Let’s talk about losers.

A couple of nights ago, Dave Duchovny was on The Late Show with Stephen Colbert. He was promoting his new book “Bucky F*cking Dent”. Bucky Dent had hit a three-run home run to give Yankees the lead in the 1978 playoff series between Yankees and the Red Sox. This was surprising because Bucky Dent was not at all known for hitting home runs. The Red Sox fans were in disbelief of losing to “Bucky F*cking Dent”. Duchovy mentions that Bucky “F*cking” Dent reminds the Red Sox fans of their loss. And since that’s what his book is about (losing), the title seems apt.

He discusses loving losers. He talks about the fact that everyone loses more often than they win, the culture of highlighting only the wins and the fact that losing only makes you more human. So, we are all indeed, losers.

In a society where only the wins of some losers (we are all losers, remember?) are celebrated, what can we learn? Not much, if you focus on where all the cameras point to. But, somewhere in the dark alleys, far from the spotlight, there lives a different type of loser. This loser has lost plentiful, but without having his big win. Here, in the darkest of alleys, you just found your guru.

People get so caught up on the Zuckerbergs of the world and seek to learn only from them. I say, screw that. Make the guy who missed the big shot your sensei. They are easier to find and can teach you more. Most of them have not forgotten the loss and have thought about it a lot. Talk to the guy whose business didn’t make it. He will tell you why it didn’t and the nuances of seeing success in your business. Talk to the guy who didn’t get the girl. He will tell you not to be “a dick” or an egomaniac all the time. Talk to the guy who didn’t get his dream job. He will tell you how he should’ve prepared more.

Apply the same philosophy in the current start-up ecosystem and things start to make sense. The majority of start-ups don’t make it. Some are DOA, some last a few months and some make it a couple of years. But, a lot of them eventually fail. Finding patterns in these failures is often too easy. The reason might be expanding too soon and too aggressively or the market not being ready or picking the wrong team. The reason could be more subtle; ones you won’t know until you inquire.

If you want to pursue something difficult, talk to people who have attempted the same and have lost. Some of them will complain about bad luck, but if you pester them long enough, you will get the truth out of them. “I maybe could have better here and there”. And that is where you gain the most valuable insights. Be careful, though. They might semi-consciously discourage you from the pursuit. Take only information away from these conversations and no emotion away because more often than not, the emotions are anger and repentance.

Let me be clear, I am not against learning by making your own mistakes. But, learning from the mistakes of others is often easier. So, for once, let’s talk about the losers.

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