Side Hustles, Bonuses, and Credit Card Hacking

I know I have talked about this before, but last week Birchie did a round up of her bank bonus and credit card hacking side gigs, and it sparked a fire in me. If you know me, you will know that I already had all of this info handy; I just had to put it in a cohesive post. So let's get started. If this stuff makes your eyes glaze over, skip to the end, where I give you two suggestions for beginners and/or the non-financial people of the group! 

I started my credit card hacking journey in 2005. I signed up for the Chase United Visa and the Chase Marriott Visa and I got roughly 60,000 points for each of them as bonuses. Both cards had roughly a $100 fee. After that, I used only those two cards for the years I was traveling for work and through this, I sent my parents to Scotland on first class, sent myself to the Philippines, and supplemented my hotels for my 2008 South America and my 2010 Round The World trips. Bottom line is that from 2005 to 2023, these cards probably got me thousands if not tens of thousands of dollars worth of "free" flights and hotels. Of course, the best part about this, is that much of the money I put on those cards was for work expenses, so, thank you unnamed company that I used to work for! I think they have since gone to corporate cards, but at the time I was there, you could put everything on your own credit card. This also got me Premier status on United for years (no longer though!) and lifetime Titanium Elite with Marriott. 

I also just finally used up the rest of my United points on our flights to Germany, so now I have basically none left. Because of this, and the $95 fee, I downgraded my United card to a zero fee card, mostly so I could keep the twenty year relationship stat, as that does help when you are applying to new credit cards (they look for your longest relationship). 

I am not telling you all this to brag; my point is that sometimes credit card hacking is an excellent way to get "free" money. The best way is to get the sign up bonus and use that for free travel. Like Birchie said, if you don't travel, this may not be that exciting, and you should also make sure that you can pay off the credit card(s) every month or it is not worth the interest you have to pay on it. 

But let's get to the fun stuff. Over the last 14 months, I have received some bonuses, not just from credit card hacking, but also from moving money into a brokerage account. This worked out great for me, as I had to move my accounts after I quit my job, so at that point I searched to find out which firms had the best bonus, and I moved my funds to them. I actually ended up going with more than one, as that was the best bang for my buck. Is this a little hard to keep track of? Not for me, especially with the apps that we have now, where you can just pop in and look at them whenever you want. Also, before this year, I opened two different high yield savings account for the same reason, but I will not get into that in this post. 

What odd "side hustles" did I have last year? 

#1. Selling crap stuff on the internet! Like I mentioned in this post, I sold a lot of stuff on the internet in 2024 and did make some money but I am not sure that the time involved is really worth it! I would estimate that I got about $3,500 but the hours involved were plentiful and this is of course on things that I probably spent five times that much on. That is a complete ballpark, and maybe if you depreciated everything it would not be that much, but my point is that obviously something is better than nothing, but I did not "make money" from this gig! Net income = negative! I also sold my car, which I paid about $10,000 for in 2016, for $4,000 after using it for 8 years. So, it cost me about $750 per year to "rent" it (or $2.08 per day, not under the $1 per use rule!). 

Selling camera gear. Sob. 

#2. Brokerage Bonuses. I will not get into actual dollars here, but currently Merrill Lynch, Charles Schwab, JP Morgan and E-Trade all have bonuses if you transfer a certain amount of money to them and keep it there for a certain amount of time. You can usually find updated information on this at the Bankrate website. Like Birchie said, you can also find bonuses for checking accounts, but I did not go down that road. 

#3. Credit Card Hacking. Although the cost of the cards I opened is around $700/year, the bonuses that I got ended up netting me about 500,000 points, which if you value them at $0.01 per point just to make it easy (it can range from $0.005 to $0.025, but generally if you get "cash back" for them, it is at around $0.01), would be about $5,000 worth of points. Now, obviously if I let them sit and do nothing, at some point in the future, my cost per year will catch up to my bonus amount. However, I do not plan on doing that! 

In the last year, aside from the United flight, I have also booked three hotels using points and the value for the rooms was around $1,000 in total. I also booked my flight from Canada back home using a credit and so that flight also saved me about $250. So basically, I have already utilized enough points to make the $700/year fees worth it for this year. 

