As we’ll discuss, passive income opportunities are usually limited-time only, and honestly, over half of what you try won’t work. Diversification is your friend. Having many sources of income — at least 7 including your “day job” — is an important hedging strategy. Personally, I have been working at it for a long time, and I’ve had many failures in trying to build my portfolio. I’ve done a few apps for BlackBerry (come on, it was 2009), contemplated writing a book, started a bunch of blogs and forums, and joined countless affiliate programs. Here are the ones that are currently working right now.

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."


Lending Club is a platform where you can lend your money to other people. You’re the bank. Each note is only $25, so you can invest $1,000 and lend money to 40 people. There are many grades of loan (from safest to riskiest) and investors earn, on average, between 5% and 7% annualized returns. For more information, check out Investing and Making Money with Lending Club Peer-to-Peer Lending and my real money Lending Club Portfolio.
In February 2007, Pat Flynn was working at an architecture firm making $38,000 a year. He mulled boosting his earning power by getting an architecture license, but the process would likely take six to eight years. When he heard about getting a credential in sustainable design and environmentally friendly building called Leadership in Energy and Environmental Design (LEED), he decided to go for that, as no one in his department had it. The one problem? The exam was so challenging, just one-third of test-takers passed.
I will share what we did, because it’s an incredible success story. We used an existing tax loophole where if you sell your primary residence (after having lived there at least two years) you get to keep your profit tax-free. So, we stair-stepped. We bought house after house, at least two years apart, used the profit money to pay down on the next house (so on and so forth, yadda yadda) building up equity as we went along… and now, we own a $600,000 house debt-free. And now we are using our paid-off home as leverage to borrow money to buy commercial buildings to rent out. I like commercial because it’s a BUSINESS transaction… kids, pets, other wear and tear that you see with residential rentals is nonexistent. People take care of their business space much better than residential. You have to be in a good area for renting out commercial – a thriving business community – to make this work. But that’s how we “made it”, and though it took 15 years, we will have residual income to take care of us when we’re old enough to retire. People made fun of us for moving so much, but who’s laughing now? 😉 Oh, and our child only had to change schools once (and we wanted to anyway) because we stayed in the same general area as we moved around. We were careful not to disrupt his life too much.
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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.
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.
Stock dividends: Some stocks, especially stocks from big corporate standouts, pay dividends to shareholders based on the number of shares they own, and the percentage of the stock price on the dividend date. For example, if a company pays out 3% on a stock that's trading at $100 per share, you'll earn $3 for every share of that stock you own. Add it up and that can be good take-home pay as a passive investment.
Absolutely Federico. I still invest in real estate but no longer carry the misconceptions that it’s passive income. Fortunately, I’ve held my real estate properties long enough that they cash flow even after paying for management but it was a lot of work in the beginning. Real estate is a great investment but passive income investors should look to REITs and other investments rather than direct investment.
Dividend Income: Dividend income is wonderful because it is completely passive and is taxed at only 15% if you are in the 25%, 28%, 33%, and 35% income tax bracket. If you are in the 39.6% income tax bracket you will pay a 20% tax on your dividends. My dividend income portfolio mainly consist of dividend equity and bond ETFs such as DVY, VYM, MUB, TLT, and IEF. Total stock and bond income is a little over $100,000 a year due to a heavy accumulation of stocks and municipal bonds after selling my house.

We usually think of Craigslist as a place to buy and trade random stuff, but Craigslist can actually be a great opportunity to sell your services online to an active and engaged audience. Simply check the “jobs” section and “gigs” section for specific cities and see if anything matches your skills. The great thing about Craigslist is that it is one of the highest converting traffic sources on the internet (think active buyers) which can mean more opportunities at higher pay.
For those of you who don’t want to come up with a $220,000 downpayment and a $900,000 mortgage to buy the median home in SF or NYC, who don’t want to deal with tenants or remodeling, and who wants to not do any work after the investment is made, check out Fundrise. They are my favorite real estate crowdsourcing company founded in 2012 and based in Washington DC. They are pioneers in the eREIT product offering and they’re raising an Opportunity Fund to take advantage of new tax favorable laws.
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Creating passive income is one of the most important steps towards retirement. Passive income is money that comes in without any work from you. Stock dividends, rental property income, interest on notes are all forms of passive income. Truly passive income is almost impossible to achieve, because every investment involves some sort of work. Stocks are fairly easy to buy, but still require research, while real estate is more difficult to buy, but can produce much higher returns.
If you’ve ever thought to yourself, “I wish there was a product that did this,” then invent it! Create a product, medical or otherwise, and sell it as a company or get royalties for it. It’s not impossible to figure out, I have many friends who have taken a concept to market. Don’t overlook an invention as a fantastic means of attaining passive income.
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