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.

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.
Wouldn’t it be nice to earn money while not working? That money is called residual, or recurring, income. It's what can happen after you put a lot of time, effort and sometimes money into a job to continue to get paid for the work months or years after it's done. (Salary jobs are part of linear income. This income is directly related to the number of hours you work. If you work 40 hours, you get paid for 40 hours of work.) Once you set up your business to earn residual income, you continue to make money while doing other things – maybe even starting a new business to generate more residual income!
Those who can reap the benefits of residual income have typically put in an immense amount of effort and time in the beginning to be able to enjoy the rewards later on. Residual income, therefore, does not result in instant gratification. Those interested in earning residual income must have a lot of patience and determination to work as hard as necessary to achieve their ultimate goals of a long-standing income stream.
With sites like Wrapify and StickerRide, you can earn hundreds of dollars each month by simply driving around town. You’ll need to place an advertisement on your car and drive a certain number of miles every month. If you’re already on the road for work, travel, or school, advertising allows you to make extra cash without any extra time commitment.

A company called StreetShares helps mostly veteran small business owners (also some non-veteran owned) acquire capital for their business cash flow needs by providing loans. What’s really cool is that these loans are funded by investors. For a $25 minimum investment, all U.S.-based investors can earn a flat yield of 5% on their money by investing in StreetShares Veteran Business Bonds.
A new venture was started under the wing of Pacific Life Insurance company last year called Swell Investing. They’ve created investment portfolios to cater to the values of certain people. These portfolios contain a number of stocks that fit the theme of the portfolio such as green tech or renewable energy. Dividends received are automatically reinvested to help compound your wealth for now.
There is a specific tax definition of passive income, known as “passive activity” to the Internal Revenue Service. Passive income is any income you make without actively working or are materially involved. The IRS defines it as any rental activity or any business in which the taxpayer does not “materially participate.” Nonpassive activities, or active activities, are businesses in which the taxpayer works on a regular, continuous, and substantial basis.
When money is lent to a partnership or S-corporation acting as a pass-through entity (essentially a business that is designed to reduce the effects of double taxation) by that entity’s owner, the interest income on that loan to the portfolio income can qualify as passive income. As the IRS language reads: "Certain self-charged interest income or deductions may be treated as passive activity gross income or passive activity deductions if the loan proceeds are used in a passive activity."
I personally don’t care about being seen as rich – I don’t need the fancy house or cars. I just want to know that I can give up some or all work whenever I’d like to, and spend that time with my family without any financial pressure. I remember reading somewhere that “wealth is measured in time, not dollars” – and I believe that to be totally true. If I ever got a tattoo, that phrase would be highly considered to end up somewhere on my body.
When fully consistent assumptions are used to forecast earnings, cash flow, dividends, book value, and residual income through a full set of pro forma (projected) financial statements, and the same required rate of return on equity is used as the discount rate, the same estimate of value should result from a residual income, dividend discount, or free cash flow valuation. In practice, however, analysts may find one model easier to apply and possibly arrive at different valuations using the different models.
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There is also an idea that we should work to build a passive income asset and then sit on the beach relaxing for the rest of our lives. The truth is that most people would get extremely bored with this scenario and will be eager to find something to do. That’s why the world’s billionaires continue to work… they love what they do and it stopped being about the money a long time ago.
2. Real Estate: Real estate is #2 for one simple reason, leverage – using smart debt and other people’s money. When looking at real estate rents and the potential for income real estate provides, it is the trifecta of residual income. First, a home or rental property can appreciate, so capital appreciation is the first long-term benefit of owning a home. Second, rent. Other people are paying the mortgage, insurance, property taxes and maintenance while you own that piece of real estate. Third, tax protection. Rental income is taxed at a lower rate than ordinary income and you can depreciate real estate by taking a paper deduction on your annual tax return not to mention expensing the cost of mileage, mortgage interest, and updates to the property. Rentals done right can generate almost double what the stock market can in dividends and interest. The fourth and maybe most hidden, but important benefit is that over time rent’s rise, protecting your cash-flow against inflation, while your mortgage interest can be at a fixed rate potentially.
My favorite type of semi-passive income was rental property because it was a tangible asset that provided reliable income. As I grew older, my interest in rental property waned because I no longer had the patience and time to deal with maintenance issues and tenants. Online real estate became more attractive, along with tax-free municipal-bond income once rates started to rise.
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Case Schiller only tracks price appreciation of RE. RE as rental investment vehicle is measured primarily on rental yield or cap rate or some other measure. Price appreciation in that scenario is only a secondary means of growth, and arguably should be ignored as a predictor of returns when deciding on whether or not to invest in rentals. More important key performance indicators for rentals are net operating income and cash ROI. Appreciation, if it occurs, is a bonus.
Looking for ways to build financial wealth long-term without adding more work to your daily life? Residual income allows you to increase your fortune passively — meaning you’re earning cash while you eat, sleep, and brush your teeth. With the substantial increase of online platforms and opportunities, residual income is easier to achieve than ever before.
Owning property can earn you passive income for decades to come. Once you purchase a duplex, home, or apartment building as a rental property, you’ll earn a consistent monthly income with little work. Rent should cover your mortgage, taxes, repairs, and other expenses. You’ll continue to earn income by paying off your mortgage with the rent money and saving excess rental income.
I actually spent a year and a half working as an affiliate marketer (mostly selling drumming related products – lessons, kits ect). 5 years on and one of my one page sites (which I’ve not touched) still nets me about $150 a month. I won’t be retiring off that but only really now appreciate the reverse pyramid approach to entrepreneurship (working for nothing initially but later being paid without effort!)
Venture debt ($12,240 a year): The first venture-debt fund has returned almost all my initial capital, so I decided to invest $200,000 in the second fund. I took a risk investing $150,000 in my friend's first fund, so I'm hoping there's less risk in the second fund, given he has four more years of experience on top of his 12-plus years of experience running a venture-debt portfolio for another company.
Working as a nurse or a computer engineer for a salary are two examples of active income. In contrast, residual income is income from an investment that earns over the minimum rate of return. You get paid for work you completed once or are periodically overseeing. With residual income, you don’t have to be present or intricately involved to get paid.
The first application of residual income, the remaining money after debts are paid each month, is relevant when analyzing a person's financial status or ability to qualify for financing. The second application, the more widely recognized meaning of residual income, is money that is received on an on-going basis for work that is completed once. This form of income allows the recipient to generate revenue that is not based on time limits. Residual income is the foundation for wealth because it offers flexibility in earning and maximizing income. It also allows income to be generated long after the work has been done.

