Do you watch real estate reality shows? Have you dreamed of fixing and flipping houses? What about being a landlord? Believe it or not, real estate is a good way to earn extra income. Real estate investing includes fixing and flipping houses. This requires capital in the form of cash and/or credit. If you can partner with someone, do it. You'll attend housing auctions and bid on houses; you can get them for a good price. Hire a contractor to fix up the inside and outside (could cost anywhere from $10,000 and up), have the house appraised, sell it, make a profit and split the profits between you and your partner(s). Of course, you could buy properties (e.g., houses and apartment buildings), and become a landlord. Another alternative is to become a real estate agent. Speak with seasoned investors and realtors to find out if this passive income strategy is right for you.
One of the most appealing options, particularly for millennials, would be #12 on your list (create a Blog/Youtube channel). The videos can be about anything that interests you, from your daily makeup routine (with affiliate links to the products you use), recipes (what you eat each day) or as you mention, instructional videos (again with affiliate links to the products you use). Once you gain a large following and viewership, you can earn via Adsense on YouTube.
I’m looking at accepting a professor job. It’ll be more than a 50% pay cut. But I’ll have the same life you describe – endless summers and an entire month every winter to ski. I’m thinking in the end, eventually, I might even end up wealthier in more ways than one. Happy people tend to be the most successful. I have no desire to diversify. Dividend stocks allude me. CDs seem like a good choice for older people, but I have time on my hands and real estate knowledge, so I’m sticking with what I know, despite the fact that most people will tell me it is foolish and I should diversify.
Be aware that before your passive income stream can start making money, you have to spend many hours creating it, including building the website itself. You must also monitor your sales to see if you must make changes, take steps to ensure that your website appears near the top of the results page of search engines, and periodically add new content to keep visitors coming back.
2. This article isn’t intended to be about making $50k per year from $0 to start with. This is intended to show different ways that it’s possible to generate $50k in passive income. As for your rental property comment, check out RealtyShares or other similar companies. You can be a rental property owner without having to run the business. You can be a limited partner and just invest in real estate, and leave the actual work to the general partner. Basically, there are options to make $50k without working, but like the first paragraph says – front load your life!
While building apps for Apple (or Android) mobile devices can be a lucrative way to generate passive income online, it's not as easy as many people make it seem. Beside the fact that it’s hard to get your app noticed among the millions being released every year, most people expect apps to be either free or very inexpensive. In fact, a recent study found that only 11% of apps are paid for. The number of paid apps will only decline over time as more players join the market. The key, like many of the business model mentioned here, is to be strategic and creative from the very start. There are a few ways to monetize your app and keep it free for users. Examples include advertising, premium services, and sponsors.
You are valuable. Your time, your work, knowledge, experience, and output are all valuable. In fact, your employer (or your customers, if you’re an entrepreneur), probably pay a lot of money to rent these things from you. The problem is, whether you’re a doctor, a lawyer, an artist, an engineer, or even a baker, the value you create is consumed once — then it’s gone. You can only sell a loaf of bread once. You can only sell each open heart surgery to one client. The value trades hands, and now it belongs to the customer — you get paid once. 

