Luck arrives unannounced; noticing it is the skill
Twitter came out of a failing podcast company and Square out of a lost sale. The skill is noticing such moments, which is easier to describe after they pay off.
The strongest thing you can cultivate as an entrepreneur is to not rely on luck but cultivating an ability to recognize fortunate situations when they are occurring.
The wording is loose because Jack Dorsey was speaking, not writing, and the idea is clearer than the sentence. Luck is not a plan. What a founder can develop is the habit of noticing when circumstances line up.
Dorsey’s two companies illustrate it. In 2006 he was working at Odeo, a podcasting startup whose product was being overtaken by Apple’s move into podcasts. He had carried an idea for a status-sharing service for years. The fortunate situation was the team around him: skilled people at a company looking for a new direction. He proposed the idea, and Twitter came out of it. In 2009 his former boss, the glass artist Jim McKelvey, lost a sale because he could not accept a credit card. Dorsey saw that phones were becoming powerful enough to take payments, and the two started Square.
Neither moment was lucky in the usual sense. Plenty of people work at struggling startups, and plenty of artisans lose sales to card payments. The difference was that Dorsey read the situation as an opening rather than a setback.
There is some evidence that this can be learned. The psychologist Richard Wiseman has run experiments in which people who described themselves as lucky were better at spotting unexpected opportunities, such as a message printed in large type inside a newspaper they had been asked to count photographs in. People who considered themselves unlucky tended to focus narrowly on the task and miss it.
The weakness is hindsight. Every successful founder can point to the moment that mattered, because the success picked it out afterwards. At the time, a founder sees dozens of situations that might be fortunate and cannot pursue them all. Someone who reads every setback as an opportunity will chase many and finish none. Recognizing fortunate situations therefore needs a second skill: letting most of them pass.