10 Hills I’ll Die On About Money, Status, Careers, and ROI

Or: why I’ll spend thousands on a TV and then refuse to pay $20 extra for something stupid

I have some financial habits that probably look contradictory from the outside. I’ll spend stupid amounts of money on home theater equipment, but shop around to save $30 on shipping. I drive a performance car, but I’m perfectly happy buying things used, open-box, on Marketplace, or with a rebate. I’ll spend more for quality, but I have almost zero interest in paying extra because something has a prestigious logo on it.

I care about making more money, but I’m skeptical of the internet obsession with entrepreneurship and “escaping the 9-to-5.” I want financial independence, but I have no interest in spending the best decades of my life pretending I don’t like expensive hobbies. None of this feels contradictory to me. The common thread is simple:

I care about return, not price.

Money is a tool. So is time. So is attention. The goal isn’t to spend as little as possible. It’s to stop wasting those resources on things that don’t meaningfully improve your life. These are 10 hills I’ll die on.

Tesla is probably the best daily driver on the market

There are more exciting cars. There are more luxurious cars. There are better track cars, better-looking cars and cars with infinitely more prestige. But if I had to pick one car to actually live with every day, I still think Tesla is incredibly hard to beat. My 2022 Model 3 Performance is the perfect example.

It gives me stupid acceleration and AWD grip whenever I want them. It also has four doors, a good audio system, home charging, useful driver assistance, strong technology, and enough practicality to use every day without thinking about it.

Then I wake up the next morning with a charged car. That combination has messed with my perception of expensive cars. I’ve been around Ferraris, McLarens, R8s, GT3 RSs, Rolls-Royces, multiple generations of NSX, Hellcats and plenty of other legitimately special cars. I get the appeal. A Ferrari creates theater my Tesla never will. A GT3 RS is in another universe dynamically. A Rolls-Royce is an experience in craftsmanship.

But none of that automatically makes them better transportation. That distinction matters. If I’m spending $200,000 because something makes me feel something every time I open the garage, fine. That can be a perfectly valid purchase if I have the money. Just don’t tell me it is ten times the car because it costs ten times as much.

For actual daily use, the Model 3 Performance gets an absurd amount right. And buying one after somebody else has already eaten the worst depreciation makes the proposition even harder to beat.

Hill I’ll die on: The best car is not necessarily the car you’d put on a poster. It’s the one that gives you the most useful enjoyment per dollar and per mile.

Pay for performance you can use, not prestige you hope strangers will notice.

If your TV is your primary entertainment source, cheaping out on it is stupid

This one gets me because people will use a TV for thousands of hours, then call a few thousand dollars for a good one financially irresponsible. Meanwhile, they'll spend hundreds on dinner, drinks, concert tickets, sporting events, or a weekend trip without thinking twice. If you watch two hours of TV a day for five years, that’s about 3,650 hours of use.

A $3,000 TV works out to roughly 82 cents per hour. A $700 TV works out to about 19 cents per hour. So the actual premium for the $3,000 TV is roughly 63 cents for every hour you use it over those five years.

Paying more can be an incredible use of money when it buys a substantially larger screen and noticeably better HDR, black levels, motion, and brightness. The key is that you notice the improvement every day.

Especially if staying home is already one of your primary forms of entertainment. This logic is a big reason I’ve spent so much on home theater. Yes, my setup is objectively excessive. But I use it constantly. Movies. Shows. Gaming. Music. Friends over. Events. Random YouTube videos that absolutely did not need 98 inches of Mini-LED.

I get thousands of hours of enjoyment from the room. Compare that with someone buying a $4,000 designer bag that comes out of the closet twice a month primarily because other people recognize the logo. Which one is really the irresponsible purchase? The answer depends entirely on the person. That is the point. Hill I’ll die on: Spend disproportionately on things that disproportionately affect your life.

If your TV is the centerpiece of your entertainment, buy a damn good TV.

“Be your own boss” is wildly overrated

The internet has somehow turned having a normal job into evidence that you lost at capitalism. Everybody needs a side hustle. Everybody needs a business. Everybody needs passive income. Everybody needs to “escape the 9-to-5.” Why?

