> And $10M would require some up-front management and ongoing maintenance to develop an index-tracked revenue stream from it. Buy $5M of VOO and $5M of VTEB or

> And $10M would require some up-front management and ongoing maintenance to develop an index-tracked revenue stream from it. Buy $5M of VOO and $5M of VTEB or BND. Send dividends to your bank account. When your bank account is over the FDIC limit, buy more of whichever fund has less $. Dividend yield on VOO is about 1%, bond fund is about 3%, approximately $200k/year from dividends, but if that's not enough, sell from the fund with more $ as needed. If you go with VTEB (tax exempt bonds), you'll have a very low federal tax with $50k of mostly qualified dividends and $150k of mostly tax exempt interest; if you go with BND, you're still only looking at about 20% effective tax rate Single, or 15% married filing joint. Probably check with your insurer and get an umbrella policy for $5M+ cause they're cheap and you don't want to get a judgement and lose out on the easy life. Send me a check for about $10k a year as a reminder of how much work I did for you right here in the open :P (j/k, I'm not a financial advisor, I can't take compensation for this). You could do something fancier like optimizing the tax-exempt vs regular bonds or think about your preferred stock/bond ratio or exotic investment options to enrich the advisors, but $10M is enough that anything safe (80:20 to 20:80) will work unless you overspend, and it's not enough that getting a little more return is going to let you keep a private jet (better to charter anyway). On the OP's question. I kept working while I was having fun and then worked on cleanly transitioning things out so I could feel good about leaving without loose ends. I went back to work part time in order to insure domestic tranquility. :P You can do a lot with computers without a job/company/product, but IMHO, optimizing things is more fun when you have a lot of users and you can see the results, so that kind of leads towards working at least a bit, even if you don't have to.