Vol. 5, Issue 1: The Third Zero

How Everything Got Worse (On Purpose) and What We Do About It

Everyone I know went to CES a couple of weeks ago*

*Well not everyone, but basically everyone. And my favorite comment about CES ever came from my sister who said “I love it when we all go to Vegas to see the same people we see in New York while we eat at the same restaurants we eat at in New York

And while we were at CES, we all met. And ate. And gambled. And while I was standing and chatting with a friend at the roulette table, I watched #5 hit and a couple of guys who I didn’t know win over $1000 each. I’m a sporting guy and I like when the house loses and people win, so I cheered for them. But while I was cheering, I noticed something.

There was a third zero.*

*If you’re not familiar, there’s a variety of ways to bet on roulette. You can bet the colors, red or black. You can bet even or odd. You can bet groups of numbers. Or you can bet the numbers themselves. But in order to win on the zeroes, you have to bet the zeros. They’re green, so they fall outside of the red/black construct of the game. They’re effectively winning house bets.

So I did some quick research. And as it turns out, at some point in the last few years, many casinos added a third green pocket to the roulette wheel. Now, we all know that the games are tilted to the house. That’s not a surprise. But there’s this social contract that we have the casinos: we come and gamble away some money at reasonable odds - as the payout gets bigger, the odds get longer - and they provide free drinks and sometimes a voucher for the buffet if you win or lose enough money. That’s a fair trade.

But something’s happened over the last few years: auto-shufflers bring cards back in to play more quickly, blackjack pays out at 6 to 5 instead of 3 to 2, progressive sucker bets pay out at way less than the actual odds of hitting them. All of these changes are changing that social contract. They all have one thing in common: they shift the odds further toward the house.

Stated more plainly: that third zero gives away the whole game.

Because this isn’t just about Vegas. Or casinos. Or gambling. It’s about America at large in its late stage of enshittification: everything getting marginally worse and optimized past the point of enjoyment. And unless we decide to do something, the people responsible will keep adding zeros to everything we touch.

If you’re not familiar with the term, enshittification was coined a Canadian journalist and author named Cory Doctorow, who used it to describe how platforms tend to degrade due to greed. First, they coddle users. Then they squeeze them. Then they collapse under the weight of their own greed.

But what started in tech has spread like contagion into nearly every corner of modern life: travel, retail, entertainment, housing, even how we buy a goddamn cup of coffee.*

*Here is a perfect example of non-Internet based enshittification: remember how you used to be able to get a cup of coffee outside of your house for $1 and it was pretty good? Now it’s $4.50 for the same size at Starbucks for empirically worse coffee and you have to wait 15 minutes to get it and the place has lines out the door

The common thread isn’t technology. It’s the mindset of late stage capitalism.

A philosophy that sees customers not as humans or long-term relationships to be nurtured, but as short-term yield opportunities. A belief that if something is working, the correct response is to make it just a little more profitable, forever and ever until there’s either no more money or no more people.

The third zero is emblematic. The house was already winning. They just couldn’t help themselves from trying to win just a little more.

You see the same thinking everywhere. Google had the cleanest, most beloved interface in the world. People happily used it every day. And yet, someone still decided the top of the page needed more ads, more AI answers, more paid placement masquerading as “sponsored links”. Not because users demanded it, asked for it or even thought about it, but because the entire system demanded growth.*

*It’s truly stunning how “Don’t be evil” turned into “Sorry we sold all your personal data to Taco Bell so they could sell a couple more Crunchwrap supremes. Maybe if you weren’t such a fat ass, it wouldn’t have worked”

The product didn’t fail. Restraint did. And the roulette story sticks because it’s such a simple, clean example.

The player remembers losing slowly. The rhythm of the game. The social energy. The that implicit contract that I described: “Yes, the house wins but you’ll have fun doing it. Maybe you’ll get drunk”

Later, they come back and realizes something subtle has changed. The game feels adversarial now. The casino logic is easy to understand: more revenue per minute. Faster churn. Higher yield.

But in a lot of cases the player’s* logic is just as clear: “Yeah, sure, but I’m never coming back.” Or “I’m not coming back as often as I would have.” Or “I’ll just spend my money somewhere else that’s just as enjoyable”

*Assuming they don’t have a serious gambling problem. If you live in NY and think you have a problem, call (877) 846-7369

That’s enshittification in a nutshell. Confusing extraction with strategy.

