I wrote this guide to help founders get the most from their business and personal spending. As a founder, money has always been tight, but setting up simple systems for my business and personal spending has allowed me to travel the world for free, reward employees, and reduce our company’s burn.
Unfortunately, this guide only works for US credit cards that are issued to people with US Social Security Numbers. Many of the best cards require a fairly high credit score. If you don’t have an established credit history because you’re young or recently arrived to the US, scroll to the bottom for some tips or send me an email and I’ll do my best to help.
See you at the airport!
Spencer, YCs19
Questions, feedback, or want to schedule a free consultation call to make sure you’re getting the most from your credit card spend? We have a small team of experts that can help you set up and run these systems.
[email protected] || 412-436-9760 || calendly.com/spencerburleigh
TLDR:
If you don't already have some cards that earn points I'd start with a travel card that has some benefits (Chase Sapphire Reserve or Amex Platinum), and then a ~2% back card like the Venture X.
All these cards have big signup bonuses that will get you a free business / first class ticket after spending $3-$5k.
You can sign up for business credit cards too. I typically do one business and one personal card every 6 months.
If your business spends a lot (>$10k / year) in any special category like online ads, postage, or office supply stores it makes sense to get a card that gives you bonuses for those categories
Table of contents
Table of contentsGolden rule: earn at least 2%Just getting started? Pick an ecosystem that matches your goals / desired effortBest Programs to Start WithOther programs to considerPowerful if done right: Citi ThankYou PointsMost valuable (and most work): American Express Membership RewardsSimplest high-value program: RampSimple program, recently devalued: Brex RewardsStart with these cards Earn ~2% back on each dollar purchasedEarns >2% in the categories you spend the most moneyConsider a specific airline’s or hotel’s credit card if you spend a lot of time or money with them How to think about annual feesThe first year is almost always justified by the signup bonusReconsider if the card is right for you each year.Expert tip: always try and get retention bonusesTurbocharging your points with signup bonusesBefore you do this:I follow this strategy:Open a new personal card every 6 monthsOpen a new business card every 6 (possibly 3 months)How to go/stay where you want for freeEarn Free Flights (my favorite)Airline listEarn Free Stays & Status with HotelsHotel transfer partnersObscure and not covered by this guideAspirational Awards & How to Book ThemFly the World’s Best Airlines in First / BusinessLufthansa First Class to Germany / EuropeCathay Pacific First Class to Hong Kong / AsiaANA First Class to Japan & AsiaSingapore First Class (Suites) to Singapore (or NYC - Frankfurt, Germany)Emirates First Class to Dubai & BeyondQatar Q-Suites Business Class (world’s best) to the Middle East & BeyondStay at the World’s Best HotelsAmericasEuropeMiddle EastMaldives / Bora Bora / FijiAsiaAustralia When are credit card points not worth itA note on ownership of credit card rewardsWhat to do if you can’t get approved for the cards you wantStep one: call the reconsideration lineProblem 1: not enough credit historySign up for easier cards to getBuild a relationship with the issuerProblem 2: too many recent credit pullsConsider cards from different issuersSometimes you have to wait 💔Further readingFlyerTalk ForumsOne Mile At a TimeView From the WingPointsGuyDisclaimer: All the things linked in this guide:Credit card programsAirline alliancesHotel programsComprehensive list of all the credit cards we think are worth considering (ranked by signup bonus value)Argomy can help you set up and run these systems
Golden rule: earn at least 2%
If you and your company spend a lot of money on credit cards, you should be earning at least 2% of that spend back in the form of cash back or miles. Using the right credit cards can also have benefits for you and your employees such as:
- extending manufacturer warranty by an additional year
- trip delay insurance (pay for a hotel if your flight is delayed)
- baggage delay insurance (pay to replace the contents of your lost checked bags)
- emergency medical evacuation
- access to airport lounges
Just getting started? Pick an ecosystem that matches your goals / desired effort
Start by learning about and getting cards from just a few of the major issuers. Learn what the strengths of the program are over time and get good value from them. It’s better to earn a lower number of points and really know how to use them than to earn more points but not fully reach their potential.
Best Programs to Start With
Easiest to get good value: Chase Ultimate Rewards
Best Cash back: Bank of America Preferred Rewards
Bank of America has the best-earning cash back card (2.62%) if you open their “Preferred Rewards” account.
Preferred Rewards requires you to keep $100k in cash or securities like stocks / bonds with Bank of America through your business or personal account.
