The PPACA Medicare tax is a dangerous tax IMHO. It is an entirely new kind of tax. It is small and in jeopardy of going away but I predict it won’t. If it goes away it won’t be for long and it will grow over time – like most taxes. 3.8% is a starting point. This one has the added political appeal of “taxing the rich” and “unearned income” that makes it more palatable to the electorate.

Nobody gets early FI investing in bonds, CD’s, or even stocks unless they make a huge income or are extremely frugal or a combination of both. Paper assets just don’t provide enough returns. Business income can be great but it is typically not as semi-passive as I would like and there is a relatively high failure rate. That is if you can monetize an ideal to begin with. RE investing needs to be higher ranked IMO as a way that the “average guy” can become FI.
I also disagree that every person will crave more and have to go for more. That may be a true statement for a lot, but it doesn’t have to be true and it isn’t for everyone. The other perspective of that is that most likely the people who get themselves to financially freedom, because it is no small feat, are the type of people who are extremely driven and motivated to further challenge themselves, so it’s doubtfully in their nature to stop once they actually can.
Depending on the level of AAII otherwise earned in a particular year, you may wish to consider investments that lean towards growth rather than annual interest or dividend income, as you may better be able to time the recognition of a capital gain. In addition, since capital gains are only 50 per cent taxable, it would take $100,000 of realized capital gains to generate $50,000 of passive income that is counted towards the AAII test.

This shouldn’t be a surprise. I mean, when I speak to groups and ask how many docs in the room would cut their hours/shifts/call etc if their finances allow it and they all raise their hand. So taking a group of docs who not only have their financial ducks in a row, but also have a side income and pursuit already, why would they be working full-time?
Are you doing it just for the money?  It has been my experience, and that of many others, if your reasons for, well, doing almost anything, are genuine, that it will be evident in all that you do.  If you are looking to generate passive income, then do so from a place of wanting to help people.  To improve people’s lives.  If you have a passion and desire to help people realize their hopes, dreams and goals, you almost certainly will make money doing it.
One of the easiest ways to get exposure to dividend stocks is to buy ETFs like DVY, VYM, and NOBL or index funds. You can also pay an algorithmic advisor like Wealthfront to automatically invest your money for you at a low fee. In the long run, it is very hard to outperform any index, therefore, the key is to pay the lowest fees possible while being invested in the market. Wealthfront charges $0 in fees for the first $15,000 and only 0.25% for any money over $10,000. Invest your idle money cheaply, instead of letting it lose purchasing power due to inflation. The key is to invest regularly.
You could also make some passive income with medium involvement by investing in dividend stocks. This means you buy stocks that pay out dividends. You’ll have to do your research to find the best dividend stocks. That way, you can ensure that your dividend payouts will last for a while. Similarly, you could simply open a high yield savings account or build a CD ladder. Again, you’ll have to do your research to find the right ones and keep an eye on the accounts to make it a successful source of income.
Another form of passive income can come from investing in private equity opportunities in businesses that are growing.  There are certain limitations on who can invest, but can be a great way to generate passive income from profits in a business that you have very little if any active role in.  If you invest in and now own part of the business, and it is successful, you would then be entitled to regular profits from the business, and potentially even a great return on your original investment.  You can do this by either purchasing some of the business with your money, or lending your money at a certain interest rate to the business.
Investing in coins and collectibles: Buffalo nickels and Spiderman comic books are good examples of coins and collectibles that can rise in value, and thus offer opportunity for passive income investors. You'll need to get up to speed on the value of any coin or collectible under consideration, but once you do so, you're on the way to price appreciation on a commodity you'll be paying a lower price to buy, and will garner a higher price when you sell.
This one may seem simple, but that’s only because it is. If you were to move your savings from a traditional, brick-and-mortar bank with a low-interest rate and into a high-yield savings account online, over time you can make a surprising amount of extra cash. Online banks are FDIC-insured just like the traditional brick-and-mortar institutions, so your money is just as safe.
I truly believe generating $10,000 a year online can be done by anybody who is willing to dedicate at least two years to their online endeavors. Here is a snapshot of what a real blogger makes through his website and because of his website. Roughly $150,000 a year is semi-passive income followed by another $186,000 a year in active income found through his site. Check out my guide on how to start your own blog here.

Passive income, in a nutshell, is money that flows in on a regular basis without requiring a substantial amount of effort to create it. The idea is that you make an upfront investment time and/or money but once the ball is rolling, there's minimal maintenance required going forward. That being said, not all passive income opportunities are created equally. For investors, building a solid portfolio means knowing which passive investing strategies to pursue.
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.
Blogging is still going to take work starting out. That path to $5,000 a month didn’t happen overnight but just like real estate development, it build up an asset that now creates constant cash flow whether I work or not. I get over 30,000 visitors a month from Google search rankings, rankings that will continue to send traffic even if I take a little time off.
Portfolio income. This includes interest, dividends, annuities, and royalties not derived in the ordinary course of a trade or business. It includes gain or loss from the disposition of property that produces these types of income or that’s held for investment. The exclusion for portfolio income doesn’t apply to self-charged interest treated as passive activity income. For more information on self-charged interest, see Self-charged interest , earlier.
In order to generate $10,000 in Net Operating Profit After Tax (NOPAT) through a rental property, you must own a $50,000 property with an unheard of 20% net rental yield, a $100,000 property with a rare 10% net rental yield, or a more realistic $200,000 property with a 5% net rental yield. When I say net rental yield, I’m talking about rental income minus all expenses, including a mortgage, operating expenses, insurance, and property taxes.

I had to get out. I actually had this random Facebook ad come up in my news feed (go figure) and it eventually led me to a webinar that taught on how to start an email marketing business (which is, by the way, the most profitable form of affiliate marketing – or ANY marketing for that matter). I listened through the whole 2 hours, completely mesmerized. By the end of it, I knew what I was going to be focusing on to help my family out of the pit of debt we were in and into a world free of financial stress. I didn’t know if it would actually work, but eventually it lead to EXCESS income!
×