Index: Money, Investing, and Side Hustles

a whole lotta Bens (US hundred dollar bills)
Photo by olia danilevich from Pexels

This particular index is centered on my lifelong hobby of side hustles, low-hanging fruit money grabs, contests and gambling for money rather than entertainment, travel hacking, and the general art and science of investing.

I am not rich, which I define to be a net worth of $25 million dollars. I’m richer than 99.9% of the writers on this platform, though. (Yes, that’s a fake internet statistic pulled out of my elbow, but I bet it’s true.) In any case, here’s an introduction to my thoughts about wealth:

Writing for Money

Just so you know, if you want to make a solid full-time living as a writer, you’ve got to walk away from any concept of FIRE or passive income. The richest authors in the world (think Stephen King) are hands-on working authors who keep putting words together long into their seventies and eighties.

No successful creative person wants early retirement. Only failures do. Writing is not a retirement scheme or a source of passive income. So if you’re a writer, be prepared to write and also — be prepared to go to a different page that’s about the work. Because you’re gonna need to work:

Side Hustles and Bonus Money

I flew around the world in first class long before I could afford first class tickets. There’s nothing like a good hustle. The opportunities come and then they go thanks to being over-used, but here are some stories to help you find your own big breaks.

When the current crisis is over, maybe I’ll lift a glass of Krug with you in the Business Class Lounge in Doha. In the meantime, here’s a taste of my philosophy:

Random Money Stories to Make You Smile

Let’s face it. Money is funny, and the stupid things we do with, to, and for money can be funny too.

Poker, Gambling, Contests, and Winning

I’ve had a lifelong hobby of winning. Not to brag. Not to say I took home the World Series of Poker bracelet or anything. But, from time to time, when the conditions were right and I had a huge advantage, I dived right in. Casino gambling is one reason my house is paid off today. It’s also why I’m banned from most casinos outside the poker room. (They don’t care about poker, because you’re taking the money from other players, not from them.)

If you have an addictive personality and can’t walk away when the odds change, skip this section. Also, nothing changes faster than contest rules and/or gambling offers. Perform your due diligence before you invest your money. Otherwise, you’re not investing. You’re gambling. And that’s no way to run a railroad.



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