[troydavis]

Regarding the question in the title:

1. I got as much experience spotting problems that I had and coming up with solutions to them as I possibly could. Build things, even tiny things, then see how well they solve your problem and how well they solve anyone else’s problems.

2. I had a fair amount of experience with the presales and sales process, and had a strong opinion how I’d want to purchase what I made. Try to charge money for something. Even if it’s just consulting services, going through the sales process with a handful of customers is incredibly helpful.

Finally… the golden handcuffs are a different story. https://news.ycombinator.com/item?id=17286939 and https://danluu.com/startup-tradeoffs/, if you’re employed at a very large tech company (with the compensation Dan described) and want to maximize your risk-adjusted/likely income, stay there. If you want to make something that no large company will pay you to make, a startup is probably the way to do that.

So… when you leave, your expected income will be less, not more. Only do this if you care more about creating something, or solving a specific problem, or testing your own skills than about maximizing risk-adjusted income.