA), and other sports content property. Since its founding, other television entities have recognized the potential for sports broadcasting which has dramatically driven up the cost of securing sports content. Edgar Diniz and Leo Lenz Cesar, co-founders and the CEO and CFO of EI, were pondering how to continue to compete and grow in an increasingly competitive space. The main decision point was whether to accept an offer from Turner Broadcasting Corporation to acquire EI.

Gerald Chertavian, an HBS graduate and successful tech entrepreneur, founded Year Up in 2000. He sought to provide opportunity via education and job training to disaffected American youth, focusing on young people in urban areas. In 10 years, he built the company from one site with 22 students to 10 sites, successfully training 1,300 students a year. However, after three years of high unemployment in the United States, Chertavian became concerned about the growing opportunity gap and wondered whether Year Up would ever make enough of an impact. In 2011, he and his board wrestled with the question of how to address this issue, and they weighed the fate of the small but highly successful Year Up program. Chertavian and his team were considering options for scale and how to maintain the organization's model.

Radically innovative thinker Sy Friedland was a decade or more ahead of the trends when he took the reins of Boston's venerable Jewish Children & Family Services in the late 1990s. A career clinical social worker, Friedland was also a visionary who knew that the future of building sustainable social services and nonprofits lay in the willingness of nonprofit workers to embrace "for-profit" concepts, attitudes and best practices. Friedland's total transformation of JF&CS enabled the agency to thrive and become self-supporting. When Friedland decided to step down after 17 years, he knew the agency could suffer in the transition and took elaborate steps to avoid crippling his agency's fundraising capacity and minimize disruption, even calling in a highest-level corporate HR consultancy firm to reduce risk and assist in on-boarding his hand-picked successor. However, because he was focused exclusively on minimizing disruption, Friedland made some crucial errors. His handling of his transition ended up causing an uproar in the board that resulted in changes in governance and policies going forward-proving that even visionaries can make mistakes.