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.
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”.
When I sold my company, the buyers were both thrilled and surprised that I was willing to accept such a large portion of the proceeds as structure payments. For 5 years, I received a monthly check, including interest, for the sale of that company. I created the value a long time ago, added a little more value by allowing payment over time, and thereafter that value was paid on a schedule.
Stocks, bonds, 401(k)s, annuities, etc. are great ways to earn passive income. If you're not financially savvy, you'll want to hire a financial advisor who'll help you choose the right investments for you. You may want to take a couple of finance classes to understand what your advisor is speaking about when he/she recommends an investment strategy. Done right, investments can pay off for years.
Michael Ellsberg is the author of The Education of Millionaires: It’s Not What You Think, and It’s Not Too Late, which is launching from Penguin/Portfolio in September. It’s a bootstrapper’s guide to investing in your own human capital at any age. Michael sends manifestos, recommendations, tips, and other exclusive content to his private email list, which you can join at www.ellsberg.com. Connect with him on Twitter @MichaelEllsberg and on Facebook.
What's crazy is that my book income is more than my SF condo-rental income. Yet I didn't have to come up with $1.2 million of capital (the minimum cost to buy my condo today) to create my book. All I needed to create my book was energy, effort, and creativity. I truly believe that developing your own online product is one of the best ways to make money.
Thanks for writing this Mr. Samurai. I just got over the student loan hump but I feel pretty good about it at 27 having a graduate degree and being 100% debt free. Now that I’m on the other side it is good for my brain to absorb some of your knowledge regarding passive income investments. I love gleaning wisdom from older folks who have been there and done that. Mentors rock!
CD Interest Income: I only have one CD account left in the amount of $185,000 paying 3%. It expires at the end of 2018 and I’ll have to figure out what to do with it. After selling my SF rental house in mid-2017 for 30X annual rent, I’m left with about $500,000 in cash after investing ~$2,200,000. The best CD today is the CIT Bank 12-month CD at 2.5%. That’s pretty darn good because just a couple years ago, such a CD was less than 0.5%. The yield curve is flattening, meaning folks should take advantage of shorter duration CDs.
Freelancing is on the verge of going mainstream. Thirty-six percent of the international workforce now freelances, at least part-time. There are also 40.9 million adults in America who are self-employed. Clearly, freelancing is catching on. But with rapid growth come certain challenges, one being an increased competition for well-paying job and price reduction by those who think they can afford low-bidding at least for now. https://www.listenmoneymatters.com/wp-content/uploads/2017/08/LMM-Cover-Images-1.jpg
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A quick look on Pinterest and you’ll see no shortage of awesome solopreneurs sharing amazing income reports. And many of these #girlbosses are all online courses creators! While these women (and men) are pros now, they weren’t always. Everybody starts at the beginning, so don’t feel like you need to be a well-seasoned pro to earn passive income as a course creator.
The term “selling” probably doesn’t need much explanation, but it’s where value is transfered one time in exchange for money. Heart surgery, baguettes, and designer jeans are all ways to sell value. This one would probably the least optimal of all, at least for passive income, if it weren’t for an exception. This is because once you sell a normal commodity or service, you can’t re-sell it. Here’s the exception to this: software or digital goods can be duplicated with a very low marginal cost(now that we don’t use CDs, you can duplicate it with a cost of $0.00), and therefore, technically can be “sold” advantageously over and over and over again. This is why Microsoft grew to such a profitable company, and why I love selling digital goods.

Almost all of these ideas require starting a personal blog or website. But the great thing about that is that it's incredibly cheap to do. We recommend using Bluehost to get started. You get a free domain name and hosting starts at just $2.95 per month - a deal that you won't find many other places online! You can afford that to start building a passive income stream.


I personally haven’t tried any of the below methods so I can't speak from experience to how they work. In my mind, the most lucrative way is through building a REAL business online and providing your visitors with great value. However, after some thought, I decided to include these here because, quite often, the biggest roadblock for many is a mental one: believing that making money online is possible. From my experience, once you have made your first dollar, or even your first cent online, the world is suddenly a different color.
When I sold my company, the buyers were both thrilled and surprised that I was willing to accept such a large portion of the proceeds as structure payments. For 5 years, I received a monthly check, including interest, for the sale of that company. I created the value a long time ago, added a little more value by allowing payment over time, and thereafter that value was paid on a schedule.
Active income, on the other hand, involves earning money in exchange for a service. It could be a salary, an hourly wage, commissions, or tips. It’s essentially a trade of your time for a fixed dollar amount. Most people choose to live this way, and there’s nothing inherently wrong with that, as long as you understand that there will be a limit to how much money you can realistically earn.
The most liquid of the private investments are investing in equity or credit hedge funds, real estate funds, and private company funds. There will usually be 6 month – 3 year lockup periods. The least liquid of the private investments are when you invest directly into private companies yourself. You might not be able to get your money out for 5-10 years, depending on the success of the company and upcoming liquidity events.
While all the ideas in this article can and do work, you can’t go in half cocked. Just putting up a niche website and expecting people to magically come and click on your ads won’t get you very far. Instead, you’ll need to put work into building an audience. You can put a course up on Udemy in a few hours, or a theme on ThemeForest, but unless you market it, you won’t sell very many copies. 

“There is no such thing as 100% passive income,” says Flynn. “Even with real estate you still have to manage your properties, or even with the stock market, which is potentially passive income, you still have to manage your portfolio. With online business, there is no such thing as 100% passive income — and this is coming from a guy with a blog called SmartPassiveIncome.com. The definition of passive income is ‘building these businesses of automation,’ but in order to keep them automated and keep that trust going with your audience on top of that, you do have to keep it up every once in a while — so a lot of time upfront and a little time after. But there is alway time involved.”
4) Treat Passive Income Like A Game. The only real way to begin your multiple passive income journey is when you are making active income. The initial funding has to come from somewhere. Hence, treat passive income as a game that has various levels. If you fail to achieve one level, it’s not the end of the world since you still have active income and can restart. Furthermore, a game is meant to be played with integrity. Using shortcuts (non passive income streams), someone else’s income as a supplement (spouse), or one-offs (capital gains) does not count. The primary purpose of any game is to bring enjoyment to the player and beat the boss.
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