I chatted with a $300M founder last week.

He's a poster child for success. Varsity football player. Ivy League graduate. Cushy job at Forbes 500 Company.

This was a man who never tasted failure.

Society admired him.

So when he started his company, he made decisions not just for their merit but for how they’d look in the eyes of others.

It crippled him.

After a year of near-zero growth, he realized that people don’t care about you as much as you think they do. Sure -- a handful might pass judgment -- but opinions are fleeting. No one truly gives a shit. So why bother?

Brazenness became his superpower. He embraced the risk of failure and made moves that others were too scared to consider.

Now his company is worth $300M.

Smart people are used to being seen as smart. They're like being admired by others. That hinders them from taking risks and asymmetric bets in their life. And when you don't take risks, you miss out on life-changing opportunities.

Imagine if Bezos never left his Private Equity job to start Amazon. Or if Musk hadn't poured his net worth into SpaceX. How different the world would be today.

Be okay with looking like (or even being) a fool.

Because the biggest fool is someone too afraid to be one.

Find me on Twitter @itsTimWijaya