Kevin O’Leary traces his path from a Toronto basement startup to a multibillion-dollar exit, explaining how betting on himself, embracing hard decisions, and learning from hundreds of Shark Tank investments shaped his view of what founders need to build, survive, and win.

Ambitious people often find themselves succumbing to the “curse of optionality,” says six-time business founder and Harvard Business School senior lecturer Reza Satchu. They try so hard to keep all of their options open that they underperform or have decision paralysis and do nothing at all, he says.

By committing to one of your options, almost regardless of what it is, you can buck the trend. “Actually doing the thing that others won’t do,” Satchu tells CNBC Make It, gives you a “massive advantage” and can lead to accomplishing your goals.

When Alix Earle’s publicist called to ask whether she could come to Harvard Business School—to sit in on my class, be the subject of a case study, and speak to some of the sharpest young minds in business—my first instinct was to decline. I pulled up her TikTok. I saw someone having fun, looking glamorous, going to parties. I hung up and called my daughters, and they didn’t hesitate: “Dad, you want her there.”