Internet, Startups

The Contrarian Age

VC Fred Wilson started an interesting conversation of few weeks ago about “the mid-life entrepreneurial crisis” in which he noted how few entrepreneurs are over 40.

His initial post was followed by many others.

I’m a first-time entrepreneur in my early 40s, so I’ve found the arguments and debate interesting.

Based on my own experience the past year, I have my own personal theory about this.

I’ve come to the conclusion that a critical attribute — maybe the most important attribute — of a successful entrepreneur is the willingness to be deeply, profoundly contrarian. The fundamental creative, productive act for most entrepreneurs is placing a bet on an idea and product and market that seems compelling and logical to them, but that others perceive as, well, not sensible.

Look at the biggest success story of the web to date, Google. Their success, in hindsight, seems so obvious, but we’ve all heard what seem like countless tales of Sergey Brin and Larry Page going into meetings in the late 1990s, and being laughed at for thinking search was relevant or interesting or likely to ever make anyone any money.

I think this is why we see more successful entrepreneurs starting companies in their 20s — it’s just easier for people to hold deeply contrarian beliefs at that age. Push an idea that seems crazy or unlikely, you’ll probably look like a romantic, rebel or revolutionary to your peers — even if you fail.

Whereas it’s harder to do this in your 40s. You are less likely to look cool and revolutionary when you’re betting on a deeply contrarian idea (i.e., an idea that your friends and family and peers will all think is ridiculous or dumb or crazy), and more likely to look like that 40-year-old bachelor on the dance floor, with a paunch, strutting your white-man overbite moves to 50 Cent.

Perhaps this explains why many startup veterans become VCs in their late 30s and 40s? It allows them to back crazy ideas pushed by young entrepreneurs, while appearing stable, reasonable and rational to their friends, family and peers.


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