EP 580 – Gamifying Your Credit Card Points With Jack Krupey

NCS 580 | Credit Card Points

NCS 580 | Credit Card Points


Believe it or not, you can travel the world at super discounted airline ticket rates using your credit card points. With an Amex or Citi card in your wallet, you can start your quest for increasing points and enjoying freebies thereafter. Today, Scott Carson talks with his long-time friend and note investor, Jack Krupey. Jack is a Principal at JK Asset Management and the Founder of Gemini Capital Managers. He talks about how he has utilized his travel and credit card points to gamify his travel with his note and real estate business. He explains how he leverages the value in what the major credit cards offer in multipliers. Learn more from Jack as he reveals some of his tricks to winning in the credit card point game.

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Gamifying Your Credit Card Points With Jack Krupey

Many of us, as entrepreneurs, are traveling. You travel for workshops. You travel for seminars. You travel for vacation. You travel to look at a property. A lot of us have some pretty hectic travel schedules or using our credit cards to build points or a variety of things. We would love to get a lot more points. I’m excited that my good buddy, Jack Krupey, is going to join us on this episode. I’ve known him for years in the note business. He is one of the first people I was buying deals from. He has done a great job on how to leverage his points, his credit cards and all his rewards flying or traveling for almost free or at a reduced cost. If you ever want to do that, tune in to this episode and I guarantee Jack will help you get to the top when it comes to it.

In this episode, we’re going to take a little bit different twist on some things. You are going to love this. I’m honored to have a good friend of mine. We go back many years now based on where everything is at in the market and how we met originally. This man is a longtime friend of mine from the note business. He founded a trading firm that merged the large private equity fund, a big fund that was focused on buying bankruptcy notes. He left to preserve consulting and other investment opportunities. He started in Rochester, New York buying rentals, fix and flips. This guy has done amazing stuff. He’s taking leaps and bounds and doing some great things like that. In addition, he’s still being involved in the note business. He’s going to share about one of his passion projects that you all can implement using credit card points and miles to travel the world almost for free. We’re honored to have the man, the myth, the legend, my friend, Jack Krupey join us. How’s it going, Jack?

I’m doing great, Scott. Thanks for having me.

You’ve done some great things and traveling all across the world. Why don’t you give us a little bit more background or how you got to decide to make that pivot into what you’re doing right now?

As the firm grew, I was traveling a lot more for conferences to visit vendors and servicers. Our business expenses also started growing. I had tens of thousands of dollars a month in travel and business expenses. I’d heard through a friend of a friend that was able to fly business class for free. He’s a fellow big guy like you are and I despise flying in the back of a plane or the middle seat. I wanted to figure out a way to do that economically. I found some of the more famous blogs like The Points Guy and started researching. I’m also always looking for different investment opportunities. For a few years, I learned a number of tricks on how to generate Amex points, Chase Sapphire points and transfer them to airlines and fly business class or first class, and in some cases for free, a few hundred dollars in value. It was money I was already spending.

The first thing I’ll say is I’m not going to advocate for anyone to run up credit card debt. This is targeted especially to your network of note investors, real estate investors or people that likely already spend $20,000 a month at Home Depot, for example. Should you put that on a card that gets 2% cashback or put that on a card that earns points worth $0.05 to $0.10 a point if your goal is to maybe fly to the Maldives, go to Tahiti or take one of these epic vacations, which is something I’d been able to do a lot of over the last couple of years. The reason I got started is I found a mistake fare. I remember it was the day after Christmas 2014. I was sitting at home. For about two hours, Delta had mispriced pretty much their entire inventory.

I was on a site called Google Flights, which you can put a map up. It will give you from your home airport, all the prices in different markets. I pulled it up for fun. I saw that Hawaii was $36 for an economy ticket. At that time, it’s cheap, but I wasn’t necessarily pricing out Hawaii. I switched to business class and it was a $140 round trip for an eleven-hour flight in business class on Delta. I called my wife at work. I was playing with random days. I was like, “Should we do it?” We decided even if we can’t go for $140, we booked Valentine’s week trip to Hawaii. That was the first time I’d flown a real business class where the seats lay flat. I was hooked from there and I spent the next couple of years of my life constantly reading blogs, the forums and trying to find every tip and trick.

