What’s in my wallet: Optimizing *every* dollar — July 2023 (Maximizing Credit Card Rewards)

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I have a ton of credit cards so I will jump into it quickly but wanted to explain my rewards strategy first. My goal is to optimize every dollar I’m spending to get reward points through credit cards. Often, I wait for bigger purchases to happen and pay through gift cards vs. making impulse buys or I wait for credit card offers that will give me extra points. If you’re interested in learning more, follow for more!

See all my credit cards picks here

Here’s my current overview table for point usage for reference on how I’m optimizing spending.

For the Bilt Mastercard point bonuses, see Wells Fargo terms here. Use the card 5 times each statement period to earn points.

Category	Card	Rewards
Rent	Bilt Mastercard®	1x
Groceries	Citi Custom Cash℠ Card	5x
Grocery stores (abroad)	Citi Premier® Card	3x
Transportation	Chase Sapphire Reserve®	3x
Lyft rides + CitiBike	Chase Sapphire Reserve®	10x
Lyft rides + CitiBike	Bilt Mastercard	2x extra
Uber (abroad)	Chase Freedom Flex℠ (UR)	5x
Airbnb	Chase Freedom Flex℠	5x (amazon gift card)
Airbnb	Chase Sapphire Reserve®	3x
Travel (Hotels)	Chase Sapphire Reserve®	3x or 10x through UR
Dining / Restaurants	Bilt Mastercard	3x - 11x
Food delivery	Chase Sapphire Reserve®	3x
Fitness Classes	Bilt Mastercard®	2x
Internet	Bilt Mastercard®	2x
Clothing	Chase Freedom Unlimited®	1.5x - 10x
Amazon	Amazon Prime Visa	5x
Flights (with airline)	The Platinum Card® from American Express	5x
Personal Care	Chase Freedom Unlimited®	3x - 10x
Pharmacies	Chase Freedom Unlimited®	3x
Subscriptions	Bilt Mastercard®	2x
Digital Entertainment	The Platinum Card® from American Express	$20 free monthly
Business Expenses	Chase Ink Business Unlimited	1.5x
Everything else	Chase Freedom Unlimited®	1.5x

Basic expenses

When it comes to credit card rewards, basic expenses – those recurring costs we all have, like groceries, utilities, internet, and subscriptions – present a fantastic opportunity to earn significant points. This is because these expenses are consistent, regular, and, most importantly, inevitable. If we're going to spend money on these items anyway, why not optimize them for maximum rewards?

That's exactly what my strategy for basic expenses aims to do. Rather than just paying for these costs outright, I channel them through specific credit cards that offer the best rewards for each type of expenditure. This way, every dollar I spend on these basic necessities is also a step towards earning valuable reward points.

But choosing the right card for each expense isn't random. It involves a keen understanding of the rewards structure of each card, coupled with an awareness of my spending habits. This strategy allows me to turn the mundane task of paying for basic expenses into a rewarding experience. Let's delve into how I optimize my card usage for these everyday expenses.

Chase Freedom Unlimited® 

The Chase Freedom Unlimited® is the basic card in my wallet's arsenal. For any basic expense, this card comes out of my wallet with impressive frequency. It's simple: for every dollar I spend, I earn 1.5 points, a solid return on any purchase. It's a flat-rate card, which means there's no need to track specific spending categories, making it ideal for my broad, everyday purchases.

But the real magic begins when I transfer these points to my Chase Sapphire Reserve® card. Due to Chase's reward structure, each point's value increases when used for travel through the Chase Ultimate Rewards portal, allowing me to extract maximum value from every dollar spent.

To further optimize my points earning, I often use Chase's 'Earn Bonus Points' portal for higher point values on select purchases. One of my regular buys is skincare products. Before I purchase, I always check the portal because it often provides bonus point deals with certain retailers. For example, Dermstore is currently offering 6 points per dollar, while Sephora offers a whopping 10 points per dollar. I'm not only getting the products I love, but also maximizing my rewards points with each purchase.

