I will share what we did, because it’s an incredible success story. We used an existing tax loophole where if you sell your primary residence (after having lived there at least two years) you get to keep your profit tax-free. So, we stair-stepped. We bought house after house, at least two years apart, used the profit money to pay down on the next house (so on and so forth, yadda yadda) building up equity as we went along… and now, we own a $600,000 house debt-free. And now we are using our paid-off home as leverage to borrow money to buy commercial buildings to rent out. I like commercial because it’s a BUSINESS transaction… kids, pets, other wear and tear that you see with residential rentals is nonexistent. People take care of their business space much better than residential. You have to be in a good area for renting out commercial – a thriving business community – to make this work. But that’s how we “made it”, and though it took 15 years, we will have residual income to take care of us when we’re old enough to retire. People made fun of us for moving so much, but who’s laughing now? 😉 Oh, and our child only had to change schools once (and we wanted to anyway) because we stayed in the same general area as we moved around. We were careful not to disrupt his life too much.
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.
If someone stole my hard work and passed it off as their own, I’d be livid and would pursue them to the ends of the Earth for full restitution. A man I hired to work with me registered my preferred domain name of my business and has re-registered it in subsequent years. That’s bad enough; I’m mad as hell. The worst aspect of his behaviour is that I don’t know WHY he has done that; I paid him the fee we had agreed on and thanked him for his input. We also got along perfectly well during the project so far as I know, so I don’t see what his problem is.
Although it is passive income, I love helping people and find that I actually put in quite a few hours per day creating new products, talking to customers, or getting my name out there. I think you have to have this passion, and you need to keep working for your own sanity, plus to keep you ahead of the competition. Even though it is called passive income, if you lie still for too long, you could start to see your business declining.

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. 

Dividend Income: Dividend income is wonderful because it is completely passive and is taxed at only 15% if you are in the 25%, 28%, 33%, and 35% income tax bracket. If you are in the 39.6% income tax bracket you will pay a 20% tax on your dividends. My dividend income portfolio mainly consist of dividend equity and bond ETFs such as DVY, VYM, MUB, TLT, and IEF. Total stock and bond income is a little over $100,000 a year due to a heavy accumulation of stocks and municipal bonds after selling my house.
Amazing that you saved between 50% to 75% living in NYC…I think that is one thing holding me back…the cost of living here. I’d like to invest in real estate, but I can barely afford to buy a place to live. I don’t need a large income to be happy, but I probably do need an income to support living in NYC as we don’t plan on leaving. The only thing I’m doing at the moment is saving in my 401K, IRA and a I dabble in stocks and P2P lending.
Most credit card companies offer sign-up bonuses to entice you to open a credit account with them. As long as you don’t spend money just to hit the minimum balance and always pay your balance on time, this can have a minimal impact on your credit score while earning you hundreds – or even thousands – of dollars a year. Some of the best travel credit cards offer 100,000 points to new accounts when you meet reasonable spending requirements.
We are going to start with 1.5 years of all spending needs in cash. We will draw 1800 to 1900 per month. We will add to this from the index funds by taking a portion of the gains in good years to supplement. This is the total return portion of the equation. Obviously, if stocks decrease drastically over a 5 year period, then I would have to reload by selling some of the ETF holdings.
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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.
Obviously, you want the best tenants you can find. If you’ve chosen a property in a more affluent and stable neighborhood, your tenants are more likely to be responsible with your property and reliable about paying the rent. Properties in lower income areas are more likely to attract tenants that become delinquent in paying the rent, move out without notifying you, and damage your property. This is part of the higher risk of this type of investment property. You’ll end up with the expense of repairs and less income to spend on those expenses.
The second category of passive income is drawing on sources that do not require capital to start, maintain, and grow. These are far better choices for those who want to start out on their own and build a fortune from nothing. They include assets you can create, such as a book, song, patent, trademark, Internet site, recurring commissions, or businesses that earn nearly infinite returns on equity such as a drop-ship e-commerce retailer that has little or no money tied up in operations but still turns a profit.
If you know anything well, a place, how to fix something, how to make something, how to do something, you can write a guide for it. You can sell your guide as an e-book, offer it as a download for a fee on your site or reach out to bloggers with similar content and ask if they will offer it as a paid download on their website (for a price of course).
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.
John has a daily (yes, daily) podcast where he features an interview with a successful entrepreneur. Now, John enjoys many hundreds of thousands of downloads per month, he’s written a book, has products and has opened up a ton of opportunities for sponsorships and partnerships that wouldn’t have come otherwise. He’s not the first person to have a show dedicated to interviewing rock star entrepreneurs—not even close—but he’s definitely the fastest to see these kinds of results.
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