Some Crazy Things I Did to Make Extra Money in College

As someone who grew up financially comfortable but not wealthy, studying and earning money was always on my mind.

We were a frugal family because everything we saved went towards flights back to Taiwan to see the rest of the family. We always had food on the table and as a kid, I never worried about money. I was only supposed to worry about school.

This also taught me responsibility. When my parents gave me money, I couldn’t waste it. That money came with baggage (that I put on it!).

When I got to college, I kept the money my parents gave me separate from what I could earn on my own. Money from parents was money for needs. The money I earned was baggage free. It was extra so I could spend it however I wanted.

I found a lot of different ways to make money in college and today I wanted to share them in a fun post. I won’t list the boring ones, like summer internships, being a teaching assistant (really, a glorified grader), work-study, or taking psychology surveys or focus groups. Booooooring (but those psych surveys paid well!).

Until college is free, you need those boring jobs… but that doesn’t mean I need to bore you with them.

Just some of the fun ones that I fondly look back on. πŸ™‚


Table of Contents
  1. AllAdvantage!
  2. Chasing Casino Bonuses
  3. Flipping “Stuff” on eBay
  4. I Sold Software!
  5. “Hot Deals”
  6. A Note of Caution


If you were on the internet in 1999, and had more time than money, you knew about AllAdvantage. In 1999, I was in college and had a fast internet connection (and a quiet one!) for the very first time, so obviously I squandered it by using a pay-to-surf toolbar. (more on fast internet connections later)

AllAdvantage was a toolbar that you installed and it paid you to surf the web. It didn’t pay much but the dot com bubble was bubbling and money was flowing, so everyone I knew was cashing in by installing this toolbar. We even installed software that moved your mouse so the toolbar kept paying even when we weren’t there.

But alas, the dot com bubble burst and the gravy train of free money was no more.

Chasing Casino Bonuses

I’d written about this before in my post on my craziest side hustle but, in short, I gambled online.

Years ago, online casinos competed aggressively. They would offer hundreds of dollars in bonuses if you were willing to deposit the same amount. To cash out, you just had to put a multiple of that into play (bets) before you could cash out your money and the bonus. In college, I was depositing in $100, getting $100, and then playing blackjack to reach the bonus requirements.

When it started, casinos weren’t too savvy. They only required you to put 4x into play. If I deposited $100, I got an extra $100 in bonus, and I had to put $800 in bets. So I played 160 five dollars hands of blackjack. It was a little hustle that earned me a few bucks each time I did it and it was fun.

Eventually, casinos wised up and increased the betting requirements. I stopped when it reached 16x because that’s when it was about breakeven.

More on that experience in the previous post if you want juicier details. πŸ™‚

Flipping “Stuff” on eBay

Before it was cool to buy stuff on the clearance rack at your local store and listing it on eBay or Amazon, I was flipping “hot deals” I found on Fatwallet (RIP!) on eBay. I’d charge it to my college credit card, list it, and try to sell it before the bill was due.

In many cases, it was clearance product or a great promotion or some coupon stacking regular folks weren’t aware of. There was a lot of software where I bought it, claimed the rebate, and sold the software minus UPC (all clearly labeled – some people don’t want to deal with rebates).

There were a few items that stood out from my time doing this:

  • John Deere Trucker Hats – This was probably one of the longest-running deals. Remember when Ashton Kutcher’s show PUNK’d? He used to do those cut-ins wearing John Deere trucker hats? Well, people were snapping them up on eBay for like $20-30 plus shipping. I would just call John Deere stores in the area (and beyond) and buy them from the stores for like $10-15 a pop. From this period, Von Dutch hats were more valuable but I couldn’t find a cheap source for them.
  • Washington Wizards Michael Jordan Jerseys – HSN or QVC had them on clearance and I used to buy 10 at a time and slowly list them on eBay to avoid flooding the market. I still have one in my closet!
  • Band of Brother’s DVD Boxed Set – This is my wife’s favorite story because I bought them on sale from (same region as the US!) and it took forever for them to arrive. I listed the boxed sets before I received them and people were getting upset because I hadn’t shipped it yet. When they arrived, we immediately packed up ten of these boxed sets and ran to the post office.
  • Adult Anime Movies/TV Series DVD? – I vaguely remember this because I can’t read Japanese but I found some online DVD shop that was selling this movie or TV series for super cheap, like $15, and I could sell them on eBay for $40-50. I remember one person emailed me after the sale to ask that I ship it wrapped in a paper bag to his office!
  • Transformers TV Series – This was back before high-speed internet was in every home (and before there was a Transformers boxed set, because you know I’d have gotten a cease and desist order in a minute). I got all the episodes of the TV show, burned them onto 7 CDRs, and sold them for $20. I still have the sleeves, a huge stack of CDRs, and a CD labeler in a closet somewhere. I could’ve made even more with MacGyver but I could never got all the episodes – I was short like 8. You could’ve sold those for like $50 on eBay…

I Sold Software!

When I wanted to flip something on eBay, I had to research average selling prices, unsold inventory, etc. It had to be profitable, I didn’t have much capital to work with. Today, I bet there are a million tools you can use. Back then, not so much.

