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My 2019 Credit Card Signup Bonus Strategy

First post in a while as at least someone in my family has been sick for the last few weeks. My son vomited on me twice, including once pretty much right into my mouth. Alright, TMI and that’s not what you’re here for. Since it’s the first day of 2019, I figured I’d outline my personal strategy for the year when it comes to credit card bonuses.

Now my strategy almost certainly shouldn’t be your strategy as I am more limited in the cards I can get since I have had so many over the years. For example, American Express now only lets you receive a signup bonus once per lifetime per card. There are still several Amex cards I have never received a bonus for, but none of them have a signup bonus that’s worthy of using a credit inquiry on at the moment.

Chase’s 5/24 rule, meaning you can’t be approved for any Chase card if you have gotten 5 or more credit cards from any bank in the past two years, is a big factor in what cards I will be applying for. Up until a few years ago, I could apply for 12 cards a year and not have to worry about being limited by Chase. Now I have to be more careful. Over the past two years I have applied and been approved for 7 credit cards. But 3 of those cards have been business cards and those do not count toward the 5/24 rule.

So basically I want to hit as many business cards as I can this year, thus “aging” my personal cards so come next year, I should be at 2/24 and able to apply for two new Chase cards. The beauty of Chase cards, at least for most of them, is that you can receive a bonus for the same card every two years. The one exception that I know of that was recently added is on the Chase Sapphire, which has a four year waiting period to get a second bonus.

My last credit card application was for the Southwest Premier Business card, which gives you 60,000 Southwest points after $3K in spending. I will complete the minimum spending later this month and then I am considering applying for the personal version of the Southwest Premier card. That would put me right at 5/24, but after hitting the minimum spending, I will have earned 120,000 SW points, which is enough to obtain a Companion Pass. That pass, which allows a family member or friend to fly free with you an unlimited amount of times on Southwest through the next calendar year after you earned the pass, can be worth thousands if you fly a lot.

I also have my eyes on the Citi AA business card. It’s currently offering 70,000 AA miles (those can easily be worth more than $1,500 in travel if used wisely) if you spend $4K in four months. The $99 annual fee is waived for the first year.

A reminder that many things count as businesses when it comes to applying for business credit cards.

That’s basically my plan for the first half of the year. During the second half, I will keep my eyes out for any huge bonuses and then I will have to decide if they are worth going after even if they are going to add to my 5/24 total and possibly delay my next Chase application.

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How to Book American Airlines Award Tickets With Chase And Amex Points

There are numerous American Airlines branded credit cards and I’ve had several of them in my credit card points game career, but in most cases, the best cards are ones that earn transferable points, i.e. they are flexible.

If you have Chase Ultimate Rewards points (earned through a “premium” card like the Sapphire or Ink) or American Express Membership Rewards points, you can transfer them to numerous hotel and airline programs. So then when you are planning a vacation, you can search for reward nights and flights across a variety of brands and find the best bang for your points. But American Airlines is not a transfer partner of either Chase or Amex. But don’t despair!

British Airways is a transfer partner and since American Airlines and British Airways are both part of the oneworld alliance, you can book American flights through British Airways after transferring your Chase or Amex points to BA at a 1:1 ratio (sometimes even as good as 1:1.5 when Amex runs bonus offers). The great thing about using British Airways Avios (their reward currency) toward American flights is you can often score some sweet deals, especially on short haul nonstop flights.

Any flight* of less than 1,150 miles can be had for 7,500 Avios. So you can fly from New York to Miami for what is essentially $75 worth of points when looking at the cash value of redeeming points for straight cash back or a statement credit. To book the same flight with American Airlines points would cost 12,500 miles.

Another huge benefit of booking AA flights with Avios: there is no close-in booking fee. Book an American flight with AA miles within 21 days of departure and you need to pony up a $75 fee. And that just ain’t cool. You can book the same flight with Avios, even just a few hours before takeoff and there’s no fee.

