6 Things I Would Buy And Immediately Regret Purchasing If I Had Money

To paraphrase Lyle Lanley, who is arguably the greatest one-shot character from a “The Simpsons” episode ever (from the classic episode “Marge Versus the Monorail,” which is arguably the greatest “The Simpsons” episode ever): “A postgrad with money is a little like the mule with a spinning wheel; no one knows how he got it and danged if he knows how to use it.”

I think that at the beginning of our careers, we spend a lot of time chasing money and trying to get a promotion to get to the next level. We all want to be like the our business idols who are at the top of their respective fields, idols such as Mark Cuban, Donald Trump, Lorne Michaels, Steve Ballmer, Dan Bilzerian, Warren Buffett, Jimmy Buffett–whoever. These men own professional sports teams, airplanes, Fortune 500 companies, and pretty much all the things every kid grows up wanting. However, I feel as if there are certain things that, if you had insane amounts of money, you think you might want, but they would turn out to be a lot more trouble than they’re worth. Here’s what I mean.

A Big-Ass Yacht


On the surface, a yacht seems like a great purchase: all the fun of a pontoon boat combined with the luxury of a cruise ship and being more like a private hotel room than, well, a pontoon boat. Think of all the Bilzerian-level parties you could throw on this thing…if only you knew that many hot girls or could grow a beard.

But then you have to realize a Yacht is a pretty terrible investment. You’re literally taking something that costs upward of $10 million and throwing it into the ocean, which will eventually corrode it with barnacles and salt water, or kill you with its mighty ocean currents, storms, tidal waves, and the Kraken. Aquaman can’t save you–and it’s not because he’s not real, but probably because you think he’s lame, and he knows it. Also, your vessel will attract pirates like, well, blood attracts sharks. How many times can you pay a pirate’s ransom, no matter how wealthy you are? Also, boat fuel is incredibly expensive. You’d throw away thousands every time you used your boat, especially if you sail it to…

A Private Island


Your very own private island. How cool is that? An entire landmass of beautiful, tropical ocean property, and nobody lives there but YOU. There are no police breathing down your neck–just private security you hire to make sure things don’t go straight to hell. The government? Screw it. If you’re rich enough to buy a private island, you can make them look the other way, too. Forget about booking a hotel room and having to deal with other people. You can just chill in your own house like Jay-Z and Beyoncé on their island in the Florida Keys, Leo DiCaprio’s island off of Belize, or Eddie Murphy’s island in the Bahamas. Freaking EVERYBODY has his or her own island, so why not you?

I just have one major question when you buy a private island. How the hell do you GET anything there? Like, people have big-ass houses built on their islands, but where do those building materials come from? Cargo ships? That must be expensive as hell already. Then how do you get basic things like mattresses, sheets, pillows, towels, furniture, TVs, video games, and all that stuff out there? You think private islands are wired for FiOS? How do you even have cell signal or Internet out there? And what if you’re hungry and want a pizza? I don’t think Domino’s delivers out there. There probably isn’t even a Papa John’s for hundreds of miles. I don’t want to be anywhere that pizza is not.

A Basketball Team

Eddie - Whoopi Goldberg

Okay, a basketball team. Now THAT’S something you can get behind. I mean, you’ve been a sports fan all your life, so imagine that someone comes to you with the opportunity to buy part (or all) of a basketball team. You kind of have to say yes, right? Free games whenever you want, influence over draft choice, rotations, hiring coaches, uniforms–crazy stuff like that. You want to do everything? Buy a team. Also, your kids’ friends will think you’re a god.

“JayTas? Donald Sterling on line two for you.” Ugh. Let’s not even get into that whole mess. Ignoring recent controversies, are basketball teams ever really worth it? Yeah, sure, you pay a lot of money upfront for a team and then you think you’ll make money hand over fist from ticket sales and revenue. HA. WRONG. That barely keeps the lights on in the arena. Once you factor in player salaries, coach salaries, luxury taxes, and various other expenses, your team may end up operating at a loss…and then guess who they’re gonna call for more money? You. It’s almost not even worth it. Buy a team at a low cost, create a controversy, and sell it for 160 times what it’s worth. Yeah, I’m crying for the Sterling family.



The first appearance of Superman in Action Comics 1? Check. Honus Wagner’s baseball card? Check. Babe Ruth’s first home run bat? Check. Lightsaber actually held by Mark Hamill in “The Empire Strikes Back”? Check. Ted Williams’ frozen head? Uh…working on it.

Memorabilia is really, really cool to have, don’t get me wrong. Most of the things I mentioned above have and will continue to actually appreciate in value as the years go on. But that’s the kind of shit that can become a wacky obsession (see: Will Ferrell in “The Lego Movie”). It’s cool to stare at and go “Neat!” but after a while, it’s really just something you can say you have and then you can look at it every now and again. You only have it for the remainder of your lifetime, and if, say, you eventually leave these precious objects in the hands of your kids after you pass on and they have no idea how much the stuff is actually worth, your kids will get swindled out of priceless treasures. And they’ll resent you well after you’re gone. They’ll stop paying to keep your gravesite maintained and neighborhood kids will spray paint “Boner” on your tombstone.

A Solid Gold Toilet


For the person who has everything and doesn’t think his shit stinks, this is something he can get that’ll make his turds even LOOK nice as well. Kim and Kanye spent $750,000 on four gold-plated toilets for their house, which doesn’t even come close to the $5 million, 24-karat toilet that can be found at Hang Fung Gold Technology Group in Hong Kong. If you want to crap in the lap of luxury, look no further than a gold toilet.

But do I even have to tell you why you’ll regret this decision? You’ve heard of “pissing away money,” but you’re literally pissing ON money. You’re shitting all over $5 million. And then if it breaks, do you think the Home Depot has solid gold parts for a solid gold toilet? Lowe’s isn’t THAT high end. A solid gold toilet might seem like a solid purchase, but it honestly seems like a really crappy investment.

The Combat Training and Weapons Necessary to be a Superhero
“Criminals, by nature, are a cowardly and superstitious lot. To instill fear into their hearts, I shall become a bat, and then with my parents’ inheritance money, buy all this martial arts training and build a bunch of awesome toys like boomerangs, a car that looks like a bat with rocket jets and a CAVE!!  Oh man, this is gonna be sweet.  I really miss my parents though.”
Would it be cool to be a superhero like Batman?  Absolutely.  But it is WAY more work than is possibly worth it.  I mean, look at you, you’ve got a beer gut and you just ate a whole personal pan pizza. You look like a fat slob, and that shows in spandex.  When was the last time you even went to the gym, let alone prepared yourself for any semblance of the physical, emotional and psychological rigor required to be a masked vigilante.  Also, what would your schtick be: “Middle-Management-Man”?  “Business Guy”?  “Dr. Doctor”?  Just stop.  Also, when people see you in a costume, they’re gonna rise up and start trying to take you down.  It’s called the “Law of Proportionate Response,” and it’s gonna kick the living crap out of you.   Plus, you’ll be too tired the next day to run your company after fighting crime all night, so you’ll most likely lose that too, thanks to a board of directors trying to usurp your money, power and influence.  Just do yourself a favor and forget the superhero thing.  Just donate the money to your city’s police department instead.  You’ll probably make a lot more of a difference that way.

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