However, let's get to the dark side. As Birchie mentioned, the talking heads on YouTube often talk about "all the perks" and how "you basically are getting this card for free," etc. Also the credit cards themselves will say the same thing. However, you really do need to look at the fine print and see if they do actually make sense for you, based on where the best point value is, and whether or not you will use the credits etc. 

Dark Side #1. The portal. Sometimes the card will give you more points if you use the portal to book something, or they say that you get it cheaper, or you may be able to use your points to book in the portal, but this is not always a better deal. Sometimes the deal is much better on Booking or on the hotel website for example. Also, you can use points to pay off your credit card at $0.01 per point, which is not maxing out the value. You could possibly transfer points to a hotel or air partner and get a value of $0.015 - $0.025 cents of value per point instead. 

Dark Side #2. The "credits." Many times the card will give you credits for dining or travel but there are usually caveats. For example, the AMEX Gold says that they will give you $100 in Resy, $120 in UberEats, $120 in GrubHub and $87 in Dunkin Donuts credits each year. If you add that up, you would get $427 in credits for a card that cost $325. Nothing wrong with that, right? Well, they issue the credits only if you use the service and usually only on a monthly basis. For example, UberEats is a $10 monthly credit, only credited if you spend more than $10 in that particular month at UberEats. The Resy credits are only once per half year. So you can't just go and spend $120 at UberEats in one go and get credited. For me, the credits are worth maybe $100 if that, as I don't really use these platforms. 

Dark Side #3. Other perks. Many of these cards come with additional perks. It may be TSA Pre, travel insurance, car insurance, extended warranties on purchases or even free returns on some products. They also may have lounge access or food credits in airports. Some of these items are worth it to me and some are questionable. For example, lounge access. I have a card with this and last year I barely flew, so did not really get to use it. However I did fly, once from Canada to Portland and back, once from Halifax to Vancouver, and once from San Francisco to Frankfurt. In all of these cases, the terminal I was in did not have a lounge. So basically for now, I am 0 for 3 as far as getting any value out of my "free lounge access." However, I did rent a car for two days, and the insurance would have cost me about $60, but it was covered by my card. So that one is worth it to me. <---- by the way, remind me to tell you about the time I got scammed by the rental car company and my AMEX saved me! 

The verdict? I guess I will give the classic answer on this, and the verdict is that doing any of these things depends on your situation, so some of them may be worth it and some, not so much. If you have all the time in the world, putting something on FBMP and letting it sit until someone wants it may makes sense. If you are trying to offload a lot of stuff in a short time, it may be better to put it on the curb. Brokerage bonuses do require possible account or cash transfers, and more paperwork at the end of the year. Credit cards can offer good perks if you use them right! I guess the bottom line is that I will probably quit my selling stuff online side job and stick to the credit card hacking. 

I also plan to do a review of my cards at the end of this year and see which ones were actually worth it and which were not, and will then cancel one or two of them depending on what I find out. 

Where can you find out more? You can see what cards I currently have on my Tips and Hacks page. Other resources: The Points Guy, NerdWallet, or Bankrate. Happy hacking! 

If you want two suggestions here they are: If you rent your house, you can pay with the Bilt credit card, which has no fee, no bonus, but gives you 1 point per dollar spent on rent and 2-4x points on other things. To put this in context, if you pay $2,000 a month, you will get at least 24,000 points, which can be transferred to American for basically a round trip flight, or to Hyatt for about 2 nights in a hotel. I don't have this card, but here is an article on Nerdwallet about it. 

The second one is the Chase Sapphire Preferred, which does cost $95, but if you spend $4,000 in the first three months, it has a bonus of 60,000 as of this writing, which is valued at about $750 (put in context, a US RT flight can be found for about 25,000 points, so you would get about two of these), and it also gives 3x points on dining and 2x points on travel. You get free DoorDash too, which is worth nothing to me, but may be worth something to you! I don't have this card, but I have other cards that use the Chase Travel Portal and am happy with them so far. 

What is your favorite life hack? Do you have any side hustles? Do you know if any of your credit card have any perks?