The bad news first. Entrepreneurship is not a finite game. There are no goalposts to tell you how you're doing, or how far you’ve come. Succeeding once—or several times—is no guarantee of a rerun. Failing once—or several times—doesn’t say much about whether this is the right path for you…

Last Monday, I spent an entire day running an airtight background research operation. My target: a YouTuber who has no idea I exist — and likely never will…