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Losing $1 MILLION gambling


You’ve seen me win at gambling plenty of times. But how much money do you think I’ve lost over the years? A million? Two million? I don’t keep track precisely, but by my estimates, it’s probably closer to three million dollars. Yikes! The first million was definitely the hardest. Today, I’ll let you know how long it took me to lose that money, how I lost it, and whether or not it was worth it – the answer to that last one might actually surprise you.

First of all, it’s important to keep things in context. Gambling away my first million took me about 10 years to do, and I’m not proud of it. But I’ve lost way more money in much faster time in the business world. Granted, in business, I’m still significantly up overall – and with gambling, I’m down – but the main point here is that being up a million or down a million (especially over the course of 10 years) doesn’t make or break me because of the business volume that I do. I mean, there were a few years there where I lost several million per year during downturns after the ringtone boom, but I still managed to keep my company alive. Technology and internet innovations are never the same for more than two years, so you have to keep reinventing yourself if you want to stay afloat.

Unfortunately though, reinventing yourself won’t do squat to help you at the casino. Long-term, the house always wins. As you probably guessed, most of my gambling losses haven’t been on blackjack, or roulette, or craps, but on high-limit slot machines. Back in the day, I used to spend most of my money on the big dollar reel machines. But in the past decade or so, I find myself more drawn to the interactive games, like Black Widow, so that’s where you’ll usually catch me losing (or, often enough, winning too). Some people think that I’ve lost the most money on my $1,000 bets, but that’s not true – when I’m spending that much money per spin, I’m generally being much more cautious. Psychologically for me, there’s something about losing $250 - $500 a spin that just isn’t as scary as $1,000 per spin, so I’ve lost way more on my medium-sized bets than my massive ones.

But here’s the big question: Was it worth it? People think it clearly must have been worthwhile – after all, I’m still playing slots all the time, right? WRONG. I’ve always said that if I could have all the money back that I lost, I wouldn’t gamble again. Surprised? You shouldn’t be. I love playing slots, but losing a million dollars in ten years? I do not recommend going that route.

If I could have all my losses back again, I’d probably invest more into real estate instead – that’s still a gamble, of course, but there’s way less risk. Obviously, losing that much money on slots hasn’t been all bad, or I would have quit long ago. After all, if I never played slots at all, you wouldn’t have my videos to watch, and you probably wouldn’t even be reading this blog post right now, so that’s something, right? Look, it’s never fun to lose, but that doesn’t mean you shouldn’t ever take risks for fear of losing. You could lock yourself in a closet your whole life and be safe, but where’s the fun in that? As long as the money you lose at the casino isn’t money you need to survive, the pain isn’t too sharp; the highs from the wins can still balance the lows of losing, making the entire experience fun overall. And a fun life is a fulfilled life.


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