Underdogs compete within a system whose rules were made by those in power. To win, you have to subvert the system. That means getting it to behave in ways its creators didn’t intend that give you an unfair advantage.

A subversive mindset takes an awareness of the system; a hunger for novelty; and a willingness to act where others won’t or can’t.

Good news: These are skills you can cultivate.

System awareness

Systems like this are all around us, but we seldom notice them. Rory Sutherland offers the example of the wine list: The waiter hands an impressive-looking binder to one, and only one, person at the table—usually the most socially dominant one. That person then asks everyone “red or white?” At this point, you’re all drinking wine. Cocktails never had a chance.

Art collective MSCHF once bought an Andy Warhol line drawing for $20,000, then made 999 indistinguishably good copies of it, shuffled the original into the stack, and sold each one for $250. To the art world, this is scandalous—but only because it’s unconventional.

MSCHF recognized that fine art is priced according to the fame of the artist, because it’s actually about bragging rights. They turned a bug (counterfeiting) into a feature, giving a thousand people a cool story to tell people about your Maybe Andy Warhol. And they changed their target market: While there aren’t many people who’d pay $30,000 for a Warhol, there are plenty who’d pay $250 for a story about a Warhol.

They made back 12.5 times as much as they spent, a 92% margin.

In wine lists and fine art, we mistake conventions for rules we have to follow. Just because something is conventional doesn’t mean you have to do it. If you own a piece of art, who’s to say you can’t sell copies? If you get a wine list, why can’t you drink tequila?

Conventions and norms are everywhere.

AI is literally a prediction engine.

Outsmart the algorithm.

Success comes from unconventional thinking.

A novel mindset

It’s not just that many rules are merely tradition—it’s that the rules don’t tell you how to win. In poker, the rules tell you which hands are strongest, and the order of play. But you win poker by bluffing, spotting your opponents’ tells, and intimidating with your cash. If money is the goal, MSCHF clearly won at Andy Warhol by defying the conventions of art.

So why don’t we think like this in business?

The second essential ingredient in a subversive mindset is a hunger for novelty that drives you to discover approach others haven’t thought of yet. Some people call such approaches hacks.

A hackgets a system to behave in a way its designers didn’t intend. When a hacker exploits a bug in software, that’s a hack. But using a Pringles can to amplify Wifi signals, or repurposing a hotel room ironing board as an adjustable desk, are also hacks.

Everyone’s already bored of what you’re doing.

So do something new.

Novelty captures our attention. Babies seek out novelty long before they can walk or talk. An “oddball” image among otherwise-bland image sequences creates a rush of dopamine—the brain chemical responsible for pleasure, satisfaction, and motivation—in test subjects.  

Novelty’s memorable. In a 1933 study, German psychiatrist Hedwig von Restorff found that when people were asked to remember a list of items, they recalled those which were distinctive and isolated more easily.

Novelty makes something seem valuable, because we assume that things we haven’t previously encountered are rare, and therefore worth a lot.

Novelty’s hard to defend against. When the UK’s Government Communications Headquarters (GCHQ, which recruits for spy agencies like MI5) covered London’s Shoreditch footpaths in recruitment ads to reach potential new hires by spray cleaning stencils over dirty sidewalks, it got attention—and wasn’t illegal. Local authorities scrambled to pass legislation, but there was nothing to remove.


A subversive mind is disagreeability. Disagreeability is one of the Big Five personality traits. It doesn’t mean being a jerk, and it doesn’t mean being contradictory simply for the sake of contradiction.

It means not caring what others think.

Wilt Chamberlain is one of the greatest basketball players of all time. He was so good that basketball had to change its rules even before he joined the NBA, redrawing the lane on the courtand banning passes over the backboard. His height and strength forced the league to pass a rule that players must keep their feet behind the line when shooting a free throw.

Chamberlain needed to dunk free throws because he was terrible at shooting them the normal way. To try and fix this, he sought out Rick Barry, who made an astonishing 90% of his free throws—by shooting underhanded, or “Granny style.”

Chamberlain played some of the best games of his life shooting underhanded, scoring an undefeated record of 100 points in one game—and making an incredible 87% of his free throws using Barry’s technique.

And then he stopped.

Chamberlain said shooting Granny style made him “feel like a sissy.”

He wasn’t disagreeable enough to do what others wouldn’t or couldn’t.

We’ve looked at hundreds of case studies spanning centuries, and one clear lesson emerges: The winners, the rebels, and the underdogs all cultivated a subversive mindset.

See the system. Find the unexpected. Act where others won’t.