Entrepreneurship can be incredible. The upside is uncapped, ownership can create serious wealth, and building something of your own can be much more fulfilling than working inside a large company.

But the romanticized version leaves out something important:

You don't stop having a boss. You acquire a shitload of bosses.

Customers become your boss. Cash flow becomes your boss. Payroll becomes your boss. Suppliers become your boss. The bank becomes your boss. Algorithms become your boss. Deadlines become your boss. And when something breaks at 9 PM on Saturday, congratulations. The owner is available.

The financial risk is real too. Bureau of Labor Statistics establishment data consistently put five-year survival near half, while ten-year survival is closer to one-third. Those are establishment statistics, not a prediction that every new business has the same odds, but they are a useful counterweight to the internet's survivorship bias.

Income can also become dramatically less predictable. In the Federal Reserve's 2025 household survey, 58% of self-employed adults reported month-to-month income variability, and 22% said variable income had caused difficulty paying bills during the prior year.

That doesn't make entrepreneurship bad. It means the salaried employee with strong compensation, good benefits, remote flexibility, reasonable hours and investments growing quietly in the background isn't necessarily the sucker. They might have made the better deal. Personally, my ideal outcome isn't “own a business at all costs.”

It's maximum money, maximum optionality and minimum unnecessary bullshit. If entrepreneurship is the best vehicle for that, great. If a high-paying W-2 job, investments, and scalable side income get me there with less risk, I will take that route. I am not starting a business just to put CEO in my Instagram bio. Hill I’ll die on: Ownership is a tool, not an achievement by itself.

Paying to flex is one of the dumbest ways to spend money

There is a difference between buying something expensive because you love it and buying something expensive because you want strangers to know you can afford it. I completely understand the first. The second makes almost no sense to me. What exactly is the expected return? You impress people who care deeply about visible wealth.

Congratulations. You have now disproportionately attracted people who care deeply about visible wealth. That might be useful if you're selling a lifestyle for a living. For everyone else, I'm not convinced that's the demographic I want optimizing for me. Visible flexing also creates unnecessary information. Now strangers know you have money.

Acquaintances think you have money. Someone trying to sell you something thinks you have money. Someone asking you for money thinks you have money. Someone deciding whether a dispute is worth pursuing may think you have money. I'm not arguing that wearing a Rolex magically causes lawsuits or theft. I'm arguing that broadcasting assets to people who have absolutely no need to know about them has very little upside for most people.

And social media has somehow convinced everyone that wealth only counts if there's photographic evidence. No thanks. One of my favorite ways to put this is:

Why am I spending my money for the approval of people who neither contribute to my life nor share the consequences of my decisions?

They're not paying my mortgage. They're not funding my retirement. They're not buying my groceries. Their opinion has essentially no economic value. So why would I make economic decisions around it? Hill I’ll die on: Being wealthy is useful. Looking wealthy is often expensive. Those are not the same objective.

Prestige is one of the biggest markups on Earth

Take handbags. Imagine three bags:

• $50,000 Birkin-tier purchase
• $5,000 Louis Vuitton
• $500 Michael Kors

Are they exactly equivalent? Of course not. Materials differ. Construction differs. Design differs. Exclusivity differs. Resale can differ enormously. Collectibility is real. But all three are extraordinarily capable of completing the core engineering challenge of holding your phone, wallet and keys. Once you've crossed the threshold into a well-made product, every additional dollar increasingly buys something other than utility.

Brand history. Scarcity. Exclusivity. Craftsmanship. Status. Recognition. Those can all be legitimate things to buy. My issue is pretending they're performance.

If you genuinely adore Hermès craftsmanship, have enormous disposable income and get $50,000 worth of enjoyment from owning the bag, I'm not going to tell you you're wrong. The economics change completely if you're buying it because you hope everyone at dinner notices it. Now you're renting social approval. Fashion makes this particularly obvious because trends eventually move.

