Heads Or Tails – Miami Or San Diego – Gambling Stories


How the flip of a coin paved our future.

It was an August night in 2007, days before my 23rd birthday. I had just finished college, and by finished I don’t mean graduated, but finished for sure. My buddies and I had been playing online poker for about 2 years, and were starting to make some pretty consistent money doing it. 3 of us, decided that while we were young, and all had just broken up with girlfriends, to make a break from it. Out of Hunterdon County NJ, where the men are men and the sheep are scared, and into anywhere else.

The 3 conditions were it had to be warm, by a beach, and have lots of women. It was then narrowed down to Miami or San Diego, and as we did with all of our important life decisions at the time, we left it up to the coin.

You see the coin holds no bias to anything or anyone, and it rarely had led us astray. Best of all, no one could ever be blamed for the coin’s decision. It was simply the purest way to make decisions.

The Flip

We packed the car before we flipped the coin, so there was no turning back or arguing. It was either going to be a 24 or 50 hour drive.

We stood there in my friends’ driveway with the car packed with all of the essentials: clothes, guitars, cowboy hats, and enough cigarettes to kill an army/last us to the next state. My friend Bill flipped the coin, as he was usually the designated flipper, and it landed on tails. San Diego it was, and 20 minutes later, off we went.

The Trip

Near the end of our trip, we stopped in Vegas for lunch, and ended up staying for about 9 days, easily blowing through a few thousand of our ~10k bankroll.

When we arrived in San Diego, we headed toward our house in Mission Beach. It was one we found on Craiglist but had never seen, yet had committed to for 9 months. This sort of thing was pretty common for us. We in fact often had competitions for who cared about shit the least. We were all pretty good.

The Arrival

I’ll never forget the first time driving up to our house up Mission Blvd, and just knowing that we were about to embark on a serious journey. For a brief moment before we got to our place, it all hit me, and I started getting a little intimidated, but once we got to our house, we knew that not only was it right, it was fucking perfect.

We quickly got hooked up with a few friends from high school that had moved out there the year prior, and started partying right away, non stop. For about 4 years.

We had a rocky time that first year, but after receiving training from top poker players we started making good money and never looked back.

We ended up becoming really close friends with some great people, and working our $10k bankroll up to $250k+ at one point, before the U.S. government kicked online poker out of the country in 2011, forcing us to alter our life plans.

Looking back, those were some of the best years and times of my life, & I owe it all to the coin.

If you ever have the chance to live in San Diego, even for a short time, do it. It IS paradise. The coin doesn’t lie.

David Weeks

David Weeks

Once professional poker player and degenerate gambler for over a decade. Author for BetSome, US Poker School, and NJ Poker Site.
David Weeks

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