My favorite type of semi-passive income was rental property because it was a tangible asset that provided reliable income. As I grew older, my interest in rental property waned because I no longer had the patience and time to deal with maintenance issues and tenants. Online real estate became more attractive, along with tax-free municipal-bond income once rates started to rise.
It’s not just the little guys like me who are being squeezed by the constant updates. Even YouTube’s top creators have expressed frustration with changes to the YouTube monetization platform. It’s constantly changing and evolving, so you must be willing to adapt. Plus, it helps having a blog so you’re not relying on a single platform or your income.
I have had a LC account for almost 2 years. Invested 5k. A lot of very small loans. Unfortunately I had to invest though Folio FN. The fees reduce your return. Now, they are not even allowing that. My interest and return of principal are not being reinvested. I talked with LC and they are working on it for my state. Even if I can obtain access to the prime portfolio, I would only place 10 percent of my cash here and would reinvest for at least 3 years. I am still concerned about what would happen when a recession hits.
In real estate, your passive opportunities are in private lending and rental properties. Private lending commonly involves lending funds to a real estate investor or business in exchange for a set return and length of time. (Full disclosure: I am co-partner of a turnkey investment company.) Turnkey rental properties allow the investor to be as hands-off as they like. This means a turnkey company purchases, rehabs, tenants and manages the property. To truly make this a passive investment, turnkey companies do all the work for you.
Lending Club went public in 2014 and is now worth about $1.7B. They advertise P2P lending returns of over 7% for well-diversified portfolios of over 100 notes. I’ve personally been able to achieve a 7.4% annual return over the past two years in a completely passive way by investing in A and AA notes. Others have achieved a 10% annual return through relatively minimum effort.
Now, if you choose to deliver part or all of your course in video format, you can use professional video hosting sites like Wistia or Vimeo. Beside giving you the option of removing the hosting company’s logo, these services also provide analytics which can show you how effective your video is at holding your audience’s attention. Alternatively, you can use litmos, a learning management system that enables you to create an online course with your own branding, domain name, and landing page. There is no percentage cut taken from your revenue like Udemy. Instead there is a monthly fee for their service.
Being able to generate passive income largely depends on your audience, and if they detect that you care more about making money than serving them, you won’t succeed. “Whenever I’ve seen people do something just for the money, they’ve failed because their intentions aren’t driving them in the right direction. It should always be about helping people and about the passion of making others feel better. The byproduct of doing that is generating money,” says Flynn.

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 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.
Of course, there’s nothing to say you can’t do both. You can manage your own commercial real estate rentals and flip houses while you have someone else help manage residential rentals. You can invest in REITs and real estate crowdfunding. You’ll get the higher returns of active management while benefiting from the diversification and ease of passive income through other sources.
1) Save Like Nobody Owes You Anything. Passive income starts with savings. Without a healthy amount of savings, nothing works. Your overall “Money Strength” will be an F- if you do not build a financial nut. In our current low interest rate environment, you must save even more than before. It’s important to also realize that the savings I am referring to is AFTER-tax savings. You need to save money after contributing to your 401k and IRAs since you can’t touch pre-tax retirement accounts without a penalty until 59.5. Ideally everyone should max out their pre-tax retirement funds first, but if you don’t have enough funds and want to retire earlier then a decision to have more accessible post tax money will still work.
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.
There is a big misconception about rentals & people thinking that it’s passive.. rental income is far from passive. Many people flock to buy rentals as a way to “retire rich” but realize shortly thereafter that it really isn’t that easy or true.. Ask me how i know. I have bought a lot of houses from tired and burnout landlords. Luckily, there are better options out there.
Remember, the skills you have are an asset, they are your “unfair advantage.” They are essential to your unique personal brand, and you can start making money online using those skills if you have the right strategy, tactics, and mindset in place. Another way to describe this is your “unfair advantage,” a term I was first introduced to by Lain Ehmann in SPI Podcast Session #37.
Dividend stocks tend to be more mature companies that are past their high growth stage. Utilities, telecoms, and financial sectors tend to make up the majority of dividend paying companies. Tech, Internet, and biotech, on the other hand, tend not to pay any dividends because they are reinvesting most of their retained earnings back into their company for growth.

I don’t really know much about those…I should take a look from a diversification standpoint. If you don’t mind me asking, what do you target for your net effective tax rate on your passive income? Also, I’m sure you’ve probably covered this somewhere, but how do you deal with healthcare? One more dumb question…have you found that you spend more or less money than you anticipated once you retired?

That strategy seems waaaayyyy less risky than actively picking stocks of supposedly “reliable” stocks that issue dividends, which could be cut at any time due to shifting industry trends and company performance. Dividend investing feels like an overly complex old-school way of investing that doesn’t have a very strong intellectual basis compared to index investing.