Bank of America cards typically don’t have annual fees.
Most straightforward points: Capital One Rewards
Capital One offers a few very strong cards.
Points transfer to strong partners like Air Canada British Airways , and Turkish. They can also be used as a statement credit worth 1 cent / point.
Some Capital One cards have annual fees but they usually pay for themselves.
Earn points on rent: Bilt Rewards
Bilt gives you points on up to $50,000 / year in rent.
Since you can’t typically earn points on paying rent you should probably get this card eventually.
There are a lot of cards that can get you more value when you’re just starting out.
Other programs to consider
Powerful if done right: Citi ThankYou Points
Most valuable (and most work): American Express Membership Rewards
Simplest high-value program: Ramp
Ramp is very modern, startup-friendly (high limits), and scales well for fast-growing teams. They offer flat 1.5% cash back. Ramp is the best option if you just want to get one credit card for your startup and not worry about points.
Simple program, recently devalued: Brex Rewards
Brex is very modern, startup-friendly (high limits), and scales well for fast-growing teams. They offer lower earnings than other cards mentioned but their points are convertible to airline programs like Avianca and Singapore Airlines .
Unfortunately, we can no longer recommend starting with Brex because they recently decreased the value of their points by as much as 40% with no prior warning.
Start with these cards
Earn ~2% back on each dollar purchased
For your business
~2% flat rewards card
American Express Blue Business Plus — 2 Amex points ($50k / year)
Bank of America Business Advantage Unlimited Cash Rewards — 2.62% cash back (little complicated)
Capital One Spark (2% Cash Plus or 2x miles) — 2% cash back or 2 Capital One points
Chase Business Unlimited — 1.5 Chase points
For yourself
~2% flat rewards card
Bank of America Travel or Premium Rewards — 2.62% cash back (bit complicated)
Citi Double Cash — 2% cash back or 2 Citi ThankYou Points
Capital One Venture X — 2 Capital One points
Earns >2% in the categories you spend the most money
I typically won’t open one of these unless I spend >$10k / year in a category
For your business
Advertising (Facebook, Google, radio, etc)
American Express Business Gold — 4x Amex points
Chase Business Preferred — 3x Chase points
Shipping (UPS, FedEx, USPS, etc)
Chase Business Preferred — 3x Chase points
Airfare
American Express Business Platinum — 5x Amex points (booked directly with airline)
American Express Business Gold — 4x Amex points (booked directly with airline)
Chase Business Preferred — 3x Chase points
Hotels
Capital One Spark (2% Cash Plus or 2x miles) — 5% cash back or 5 Capital One points (booked on Capital One travel)
Chase Business Preferred — 3x Chase points
Gas stations
American Express Business Gold — 4x Amex points
Restaurants
American Express Business Gold — 4x Amex points
Office supply stores
Chase Business Cash — 5x cash back or Chase points
For yourself
Airfare
Chase Sapphire Reserve — 5x Chase points (booked through Chase travel portal)
Bank of America Premium Rewards — 3.5% cash back (bit complicated)
American Express Platinum — 5x (booked directly with airline)
Capital One Venture X — 5x Capital One points (booked on Capital One travel)
American Express Gold — 3x (booked directly with airline)
Citi Premier — 3x ThankYou Points
Hotels
Capital One Venture X — 10x Capital One points (booked on Capital One travel)
Chase Sapphire Reserve — 10x Chase points (booked through Chase travel portal)
American Express Platinum — 5x Amex points (booked on AmexTravel.com)
Citi Premier — 3x ThankYou Points
Restaurants
Chase Sapphire Preferred — 3x chase points
Chase Sapphire Reserve — 3x Chase points
American Express Gold — 4x Amex points
Bank of America Premium Rewards — 3.5% cash back (bit complicated)
Citi Premier — 3x ThankYou Points
Bilt Rewards — 3x Bilt points
Brex Cash — 4x Brex points
Supermarkets
Consider a specific airline’s or hotel’s credit card if you spend a lot of time or money with them
How to think about annual fees
The first year is almost always justified by the signup bonus
Reconsider if the card is right for you each year.
Whenever you get a card with an annual fee, set a reminder to reconsider the card in one year.
Once you’re charged the annual fee, you have about a month (varies by company) to close the card and get a refund.
Ask yourself:
- How many points did I earn with this card last year?