The logo that screams money today can scream “2019” tomorrow. The shoe becomes uncool. The silhouette changes. The hot brand gets oversaturated. Congratulations on paying the maximum possible price near peak hype. I would much rather buy something that is extremely well made, looks good to me, and lands before the diminishing-returns curve goes vertical.

The same applies to watches, sunglasses, clothes, luggage, furniture and plenty of cars. Hill I’ll die on: Premium quality can be worth paying for. Prestige for prestige's sake usually isn't.

Lab-grown diamonds make natural-diamond pricing look ridiculous for most buyers

Diamonds might be the cleanest example of my entire philosophy. Natural diamonds are remarkable geological objects: rare, ancient, and formed under extreme conditions deep within Earth. That history can carry real emotional value. But it does not answer the question I care about:

Why should I pay an enormous premium for geological origin when the thing I actually see can be equal or better?

GIA says laboratory-grown diamonds have the same crystal structure and nearly the same chemical, optical and physical properties as natural diamonds. To the eye, they can be indistinguishable, with sophisticated testing needed to reliably identify their origin.

So imagine the choice is something like: A smaller mined diamond with more inclusions for $50,000. Or a larger, cleaner lab-grown diamond for $5,000. I'm taking the lab diamond and keeping the other $45,000. Every time. Someone can tell me the natural one took billions of years to form. That's cool. So did a lot of rocks. The more defensible reason to choose natural is emotional value, geological rarity, provenance, collectibility or tradition.

Those are subjective benefits. What I reject is the idea that paying multiples more automatically gets you a functionally better diamond. It can actually force you down in size, color or clarity simply to preserve the word natural.

And the cultural importance of diamonds isn't independent of marketing. De Beers' famous “A Diamond Is Forever” campaign played a major role in cementing diamonds as symbols of permanent romantic commitment.

Again, brilliant marketing. I'm just not volunteering to subsidize it. Hill I’ll die on: If technology can give me the properties I care about for dramatically less money, “but nature made this one” isn't enough to open my wallet.

Frugal and financially intelligent are not synonyms

This is probably the most important Mr ROI distinction. Frugality asks:

How little can I spend?

ROI asks:

How much value am I receiving for what I spend?

Sometimes those produce the same answer. Sometimes they produce completely opposite answers. I can own a roughly $40,000 home theater and still think paying an unnecessary $30 shipping charge is stupid. That's completely rational to me. The theater provides thousands of hours of entertainment in one of my biggest hobbies. The shipping surcharge provides me absolutely nothing.

One is expensive. The other is waste. This is also why I like used products, open-box deals, cashback, rebates, warranties, Marketplace and buying last year's high-end model. I don't care about having paid full price. Actually, paying full price when I didn't need to almost annoys me. There is no trophy for being the person who gave the retailer the most money.

At the same time, I'm not buying garbage just because it's cheap. Cheap junk that breaks, irritates you, wastes your time and gets replaced repeatedly can be far more expensive than buying the right product once.

My ideal purchase lives somewhere around the point where performance has risen dramatically but the diminishing-returns curve hasn't gone completely stupid yet. Sometimes that's $100. Sometimes it's $10,000. Hill I’ll die on: The dollar amount tells you how expensive something is. It does not tell you whether it is wasteful.

FIRE should buy freedom, not require you to waste your youth

I want financial independence. I also like cars, home theater, technology, fitness equipment, travel, good food and having a nice place to live. Apparently those ideas are supposed to be incompatible. I disagree. There is a version of FIRE that feels like optimizing the scoreboard while forgetting why you're playing. Work for decades.

Minimize everything enjoyable. Watch the brokerage account go up. Eventually hit the magic number. Then, at some future age when your health, interests, relationships and responsibilities may be completely different, begin enjoying yourself. That isn't my goal. I absolutely believe in aggressive saving, investing early, controlling lifestyle inflation and avoiding high-interest debt.

But maximizing my bank balance isn't the same as maximizing my life. Some experiences have a window. I'll probably enjoy certain physical activities more while I'm young. I can use a performance car differently at 23 than I might at 73. A home gym improves my life now. The memories from a trip exist for decades. Money compounds.

