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.
I agree mostly with the real estate advice. I’m looking for ways to take advantage of the condo I own to get up the rent from ~$0.90/ft to the $1.2-1.5/ft that seems more like the range in the same area. I’d have to put in a bit of capital (probably 10k on the low end for just the basics up to 40k if I wanted to remodel the kitchen and 2 bathrooms up to par with the area), so the return is likely there if those upgrades warrant $1.30/ft (given the unit is larger than most 2br/2ba in the area).

Another way to reduce the work needed when buying rental properties is to buy turn-key properties. Turn-key rentals are already repaired, already rented and already managed by a property manager. Buying a turn-key rental property is as easy as talking to a turn-key rental property about what they have in inventory, picking one and setting up closing. I would still complete due diligence on any turn-key rental property provider to make sure they are a good company. I am considering buying a turn-key property myself and I discuss the process here.
Flynn has created many different products. While his LEED exam is what got him started, he has both earned a commission from selling other people’s products and offered a commission to others who would sell his wares, and also recently created his first software, SmartPodcastPlayer.com, after realizing that most online podcast players offered only the basic stop/start/volume features. He hired a development team to create a superior one, which was a success from day 1. “We sold out 250 beta licenses in less than 24 hours, because I was addressing a need but also, I had built up an audience and trust with them … When you build that amount of trust with your audience, whatever you come out with, they will love.”
I run a real estate team that sells houses. I have eight people on my team and many of them are real estate agents. I also have assistants and contract managers who help with paper work and the ins and outs of the business. I sell houses myself (mostly REO and HUD), but many houses are sold without me doing any work. I get a part of those commission checks, because I set up the team, offer training and help my agents succeed. My business is not truly passive, but if I want to go on vacation for a couple of weeks I still have money coming in without me doing any work. There are thousands of business that can be started, but I think becoming a real estate agent is a great way to become an entrepreneur.
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.
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.

For someone my age, I have an extremely low risk portfolio of mutual funds, foreign currency, and bonds. It’s made a bit more risky by my recent exposure to cryptocurrency, but that’s the only “high risk” activity going on here. Nothing exciting, but it pays some nice dividends and beats the hell out of keeping money in a savings account. This is a way for me to hedge against the risk I incur by angel investing in startups.

Crowdfunded real estate companies like Fundrise are similar to today’s peer-to-peer lending companies. Like Lending Club and Prosper, they offer a platform that matches real estate investors with investment choices. They help people looking to invest money in real estate in a passive manner. Also, investors can avoid bargaining with sellers. No need to get involved in the transfer of ownership and management of those properties either.


I invest about 5% of my pre tax income in 401k that my employer matches. Have close to 70k in cash in checking. Also,I liquidated around 40k in my 401k and not sure where to invest that in (bonds vs stocks) because of stocks trading at record high. Have a rental property that is paying itself now and I will pay off the mortgage completely in 5 years. My immediate concern is the cash in checking acct that’s not doing much. Thanks for your reply and appreciate your work. I am learning a lot
I want to develop a passive income stream in the next 4 years, nothing grand, maybe an extra 500-1000 dollars a month, but I’m not sure how to go about it so I was wondering if you had any tips. I’m so-so as a writer, and am currently finishing up my second book (just write as a hobby), and in the past made about 30-50 dollars an hour as a free lance writer but that was a couple of years back, it was only for about 10-20 hours a month, and the gig just dried up. I just got particularly lucky with that. I’ve tried online poker as a means in the past, and which I learned A) was not passive income but hard work and B) I have an addictive personality which resulted in me losing the 4g I earned in 6 weeks over the span of 72 hours so that’s out of the picture. I also partook in some illegal selling of things when I was younger, but being a little older and wiser the risk-reward ratio for possibly ending up in Jail just doesn’t match up. I tried making three businesses (dog walking, house cleaning, and personal assistant) and while those all were succesful to varying degrees and earned me about 15-25 dollars an hour, they weren’t mobile and quiet honestly I don’t have the time to be a full time dog walker or run a house cleaning operation seeing as I’ll be in school, work, and athletics.
If you’re worried about launching a new product, and think you might need some feedback to make it really good, Flynn recommends “pre-selling” an idea — for instance, offering a limited number of spots or seats into, say, a course you create and giving the test group specialized attention so you can see how to improve the content. Once it’s revised (or, if it’s software, once all the bugs are removed), you could open it up to your whole audience.
Who doesn’t like some down and dirty affiliate fees?!  Especially if you realize it can be even easier to make money this way than with an ebook.  After all, you simply need to concentrate on pumping out some content for your own site and getting the traffic in, often via Google or social media.  Unsurprisingly, most people can enjoy their first affiliate sale within 30 days of starting a blog.  Continue reading >
Dividends made sense 40 years ago as a relatively simple rule of thumb, but after all the work done by John Bogle with index investing, and academics with Monte Carlo sims and the 4% rule, dividend investing just isn’t the simplest, cleanest way to invest or receive passive income anymore. It’s actually significantly more risky compared to index investing, because dividend companies are a much smaller share of the total global economy compared to the broader indices.
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!)
When you have several rental income properties, you make your money two ways. The most obvious is the revenue stream created by rental income. So long as the amount collected in rents surpasses the amount paid for mortgages, taxes, insurance, maintenance, repairs, and property management services, you will reap a well-sown harvest of rental income each month. The other way you can profit is by increasing the value of a turnkey rental property and mining the equity that you build. You either can take low interest loans against the equity or sell a property outright if you have others that will continue producing a good stream of passive income.

