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.
At age 55, I own high-end rental properties (near the beach) and commercial buildings servicing the medical industry. I was widely criticized during my career for not living up to my income; that is, buying big homes with many fancy cars. I married a great woman who understood that saving and investing today meant a better lifestyle and more freedom tomorrow. Our passive income is half of my active income from sales, but my net worth has increased substantially. We are both happier and healthier than we were in the high-stress pressure cooker of franchise sales. The naysayers have become converts to the concept of passive income, but they have locked themselves into a “big hat, no cattle” lifestyle. It has been a great ride!
One thing I’ve realized is this: It’s FAR easier to work for an employer than it is to develop durable passive income streams for the average person. Why? Because working for an employer in a place that “needs” you means that it’s possible to show up and give a 50% effort. You can show up, put in your time, go home, have a beer, watch TV, and rinse and repeat all without REALLY having to put in the effort.
One of the great things about generating passive income via rental properties is the ability to buy properties throughout the country instead of just in your generally locality. Because you will hire others to manage, maintain, and repair the property, you don’t have to be in the same location and can maintain passive ownership from virtually anywhere. That gives you the ability to better choose rental markets where you stand the best chance of profiting the most due to lower local and state property and business taxes.
This is the best post I’ve seen on passive income streams. I’m similar to you in that I worked in IBanking for a few years but wanted out. My approach is a little different, instead of starting with the CD’s, I’m trying to build up my net worth with riskier asset classes such as stocks and real estate to get the benefit of compounding. Then, as I approach my retirement year goal, I’ll start moving them into CD and bond ladders. In theory at least, it’s best to have the highest net worth just before retirement, then convert them to risk free passive income. You’re method is more patient and probably more practical than mine. I guess I’m willing to take more risks.
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.
Agreed but I might consider a blended portfolio of large and small cap stocks using low cost mutual funds (I found a fidelity large cap fund FUSVX with a net expense of .035% that has also delivered 17%+ YTD gains, some are dividend some are growth stock in the fund) UNLESS you’re close to retirement. This way you get the growth upside on small cap paired with the stablilty of some large cap stocks while maintaining balanced ricks.
In Eric Reis’s The Lean Startup, a fantastic book about how today’s entrepreneurs and startup companies are approaching the way they create and innovate, Eric talks about how vital it is to use validated learning and scientific experimentation to be able to steer a company in the right direction. In other words, to use customer feedback and quantified data analysis (of real, non-vanity metrics) from a minimal viable product to make decisions and pivot a business one way or another.
There are three main categories of income: active income, passive income and portfolio income. Passive income has been a relatively loosely used term in recent years. Colloquially, it’s been used to define money being earned regularly with little or no effort on the part of the person receiving it. Popular types of passive income include real estate, peer-to-peer (P2P) lending and dividend stocks. Proponents of earning passive income tend to be boosters of a work-from-home and be-your-own-boss professional lifestyle. The type of earnings people usually associate with this are gains on stocks, interest, retirement pay, lottery winnings, online work and capital gains. 
Like we said above, there’s nothing passive about this, but if you can create another type of asset — a system for selling products — then it is. One example is to write a book, and use Amazon Fulfillment Services to automatically print and ship it every time you sell a copy, depositing the money in your account. Another example is Tim Ferriss, who hired overseas assistants to handle everything at BrainQuicken, from the marketing to the reordering. With drop-shipping (having the manufacturer ship directly to your customer), this has become easier, but you should know that it’s still a good bit of human labor to advertise, handle customer service, etc. But, it’s a good option, and you can experiment with automation and delegation as you go along. If you want to know more about this, read The Four Hour Work Week already!
The much loved model for bloggers and content creators everywhere and for a good reason…it’s pretty easy to write a 60-80 page ebook, not hard to sell say $500 worth a month through online networking, guest posting and your own SEO optimized blog, and well you get to keep a large whack of the pie after paying affiliates.  Hells yeah!  Continue reading >
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