* Any flight that has seats available at the MileSAAver level when you search for reward flights on the American Airlines website.If you see they are available at the Super Saver level, then they should be available to book on the BA website. Frankly the BA website is awful and glitchy so I highly recommend searching for flights on AA first.

My wife and I flew business class on American to Cancun for our honeymoon in 2012 by redeeming 20,000 Avios + $20-30 in taxes. No way we would have paid $400 in cash for that one-way flight, but that’s the beauty of this game: you can live large in business class with those hot towels, a nice three-course meal and all the alcohol you can drink included and you barely spent a dime out of your own pocket.


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Disney With Points: 2 Credit Card Bonuses Cover Flights/Hotel For Family of 4

Disney World is expensive. But the pain of paying more than $100 a ticket to get into a theme park can be eased a bit if your airfare and hotel are free of charge. And it’s really quite easy to pull off with just two credit card signup bonuses.

Now this will be easiest for people who live near an airport served by Southwest. It’s also not going to be much help for those who insist on staying at Disney World owned resorts. You can’t use points for those. Now my wife will argue that the perks that come with staying on a Disney property are worth the cost. But I will argue that free is free so the Hyatt Place it is. (But seriously, Hyatt Places are great. Free breakfast and not just shitty cereals!)

Any way, here’s how to pull this off:

  1. Apply for the Chase Southwest Business Premier card here. Just like the Chase Ink I wrote about in an earlier post, it’s obviously a business card, but many things count as a business. The bonus here is 60,000 Southwest points after spending $3K in three months. You do need to pay the $99 annual fee upfront. As long as your dates are flexible (i.e. you don’t insist on leaving on the Saturday at the start of winter break), those points are likely enough to get a family of four roundtrip airfare to Disney. As an example, I can book 4 roundtrip tickets from Islip MacArthur to Orlando leaving on Feb. 26, 2019 and returning on March 5, 2019 for 48,000 points plus $44 in taxes. If I paid cash for those tickets, it would come to $775.
  2. Apply for the Chase Hyatt card here. This one gets you 40,000 Hyatt points after spending $3K in the first three months and then another 20,000 points after you spend a total of $6K within the first 6 months. Same deal with the annual fee here. It’s $95 and it will appear on your first statement. Those 60,000 points can get you 7 free nights in this lovely Hyatt Place near Universal Studios. To pay cash for 7 nights at that hotel comes to $1,158.

So basically pay a couple hundred in annual fees and $44 in taxes and get nearly $2,000 worth of travel value from just two credit cards! And that’s why I love the points game. Now once you get to Disney, all bets are off and you spend all of your money on autograph book pens that your 4-year-old daughter will keep breaking.

I will eventually devote an entire post on Chase’s 5/24 rule, which basically means you can’t be approved for a Chase card if you have opened more than 4 credit cards from any bank in the last two years, but for now, make sure to check out this post on the Points Guy if you do plan on applying for several cards in the near future.

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Barclay Arrival Plus Review: New 70,000-Mile Bonus Worth $700 in Travel

The Barclay Arrival Plus recently upped its signup bonus to 70,000 miles if you spend $5,000 in three months. Now right off the bat, this card is worth getting at least for a year. Those 70,000 miles are worth $700 in statement credits toward travel purchases. The annual fee of $89 is waived for the first year.

But let’s look a deeper. Is this a card worth keeping for the long haul?


  • You get 2x miles on every purchase. You also get 5% of your miles back whenever you redeem miles toward a travel purchase so it’s basically a 2.1% cash back card. That’s pretty damn good.
  • You can use your miles toward any travel purchase. You don’t need to transfer them to airline or hotel programs to try to get the best value for your points. These miles are cut and dry. Say you book a $700 flight on Expedia. Once that purchase hits your Arrival card, you can go in and redeem 70,000 points to wipe out the $700. You will then get 3,500 miles back in your account as the redemption bonus.


