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The Art of Risk-Taking: Building Your Playbook to Freedom



"The biggest risk is not taking any risk... In a world that's changing quickly, the only strategy that is guaranteed to fail is not taking risks." - Mark Zuckerberg



This morning, I’m waking up in Las Vegas. While many people think of the glitz and glamour of Sin City, I'm thinking about race weekend. It's funny how perceptions can vary so widely, isn't it?


With the flashing lights of the slot machines, spinning roulette wheels, and high-stakes card games, that's the epitome of risk, isn't it? I think being risky should be the focus of your playbook to freedom.


But hold on a minute. I'm not suggesting you go all-in and bet your life savings on "0" at the roulette table. That's a surefire way to end up disappointed, if not downright broke! No, the kind of risk I'm talking about is calculated, strategic, and, most importantly, manageable.


So many of us view risk all wrong. Risk is not always a bad thing. Taking risks helped me tell

my boss, “I’m leaving in 2 weeks and I don’t want or need your money anymore.” Isn’t that what you really want? Don’t you want the time freedom to do what you want without wondering how you are going to pay for it?


Back in my twenties, I took a decent amount of risk and invested all my savings into a brand-new tech company. You might have heard of it—Google. Yes, that's right, the search engine giant that has become a household name. You know you are in a good position when your investment goes from a few techy nerds knowing about it to your grandmother using the company's name in her common vocabulary.


Now, I'm not saying that every risky investment will yield the same results. Far from it. In fact, I've had my fair share of failures along the way. Like the time I jumped headfirst into the frenzy of the dot-com bubble. I watched my account double, then triple, only to watch my stocks dwindle away to literal pennies.


The key is to approach risk with caution and prudence. It’s important to step out of your comfort zone and take calculated risks, but it's equally important to not bet the entire house on a single idea or asset. Never risk more than you can afford to lose, both financially and emotionally.


If you're saying, “This guy got lucky and he bought Google once, I’ll never have that opportunity,” let me stop you right there with a couple more examples just in the past 2 years. I made enough money in Meta (Facebook) to buy a brand new Tesla with cash. Which is what I did. My JP Morgan trade replaced ½ of my salary in three months. When others were buying FRC, I was buying best of breed.


Keep repeating the things that work, and you learn from the things that did not work. But even more importantly, stop repeating the things that don’t! Let the ego go and realize you don’t have to always win!


Not all risks are created equal. It's one thing to take a chance on a promising new startup or a cutting-edge technology, but it's quite another to gamble recklessly with your financial future. That's why it's crucial to approach risk with a level head and a clear strategy.


Risk is not something to be feared. Embrace risk; it's the fuel that drives progress and innovation. Risk is the actual catalyst for growth and change.


So go ahead, take a chance, step out of your comfort zone, and see where it leads you. Who knows? I know this is how you build your playbook to freedom because if it can work for me, it can work for you too!

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