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the need for $100,000 of debt (http://www.personalmba.com), Josh talks about a concept called “iteration velocity.” He quotes Google CEO Eric Schmidt: “Our goal is to have more at bats per unit of time and money than anyone else.” Josh (who has an undergraduate degree from the University of Cincinnati, but who educated himself in his real-world business savvy without an MBA) writes that “When creating a new offering, your primary goal should be to work through each iteration cycle as quickly as possible. Iteration is a structured form of learning that helps you make your offering better; the faster you learn, the more quickly you’ll be able to improve.” Basically, it means, try something new but small and low-risk, see how it works, keep it if it works well, and don’t be afraid to turn on a dime (or “pivot,” as many entrepreneurs say) if it doesn’t work. It involves intentionally exposing yourself to lots of small, survivable failures, so that you can get feedback from the real world, adjusting course as quickly as possible to avoid investing too many resources down a dead-end path.

I’m amazed at how many people won’t go for their dreams because they’re scared of that 95-percent failure statistic or some version of it.

Let’s consider an analogy.

While I have absolutely no scientific data to back this up, it seems to me a reasonable guess that 95 percent of all dates are failures.

Now, imagine what would happen to our species if all people, when they heard of the low success rates of individual dates leading past the first date, freaked out and said, “OH MY GOD! I’M NEVER GOING TO GO ON A DATE AGAIN! I MIGHT GET REJECTED!” This generation would be the last.

Fortunately, when it comes to dating, humans see that there is a big difference between the high likelihood that any single date will fail and the very low likelihood that all of your dates for the rest of your life will fail.

Doing something entrepreneurial is, much like dating, a numbers game. If you can keep your financial and emotional losses low each iteration, and not jump off a building if the business (or date) fails, well then, you can keep trying and trying. Eventually, most everyone can find a creative blending of passion and money that works for them, just as eventually most everyone can find a great date that leads to something more.

Beyond the pure numbers game aspect of these two different human endeavors, here’s another parallel between creative entrepreneurship and dating: if you don’t allow yourself to get completely devastated and wiped out from a failure, you can actually learn from your failures, and thus improve your odds with each iteration.

I could insert a lot of jokes here about the countless dating blunders and bloopers in my twenties; they could fill a book. But suffice it to say, when I finally went on my first date with my wife, Jena, I had learned enough from all those blunders to avoid the clod-head mistakes of my past and to woo her properly that one spring night in 2008. And that was the date that really mattered. You only need one, in a whole lifetime.

■ DUSTIN MOSKOVITZ’S STORY

In early 2004, Dustin Moskovitz was working a twenty-hour-perweek job as a computer system administrator, on top of forty or so hours a week of classes and homework as a sophomore at Harvard.

And then there was this little side project he and some of his dorm buddies were working on, called TheFacebook.com.

It’s hard to believe, but there was a time when Facebook was not a sure thing as one of the most significant phenomena in the history of human communication and social life. There was a time when it was a few kids sitting in a dorm room, and it had sixty or seventy thousand users—far fewer users than many now-folded companies have boasted before.

“The big risk was, there were these big incumbents. We thought, if they could just clean their act up, they would surely beat us. Friendster, MySpace, even LiveJournal at the time was millions of users bigger than us,” Dustin told me.

“A guy called Adam Goldberg started CU Community at Columbia