  • You can only redeem miles toward purchases of $100 or more. So if you book at hotel that’s $95 a night, sorry you are out of luck. This limitation is annoying to say the least. The Capital One Venture, for example, lets you redeem miles for any travel purchase regardless of the amount.
  • $89 annual fee
  • The Barclay website is awful

Verdict: Cancel it after a year and stick with the Venture or the Fidelity Visa, both of which offer 2 percent cash back as your everyday card. But certainly get that big 70,000 miles bonus and then cancel before the annual fee hits in year 2. Apply here for the Arrival. Note that Barclay is a bit credit sensitive, i.e. if you plan on applying for a bunch of cards over the next year, this is one you want to apply to first.

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A $300 Checking Account Bonus With Minimal Effort? Yes, Please

After my last post on checking account bonuses, I was ready to get back to credit cards, but hold the presses! There’s a new $300 checking account offer out there that you are going to want to apply for if you like money. The bank is Santander. Yes, they are legit. No, I had never heard of them before I applied for an account last year solely to get a bonus.

Here’s the how to:

  1. Open an eligible new checking account by 12/31/2018 with the promotion code: DIGBONUS300DMP (DO NOT FORGET TO ENTER THE CODE)
  2. Have direct deposits totaling $1,000 or more post within the first 90 days, starting the first business day after opening the account.
  3. Keep your account open for at least 90 days and open at the time of the bonus payment.
  4. Once you meet these conditions, your $300 bonus will be paid.

Apply for an account here. The offer is only available to residents of NH, MA, RI, CT, DE, NY, NJ, or PA.

A couple things to note: you can close the account once the bonus hits, but it will likely take the full 90 days for you to get it. There’s a $10 monthly fee, but man oh man is it easy to avoid. One transaction a month of any kind keeps it fee free. I just set up a $1 bill payment each month to one of my credit cards and then just waited for the bonus to hit. As I tell my 2-year-old when he’s scared of his shirt going over his head: easy peasy lemon squeezy.

Oh, another bonus, you can fund the checking account with up to $500 from a credit card. So if you have a CC that you need to hit a minimum spend requirement on it, this is a great way to knock out $500 of it.

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Yes, Bank Account Bonuses Are A Thing Too

I will admit I got a bit carried away with bank account bonuses last year. M&T Bank was offering a $200-$250 bonus for signing up for an account and making a couple direct deposits. But here’s the thing: you could just keep creating accounts under the same name and address and get the bonus over and over again. Sadly, M&T Bank cracked down on this and you can now only get the bonus once per year. It’s probably for the best though as at one point I had about 20 checking accounts open between my wife and I and it was getting a bit nuts trying to keep track of all of them.

Most bank account bonuses have similar requirements: you make XX number of direct deposits and then you wait XX number of days and you get the bonus. In many cases, if you close the account before 3-6 months, they will hit you with an early termination fee. But I’d say just by doing the 3-4 best offers, you can easily make $1,000 for not a whole lot of time/effort and that’s the point of the game.

One thing to keep in mind about bank account bonuses: unlike credit card bonuses, they are counted as interest income. So for each one you do, you will receive a 1099 form and will need to pay taxes on the bonus. Now it’s not that much. For a $300 bonus, you might pay $50 in taxes max so still a pretty sweet deal.

