By the time a startup can pay you serious base cash compensation, I don’t think it’s likely they could also pay you serious equity compensation as an individual contributor. There’s no lottery ticket there, just trade offs. A lottery ticket is usually huge payoff or nothing. $500k or less, even a million or less doesn’t really sound like a lottery ticket (not to downplay how life changing that payoff could be).

Philosophically the lottery ticket scenario is your own startup or early startup employee, where your rationalization is >$10 mil or bust. Either certified “seriously rich” anywhere in the world or you just wasted your time. That’s a asymmetric payoff of a lottery ticket

I mean it depends right? Even employee 1000 at Google made many millions. And it’s rumored that the Lyft IPO made several hundred millionaires.

Hell, a friend of mine made about 1mil at IPO (on paper) and she’s a tech support manager. Not sure how early she joined but always said the cash was her highest salary ever.

Living and working elsewhere with the wages of the region reduces expenses and opportunities; but the wealth of educational resources online [1][2] does make it feasible to even bootstrap a company on the side. Do you need to borrow money to scale quickly enough to pay expenses with sufficient cash flow for the foreseeable future?

Income sources: Passive income, Content, Equity that's potentially worth nothing, a backtested diversified portfolio (Golden Butterfly or All Weather Portfolio and why?) of sustainable investments, Business models [3]; Software implementations of solutions to businesses, organizations, and/or consumers' opportunities

Single-payer / Universal Healthcare is a looming family expense for many entrepreneurs; many of whom do get into entrepreneurship later in life.

Small businesses make up a significant portion of GDP. Small businesses have to have to accept risk.

There's still opportunity in the world.

[1] Startup School > Curriculum https://www.startupschool.org/curriculum

[2] https://www.ycombinator.com/library

[3] "Business models based on the compiled list at [HN]" https://gist.github.com/ndarville/4295324

From "Why companies lose their best innovators (2019)" https://news.ycombinator.com/item?id=23887903 :

> "Intrapreneurial." What does that even mean? The employee, within their specialized department, spends resources (time, money, equipment) on something that their superior managers have not allocated funding for because they want: (a) recognition; (b) job security; (c) to save resources such as time and money; (d) to work on something else instead of this wasteful process; (e) more money.

I’d you are going to start something on the side, carefully read your current employment agreement, particularly the part about IP assignment. Most Silicon Valley companies I’ve worked with, including FAANGs, claim ownership of everything you produce, inside or outside of employment, at home or in office, using their equipment or yours. You don’t want to lick into a unicorn idea and have your former employer’s lawyers send you that letter...

Unusual data point (I'm not sure if South African practice is applicable elsewhere) , but most bigger corps I've worked at have provided a mechanism to declare external interests, pending management approval, to work around these global clauses.

On paper any IP would be default belong to the Corp, but after some discussion/negotiations with your line manager and his higher-ups, you could do the paper work to declare.

Are these actually enforceable?

It probably doesn’t matter in practice. They will have more lawyers and more money to burn on legal process than you. Who will go bankrupt first fighting a legal battle between you and, say, Apple?

In practice, I don't think I've ever seen a SV example of that kind of litigation from garage development of IP. Maybe I've just missed them?

Theft of IP from one company to a new company on the other hand there are multiple public examples of.

The only time they'd actually sue is if you made something worth money. in that case, there's a good chance you can get investors to pay the lawsuit.

Investors would check if you were subject to an IP assignment clause in your employment contract prior to investing. It's part of basic due diligence. They would then most likely pass on the investment.

It does matter in practice in California.

If its "related" to your employers business yes - unless you agree a variation of the contract.