First You’re Lucky, Then You’re Good

Redfin and Our CEO

First You’re Lucky, Then You’re Good

In book publishing, an author who has written two manuscripts, the first mediocre and the next magnificent, will often see the two published in reverse order, with the magnificent novel promoted as a debut, and the mediocrity coming out years later.

What publishers know is that if your first effort is even slightly disappointing, no one will give you a second chance. The same is probably true of entrepreneurs, except our books are written in public, in real time, with no editors.

It matters more than we care to admit which book comes out first.

What if our generation’s greatest entrepreneur, Steve Jobs, had launched his second startup first? For anyone under 30, Steve Jobs sits alone atop the pantheon of entrepreneurs for what he did at his first venture, Apple. But when I was coming of age, Steve was merely a sympathetic figure, a sort of poet’s poet, one who had gone up the river on his next venture and completely lost it.

The company Steve founded on leaving Apple in 1985, NeXT, was for most of its 11-year history a colossal, ghastly failure, hemmhoraging money and talent. I once met one of NeXT’s engineering leaders, a Frenchman who reported to Steve Jobs. When I wondered aloud what it was like to work for Steve, the engineer answered with one word: “Air-o-wing.”

I twice had to ask him to repeat what he said, and then finally understood him. It wasn’t inspiring or profound to work with Steve Jobs. It was harrowing.

What made NeXT a failure for many years was exactly what made Apple a success: Steve’s insistence on perfection at any cost led to delays in a product almost nobody could afford, that didn’t bother to work well with anything else. It is no affront to NeXT’s Linux-based operating system, now used by Apple, to say that if NeXT had been Steve’s first company, it would have been his last.

We often remember leaders like Steve for having made the right decision at the right time, but mostly people make the same decision at the wrong time and the right time: if Hitler hadn’t come along, Winston Churchill wouldn’t be remembered as the bellicose Brit who stood up to the Nazis in World War II, but as the bellicose Brit who ordered those poor Australians to “go over the top” of the World War I trenches at Gallipoli, costing 500,000 people life and limb and Churchill his job as First Lord of the Admiralty. All of us, especially the visionaries, can be like broken clocks, waiting to be right twice a day.

Technology is littered with examples of this. Consider the great Evan Williams, whose single-minded pursuit of self-publishing took a wrong turn at Odeo, a directory of podcasts, before he hit upon Twitter. I doubt Evan would have had the capital or conviction to overcome years of struggle at Odeo if he hadn’t already been successful with Blogger.

By the same token, I feel lucky to have co-founded Plumtree with Kirill Sheynkman and Joe McVeigh before running Redfin. The three of us supported one another in Plumtree’s early dark days until a surge of sales during the boom saved the company.

Had I tried to run Redfin first, it would have failed. I never would have had the credibility to hire the engineers to open our San Francisco office or to raise the money to keep Redfin in business.

Most important, without my Plumtree experience, I myself never would have had the confidence to keep going when Zillow and Trulia launched a national version of the map-based search website we’d created for Seattle.

We celebrate entrepreneurs who fail once and try, try again. But these folks are rare and often totally insane. Some of the most talented entrepreneurs I know started their first company at the wrong time, with the wrong people, or with the wrong idea; the primary lesson they draw from their own harrowing experience is never to try again. They will spend the rest of their lives at Amazon, Microsoft and Google.

In the hagiographies of entrepreneurs, we ignore people like that, trying instead to convince ourselves that DNA is destiny. The great technology writer Sarah Lacy made her name on her first book, Once You’re Lucky, Twice You’re Good, arguing that a second success only proves that what made you successful all along was being good, not just lucky. But this is the perspective of an observer, in retrospect, trying to make sense of a sometimes-random world.

If we’re being honest with ourselves, we know that you never get a chance to be good unless you were lucky first. Sometimes I wish I could convince my friends whose first entrepreneurial experience was hard that their main problem was just the order in which their work got published.

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