Here are three of the top bonuses out there right now:

  1. Chase- This one is pretty much the holy grail. Chase is a huge bank and many people already have a Chase account. If you don’t, open one now! The requirements for the $300 bonus are simple: Open a Total Checking account with a deposit of $25 or more. Have a direct deposit hit your account within 60 days. Wait 10 business days for the bonus to post.  You do need to keep the account open for 6 months or Chase will take back the bonus. There is a $12 monthly service fee that is waived if you either have $500 or more in direct deposits to the account each month or keep a $1,500 balance. Of course you could just do nothing and pay the $60 in service fees over 6 months (the first month is often waived automatically) and then cancel the account. You’d still pocket $240. Apply here.
  2. TD Bank- Another $300 offer. Open a TD Premier checking account and receive direct deposits of $2,500 or more within 60 days to get the bonus. That’s a decent chunk of change. If you can’t make that work, there is also a $150 bonus if you make direct deposits of $500 or more within 60 days. The bonus will post 30-90 days after you complete the direct deposits. Probably toward the lower end of that range. There’s a $25 monthly fee for the Premier account that is waived with a $2,500 minimum daily balance. The $15 monthly fee on the account with the $150 bonus is waived with just a $100 balance. There’s no early cancellation fee at TD so once you get the bonus, you are free to cancel right away. TD bonuses are available in the following states:CT, DC, DE, FL, MD, ME, MA, NC, NH, NJ, NY, PA, RI, SC, VT, & VA. Apply here.
  3. M&T Bank – Most people probably have never heard of M&T Bank. I sure hadn’t until I got a mortgage through them. But they sure have a great checking account signup bonus! $250 bonus for setting up a direct deposit of $500 or more within 90 days of opening. Make sure to use promo code TL when signing up. The best part about this bonus is it usually posts within a couple days after the direct deposit hits. Keep the account open for 6 months or pay a $50 fee. Avoid the $15 monthly service fee by having a $2,500 average balance or at least $1,500 per month in direct deposits. Apply here.
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Chase Ink Preferred Offers 80,000 Point Bonus

The Chase Ink Preferred offers one of the most valuable signup bonuses out there right now: 80,000 Ultimate Rewards points for $5,000 in spending in the first three months. There is a $95 annual fee that is not waived the first year, but who cares?! Those 80,000 points are worth $1,000 in travel if booked directly through Ultimate Rewards. They can easily be worth more than $1,500 toward travel if transferred strategically to airline and hotel programs.

The card also offers 3 UR points per dollar spend on travel, shipping purchases, advertising purchases made with search engines and social media sites and on internet, cable and cellphone services.

Now the caveat, and it’s a relatively big one: the Ink is a business credit card. You need a business for a business credit card. But here’s the thing: a ton of things count as “businesses” for the purposes of obtaining a business credit card. Do you sell items on Amazon or eBay? Do you do any consulting work? Are you an Airbnb host? Well, then you can apply!

Just be honest on the application. If you sell items on eBay and only made $200 last year, put that down in the income section. If your credit score is above a 700, it’s very likely you will be approved.

Now this part is important: when you apply, unless you do have a have a registered business, select sole proprietor where it asks what kind of business you own and then enter your social security number as your tax ID/EIN. Also important: just put your name down as the business. I’ve read some reports of people running into trouble when their business name doesn’t match their real name. So just keep it simple and just put your name down in both sections.

You will very likely not get approved instantly for this card. That’s fine. Just wait a couple weeks and the card will likely wind up in your mailbox. If you do get a rejection letter, don’t fret, often this can just be because Chase wants to speak with you to verify your identity. So if you do get rejected, call their business card reconsideration line at 800-453-9719.

The $5,000 spend in 3 months for the bonus can be tough to pull and I haven’t done a post yet on ways to “manufacture” spend so if anyone needs a few ideas, just shoot me an email at

Apply for the Chase Ink Preferred here.

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Shopping With Points on Amazon to Save a Ton

Using your credit card points for shopping is generally an awful idea. Using points for merchandise or toward a purchase is often going to get you less than a penny per point worth of value and that’s not how we do things around here.

But if you have any Amex Membership Rewards points or Chase Ultimate Rewards points, Amazon has two highly lucrative offers that you are going to want to take advantage of. Now it seems these offers may be targeted, but you should at least check to see if they are available on your account.

