Welcome to Brian Bailey | Oak Stone

If you're reading this, there's a good chance you’ve already figured out that the headlines don't tell the full story. Markets are up, the Fed is boxed in, and yet the feeling on the ground—in boardrooms, on balance sheets, in the real world—is something else entirely.

That tension between appearance and reality is exactly why this Substack exists.

Recently, a good friend of mine—a sharp, small business owner and a great writer himself—read something I sent him a few weeks ago. It started as a quick text rant on the absurdity of rate expectations and turned into a full blog post. He told me I should publish it. He thought others might find it valuable, or at least enjoy the perspective. After thinking about it (and rewriting it about a dozen times), I figured he might be right. So here we are.

I'm Brian Bailey, a private equity investor, former Chief Investment Officer of a publicly traded asset platform, and the founder of Oak Stone Capital. I've spent the past 30 years structuring, deploying, and managing capital across private markets—real estate, insurance-linked assets, public and private credit—with a singular focus: align incentives, protect principal, and generate alpha.

Oak Stone is the platform that brings those ideas to life, not for the institutions I’ve done that for throughout my career, but for everyone else, well at least all of you accredited investors out there. We're not a syndicate, we're not a prop shop, and we're definitely not some Zoom-era fundraise experiment. We're an operator-led investment firm built on execution, not exposure—and right now, we're raising capital for a $25 million real estate fund targeting short-duration, high-return residential redevelopment in one of the most supply-constrained submarkets in the country (if that caught your eye, reach out, we’ll send you more info, but this blog isn’t a marketing piece so that’s all we’re going to mention about the fund we’re presently raising).

This publication isn’t just a megaphone for what we’re doing at Oak Stone. It's where I’ll share what I see happening across markets: the disconnects, the distortions, and the structural changes most people won’t notice until it's too late. Sometimes that means talking about interest rates. Sometimes it means pulling back the curtain on the absurd mechanics of fund structures, institutional capital, or political misdirection. Always, it means offering a perspective grounded in experience—and a bias toward action.

If you're tired of echo chambers, meme-driven markets, and passive capital stuck in vehicles it doesn't understand, or if you’re just simply trying to make sense of it all, you're in the right place. We’ll try to do a little bit of all of that!

Welcome to Brian Bailey | Oak Stone.

Let’s get to work.