Dec 10, 2012 · 4 minutes

If I were to live my life exactly 10 times -- and in each of those instances, I had an identical upbringing and education up through the time I entered college -- what would my various career outcomes have looked like?

Obviously, it's impossible to know, but here is my best guess:

In five of those lives, I would have been a banker or corporate manager. It's not a job or lifestyle that I would have loved, but deep down, I am risk averse. And I was always terrified of providing less for my children than my parents provided for me. To me, the certainty of financial comfort might well have exceeded the dream of wealth, even if that dream were ever so attainable.

In two of those lives, I would have been a professor or a journalist. Obviously, I enjoy writing, and I also like teaching. This path was one that I ultimately decided against, because there are a lot of issues with being a teacher or a writer in the modern day. But these issues didn’t always exist, and in a previous century, this might have been my most likely outcome.

In two of those lives, I would have been a lawyer or politician. A dirty secret of mine is that I have truly enjoyed all the legal wrangling that came with being a founder. Too bad I almost failed my Political Philosophy class in college. The practice is fascinating, but the theory bored me.

And, in one of those lives, I would have been an entrepreneur, which is what ultimately came to pass. As a consequence, I meet a lot of great entrepreneurs with whom I don’t share a deep kinship.

People often tell me that they “were born to be an entrepreneur,” or they proudly wear a Serial Entrepreneur badge on their lapel. And I have a lot of respect for people like that.

But I’m not a member of that fraternity.

I’ve started exactly one company in my life. And I started it for exactly one reason — my friends and I came up with a single idea with which we fell head-over-heels in love. And if we hadn’t come up with that idea, then I would have probably kept my job in Management Consulting, where I was content and performing well. And I would have gotten an MBA after that, and who knows what would have happened next. Probably the “5 out of 10” outcome.

I’m not a venture capitalist. But if I were one, then I would try to figure out which of my prospective investees came from a similar mindset. How many times out of 10 would they have found themselves on the entrepreneurial path? Once? Twice? Any more than that, and I would wonder if they were passionate about their idea or passionate about wanting to be an entrepreneur. Big difference there.

Over the years, I have had a chance to meet with a lot of great entrepreneurs at the very genesis of their adventure, but the one who has achieved the most success so far is Alexa Hirschfeld of Paperless Post. Just like me, she had a comfortable job before starting her journey. She was Katie Couric’s personal aide. And with her Harvard degree, Alexa could have done a lot of things.

But she and her brother James had an idea one day. And it was a very good idea. It could not be described as “70 percent Twitter, 20 percent Groupon, and 10 percent Foursquare." Nor was it “a Facebook for _______s." And when it came time to start the company, she had never before assembled an engineering team. And she wasn’t one herself. That’s why the two of us were put into contact in the first place -- because a mutual acquaintance had witnessed the same cluelessness in me, just a year earlier.

But execution is never an obstacle to an outstanding idea, especially when it is entrusted to a truly smart and devoted person. And Alexa and James figured it out.

In truth, I don’t know the Hirschfelds that well. But I’m convinced that Alexa would not have been an entrepreneur 10 times out of 10. Or eight. Or six. Or four. I think she would have been incredibly successful 10 times out of 10, but the thing that pulled her from the proverbial customs house was simply a great idea that needed — no, demanded — to see realization.

Silicon Valley does not have a “Series A Crunch” — effective today, I refuse to read any more articles or partake in any more discussions on that matter. What Silicon Valley does have is a “too many engineers think that they need to start a company” problem. And fed up bankers want to start companies too. As do disgruntled college grads.

What is your motivation to start this company?

It’s the question that an investor should ask every founder. And, moreover, the investor should pick and pry and wrestle with that question for 10 or 15 minutes — until he or she truly knows why this founder is about to jump into the deep end... Even if it means that the investor skips the part of the deck with the graphs. Or skips the part with the market pie charts. Or never makes it to the bullshit financial projections in the back of the deck.

[Illustration by Hallie Bateman]