I have 12 credit cards between my wife (P2) and me. Two of those also have paid authorized users. That is more than I would recommend to almost anyone reading this.

The reason is pretty simple. I am a bit of a points-and-miles nerd. I enjoy traveling, travel planning and I always have to be working on my next trip. I am constantly trying to learn more about how to get better value on the kind of travel we like. I am out to find the best flights, hotels, activities and destinations that I can get my P2 or kids excited about.

Along the way I love the challenge of figuring out obscure transfer partners, testing different earning strategies and seeing whether the edge cases actually work. For me, this is partly financial optimization and partly a hobby.

That distinction matters.

It started a long time ago

I can probably trace the beginning back to 2002. I had just started working as an industrial engineer supporting sales, which meant I was traveling quite a bit. I remember sitting in a pretty lousy airport during a long layover, directly across from an airline lounge. I knew what was probably behind those doors: a quieter place to sit, something to eat, decent internet, a complimentary drink. And I had heard that there were credit cards that could get you inside. That curiosity never really left.

Years later, around 2012, I took a remote job that had me flying back and forth to Dulles near company headquarters and traveling around the country again. This time I knew exactly what I wanted.

I signed up for the United Club card because lounge access had real value to me. I was spending hours in airports and I wanted to be comfortable, have good internet and a free drink. Priority Pass was occasionally useful, but not at the airports where I spent the most time, particularly Dulles and Chicago. That was not about collecting cards. It solved a specific problem.

Then I went much deeper

Once I got back into frequent travel, I started paying a lot more attention to points. And once my analytical side got involved, things escalated pretty quickly. Today I have cards across Chase, Bilt, Capital One, American Express, Alaska, Southwest and United.

Some have been excellent. Some I probably never should have opened. And some are there because I wanted to test an idea and see whether it really worked.

That is one of the reasons this newsletter exists. You get to benefit from both sides of my experience.

One experiment that worked extremely well

A good example is my current Bilt and Alaska Atmos setup. I knew we were going to be flying regularly to Miami and Charlotte because our college-aged daughters are there. Those are strong American Airlines markets, and I knew Alaska’s points could be valuable because of its partner access and award pricing. So I had a redemption opportunity before I built the earning strategy.

The basic idea was to earn points through Bilt, transfer them to Alaska Atmos, and use Alaska’s partnership with American Airlines to book flights we already needed. Then, Bilt as part of its 2.0 restructuring, introduced its new Palladium card. Bilt was getting plenty of criticism during the transition, but I thought the earning structure fit what I was trying to accomplish, so I went in at the highest level. That has worked much better than I expected.

Bilt Palladium can earn an effective 3X on qualifying everyday spend when I activate the Point Accelerator. I have since used those points for short-haul trips where I have been getting more than 9% yield on the underlying spend.

I regularly book flights to Miami and Charlotte for the equivalent of $67.50. So I am saving around $300 a flight: my ticket is fully refundable, I get the best economy+ seat, plus I am on the upgrade list.

The same broader Alaska strategy also helped my wife and me book two lie-flat seats to Buenos Aires for 75,000 points total after using a 25,000-point Companion Award that came with my Atmos Summit Card. With this card I also earned a 100,000-point Companion Award after $60,000 in spend. That spend which also earns status points helped me reach oneworld Gold.

I have Alaska Atmos Gold status. I have never flown on an Alaska airplane. That probably tells you everything you need to know about how deep I am willing to go down the rabbit hole.

You probably should not do what I do

Here is the important part. I spend somewhere between 10 and 20 hours a week reading, researching, planning trips and figuring this stuff out, and I enjoy it. That time is not producing an economic return anywhere close to what I would demand from paid work. But that is what makes it a hobby.

Most business owners do not need another side job or hobby. If you are already spending $20,000, $50,000 or $100,000 a month, there is plenty of value sitting in that spend without turning your wallet into a research project.

Most people need a core, not a collection

When I’m helping someone put together a card strategy, I start with how they actually travel and spend. Where will their points deliver the best return? Only then do we decide which cards belong in their wallet. Then when we build the wallet, I would usually start with a primary transferable-points ecosystem.

Take Chase as a simple example. You might have one card that earns well on everyday business spend, another that earns more in a specific category like advertising, and a higher-end card that provides travel benefits and lets you move the points out to airline or hotel partners. Those cards are doing different jobs, but they are all feeding the same pool of points.

If a specialty card solves a real problem, add it, but remain selective. When I was flying United constantly, a United lounge card made sense because it gave me something I actually needed. A specialty card should unlock specific value. It should not be another card you added because someone told you the signup bonus was good or you fly that airline a lot.

This is the real distinction between my setup and what I would recommend to most readers.

You can get most of the value without most of the complexity

Over the last 12 months, I have generated roughly $25,000 in realistic travel value from the way I use points. I also spend far more time on this than I would ever recommend to a friend.

You can earn efficiently. You can redeem for travel you were already going to buy. You can add a few benefits that make your trips easier. And you can do all of that without spending hours a week reading award charts.

That is what I want Yield On Spend to help with. I will keep testing the weird stuff. You get most of the return without the complexity.