For example, a three-year $10,000 loan with a Prosper Rating of AA would have an interest rate of 5.31% and a 2.41% origination fee for an annual percentage rate (APR) of 6.95% APR. You would receive $9,759 and make 36 scheduled monthly payments of $301.10. A five-year $10,000 loan with a Prosper Rating of A would have an interest rate of 8.39% and a 5.00% origination fee with a 10.59% APR.
became $1,000,000 during an 18 year period (about 3x better than Berkshire Hathaway). Five – ten shares, or more, invested in a ROTH Ira and held *consistently* come h..l or highwater, with dividends and splits reinvested, may provide you a very pleasant surprise in 20 years or so. Asset Managers often do better than the assets they manage. Eaton Vance (EV) and T. Rowe Price (TROW) also did exceedingly well over a 25 year period.
There are dozens of ways to generate passive income. However, the option you select has to do with two metrics: time and money. Either you have a lot of time or a lot of money. Most people usually don't have both. But, if you have a lot of money, generating passive income almost instantly is easy. You can buy up some real estate and begin enjoying rental income. Or, you can invest in a dividend fund or some other investment vehicle that will begin generating a steady income for you.
You are also free to choose a fund that is based on any index that you want. For example, there are index funds set up for just about every market sector there is — energy, precious metals, banking, emerging markets — you name it. All you have to do is decide that you want to participate, then contribute money and sit back and relax. Your stock portfolio will then be on automatic pilot. 

With $200,000 a year in passive income, I would have enough income to provide for a family of up to four in San Francisco, given we bought a modest home in 2014. Now that we have a son, I'm happy to say that $200,000 indeed does seem like enough, especially if we can win the public-school lottery to avoid paying $20,000 to $50,000 a year in private-school tuition.

If you need cash flow, and the dividend doesn’t meet your needs, sell a little appreciated stock. (or keep a CD ladder rolling and leave your stock alone). At the risk of repeating myself, whether you take cash out of your portfolio in the form of “rent”, dividend, interest, cap gain, laddered CD…., etc. The arithmetic doesn’t change. You are still taking cash out of your portfolio. I’m just pointing out that we shouldn’t let the tail wag the dog. IOW, the primary goal is to grow the long term value of your portfolio, after tax. Period. All other goals are secondary.
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”.
In which socio-economic neighborhoods do you want to buy? I know real estate investors that have done very well buying and renting in lower-income neighborhoods. For me, it was a huge mistake. I fell into the trap of thinking, “I can buy a house for about half the cost as what I would pay in a better neighborhood.Even if I get slightly lower rent, say 70% as much, I’m still making a higher return.”Wrong!The money you lose on tenant turnover, unpaid rent and repairs far outweighs any benefit to buying property at a discount. Now, I always recommend to investors to never buy a house somewhere they wouldn’t want to live. If the business does poorly, you may end up living in one of your homes.
Let’s continue the vintage BMW idea. Old cars obviously require quite a lot of maintenance. Many people will buy a “fixer upper” with the intention of spending their spare time repairing and restoring it. There’s a very obvious market here: a guide to restoring different BMW models. Depending on your knowledge, you could produce detailed guides for the three or four most popular models and sell them. Not everyone restoring a car will buy them, but some probably will.
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