Coincidentally, as part of my investing research, I came across some advisory firms that sell operating websites that are making money. Many of these sites you can buy at three times the annual profits. I found a site in the points and miles space. It seemed like fate. I’d been looking at potentially buying blogs or other cashflowing assets and online stores. I found a site that was in the points and miles credit card space. I purchased a site called CreditShout.com in March of 2017. It’s been around since 2009. I’m the third owner of the site at this point. It has roughly 1,800 pages of articles, blog posts, tips and tricks. I’m adding my spin to it with some more detailed points and miles posts.

Some people don’t think about that. We talk about debt. We’re both in the mortgage space. I always make the rain joke that if you’re not in the note space, you already are because you’re usually paying out versus it coming into you in a variety of ways with assets. You leveraged what you’re already paying out, expenses, travel costs and day-in-day-out operation stuff to help you to get the points to transfer over there. Where’s the good starting point? Are we talking about major credit cards like from a major bank that’s backing them or are we talking like a subset?

It’s a major credit card. I prefer to use the transferable points currencies, which are Amex and Chase, as the two major carriers. In some cases, Marriott and now Capital One and Citi all have points that you could transfer to different carriers. Generally, you get more of a bang for your buck using either an Amex Gold or a Chase Sapphire preferred or reserve than using an airline card or hotel card. For example, I have a Delta card, which I use for certain status benefits, but for my day-to-day spend, an Amex Gold card. You get four times points on all restaurants and three times points on all grocery spend.

For those same spends, if you use a Delta Sky Miles card, you’re only getting one point per dollar. To make things even better, Amex points will transfer directly to Delta. If you want to earn Delta miles, you could still do that. I know you’re a Southwest guy primarily, but other than the status, similarly the Chase Sapphire Reserve card, you earn three times points on restaurants and all travel and those will transfer to Southwest. As long as you’re not spending specifically for the companion pass, you’re better off using those cards for your day-to-day spend. Both of those cards do have annual fees, but there’s a fair amount of benefits you get with those that generally offset the annual fee. One of the best tricks I have is to pull the fee version and a no-fee version of the same card.

For example, Amex has a Gold Card where you earn four times on restaurants and three times on groceries. Amex also has the Everyday Card where you earn 1.5 times points on all your other spend. This way, no matter what, you’re earning roughly $0.03 to $0.04 per $1 spent depending on where you value the Amex points. The floor is $0.01 per point. The points are worth at least $0.02 a piece and I’ve redeemed them. For example, I flew Lufthansa’s first-class, where a round-trip ticket is $15,000. I used 200,000 points for $15,000 flight. It’s like a bucket list type item. I would never spend that amount of money to fly Lufthansa even though it was an amazing experience.

You’ve been traveling quite a bit, not domestically but internationally, back and forth for a variety of reasons. Do you want to share doing that and why this is valuable?

As I was winding down my time at my fund, I was looking at doing an executive MBA program, Master’s in Business. I went to a few different info sessions. What I found is people that did the global programs enjoyed them. You’re generally with a slightly older and more established group of more senior executives. You visit different countries and stay in a hotel with your entire class a week at a time and you take 1 or 2 classes with people from all over the world. I was able to get into the Kellogg Program in partnership with the Hong Kong University of Science and Technology. Every six weeks or so, I flew to Hong Kong. That’s something I never would have been able to do or wanted to do if I was flying in a middle seat in coach for fifteen hours.

NCS 580 | Credit Card Points

Credit Card Points: You can transfer credit card points to your airline miles points and use it to fly for free or at discounted rates.


