Quote Originally Posted by LDAHL View Post
I seem to recall you once mentioning that during your transitional period you decided to give away a considerable portion of your net worth. As someone not particularly burdened by substantial wealth, I'm curious about how you determined how much to keep and whether you had a formal plan for converting assets into income.
I was a chicken. I kept enough that if I kept it in cash/low-yield-but-safe investments, I likely wouldn't even spend through the pile. The rest into a charitable instrument that I control, and that *can* pay salaries to its directors for their keen and prudent management/investment work. So if things went really south I could pay myself a salary, as long as it was "reasonable".

As far as a plan for assets-to-income, I invest in boring stocks that pay dividends, boring bonds that pay interest, boring real estate that produces rents, boring loans that produce interest, and sorta-boring businesses that produce profits.

I didn't strive to maximize my upside so much as to limit my downside so that I knew I'd always have a roof over my head and rice & beans to eat. If I had more expensive tastes (jets instead of Cessnas, huge yachts instead of tastefully-small yachts, ...) I might have kept more.