I enjoy how you lay out real numbers. A lot of people wouldn’t do that. While you admit that you are somewhat conservative, I think the $1M in CD’s is just too conservative. Assuming you don’t need the cash flow now (which you say you just save anyways) then all that could be invested for potentially higher returns. For example, what if you bought San Francisco real estate along the way instead of CD’s. Or, an SP500 Index fund. I bet your average return would have been higher than 3.75%. Sure you could lose it, but the point is if you don’t need the cash flow now, you should try to increase that nut as high as possible until the day you actually need it. Your nut could be $5M right now if you had invested in asset classes other than CD’s for the last 14 years. Don’t get me wrong, you have done far better than me, but I guess I would take a little more risk if you don’t rely on that cash flow.
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!)
Question: You mention receiving $200k of passive income a year, but your chart shows half of that coming from real estate holdings, and reading between the lines it appears that you hold mortgages against those holdings. Then you conclude that $200k/yr of passive income should be enough to live comfortably anywhere in the world. So are you subtracting your real estate expenses (taxes, insurance, mortgage payments, maintenance, remote property management company fees, etc.) when you report your passive income from those properties? Really I think it’s the net (after taxes and everything) that tells us what is left over to “spend” on living, right? When I set up my spreadsheet to retire early at age 47, I calculated the after-tax income I would need to live. Then I compared that to my income streams (estimating tax on the taxable income streams) to measure the surplus/shortfall. Also some good advice from GoCurryCracker: If you can minimize your taxes so you’re in the 15% tax bracket, you can possibly receive tax-free long term capital gains. I agree with your philosophy that time is more important than money as we age. I am not sure I agree with a philosophy that is fixated on needing such a large income, and would rather minimize taxes if it’s all the same on the happiness meter. Furthermore, having 20 plus income sources in the name of diversification adds stress and requires more management (TIME!). I think this is fine for those of us while young, as we have the energy to work hard. But as time becomes more important, the extra headache of managing, planning, and buying/selling our assets becomes a resented hindrance on par with the resentment we felt when working for an employer and fighting traffic each day to go to a job we hated. Every thing we own in actuality owns us, by virtue of its demands on our time and affections, and that includes investments. It also includes our home, and is a good reason for downsizing. As long as we have food on our table, a roof over our heads, and clothes on our bodies, what more do we need? I think we need to consider freeing ourselves from the weight of the chains of managing too many ventures. Personally, I plan on investing in no more than 5 simultaneous ventures ever, with the exception of some IRAs that I just plan to let sit for the next 20 years (and therefore no thought or anxiety required).

Even if you don’t have the skills right now, it’s possible to develop them. Envato Tuts+ has a load of great courses that teach you how to make WordPress themes, Photoshop actions and so on. If you invest a few months into learning the necessary skills, you might well be able to carve out a spot for yourself in the Envato Market or in our new curated website Envato Elements. 
I wish I had more time to put into real estate. Given the run up since 2012, I may even be interested in selling my condo that I currently rent out. I need to get it appraised to really see what it’s worth, but I think conservatively it’s gone up ~50%, although rent is probably only up ~10% or so. I am bullish on rents going up in the future… mostly in line with inflation, or perhaps even slightly faster due to constricted credit and personal income growth which should provide a solid supply of renters. At this point, I just don’t want to manage the property. I’ll probably look into a property manager as my time is likely worth turning it into a nearly passive investment.
You are valuable. Your time, your work, knowledge, experience, and output are all valuable. In fact, your employer (or your customers, if you’re an entrepreneur), probably pay a lot of money to rent these things from you. The problem is, whether you’re a doctor, a lawyer, an artist, an engineer, or even a baker, the value you create is consumed once — then it’s gone. You can only sell a loaf of bread once. You can only sell each open heart surgery to one client. The value trades hands, and now it belongs to the customer — you get paid once.
However, when you lack the money, you need time. You'll need to invest the upfront time now in order to reap the benefits of automatic income later. It just doesn't happen overnight. So don't expect it to. However, you can do this without quitting your day job. All it takes is some sincere effort over a consistent period, and voila! But, to get there, you'll need to consistently burn the midnight oil or get up at the crack of dawn. Your choice.
As a private lender, you can lend to anyone in your social circle. For example, many home rehabbers need access to a source of capital they can tap into very quickly in order to fund the initial purchase of their properties. You can partner with a rehabber who uses your capital for a short-term in exchange for an interest rate that is mutually agreed upon.
When withdrawing money to live on, I don’t care how many stock shares I own or what the dividends are – I care about how much MONEY I’m able to safely withdraw from my total portfolio without running out before I die. A lot of academics have analyzed total market returns based on indices and done Monte Carlo simulations of portfolios with various asset allocations, and have come up with percentages that you can have reasonable statistical confidence of being safe.
Again, no leader worth her salt will be attracted to such an opportunity. And anyone you do hire to lead the value creation, if they have two brain cells, will see that she's the one adding all the value. Sooner or later she will simply find a way to cut you out of the value chain, either by requiring more and more compensation, or by going off and competing against you (and actively at that.) Why does she need you? You're not adding any value anyway!

I've got a $185,000 CD generating 3% interest coming due. Although the return is low, it's guaranteed. The CD gave me the confidence to invest more aggressively in risk over the years. My online interest income has come down since I aggressively deployed some capital at the beginning of the year and again during the February market correction. You'll see these figures in my quarterly investment-income update.
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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