So I wrote an ugly Java program to scrape eBay’s pages to help make my life easier. It got a little trickier when they forced you to login before they’d show you completed listings. πŸ™

Turns out, a friend of mine, Brett, was doing some economics research and needed an eBay scraper. With some minor modifications (mostly to output to a text file rather than display results on a screen), I sold it to him for a few hundred bucks.

I was especially proud of this particular one because I was (am?) a computer science major. This is what I was supposed to do!

“Hot Deals”

Fatwallet no longer exists but it was probably one of the more popular forums on the Internet. I used to go there all the time to look for products I could re-sell on eBay. Techbargains, Slickdeals, etc. – they’re all giants in that space then and they remain pretty popular even today.

I started my first website, Bargaineering, because I thought I could compete with those sites. The name was a portmanteau of bargains and engineering. I was “engineering bargains.” (so clever!)

This hustle wasn’t in college, I’d already graduated by the time I registered the domain. But you can probably see when the seeds were planted for this venture. πŸ™‚

I’d learned about affiliate marketing, where you can earn commissions off sales, and was going to follow that same model and make a little extra cash. I was working full time so I wasn’t thinking this was going to be a big thing. I thought it would be a nice way to earn some extra cash.

Much like how my college hustle money was for fun, I saw the website earnings as fun money and my job as serious money.

About a year into writing about hot deals, and not really have too much success, I started the blog section as a journal of my own finances. Like with many accidental pivots, the blog is what took off and the deals part of the site was eventually shuttered.

A Note of Caution

I wanted to share these side hustles because they were fun. I think they give you an idea of the things I did before blogging and entrepreneurship.

Objectively, I believe these are all (except the blogging one at the end) terrible side hustles. I don’t think any of these are worth pursuing long term because there’s no way to scale, there’s no competitive advantage, and there’s no way to pull yourself out of the process. They have none of the hallmarks of a great side hustle.

What side hustles did you do in college?

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About Jim Wang

Jim Wang is a forty-something father of four who is a frequent contributor to Forbes and Vanguard's Blog. He has also been fortunate to have appeared in the New York Times, Baltimore Sun, Entrepreneur, and Marketplace Money.

Jim has a B.S. in Computer Science and Economics from Carnegie Mellon University, an M.S. in Information Technology - Software Engineering from Carnegie Mellon University, as well as a Masters in Business Administration from Johns Hopkins University. His approach to personal finance is that of an engineer, breaking down complex subjects into bite-sized easily understood concepts that you can use in your daily life.

One of his favorite tools (here's my treasure chest of tools, everything I use) is Empower Personal Dashboard, which enables him to manage his finances in just 15-minutes each month. They also offer financial planning, such as a Retirement Planning Tool that can tell you if you're on track to retire when you want. It's free.

>> Read more articles by Jim

Opinions expressed here are the author's alone, not those of any bank or financial institution. This content has not been reviewed, approved or otherwise endorsed by any of these entities.

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John Pham
4 years ago

Jim, so ODD… I literally drafted a post for my site over a month ago and just published it recently. I found you through Google and our content literally crosses each other ::face explodes::

What was your Fatwallet name? I was very active on Hot Deals and Finance under “Azurik”.


John Pham
4 years ago
Reply to  Jim Wang

I love the little internet niches, they really do exist πŸ™‚

SIS was great. In general, that time frame was great – it was the golden age of message boards. I still get a little nostalgic when Tim Storm (founder of FW) pops up here and there in my feeds.

Nice to see a former member have a blog like this – congratulations. My site is very new (3 weeks), but had sold a well-known blog a few years back – switching from lifestyle to finance where the heart is.


4 years ago

Great post on side hustles and I completely agree that most of those are not great long term options lol. I recently wrote a blog about how much of a positive effect side hustles can have on someone’s financial health. From paying down debt to creating emergency savings they can really put people on the path to financial freedom.

Kim @ The Frugal Engineers
4 years ago

Medical studies at the Stanford Medical School were how I bought plane tickets home for the holidays. They paid very well for flexible short-term gigs!

4 years ago

I donated (sold) bone marrow for $50 a pop a total of six times.

Also let some doctors put an arterial line in one wrist while testing a non-invasive device on the other wrist. I was monitored for about an hour and made $250 on that one.

I was basically a hybrid human guinea pig / voodoo doll for money. It did give me a chance to meet some medical researchers at the school where I ended up attending medical school.


4 years ago

Didn’t do this myself, did plasma in grad school.
Why A Central Square Stool Bank Is Paying $40 Per Poop Donation
A new storefront is opening steps from Cambridge City Hall. But instead of trying to sell you something, its mission is to buy something you produce: your poop.

OpenBiome is the world’s largest stool bank. It’s just like a blood bank but for fecal matter.

β€œAs demand has gone up for poop, we need more donors,” says Majdi Osman, an infectious disease doctor and the clinical program director at OpenBiome.

4 years ago

I used to have a lot of the same side hustles back in the day. I remember using All Advantage – and some other toolbars back in the day, but I don’t remember gaming the system like that. I was a big FatWallet junkie, I even still have a t-shirt from the site. I used to do the same thing in tracking down the hot deals, buying as many as i could and then reselling them to people that didn’t take the time to research the deals. I did OK with that but it was a hard side hustle to… Read more »

Jaime Latimer
3 years ago

Selling things off Ebay really does save me sometimes. The main thing is to know the limit and not to sell things you need.

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