Blind Hindsight

How many times have you heard about stories like Excite having a chance to buy Google, back in 1999, for $1 million? Or, if only someone not named Bill Gates got the rights to distribute MS-DOS for $75,000, Microsoft would have never have gotten off the ground. What if, what if.

Hindsight is 20/20, or so “they say” – it’s easy to judge a decision after its effects and consequences have been granted the soothing passage the time. It seems natural to simplify and reduce the success we see today to a binary decision taken many years prior; an opportunity was sorely missed, and things might have been different only if someone had recognized the genius.

Success comes from the perfect a perfect culmination of ideas, execution, circumstances, and plain luck. Simplifying it to anything less is a disservice.

Consider Dennis Crowley and Dodgeball. It was bought by Google after a good run, and then languished within the company while its founders tried to convince the company of its value. Eventually he left, disgusted at how little attention his product got, and started FourSquare. It’d be a year or more before Google reached feature parity with Google Local1, but they were already behind in user mindshare and product execution.

Another example would be the founder my current company, Jack Dorsey. He had stepped back from Twitter, and within months started to work on Square, creating a company from the ground up focused on his vision of simple and elegant design. Obviously he wouldn’t have had the time or inclination build another company in a completely different field2.

In focusing on the companies behind these ventures, we sometimes forget that entrepreneurs, those that are instilling their legacy in their companies, also need the right conditions to flourish. If Larry Page and Sergey Brin did sell to Excite during the early days of Google, chances were that they would not have been able to build the Google as we know it today: no crazy engineering culture; no early hiring of crucial personnel which made the company profitable and ahead of other search engines; no experiments into self-driving cars. Who knows what would have happened if MS-DOS was controlled by someone less aggressive as Microsoft3.

Of course, these success stories4 are about people who have recognized their potential and continually set themselves up to maximize success, usually by leaving the comfortable confines of a big firm to head a smaller one, typically from scratch. The culture and tone of a company can be just as important as its direction, and that’s defined from the people at the top.

Which makes these romanticized notions of opportunities bygone nothing more than sensationalist headlines.

  1. And I guess, Google Hotpot and Google+.

  2. Of course, nowadays, he gets to do both.

  3. …IBM OS/2?

  4. Steve Jobs is also on that list, although sometimes it’s easy to forget that he built NeXT upon leaving Apple.

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