Most people get risk completely backwards.
They take big risks for tiny rewards.
They blow $100K+ on degrees they never use.
They max out credit cards starting businesses they don’t understand.
They “play it safe” and wake up at 40 stuck, broke, and full of regret.
That’s not smart. That’s gambling.
Worse—it's gambling with no upside.
I’ve been thinking a lot about this since reading Thinking in Bets by Annie Duke.
Her whole thesis? Make decisions like a poker player—based on odds, not emotions.
You’ll never have all the facts, so don’t wait for certainty. Make smart bets, learn, and adjust.
That mindset changed how I look at opportunity—and it should change how you do too.
Let me give you an example.
I got a Master’s in Engineering
Why? I thought it’d be cool to innovate like the the stories I read online.
Spoiler: I never used it.
Meanwhile, I built an online community and an investment/property management business from scratch—with zero connection to those fields.
That was a high-risk, low-upside move. A total L.
But there’s another way to play the game.
It’s called asymmetric betting.
Here’s how it works:
- Small downside
- Massive upside
It’s how smart people win early.
You risk little—but the reward, if it hits, is life-changing.
Naval Ravikant (tech legend and founder of AngelList) preaches this. And it works.
Here’s how YOU can start making asymmetric bets today as a teen:
But FIRST
If you are new, welcome to OCE’s weekly newsletter curated for the ambitious youth…here are some articles you missed from previous weeks:
📈
Why No One Successful Wants to Mentor You
Read More →
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🎨
Best tools for building your passion project
Read More →
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📘
The Future Belongs to Borderless Thinkers
Read More →
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1. Start a Newsletter
🕒 Worst case: You spend a few hours writing and nobody reads.
💥 Best case: You build an audience, sell your ideas, launch products, and make money in your sleep.
2. Build in Public
🕒 Worst case: Some people ignore or judge you. Who cares?
💥 Best case: You attract fans, partners, even investors. Every failure becomes content. Every lesson becomes value. That’s leverage in the attention economy..
3. Learn a Second Language
🕒 Worst case: You sound awkward for a while.
💥 Best case: Access to new markets, cultures, friendships, and job opportunities.You unlock global opportunities 99% of people never see.
4. Start a Side Project
🕒 Worst case: It flops.
💥 Best case: You create your own job. Or a business. Or freedom.
5. Teach What You Know
🕒 Worst case: Low views at first.
💥 Best case: You build authority and earn forever from your knowledge.
6. Build a Personal Brand
🕒 Worst case: You feel cringe putting yourself out there.
💥 Best case: You become a magnet for opportunities—internships, jobs, partnerships. People come to you.
7. Write an eBook
🕒 Worst case: No one buys it.
💥 Best case: You build an asset, a portfolio, and get invited to speak, consult, or teach.
This isn’t about chasing quick wins.
It’s about stacking smart bets early.
Most teens waste their time trying to look cool or doing what everyone else is doing.
But the ones who win? They start placing bets when the cost of failure is low.
No mortgage. No debt. No kids. No one to answer to. Just time. Use it.
As Naval puts it: playing it safe is the riskiest move in a world full of leverage.
So here’s your challenge this week:
Pick one asymmetric bet—and place it.
Start writing. Start sharing. Start building.
The earlier you start, the more the odds stack in your favor.
Let’s get betting (smartly),
Like what you read? Share with friends!
PS. This summer, we are going to tackle pressing global issues and drive innovation in regions (such as your own community) where it is needed the most. Want in?
We run a summer cohort for ambitious youth (high school and undergrads) to work directly with world-class founders while learning from Silicon Valley leaders.
You can also explore purposeful opportunities through our Impact Internship Opportunities Database.
Get Curious.
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Lena
https://www.openclassroomexperience.com/
