Our Writers Discuss Embarrassing Financial Sins, As Warnings To Us All


We all do stupid things financially when we’re young…or (still do) now. I buy scratch off tickets on the reg, even though I never win. I mean really, never. I don’t even win the (statistically easy) free tickets. And yet, I have this compulsion. I mean this could be the day I make it big, I think. I’ll scratch away, and win A THOUSAND DOLLARS. (Yeah that sounds like heaps of money to me at the moment…).

And yet, if I just never bought another scratch off ticket, I could save a thousand dollars. Easily.

When we talked about these financial sins around the Uproxx virtual water cooler, we realized that all of us have done some really dumb things. I mean how many of us just have hundreds of Beanie Babies sitting in boxes in our parents’ basement right now? Or how many of us thought of our DVD and CD collections as an investment that would last forever? And how many of us had our first jobs at Banana Republic and spent our entire paychecks buying business casual clothes at 16 years old? (Oh… that one might just be me.)

So we’re sharing our most embarrassing financial decisions for your entertainment. All the silly, ridiculous things we thought were such a good idea at the time. Because we’ve all been there. So laugh at us, and then share your own finacial nightmares in the comment section so we can laugh with you.


Martin Rickman, Deputy Editor, Sports — When they first announced that they were going to stop selling original formula Four Loko, I flipped out at the opportunity to stock up. I was an avid drinker – and very stupid early-20-something – and figured, “well now’s my chance to make a bunch of money on eBay or elsewhere online.” I went down a main drag in one of the Eastside Cleveland suburbs to each and every convenience store and gas station buying up cases at a time, ending up with well over 100 of the 24 oz death machines. Then I never got around to actually selling them, instead stashing them in my closet and drinking them before I went out (to disastrous results). Sure I was only out about $150 total, but my body took a hit I’ll never really recover from.

The last two I gave away to a friend’s brother who helped me move. So maybe I made a profit off them after all.

Dan Seitz, Staff Writer — When I was in my early 20s, I got a credit card with a $1000 limit. I managed to max out that credit card entirely because I could not stop buying DVDs. Doing the math I think each DVD cost me roughly twice what I actually paid for it.

Christian Long, Writer — I was working at my old job when Dr Pepper announced they’d be shuttering production of Dublin Dr Pepper, which was like regular Dr Pepper, but was bottled at a plant in Dublin, Texas, where they used cane sugar instead of corn syrup back before it was cool. Hearing the news, I immediately got up and ran to the two closest gas stations and bought out the supply Dublin Dr Pepper in both.

Unfortunately, neither had a lot in stock, so I only managed to score three bottles between the two stores. I later ended up forgetting them in a desk drawer, and recently called an old co-worker to see if he could grab them for me. I’ve yet to hear back. At the time I lost out on a little under $5 (plus tax), but right now they go for up to $10 a bottle on eBay, which has (so far) cost me a 525% profit increase. Get it? I’m playing the financial long game here.

Bill Hanstock, Senior Editor, Sports — I went to graduate school, but nobody told me about the difference between an MA and an MFA, so I’m massively in debt without a terminal degree.

Alia Stearns, Writer — My first car wasn’t terribly expensive, but the price was far too large for the two weeks I actually got to drive it. Big Minty was, unsurprisingly, the color of Wrigley’s spearmint gum and was a Buick of epic 70s proportions. The back seat rivaled most love seats in size and seating capacity and the dash was the size of a coffee table. It was a car only a mother could love. My mother. Assuming my parents must know more about car buying than I did, I asked my mom for help, and she advocated for this car like she lived in Portland, OR and it was a Subaru.

Cut to a few weeks after purchase when the car wouldn’t start. It had a phantom drain, which is fancy car talk for “we don’t know where the problem is, but it is going to keep depleting your battery until you spend an exorbitant amount of money for us to investigate.” In the words of Hall and Oates: no can do.

I was left with a huge car that wouldn’t run, a considerable dent in my savings, and no idea how to get it the Hell out of my driveway.

Jason Tabrys, Features Editor — Our own Mark Shrayber is a ridiculous and amazing present giver. These come randomly and usually un-attached to an expectation that I respond in kind. Which is great because I am a very cheap person and only give gifts of my presence and council.