So do experiences, skills, relationships and health. My strategy is therefore not deprivation. It's selectivity. Cut the 20 purchases you barely care about. Then buy the ridiculous thing you genuinely do care about without apologizing for it.

Hill I’ll die on: Financial independence should create a better life. If pursuing it makes your entire life worse for 30 years, something went wrong with the optimization.

Titles, promotions and traditional milestones are not automatically progress

Promotion. Management. Homeownership. Entrepreneurship. Luxury car. Marriage. Big house. Executive title. There are a lot of boxes society teaches us to check without asking whether the next box actually improves anything. Take careers.

If somebody offers me a promotion with 10% more money, substantially more stress, longer hours, worse flexibility and more political bullshit, I don't automatically see that as advancement. The title improved. Did my life? Maybe the better move is staying where I am. Maybe it's switching companies. Maybe it's building more technical skills.

Maybe it's taking a remote position that technically sounds less prestigious but gives me ten hours of my week back. The same applies to houses. Renting isn't automatically wasting money. Owning isn't automatically investing. A giant house isn't automatically better than a smaller house with exactly the garage, office, theater and privacy you actually wanted.

I have increasingly little patience for optimizing my life around the conventional sequence of what I'm “supposed” to want. Prestige is a terrible substitute for fit. Hill I’ll die on: Progress should be measured in money, freedom, capability, health, relationships and enjoyment. Not titles and checkboxes.

Fix the giant obvious thing before optimizing the last 2%

This might be the principle that ties everything together. People love tiny optimizations because they're interesting. The big fixes are usually boring. Fitness is the easiest example. People will spend $300 on supplements while sleeping five hours. Buy a recovery gadget while barely walking. Debate the perfect exercise variation while missing workouts.

Argue about nutrient timing while failing to eat enough protein. Finance works the same way. People hunt for the next stock while carrying 25% credit-card debt. Spend hours optimizing a 1% cashback difference while ignoring their career income. Save $4 on coffee while financing a $70,000 vehicle they can't comfortably afford. Home theater people will argue about cables while their speakers are positioned terribly.

Car people spend thousands shaving a few pounds while driving around on bad tires. Productivity people create a twelve-database Notion system to avoid doing the task. And yes, I'm guilty of this too. Optimization is fun. But optimization should happen in descending order of impact. I want the 50% improvement first. Then the 20%.

Then the 10%. Eventually I'll happily obsess over the 2%, because that's the kind of person I am. But only after the big stuff is handled. Hill I’ll die on: Don't major in the minors.

The Actual Point

These opinions can make me sound cheap in one conversation and financially irresponsible in another. I'll tell someone not to buy the designer bag and then recommend a $3,000 television. I'll question a $100,000 luxury car and then talk about spending thousands on giant subwoofers. I'll advocate FIRE and then spend money on something completely unnecessary.

I'll work a corporate job while telling people I care about financial freedom. It only looks inconsistent if the decision rule is:

Expensive = bad.

That's never been my rule. My rule is:

What am I actually getting in return?

Does it save time? Does it improve something I experience every day? Does it last? Does it increase my capability? Does it make me healthier? Does it make me money? Does it create a memory? Does it give me freedom? Do I genuinely love it? Or am I buying it because somebody convinced me I should want it? That last question eliminates a shocking amount of spending.

I don't want the cheapest life possible. I don't even necessarily want the wealthiest-looking life possible. I want a high-quality life with as little waste as possible. That means I'll spend aggressively where the return is obvious. I'll buy premium when premium actually buys something. I'll buy cheap when cheap solves the problem perfectly.

I'll buy used when the new-product premium is pointless. I'll ignore prestige when prestige is the product. I'll keep a salaried job if it's a better deal than owning a company. I'll buy the giant TV if I'm going to stare at it for 5,000 hours. And I absolutely refuse to spend money trying to impress people whose opinions have no meaningful effect on my life.

Price is not value. Prestige is not quality. Ownership is not freedom. Frugality is not financial intelligence. And expensive is not the same thing as wasteful.

The goal is not to spend less.

The goal is to get more.

That's Mr ROI.