Fortunately, I used it as a game and a challenge. I used Amex points to fly Japan Airlines. I used Alaska miles to fly Cathay Pacific. I’ve tried all these different airlines and I was able to also visit some other cities too. From Hong Kong, it’s so centrally located in Asia, I was able to visit Chiang Mai, Phuket, Thailand, Japan and Korea. It was an incredible experience that I never would have been able to do. I’ve also taken three-day weekends to Europe. If I had to sit in the back of the plane, I probably wouldn’t have done it. For practically free, I’ve been able to visit friends in Amsterdam. I ran into Wayne Snell randomly. He’s another note investor in Amsterdam. He was there for a concert and I was just passing through. It’s unlocked some incredible experiences.

That’s the beauty of it. If you know how to leverage that, know the value in what your cards offer, the multipliers and who does what, it’s a valuable thing. You outline a lot of this on your website with the different points. You gave me a very valuable tip. If you’ve got a fee version of the American Express Gold card or the non-fee one, they have different advantages. Do you use them for different things?

There’s a lot of content and we’re continuing to build out the content on the cards. I’m more than willing to do questions and answers via email or on our Facebook page. I got into this because a lot of my friends started asking me, “What do I do?” or, “I have these many miles here. I want to go on this vacation. How do I do it?” or friends that are business owners that never paid attention to it and said, “I’m spending $30,000 a month on expenses. I’m using my standard Amex Platinum card. Should I be using something else? What can I do with these miles?”

I found in this industry with so many real estate investors, we’re the type of industry that could take advantage of this. It seems like it’s something that fails to crack and people are focused on their daily lives. It’s a very simple thing to do to unlock a lot of opportunities. There are also domestic opportunities too. I don’t have kids. I’m able to travel the world a little more freely. I know people who’ve taken their families to all-inclusive Hyatt properties on miles points either through the Hyatt Card or through the Chase Sapphire program. Those points transfer to Hyatt at very good rates. You can go to Cancun, Jamaica, Cabo and stay in 4, 5-star, all-inclusive resorts on points of miles, which saves thousands and thousands of dollars.

Have you taken a look at what we are spending on that? We’re going to put it on the card and then pay it off at the end of the month versus using our debit cards from our accounts that we can maximize.

Yeah, I never advocate carrying a balance. It’s funny because my wife gives me some crap sometimes because I’m a little bit all over the place and ready, fire, aim in certain parts of my life. On the credit cards, I’ve put a Post-it Note on her credit card that says, “Use this at the grocery store. Use this for this expense.” She goes, “You’re so detailed with this. Why can’t you remember to put your socks in the hamper?”

What was the biggest thing initially? Flying with Lufthansa is a great thing. What’s another thing that you were surprised like, “I can do this thing?” What was the big first surprise for you with everything you’re doing with your credit card?

How quickly the points seem to add up without trying when you’re earning four times points for restaurants. At the time, I was living in New York City and restaurants and groceries are probably the two biggest expenses. I’d imagine for most people in this country, those are some of the highest expenses. If you’re spending a few thousand a month on groceries, if you do this for a year and pay it off at the end of the month, as you would anyway, you could have over 100,000 points. There are also pretty lucrative signup bonuses. In the first year or two, I’m not advocating to purposely get a card for the bonus, but there are different cards for different purposes.

Over the first few years, you can amass a few hundred thousand extra points from welcome bonuses for spending a few thousand over a few months. A lot of the annual fees are paid for through certain benefits. I do hold a few Marriott cards because they give one free night. It’s an $89 annual fee, but I’m usually getting a $150 hotel room. When you spend specifically on that hotel room, it gives you four times points on your spending. It does make sense to do that. How quickly they added up, I’ve probably built up a million-plus miles in the first year from a couple of credit card bonuses and focusing on being efficient with my spending. You can be that person at the restaurant, you’re out with a group and some people have cash, throw your card in and take cash from everybody else. That’s an easy way to run up a lot of points without spending more money.

