We are going to start with 1.5 years of all spending needs in cash. We will draw 1800 to 1900 per month. We will add to this from the index funds by taking a portion of the gains in good years to supplement. This is the total return portion of the equation. Obviously, if stocks decrease drastically over a 5 year period, then I would have to reload by selling some of the ETF holdings.
It’s easy to think as passive income as money earned while sitting on a beach sipping mojitos, but there is lots of work involved, says financial coach and retired hedge fund manager Todd Tresidder. If you’re worried about being able to save enough of your earnings to meet your retirement goals, building wealth through passive income is a strategy that might appeal to you.
The U.S. Internal Revenue Service categorizes income into three broad types, active income, passive income, and portfolio income.[1] It defines passive income as only coming from two sources: rental activity or "trade or business activities in which you do not materially participate."[2][3] Other financial and government institutions also recognize it as an income obtained as a result of capital growth or in relation to negative gearing. Passive income is usually taxable.

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We’ve discussed how to get started building passive income for financial freedom in a previous post. Now I’d like to rank the various passive income streams based on risk, return, and feasibility. The rankings are somewhat subjective, but they are born from my own real life experiences attempting to generate multiple types of passive income sources over the past 16 years.
If you need cash flow, and the dividend doesn’t meet your needs, sell a little appreciated stock. (or keep a CD ladder rolling and leave your stock alone). At the risk of repeating myself, whether you take cash out of your portfolio in the form of “rent”, dividend, interest, cap gain, laddered CD…., etc. The arithmetic doesn’t change. You are still taking cash out of your portfolio. I’m just pointing out that we shouldn’t let the tail wag the dog. IOW, the primary goal is to grow the long term value of your portfolio, after tax. Period. All other goals are secondary.
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.
Love your articles. I think everyone is very different as far as how much passive income they need to meet their goals. I’ve read a lot of your articles and really enjoy your thoughts. I have a masters in finance and understand the math of keeping the debt but my emotions are such that I need to try to finish off paying off my last debt (mortgage) in the next two years. At 34 and only worth 525k I’m doing better than a lot of folks my age but it will be difficult for me to catch up in the passive income game without leverage. That is the main reason I recently created a website to try to bring passive income opportunities in my area to me.
Real estate is the obvious choice if you are going to make money on your money. I personally am not at the point where I can do any of this in a meaningful way BUT my parents are and they now own a couple homes outright and are collecting income from them to power their retirement income. It makes a lot more sense for anyone that has a chunk of cash sitting in the bank and are planning on slowly drawing from it because you technically still have all that money in a property (or multiple properties) and can sell them if you really need the lump sum of cash but you’ll earn great interest payments until you do that.
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