8% ROI is unrealistic, but a 2-4% is certainly possible especially with municipal bonds and insurance annuities. The former are also exempt from federal taxes,

8% ROI is unrealistic, but a 2-4% is certainly possible especially with municipal bonds and insurance annuities. The former are also exempt from federal taxes, state taxes (if you live in the same state) and even local taxes (if you live in the same city). Both have guarantees against inflation (at the cost of lower yield) . Nonetheless, I do think the is somewhat overrated. If I had fuck you money, I'd... write code, read books and papers. I'd have more freedom on how I write my code during working hours (and it's important not to understate importance of that, but the more senior you get, the more choice you have in what you work on what tools you use), but I'd also not have the focus that comes from working on systems that solve actual problems that individuals and organizations have; nor would I be solving these problems at scale that makes them much more interesting. On the other hand, I'm pretty confident that if I were to spend my time chasing a big payoff I'd be working on problems that are far less interesting and more frustrating (which is almost axiomatically why these problems have the payoff). There's very few early-stage startups doing systems programming (and I'm speaking loosely here i.e., beyond just operating system kernels and file systems). For web companies systems programming only becomes needed as a scalability becomes a problem (in most cases it never does). The idea that may be I'll be able to go back to doing what I enjoy most of the time if the business succeeds won't be enough to drive me: I already do that (perhaps that's why so few "home run" startups have come out of Google?) Keep in mind that while stock options after product/market fit (pre-IPO startups, public companies) account for only a tiny percentage, the chance of a payoff is much higher (which, again, is why it's a tiny percentage: you're no longer taking a risk). That payoff is certainly no fuck you money (except in rare cases e.g., Google in early 2000s), but it's often sufficient in terms of giving you more freedom e.g., to go back to school for a Ph.D. Were I to have a vision for a business (rather than a science project, which most of my ideas have been) based upon interesting technology (i.e., not a website) I'd certainly consider pursuing it, but even then I'd have no illusions: I suspect, I'd spend more of my time doing what I don't like (general business operations) than what I do (coding); it would be the vision of bringing forth new technologies that solves real problems that would let me pull through that (as opposed to pure research or solving business problems with well known existing technologies) .