Investing your money is one of the oldest passive income strategies on the books. Investing in stocks (or funds of stocks) means that you are becoming a (very) partial owner in the company whose stock you own. When you purchase a stock, your expectation is that the value of the stock will either increase or decrease, and your goal is to buy low and sell high. (This is what everyone is shouting about on the floor of the NYSE in movies about the world of high finance).
I just can’t seem to get my head around creating my own online product. When you talk about it, you make it sound like its mostly just about putting in the time and plugging away at it. Problem is I can never seem to come up with any ideas for a site or product that seem remotely unique or compelling or that I have any special knowledge about. The stuff I do know about is pretty commodity type knowledge that can mostly be found on thousands of sites on the internet already. Any tips on discovering what your “unique angle” is? I mean, you have a pretty compelling and somewhat unique personal story of working on wall street and then walking away at a young age.
I just started out with Affiliate Marketing (idea # 8) and it is not as easy as people make out to be. For me, the hardest part so far, is learning Search Engine Optimization (SEO) and driving traffic to my website. I’m only 3 months into it, but I am confident that the site will begin to generate some incom., I have to give it 6-9 months, so we’ll see.

Online courses have exploded in the past five years. Experts and creators can now create video courses to teach others their craft. A course can be about anything that people want to learn. Friends of mine have created courses and say the amount of effort is similar to writing a book. But once its done and starts to sell, it’s a solid passive income stream.
The biggest surprise is real estate being second to last on my Passive Income Ranking List because I’ve written that real estate is my favorite investment class to build wealth. Physical real estate doesn’t stack up well against the other passive income sources due to the lack of liquidity and constant maintenance of tenants and property. The returns can be huge due to rising rental income AND principal over time, much like dividend investing. If you are a “proactive passive income earner” like myself, then real estate is great.
It’s a (mostly) short term, higher risk, higher reward place to invest cash that has a low correlation with the stock market, but is far more passive than buying and managing properties, has more opportunity for diversification than private placements (minimums of 5-10K, rather than 100K), and most of the equity offerings (and all of the debt offerings) provide monthly or quarterly incomes. Unlike a REIT, you can choose exactly which projects you wish to invest in.
Personal finance software can go a long way in helping you to take control of your money and meeting your financial goals. It’s important to note, however, that some focus more on budgeting and expense tracking while others prioritize investing portfolios and income taxes. Explore several different programs and read reviews to find the one that’s right for you.
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