Bravery Is At The Heart Of Entrepreneurship

Entrepreneurs looking for a pivot or an idea sometimes ask me “what’s hot now?” That’s the wrong question! What’s hot now is too late for you if your dreams are to be a world-changing entrepreneur: You need to create what will be hot years from now.

When I met Renaud Laplanche, and later invested in Lending Club in 2007/2008, there was no such thing as peer-to-peer finance, or fintech at all (my partner challenges me on this, and, in fairness, PayPal and others were certainly fintech businesses; it just wasn’t a startup category at the time). But Renaud braved unregulated and untested realities to build a company that became the fourth-largest tech IPO the U.S. has seen to date.

In 2009, when I invested in Dropcam (which Google/Nest later bought for $555 million), the IoT was not a thing, the connected home wasn’t connected and investors were afraid of hardware and devices. Yet Dropcam’s founders Greg Duffy and Aamir Virani saw an opportunity they believed in, in a space few cared about — and they had the bravery to pursue it.

That bravery is at the heart of entrepreneurship; the willingness to believe in your own convictions when no one else does. To paraphrase Emerson, when you believe what is true in your heart of hearts will become true for all men, that is genius.

Or to quote Reid Hoffman, someone who is both alive and a friend: “When the idea is big enough and edgy enough — it’s either madness or genius. What you are trying to figure out is which one.”

Big wins come from brave entrepreneurs.

Outsize success often comes from oddball ideas: Airbnb is held up by Y Combinator as the idea just so crazy it actually worked, and has become part of their corpus for teaching the realities of entrepreneurship. Uber was an app developed out of the founder’s personal use case and seemed more vanity than venture. Twitter (full disclosure, I still own some Twitter shares) was non-obvious to most for a long time.

A Newsweek story reported Greylock’s “deals fell into three categories: ones everyone hated, ones everyone loved and ones they fought over. It was this last group that yielded Greylock’s biggest wins.”

Big wins come from brave entrepreneurs. Entrepreneurs willing to take their world-changing idea and fight against popular sentiment and general apathy to build something great. Entrepreneurs willing to prove what’s true in their heart of hearts will be true for all.