Chase Ink Business Unlimited®

As someone who juggles over 10 side hustles, it's crucial to keep my business expenses separate from personal ones. That's why I've added the Chase Ink Business Unlimited® card to my lineup. The card's generous intro offer was a fantastic incentive – I received $750 cash back after spending $4000 on the card, a great boost to my bottom line.

Much like the Chase Freedom Unlimited®, this card also provides 1.5 points per dollar on all purchases, making it the perfect companion for my business expenses. Whether it's buying supplies for a project, investing in new software, or covering travel costs for a meeting, every dollar spent works harder for me.

Moreover, having this separate business card helps to streamline my finances. Each expense is clearly itemized, making tax season significantly less stressful. In essence, the Business Ink Unlimited not only earns me rewards but also contributes to my overall financial organization. The dual benefits of this card make it a vital tool for managing and optimizing my side hustles.

Special cards

Bilt Mastercard®

My Bilt Mastercard® plays a crucial role in optimizing my financial strategy, especially when it comes to my most substantial monthly expense: rent. For each dollar I spend on rent, I earn 1 point, transforming what is typically a significant outgoing into a reliable source of rewards points every month.

But the perks of the Bilt Mastercard® extend beyond just rent payments. It offers an enticing rate of 3 points per dollar spent on dining. From a casual brunch to an elaborate dinner date, every meal becomes a point-earning opportunity.  

I have other cards that allow me to earn 3 points per dollar on dining but I’m using Bilt for most of those expenses because of it’s attractive travel partners (such as American Airlines).

One fantastic feature of this card is its bonus points on recurring purchases made on rent day. On this day, these purchases earn 2 points per dollar, doubling the usual rate. This incentivizes me to synchronize certain expenses with my rent payment, maximizing my points.

This bonus point structure also applies to fitness-related expenses like pilates classes, tennis court reservations, and more. If I make these payments on rent day, I earn 2 points per dollar, turning my fitness routine into an additional rewards source.

The same strategy applies to my WiFi bill. By paying it on the same day as my rent, I get to earn 2 points per dollar. It's a small adjustment to my bill payment schedule that can lead to considerably more rewards over time.

See terms for point bonuses and annual fee here: Wells Fargo terms

5% cards

The next set of cards in my wallet are those that fall into the 5% category, and they are absolute powerhouses when it comes to optimizing my rewards strategy. These cards offer a whopping 5 points per dollar spent in their respective categories, which change periodically (often quarterly). This might seem complicated, but with a bit of planning, it's an exceptional way to maximize the points I earn on every dollar I spend.

The key to making the most of these 5% category cards lies in being strategic about when and where I use them. Every few months, I take a moment to check which categories are currently offering the 5% rewards rate, then plan my spending accordingly. For instance, if groceries are a 5% category in one quarter, I'll use that card for all my supermarket shopping during that period.

While this does require some attention to detail and flexibility, the rewards are undeniable. I've found that with a little bit of foresight and a willingness to switch up my card usage based on the rotating categories, I can significantly boost my rewards earnings. With these 5% category cards, every purchase is not just a transaction but an opportunity to earn more.

Chase Freedom Flex℠

The Chase Freedom Flex℠ card adds a dynamic layer to my wallet with its rotating category rewards. Chase defines these categories, which shift every quarter, ensuring a diverse range of opportunities to earn a substantial 5 points per dollar.

What's particularly advantageous about the Freedom Flex is that at least once a year, one of these rotating categories includes Amazon. As an ardent Amazon shopper, this gives me a significant boost to my points earning potential. But I don't just limit myself to shopping for everyday items during this period.

An interesting strategy I employ is to buy Airbnb gift cards on Amazon when it's part of the 5% category. This way, I'm essentially earning 5 points per dollar on future travel expenses. It's like having a mini-vacation fund that grows each time I make a purchase.

