I use the same technique. It has been working very well for me so far. I'm not rich, but lets say I will never have to worry about money again for the rest of my life, and neither will my descendants for the next 6 generations.
but you're extremely wealthy so youre not like normal people. you can afford to lose hundreds of thousands of dollars starting companies and its just a tax write-off for you. That amount of money would destory most peoples lives.
Never forget how privileged you are. you seem you have forgotten.
Personally, I think threads like this and the mentality of HN readers that causes threads like this to get created is the main reason why employement in this industry has gotten so horrible.
Everyone is only interested in the very best and only wants to work for the biggest companies with the best perks. It opens the door for manipulation and these companies have for YEARS been taking advantage of workers in this industry.
I have several friends who have made out really well from their time in the tech industry. Most of them took more options instead of higher salaries. Now, most of my late-20s friends are buying houses and retiring (or starting their own companies) on the fortunes they have made.
Just because you personally haven't had a windfall doesn't mean it doesn't happen.