Your craziest side hustle? Mine was that time in college I gambled online…

My wife and I met while we were in college together in Pittsburgh. When we started dating, a few of my friends mentioned to her that I would “gamble online a lot but that it was OK, because I was good at it.”

And I was good at it… but I wasn't good at gambling, I was good at taking advantage of promotions. (the key to making money fast!)

(and I can thank my college friends Jason W. and Matt B. for introducing me to it in the first place!)

I was an online casino promotion hunter.

Back then, as is the case even today, you could get a deposit bonus every time you joined a casino. Deposit a dollar amount and you would get a percentage (100-500%) as a bonus. You could cash out once you wagered both your deposit and the bonus a certain number of times.

In the beginning, the multiple was 4 times. Deposit $100, get $100, put $800 into play (4 x $200) and you could withdraw your cash.

That multiple would creep up over time. 8x, then 12x, then 16x. It was at 16x when I stopped.

To hit the wagering multiple, I would play Blackjack (optimal strategy, courtesy of the awesomely-named Wizard of Odds) until I hit the limit, then cashed out. I never felt the pull to keep playing because there were a ton of casinos. We used to keep spreadsheets, that's how many casinos there were.

(Looking back, I kind of wish I had known Colin of Blackjack Apprentice, he could've taught me a few things!)

Nowadays, this is much much harder and with far lower yields. I just peeked at some random casino (Lucky Red Casino) and they offer a 400% up to $4000 bonus but you had to wager it THIRTY times. Oh and only wagers on slots, keno and scratch cards counted. That's bananas, those are terrible games (both odds-wise and entertainment-wise!).

How much did I make? I don't recall how much I made over the course of about a year but it was in thousands. Some casinos I walked away with a few hundred, some I walked away with nothing, and a few rare cases I cashed out with over a thousand dollars.

I've lost and won $1,000+ blackjack hands. That taught me how casino chips, especially internet casino chips, don't feel like money anymore. A thousand dollars to anyone is a lot of money. And I was an idiot who wagered it twice!

Incidentally, both were equally horrifying.

You know how poker players, who have spent countless hours playing, have seen every hand lose? It's like that in anything, including blackjack. Having a 20 and getting beat by a dealer getting 21. The sense of dread and inevitability you get when you have a 14 and the dealer is showing a face card. Oh and when the dealer flips over a 2 and a 3 and slowly walks his way to a 20 to beat your 19.

Why did I stop? I was running out of casinos where cashing out was easy (biggest reason) and the multiple was getting too high. It was taking too long to finish off a casino and honestly it was getting boring. The payout and payout frequency was getting lower because of the wagering multiple, which is the point, and the novelty of gambling online had worn off.

Did I learn anything? A few things actually.

First, there's always an opportunity to take advantage of a promotion, especially in a market where a lot of the other participants aren't taking advantage of it. Most of the people who signed up to those promotions wanted to gamble. Those people were subsidizing me and my friends going out and promotion hunting. We had more time than money so we could hop from place to place and “work” for our cash.

Next, I recognized how my body responds to stress. It's funny because sometimes I don't consciously recognize it's a stressful situation but my body does and I can recognize that, which is useful.

Lastly, I learned I don't really enjoy gambling that much. I play poker with friends but I'd never go to a card room full of strangers. I'll sit down at a table with friends, but I rarely do it by myself. I think it's because the odds are never in your favor. So unless I'm being entertained otherwise, I would rather buy my own beer and do something else.

That said, promotion hunting was a fun time because I had a positive expected value whenever I signed up to a casino. 🙂 Of all my college side hustles, that one was probably the most interesting and “craziest.”

What's your craziest side hustle?

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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 Personal Capital, 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.

He is also diversifying his investment portfolio by adding a little bit of real estate. But not rental homes, because he doesn't want a second job, it's diversified small investments in a few commercial properties and farms in Illinois, Louisiana, and California through AcreTrader.

Recently, he's invested in a few pieces of art on Masterworks too.

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  1. Wayne says

    Brings back good memories. I even got a few family members and friends in it. As the blackjack bonuses were getting harder to come by a friend of mine in the gambling forums introduced me to “sports arbitrage” and combine that with bonuses was a bit more lucrative. I think I enjoyed manipulating the numbers more than the gambling. The wife and kids didn’t mind me spoiling them ever once in a while though.

    I had fun!

    • Jim Wang says

      It was a fun time, it started getting unprofitable when it was like 20x the bonus and deposit… I suppose 20x didn’t matter if you were in it for the thrill, I was in it to make money! I still have my Xbox (albeit sitting in my basement in a box) that I paid with the spoils.

  2. Tim says

    Good story. Those were the good old days. I used to be obsessed with online poker, and played a ton (hours a night) from about 2004 – 2011. The games were so good back then, particularly from about 2004 – 2008, that it was almost like stealing. Sadly most of the players who watched poker on TV, went bust, and the games got harder. I made a small amount, but wasn’t that good myself. I still kick myself for missing out on that era. What’s even worse is I just put my winnings in the bank. If I had instead used the money to buy shares of Apple and Amazon when they were dirt cheap, I’d be a multi-millionaire right now. 20/20 hindsight can be a curse LOL.

    • Jim Wang says

      Yes! I played a lot of online poker too – I really enjoyed those little $11 SnG tourneys. I never graduated beyond 2/4NL games while in college though, it was even before you… probably 1999-2001. Fun times!

  3. Florie Barry says

    Aloha Jim, I remember those Las Vegas casino days. Getting good deals is rewarding since I am frugal. I would walk around the casino for exercise and not buy anything or spend money. Back in the days when slot machines paid with coins, my husband gave me a bucket of coins he won. When we met up about a half-hour later, he said, “You spent all those coins already?” I said, “Yup, I cashed it in. I bought coffee and snacks. That’s my side hustle, getting free money for coffee and chocolates.

    • Jim Wang says

      I used to love signing up for new loyalty programs and getting some kind of bonus… so much fun.

  4. Tim says

    My side hustle isn’t crazy, but I make about $300 – 400 a month just by donating plasma. They always have bonuses that they text you with, and if you make sure and hit all the bonuses it is really easy money. About 10 years ago I used to make side money playing online poker, but it was a lot more stressful and if you calculated out all the hours I played, I was only making like $1 an hour playing poker, or even less. Donating plasma is a lot easier. I just read a book or watch whatever movie they have on.

    • Jim Wang says

      Donating plasma is something a lot of folks do for extra cash (and yes, not that crazy) but it’s still great.

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