You reminded me of the movie Up In the Air with George Clooney and Anna Kendrick. Four million points and the pilot come on and say, “It’s nice to meet you. Here’s your card.” You can travel a lot. You just carry a backpack with you in a lot of cases. For those that are reading this episode, CreditShout.com has got some great featured articles on here, Best Cash Back Cards, Best Credit Cards: Editor’s Picks, Top Deals and Best Air Miles. You’ve got great articles on this stuff and deliver a lot of things. You talk about some other things besides credit cards. You have different wireless things and stuff like that too?

One of the articles that gets a lot of traffic here is people trying to figure out what credit score you need for cell phones, given the iPhones are over $1,000. They do run a credit check to get a cell phone. There’s some information on Verizon and AT&T and what their requirements are. Most of your audience that is full-time real estate investors may be less concerned about getting approved for a cell phone, but it does have some interesting information available. The beginner’s guide is ongoing. That post is going to be updated regularly. I’m working through most of what we’re talking about here, trying to update reviews for every single card.

It does talk a little bit about the transferable points that I covered here. First, it covers how to get your score for free. We have links to Credit Karma and Credit Sesame, and which types of points depending on what your goals are if you’re looking to fly in business class. It’s probably the best. I keep going back to that because if you like to do that, it’s the overall best value. Sometimes you’re getting $0.10, $0.15 a point for those types of trips. It covers hotels and other avenues as well. What I’m going to work towards overtime is some of the interesting loopholes.

I mentioned a lot of my friends call me for advice on more custom trips. There’s so much content. It’s hard to get it all on paper. A lot of the obscure foreign programs, for example, you can transfer American Express points to all Nippon Airlines. It’s Japan’s number two carrier and they have some incredible rates where United may charge you 115,000 miles each way and they may charge 60,000 miles each way. It’s almost half the price to book on a foreign carrier. In some cases, you could book United flights using a foreign carrier at the same price. That’s the same thing for Delta. You could use Virgin Atlantic miles and book Delta flights cheaper than Delta itself.

We’ve experienced that when we flew on Virgin when we fly overseas. We don’t fly in the first class. We take the business class seats as you can get some great deals there and find some great bookies. I’m willing to imagine with everything going on, travel is to be even cheaper as the airlines are trying to bring people back in, try and give you a comfortable traveling. What’s your opinion on that?

NCS 580 | Credit Card Points

Credit Card Points: Welcome bonuses from different cards can be amassed and used for specific hotel or airline fees.


Travel is going to be cheaper for the short-term. I’m even seeing it now. They’re trying to incentivize bookings for summer or fall. It’s important in the next few weeks to stay safe, hunkered down and follow the rules. I am looking for speculative bookings in the fall. If I find a great deal in September or October to go somewhere, I’m not afraid to book it now. Points and miles are also more available. When planes are full, they always have a space available for award tickets, but not on every flight, every day. It’s going to be much easier now to book something on points. Most of those points bookings are fully changeable up until sometimes 72 hours beforehand. If you want to speculatively book a trip to Europe, now is a great time to look for options. In a way, it’s patriotic to support the airlines, support the businesses and help them with their cashflow and find a great trip for yourself.

I was looking at the news and they were talking about how hotel bookings are down to 50% compared to normal 75%, 80% where it is now versus it was a month ago. Especially here in Austin, average rates were $175 a night and it’s down to $125. It helps because South by Southwest was going on. It was supposed to be taking place here, but now it’s been canceled. I’ll give you an example of something drastically happened with the cruise lines. We’re a big fan of cruises. Disney is doing a thing, “Book a cruise right now. If we end up having to cancel, we will give you 125% of the value of what you paid for the new one.” You can use points to pay for that and come out even bigger a hit for a bigger cruise you want it to.

The points are 100% true and I think this thing will run its course. We’re taking drastic steps. Things will stabilize in the coming weeks. People have a lot of time at home right now too. It’s a good time to do a little research and try to find a way to get out of the house after being cooped up in the house.

