Leveraging Failure (Part 2 of 4) Retired on the Beach to Criminal

October 15th, 2009 → 2:00 pm @ Andrew

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The Rest of 2004 Through 2005 [Diving into Internet Marketing]

After the demise of my stillborn career as a hedge fund manager, I was pretty much clueless as far as what to do. I had some meager savings in the bank and some credit cards with available balances. What I didn’t have was a plan. I was at square zero. I had an anti-plan. I’d rather die than get back into the sales world with the trappings of my former life. To conserve funds, I didn’t even use gas to drive to the library. I surfed the internet for any possible way to make money.

I eventually stumbled upon affiliate marketing. This was during the poker craze and online gambling was ultra hot. I played around with some ideas, but never made any money. I’d also started doing a little online gambling myself. One of the things I soon realized was that it was a major pain to get money in and out of the accounts. Various methods would take a week or two from deposit to play to withdrawal. Out of necessity, I became well versed in the nuances of each payment method. It turned out that the sites I used for gaming were influenced more by the payment methods they accepted than the graphics or other experiential differences. The odds and bonus levels varied from one to another and those were the only things I valued more than the ease of getting money in and out.

The flash hit me after a few PBR’s (measured by the pitcher, not by the glass) at the Matador in Portland, Oregon… Flip the idea of rating casinos on experience and bonus around… Rate them based on payment method. It took me a while to put this into practice and tweak things, but I eventually saw results from it. That was a good thing, because I’d already planned to move to Panama and some sort of income was long overdue.

2006 [Panama]

I shed the bulk of my belongings and boarded a flight to Panama with a laptop bag carry-on and whatever else I could fit in two checked bags. Soon after arrival, I set out looking for an apartment. I eventually found a cool place with way more square footage than I could fill for $300/month. For those familiar with PTY, it was on Calle 13, a block and a half off Parque Santa Ana… A.K.A… El Chorrillo. For those of you not familiar with Panama, it’s probably best that you not visit El Chorrillo.

I’m not writing this as a travelogue for any particular place, so I’m going to gloss over most of the details. The important part was that I waited for months for my internet to be installed. It never was. My days consisted of taxi rides to areas of the city where free wi-fi could be found. My workweek was less than four hours. Well… Only if you didn’t count the online gambling. I worked a few hours on my sites here and there. I was regularly making money gambling, but it wasn’t a lot and I didn’t look at it as a sustainable investment.

Do you remember where you were and what you were doing on October 13, 2006? I certainly remember where I was and what I was doing when I loaded up Yahoo! News to check the headlines. I was sitting in a metal chair outside ClaroCOM sucking down some free internet. I was still frozen in the same place at least 30 minutes later after having read that President Bush had signed a law making just about everything relating to payments involving online casinos illegal and punishable under Federal RICO statutes. For the second time, I was out of business. When I went to withdraw my own gambling funds a few days later, I found the holding company had frozen all access. When I was to receive my affiliate payout a few days later, I was told that they couldn’t pay me because I was a U.S. citizen. It wasn’t much, but $800 affiliate checks every couple weeks go a long way in Panama.

Back to square zero… In a foreign country. Unlike the last time this happened, I had all sorts of other plans this time. I was already working on some of them. However, barring a miracle, I wasn’t going to be able to survive long enough to see any return from them. I managed to find a casino that would take deposits from U.S. citizens. As it turned out, the law was designed to go after payment processors and banks, not individual gamblers. As a gambler, I was sort of safe, but as a marketer, I could have been prosecuted as “aiding and abetting”. I never resumed the marketing, but I did manage to make a couple hundred bucks here and there playing poker. Regardless, it soon became apparent that no miracle was going to come and I’d have to head back to the states to re-trench.

The miracles did come when trying to get back to the U.S. The first miracle was of the negative sort… The airline I had a return ticket with had declared bankruptcy after my arrival in Panama and refused to let me reschedule. Through the miracle of friends, I somehow managed to get back to Portland on December 30, 2006. 2007 begins with my non-triumphant return to an expensive country with about $37 in the bank and virtually no possessions. This should be fun!

Part III