alt Hacker NewsThe wild part to me isn’t 9 figures is good/bad, it’s that in year 8 the company still has a single human as the default DRI for culture, zero‑to‑one work, and existential decisions. If you’re going to turn down generational wealth, the least responsible version is keeping everything psychologically and operationally coupled to you; the grown‑up move is making yourself cheap to replace and designing a succession plan you’d actually be willing to trigger on bad news, not just a term sheet
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That's never quite how it happens, they can't let go. You can see it in the "Office of the CTO" thing. I've seen that one many times before: when confronted with the endless complexity and depth of building a real global product, they recoil. Everything takes too long, is too uninteresting. They instead build up this parallel engineering organization that is showered with money, headcount and C-level attention to build the new moonshots, with the subtext that whenever it's "ready", it will be thrown over the wall to the actual engineering org. It's a speedrun to make your engineering talent leave.
That was the whole point of writing this series: to show how my role evolves and what I’ve had to give up. Trust me, if it were up to me, I’d still be having fun coding (even more so these days). There’s an entire section on delegation in this year’s post.
I’m not the single DRI for culture at all. We have many strong culture carriers, which has made scaling to 100 people much easier than scaling to 20. That said, culture is still one of the core responsibilities of founders, in my opinion.
Also, OCTO isn’t about me wanting to innovate. It’s about giving certain engineers permission to not be tied to a roadmap and to stay fluid.