[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.”

[elwatto]

Maybe we are wired differently, but as I wrote in the final part, I’m actually more motivated and see myself going much longer (which is what investors want, as long as there’s growth). It’s linked in the post, but a big part of the round was secondary, which helped reduce financial stress for founders and early employees.

[dangus]

Yes, wired very differently. I think that’s why I used the Star Trek analogy.

This motivation is like a strange curiosity to me. This pursuit of product is so foreign to me, and from the outside it doesn’t seem healthy. But I guess if the Klingon like going into glorious battles to the death better than chilling at home with their family, who am I to question their motivation?

I build stuff at work because it’s a financial obligation, because it’s better than cleaning bathrooms or waiting tables for a living. If I had some kind of better option for paying my bills with less labor involved I’d take it in a heartbeat.

[madaxe_again]

I felt the same as you - turned down several acquisition offers, the company was my baby, etc.

Year ten, my partner turned around and stuck a knife in my back, and I found myself railroaded out and battered into submission by lawyers. Exited with token equity, and a small cash payment to get me to fuck off so they could gut the company.

Retrospectively, I should have quit while I was ahead, and I should have realised that while I cared about the company, it did not care about me.

Also, cofounders… you never find out who they actually are until one night you hear the click of the hammer of the gun against your head cocking.

[clarky07]

raising the round is them selling part of the company. enough of the company that they no longer ever have to worry about money again. yeah that removes a lot of potential stress. the company can fail now and it won't ruin him. gives him more freedom to keep building.

[dangus]

“more freedom to keep building”

This is the disconnect to me. This phrase has tech industry cult vibes to me.

I don’t see “freedom” and “building” as words that mesh together.

I see “building” as something I’m obligated to do to pay my bills. I do it because it’s preferable to other forms of labor. As soon as I have the financial means to stop doing it, I’m out.

[collingreen]

Hardly a cult. So you don't like building things. Fine. Nothing wrong with that. Plenty of folks, however, do love building things. When I dream of freedom unlocked by money I love the idea of building things still; the difference is building what I want, how I want it, without being trapped.

[dangus]

There’s a big difference between “building things for fun and accomplishment” and taking on the intense obligations of continuing to be a CTO when a major exit is on the table.

I totally understand that there are people who relish in the challenge, feeling needed and important to their team, and the prestige and visibility, but I don’t really understand what their brains are doing and what.

OP talked about the luxury of being able to fly out the grandparents to help out taking care of the kids when things get busy at work. That doesn’t sound like freedom to me.

[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.