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Good article. As you get into the day-to-day work, I find that most things are far more meaty and have more depth than the examples here. I understand that the audience and length of this post surely couldn't "solve all the things."

However, it would be nice to have the management version of a rubber-duck, a pair, a mentor, a consultant or a life coach for people in our roles. I don't know if anyone else shares this opinion but I would be interested in a virtual meet-up where CTOs of startups and small businesses discuss best-practices and work through issues. It could be as simple as a mailing list. I suspect meetups and groups like this exist in-person but I live very far from the bay area and we're rural enough there simply is nothing nearby. If nothing like this exists, I would be willing to work and work hard with others to set it up. I think it would be so valuable to me that I wouldn't mind putting a lot of effort into getting it going.

I would also pay real money for the right mentor/CTO coach. Surely there are a number of passionate CTOs/Past CTOs that wouldn't mind passing on their legacy and mentoring me? If any of this at all sounds interesting, my email address is in my profile.

Exec / C-level startup coaches do exist, they tend to be pretty pricey though. I had a chance to chat with https://www.reboot.io/ a while back, they seem to be a good place to start. We tried putting together a CTO meetup here in SF several times, but it's worse than herding cats, everybody is super heads-down in the work 24/7.

Thanks for the share, I will look into it. I wonder if their isn't as large of a demand for this type of support system in SF? Everyone seems very connected, has a VC network and may even have a seed-operated Alumni network and mailing list. I agree, they probably have their head down and are building their product. As they should. When they come up for air though they probably have a half-dozen mentors at their disposal. I'm not sure, that of course is all conjecture :)

There's definitely CTO school in NYC, because we've mimicked it here in Melbourne, Australia[1]. I'd be surprised if there wasn't one for SF.

[1] And it's from whence I was first shown this article... :-)

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