Strategy
2-3 minutes

The case for Assymetrical Bets in Life & Business

A case for taking bold, calculated risks—allocating a small percentage of time or capital to moonshot ideas that could change everything.
Written by
Roy Keely
Published on
July 28, 2025

Most of my money is invested like I'm 75 years old. I'm 44.

My financial advisor has told me this more than once. Conservative allocations, stable assets, low risk. Boring, boring, boring.

But here's the kicker: 10% of my portfolio—and a large chunk of my time—is aimed straight at the moon.

That 10% includes seed investments, early-stage startups, and yeah, crypto (which, at this point, might be less volatile than some standard brokerage accounts). It's the asymmetrical barbell: 90% de-risked, 10% crazy.

Why? Because when an asymmetrical bet hits, it can change your life—or your business—forever.

Let's talk about what Meta/Zuckerberg is doing for a second. The headlines scream insanity: $20M+ salaries for AI researchers. But zoom out. Meta's betting maybe 1-2% of its cash on AI moonshots. That tiny slice could unlock a trillion-dollar upside.

It's not reckless—it's necessary.

So here's the question: What does an asymmetrical bet look like in your business?

If you're running a $1M agency or a $100M accounting firm, how do you responsibly de-risk 90% while betting 10% on a future others can't yet see?

Maybe it's picking one niche and doubling/quadrupling down. Maybe it's building your own software to create a moat no one else can cross. Maybe it's hiring a rogue genius to build internal AI tools while the rest of the industry waits and watches.

Playing it safe is fine. It'll keep the lights on. It might even make you rich.

But asymmetrical bets? They can bend the curve.

If they flop, you survive. Maybe a few people call you an idiot... but they're likely already doing that. If they work, well... you tell me.

So—What 10% bet are you willing to make? What 1-3% of revenue do you need to go long on? And what would it take to see it through?

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