I suppose you've fundraised at some point in the past 13 years. If you have, the advice you probably received was to start with the tier 3 VCs, hone your pitch, and move on to the VCs you really wanted to work with once you had your pitch nailed.
The same principle applies here. The more interviews you do, the more comfortable you'll get, the better it'll go. And who knows, it might work out with one of the first companies you interview at!
That sounds like a good idea but oddly enough the first startup (the one I was at 10 years) only raised a friend and family and we were able to land customers and bootstrap from that and the second one I bootstrapped out of a little cash I got from the first one so no investors to go to per say.
I have an email address with a personal domain, and my "legacy" Gmail account. I like having an email address with a custom domain, and I think that it's a (weak) signal about your technical aptitude/geekiness. If you want things to just work, Fastmail, protonmail and presumably other email providers will let you manage this without any hassles. I use protonmail and I haven't noticed any dropped emails.
The main pros & cons, apart from vanity, are IMO about security and robustness. With a custom domain you can change email providers, or you can recover from being locked out. (Just read any horror story about the day Google decided to freeze an email account). OTOH the custom domain name adds one more point of failure, either for delivery (if you have to handle SPF/DKIM yourself) or security - if someone gets into your registrar/NS account, they can re-route your emails. So you want to make double extra sure your accounts are locked down tightly.
Define "middle class Americans"? Hard to give a precise answer otherwise.
A few (other) explanations:
* QoL is hard to be rational about, and is something that (I think) has to be experienced first-hand. European salaries are most probably lower for comparable jobs (they certainly are for high-wage workers) but pack more punch because of better social benefits and, depending on where you live, lower CoL. However it can be hard to convince yourself that 40 k€ in Spain affords you a better QoL than 80k$ in California unless you've experienced both. I mean, 40 is much less than 80, right?
* the "American Dream" is still a big part of the American (and global, for that matter) psyche. I would wager most Americans think the US is a place to emigrate to, not from. I don't know if many middle-class Americans would spontaneously envision emigrating to Europe. This is probably even more true for descendants of recent immigrants: if your family struggled to get to the US, why would you consider leaving?
* Ability to live abroad, in particular mastering a foreign language well enough to live and work in the country
* I'm not sure how well employability travels. You can work as a developer in just about any country but I think this is an exception. A medical diploma does not transfer well between countries (e.g. you probably need to start again as an intern, re-take exams, etc.), neither does a law diploma. More "middle class" jobs will have similar barriers to entry. E.g. if you're a plumber in the US and move to Europe you have to deal with different construction codes, installed base, local habits... Same thing if you're an auto mechanic: different car manufacturers, different regulations, etc.
Americans in HCOL locations have a third option to Europe, and that is the rest of the United States. RoUS provides close to a factor of two cost savings, you speak the language, same level of bureaucracy, close (enough) to family, similar enough culture to be comforting but with enough differences to make it interesting (desert Southwest, Deep South, New England, Florida Keys, Midwest, Appalachia, PNW, Intermountain West, Alaska, Hawaii, Texas…). Canada, Mexico and the Caribbean a drive/cruise away and provide their own long term opportunities. The United States is much more culturally diverse than the few places Europeans choose to visit for extended stays.
The United States offers a political stability that Europe has yet to demonstrate long-term (cherry-picking here, but let’s say over the last 150 years, two modern lifetimes). The comic opera/snuff film of European wars in the 1900s did provide 104366 young Americans with a forced permanent relocation to Europe. Not a positive memory for Americans.
And Americans can develop a community in the United States that achieves many of the charming aspects of European life. Americans have both the freedom and gumption to do that, if they wish. Americans are not limited by land nor resources, intellectual, cultural or otherwise, nor vision.
I did a (regular, non tech-focused) executive MBA at 35, after about 3 years as a developer and 10 as a technical manager. I would absolutely do it again.
After my MBA, I transitioned into a CTO role; I'm fairly sure I would have gotten the role without the MBA, but it helped. My feeling is larger companies value MBA diplomas more.
Aside from the career boost, what I got out of my EMBA:
* exposure to new topics, some of which I loved (and use on a regular basis), others that I hated (and now I have better clarity on what I don't want to do)
* finance is high-school math with fancy words; it's really easy to pick up if you have a mind for numbers
* this holds for a lot of topics (e.g. strategy, operations management, etc): a little domain knowledge, good heuristics (both of which you learn during the MBA) + general logic and problem-solving skills (which you probably already have as an engineer) go a long way
* I built a good network and made a few great friends
A few observations from your initial description to maybe help you figure out how you want to handle this.
1. Most people calling the helpdesk are in a very specific state of mind: they have a problem and they want it solved. They're not curious about where the problem comes from, they don't want to know how to avoid it next time, they don't want to learn a better way to do things. They have an interrupt that prevents them from resuming the rest of their day, and they want that interrupt dealt with as quickly as possible. For people in this frame of mind, trying to be helpful usually backfires. You solved their problem, that's what they called for, they're not interested in getting educated. These people will always look for the fastest way to solve their problem and the one which requires the least amount of cognitive activity on their part. Anything that makes the conversation longer than it needs to be or requires them to engage more brain cells is a downside.
2. It seems like there's a status issue as well. You mention that these users "operate beyond [your] abilities" so maybe a bit of inferiority complex on your part? In which case explaining how you know better than them could be a way for you to even the score, so to speak. But then this triggers its own opposite reaction, "I have a PhD so of course I can figure out how computers work if I put my mind to it, stop talking down to me". To which you respond, effectively, "having a big brain and knowing how things work are 2 different things, you may be book smart but I am street smart" and it escalates.
My advice, insofar as it makes any sense, is to let go of all this social context when you're in helpdesk duty. Take the call with the objective to help a human being get on with the rest of their day with as little fuss as possible. Accept that some will be grateful and say thank you, and others will be douchebags, because that's how human beings work. Trust to karma to reward the good ones and punish the douchebags. Accept that you can't teach someone who doesn't want to learn. Don't bring your ego into it, because winning technical arguments with someone shouldn't be how you measure your self-worth.
Good call. A lot of red flags in here, including one I haven't seen in the other comments: the relationship with the brother. If you're both technical, you have more seniority than him but he has more shares and co-founder status? You're in for recurring headaches about who owns the tech, and you'd always be in the minority.
I love 202 for sentimental reasons (latest problem available when I picked up PE, seemed impossible at the time, felt thrilled to solve it) and 422 because I find the solution so elegant. I haven't touched PE in years but I still remember these problems and their solutions off the top of my head.
When I first discovered PE* I checked the latest available problem, which was 202 that week. I remember thinking at the time that it was impossible to solve.
Fast forward a couple of years and a lot of solved PE problems. I took another go at 202 and I finally figured it out. The feeling of accomplishment I felt then...
*through an xkcd comic (https://xkcd.com/353/). The alt text mentions 20 small problems, which are problems from PE (IIRC this was specified in the now-defunct xkcd blog)
The answer to this question is almost always: "the stack you're most comfortable with".
In your case, given that you have (apparently) a strong Python background, you should try to see how far you can go with Django and some vanilla js. If your front-end doesn't absolutely have to be a SPA, you'll be up and running and productive much more quickly with a fairly simple (server-side logic and page generation) and user-friendly (Django) stack. No need to jump into node, npm, etc.
If you want or need to get more fancy with the front-end, vue.js is relatively easy to pick-up, fairly future-proof (as another poster pointed out, vue and React are the two main choices), and can be included fractionally in your existing pages without a complete overhaul.
The same principle applies here. The more interviews you do, the more comfortable you'll get, the better it'll go. And who knows, it might work out with one of the first companies you interview at!