The Chase Freedom Flex℠ card, with its ever-changing categories, keeps my rewards strategy dynamic and flexible. By staying aware of the current 5% categories and planning my purchases accordingly, I am able to consistently maximize my points earnings. It's the perfect example of how a little bit of strategy can translate into a lot of rewards.

Citi Custom Cash℠ Card

My Citi Custom Cash℠ Card card is another significant player in my 5% rewards category. It has an ingenious feature where it automatically offers 5% on my biggest spending category each billing cycle. It's like having a card that intelligently adapts to my spending habits, ensuring I consistently earn the highest possible points.

One area where I frequently use the Citi Custom Cash℠ Card is for groceries. Given that groceries tend to be a significant part of most people's monthly expenses, I find this is a clever way to convert everyday spending into a consistent stream of points.

Where this card really shines is in combination with the Citi Premier® Card. The points I earn with the Citi Custom Cash℠ Card can be transferred to the Premier card, allowing me to use those points with Citi's travel partners. This means that every trip to the grocery store not only feeds me for the week, but also contributes towards future travel plans.

By using the Citi Custom Cash℠ Card card, I've effectively turned a significant part of my regular spending into a means of constantly earning and accumulating rewards points. And with its compatibility with the Citi Premier® Card, those points become an integral part of making my travel dreams a reality.

Amazon Prime Visa: 5% on Amazon.com & Whole foods

The Amazon Prime Visa card holds a special place in my wallet, and for a good reason. It offers a staggering 5% back on purchases made at Amazon.com and Whole Foods, making it a significant player in my rewards strategy.

Given the wide range of products and services available on Amazon, from household essentials to tech gadgets, this 5% back feature allows me to maximize my rewards on an incredibly diverse set of purchases. And since I shop at Whole Foods for groceries, the 5% back applies there as well, helping me earn rewards points on every shopping trip.

The one drawback of the Amazon Prime Visa is that I can't transfer points to travel partners. However, I view this as a minor concession when compared to the overall benefits of the card. The points I earn from my Amazon.com and Whole Foods purchases can still be redeemed in a multitude of ways, such as statement credits or gift cards, making the Amazon Prime Visa a rewarding choice for my everyday purchases.

Travel cards

As a frequent traveler for both personal and business reasons, having the right travel credit cards in my wallet is crucial. These cards not only help manage my travel expenses but also reward me for every dollar I spend, effectively turning my journeys into opportunities for earning points.

The beauty of travel credit cards lies in their tailored rewards programs. Whether I'm booking flights, hotels, or using ride-sharing services, I'm always earning a considerable number of points on these expenses. But the perks don't stop there. Many of these cards also offer benefits like free checked bags, airport lounge access, travel insurance, and more, adding comfort and convenience to my travel experiences.

While each travel card has its strengths and weaknesses, using them strategically based on my travel habits and preferences allows me to maximize my rewards. These cards are not just about managing travel expenses; they are about transforming my travels into rewarding experiences. Let's dive into the specifics of the travel cards I use and how I optimize them.

Chase Sapphire Reserve®

The Chase Sapphire Reserve® holds a top spot in my travel card line-up. I use it for most travel-related purchases due to its robust rewards system. For instance, it offers an impressive 10 points per dollar spent on Lyft rides, turning each trip into a point-earning journey.

One of the standout features of the Chase Sapphire Reserve® is its $300 annual travel credit. This credit automatically applies to a wide range of travel expenses, effectively reducing my out-of-pocket costs on everything from flights and hotels to tolls and parking fees.

But where this card truly excels is its travel portal. It allows me to combine points from all my Chase cards and redeem them for travel. With this feature, I can maximize my rewards by transferring points from my Chase Freedom Unlimited® or Chase Ink Business Unlimited® cards to the Chase Sapphire Reserve®, effectively increasing their value when used for travel.

By using the Chase Sapphire Reserve® for my travel-related expenses, I not only earn significant points but also enjoy substantial travel credits and the ability to maximize rewards from my other Chase cards. It's a comprehensive travel companion that adds value to every journey.

