The Enshittification of America

Private equity didn’t build anything. It bought things people needed, borrowed against them, extracted the value, and left the debt behind. Then it moved on to the next one.

The Enshittification of America documents how that process dismantled twelve industries over four decades. Airlines that used to compete on service now compete on who can charge more for a carry-on. Hospitals absorbed by investment firms that never treated a patient now deny care to hit quarterly targets. Newspapers that held local governments accountable were gutted for their real estate and their printing presses. Retail chains that employed millions were loaded with debt they didn’t take on and bankrupted for the benefit of the people who loaded it. Restaurants, gyms, veterinary clinics, pharmacies, auto repair, housing. The pattern is the same in every industry: buy the thing people depend on, extract everything that can be extracted, and exit before the collapse.

This book names the mechanism, names the firms, and names the specific legislative and regulatory changes that made it all legal. It follows the money from the boardroom to the bankruptcy filing. It documents what was lost and what it cost the people who depended on these industries to get through their lives.

The last section documents the businesses and communities that held, and what the resistance to extraction actually looks like in practice.

Part of the Enemies of You series — seven books documenting the forces operating against you from the inside out. Each book stands alone. Together they form a single argument about the forces trying to control and enslave you for their own purposes.

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Look Inside

Preface

Why This Book Exists

I never set out to write a book about the decline of American business. I was perfectly happy ghostwriting memoirs and helping executives tell their success stories. But after twenty years managing technology at Trader Joe’s and then a decade listening to business leaders share their real stories, I started noticing patterns that kept me awake at night.

The same private equity playbook destroying one industry after another. The same optimization algorithms that could improve customer service getting repurposed to maximize fee extraction. The same executives who built great businesses explaining how they were pressured to dismantle what made those businesses great.

I watched companies I’d shopped at my whole life turn into hollow shells of themselves. Airlines that once made flying feel special now treat passengers like cattle. Department stores that anchored communities became real estate plays. Local newspapers that held mayors accountable got strip-mined by hedge funds that wouldn’t know journalism if it sued them for libel.

The turning point came during a client conversation in 2023. A Fortune 50 executive was explaining how his company had optimized customer interactions by replacing human service representatives with chatbots designed to frustrate callers into giving up. He said it with the detached professionalism of someone describing weather patterns. No malice, no awareness of what he was describing. Just systems working exactly as designed.

That’s when I realized we weren’t just witnessing random business failures. We were watching the systematic transformation of American commerce from a system designed to serve customers into one designed to extract maximum value from them. This isn’t a book about individual bad actors. It’s about a system that consistently produces outcomes we call failures but which are working exactly as intended.

Introduction

The Great Degradation

Remember when getting on an airplane felt like an adventure? When your seat had enough legroom for an actual human being? When restaurants had names like Mel’s Diner and the Blue Moon Cafe, each one a little universe with its own personality?

That America didn’t just disappear. It was murdered.

Walk through any American city today and you’ll find the crime scene. Strip malls stretch like suburban graveyards, filled with identical gray boxes. The bones of old department stores sit picked clean and left to rot while their former owners count tax write-offs. Airlines have turned the miracle of human flight into livestock transport.

This isn’t progress. This isn’t the invisible hand of the market doing its mysterious work. This is enshittification, and it’s eating America alive.

The pattern is simple once you see it. Private equity spots a profitable business with loyal customers. They swoop in with borrowed money, load the business with crushing debt, then strip everything that made it special. Cut the staff. Cheapen the ingredients. Raise the prices. Extract every possible dollar until there’s nothing left but a hollow brand name stuck to the front of another gray box.

Scattered across America, a few stubborn holdouts refuse to surrender. Trader Joe’s still treats its workers like human beings and its customers like friends. Costco still believes that taking care of customers and employees might be good business. These companies have access to the same soul-crushing technologies as everyone else. The difference is they use computers to help their people do better work, not to replace their people with cheaper machines.

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