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I started my 20 year career in the hosting and ISP business. I believe you are asking if there are negative consequences to adding a CDN like cloudflare to your domain. I would say there are only benefits. These days, the performance of your website is a ranking factor. Having the site responsive to requests regardless of where in the world they come from, can only be a benefit. My experience of Squarespace is that it hasn’t kept up with the innovations in CDN and the great things that Cloudflare have been doing. If you want to chat further, let me know!
I’ve spent nearly half my career working in the hosting and ISP business. Back then it wasn’t so crowded :) Personally I believe you can deferentiate in many ways but first you must understand what the pain points are with successful hosting companies. Also what level of customer are you servicing? DigitalOcean IMHO do an amazing job but it’s not for the novice. Providing ease of use, value for money and legendary customer service are the 3 areas I would start with first. Happy to chat more if you’re keen.
I've been bootstrapping my own startup for about 12 months. IMO if you take a day job, you're sufficiently distracted to fail. I'm not sure how far down the entrepreneur path you are, but you'll realise that launching your own startup will take every hour you have. You'll work harder than ever - and you'll want to, because this is your idea. I sounds like you have accrued some skill and knowledge, so I would recommend consulting your expertise out to others. This let's you stay in control of your time, you pick the projects. If you can work on projects that are time flexible, then even better. If you can work in an area that also ties into your startup, then you're winning. IMO your "career progression" is what you learn from the entrepreneurial experience. To succeed, you need to put in 200% and the key is to make mistakes and make them quickly. If it all doesn't work out, then you can quickly get back to looking for a good job at a good company.
Also agree with Joseph regarding the risks of sharing names that you don't already own. For me, I'd say wisechat.co is the best. Why? It's two dictionary words, there's no ambiguity when saying it out loud, .co has become as respected as .com. The reason I'm not for crowdsage.com is that 'sage' is not a word used commonly so you could still have to explain it - and you never want to have to explain or spell your domain/email/company name. Same applies to the first two, and wisespace.me is phonetically poor with two 's'. That's IMHO anyway. Happy to discuss in detail over a call. Good luck!
If I understand correctly, you want a definitive list of .edu domain names to compare users against to automatically approve them for your service?
The most authoritative list would be held by Educause - http://net.educause.edu/edudomain/index.asp but you won't necessarily be given the list. I would try dropping them an email anyway.
In the meantime, here are two other sources (but likely incomplete) that you could use.
If you'd like to discuss more, please schedule a call!
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I'd recommend having a strong social media presence. You could use Knowem.com to check availability of social media channels and they will show you the top ones you need to be on. Today you should at least have an Instagram in addition to a Facebook Page and a dedicated Twitter account. I can explain how to set all of this up and how to easily manage it too.