Being a Degenerate for 72 hours
Every year my wife and I take a few days away to plan the business.
No phones. No distractions. Just strategy, numbers, and thinking about where Momentum is going next.
We went to our favorite spot — Baha Mar in the Bahamas.
But somewhere between the spreadsheets and strategy sessions, we did what many people eventually do in a casino…
We became temporary degenerates.
We spent over 10 hours at the blackjack tables during the trip.
You can learn a lot about risk, decision making, and human behavior by watching people gamble.
In many ways, casinos are just a concentrated version of how people behave in business, investing, and life.
At one point a guy next to me lost six hands in a row and slammed his chips on the table trying to win it all back in one bet.
I’ve seen the exact same thing happen in business.
Here are a few lessons that stood out after hours of blackjack.
1. Timing matters more than people think
In blackjack, the “shoe” can run hot or cold.
Coming in at the right time can make or break a session.
But timing alone isn’t enough. What really matters is the combination of:
Direction (is the shoe hot or cold)
Magnitude (how much you bet)
Timing (when you jump in or step away)
Risk is always a combination of these three things.
The same is true in investing and business.
2. Complaining never changes outcomes
One thing you notice quickly at a casino:
People complain constantly.
They complain about the cards. They complain about the dealer. They complain about other players. They even complain about the drinks.
None of it changes the outcome. Complaining is just wasted energy.
In business, it’s the same.
The people who win focus on what they can control, not what just happened.
3. Luck runs out. Probabilities don’t.
You can always spot the difference between casual players and professionals.
Casual players rely on gut instinct. Professionals rely on math.
You can get lucky for a while, but eventually the statistics catch up with everyone.
Reality always wins in the long run.
4. When the odds favor you — press the bet
In blackjack there are moments when the math clearly favors you.
Those are the times you double down.
You’ll hear people say:
“Scared money don’t make money.”
And while the phrase gets overused, the idea is true.
When the probabilities are in your favor, you have to lean into the opportunity.
I’ve done this many times in business where I put the odds in my favor. For example, in 2020, when COVID hit, and others were running away from the business in fear in March, I doubled down and bought $70k/month of Zillow leads for 50% off.
While a large bet, I knew I could control the outcomes through my own work ethic. It was time to double down.
5. Never risk what you can’t afford to lose
This seems obvious… yet it’s the mistake you see most often.
People start rage betting after losing.
Instead of sticking to their strategy, they try to win everything back in one hand. It rarely ends well. I call this a “hail mary" way of doing business.
This applies just as much to investing and business decisions. If losing the bet would destroy you — it’s not a bet worth making.
6. Small edges compound
Some blackjack tables pay 6-5 on blackjack.
Others pay 3-2.
That small difference may seem insignificant, but over time it’s massive. The players who understand the math always choose the better odds. Life works the same way.
Small advantages, repeated over and over, compound into large outcomes.
7. Emotions destroy strategy
Casinos are designed to encourage emotional decisions.
They bring you drinks. They keep the lights bright. They remove the clocks.
The goal is simple: Get you emotional so you bet more.
But emotional decisions destroy good strategy. The players who stay calm tend to last the longest.
Real estate agents do this too.
Many rely on a “brand name” brokerage that charges far more instead of building their own brand — even though only ~2% of buyers choose an agent based on brokerage brand.
8. Your environment matters
Who you sit next to at the table changes everything.
Some tables are full of people having fun. Others are full of negativity and frustration. Energy spreads quickly.
This is true in casinos, businesses, and teams.
9. Fatigue creates bad decisions
After hours at the tables, people start making terrible decisions.
They stop thinking clearly. They ignore the math.
Sleep and clarity are underrated advantages.
10. Even when you do everything right… luck still matters
This may be the most important lesson.
You can play perfectly. You can follow the math. You can make the right decisions.
And still lose.
That’s the nature of risk.
But over the long run, good decisions compound and bad decisions eventually get exposed.
After hours at the blackjack tables, one thing became clear: Casinos are really just a mirror for human behavior. You see greed. Fear. Discipline. Emotion.
Casinos look like games of luck. But if you watch closely, they reveal something deeper: The people who win are rarely the smartest.
They’re the most disciplined.
And the same traits that determine who wins at the tables are often the same ones that determine who wins in business and investing.
Just with much bigger stakes and much more control in business. Every decision matters and compounds over time.
Now go out there and improve your odds!
What’s the biggest “double down” bet you’ve ever made in business or investing?
