Lesson 2:
Learn the rules of the game
The first rule of flight club
CEOs and other high-ranking managers have to be discerning in how they provide feedback, otherwise an off-hand remark can have unintended consequences.
Jeff Weiner, Executive Chairman of LinkedIn, created a shared vernacular for his teams to better understand the severity of his feedback, through a ratings system:
Mandate - this is a top priority and must get implemented
Strong suggestion - you have the final say, but you should consider this
One person’s opinion - take it or leave it, just an idea
There are a few mandates when it comes to credit card rewards, once you understand them you’ll be able to best determine which combination of cards (aka stack) is right for you.
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San Sebastian, Spain
Lesson 1 Recap
We covered the value of a point, key takeaways being:
Cards that accrue flexible points are more valuable than specific airline or hotel cards
When redeeming points, it’s best to avoid your credit card travel portal which redeems points at a cash rate, and instead transfer your points to a specific hotel or airline
Before you transfer points, check for availability of the reward you want to redeem
If you have multiple ways to redeem the same reward, check to see if there’s a limited time transfer bonus available and/or a “sweet spot” redemption
Èze, France
Lesson 2: Rules of the Game
We can break down card mandates into two categories:
Card-issuing bank rules: Hard and fast quantitative rules from banks limiting the number of cards you can sign up for within a given time period or that you hold concurrently. Despite your excitement levels, it’s important to remember that this is a long game and a “quick win” is actually a loss if it jeopardizes good standing with a financial institution.
Financial well-being best practices: My personal mandates for anyone new to the space, these are more qualitative and extend beyond rewards cards.
Card-issuing bank rules
Each bank has their own variations of the first rule you need to consider before applying for a new card. How many credit card accounts have you opened in the past X days or months?
Note that a * denotes all cards, not just the specific bank.
American Express 2/90 - max of 2 new cards within 90 days, 4-5 card total limit
Bank of America 2/3/4 - max of 2 new cards in 2 months, 3 in 12 months, 4 in 24 months
Barclay 6/24* - max of 6 new cards within 24 months
Chase 5/24* - max of 5 new cards within 24 months
Chase Sapphire 1/48* - 1 Sapphire card every 48 months, limit 1 at a time
Citibank 8/65 - max of 1 new card in 8 days, 2 in 65 days
Capital One 1/6 - max of 1 new card every 6 months
Discover 1/12 - max of 1 new card every 12 months, 2 card total limit
Business cards - note that most banks do not count business cards toward your total
Financial well-being best practices
The rules above can feel overwhelming. You may be asking yourself how you can navigate all the complexity, but don’t worry about that. The most important rule to keep in mind above is the Chase 5/24 rule since it entails all new account openings. We’ll readdress that in the next section, but let’s create a foundation through some financial best-practices.
Security - financial health starts with securing your assets through good password hygiene.
Login email, your account login shouldn’t be the email you share with the world. Make up a random email address that isn’t traceable to your name and that will pay dividends in securing your accounts.
Passwords, you need a password manager, I’d recommend LastPass or Dashlane. Instead of remembering hundreds of passwords, you should only need to remember two: the password to your password manager and the password to your main email account.
2FA, aka two factor authentication is usually done via annoying text messages. Those present a security vulnerability via SIM swap attacks, which you can prevent by (1) calling your cell phone carrier and ensuring you have a PIN on your SIM card and (2) by transitioning from SMS texts to a 2FA app like Authy.
Paperless, sign up for paperless statements to limit sensitive mail.
Learn additional tips here.
Privacy - learn how to opt-out of affiliate marketing and more here.
# of Cards - the number of cards you open will be in-part determined by your baseline spend and whether you’re going about your journey solo or with your significant other.
Baseline spend, if you look back at your credit card bills from the past 12 months, how much did you spend on average for each month? This is your baseline spend. Neglecting other financial goals and budgeting, this baseline will help you decide whether a minimum spend requirement is within your budget.
Solo vs with partner, solo travelers should prioritize their current spend habits, but if you have a partner, you should take into account both of your budgets. Perhaps P1 is responsible for groceries and dining, while P2 covers airfare and hotels. In this instance P1 may want to consider the American Express® Gold Card for 4x points at restaurants and US supermarkets (up to $25k in purchases per calendar year), while P2 prioritized the American Express® Platinum Card for 5x on airfare, Clear membership (enrollment required), and Centurion Lounge access.
