Playing Business Like Poker – 13 Tips before you go “All In”

Successful entrepreneurs and poker players have so much in common. We understand that risk and reward are measured as the consequence of every action or inaction we decide upon. We enjoy the absolute thrill of winning; regardless of what hand we’re dealt. In essence we make our own luck, not by chance, but from skill. The same principles, which govern the poker room, can also be applied to the boardroom.

If you can’t afford to lose then don’t play. This is my cardinal rule. Never gamble what you cannot afford to lose. You’ll lose your advantage the minute you sit down at the table.  Your stress levels will increase and your body language has now become an open book. Other players can now anticipate your actions and can push you into making poor decisions.

Know yourself, your opponent and your odds. I am both a history buff and a student of military doctrine.  Sun Tzu, a 6th-century Chinese general wrote the most influential manifesto on military strategy, “The Art of War”. One of my favorite quotations, which applies well to this principle is “ if you know your enemies and know yourself, you will not be imperiled in 100 battles… If you do not know your enemies nor yourself, you will be imperiled every single battle.”

Pay attention to detail – keep your eyes open and an ear to the felt. Of course look at your cards, but more importantly study those sitting at your table. Study their mannerisms, their facial expressions and the inflection of their voice. Whether you’re negotiating a business deal or deciding how much you’re about to bet.  The key in making the best poker hand fold is a matter of knowing how far you can push a competitor without endangering your bottom line. This is the art of playing the player, not just your cards.

Adapt, Pivot often and overcome adversity. Never play the same game twice. Don’t become a victim of your own habits. Change your strategy, take the road less traveled and take a calculated risk. Sometimes, you will loose. On occasion, you may find yourself in a losing streak. A serial entrepreneur, just like a good poker player, will not have any issues in kicking lady luck in the teeth. Call it intestinal fortitude, tenacity or just plain stupid. Have the mindset is everything you could build it again.

Play from position. You don’t defend a castle from outside its walls.  You can’t grow a successful business without exceptional talent. Nor do you play recklessly with a weak hand or an early table position.

Poker is a marathon, not a sprint, as long as you run in the right direction. If I had a nickel for every time somebody told me they tried and failed at their business venture, I would guarantee they were running blindly into the East to catch a sunset. Regardless how passionate you are in achieving your goals, a lack of patience and planning will ultimately result in your demise. Sometimes slow is the best speed to obtain in order to achieve your goals. In the world of poker and business, timing is everything. Your goal is to be prepared when your time comes to “Go All In” and live to tell the tale.

Don’t chase the cards. Play a good hand; if you want to win don’t take shortcuts. Winners don’t play the lottery or bingo. For every $1 you earned it took you $10 to earn it.

Bet Strong but Fold quickly. You were ahead, now you’re behind. This is the game of poker and the game of life. Now you’re faced with two choices, bet or fold. You can 1) play the player forcing them to fold the best hand, which by the way does not work if they’re holding the best hand, or 2) if there’s nothing to gain, and even more to lose, quickly yield and wait patiently for your next opportunity. I have built multiple businesses and leadership teams. I was slow to hire and quick to fire if it was deemed a necessary outcome for the businesses success. This same mindset could also be applied to the businesses strategy and market position. Sometimes the best-laid plans can lead to ruin. When this occurs you can either change direction or fold the business.

Tilt Kills – Never let your emotions cloud your judgment. In business as in poker, emotions have no place in the poker room or boardroom. This is especially true with anger. This is the most destructive of all emotions. Once unleashed, irrational decisions are sure to follow. This is great for your opponents, not so great for you.

Always be professional and make friends. There is never a time where one should be unkind for unprofessional. Around the poker table, as well as in business, people tend to ally with those they like and respect.

Build your reputational bank account. Your reputation in business or the poker table begins and ends with how you play the game. The more successes you’re able to achieve, the easier the game will become. A larger chip stack and a series of winning hands yield the same result as a large bank account and a series of business successes. In both situations your competitors will fear you and your backers will adore you.

Only show your cards when it’s to your advantage. Always set the stage to your advantage. If you want to show your cards to an opponent, be prepared to pivot your game. So the next time you appear weak, when you are strong, your opponent will attack to his detriment.

Chart your progress. Record your wins, losses and mistakes. Quantum improvement begins by understanding the past failures and preparing for future opportunities.

I hope you enjoyed my outlook on poker, business and life. Please comment and don’t forget to subscribe to my blog.

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John Cataldi

Serial RainMaker
He is a creative, on-the-edge, serial entrepreneur, investor and advertising evangelist who speaks often on topics of capital raising to connecting the dots between business, strategy, influencers and market penetration. He currently serves as the Director of Business Development of US and European Markets for Macquarium, a Consumer Experience Boutique who consults on optimizing engagement and revenues for Fortune 1000 and venture backed start-ups.