P.S. I also fail to understand your fascination with real estate. Granted we’ve had some impressive spikes along the way, especially with once in a life time bubble we just went through. But over the long term (see Case Shiller real estate chart for last 100 years ) real estate tends to just track inflation. Why would you sacrifice stock market returns for a vehicle that historically hasn’t shown a real return?


For instance, a business owner who works in the company she or he founded would have to pay an extra 15.3 percent in self-employment payroll taxes compared to someone who merely had a passive interest in the same limited liability company who would pay only income taxes. In other words, the same income earned actively would be taxed at a higher rate than if it were earned passively.
Another way to generate passive income is to invest and be a silent partner in a business. This is very risky, but with risk comes the potential for high returns. For example, several years ago both Lyft and Uber were looking for private investors to invest in their companies. Today, they are worth billions - but you as an investor would only reap that benefit if they go public via an IPO, or get acquired. So, it's risky.
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Sam…just read this article and I want to say that this is the best posting on passive income I have ever read…in a blog, article, or book. Thanks for making a difference and being an inspiration as to how it can all be accomplished. One of the great benefits of the internet is that people are willing to share their stories and experiences with each other online. If we had this when I was working professionally (20-40 years ago), it would have saved me from making some rather poor financial decisions that affected my retirement income. In a way, the internet is making up for the loss of financial security in the loss of The Defined Benefit Plan for retirement. Bravo!
Whether you take a “distribution” (aka free-cash-flow) in the form of a dividend, interest payment, capital gain, maturing ladder of a CD, etc, you are still taking the same amount of cash out of your portfolio. Don’t fall for the trap of sub optimizing your overall portfolio’s performance because your chasing some unimportant trait called “income”.
Thirst for income is likely to continue with interest rates expected to stay low, keeping government bond yields low for longer and their valuations unattractive.  Looking past bonds, the prices of high-dividend shares are historically high, which limits the likelihood that their dividends will rise markedly from here.  Striving too high for an income target tends to push your portfolio further out on the risk spectrum.
Taking Paid Surveys at Home: I was skeptical, at first, until my 17 year old son starting making money at home taking paid surveys. Companies desperately want your opinion, and they are willing to pay for it. The trick, of course, is knowing where to find the paid surveys that pay the best. One of the most popular and legitimate survey sites is Swagbucks. Not only can you make money taking surveys, but you can also make money by watching videos and even surfing the net. They also offer significant cash back for online shopping.
Who cares, especially when very conservatively, the ultimate passive income includes a six digit or more base lease, plus an estimated additional six digits or more for rate increases and another six digits for more for various smaller and one bigger technology increase at 25 years. All four (base, rate, smaller and mega technology increases) combined, certainly could yield much more depending upon inflation, rate increases and technology increases?

Those who choose to focus on passive income will need either family money, funds from investors, or the nerve to borrow large sums by taking on debt to fund the purchase of assets. The easiest to understand is someone who takes out substantial bank loans to build an apartment building or buy rental houses. Although this can turn a very small amount of equity into a large cash flow stream, it is not without risk. When using borrowed money, the margin of safety is much smaller because you can’t absorb the same degree of setback before defaulting and finding your balance sheet obliterated.
The challenge I’m facing and, I know it’s a good problem, is that the SF real estate has shot up about 35% in the last couple years. I’m sure you’re experiencing the same thing! So as the net worth is rising, the yield on the total portfolio is going down. Right now, it seems the only way to increase the passive income will be to raise the rent in December and to invest some of that cash in stocks, which I’m nervous to do in this market. Current allocation:
Andrew Rafal, Founder and President of Bayntree Wealth Advisors in Arizona, recently told me about his push to get clients to diversify their income streams. The Great Recession feels like an eternity ago now that the economy is looking up, he says. The job market is strong and consumer confidence is through the roof. As a result, it’s possible people are getting a little too comfortable.
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