Lessons from Counterintuitive Thinkers: Nassim Taleb, Rick Barry, Marina Mogilko

Everything is harder when you’re afraid of looking uncool

In basketball, free throws are gimmes.

You have all the time you need to position your feet at the free throw line, gather your concentration, and shoot an uncontested shot.

Yet so many NBA free throw percentages are terrible.

Shaq, one of the most famous players of all time, shot an abysmal 53% at the free throw line. This atrocious shooting percentage—which literally affected how many games he won and therefore had a direct impact on his salary and his legacy in the sport—could have been easily remedied with one simple adjustment: shooting?granny style.

Granny style, aka shooting underhanded, is ridiculously effective.

Just ask Rick Barry.

Rick Barry consistently shot 90% at the free throw line over a ten year career. Shooting this way is easier, more controlled, and allows for softer trajectories than one-handed free throws.

Rick Barry (pictured) made 94% of his free throws in his final two seasons

The problem with granny style is that it looks outdated and silly. No one wants to resemble their grandma when the crowd is watching.

Fear of looking ridiculous is why players don’t do it.

“I’d rather shoot zero percent than shoot underhanded. Too cool for that.” —Shaquille O’Neal

“Let me make this clear: I’m not shooting free throws underhand.”—Andre Drummond, when asked about his dismal free throw percentage

“I felt silly, like a sissy, shooting underhanded. I know I was wrong. I know some of the best foul shooters in history shot that way. Even now, the best foul shooter in the NBA, Rick Barry, shoots underhanded. I just couldn’t do it.” —Wilt Chamberlain, after giving up on shooting granny style

But the stats are clear.

Granny style shooting works.

Ask yourself: are there any counterintuitive approaches you could experiment with? Any strategies that don’t hew to standard ways of doing things? Experimenting with novel approaches is how you find better marketing, build better products, and uncover insights that others don’t.

Note that counterintuitive approaches have built-in moats; your competitors won’t emulate your strategies because they are scared of looking stupid.

Takeaway: Strategies and tactics that look dumb might be more sound than you think. The cost of looking silly is lower than the cost of being ineffective.

Beware those who look the part

Contrarian investor Nassim Taleb made an assertion that, on the surface, sounds ridiculous: If you needed a life-saving operation and were choosing between two surgeons, choose the one who looks?least likely to be a skilled surgeon.

Imagine one surgeon who looks like the platonic ideal of a surgeon: strong chin, perfect hair, confident handshake, well-kempt, authoritative voice. He looks straight out of central casting for a medical drama.

Imagine another who looks like a slob. Poor social skills, badly fitting clothes. He can barely articulate the operating plan.

Pictured: This doc might not be as good as you think he is.

Why choose the second surgeon?

Because the second surgeon has made a career by way of defying expectations. He has succeeded?in spite of?his appearance and his lack of ability to speak with confidence.

At every turn, surgeon #2 would have to deal with skeptical glances and patients doubting his skills. If he’s been able to establish a successful career while facing those adversities, he’s probably excellent.

It’s hard to say the same for surgeon #1. Incompetence and lack of skill would be hand-waved away. A lifetime of looking like the embodiment of professional excellence leads to a life on easy mode, which is?exactly what you want to avoid when this person’s skill determines your well-being.

The same concept applies to people you work with: cofounders, team members, partners, customers, and collaborators.

The less someone looks the part, the more they had to work to achieve and sustain their career and reputation. The people who don’t look like they deserve to be there are kept around for a reason. That reason is competence.

Takeaway: People who look the part may not be as skilled as you think. Consider hiring and working with those who don’t fit the mold.

Looking dumb Is temporary

Pictured: Marina Mogilko

“Oh, you have a Youtube channel! My kids spend a lot of time on Youtube.”

—a Silicon Valley investor to Marina Mogilko, 2016

Marina started her Youtube channel years before she founded her?language learning startup. She created her first videos on her Iphone 4 until she upgraded her setup, mastered the medium, and grew an audience of ten million subscribers across three different channels.

When she crossed the three million subscriber mark, she and her husband left Russia and moved to Silicon Valley to raise capital for her startup, Linguatrip. In the beginning, investor meetings were hard to come by. And when meetings happened, they didn’t go well.

Investors didn’t know what to make of her Youtube presence. Was it a quirky gimmick? A cute distraction that might take her focus away from the company?

Over five years, the conversations changed. Investors’ stances flipped.

In a noisy world with channels to customers becoming more and more crowded, attitudes about the value of having an audience shifted.

Over time, investors realized she was bringing a major asset to the table. Ten million subscribers is an unfair advantage her language learning startup had over competitors. When Silicon Valley figured out she had a direct connection to a global audience of fans, investors changed their tune.

She was ahead of her time. All it took was for the world to catch up.

Takeaway: Whether or not something is counterintuitive is a function of when just as much as what.

How I Put Counterintuitiveness into Practice

Rick Barry, Nassim Taleb, and Marina Mogilko inspired me to explore how I could be more counterintuitive in my approach to entrepreneurship education. Here’s how it played out.

I started a course for entrepreneurs and knowledge workers to learn video.

What’s counterintuitive about that?

You could learn this for free. That’s how I learned—poring through hundreds of videos, blog posts, and conversations with video experts. It took forever and I found myself going down so many dead ends. This course is for people willing to pay for a system and community that works because they know that if they don’t, another year will pass with none of the advantages that learning video provides: more customers, connections, influence, and opportunities.

Your most important videos are seen by tiny audiences. Early in my career, a personalized video helped me stand out from my competitors to clinch a $52,000 deal. The view count of this video? Four people. But they were the right four people. These are the outcomes I teach towards: business wins, not virality. I'm taking different shots, just like Rick Barry.

The classroom is your room. We run it on the internet. People learn in live Zoom sessions rather than intimidating in-studio environments. Zoom is better: learning something as challenging and uncomfortable as being on camera from the comfort and privacy of your own home is not a bug; it’s a feature.

The students start as strangers. Your friends, family, and peers don’t know you (yet) as a charismatic on-camera storyteller. And sometimes those who already know you as one way can only see you in that way. They put you in a box, just like the surgeon from Taleb’s story. When you learn alongside strangers, it’s far easier to experiment with different versions of your on-camera presence on your way through false starts and the messy middle.

So that’s how I take aim at being counterintuitive.

How will you?

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