[orliesaurus]

The 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

[elwatto]

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.

[dangus]

The odd part of this journey to me was basically:

1. We aren’t going to sell.

2. Confiding with your spouse with clear concerns about current levels of stress and time commitment.

3. We can resolve a lot of the stress and sustainability problems by (among other things) raising another funding round!?

I did a double take…isn’t that just inviting more stress, more pressure from investors, more expectation to grow and exit?

I find it hard to relate to this C-suite life and logic, it seems so hyper-capitalist and backwards. There are so many oddly revealing bits of this piece that are like a window into the world of an alien being compared to my perspective.

It’s like Star Trek where there’s an alien race for every personality type and/or representation of a dominant emotion. The C-suite aliens would build their society around building products, meeting customers, finding takeaways, making org changes, etc. Societal enjoyment comes from work accomplishments, and the family decides that stress and time apart is worth it because work is “your baby.” Not really quite like the Ferengi because the Ferengi would have taken the 9 figure exit and dumped it into the next scheme.

Meanwhile the viewer is most familiar with the even-keeled baseline of the Federation where they used their technology to end capitalism and spend their time exploring the galaxy and prioritizing their family and friends. You end the episode with “I’m glad I kept an open mind but I still wouldn’t want to be the C-suite aliens, I like hanging out with the Federation.”

[stefan_]

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.

[throwway120385]

Oh wow you just described our last CTO to a T.