Anthony, nice setup! To your question about the rental mortgages, you haven’t said what interest rate you are paying. As a start, if you are paying more than the risk free rate (Treasury bills) which you probably are, then a true apples to apples comparison would be yes, pay off the mortgage. But, if you are comfortable taking more risk, you have other options to invest in which you *hope* will yield you more over the coming years. You also didn’t say whether the rentals generate net income and if so, how much? What is the implied rate of return on the equity you have invested in them? If you pay the mortgages off, you’ll have even more equity tied up, will the extra net income make that worthwhile? Maybe you should use the money to buy more rentals instead, if purchase opportunities still exist in your town. … this is less of an answer than a framework to analyze the decision, hope it is helpful.
I really enjoyed how you listed all of the reasons to build passive income streams as well as the framework. You also made an interesting point about freelance writing on how the more skilled writers want to keep posts for their own website. Good insight because freelance writing is something I’ve been looking into for income recently. Also, it’s amazing what you’ve been able to accomplish with your blog over the past 6 years. It’s so motivational to see the success of Financial Samurai. I’m not in a place to afford any consulting, but, I wish I could pick your brain or get mentored by a successful blogger such as yourself…Not trying to blow smoke lol. It would just be so great to have someone who’s done it provide guidance around the direction of the blog, ways to earn, and on the general concept. Always enjoy your posts. Thanks for sharing :)
Investing in Index Funds – I use Vanguard for this, but there are several reputable sites out there that allow you to do the same thing.  It’s a good way to invest excess cash that you don’t need now and use it to diversify your portfolio.  I’m not going to make a specific recommendation here, but Vanguard does have a page that will make a recommendation to you based on your risk tolerance.  This is generally going to require more up-front money than Lending Club (probably $1,000+), but if you have the money, it’s something to consider.
Leveraging the internet to create, connect, and sell is something every creative person should attempt to do. The only risk is lost time and a wounded ego. You can start a site like mine for as little as $2.95 a month with Bluehost and go from there. They give you a free domain name for a year. Forget all the add-ons. Not a day goes by that I’m not grateful for my site.
Inspired by you, I started a tax/personal finance a month ago. I figured if it works out, it will create a good side income for me. If not, at least I can use the blog to build my brand as a tax lawyer. Other than that, my current investment portfolio is heavily focused on index funds because of its historical performance and tax & cost efficiency. Right now my dividends income every year is about $14,000. I also have a good amount of unrealized capital gains every year from my investment, though I don’t count the capital gains as my passive income as they are paper gains, at least for now.
Real-estate crowdfunding ($9,600 a year): Once I sold my SF rental, it was natural to reinvest some of the proceeds into real-estate crowdfunding to keep sector exposure. I didn't invest a lot in some of my favorite real-estate investment trusts because I felt a rising interest-rate environment would be a stronger headwind for REITs. But if I could be more surgical with my real-estate investments by identifying specific investments in stronger employment-growth markets, I thought I could do better.

I remember seeing a number of my co-workers get laid off in 2008 and many of them had only worked for the one company. They had mortgages to pay, colleges to pay and families to support and they were scared out of their minds for what they would do next. After watching that happen, I vowed that I wouldn’t suffer the same fate. It’s one of the main reasons I started my own company. I tell people now that instead of one boss (i.e. one company), I have hundreds of bosses and it makes me feel more secure about my longterm prospects.


Don't mistake passive income with zero work. It's still work, it's just that your income is not directly tied to the hours worked. Anyone who owns rental properties knows that it's considered passive income but there is quite a bit of work involved. The work is front heavy but if you are lucky, you can collect rental checks without incident for many months before having to do work.
That's odd, because lot of these questions are actually pretty easy to answer. The IRS is good about publishing the data. Given that – and given the recent interest in personal income inequality, I decided to write a little bit about the different kinds of income people report on their tax returns. A longer paper – Sources of Personal Income – is here, but for a brief overview, you might want to check out the top ten sources of income:
This one may seem simple, but that’s only because it is. If you were to move your savings from a traditional, brick-and-mortar bank with a low-interest rate and into a high-yield savings account online, over time you can make a surprising amount of extra cash. Online banks are FDIC-insured just like the traditional brick-and-mortar institutions, so your money is just as safe.
These days, low-risk bond yields aren’t enough to meet most income needs. When investing in bonds, the income typically comes as coupon payments – contractually guaranteed interest payments at predictable intervals.  There are many kinds of bond income available, so you must strike a balance between reaching for higher income (yield) and limiting risk.
Add Leverage (Mortgage) and you greatly increase the ROI especially from the perspective of using Rents (other peoples money) to pay down the mortgage and increase your equity in the property over time. At this point then yes price appreciation is secondary bonus and we have an arguement of how and why Real Estate can be better than Growth Stocks in some scenarios and for some investors.
Thus, it's easy to dream of money just arriving, without our having to clock in to earn it. Fortunately, passive income streams don't have to be a dream. There are many sources, with examples including REIT dividend income, residual money, real-estate investments, interest, and other income-generating assets. Here's a look at 15 of them -- see which opportunities could work for you.
However, under certain circumstances, payment for personal services performed in the United States is not considered income from sources within the United States. For example, personal services performed by an independent nonresident alien contractor specifically exempted by a tax treaty. For more examples, see the Pay for Personal Service section in Publication 515, Withholding of Tax on Nonresident Aliens and Foreign Entities.
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