🔑 1-3 cards per year - For most of us, 1-2 cards per year are sufficient for an annual epic vacation. Those who have higher baseline spend and/or fewer starting cards may be eligible for 3 cards during your first few years, especially if you own your own business.
Organization - Before signing up for new cards it’s important to start tracking your existing cards and their anniversary dates. I’d recommend a simple spreadsheet tracking account open date, whether you signed up for autopay, met your spend bonus, and account anniversary. This will serve you well when cross-referencing the bank rules above.
Fenix Beach Cartagena, Columbia
Building your Stack
Now that we understand the rules, it’s time to build our stack. By now you should know:
How many cards you currently have, and how that impacts bank rules
Your monthly baseline spend
Whether you’ll be doing this solo or with a partner
Each of us will differ when it comes to existing cards, baseline spend and desired rewards partners, but we should all look for the following traits in a credit card offer:
A large selection of 1:1 travel partners. For those who have a favorite airline or hotel, you may want to ensure that they’re a transfer partner.
Achievable minimum spend with a large bonus, at least 10,000 points per $1k in spend required. Yesterday’s Venture X offer was 75k points for $4k spend.
An annual fee with a clear path to being valuable for you. Annual fees can vary from $0 to over $500, but often offer outsized value if (and only if) you utilize the services being offered to you, especially if you would have paid for them regardless.
A great example of a card with a lot to offer for those who take advantage of it, is the AMEX Platinum, read more in the review below.
🍬 Sweet Spotlight: Hyatt
Yesterday’s sweet spot to Japan was a great example of very high value, yet very difficult to book. Today, I wanted to detail a sweet spot that’s not as extraordinary, but super easy to book making it approachable for someone who’s just getting started. That sweet spot is the World of Hyatt rewards program.
Hyatt is on the smaller side of the multinational hotel chains, with roughly 1100 properties in 69 countries across six continents. Whereas Wyndham, Marriott, Hilton & IHG have multiples of that, here is a full breakdown for the nerds. Despite having a smaller footprint, their rewards program is easy to navigate and my experiences at their properties have been top-notch.
Hotel chains categorize properties via a leveling system, Hyatt uses a 1-8 scale, with Category 8 implying luxurious and very well located. Here’s a look at the rewards chart:
Hyatt Rewards Chart
If you consider the cost of a point being a penny each, you can quickly see how valuable these rewards are. Starting at 3,500 points for a room that retails around $80, netting you over 2 cents per point. To the higher end, like the Park Hyatt Paris-Vendôme category 7 which retails for roughly $1,300 per night, yielding 4.5 cents per point.
Another joy of Hyatt is that they cover resort fees when redeeming points for a free night. This is particularly valuable at all-inclusive resorts and travel destinations like Hawaii, Fiji, the Maldives. If you’re looking to stretch your points, I’d recommend saving your luxury stays for Sunday - Wednesday when redemptions can be significantly less and the hotel is less crowded giving you more space to enjoy it.
Milos, Greece
When we talk about outsized value, this is a prime example of a card that offers a lot but unlike the Venture X, it’s a little more difficult to quickly see the value. That said, the Platinum card has the best lounge access, fantastic customer service via chat bot, and the only concierge that has consistently been able to get me reservations at Carbone NYC (obviously your results may vary).
What else does this card offer?
Earn 80,000 Membership Rewards® points after you spend $6,000 on purchases on your new Card in your first 6 months of Card Membership. ($800+)
$200 Airline incidentals credit ($200)*
$200 Fine Hotels & Resorts credit ($200)
$200 Uber or Uber Eats credits (delivered monthly) ($200)*
$100 Saks Fifth Avenue credit ($100)*
$100 for Global Entry or TSA Precheck every 4 years ($25)*
$189 Clear credit (combined with United Silver covers cost for 2 people)*
United Silver Status*
Hilton Gold Status*
Walmart+ membership ($155)*
Centurion Lounge access
And many more limited time offers accessible online or in the app
* = requires enrollment
The card has a $695 annual fee (The Platinum Card® from American Express - Rates & Fees), but it’s easy to see how that fee would either make up for itself or simply be worthwhile to elevate your travel. Don’t get me wrong, these credits are not as easy to utilize as yesterday's Venture X, but there’s so many of them that there’s bound to be something you’d enjoy.
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🐰 Continue Down the Rabbit Hole?
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