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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.
Then came a few recent emails from readers already on their first or second rental properties since I started the blog, thanking me for the encouragement to get going. Others had started their own blogs or started their own businesses. It was then that I realized my favorite part of this whole blogging journey has not been the financial gains (although you won’t hear me complain about it), it’s been the interactions with other physicians who are trying to achieve the same thing I am.
Who cares? I don’t care one bit about building a “successful company” with most of my passive projects. That’s for my active projects — and I’ve done that when I converted them into active projects. For passive income, I can build products and automated services that are useful enough that people want to buy and use them. My Magento modules and Udemy course had 5 star ratings despite being passive. I knew back then that I could probably sell 2x as many copies of each if I made it my full time job — but I chose note to. I realized that if I could have more fun, get more fulfillment, and make more money out of other passive activities, and that’s why I don’t care that my passive businesses are small and nichey. Again, though, converting one of them into an active business has made it much more successful — so I would just remind you that they aren’t mutually exclusive, and if anything, having a Passive Income side business or 2 let’s you try out a few different waters before you dive in to any one.
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.
If you need cash flow, and the dividend doesn’t meet your needs, sell a little appreciated stock. (or keep a CD ladder rolling and leave your stock alone). At the risk of repeating myself, whether you take cash out of your portfolio in the form of “rent”, dividend, interest, cap gain, laddered CD…., etc. The arithmetic doesn’t change. You are still taking cash out of your portfolio. I’m just pointing out that we shouldn’t let the tail wag the dog. IOW, the primary goal is to grow the long term value of your portfolio, after tax. Period. All other goals are secondary.

Amazon affiliate program is a great way to promote physical products through a reliable, trustworthy, and well-known online store. The fact that everyone knows Amazon is probably their biggest advantage. On the downside, commissions are fairly small - they start at 4% for most products and can go as high as 8% depending upon how many sales you make. However, when you send someone to Amazon, you earn a commission on whatever they buy within 24 hours of clicking your link, whether they end up buying the product you promoted or not. So, for example, if you promoted a book but the person you sent to Amazon ended up buying an expensive camera as well, you’ll get the commission for both the book and the camera. This can add up.
Everything passive first takes active energy. The time to put in the effort is when we are young and not ravaged by disease or burdened by family obligations. I remember being able to snowboard from 9am until 4pm every day for a year. Now, I’m lucky to last from 11am until 2pm without wanting to go to the hot tub and drink a bucket full of beer! If we can appreciate how lucky we are when we are young, we’ll be able to maximize our vitality and live financially freer when we are older.
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Amazon affiliate program is a great way to promote physical products through a reliable, trustworthy, and well-known online store. The fact that everyone knows Amazon is probably their biggest advantage. On the downside, commissions are fairly small - they start at 4% for most products and can go as high as 8% depending upon how many sales you make. However, when you send someone to Amazon, you earn a commission on whatever they buy within 24 hours of clicking your link, whether they end up buying the product you promoted or not. So, for example, if you promoted a book but the person you sent to Amazon ended up buying an expensive camera as well, you’ll get the commission for both the book and the camera. This can add up.
When I started building my architecture-related business in 2008, I made my first dollar through advertising. I’d spent a lot of time and money building the site and getting traffic. Then one day I threw an ad on the site one day, and I made $1.18. Sure, I could find that much under my couch cushions—but that’s not the point! The point is that I was able to build something online, put an ad up, and make money without having to do anything. I learned it was possible, and it motivated me to move forward.
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.
​Self Publishing is mainstream today. When you purchase an eBook off of Amazon there’s a pretty good chance you’re buying a self-published book. Self-publishing is also ridiculously easy. I tried this a few years ago and couldn’t believe how simple the process was. To self-publish a book you’ll first need to write and edit it, create a cover, and then upload to a program such as Amazon’s Kindle Direct Publishing. Don’t expect instant success though. There will need to be a lot of upfront marketing before you can turn this into a passive income stream.

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.
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.
Making legitimate passive income isn’t as difficult as you might think. Some of the best passive income ideas might take a little time to set up but can start cash flowing within a couple of months and will provide a consistent monthly income for years or more. The most important point is just to get started. You make exactly $0 on the passive income sources you never start.
Wow! What an awesome list! My favorite is the stock photography because I love photography. I have had some success there, particularly with one photo I make some decent income from. I think the key with stock photography is finding a shot that is high demand. Then, find a new unique way to frame that shot. This is the reason my St. Louis Arch photo is a top 10 on both ShutterStock and iStockPhoto. Thanks for the awesome ideas above!
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In order not to succumb to that, Flynn says it’s important to know your motivation. “Passive income is important to me not just for the financial security but so I can spend time with my family,” he says. “I’ve been able to work from home and witness all my kids’ firsts. I have a one-year-old and a four-year-old, and that's what drives me and gets me pushing through those hard times and why I keep creating new products and why I want to help other people do the same thing.”
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.
That’s why I sometimes hesitate to even say I participate in affiliate marketing. But that’s not how I, or you, should approach it. I’m here to lead the change and show people there is so much opportunity out there in affiliate marketing the right way (and the smart way). It’s insane to me that more people aren’t really realizing their full potential with this.
So many great tips in this big post, thanks! I think it’s so true that people should focus on the things they do well at and are interested in. And yes save, save, save in the beginning and throughout. I have several interest and dividend earning investments and am looking to expand further. Diversification is a great goal for all of us so we can avoid having all our eggs in one basket.
1 Would you choose WordPress as an easy-start blogging/website content management system? The only thing I know about it is that it exists, I’ve been told by friends who have WP it’s easy to set-up and maintain and I’ve since read lots of info on the Net which reiterates this claim. I believe I read in a reply you wrote to another community member who commented on another post of yours you recommend WP. Is this correct, Chris? Or did I just make that up?
The great part about creating truly passive income is the money comes in every month without you having to sell your investment or worry about running out of money when you retire. The returns are also better for me with rental properties, because my cash flow is producing about a 20 percent cash on cash return and that does not even include equity pay down on my loans or appreciation. The appreciation on my rental properties is a bonus for me, while stock market investors are depending on it.
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