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Passive income is defined as income-generating activity that is independent or loosely dependent on time commitment. Just so we’re on the same page, here, there’s no such thing as making money without creating value (I wish), and creating value takes time and effort. So, you are technically transacting time for money, in a way. But passive income is where we separate or at least alienate the proportional relationship between time spent and money made. It’s where there is no longer a fixed ratio, and if there is, it’s not a 1:1 ratio, but more like a 10 or 20:1 ratio of man-hours-worth-of-time to actual time. As another side note, knowing how much your time is worth both to you and on the open market is a valuable piece of information for guaging how effective your passive income activities need to be.
Real Estate Crowdsourcing – After selling my SF rental house in mid-2017 for 30X annual gross rent, I  reinvested $550,000 of the proceeds ($810,000 total) in real estate crowdfunding, based in San Francisco. My goal is to take advantage of cheaper heartland real estate with much higher net rental yields (8% – 12% vs. 2% – 3.5% in SF) and diversify away from expensive coastal city real estate which is now under pressure due to new tax policy which limits SALT deduction to $10,000 and new mortgage interest deduction on mortgages of $750,000 from $1,000,000 for 2018 and beyond.

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.
Whether you choose to invest in just one of these modern REITs or both, keep in mind that since they’re private funds and not stocks, you won’t be able to easily liquidate your investment and access your cash right away. Depending on your investment, plan to see your money tied up for anywhere from six months to five years. However, you’ll most likely still receive monthly or quarterly payments, depending on which investment opportunity you select.
So, I sat down, wrote a few posts, and posted them on a simple website under the name Passive Income MD. I honestly didn’t expect anyone to read it. Well, that was two years ago and so much has happened since. Most notably, I’m now in a position where I am financially independent from medicine. In fact, I’ve started to cut back at work in order to find that happy work-family life balance. I don’t have any desire to quit medicine completely, but I do intend to retire gradually.
Though it can take a while to build up enough cash to put a 20% down payment on an investment property (the typical lender minimum), they can snowball fairly quickly. The key here is to correctly project income and expenses in order to calculate cash flow (the free cash you can put in your pocket after all associated property expenses have been paid). However you have to be sure to include the cost of a property manager in your calculations unless you want to manage the property yourself. Even with a property manager, you may be required to make large repair decisions every now and then – so while this is not a 100% passive activity, you are not directly trading your time for money like traditional employment.
stREITwise offers a hybrid investment between traditional REIT fund investing and the new crowdfunding. The fund is like a real estate investment trust in that it holds a collection of properties but more like crowdfunding in its management. The fund has paid a 10% annualized return since inception and is a great way to diversify your real estate exposure.
What is refer-a-friend? Essentially, you make money for using a service and telling others how great it is. Most of the times, you’ll get a unique link that you can share with friends directly or throughout social media. Whenever anybody clicks your link and signs up and/or makes a purchase, you’ll get a bonus. The bonus can be in the form of cold hard cash or an account credit.
They also launched an incredible Retirement Planning Calculator that pulls in real data from your linked accounts to run a Monte Carlo simulation model to output the most likely results of your financial future. I strongly suggest you run your own numbers, play around with the income and expense variables, and see how you stack up. It’s all free and easy to use.
Reinvest your passive income. Once you've started earning a good amount of passive income, you can reinvest that income to earn ever more. This income will then produce further income that you can also reinvest. This cycle produces ever-increasing income streams without any direct cost to you. For example, you could reinvest revenue from website advertising into more advertising that brings readers to your site. This increase in traffic would then further increase your ad revenue.[12]

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.
Case Schiller only tracks price appreciation of RE. RE as rental investment vehicle is measured primarily on rental yield or cap rate or some other measure. Price appreciation in that scenario is only a secondary means of growth, and arguably should be ignored as a predictor of returns when deciding on whether or not to invest in rentals. More important key performance indicators for rentals are net operating income and cash ROI. Appreciation, if it occurs, is a bonus.
Ever find yourself humming a tune, or laying down tracks for yourself or friends? Your next catchy phrase might fetch you a solid passive income stream. On sites like ProductionTrax and Audio Network, musicians can license their compositions for background music in apps, commercials, and websites to earn more money. Read more about this strategy at The Guardian.
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.
Starting a blog is one of the most popular side hustles to earn online income. This is because whether you have 10 people or 10 million reading your content, the amount of your effort to write an article is the same. Websites have low start-up costs and you can literally buy your domain, launch your site and have a few pages created in less than an hour. You won’t start making money right away, but you will be building towards that first $1 of income.
I read about early withdrawal penalties on IRAs/401Ks very often. Almost always with a statement of “locked up” or “can’t touch” until 59.5. I’m sure you and well informed readers as well know about SEPPs in regard to IRAs/401Ks. For those that don’t SEPPs aren’t perfect but they are a way to tap retirement funds penalty free and I will be using in the future as I have over half of my equity investments within retirement accounts. South of a mil, North of a half. Let me add that I think your blog is outstanding. 

* I use Personal Capital to track all my finances in one place. It’s much easier to use their free software to follow 28 accounts on one platform than to log into various accounts to check my balances. They’ve also got great tools for x-raying your portfolio for excessive fees, recommending a more optimized asset allocation, and planning for retirement with their Retirement Planner.
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