I had a student of mine who did one card. He owned a supplement company. He paid for every bit of shipping. It was charged through his Amex Silver card every month. He was taking those points and doing everything he wanted to, travel and all this stuff. This is a couple of years ago, but it’s evolved. It keeps getting more and more advanced. Different things and perks are becoming much more available, like you said, different hotel cars and different airline cards. If you go to Virgin, try to book a flight with Delta there, it’s often cheaper in Virgin versus the other way around because we’ve seen that.

We’re even supposed to be flying on Virgin, but it’s not operated by different carriers and vice versa. The fact that points can transfer makes it often a lot easier versus being second and we fly religiously on Southwest because it’s easy in and out. I’m usually the first guy on. I get the exit row seat for the extra room. The thing is to look at what you’re doing. You can capitalize on some of the stuff. Have you had the credit cards send you any other stuff? Are you getting other increased lines of credit if you’re using this? Are your limits going up because you’re using this and cashing them in and out regularly?

My score went up as well. I had a couple of challenges after 2008. My score wasn’t exactly a perfect post-financial crisis. One of the things is a lot of people get concerned about having too many cards and doesn’t hurt your credit score. If you’re going to get a mortgage in two weeks, maybe it’s not the time to open a card, but the major metrics that the banks use is, what is your credit? What have you drawn on your cards versus your available credit? If you only have one card, you have a $20,000 limit and you spend 15,000 at Home Depot. Even if you pay it off in two weeks, before the end of the month for that period, your score is going to drop.

However, if you have 4 or 5 cards and now you have $100,000 in available credit and you have that same $15,000 bill at Home Depot, you’re below 30% utilization and that helps things. It’s good to have a few cards and a few options as long as you’re not carrying a balance. A lot of the cards have different perks and they’ll run short-term spending bonuses, “Spend $2,000 on this card on this month will give you triple points.” Amex and Chase both have offers where you’ll get 15% off on Macy’s one month or Chase, for example, has rotating bonuses to their Freedom card, which is their free card. Every quarter they have a 5% cashback.

When you have the Chase Freedom and you have the Chase Sapphire, you can transfer points between them. It’s essentially five times points if you want it that way. Sometimes it’s on gas. Sometimes it’s on a certain store. I get a hundred dollars off on Dell every six months from Amex. It’s hard to track, but there’s a lot of different things. One of the other things I use is AwardWallet. It’s like Mint.com, but for tracking your airline programs. I’ve signed up for a lot of those secure programs like ANA. I don’t have Delta and Southwest. I probably have twenty different frequent flyer accounts. You put in your usernames and passwords and it tracks all your miles.

It’ll tell you if something’s going to expire. That’s another valuable thing. I’ve helped people save hundreds of thousands of miles that were going to expire by transferring 1,000 Amex points. It will keep the miles alive for another year or in some cases, you sign up for a magazine subscription or there are dining programs where you link your card to a dining program. There are so many little intricacies that don’t take much time but do add up over time. It’s addicting. If you’re the type of person that gets into trying to be efficient and make a few extra bucks, it’s addicting. It’s a bit of arbitrage. I find that most people that play poker also love points.

It’s another version of poker for the most part or it’s a debt game and things like that. Figure it out, “How could I use this with transferring come out ahead,” or vice versa. There’s a lot of little backdoor loopholes if you don’t know you’re going to miss out on things. Jack has done a good and that website has done well. Are there any other websites you’ve purchased that have been valuable with the optimization that you’re seeing?