One time, however, Mark sent me a massive inflatable unicorn raft after I remarked about another co-worker’s Facebook post. That’s really all it takes. Anyway, I got it and then I felt like I was kinda pressured (in an unspoken way) into getting one for Dan Seitz and spent like $60 goddamn dollars on it (after some serious hunting for a bargain and a couple of failed low-ball bids on eBay) because I felt as though I had entered some weird cabal where I’d be cursed out and excluded if I didn’t pass along the unicorn raft love.

Also, Dan’s thank you was… tepid, you know? Like, let me feel your joy over this $60 raft, man! Invite me to a pool party and let me stand in the glow of everyone else complimenting the raft and then you pointing at me and telling everyone how amazing and thoughtful I am. Give me something for my money. Anyway, my raft is in the package behind my couch. Anyone wanna buy a unicorn raft so I can be made whole and cleansed of this financial regret? Makes a great gift.

John Gotty, Senior Hip Hop Editor — Somewhere along the line the early ’00s, I bought a sweater. It wasn’t just any sweater. It was a magnificent Iceberg History sweater in red. With Pluto or some other Disney dog and it had patent leather pieces around the eyes or something along those lines. And, it only set me back $700.

At the time, I was early in my teaching career so I wasn’t making much money there, but I always had little hustles to make side income so I’m sure that’s where I got the money to purchase what turned out to be a fashion faux pas of the greatest levels. At the time, Iceberg was a lava-hot brand, certified cool by Jay Z, and their clothing always used famous cartoon characters from Disney and Peanuts. When you wore it to the club, the bar or any social event, people knew you were cool as hell because it wasn’t cheap and it was particularly hard to find certain pieces.

This sweater wasn’t the only piece I had either. My poor ass had a closet stuffed with at least a couple grand of Iceberg gear, making me the hustler’s poster child for coolness. Until Jay Z and other rappers hopped on to some other trend. As quickly as Iceberg came, it went and left me with a lot of expensive shit that looked real goofy. Granted, I still made a lot more expensive clothing purchases before finally breaking the habit.

After I got over the phase, I stopped buying almost any pricey clothing and the items I did buy had to serve at least more one that one purpose. Today, I mostly wear grey t-shirts and black hoodies, opting to go for the daily uniform look espoused by Steve Jobs. What I won’t do is buy any hot “fashion” items. Every time I even consider it, images of patent leather-eyed Pluto flash in front of my mind to remind me not to repeat my mistakes.

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Delenda Joseph, Writer — I came into $7,000 when I turned 18 and spent it all in a matter of three months on electronics, Jordan’s, clothes, music, toys, and feeding my basic bitch Bath and Bodyworks addiction. Those Warm Vanilla Sugar body scrubs were so luxe! My first purchases were gold jewelry and a Sidekick. I had no credit and was put on a 300 minute a month plan or something. An 18-year-old with a 300 minute a month plan? Disaster. I was constantly over my minutes and paying overages out the ass. Not to mention buying stupid ringtones that added up after a while. The only remnants of my splurging that still exist today are my CDs and Jordan sneakers too small for my feet.

Steve Bramucci, Life Editor — I feel like I’m just habitually catastrophic when it comes to money. Grad school on loans, not canceling memberships, buying meals for people who neither expected nor needed to be treated… I could make a long list. When I started at Uproxx I downloaded a program called Flixel to make Cinemagraphs. Have you heard of cinemagraphs? I doubt it. But I thought I was going to change the game with these dumb things. I was paying for the membership for six months before I canceled, and never even opened up the program once.

But the best example of my financial anti-prowess — besides the six figure MFA loan rapidly accruing interest as I write this — is connected to cars and unpaid parking tickets. I had so many tickets in college, that I had to work for parking services for free all through my final semester. The state of California isn’t so forgiving. Before finally getting my act together, I’d had no less than four cars towed due to an accumulation of tickets and left all four of the cars in the impound forever. I have literally just given the state four cars, which they sold at auction to pay off my fees. So. Freaking. Dumb.

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