I’m Joey Rodriguez. I’m a product leader, and I’ve run product across six industries and up and down the capital stack, from venture-backed startups through buyout, with depth in pricing, product-led growth, and practical AI. I currently work with private-equity-backed companies as an operating partner and fractional chief product officer, with capital alongside. That last part is why this exists: I’m usually still in the room when the decision comes due.
This is a place for long pieces about the decisions that determine whether a technology bet pays. Most of it comes out of my own record, dated and specific. What I decided, what it cost, what I got wrong, and what turned out to still be running years after I left. Nothing in that record ever failed at the build step. Every failure I can point to happened somewhere before it or after it, and that is more or less the subject.
Some of it is current rather than historical. I build software with AI agents, and now and then a piece will be a field note from inside something unfinished, screenshots and all. Those are rougher on purpose. The interesting part is usually what the tooling made easy and what it quietly made worse.
One piece a month, on the third Wednesday. They run long, because the argument usually needs the room. If a month goes by without one, it means the piece wasn’t ready.
What this is not: a tips newsletter, commentary on the news cycle, or advice from someone who moves on before the results arrive. I’d rather be checkable than quotable.
If something here describes a decision you’re in the middle of, write back and tell me how you’re framing it. That’s the conversation this whole thing exists for.
