♟️ The Metagame #032: What Are You Willing To Risk?

Today’s edition is all about risk—how to manage it, why it’s useful, and most importantly, when to take it.

Here’s what’s in store for today:

• The hidden value of risk

• How to manage uncertainty like a pro

• When playing it safe is actually the biggest risk

Read time: 4 minutes

If you knew you could never fail…

What would you do?

For me, I’d play in the highest stakes poker tournaments I could weasel my way into.

No second-guessing. No sweating over bad beats. Just pure, fearless play.

Now, while it’s fun to dream, let’s snap back to reality.

Risk is everywhere—failure is guaranteed.

No matter what you do, at some point, you’ll lose.

In poker, even the best players in the world go broke sometimes.

In baseball, a .300 career batting average can get you into the Hall of Fame—but that’s still failing 70% of the time.

And in life? Well, if you’re never failing, you’re probably not taking enough chances.

Failure and risk are out there.

But here’s the thing: risk isn’t something to fear—it’s something to understand.

Risk is the Price of Admission

Everything worthwhile comes with risk.

Want to build a successful business? Risk.

Want to invest in stocks, crypto, or real estate? Risk.

Want to ask someone out? Yep, still risk.

There’s no escaping it.

So instead of trying to avoid risk altogether (which is impossible), the real skill is learning how to manage it.

Smart poker players don’t shove all their chips in on every hand. They take calculated risks based on probabilities, psychology, and long-term expected value.

Smart investors don’t throw their life savings into meme stocks based on a hunch. They diversify, hedge their bets, and play the long game.

And in everyday life? The best decisions come from weighing risk vs. reward—not from avoiding risk altogether.

The Hidden Cost of Playing It Safe

Here’s the paradox:

People think avoiding risk keeps them safe.

But in many cases, playing it safe is actually the biggest risk of all.

• Staying in a soul-sucking job because it’s “secure”

• Never starting that business, project, or side hustle because it might fail

• Holding back on opportunities because they feel uncomfortable

Avoiding risk doesn’t prevent failure—it guarantees it.

Not failure in the sense of dramatic collapse, but failure in the sense of stagnation. Never growing. Never seeing what could have been.

There’s a reason poker players have this saying: “Scared money don’t make money.”

Inaction has a cost. Playing it safe has a cost. And often, that cost is greater than the risk itself.

The Art of Risk Management

So, how do you take risks without being reckless?

For starters, you need to understand what’s at risk.

In poker, we like to ask ourselves, “How many chips do I need to risk vs. how many chips can I win?”

If the pros outweigh the cons, then it could be a profitable move.

But if we stand to lose more than we feel comfortable betting, it might be best to test our luck another time.

Risk management also requires you to diversify.

You never want to take a risk that can lose you everything. This isn’t just for poker. Whether you’re investing, starting a business, or playing a game of monopoly—risk of ruin means game over.

You never want to let one maneuver wipe you out.

And lastly, patience is key.

Sometimes, the best move is to wait.

The best traders don’t try to time the market. They wait for profitable opportunities and try to take advantage when the time is right.

Trying to force a trade is a surefire way to lose in the long run.

Risk isn’t just something to tolerate—it’s something to understand and embrace.

Every great opportunity, every breakthrough, and every significant win comes from a willingness to take the right risks at the right time.

So the real question isn’t how do I avoid risk?

It’s how do I use it to my advantage?

Because if you can answer that, you’ll be ahead of 99% of people.

Quote of the week

Thanks for reading!

If you have any questions, hit me up on LinkedIn or on 𝕏 at @sam_starkman, or feel free to reply to this email!

— Sam