Jack Boudreau

Everything didn’t get worse by accident. It got worse on purpose. There’s even a word for it. The term is “enshittification,” coined by writer Cory Doctorow, and once you see the pattern you can’t unsee it. Nearly every major platform runs the same four-step playbook: build something great at a loss to hook you, get you dependent on it, quietly reduce your alternatives while raising prices, then extract as much as possible without improving the experience at all. Your streaming apps, your rideshares, your subscriptions, all of it. The cleanest example is the one you feel every time you travel: a $13 Uber packed with friends in 2012 is a $60 solo airport ride now. Same company, same app, wildly different deal. When you hear a company raised a billion dollars overnight, it’s usually because they proved they could run this exact playbook at scale. I’m Jack, I read the boring stuff so you don’t have to.

“This is fine”

Forget Zillow. People are now using Strava to figure out where to live. Strava’s global heatmap shows glowing lines everywhere people run, walk, and bike. A few weeks ago someone pulled up the Chicago map and realized it’s basically a proxy for wealth and safety, because consistently active people skew toward disposable income, leisure time, and access to parks, trails, and good sidewalks. The bright zones tend to line up with the safer, more walkable, more expensive neighborhoods. And there’s research behind it: a Boston study found runners favor streets that feel clean, open, and safe, and a North Carolina study found running activity correlated with money flowing into home renovations. The caveat: it’s a proxy, not gospel. Not everyone uses the app, Strava itself says the map isn’t meant for exact comparisons, and in some cities it just mirrors existing inequality. But as a free first filter when you’re moving somewhere new, it’s shockingly good. Zillow tells you the price. Strava tells you what it feels like to actually step outside there. I’m Jack, I read the boring stuff so you don’t have to.

Layoffs used to hit the bottom of the org chart. This new wave is coming for the middle, and if you took a manager title for the raise, that’s you. Uber just cut about 3,300 people (10% of staff), its biggest layoff since the pandemic. But the details make it a manager story, not a generic one: the company cut its number of managers by 20%, reduced teams of just one or two people by nearly half, targeted employees more than seven layers below the CEO, and pushed some surviving managers back into individual-contributor roles. Notably, the CEO did NOT blame AI, he framed it entirely as cutting “management bloat” to move faster. In the same move, Uber limited remote work to about 1% of staff, so it doubles as an RTO crackdown. The reframe: in 2021-22, the only way to get a real raise at a lot of companies was a promotion into a manager title. Many people took it and inherited one or two reports. That “manager of two” is now the most expensive, least essential line on a spreadsheet someone’s being told to flatten. It’s part of a broader flattening trend across tech (Google has reportedly cut management headcount significantly too, though those figures are secondhand). If you climbed into management for the money and not the leadership, consider this your heads-up. Sources: TechCrunch, CNBC, Forbes, Bloomberg, Sept 2026. I’m Jack, I read the boring stuff so you don’t have to.

We named an entire era after Gilded Age inequality. We just quietly blew past it. The Gilded Age was the late 1800s: rapid industrialization, robber barons like Rockefeller and Carnegie sitting on enormous fortunes while everyone else struggled. It’s the textbook example of extreme wealth concentration. Economist Paul Krugman ran the comparison, adjusting for the fact that the US population has more than tripled since then. In 1918, the five richest Americans held wealth equal to about 2.5% of GDP. Today, the fifteen richest hold about 8.5% of GDP, more than triple the concentration of the robber baron era. Zoom into the very top and it’s starker: the richest 0.00001% used to be four families. Today it’s eighteen, and they hold more than their Gilded Age counterparts ever did. The wild part is we teach the Gilded Age in history class as a cautionary tale. And our country isn’t even 250 years old yet. I’m Jack, I read the boring stuff so you don’t have to.

The retirement wave everyone predicted never came. Now corporate America has a succession problem it didn’t plan for. For years, economists forecasted a “Silver Tsunami,” boomers aging out of the workforce in one great wave. It never struck. Labor force participation among people 65 and older just hit 19.2%, up from around 12% at the turn of the century, and as of June, 42% of sitting CEOs were 60 or older, an elevated level versus historical norms per Cowen Partners’ review of SEC proxy filings. Boards from Boeing to Verizon to Cracker Barrel keep reaching for older or previously retired chief executives. There’s a fair case on both sides. Having volunteered at nursing homes growing up, I’ve seen firsthand what happens when people lose their sense of purpose, and for someone whose identity has been their job for 40 years, retirement can be genuinely destabilizing. I have sympathy for that. But the flip side is a generation of rising talent in their 30s, and disciplined operators in their 40s and 50s, who never get the boardroom reps because nobody at the top ever steps off. The ladder stops moving. And that’s before you look at what the same dynamic is doing in politics. Source: Entrepreneur, Sept 2026. I’m Jack, I read the boring stuff so you don’t have to.