I enjoy how you lay out real numbers. A lot of people wouldn’t do that. While you admit that you are somewhat conservative, I think the $1M in CD’s is just too conservative. Assuming you don’t need the cash flow now (which you say you just save anyways) then all that could be invested for potentially higher returns. For example, what if you bought San Francisco real estate along the way instead of CD’s. Or, an SP500 Index fund. I bet your average return would have been higher than 3.75%. Sure you could lose it, but the point is if you don’t need the cash flow now, you should try to increase that nut as high as possible until the day you actually need it. Your nut could be $5M right now if you had invested in asset classes other than CD’s for the last 14 years. Don’t get me wrong, you have done far better than me, but I guess I would take a little more risk if you don’t rely on that cash flow.

Everything passive first takes active energy. The time to put in the effort is when we are young and not ravaged by disease or burdened by family obligations. I remember being able to snowboard from 9am until 4pm every day for a year. Now, I’m lucky to last from 11am until 2pm without wanting to go to the hot tub and drink a bucket full of beer! If we can appreciate how lucky we are when we are young, we’ll be able to maximize our vitality and live financially freer when we are older.
This is separated intentionally from “information products,” because here I’m referring specifically to secondary value creation. If you can write a popular blog and get people reading it, you can sell ads. Alternatively, if you write a niche blog about vegetarian, gluten-free cat food, you can use special affiliate links to different websites, and get paid when people buy through those links. There’s lots of great blogs making tons of money doing these two things (I know of people making millions referring credit card signups), but please note that unless someone is writing and distributing the content for you, this is not passive income. It takes a lot of work to drive traffic. Some of the smarter people I know doing this have hired content writers and set up a bunch of sites, but they invest a TON of time on SEO, finding the right topics, etc.
Truebill is an app that helps you save money by identifying recurring subscriptions and other bills and helping you cut costs by negotiating better rates and fees. One of their partnerships is with Acradia Power, which has the potential to save you up to 30% on your electric bill. It searches for better power rates in areas where competition is allowed, and it locks in the better prices for you.
When a taxpayer records a loss on a passive activity, only passive activity profits can have their deductions offset instead of the income as a whole. It would be considered prudent for a person to ensure all the passive activities were classified that way so they can make the most of the tax deduction. These deductions are allocated for the next tax year and are applied in a reasonable manner that takes into account the next year's earnings or losses.
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