- Are there other benefits I like that only come with this card? (airport lounges, DoorDash credits, etc)
- Can I “product change” to a cheaper card? This lets you keep the account open and the credit limit available. It’s not great to constantly be closing and opening personal lines of credit so changing to a no-annual fee card just to keep the limit around can be worthwhile.
- Can you transfer the credit limit to another card you have at the same bank?
- It’s usually not possible to transfer credit between business and personal cards but be sure to research / ask.
Expert tip: always try and get retention bonuses
Even if you’re planning to keep the card, call the credit card company and say you’re thinking about canceling the card and ask for a retention bonus to keep you as a customer. Sometimes they’ll waive the annual fee, offer you a new bonus if you spend some money on the card in the next few months, or some combination.
Be sure to just say you’re thinking about cancelling because some companies won’t try to hold onto you as a customer and just cancel the card if you say you want to do that.
Turbocharging your points with signup bonuses
At some point, you should consider opening cards just to get a signup bonus.
Bonuses are typically structured in the form: spend $X,000 in Y months to get Z0,000 points
Before you do this:
- Make sure the bonus is worth your time. I don’t consider bonuses worth less than $750. You need to do some math to figure out what a card’s bonus is worth. Lots of people value points each month — I like Upgraded Points. In general, airline points are worth more than 1 cent while hotel points (except Hyatt) are worth a lot less.
- Make sure you can meet the minimum spend easily. The best bonuses are the ones you earn with a single transaction.
- Set a reminder to close the card after one year. Keeping a card open for only a few months might be seen as “gaming” and get your bonus “clawed back” and the credit card company might ban you from being their customer.
- Expert tip: when you call to cancel the card just say you’re thinking about canceling the card and ask for a retention bonus to keep you as a customer. This works best on cards that have annual fees.
- Set a reminder to repeat this on some cadence
I follow this strategy:
Open a new personal card every 6 months
Stay under 5/24
Open a new business card every 6 (possibly 3 months)
Remember you can generally get the same card for different businesses (even at the same time)
How to go/stay where you want for free
Earn Free Flights (my favorite)
While it’s often best to book tickets using points with an airline’s own miles you don’t have to earn these points with an airline-branded credit card. It’s often better to earn convertible points from banks like Chase or Amex that can be transferred to the airlines you want to fly.
Miles from convertible programs like Chase and Amex and typically transfer to their airline partners at a 1:1 rate and it’s often easier to earn a lot of miles from these programs than with the airlines directly.
Sometimes it can be better (cheaper, easier to get points) to book tickets by booking through an airline’s partners. These are typically whoever they are in an alliance (OneWorld, Star Alliance, Skyteam) with but some carriers (like Air Canada) forge partnerships with many interesting airlines outside their alliance.
The table below has a page for each of the major airlines that you can fly on with points. There are many ways to book each of these airlines with practically all major point currencies. It is also sometimes worth opening an airline’s own credit card for additional benefits or earnings.
Airline list
Earn Free Stays & Status with Hotels
Hotels are kind of the opposite of airlines. It’s often much better to earn points using a hotel branded card than to transfer points to the program.
Hotel transfer partners
Hyatt - Easiest to get great value; the only hotel program generally worth transferring to
Obscure and not covered by this guide
Choice Privilege
Accor
Transfer via Capital One
Aspirational Awards & How to Book Them
Fly the World’s Best Airlines in First / Business
Many of these awards can be difficult to book and require a flexible schedule.
Booking from markets with a lot of points-obsessed people (San Francisco) can add considerable difficulty. Consider flying out of a city close to yours that might have better availability.
Lufthansa First Class to Germany / Europe
Only available to book ~four weeks before departure but usually some availability. A great seat with incredibly consistent service. Try to route via and have a long layover in Frankfurt so you can experience the First Class Terminal (be sure to ask for a rubber duck!)
Cathay Pacific First Class to Hong Kong / Asia
Used to have strong availability but extremely gradually coming back post-COVID.
Be sure to visit The Wing lounge in Hong Kong.
ANA First Class to Japan & Asia
Very difficult to find. Two seats are nearly impossible. Try looking ~365 days out or less than a week before departure.
New product just launched on routes from Tokyo to London, NYC, San Francisco, Los Angeles, sometimes Chicago. Try to make a cash booking on ANA’s website and make sure the flight says “The Suite.”
