Yes, why stay in a place that will charge you more and more and where the population may go "tax the rich" or such.

Once you enter into a higher level of wealth, you need to protect it. Now it depends where and how you structure your business. Allocation of preservation of wealth is a human goal.

If your business relies entirely on revenue, then in any regard you will be taxed - so it would help to find a satellite country that has a lower tax rate for revenue.

It also helps in case of any nasty liability lawsuits down the road for warranty or sheer incompetence/negligence. Having money/resources in a different part of the world, different from your customer base can shield your wealth greatly because requires more cash upfront from those with cause to sue. Easy to sue locally/nationally, but internationally, need to bankroll multiple people and outside of directly government intervention, you're pretty much safe and have alot of "time".

If income is by capital gains, it's entirely different and depends mostly how property/rights are treated/respected where you are. Especially taxes and how swaps/transfers are taxed.

Also differs if it is entirely Intellectual property as well. Local government rules for IP matter, and are not severely punished internationally, but you want to be able to protect and protest it, so local satellite offices are needed to ensure compliance. Depends which market of course.

So we covered general SAAS/Revenue, Capital Gains and IP.

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For your regular job, to resign and hire people. You can and should hire people along the way no matter what. Whether it'd be a virtual assistant/secretary or someone to organize - and then onboard more and more people that know your product/what you do/can contribute. You need to create departments and silos that push more into marketing, sales, reputation and general support. Marketing should be a profit center, support is usually a cost center - but you need to scale client acquisition and work. Automation is great, but, you can't automate everything and after a while you will get overloaded/overtaxed on day to day stuff, you'll just want to slink back some days and do nothing - but what if your main client/highest billing client has an issue, or wants 1:1 time, how do you react to that? What procedures do you ave in place for day to day matters as it's operations and makes business easier. So, change in the form of creating structure and procedure.

Resign when you have a good runway, your forecast is all green and you have a proven history of salary/income from this side project that rivals or exceeds your main day job. If you do - your time now becomes twice as valuable. I would of course try to see how long you can maintain double dipping working for someone else/yourself, but it'd come a point where you want the immediate time relief of just focusing on yourself/your project - this should be when you have a team in place and people to delegate and savings/cushion/runway of 2-4 years, be liberal or conservative, but, how you structure your personal day to day also matters highly. Time, becomes expensive.

The experience is great, and many people do it, from digital nomads (ugh, right?) to just talented people in general - there is no rule, per se that you must form a business where you live/reside, and many countries welcome the foreign influx of cash/assets in their country, but at that same time it also depends highly on that country's reputation, human rights, your rights, corruption and ease of doing business which are all recorded and known index's. Some country's have langauge and country barriers - China and Japan welcome foreigners to start corporations, but one is very friendly and has great programs for entrepreneurs with rights guaranteed (Japan) but suffer from culture and language barrier (Japanese, Hanko, Holidays, Politeness and I won't say dislike foreigners, but unless you have friends, can make some things harder.) vs another, China, that you have no property rights, ease of doing business is easy with cash, but wiring/fiscal currency controls, IP controls, and general distrust of media/government alongside culture and language barriers make it hard. Cheap labor though.

Taxation in Japan/CN is also pretty fun, but that's another topic I won't get into -- Estonia makes it sound easy too. Southeast Asia in general is also fun but it's a conversation worth having once you have a proven business model and history of revenue that a 20% reduction in taxes, matters. Because 20% reduction of $0 is still, $0.