People don’t mind losing money when they know the rules. They mind feeling tricked. They mind when the system starts to feel predatory instead of playful. Once that trust breaks, the relationship is over.

You see this exact dynamic in ad tech. Buyers don’t mind fees. They mind fees that feel hidden, arbitrary, or untethered from real value creation. When simple take-rate models turn into opaque product bundles and black boxes, the question stops being “Is this effective?” and becomes “Who’s stealing what?”*

*Or in the immortal words of Aretha Franklin “Who’s zooming who?” (or more grammatically correctly, “who’s zooming whom?”. Who, the object of the sentence, zooming whom, the subject

The house was already winning. Someone still wanted to add another zero.

Enshittification shows up differently depending on where you look, but the pattern is the same.

Movies and music feel increasingly beaten to death. Endless sequels*. Music optimized for viral clips instead of emotional resonance. Surprise has been replaced by safety, and safety has been optimized into boredom.

*Since Tobey McGuire’s Spider-Man in 2002, there’s been him, Andrew Garfield and Tom Holland, plus the animated ones. 4 reboots in less than 25 years.

Shopping used to feel like a great convenience. Now it feels like a scavenger hunt with a guy on meth. Amazon went from “you’ll get the best version of this in 48 hours” to “pick one of these 74 indistinguishable products and pray that it’s not a piece of shit.”

Housing and work have followed the same path. Finding a place to live became a financial instrument of sub-prime loans, predatory rates and forced shortage. Jobs became a set of policies designed to protect companies from employees rather than empower them. An entire generation learned (correctly) that loyalty is a one-way street.

Concert tickets have been industrialized*. The show itself feels like a curated retail experience.

*Somehow it felt more fair when I went to the small video store in my town, got a bracelet with a number for a lottery, waited in line, worked with an employee tapping into a mainframe who then printed out your tickets on the spot and handed them to you when you paid

And then there’s everyday life, which seems to carry the same ambient hostility.

And let’s not look past ad tech, which deserves its own footnote here. Programmatic made buying easier. Then we strangled it with fee layers, supply-path gymnastics, arbitrage, and endless “value-added” products that mostly add cost, latency, and confusion. What started as simplification metastasized into complexity—because complexity is where margin hides.

Why does everything get worse? It’s not a mystery. It’s math.

Incentives drive behavior, and our incentives reward “more” at all costs. Corporations are trained to optimize KPIs, not experiences, and those KPIs are almost always profit motivated. Public companies prioritize the next earnings call over customer satisfaction. Leaders who find a way to squeeze another two percent of ARPU get promoted.

Enshittification isn’t a bug; it’s a feature. It’s the logical end state of a system where enough is never enough.

In ad tech, this shows up as an arms race of non-innovation innovation: new products that sound sophisticated, promise differentiation, and quietly extract a little more margin while delivering marginal, if any, incremental value.

You feel it in the tiny questions that now accompany daily life: Do I need to read Yelp reviews for a sandwich? Will this ticket link even work? Is this product real or a knockoff with better SEO?

It’s fucking exhausting. And no one wants to live like that.

So how do we reclaim a decent experience? This doesn’t require utopia. It requires agency.

Spend deliberately. Reward the businesses that still care. Stop tolerating places that treat customers like dollar signs.*

*Watch Buy Now on Netflix. It changed my perspective

Walk away from broken systems. You don’t have to play the 000 table. You don’t have to stay on platforms that treat you like a trapped audience. In ad tech terms, not every impression is worth bidding on.

Rebuild community at a human scale. Find the coffee shop, bookstore, or restaurant that actually remembers your name. Those places become comfort in a world that increasingly feels gross and disconnected.

Make your own joy. Host dinners. Travel intentionally. Take back small pieces of your life from the algorithm.

And yes, push for accountability. Basic fairness. Transparency. Guardrails that reward long-term thinking. The things that used to be table stakes for doing good business.

Enshittification has one fatal flaw: it only works if we keep playing.

If we start demanding better, not necessarily loudly, but consistently, the people designing our systems might finally remember that joy, not extraction, was always the real long-term value.

The house wins when we accept the rules without question. It loses when we remember that enjoyment was always the real long-term value.

And that’s a bet still worth making.

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OK, you guys, I’m back with the first installment of my 5th (!) year writing this thing.

As always, there’s a lot of things brewing and we’ll see what pans out, but for sure:

• Season 2 of Leadership In will start recording this winter

• JPEG Consulting will be in NYC in February and March and at Possible in April (will you?)