Anthony, nice setup! To your question about the rental mortgages, you haven’t said what interest rate you are paying. As a start, if you are paying more than the risk free rate (Treasury bills) which you probably are, then a true apples to apples comparison would be yes, pay off the mortgage. But, if you are comfortable taking more risk, you have other options to invest in which you *hope* will yield you more over the coming years. You also didn’t say whether the rentals generate net income and if so, how much? What is the implied rate of return on the equity you have invested in them? If you pay the mortgages off, you’ll have even more equity tied up, will the extra net income make that worthwhile? Maybe you should use the money to buy more rentals instead, if purchase opportunities still exist in your town. … this is less of an answer than a framework to analyze the decision, hope it is helpful.
Instead of working in the service framework, passive income necessitates that we build (or otherwise acquire) something that inherently contains value, which can then be easily and repeatedly transferred to others with little or no work. Plain and simple, we have to create or buy valuable assets, preferably ones that deliver their value automatically. There are a lot of ways to do this, but they all fall into the 3 categories above, and realistically, a lot of them look like different flavors of the same thing.

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.
"What makes business work is creating value. If you're going into the business with the intention of not creating value, but of having it magically provide money for you, then you often make really bad choices. The business that you're investing in or creating doesn't tend to be creating value for its customers or for anyone. So it doesn't tend to spit off the cash you're hoping it will. So many times I've seen people pursue passive income, and end up having active losses instead. They just spend a lot of time and money trying to push responsibilities off on other people and having it not work."
Immediately after I graduated from business school, a lot of people began asking me what I would do, or if I’d found a job. The answer was almost always “working a few hours a week on some side projects until re-launching my startup.” Whereas this may sound like an unfortunate or undesirable outcome, really was not so bad… My gross income then — without really “working” on anything — was higher than it was when I was working 80 hour weeks running a $3M/year eCommerce company. Sure, it wasn’t glamorous, but it was all part of a strategy that would eventually lead me towards “accidentally” building a 7-figure media business that runs whether or not I show up to work this month. Let me explain…
There are hundreds, if not thousands, of websites offering users the ability to get paid for taking surveys online. Same as with Cashback sites, if you encounter a survey site where sign up if not free, simply avoid it. I have not checked it myself, but a few online entrepreneurs suggest trying toluna.com. Also, you might want to try Cash Crate - In addition to getting paid for taking surveys, they offer cachbacks and other quick online income perks.
Well, my first book project didn’t generate the interest I would have liked to, but another set of products suredid. In 2013, I launched a course on Udemy, which grew so fast, it became my biggest income earner of all time. That course resulted in a series of books (audio, digital, and print), a not-so-passive podcast, and even lead to my now full-time gig: SuperLearner Academy. Though I run the company full time, it is, for all intents and purposes, an automated business.
Have you always wanted to own your own business? You could start a side business while you work a full-time or part-time job. For example, if you're a graphic or web designer, you could start your own graphic or web design business on the side. If you like to make jewelry, you could sell at craft fairs and online. Starting a business may be daunting, but if you believe in you and your work, you could earn a decent living, maybe even quit your day job. Search out those who are doing what you want to do and interview them. Find out the mistakes they made and ask for guidance.
It was at that moment that I realized that I am not in control of my career or my financial well-being. In our group, shifts and hours equated directly to money. I was a highly-paid hourly worker, but the job was only as good as the hours I was given. To acquire additional hours, I would have to scramble, hustle, and pick up extra hours when other people were willing to give them up.
Inspired by you, I started a tax/personal finance a month ago. I figured if it works out, it will create a good side income for me. If not, at least I can use the blog to build my brand as a tax lawyer. Other than that, my current investment portfolio is heavily focused on index funds because of its historical performance and tax & cost efficiency. Right now my dividends income every year is about $14,000. I also have a good amount of unrealized capital gains every year from my investment, though I don’t count the capital gains as my passive income as they are paper gains, at least for now.
You won’t see the principal payment deducted on most cash flow calculations. I like to remove it to find the actual cash flow of the property and it’s important since we’re talking about passive income strategies. Your cash flow may be low or even negative on the property but it might still be a good investment if you are earning a good return through an increase in equity.
Most people who set up passive income don’t do it so they can lay on a beach all day, or even so they can spend their time learning a third or fourth language (ok, maybe I’m doing that), or living on private islands. No, the point of passive income is to liberate your time for more fruitful endeavors — whatever those may be. If you have the ambition and gall to get out of the “9 to 5 game” and set up passive income, chances are you won’t be happy with sitting on your butt or traveling year round. You’ll want to do something with meaning and purpose.
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.
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.
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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