Let me confess: I’ve spent more time obsessing over stock tickers than I have on my dating life. And yet, here I am, staring at the screen, wondering if I’ll ever figure out how to turn $1,000 into $4.69 million. But enough about my failures-let’s talk about Progressive (PGR), the insurance stock that feels like it’s been quietly sipping espresso while the rest of us are still groggy from the morning commute.
Units of Cryptocurrency Lost: 12. Hours Spent Watching Charts: 9. Number of Panicked Texts to Friends: 24. But here’s the thing: Progressive isn’t some fluke. It’s the kind of company that makes you wonder if it’s been secretly whispering to the financial gods. Back in 1990, if you’d bought $1,000 worth of PGR, you’d now be sipping champagne on a yacht. I’m not sure if that’s impressive or just a reminder of how bad I am at investing.
Disciplined underwriting? That’s Progressive’s secret sauce. In 1965, while other insurers were playing it safe, Progressive’s CEO Peter B. Lewis decided to do something radical: actually make money from policies. It’s like the difference between a friend who always pays back loans and one who just… disappears. The auto insurer’s use of telematics-tracking mileage, speed, and braking time-feels like something out of a sci-fi novel. And yet, it works. They’re not just selling insurance; they’re selling peace of mind (and a side of data).
Here’s what I admire: their 23-year streak of hitting a combined ratio of 96% or better. That’s not just consistency-it’s a level of focus that would make a monk blush. Over the past year, they’ve generated $16.5 billion in free cash flow. I can’t even remember the last time I had $16.5 billion. Probably when I accidentally opened a spreadsheet and forgot to close it.
A high-quality stock? Absolutely. In a world where most companies are just trying to survive, Progressive is the one that’s already won. Its ability to adapt, from pricing precision to operational efficiency, makes it a durable moat in a sea of chaos. And for long-term shareholders? Well, let’s just say they’ve been rewarded with the kind of returns that make you question every life choice that didn’t involve buying stock.
So, here’s to Progressive: the cash-generating machine that makes me feel both inspired and slightly inadequate. Maybe one day I’ll be that disciplined. Until then, I’ll keep watching charts and wondering why I ever trusted Bitcoin.
💸
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2025-09-22 13:22