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Gary Tan’s 23-Role AI System: What Solo Entrepreneurs Actually Need to Know

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🎧  Jim reads this post

Look, I’ve been watching Gary Tan, the Y Combinator CEO, quietly build something that actually solves a problem I’ve had for years. He called it gstack, and he just open-sourced the whole thing. Twenty-three AI roles built into one system, and honestly, when I first heard about it, I thought it was marketing nonsense. Then I actually looked at what it does, and I realized this guy just handed us the instruction manual for running a one-person company without losing your mind.

The basic premise is stupid simple: instead of you being the CEO, engineer, designer, QA tester, security person, copywriter, and project manager all in one exhausting rotation, you give Claude access to play each of those roles when you need them. You’re not managing a team. You’re directing a system that knows how to think like each position on your org chart. It’s less “hire people” and more “split your brain into functional departments.”

Why This Keeps Coming Up

I think what’s happening here is that we’re finally hitting the wall where one person can actually build and run a real business without hiring people or burning out. That sounds hyperbolic, but we’ve been saying “AI will change work” for three years and mostly seeing people use ChatGPT to write emails faster. This is different because it’s not about speed-it’s about capacity. You can actually do five jobs at once if the system knows the constraints and thinking patterns of each role.

For GenX specifically, this hits different. We came up in the corporate 90s and 2000s where the dream was to escape that-to start something on your own terms. But being the only person meant you were also the only person, which meant you did all the work and nobody else got the credit or the burden. Now the math actually changes. You can be the founder and director, and let the AI handle the execution across multiple functions.

What I Actually Found Out

The part that actually impressed me was something called Skillify. You do a process once-literally any process, like how you manage customer feedback or structure a product roadmap-and you run a command slash-skillify, and Claude extracts the pattern you just used and turns it into a reusable skill. You do that same process the next time, and it’s already learned how you think about it. It compounds. Every session makes the system smarter about how you specifically work.

That’s not just faster. That’s actually a feedback loop. Most AI tools are static-they’re the same for everyone. This gets better because it learns your actual workflows. After a month of using it, the system knows how you make decisions, what questions you ask before shipping something, what your quality bar is. It’s building a model of you as a manager and operator.

The other thing is that it’s built in layers. You’ve got your core roles-CEO, engineer, product, design. But then you’ve got supporting roles for security, QA, shipping, analytics. You can call on the right expertise for the moment you need it, instead of keeping someone on payroll for 10 percent of the work. That’s the whole efficiency play.

What You Can Do With This Today

Honestly, the floor for entry is low. If you’re running a solopreneur business or a small product, you could start using gstack tomorrow and begin mapping out your actual workflows. You don’t have to use all twenty-three roles. Start with CEO and engineer, or whatever your two biggest roles are, and see how the system responds to your actual work.

The real move is documenting your processes while you’re doing them. That Skillify command only works if you’re actually capturing how you think. So when you’re making a decision, writing it down for Claude to learn from-that’s when the compounding actually starts. You’re not just automating things. You’re encoding yourself.

This is the kind of tool that sounds incremental until you use it for six months and realize you’ve basically built an operating system for your business brain. Which, at fifty, feels like exactly what I needed.

Hit me up if you’re playing with this. I’m curious what roles people actually use the most.

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