The Art of The Double Down

Garrett Ransom
Jul 20, 2017 · 3 min read

“Can’t nobody take my pride
Uh-uh, uh-uh
Can’t nobody hold me down… ohh no
I got to keep on movin’” — Puff Daddy (Can’t Nobody Hold Me Down)

92 percent of millionaires don’t attribute their financial success to luck, but instead to the mindset of perseverance. 50 Cent called it “Get Rich or Die Tryin’”. Diddy coined the catchphrase “can’t stop, won’t stop”. There’s no coincidence that both have become business moguls. They wouldn’t have taken anything less than success. That’s the mindset.

In blackjack, players have the option to sometimes “double down”. Doubling down is a strategic move that allows the player to double the bet on the table in exchange for an extra card. It’s considered a fairly risky move that should be exercised with caution. Like many things in life, doubling down serves as a parallel to how many successful people approach life and one day attain financial success.

Tyler Perry lived out of his car before he got his break. P Diddy worked for Uptown Records without pay for two years. They dug deep and reaped the eventual rewards. It’s not always about playing it conservatively. The longer your “head is underwater”, the more likely that your return will be spectacular if you demand air. Persistence.

“Everbody want to be fast, see the cash
F*** around they weak staff, get a heat rash
Anything in bad boy way we smash (we smash)
Hundred G stash, push a bulletproof E-Class (ehehe)” — Puff Daddy (Can’t Nobody Hold Me Down)

Doubling down is a contrarian view in modern day society. People like to say things like “at least I tried” and “quit while you’re ahead”. According to financial winners, those phrases aren’t even in their vocabulary. They realize that there’s a direct correlation between risk and reward. The larger reward you expect, the more storms you should expect to weather to get it.

Think about people who bought more real estate during the housing crisis. Think about people who increased their stake in stocks during the Great Depression. These are the real winners. They doubled down and accepted the risk necessary for a great reward. The fewer valleys you’re willing to get through, the less likely you are to achieve massive success.

It’s okay to work a regular day job for your whole life, play smart and send enough money into investments to have a cozy retirement and die without much to pass on to your children. But in a way, you’re being selfish. You played it safe and your family, friends, community, and beyond will suffer because you weren’t willing to double down to multiply your success. The choice it yours.


What should you double down on right now? What can you do to keep yourself motivated through the valleys? Feel free to like, comment, share, and follow.

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Garrett Ransom

Written by

Faith, Family, Wealth, Data Science, Tech, and Culture.

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