The Platinum Card® from American Express

The Platinum Card® from American Express is another critical component of my travel rewards strategy. I initially signed up for this card due to an enticing targeted offer of 150,000 bonus points. The allure of such a generous sign-up bonus was too good to pass up.

But what has made me keep the card is its excellent value proposition. By using it wisely in conjunction with a corporate Amex card, I've found that the card essentially pays for itself. The benefits it offers outweigh the annual fee, making it an incredibly cost-effective choice in my travel rewards strategy.

One of the standout features of the Platinum Card® from American Express is its comprehensive insurance coverage. From trip cancellation and interruption protection to car rental loss and damage insurance, it provides peace of mind on my journeys.

But the icing on the cake is the remarkable rewards rate of 5x points on flights booked directly with airlines. This feature turns every flight into a high-earning rewards opportunity, allowing me to accumulate significant points for my travel adventures.

The Platinum Card® from American Express, with its generous sign-up bonus, cost-effective benefits, extensive insurance coverage, and superb rewards rate, is a fantastic addition to my travel arsenal. It has proven to be an invaluable tool in my quest to optimize every dollar I spend on travel.

Citi Premier® Card: 

The Citi Premier® Card is a cornerstone in my travel rewards strategy, mainly due to its point transfer feature. This card allows me to transfer points from my Citi Double Cash card to travel partners, effectively turning my everyday spending into travel rewards. It's a seamless way of enhancing the value of my rewards by linking two distinct cards.

The Citi Premier® Card also came with a high initial sign-up bonus, which gave my points balance a considerable boost right from the start. It's an example of how one strategic decision - choosing a card with a generous sign-up bonus - can yield significant rewards.

Another feature I appreciate is the $100 hotel credit. It's a welcome benefit that reduces the cost of my accommodation expenses on select hotel stays.

But what makes the Citi Premier® Card particularly valuable for me is its utility during overseas travel. It doesn't charge foreign transaction fees, making it a cost-effective choice for international use. Plus, it continues to offer a rewarding rate of 3x points per dollar spent at grocery stores abroad. This means I can enjoy local cuisine and experience new cultures, all while earning points.

In essence, the Citi Premier® Card is an exceptional travel companion, rewarding me at home, abroad, and in between. It seamlessly connects my spending across multiple cards, maximizes my travel rewards, and saves me money on both accommodation and foreign transactions. It's an essential tool in my pursuit of optimizing every dollar I spend.

Maximizing rewards through credit cards is a strategy that can transform everyday spending into opportunities for savings, travel, and more. My approach revolves around optimizing every dollar spent and focusing on cards that offer the best rewards for my spending habits.

For basic and business expenses, I use the Chase Freedom Unlimited® and Chase Ink Business Unlimited® , respectively. Both cards provide a reliable 1.5 points per dollar, and with the ability to transfer points to my Chase Sapphire Reserve® card, I can further maximize their value.

My strategy involves targeted usage of cards offering 5% rewards like the Chase Freedom Flex℠ and Citi Custom Cash℠ Card for specific categories like Amazon and groceries. The Amazon Prime Visa boosts this further with a 5% back on Amazon.com and Whole Foods purchases.

For travel, the Chase Sapphire Reserve®, Platinum Card® from American Express, and Citi Premier® Card are key players. Each card provides unique travel benefits and rewards, with the Chase Sapphire Reserve® allowing me to combine points from all my Chase cards, the Platinum Card® from American Express offering comprehensive insurance coverage, and the Citi Premier® Card acting as a link for transferring points from my other Citi cards.

In essence, the idea is to let my spending habits dictate the choice of card, enabling me to gain the maximum points for each dollar spent. It's not just about owning multiple credit cards but rather about the strategic utilization of each one, ensuring every dollar spent gets me closer to my rewards goals. Whether it's travel, shopping, or everyday expenses, every purchase is a point-earning opportunity.

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