I have one other one that’s in a joint venture. It’s called a mess-free, stress-free life. It sells eBooks on how to organize your house. It’s very ironic because I’m not very organized, but I purchased that in a joint venture with another group. It is a property manager for web businesses. This has been a pretty new initiative for me. I’m looking very heavily at everything from cashflowing blogs, blogs that sell eBooks. My wife has been pursuing Amazon. There are Amazon businesses for sale. It’s a little tricky time for that now, but people will import products from Alibaba and set them up on Amazon. It’s a relatively turnkey business. You do need to order products. There’s a lot of research to get it started but once it’s up and running and you’re ranking, it’s another cashflow stream. I look at a digital real estate and the returns can be pretty lucrative. It reminds me a bit of note in 2008, ‘09 and ‘10 when the returns were quite lucrative. I’m digging in pretty heavily in that space. I may launch small syndication at some point, but I’m still working out the kinks on my properties for now.

We’re not going to see a repeat of 2008 and ‘09, but we’ll see a bit of a tick in the market when it comes to foreclosures and defaults here with everything going on. Don’t you think a little bit?

Pricing at an institutional level has got aggressive over the last few years. I certainly don’t wish any harder heartache on actual homeowners to default. My hope is that this scare and what’s going on in the overall credit markets does maybe bring pricing down a few notches. The larger seller is going to price in maybe slightly longer timelines and more defaults because of the hiccups and more loans are going to shake loose and be available for the smaller buyers, which at this point is what I am again. I’m consulting and I’m working in-house brokering some larger deals for clients. Otherwise, I’m still looking to buy some loans personally too. I hope it recovers.

Real estate is not the cause of the issue this time. It’s a short-term panic. I’ve always preached to modify the loans when it makes sense. A lot of these situations where people had a short-term hiccup was a great opportunity to buy something and do a modification, either forgive or a couple of payments at the end of the loan and help borrowers re-perform. That market will continue to re-perform. That market, back when you and I met, it barely existed. In some cases, you were afraid a loan will re-perform because it might be worth less. With interest rates going to zero, there’s a huge demand for performing cashflow on paper. If you have mortgages at 3%, 4%, 5%, 6%, that’s 3% higher than the fed rates. I do think there’ll be continued demand for performing paper.

Credit Card Points: It’s good to have a few cards and a few options as long as you’re not carrying a balance.


Most people don’t know, but Jack and I met for me doing a sweaty ass video and throwing it on YouTube on a condo walkthrough that I was doing originally back in the day. He’d bought a couple of notes from Chase Bank, two condos in the same unit. My video was the only bit of marketing you could find on that complex out there. I got a phone call from the guy with a New York number and I’ve seen these other two assets on another tape. We looked at the same tape, he bought and beat me to them. He called me and said, “Are you calling about 105 and 107?” He’s like, “What the hell?” We hit it off from there. Jack, I appreciate you for coming on here. Everybody’s in the note business. You have turned the credit card flow more back towards your way versus the outflow, which is awesome there for you. What’s the best way for people to connect to get ahold of you? Can they go straight to the website?

From the website, you can email us at CreditShout@gmail.com. We have an Instagram and a Facebook page. There are some affiliate links on the site. If you’re thinking of applying for a card, feel free to email or reach out online for some customized advice. We appreciate it if you go to CreditShout.com first and then click through to one of the affiliates if you’re going to apply. Especially for your audience, we happen to give our guidance on what we think is maybe the best fit for you.

You have a safe quarantine there in Puerto Rico and enjoy it.

It’s been a real pleasure. I’m glad we could catch up and I look forward to doing it again.

We’ll take Jack up on his advice, counsel and his experience. This man has been flying all over the place. I crack up with the photos I see every time because he’s not a middle seat guy neither am I. He is stretched and laying out. It’s almost like the flight attendant shows up with silk pajamas from the Crazy Rich Asians movie there. Go check out his website and we’ll see you all at the top.

Important Links:

About Jack Krupey

NCS 580 | Credit Card PointsJack Krupey is a long time friend of mine from the note business. He founded a trading firm that merged with a large private equity fund and left last year to pursue consulting and other investment opportunities. In addition to still being involved in the note business I’m going to talk to him about one of his passion projects, using credit card points and miles to travel the world almost for free.

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