Hacker News Board Hacker News, browsed like a classic message board
Live data from Hacker News

My role as a founder-CTO: year 8

miguelcarranza.es

Post reply on HN
Print view View original

101–110 of 152 posts

Re: My role as a founder-CTO: year 8

#101

Post by twodave »

cj wrote: post #78
theptip wrote: post #76

Earlier quoted context omitted.

I dunno man. A useful psychological trick in this scenario is to imagine you were on the other side of the transaction. Say you have nine figures in your account. Would you push it all into this company to be able to have a fun job? Seems completely insane to me. F You Money means you can spin up whatever projects you want for the rest of your life. Even if your dream job is worth $100m to you, is the delta between t…

> Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much? At least for me, regular financial decision making breaks down once the numbers are above a certain amount. E.g. You won’t feel 10x better about a $100m windfall vs. a $10m windfall. The best case scenario for a lot of founders is to do a secondary, cash out / de-risk, and keep on…

I think of an amount like $10m as “retire well, leave some for the next generation” kind of money. $100m is more like, “retire well, leave passive income for N future generations.” That extra 10x is super compelling.

Re: My role as a founder-CTO: year 8

#102

Post by dangus »

elwatto wrote: post #77
orliesaurus wrote: post #31

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…

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, cu…

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.”

Re: My role as a founder-CTO: year 8

#104

Post by DANmode »

harmonic18374 wrote: post #46

I feel RevenueCat is on shaky ground, their market position can only get worse and worse as Apple and Google improve their complimentary offerings and they are forced into more A/B testing that directly competes with others. Recent StoreKit changes this year close a lot of the remaining gap. I would have sold. I wonder why they chose not to.

Users, while not at the top of the list, is probably on the list.

Re: My role as a founder-CTO: year 8

#105

Post by elwatto »

phpnode wrote: post #99
cebert wrote: post #85

I’m a big fan of the idea of an Office of the CTO group reporting directly to the CTO that helps with prototyping greenfield projects and exploring innovative ideas. I believe a group like this would be beneficial for larger organizations, like the one I work in. There are numerous opportunities for market disruption, but it becomes increasingly challenging to make bold bets as the company expands. If I had the power…

If that group is necessary then it's a damning indictment of the product/engineering culture. The CTO's job should be to fix the broken culture, not try to side-step it.

Hard disagree. Culture isn’t the problem, org structure is. You can call it an experiment or even a hack. Every team is already innovating within their scope, and splitting becomes easier as that scope grows.

What is too much is asking an Engineering Manager to start a completely independent product line that may go nowhere. It’s far more effective to rely on senior, staff+ engineers who don’t need management and have experience taking things from 0 to 1. They can build an MVP quick. Once we see real signals of PMF, we can then build a team around it (or drop it)

Re: My role as a founder-CTO: year 8

#106

Post by elwatto »

j7ake wrote: post #90
bcantrill wrote: post #27

Earlier quoted context omitted.

I know from the outside this seems very simple, but it's more complicated than that. Certainly, if the objective is (merely) security for one's children, that can be secured with much (much) less money (and likely was secured in the secondary that the author makes reference to); having nine figures of wealth is not an unvarnished good, and in particular makes raising grounded, self-reliant kids pretty complicated. To…

You forgot to account for the 100+ employees. The liquidity event would have helped their families as well.

I won’t disclose details out of respect for the other party, but no, not necessarily. As I wrote, it was a good deal for the founders and some investors, but not for everyone, including employees. There are many ways to structure a sale, and unfortunately not all of them split the cake equally.

Re: My role as a founder-CTO: year 8

#107

Post by charlie0 »

nickelbob wrote: post #95
cebert wrote: post #85

I’m a big fan of the idea of an Office of the CTO group reporting directly to the CTO that helps with prototyping greenfield projects and exploring innovative ideas. I believe a group like this would be beneficial for larger organizations, like the one I work in. There are numerous opportunities for market disruption, but it becomes increasingly challenging to make bold bets as the company expands. If I had the power…

Shouldn't this live under the VP of Product?

No, product shouldn't be the head of an engineering team.

Re: My role as a founder-CTO: year 8

#108

Post by vinnymac »

Sparkyte wrote: post #103

I kind of want to be a CTO somewhere. So much bureaucratic stuff to become one though. You usually have to be someone's friend or start a company yourself.

Same, I am looking forward to starting my own company in the next year or two, and exploring the CTO role, especially after so many years as a Staff+ operating as an arm of CTOs and learning the ropes.

Re: My role as a founder-CTO: year 8

#109

Post by elwatto »

cj wrote: post #78
theptip wrote: post #76

Earlier quoted context omitted.

I dunno man. A useful psychological trick in this scenario is to imagine you were on the other side of the transaction. Say you have nine figures in your account. Would you push it all into this company to be able to have a fun job? Seems completely insane to me. F You Money means you can spin up whatever projects you want for the rest of your life. Even if your dream job is worth $100m to you, is the delta between t…

> Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much? At least for me, regular financial decision making breaks down once the numbers are above a certain amount. E.g. You won’t feel 10x better about a $100m windfall vs. a $10m windfall. The best case scenario for a lot of founders is to do a secondary, cash out / de-risk, and keep on…

Thanks for your message and point of view. You’re probably the only person here who has been presented with a similar scenario, and this is exactly how I felt.

Re: My role as a founder-CTO: year 8

#110

Post by clarky07 »

dangus wrote: post #102
elwatto wrote: post #77

Earlier quoted context omitted.

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, cu…

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 e…

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.
Post reply on HN