The Advantage #20: Optimism, Iteration, and Spending on What You Actually Use

Thanks for tuning in to the twentieth issue of The Advantage. A short, weekly note where I share what I am working on, something worth watching, a lesson from history, and one practical edge you can try right away.

First, thank you to everyone who sent feedback over the last few weeks. I read all of it, and I am making some changes based on what you told me.

Starting this week, the Wednesday edition is getting shorter. From here on out, the weekly issue will be focused on two sections only: Worth Watching and Practical Edge. Quick to read, easy to act on, designed to fit into the middle of a busy week. What I Am Working On will move out of the weekly cadence and become its own standalone email that goes out whenever I have something real to share. That way you get the build updates when they actually happen, not on a forced schedule. The Lesson from History section is retiring for now. A few other ideas are in the works, but I want to get the core leaner before adding anything new.

The point is the same as always. Less filler. More signal. Hope you like the new shape.

Optimism and Iteration

This week's watch is a clip from Modern Wisdom with Chris Williamson and Naval Ravikant. About 11 minutes. Two ideas in it sit right on top of each other and they belong together: be an optimist, and iterate fast.

These two things only work as a pair. Optimism without iteration is wishful thinking. Iteration without optimism is grinding yourself into the ground for no reason. Put them together and you have the actual operating system for building anything good.

Naval frames it as being optimistic in the general and skeptical about the specific. Any one date, any one hire, any one product launch is probably not the answer. But something in here is going to work. So you investigate fast, cut your losses fast, and when you find the thing that compounds, you go all in.

I see this in every part of life. Relationships. Sports. Friends. Investments. Building Petfolk. The people I know who win are not the ones who picked right the first time. They are the ones who took more shots, killed bad bets earlier, and stayed optimistic enough to keep swinging.

Buy What You'll Use Every Day

A little over a year ago, I put a golf simulator in my gym. Full remodel. All the equipment. About $50,000 in. Plus or minus the cost of a car.

I hesitated for a long time on the cost. I was fortunate to be in a position where I could afford it, and I want to be clear that the test is not “spend more.” It is “spend deliberately.” You should always be thoughtful about money, especially on the big stuff. But once something passes that filter, the worst thing you can do is pull back on the things that actually bring you joy.

I pulled the trigger and went all in. I use it every single day. Usually for at least an hour. Friends come over and play rounds. My kids love to come down and we play putt putt & exploding cars. (The oldest is 6). And this winter when there was snow on the ground for 3 months straigh it kept me sane. It is the probably the best purchase I have ever made.

The lesson is not “buy a simulator.” The lesson is that we systematically misjudge where our money actually buys happiness. We pour cash into things that look good and sit unused. Watches in a drawer. A second car in the garage. The boat that goes out twice a summer. Meanwhile the things that show up in our lives every single day get underfunded.

The right question after “can I afford this?” Is “how often will I actually use it, and how much joy will it bring me when I do?”

Cornell's Tom Gilovich has spent two decades on this question. His research keeps landing in the same place. Experiential purchases produce more happiness than material ones because they build identity, foster social connection, and resist comparison. A watch invites comparison. A round of golf with friends does not.

Then there is hedonic adaptation. The brain habituates to material purchases fast. The new car becomes the normal car. The novelty fades and you need a bigger purchase to chase the same feeling. Experiences resist this because they are never identical twice.

The most useful finding for operators is this one. Well-being goes up more from frequent consumption of low-cost hedonic products than from infrequent consumption of expensive ones. Frequency wins. A simulator I use 365 days a year is closer to a daily experience than it is to a luxury purchase. That is the arbitrage.

Run every discretionary purchase through two filters before you buy. The first is the one you already know. Can you actually afford it without compromising the things that matter more. If the answer is no, the rest of this does not apply. Discipline on the big number is non-negotiable.

The second filter is the one most people skip. How often will you actually use it, and how much enjoyment will it produce when you do. Sticker price tells you almost nothing on its own. A $50,000 simulator used 350 days a year for five years works out to around $800 a month, around a car/boat payment, but the math is the smaller half of the story. The bigger half is the hours of real enjoyment, the friends who keep coming over, the time hitting with my kids and getting them to love the game. That is the part that does not show up on a spreadsheet and it is the part that compounds.

The trap is the opposite kind of purchase. The watch you barely think about. The car that mostly sits. The boat that goes out twice a summer. They look great on the surface, but the joy fades quickly and they invite the wrong kind of comparison. Status purchases are about the audience. Passion purchases are about the use. The second category compounds. The first does not.

The honest test is simple. Would you still want it if no one ever saw it. If yes, and you can afford it, do not hesitate. The mistake I made was waiting. The simulator paid for itself in joy inside the first six months. Every day since has been free.

Thanks for reading.

Mike Wystrach

Founder · Operator · Investor

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