The Billion Dollar Character Trait of Ridiculously Successful Entrepreneurs

“When we first started, our dream was to make $60k a year. We thought that if we could just get revenue to that point, we could survive, have our own company, and do our own thing.” — Chris Savage, cofounder and CEO of Wistia

The following is based off my conversation with Savage on my creative podcast, Louder Than Words.

Modesty is not an adjective often associated with successful entrepreneurs.

And why would it? It’s too passive, and for a generation of entrepreneurs who wear their sleep deprivation as a badge of honor, it runs counter to the image they’re trying to convey.

They’re aggressive. They’re all in. Hustling. Fuck sleep, right?

I mean, no one ever got to any place worth going by having sheepish goals, right?

Actually, no. In fact, the opposite may be true.

How many entrepreneurial success stories have you heard that start with any of the following?

“All we wanted was [X].”

“If you told us [X] years ago it would be this successful, we would’ve thought you were crazy.”

“We really couldn’t have envisioned this type of success.”

This runs counter to the unabashedly confident caricature of entrepreneurs, doesn’t it?

But why?

Shouldn’t aggressive goals be a prerequisite for success?

How did Wistia become the industry standard for video — and raise over 1 million in funding — despite Chris Savage’s initial aspiration of simply making $60k?

How did Facebook, intended to be a networking vehicle for Harvard, become more ubiquitous than email and worth more than $200 billion?

How did Larry Page and Sergey Brin, founders of Google, almost sell its PageRank search technology for just $1.6 million in 1997? (They’re now poised to become the first $1 trillion company by 2020.)

The answer?

Modesty; Not in product development and their approach to utility, but in its potential applications.

True innovation is about serving markets that don’t exist yet or building upon ones with evolutions people didn’t even know they needed.

Therefore, the only prerequisite for success in this area is uncertainty.

THAT is guaranteed.

I recently interviewed Wistia’s Chris Savage on all things related to innovation and growth on my podcast.

Check it out and let me know, what’s more important: aggression or modesty?