Why only some entrepreneurs launch startups

From what I can tell, the biggest difference between the entrepreneurs who do launch startups and the ones who don’t can be summed up in one word: naivety. The entrepreneurs who launch startups are too naive to understand why they shouldn’t.

To explain what I mean, I’ll use myself as an example. I launched my first startup 20 years ago. At the time, I knew significantly less about starting companies than I do now, but I was much more willing to drop everything and do it. Why? Because I was an idiot!

I don’t mean I didn’t score well on my SATs or get good grades in school. Instead, I was an idiot because I didn’t know enough about startups and entrepreneurship to appreciate the immense challenge of building startups. That inexperienced naivety was the key factor in convincing me I could successfully start. In my mind, it was going to be easy. I was going to tell investors my idea, and they’d write huge checks to help me build it. Once it was built, I was going to show it to people, and everyone would immediately want to buy. Plus, they were going to tell all their friends. Within a few months, I’d be well on my way toward Zuckerbergian-levels of riches and success.

That’s obviously not what happened with my first company. Or my second, third, fourth, fifth, etc. companies. Even the startups I eventually launched that were more successful than my first few weren’t easy to build. In fact, they were the hardest ones. As a result, each experience building new companies made me less likely to launch another. In fact, at this point, I feel like I know too much about startups to want to build more, so a lot of factors would have to convince me to pursue a new venture. Simply put, I’m just not as naive as I once was, and that’s why I won’t launch startups without significant evidence it’s a worthwhile opportunity. As a result, I’ve probably missed out on pursuing startup opportunities I should have.

Being naive doesn’t have to be a problem

Unlike me back when I was stupidly launching my first startups, the founder I told you about at the beginning of this story has wonderful traction. It’s the kind of traction I’d need to see before I’d be convinced enough to go “all in” on a new company. Despite all this success, she’s hesitating. Why?

Turns out, she’s hesitating for the same reason I, as a young entrepreneur, thought building a startup was going to be easy: She’s naive. She’s too inexperienced to understand or appreciate how much traction she has and why she should build a company.

It’s a strange paradox. Some founders are so naive, they don’t know they shouldn’t “go for it.” Other founders are so naive, they don’t know they should.

Recognizing this challenge, I gave the founder I was meeting with the best advice I could, and it’s the same advice I’ll share with anyone else reading this and wondering whether or not to pursue their entrepreneurial dreams.

“Embrace your naivety,” I told her. “Don’t be afraid of the fact that you don’t know enough about building companies because your naivety is what will give you the courage to do great things. It’s what will help you see opportunities that more experienced people overlook. And it’s what will keep you going when everyone else tells you your idea will never work.

“At the same time, appreciate the fact that your naivety won’t last forever. Eventually, you’ll learn more about building companies and become less naive. That’s a good thing, too, because it’ll help you build better companies in the future.”