I cheated in high school (a lot)

Why you should ask "why" more

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The state biology exam is going on. I'm in the bathroom Googling the answers. I end up passing. Just barely. Some would call it cheating. I call it using your resources.

Since I was in 7th or 8th grade, I inherently understood Google's impact on the world. I realized my future career would never require me to memorize math formulas, biology terms, or dates of wars.

My thinking was basically:

  • I wanted to be an entrepreneur.

  • Entrepreneurs use every resource they can.

  • Why can't I use Google to figure out exam questions?

So I Googled a lot of shit.

You can imagine what kind of trouble the "Why do I have to follow rules if they're stupid?" mindset got me into. Principal's office. Kicked out of classes. Ejected from the National Honors Society. Teachers hated my smartass remarks.

The ROI on disobedience in school is negative. But entrepreneurship and the great online game are not like school. They're more like adventure movies where a sense of rebellion is a strong signal of success.

In school, you're taught to do what everyone else is doing. You're taught to follow the leader aka the teacher. If you're anything like me, you don't blindly accept rules thrown at you. You ask "why?" a lot. You think for yourself.

All great creators are rebels.

"Learn the rules like a pro, so you can break them like an artist."

Pablo Picasso

The ROI on disobedience as a creator is extremely high.

Andy Warhol rebelled against high art in favor of "business art". Tim Ferriss rebelled against the 40-hour workweek in favor of the 4-hour workweek. Gucci Mane rebelled against college in favor of rapping.

Of course, all of them were criticized heavily.

When you're playing the great online game, people will often think you're crazy or simply wasting your time. They'll continue to believe this until you're successful at which point they'll begrudgingly say congratulations.

Most people can't see your plan long-term.

Trust yourself.

I'm 10. My Dad and I are on a bike ride. "Blaze your own trail," he says as we bike off the path and through the grass. I still try to live by that motto.

"Clear thinkers appeal to their own authority," writes Naval Ravikant. Only you know what is best for you. If I listened to my grandma's advice, I would've stayed in school. If I listened to friends who said "there's no way an English major can get into tech", I would've never tried to get into tech.

What would a future version of you be most proud of? Go do that.

"In order to be a 'thought leader,' you must be willing to LEAD WITH YOUR THOUGHTS," writes Nicolas Cole. If you want to be respected for your thinking, you must be willing to take creative risks. Maybe in corporate America, people become leaders by following all the rules. But in the great online game, people become leaders by breaking them.

I had my first TikTok blow up this week. It was a joke about Kanye and me being Jewish. It makes sense why controversial content blows up. Whether you support them or not, creators of controversial content are leading with their thoughts.

Same goes with my viral Twitter thread about "the future of Ethereum". With over 2M impressions, it got a lot of love and an insane amount of hate. But I was willing to lead with my thoughts and the right people respected that. The thread led to new jobs and even startup advisory opportunities.

Real recognize real.

"You can't please everyone, so proudly exclude people."

Derek Sivers, Anything You Want

My most opinionated essays have led to most replies — and the most unsubscribes.

Don't worry about the hate and unsubscribes. It's a natural part of the process. The internet is big enough that if you're putting out quality work, you'll find your tribe.

Not everyone is going to love a 24-year-old techno-optimist that curses a lot and Googles his way through life. I'm ok with that. I'm gonna keep doing me.