All founders are a**holes. Again.

The curse of being contrarian.

A few weeks ago I wrote about why, in general, founders are assholes. 

TLDR: It’s not that they are. They become. They change. Because, play the game long enough and there will come a time when what got you here wont get you there. And nothing will change if the founder doesn’t. So he does. But he isn’t able to communicate why and how (he doesn’t even fully know himself, it all happens so fast). And for folks who came in for the OG guy, this new guy is an asshole. 

That’s one reason. There is another. Indulge me.

Two decades ago, it was unthinkable that we will live in other people’s homes while on vacation. Today, we AirBnB like we have friends all over the world and they’ve invited us.

Two years ago it was unthinkable that groceries would get delivered in 10 minutes. Now we order five times a day and operate as if it’s our birthright. 

A decade ago, I would laugh if you said I’ll get a massage and a haircut at home. Today, well, you know. 

Do you see what’s common here? Someone took a contrarian bet on how the world could/should be (not how it is), and got it right. That’s where all value in the world is created. When you are contrarian. And right.

All choices in the world can be plotted on this 2*2 matrix. 

If your are contrarian and wrong, well then the world was justified in calling you stupid. If you’re conformist and right, well then good for you, but a million others were also right  -so there’s no alpha. And if you’re conformist and wrong, which, as a society, we quite often are, well the jokes on you. Might as well have tried to be contrarian!

So yea, all value is created in that top right box. And it starts with someone being contrarian. 

Now here’s the nuance. On your entrepreneurial journey, if you want to create serious, long lasting value, you have to be contrarian and right not once, but many times over, across many business functions, over a long period of time. 

For example.

Marketeers assume that the ‘consumer is stupid’. And consumers assume that brands (and businesses in general)  don’t speak the truth (they are in it for money, not morals).

But you believe people are not stupid,  they’re just busy. And that they’re tired of having their trust broken. You believe they yearn for a 100% honest brand. One that’s not taking them for a ride. You also believe you can make a good business out of it. Great. Contrarian. Go ahead. Build it. See if your are right. 

In a world of ‘try fast fail fast’, you believe that consumers actually value brands that are first time right. Brands that don’t use consumers as guinea pigs and then call it ‘iteration’. Of course, getting it perfectly right before launch means you are slow. Slower than your competition. So they keep launching and gaining market share. Everyone (well-wishers) is pushing you to to launch faster. But no, you have a contrarian view. And every contrarian bet has a cost. Time will tell if you were right! 

Not just a brand, you want to create a culture where people are motivated by the possibility to leave the world a better place than they found it (when everyone tells you it’s all about compensation). But you take a contrarian bet. Hire for intent more than skill. Again, it slows you down. But you’re playing the long game. Only time, lots of it, will tell if you were right.

Entrepreneurship, I find, is a continuous series of choices. And a successful entrepreneur is one who continuously makes contrarian bets, and more often than not, gets them right. 

This string of successes is where the trouble starts. 

Think about every time the founder is taking a contrarian bet. By it’s very nature, the bet rubs people the wrong way.

They think this fellow has lost it. They think finally his hubris has got the better of him. They think he is too far removed from the ground to know how stupid this idea is and how badly it will fail. They think he thinks too much of himself. That sure, he might have been right in the past, but this time he is definitely wrong. 

Every time, every single time, a founder pushes through a contrarian bet, he takes on the risk of being wrong. And of proving the world right in saying that he was wrong. But he also knows, from experience, that this has happened before. He believes people can’t see the world the way he does.

And guess what, this time too, he turns out to be right. Genius.

To the world, to his team, to his investors, to critics - he did it once again. He almost went over the edge, but he pulled it off. Again!

But to the entrepreneur, it’s one more win for him against this world. And one more proof point that the world just doesn’t get it. 

Being contrarian and right is a drug. Let is happen a few times, and you’ll find the founder starts to revel in being contrarian. He loves it when people tell him he’s lost it. To him, this is proof that he is on to something. These mere mortals are shivering at the thought of this change. Of his ambition. So it must be right. 

He starts believing that being contrarian is proof of being right. And soon after, he starts believing that being contrarian is being right. 

Can you see how such a person would come across? Asshole. Always singing his own tune. Always pushing through his hare brained ideas. Never listening to good counsel. Smiling (smirking) every time someone says ‘it wont work’.  

It works till he is right. It even builds an aura around him. The man who just can’t go wrong. Until he does. Until one day he is contrarian, and wrong. 

This is the instance that turns the scale. Every one was feeling it, but now it is socially acceptable to call him an asshole. ‘Told him so. But no, he won’t listen. He thought I was being less ambitious. Or worse, that I couldn’t see it. Asshole’. 

At such times, spare the entrepreneur a thought. Yes, it was hubris. Yes, all that success went to his head. Yes, this time, he should’ve listened. But remember, the last ten times, he shouldn’t have. You should’ve.

Ironically, this one time he is wrong, is not a test of who he is. It’s a test of who you are. Are you the one who stands by him and says hey, I’d tell you I told you so, but then you could’ve said the same to me the last 10 times. You didn’t. And I won’t either. We’re in it together. Let’s be better next time.

Or you could be an asshole. 

PS: The entrepreneur here is a he, because the entrepreneur here might be me :)