In last Sunday’s New York Times, Kate Losse looked at how failure is becoming a compelling theme within the startup world.

Rather than being a negative, failure is now a positive because it is how innovative products and services are developed. Fab, for example, isn’t a colossal failure because it burned through $325-million in venture capital. Instead, it provided its founders with valuable knowledge about how not to build an e-commerce company. This is insight that can be applied to future startups.

When a startup is successful, the entrepreneurs involved are treated like rock stars. This includes entrepreneurs who attracted a lot of venture capital, entrepreneurs whose startups were acquired for lots of money, or entrepreneurs that  established a viable business.

These entrepreneurs are treated with reverence because somehow they are smarter than the rest of us. They managed to beat the odds. They saw opportunities that others missed, or made decisions that were brilliant, prescient, timely or amazingly effective. These entrepreneurs are superstars while the rest of us are uninspiring journeymen.

But here’s a question: Are “successful” entrepreneurs good or lucky? 

Are successful entrepreneurs smarter or better, or did they find themselves in the right place at the right time or – as Kate Losse points out – did they have the right connections?

The difference between successful and unsuccessful entrepreneurs may have nothing to do with their strategic or tactical skills. It may have everything to do with luck or persistence. If you roll the dice enough times, you will eventually get a seven or 11.

Here’s one scenario: Drew Houston is a startup superstar because he turned Dropbox into an ultra-popular file-storage business. Dropbox wasn’t the first file-storage business and probably not the best but, for whatever reason, it exploded. Did Houston simply develop a better mousetrap or did he get lucky by tapping into Reddit to ignite a community?

The same goes for Brian Chesky and Joe Gebbia who super-charged Airbnb’s growth customer acquisition by using a brilliant hack on Craiglist. Were Chesky and Gebbia better or smarter entrepreneurs, or lucky? Or what about Stewart Butterfield, who struggled to turn Tiny Speck into a business before making a last, desperate stab with software called Slack? Was Butterfield smart or lucky? 

Another angle to successful entrepreneurs is what they do after creating a successful startup. If they can do it once, surely they should be able to do it again, right? 

It is  fascinating to see how entrepreneurs get the benefit of the doubt from investors because they were successful before. It’s like these entrepreneurs discovered a secret formula so it makes sense to support the next thing. But maybe these entrepreneurs just hit the jackpot. One day, they discovered the “Golden Ticket” that changed their lives. Maybe they are not smart or creative but extremely fortunate.

I would hazard to guess that entrepreneurs who have a wild success will struggle to be anywhere near as successful again. Some of them will keep trying because they are hard-core entrepreneurs. Some of them will stay in the game as investors who have enough capital to support enough startups to find another winner. Some will struggle while slowly losing their lustre. And some will appear on TV as entrepreneurs “rock stars” who can decide in minutes whether a startup has any prospect for success.

As much as people are beginning to celebrate failure (and hold conferences about it), it is important not to over-celebrate success

In many ways, success is elusive, magical, fleeting, fascinating, exciting and inspiring. We love success stories and love successful entrepreneurs. But it is important to have perspective when looking at entrepreneurial success. We need to remember there isn’t a secret formula or people who are successful because they are smarter, better, faster, etc. Sometimes, they’re just luck.

Are successful entrepreneurs smart, lucky or both? What is it about successful entrepreneurs that makes them successful? And do we over-celebrate success?

More: Audrey Soussan asks whether entrepreneurs are made or born, and then looks at four different kinds of entrepreneurs.


 If you’re looking to jump-start your startup marketing, I can help you make it happen – everything from messaging and brand positioning to strategic planning and content development. Here’s how you can explore the different ways we can work together.

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