Redeem (price low to high) via Virgin Atlantic (though recently devalued 💔) or Singapore Airlines. ANA also possible but requires a roundtrip (very difficult to find)
Singapore First Class (Suites) to Singapore (or NYC - Frankfurt, Germany)
Only on the Airbus A380. Possible to book two adjacent seats to make a double bed in the sky.
Only possible to redeem via Singapore Airlines
Emirates First Class to Dubai & Beyond
What most people think when they hear “First Class.” A380s have showers on the plane, some 777-300ER have floor-to-ceiling fully enclosed suites.
Always fairly expensive but best to redeem via Emirates or possibly Air Canada
Qatar Q-Suites Business Class (world’s best) to the Middle East & Beyond
Qatar Q-Suites offer a lot of different type of seats (privacy for solo travelers, a double bed for couples) but aren’t available on all Qatar flights.
Stay at the World’s Best Hotels
Americas
Europe
Middle East
Maldives / Bora Bora / Fiji
Overwater villa in the Maldives
Bora Bora
Asia
Vietnam / Thailand / Malaysia Beaches
Australia
When are credit card points not worth it
If you carry a balance and pay interest. Paying 20% annual interest cancels out your 2% rewards really fast :((
If you spend more than you otherwise would to meet a signup bonus or earn points. Earning 2% of an extra dollar you spend means you lose (for yourself or your company) the other 98%.
If you forget to cancel cards with super high annual fees. A $500 annual fee card you forget about “costs” the same as earning points on $25k / year of spending.
If you miss a payment, mess up your credit score, and make your mortgage payment when you buy a house go up.
A note on ownership of credit card rewards
You can draw the line in a few places. One popular line is credit risk.
If you have to personally guarantee your business’ card in order to get your company cards with benefits like extended warranties and price protection, you are at risk if your company can’t pay its credit card bills.
Many founders in this situation choose to keep the point perks on the credit cards they personally guarantee. This system of a company reimbursing expenses made on employee personal cards is prevalent and marketed as an employee perk in consulting, investment banking, and other industries where travel is frequent.
What to do if you can’t get approved for the cards you want
Step one: call the reconsideration line
Plead your case. If you applied for a business card, be sure to have information about your business’ activity and revenue available.
If you’re still denied you probably have one of these problems:
Problem 1: not enough credit history
Sign up for easier cards to get
Some cards like Petal will underwrite based on your bank account balance.
Other cards like Sable are geared specifically at new arrivals to the US.
Build a relationship with the issuer
Sometimes banks like to have an existing relationship before they will give you a credit card. I was personally twice by Chase before I opened a bank account at one of their branches. This is pretty annoying but many banks will pay you several hundred dollars for opening an account with them.
Problem 2: too many recent credit pulls
Consider cards from different issuers
Chase will automatically deny any application from someone who has opened more than five credit cards (business cards usually don’t count) in the last 24 months (5/24 rule). Other banks have similar rules.
Sometimes you have to wait 💔
Further reading
I learned about the world of credit cards from a few of my friends and a bunch of random websites.
FlyerTalk Forums
An aggressive community of road warriors that have the definitive answer to most questions. More popular hotels will have threads hundreds of posts long with photos and extensive reviews.
One Mile At a Time
The strongest general site today. Good mix of trip reviews, credit card programs, with some travel news too.
View From the Wing
Tangential to the points world — more for avgeeks / travel nerds like me :)
PointsGuy
Very mass market and basic these days but have a very strong archive of more advanced topics.
Disclaimer:
I’ve used my referral links to some of the above cards that I have. This means I will sometimes get some points when you sign up for these cards. If I’m aware of a better bonus than what you could get with my referral link I will use that link instead — even if it means I get no referral bonus.
I can only make so many referrals each year so once I reach my limits I’d love to include your referral links too! Preference will be for people who previously used my links to sign up for cards :)
All the things linked in this guide:
Credit card programs
American Express Membership RewardsBank of America Preferred Rewards Bilt RewardsBrex RewardsCapital One RewardsChase Ultimate RewardsCiti ThankYou PointsRampAirline alliances
Star AllianceOneWorldSkyTeamHotel programs
HyattHilton MarriottIHGWyndhamComprehensive list of all the credit cards we think are worth considering (ranked by signup bonus value)
Argomy can help you set up and run these systems
My company has a small team that advises on credit cards, elite status, and making travel arrangements (flights, cars, hotels).
You can email, call, text, or schedule a time to chat with us if you’d like some assistance. The first call is always free.
[email protected] || 412-436-9760 || calendly.com/spencerburleigh