How do you expect to continue to maintain that distance from sponsors under the pressure to grow?
Could CTO Lunches remain small?
Are you organized as a 501(c)(3), a charity where donations are tax-deductible and therefore must not be used for commercial purposes? (That would be effective but is almost certainly too much overhead.)
Since you asked, and I started this project simply to benefit the community, I'll dump my thoughts on scaling here (would appreciate any feedback!)
1. Each city has a captain, who is responsible for setting the time & place of each monthly lunch (and possibly for facilitating monthly local email threads / activity updates). A good captain is key to keeping that small, local community feeling going. <<< This is the main answer to your question.
EDIT: I think it's super important to reiterate that each local captain is an engineering leader themselves. It's not some marketing person from a dev-oriented company.
2. Sponsors -- we only have 1 sponsor right now (name.com), and it's about a month old. I met them while organizing Boulder Startup Week because they were volunteering to help organize BSW too. They're headquatered in Denver, so 1 person from the company comes to the Boulder & Denver lunches (they don't give pitches, they just eat lunch and mingle). I still need to talk with name.com if they're interested in continuing to sponsor the group world wide, which would be cool because they're great at video content and they hate timeshare pitches as much as we do. But if they'd like to keep it local, then I think all sponsors should be local. I know in each startup community there are small to mid size companies doing cool, valuable work and not being jerks about it. Those are the types of sponsors that would be valuable to the group, so that's what I'd help focus on.
3. Even more value -- I really haven't thought this through, but I'd love it if I could spend all of my time providing more value to the group. Outside of the time I've spent being a CTO & co-founder of a VC backed company, I love writing books, doing interviews (Kevin & I did StartupCTO.io, a podcast for a while), putting on events, and building little SaaS tools to help people. I'm not sure how to support myself financially to do that (maybe there's a paid premium membership that's optional for people? But the email list & in person event would always be free! Maybe sponsors help me with that?), but that would be amazing.
Oh and structure of the email list:
* Everyone
* Colorado
* Texas
* ...
where members can always email just their local group, but they have the option of participating in or starting discussions with the international community.
Could CTO Lunches remain small?
Are you organized as a 501(c)(3), a charity where donations are tax-deductible and therefore must not be used for commercial purposes? (That would be effective but is almost certainly too much overhead.)
(Cool project, btw.)