[angersock]

Three mistakes that lept out at me, some of which the author seems to identify towards the end: using new technology, allowing themselves to get politically sidelined by missing meetings, and getting too heavy into process.

It seemed like they'd have been better served by pushing back on the YC advice (requiring them to be at meetings), by picking boring technologies (python, Java, JS), and by stopping work on all of the other stuff (studio projects, etc.) that proved to be a distraction.

That said, the introduction of the Dwayne fellow really seemed like the root of most problems that weren't YC-caused.

[swampthinker]

That, and the fact that he wasn't meeting with the YC teams. If you're the CTO, it doesn't matter that you missed the initial meeting. The founding team should all go and meet.

[akkartik]

(Apologies in advance for sounding harsh. I have extreme empathy for the author. But this lesson is so easy to ignore that I had to really amp up the contrast before I could focus on it myself. So it seems worth stating plainly.)

"You must have at least 10% equity in the startup to be considered a founder by Y Combinator. Only founders can come to interviews if invited or attend batch events if accepted." -- https://www.ycombinator.com/apply

If he couldn't attend, it was probably because he didn't have the requisite equity.

Joining as a founding member with less than 10% equity in a startup without a product or customers -- after being ambivalent about joining -- seems like a really bad decision.

One hard lesson I've learned over the years is that status matters. And in the startup world, equity is a huge marker of status, outside of its potential monetary reward. The initial conditions under which you join a project act as a non-negotiable upper bound on how much say your collaborators will let you have on the big picture. Regardless of how much you contribute afterwards.

Some reading on status for other aspirational-Vulcan types like I used to be:

https://news.stanford.edu/news/2007/march7/sapolskysr-030707...

http://www.meltingasphalt.com/social-status-down-the-rabbit-...

https://www.amazon.com/dp/B003J5653Y

Tl;dr - humans are pack hunters. They can't survive outside packs, not really. As a result, the topology of the pack has a powerful warping effect on our brains. You can't break out of it. It is as real for humans as gravity. Within a group there's no "being so good they can't ignore you."

This is not to say that being low-status is always bad. Just that it's worth being very clear-eyed about your status in a group. If you aren't going to the YC dinners, you aren't the CTO. Not really.