The Amex offer is the better/bigger one. If you redeem just one MR point toward your Amazon purchase, you get 20% off the entire order up to a maximum of $100 in savings. So say you were planning spending $500 this holiday season on Amazon, if you register for the promo and then spend that amount in one order and apply a single MR point, it will cost you $400. That’s damn incredible. So any way, check here to see if your account is targeted for the promo. If it says you aren’t eligible, click here to make sure your American Express card is linked to your Amazon account. If it’s not, link it and then go back to the promo signup page and see if the offer then shows up.

The Chase offer is similar. Use a single UR point and you get $15 off a purchase of $60 or more. Check here for the promo. Link your Chase account Amazon first here if needed.

Now the reason you just want to use just a single point toward your purchase and not your entire points balance is simple: without the promo, points are worth just .7-.8 of a cent toward Amazon purchases and that ain’t pretty.

Cyber Monday is tomorrow (which for people like me if better than Christmas itself) so it’s a great day to take advantage of these promos. You can find Amazon’s Cyber Monday deals page here. Another great thing about the Amex/Chase offers, you can get the promos even when buying gift cards, basically all gift cards besides Amazon’s own.



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How to Save a Ton by Buying Discounted Gift Cards

Credit card points are passion, but I’m always looking for ways to save money in other arenas. One of the best ways: buying discounted gifts cards. This used to be pretty shady area. There were a ton of scammy sites and it was almost impossible to figure out which sites were reputable. Well, I’ve done the heavy lifting for you. Over the past 5 years, I’ve saved about $2,500 by purchasing discounted gift cards from Raise and Cardpool. To be clear, I used all the gift cards to buy stuff I was already planning on buying anyway. Just tonight, I bought a $25 Chili’s gift card on Raise for $20 and then used it five minutes later. It took me about 30 seconds to buy the gift card on the Raise app. 30 seconds for $5 bucks? Not bad!

If you do buy a bunch of discounted gift cards, once in a while you will run into an issue where a card has been drained by a scammer or it doesn’t have the right amount on it. I would say this has happened 3-4 times between Raise and Cardpool, but I have purchased hundreds of gift cards from them with no issues and both sites offer a 1-year money back guarantee. If you buy a card for $50 and then go try to use it the next day and it has nothing on it, you just email them and you will get your money back.

Now obviously you shouldn’t be reckless. Don’t buy a $500 gift card and then try to use it 3 years from now. I usually use these sites for spur of the moment purchases. You’ll often find the biggest discounts on restaurant cards.

I love Raise and Cardpool, but I’m partial to Raise because 1) you get e-gift cards within minutes (it may take longer for your first order) and 2) the mobile app is awesome. With Cardpool, there have been a couple of times where I have ordered a card ready to buy something online and then it doesn’t get sent to my email for a couple days.

So yeah, buy discounted gift cards online. You won’t get ripped off if you stick to these two sites. You can use my Raise referral link here and save $5 on your first order if you so choose.

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Capital One Venture Card Bonus Up to $750

Whoooaaa. This is one of the top credit card signup bonuses in credit card signup bonus history. Capital One has just increased the bonus on its popular Venture card from 50,000 miles to 75,000 miles. That’s $750 in statement credits toward travel purchases. You do need to spend $5K in three months instead of the $3K that was required for the 50K bonus. But the annual fee of $95 is still waived for the first year.

So let’s say hypothetically that you are currently spending $20,000 on your debit card annually. Damn, it pained me to even type that sentence. But anyway, if you apply for the Venture, get the signup bonus and put that $20,000 on the card, at the end of year 1 before the annual fee hits, you will have made $1150 between the signup bonus and the 2% cash back you get on every purchase.

The point: if your credit score is solid and you can hit that $5K in spending, you should be applying for the Venture card right now.

Bonus: You can change the image on the Venture card once a month and you can use your own photos, which is pretty cool. I get a new version every month with a new photo of my kids on it and when they get older, I’ll give them all the old cards and they will be like, wtf dad, this is weird.

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